Oxazole-based organic compounds containing benzonaphthofuran and uses thereof

Abstract

The present application relates to the technical field of displays, and more particularly to an oxazole-based organic compound containing benzonaphthofuran and its use. The oxazole-based organic compound containing benzonaphthofuran according to the present application has the following structure: An organic electroluminescent device containing the oxazole-based organic compound containing benzonaphthofuran has a relatively low driving voltage, a relatively high luminous efficiency, and a relatively long lifetime. TIFF2026504543000069.tif2950

Description

[Technical Field]

[0001] [CROSS-REFERENCE TO RELATED APPLICATIONS] This application claims priority to a Chinese patent application filed on December 29, 2023, with application number 202311868168.X, entitled "Benzonaphthofuran-containing oxazole-based organic compounds and their use," and a Chinese patent application filed on March 1, 2024, with application number 202410240330.1, entitled "Benzonaphthofuran-containing oxazole-based organic compounds and their use," the entire contents of which are incorporated herein by reference.

[0002] [Technical field] This application relates to the technical field of displays, and in particular to oxazole-based organic compounds containing benzonaphthofuran and their uses. [Background technology]

[0003] An organic electroluminescent device (OLED) converts electrical energy into light by applying electrical energy to an organic electroluminescent material. It typically has a structure comprising an anode, a cathode, and an organic layer between the anode and the cathode. The organic layers of an OLED device include a hole-injection layer, a hole-transport layer, an electron-blocking layer, an emissive layer (including a host material and a doping material), an electron buffer layer, a hole-blocking layer, an electron-transport layer, and an electron-injection layer. The materials used in the organic layers are classified according to their functions as hole-injection materials, hole-transport materials, electron-blocking materials, emissive materials, electron buffer materials, hole-blocking materials, electron-transport materials, and electron-injection materials. In an OLED device, application of voltage causes holes to be injected from the anode into the emissive layer and electrons to be injected from the cathode into the emissive layer. The recombination of the holes and electrons forms high-energy excitons. This energy excites the organic emissive compound, which then returns to its ground state, generating light by the energy released.

[0004] The most important factor determining the luminous efficiency of an organic electroluminescent device is the emissive material. The emissive material must have high quantum efficiency, high electron and hole mobility, and the resulting emissive layer must be uniform and stable. Depending on the color of the emitted light, emissive materials can be classified as blue, green, red, yellow, or orange. Furthermore, emissive materials can be classified as host materials or doping materials depending on their function.

[0005] However, existing organic electroluminescent materials have relatively low stability, and the HOMO and LUMO energy levels are poorly matched with adjacent energy levels, resulting in carrier mobility imbalance. As a result, organic electroluminescent devices containing these organic electroluminescent materials have problems such as relatively high driving voltage, relatively low luminous efficiency, and relatively short lifespan, which significantly limits the applications of organic electroluminescent devices. Summary of the Invention [Problem to be solved by the invention]

[0006] The present application aims to overcome the problems of existing organic electroluminescent materials, such as relatively low stability and relatively poor matching between adjacent energy levels of the HOMO and LUMO energy levels, which leads to imbalance in carrier mobility, and as a result, the driving voltage of organic electroluminescent devices containing the organic electroluminescent materials is relatively high, the luminous efficiency is relatively low, and the lifetime is relatively short. The present application aims to provide an oxazole-based organic compound containing benzonaphthofuran and use thereof.

[0007] The definitions of substituent terms in this application are as follows:

[0008] As used herein, the term "halogen" may include fluorine, chlorine, bromine, or iodine.

[0009] As used herein, the term "C1-C30 alkyl group" refers to a monovalent substituent derived from a straight- or branched-chain saturated hydrocarbon having from 1 to 30 carbon atoms, examples of which include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl groups.

[0010] As used herein, the term "C3-C30 cycloalkyl group" refers to a group derived from a monocyclic or polycyclic hydrocarbon having 1 to 30 main ring carbon atoms, and the cycloalkane may include a cyclopropyl group, a cyclobutyl group, an adamantyl group, etc.

[0011] In this application, aryl and arylene groups include monocyclic, polycyclic, or fused-ring aryl groups, and the rings may be interrupted by short non-aromatic units or may contain spiro structures. Aryl groups include, but are not limited to, phenyl, biphenyl, triphenyl, naphthyl, phenanthryl, anthracenyl, fluorenyl, and spirobifluorenyl groups. Arylene groups include, but are not limited to, phenylene, biphenylene, terphenylene, naphthylene, phenanthrylene, anthrylene, fluorenylene, and spirobifluorenylene groups.

[0012] In this application, heteroaryl and heteroarylene groups include monocyclic, polycyclic, and fused-ring heteroaryl groups. The rings may be interrupted by short non-aromatic units, and the heteroatoms include nitrogen, oxygen, and sulfur. Heteroaryl groups include furanyl, phenylthio, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiphenyl, isobenzofuranyl, dibenzofuryl, dibenzothiophenyl, benzophenone ... Examples of the alkyl group include, but are not limited to, diisoimidazolyl group, benzothiazolyl group, benzisothiazolyl group, benzisoxazolyl group, benzoxazolyl group, isoindolyl group, indolyl group, indazolyl group, benzothiadiazolyl group, quinolyl group, isoquinolyl group, cinnolinyl group, quinazolinyl group, quinoxalinyl group, carbazolyl group, phenoxazyl group, phenothiazinyl group, phenanthridinyl group, benzodioxolyl group, dihydroacridinyl group, and derivatives thereof.Examples of heteroarylene groups include furanylene groups, thiophenylene groups, pyrrolylene groups, imidazolylene groups, pyrazolylene groups, thiazolylene groups, thiadiazolylene groups, isothiazolylene groups, isoxazolylene groups, oxazolylene groups, oxadiazolylene groups, triazinylene groups, tetrazinylene groups, triazolylene groups, tetrazolylene groups, furazolylene groups, pyridinylene groups, pyrazinylene groups, pyrimidinylene groups, pyridazinylene groups, benzofuranylene groups, benzothiophenylene groups, isobenzofuranylene groups, dibenzofuranylene groups, and dibenzothiophenylene groups. groups, benzimidazolylene groups, benzothiazolylene groups, benzisothiazolylene groups, benzisoxazolylene groups, benzoxazolylene groups, isoindolylene groups, indolylene groups, indazolylene groups, benzothiadiazolylene groups, quinolylene groups, isoquinolylene groups, cinnolinylene groups, quinazolinylene groups, quinoxalinylene groups, carbazolylene groups, phenoxazinylene groups, phenothiazinylene groups, phenanthridinylene groups, benzodioxolylene groups, dihydroacridinylene groups, and derivatives thereof.

[0013] As used herein, the term "substituted" refers to a hydrogen atom in a compound being replaced by another substituent. The position is not limited to a specific position, as long as the hydrogen at that position is replaced by a substituent. When two or more substituents are present, the two or more substituents may be the same or different.

[0014] As used herein, unless otherwise specified, hydrogen atoms include protium, deuterium, and tritium.

[0015] In the present application, the range of the number of carbon atoms is defined in the definition of the group, and the number of carbon atoms is any integer within the defined range. For example, in the case of a C6-C30 aryl group, the number of carbon atoms in the aryl group can be any integer within the range of 6 to 60, such as 6, 8, 10, 13, 15, 17, 20, 22, 25, or 30.

[0016] In this application, TIFF2026504543000002.tif613 represents a bond.

[0017] The scheme adopted in this application is as follows. [Means for solving the problem]

[0018] The present application provides an oxazole-based organic compound containing benzonaphthofuran, having a structure represented by the following formula (1): TIFF2026504543000003.tif2975 (in the formula (1), ring A is a benzene ring, Ar is selected from a substituted or unsubstituted C6 to C60 aryl group, a substituted or unsubstituted C6 to C60 arylamine group, a substituted or unsubstituted C3 to C60 heteroarylamine group, and a substituted or unsubstituted C3 to C30 heteroaryl group; L is selected from a substituted or unsubstituted C6 to C30 arylene group and a substituted or unsubstituted C3 to C30 heteroarylene group; The substituents in the substituted C6 to C60 aryl group, substituted C6 to C60 arylamine group, substituted C3 to C60 heteroarylamine group, substituted C3 to C30 heteroaryl group, substituted C6 to C30 arylene group, and substituted C3 to C30 heteroarylene group are each independently one or a combination of at least two selected from deuterium, halogen, cyano group, C1 to C12 alkyl group, C3 to C12 cycloalkyl group, C6 to C30 aryl group, C3 to C30 heteroaryl group, C6 to C60 arylamine group, and C3 to C60 heteroarylamine group.

[0019] As will be understood, TIFF2026504543000004.tif2949, in formula (1), ring A may be fused to ring C via 1, 2; 2, 3; 3, 4 positions, N may be directly linked to any substitutable position in ring A, ring C, or ring D, and L may be linked to any substitutable position in ring B.

[0020] optionally, Ar is selected from a substituted or unsubstituted C6-C25 aryl group, a substituted or unsubstituted C6-C25 arylamine group, a substituted or unsubstituted C3-C25 heteroarylamine group, and a substituted or unsubstituted C3-C20 heteroaryl group; Here, the substituents in the substituted C6 to C25 aryl group, substituted C6 to C25 arylamine group, substituted C3 to C25 heteroarylamine group, and substituted C3 to C20 heteroaryl group are each independently one or a combination of at least two selected from deuterium, halogen, cyano group, C1 to C12 alkyl group, C3 to C12 cycloalkyl group, C6 to C30 aryl group, C3 to C30 heteroaryl group, C6 to C60 arylamine group, and C3 to C60 heteroarylamine group.

[0021] Optionally, Ar is selected from a substituted or unsubstituted B group, wherein B is selected from phenyl, naphthyl, biphenyl, phenanthryl, fluoranthenyl, chrysenyl, triphenyl, triphenylenyl, phenalenyl, phenylnaphthyl, naphthylphenyl, dimethylfluorenyl, phenylmethylfluorenyl, diphenylfluorenyl, pyridyl, pyridylphenyl, phenylpyridyl, spirobifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirobifluorenyl, dibenzofuryl, benzonaphthofuryl, benzonaphthothienyl, spiro[fluoren-9,9'-xanthene]yl, phenylmethylfluorenyl, dinaphthofuranyl, dinaphthothiophenyl, dibenzothiophenyl, and N,N-diphenylanilino; Here, the substituent of the substituted B group is one or a combination of at least two selected from deuterium, halogen, cyano group, C1 to C12 alkyl group, C3 to C12 cycloalkyl group, C6 to C30 aryl group, C3 to C30 heteroaryl group, C6 to C60 arylamine group, and C3 to C60 heteroarylamine group.

[0022] Optionally, Ar is selected from a phenyl group, a naphthyl group, a biphenyl group, a chrysenyl group, a phenanthryl group, a triphenyl group, a phenylnaphthyl group, a naphthylphenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a spirobifluorenyl group, a phenalenyl group, a dibenzofuryl group, a benzonaphthofuryl group, and an N,N-diphenylanilino group.

[0023] Optionally, L is selected from a substituted or unsubstituted C6-C15 arylene group, wherein the substituents in the substituted C6-C15 arylene group are each independently one or a combination of at least two selected from deuterium, halogen, and a C1-C62 alkyl group; Optionally, L is selected from a phenylene group, a biphenylene group, and a naphthylene group; Optionally, L is selected from a phenylene group, a naphthylene group.

[0024] Optionally, the formula (1) is one selected from the structures shown in the following formulas 1-1 to 1-6. TIFF2026504543000005.tif87116 (where Ar is defined as above.)

[0025] Optionally, the formula (1) is one selected from the structures shown in the following formulas 1-7 to 1-12. TIFF2026504543000006.tif114128 (where Ar is defined as above.)

[0026] Optionally, the oxazole-based organic compound containing benzonaphthofuran is any one selected from the following N-1 to N-208. TIFF2026504543000007.tif87157 TIFF2026504543000008.tif212157 TIFF2026504543000009.tif236157 TIFF2026504543000010.tif230157 TIFF2026504543000011.tif225157 TIFF2026504543000012.tif209157 TIFF2026504543000013.tif228157 TIFF2026504543000014.tif231157 TIFF2026504543000015.tif203157

[0027] The present application provides a light-emitting host material containing the above-described oxazole-based organic compound containing benzonaphthofuran.

[0028] Optionally, the light-emitting host material includes a first host material and a second host material, wherein the first host material is the oxazole-based organic compound containing benzonaphthofuran described above, and the second host material is an organic electroluminescent compound having the structure of the following formula (2): TIFF2026504543000016.tif2171 (in the formula (2), Ar1 is selected from a substituted or unsubstituted C6 to C60 aryl group and a substituted or unsubstituted C3 to C60 heteroaryl group; Substituents in the substituted C6 to C60 aryl group and substituted C3 to C630 heteroaryl group are each independently one or a combination of at least two selected from deuterium, halogen, cyano group, C1 to C12 alkyl group, C3 to C12 cycloalkyl group, C6 to C30 aryl group, C3 to C30 heteroaryl group, C6 to C60 arylamine group, and C3 to C60 heteroarylamine group; Optionally, Ar1 is selected from a substituted or unsubstituted C6-C60 non-fused aryl group, a substituted or unsubstituted C3-C60 non-fused heteroaryl group; the substituents in the substituted C6 to C60 non-fused aryl group and the substituted C3 to C60 non-fused heteroaryl group are each independently one or a combination of at least two selected from deuterium, halogen, a cyano group, a C1 to C12 alkyl group, a C3 to C12 cycloalkyl group, a C6 to C30 aryl group, a C3 to C30 heteroaryl group, a C6 to C60 arylamine group, and a C3 to C60 heteroarylamine group; Optionally, Ar1 is selected from a substituted or unsubstituted C6-C20 non-fused aryl group, a substituted or unsubstituted C3-C20 non-fused heteroaryl group; the substituents in the substituted C6 to C20 non-fused aryl group and the substituted C3 to C20 non-fused heteroaryl group are each independently one or a combination of at least two selected from deuterium, halogen, cyano group, C1 to C12 alkyl group, C3 to C12 cycloalkyl group, C6 to C30 aryl group, C3 to C30 heteroaryl group, C6 to C60 arylamine group, and C3 to C60 heteroarylamine group; Optionally, Ar1 is selected from a substituted or unsubstituted A group, wherein A group is one selected from a phenyl group, a biphenyl group, and a triphenyl group; wherein the substituents in the substituted A group are selected from deuterium, phenyl, and naphthyl; Optionally, Ar1 is selected from a phenyl group, a biphenyl group, a triphenyl group, and a naphthylphenyl group.

[0029] Optionally, the organic electroluminescent compound having the structure of the following formula (2) is any one selected from the following M-1 to M-104. TIFF2026504543000017.tif66157 TIFF2026504543000018.tif213157 TIFF2026504543000019.tif216157 TIFF2026504543000020.tif239157 TIFF2026504543000021.tif126157

[0030] optionally, a mass ratio of the first host material to the second host material is from 9:1 to 1:9; optionally, a mass ratio of the first host material to the second host material is from 2:8 to 8:2; optionally, a mass ratio of the first host material to the second host material is from 3:7 to 7:3; Further optionally, the mass ratio of the first host material to the second host material is 4:6 to 6:4.

[0031] The present application further provides an organic electroluminescent material comprising the above-mentioned benzonaphthofuran-containing oxazole-based organic compound or the above-mentioned light-emitting host material.

[0032] The present application provides a light-emitting device comprising: a cathode; an anode; and an organic layer located between the cathode and the anode, wherein the organic layer contains the above-described oxazole-based organic compound containing benzonaphthofuran, the above-described light-emitting host material, or the above-described organic electroluminescent material; Optionally, the organic layer comprises one or more of a hole injection layer, a hole transport layer, an emissive layer, an electron transport layer, an electron injection layer; Optionally, the hole transport layer comprises the benzonaphthofuran-containing oxazole-based organic compound, the light-emitting host material, or the organic electroluminescent material; Optionally, an organic electroluminescent device is provided, wherein the light-emitting layer comprises the above-described benzonaphthofuran-containing oxazole-based organic compound, the above-described light-emitting host material, or the above-described organic electroluminescent material.

[0033] The present application provides the use of the organic electroluminescent device in a fiber optic device, a lighting device, an electrophotographic photoreceptor device, a photoelectric converter, an organic solar cell, a switching element device, an organic light-emitting field effect transistor, an image sensor, or a dye laser. [Effects of the Invention]

[0034] The beneficial effects of the present invention are as follows:

[0035] The oxazole-based organic compound containing benzonaphthofuran according to the present invention has a structure represented by formula (1), and by further limiting the types of substituents, the structural stability of the compound is improved. The HOMO and LUMO energy levels of the oxazole-based organic compound containing benzonaphthofuran have a relatively high degree of matching with adjacent energy levels, and therefore the carrier mobility of the oxazole-based organic compound containing benzonaphthofuran is relatively balanced. Therefore, an organic electroluminescent device containing the oxazole-based organic compound containing benzonaphthofuran has a relatively low driving voltage, a relatively high luminous efficiency, and a relatively long lifetime.

[0036] Furthermore, the oxazole-based organic compound containing benzonaphthofuran according to the present invention has good electron transport properties and can be used as an electron transport material or a light-emitting material.

[0037] Furthermore, the organic electroluminescent material according to the present application comprises an oxazole-based organic compound containing benzonaphthofuran based on the structure of formula (1), whereby an organic electroluminescent device comprising the organic electroluminescent material has a relatively low driving voltage, a relatively high luminous efficiency, and a relatively long lifespan.

[0038] In order to more clearly describe the specific embodiments of the present invention or the technical solutions in the prior art, the following will briefly describe the drawings used to describe the specific embodiments or the prior art. Obviously, the drawings described below are some embodiments of the present invention, and those skilled in the art can obtain other drawings based on these drawings without any creative efforts. [Brief explanation of the drawings]

[0039] [Figure 1] 1 is a structural diagram of an organic electroluminescence element in an element example of the present application. DETAILED DESCRIPTION OF THE INVENTION

[0040] The following examples are provided for a better understanding of the present application, and are not intended to limit the best embodiment, nor to limit the content and scope of protection of the present application. Any identical or similar products obtained by anyone under the teaching of the present application or by combining the features of the present application with other prior art shall fall within the scope of protection of the present application.

[0041] If no specific experimental steps or conditions are specified in the examples, they can be carried out according to conventional experimental steps or conditions described in the literature in the field. All reagents and equipment without manufacturer names are commercially available, conventional reagent products.

[0042] The term "organic electroluminescent material" in the present disclosure refers to a material that can be used in an organic electroluminescent device and that can contain at least one compound. The organic electroluminescent material can be contained in any layer that constitutes an organic electroluminescent device, as needed. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole auxiliary material, an emission auxiliary material, an electron blocking material, an emission material (including a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, or the like.

[0043] In the present disclosure, the term "multiple organic electroluminescent materials" refers to one or more organic electroluminescent materials comprising a combination of at least two compounds, and the materials may be contained in any layer constituting an organic electroluminescent device. It may refer to both the materials before being incorporated into an organic electroluminescent device (e.g., before vapor deposition) and the materials after being incorporated into an organic electroluminescent device (e.g., after vapor deposition). For example, the multiple organic electroluminescent materials may be a combination of at least two compounds, and the materials may be contained in at least one of a hole injection layer, a hole transport layer, a hole auxiliary layer, an emissive auxiliary layer, an electron blocking layer, an emissive layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. The at least two compounds may be contained in the same layer or different layers, and may be mixed-evaporated, co-evaporated, or evaporated separately.

[0044] In the present application, the oxazole-based organic compound containing benzonaphthofuran having the structure of formula (1) is prepared via the following synthetic route.

[0045] 1. Synthesis of intermediate Nn-A: The reactants Nn-1 and Nn-2 undergo Suzuki cross-coupling reaction, and the reaction scheme is as follows: TIFF2026504543000022.tif1498

[0046] 2. Synthesis of compound Nn: Intermediates Nn-A and Nn-B undergo a Buchwald-Hartwig cross-coupling reaction, as shown below. TIFF2026504543000023.tif26146

[0047] In the present application, the compound having the structure shown in formula (2) is prepared via the following synthetic route: TIFF2026504543000024.tif37148

[0048] The intermediate raw materials An, Bn, and Cn can all be purchased directly or synthesized using conventional reaction routes and conditions with reference to existing literature reported methods.

[0049] The specific structures of the intermediate materials used in the examples of the present application are as follows:

[0050] The specific structure of Bn is as follows: TIFF2026504543000025.tif36156

[0051] The specific structure of Cn is as follows: TIFF2026504543000026.tif26101

[0052] Example 1 This example provides a benzonaphthofuran-containing oxazole-based organic compound N-1, and the synthesis of the benzonaphthofuran-containing oxazole-based organic compound N-1 specifically includes the following steps: TIFF2026504543000027.tif32152

[0053] Synthesis of intermediate N1-A A three-necked reaction flask equipped with a mechanical stirrer, thermometer, and condenser was purged with nitrogen. The raw materials, N1-1 (10 g, 36.63 mmol), N1-2 (5.72 g, 36.63 mmol), tetrakis(triphenylphosphine)palladium(0) (0.85 g, 0.73 mmol), potassium carbonate (10.11 g, 73.27 mmol), toluene (70 mL), ethanol (30 mL), and water (30 mL), were added sequentially. The mixture was stirred at 65 °C for 2 h. After completion of the reaction, the organic layer was extracted with ethyl acetate (EA), the remaining water was removed with anhydrous sodium sulfate, and the residue was dried and purified by column chromatography to obtain compound N1-A (10.06 g, 90% yield).

[0054] Synthesis of intermediate N1-B After purging with nitrogen, a three-necked reaction flask equipped with a mechanical stirrer, thermometer, and condenser was added. Then, 10 g (32.78 mmol) of N1-A (as an intermediate), 3.1 g (32.78 mmol) of N1-3 (as an intermediate), 0.6 g (0.66 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.67 g (1.64 mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 6.3 g (65.56 mmol) of sodium t-butoxide, and 100 mL of toluene were added sequentially. The mixture was refluxed and stirred at 110 °C for 3 h. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA). The remaining water was removed with anhydrous sodium sulfate. The residue was dried and purified by column chromatography to obtain 8.31 g (82% yield) of compound N1-B.

[0055] Synthesis of compound N-1 After purging the atmosphere with nitrogen in a three-necked reaction flask equipped with a mechanical stirrer, thermometer, and condenser, 8.30 g (26.85 mmol) of N1-B (intermediate), 7.95 g (26.85 mmol) of N1-4 (intermediate), 0.49 g (0.54 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.55 g (1.34 mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 5.16 g (53.70 mmol) of sodium t-butoxide, and 100 mL of toluene were added sequentially. The mixture was refluxed and stirred at 110 °C for 3 h. After completion of the reaction, the organic layer was extracted with ethyl acetate (EA), the residual water was removed with anhydrous sodium sulfate, and the residue was dried and purified by column chromatography to obtain 11.80 g (76% yield) of benzonaphthofuran-containing oxazole-based organic compound N-1. Elemental analysis:C 41 H 26 N2O2; Calculated: C, 85.10; H, 4.53; N, 4.84; O, 5.53; Found: C, 85.12; H, 4.52; N, 4.83; HRMS (ESI) m / z [M+H]+: Calculated: 578.20; Found: 579.21.

[0056] Example 2 This example provides a benzonaphthofuran-containing oxazole-based organic compound N-6, and the synthesis of the benzonaphthofuran-containing oxazole-based organic compound N-6 specifically includes the following steps: TIFF2026504543000028.tif43162

[0057] After purging the atmosphere with nitrogen in a three-necked reaction flask equipped with a mechanical stirrer, thermometer, and condenser, 10 g (32.78 mmol) of N1-A (as an intermediate), 10.92 g (32.78 mmol) of N6-3 (as an intermediate), 0.6 g (0.66 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.67 g (1.64 mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 6.3 g (65.56 mmol) of sodium t-butoxide, and 100 mL of toluene were added sequentially. The mixture was refluxed and stirred at 110 °C for 3 h. After completion of the reaction, the organic layer was extracted with ethyl acetate (EA), the remaining water was removed with anhydrous sodium sulfate, and the residue was dried and purified by column chromatography to obtain 14.41 g (73% yield) of compound N6-B.

[0058] After purging the atmosphere with nitrogen in a three-necked reaction flask equipped with a mechanical stirrer, thermometer, and condenser, 10 g (16.60 mmol) of N6-B (intermediate), 4.91 g (16.60 mmol) of N1-4 (intermediate), 0.30 g (0.33 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.34 g (0.83 mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 3.19 g (33.21 mmol) of sodium t-butoxide, and 100 mL of toluene were added sequentially. The mixture was refluxed and stirred at 110 °C for 3 h. After completion of the reaction, the organic layer was extracted with ethyl acetate (EA), the residual water was removed with anhydrous sodium sulfate, and the residue was dried and purified by column chromatography to obtain 9.24 g (68% yield) of benzonaphthofuran-containing oxazole-based organic compound N-6. Elemental analysis:C 60 H 38N2O2; Calculated: C, 88.00; H, 4.68; N, 3.42; O, 3.91; Found: C, 88.01; H, 4.68; N, 3.41; HRMS (ESI) m / z [M+H]+: Calculated: 818.29; Found: 819.28.

[0059] Example 3 This example provides a benzonaphthofuran-containing oxazole-based organic compound N-18, and the synthesis of the benzonaphthofuran-containing oxazole-based organic compound N-18 specifically includes the following steps: TIFF2026504543000029.tif48160

[0060] After purging the atmosphere with nitrogen in a three-necked reaction flask equipped with a mechanical stirrer, thermometer, and condenser, 10 g (32.78 mmol) of N1-A (as an intermediate), 8.53 g (32.78 mmol) of N18-3, 0.60 g (0.66 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.67 g (1.64 mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 6.3 g (65.56 mmol) of sodium t-butoxide, and 100 mL of toluene were added sequentially. The mixture was refluxed and stirred at 110 °C for 3 h. After completion of the reaction, the organic layer was extracted with ethyl acetate (EA), the remaining water was removed with anhydrous sodium sulfate, and the residue was dried and purified by column chromatography to obtain 13.19 g (76% yield) of compound N18-B.

[0061] After purging the atmosphere with nitrogen in a three-necked reaction flask equipped with a mechanical stirrer, thermometer, and condenser, 10 g (18.90 mmol) of N18-B, 5.59 g (18.90 mmol) of N18-4, 0.35 g (0.38 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.39 g (0.94 mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 3.63 g (37.79 mmol) of sodium t-butoxide, and 100 mL of toluene were added sequentially. The mixture was refluxed and stirred at 110 °C for 3 h. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), the residual water was removed with anhydrous sodium sulfate, and the residue was dried and purified by column chromatography to obtain 10.70 g (76% yield) of organic electroluminescent compound N-18. Elemental analysis:C 53 H 35 N3O2; Calculated: C, 85.35; H, 4.73; N, 5.63; O, 4.29; Found: C, 85.37; H, 4.72; N, 5.62; HRMS (ESI) m / z [M+H]+: Calculated: 745.27; Found: 746.26.

[0062] Example 4 This example provides a benzonaphthofuran-containing oxazole-based organic compound N-30, and the synthesis of the benzonaphthofuran-containing oxazole-based organic compound N-30 specifically includes the following steps: TIFF2026504543000030.tif43155

[0063] After purging the atmosphere with nitrogen in a three-necked reaction flask equipped with a mechanical stirrer, thermometer, and condenser, 10 g (32.78 mmol) of N1-A (as an intermediate), 5.54 g (32.78 mmol) of N30-3 (as an intermediate), 0.60 g (0.66 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.67 g (1.64 mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 6.30 g (65.56 mmol) of sodium t-butoxide, and 100 mL of toluene were added sequentially. The mixture was refluxed and stirred at 110 °C for 3 h. After completion of the reaction, the organic layer was extracted with ethyl acetate (EA), the residual water was removed with anhydrous sodium sulfate, and the residue was dried and purified by column chromatography to obtain 11.49 g (80% yield) of compound N30-B.

[0064] After purging the atmosphere with nitrogen in a three-necked reaction flask equipped with a mechanical stirrer, thermometer, and condenser, 10 g (22.82 mmol) of N30-B (as intermediate), 6.75 g (22.82 mmol) of N30-4 (as intermediate), 0.42 g (0.46 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.47 g (1.14 mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 4.39 g (45.64 mmol) of sodium t-butoxide, and 100 mL of toluene were added sequentially. The mixture was refluxed and stirred at 110 °C for 3 h. After completion of the reaction, the organic layer was extracted with ethyl acetate (EA), the residual water was removed with anhydrous sodium sulfate, and the residue was dried and purified by column chromatography to obtain 10.75 g (72% yield) of the benzonaphthofuran-containing oxazole-based organic compound N-30. Elemental analysis:C 47 H 30 N2O2; Calculated: C, 86.22; H, 4.62; N, 4.28; O, 4.89; Found: C, 86.20; H, 4.63; N, 4.29; HRMS (ESI) m / z [M+H]+: Calculated: 654.23; Found: 654.24.

[0065] Example 5 This example provides a benzonaphthofuran-containing oxazole-based organic compound N-45, and the synthesis of the benzonaphthofuran-containing oxazole-based organic compound N-45 specifically includes the following steps: TIFF2026504543000031.tif49145

[0066] After purging the atmosphere with nitrogen in a three-necked reaction flask equipped with a mechanical stirrer, thermometer, and condenser, 10 g (32.78 mmol) of N1-A (as an intermediate), 7.18 g (32.78 mmol) of N45-3 (as an intermediate), 0.60 g (0.66 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.67 g (1.64 mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 6.30 g (65.56 mmol) of sodium t-butoxide, and 100 mL of toluene were added sequentially. The mixture was refluxed and stirred at 110 °C for 3 h. After completion of the reaction, the organic layer was extracted with ethyl acetate (EA), the residual water was removed with anhydrous sodium sulfate, and the residue was dried and purified by column chromatography to obtain 12.16 g (76% yield) of compound N45-B.

[0067] After purging the atmosphere with nitrogen in a three-necked reaction flask equipped with a mechanical stirrer, thermometer, and condenser, 7.50 g (15.36 mmol) of N45-B (as intermediates), 3.87 g (15.36 mmol) of N45-4, 0.28 g (0.31 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.31 g (0.77 mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 2.95 g (30.73 mmol) of sodium t-butoxide, and 80 mL of toluene were added sequentially. The mixture was refluxed and stirred at 110 °C for 3 h. After completion of the reaction, the organic layer was extracted with ethyl acetate (EA), the residual water was removed with anhydrous sodium sulfate, and the residue was dried and purified by column chromatography to obtain 8.22 g (76% yield) of the benzonaphthofuran-containing oxazole-based organic compound N-45. Elemental analysis:C 51 H 32N2O2; Calculated: C, 86.91; H, 4.58; N, 3.97; O, 4.54; Found: C, 86.93; H, 4.57; N, 3.96; HRMS (ESI) m / z [M+H]+: Calculated: 704.25; Found: 705.26.

[0068] Example 6 This example provides a benzonaphthofuran-containing oxazole-based organic compound N-72, and the synthesis of the benzonaphthofuran-containing oxazole-based organic compound N-72 specifically includes the following steps: TIFF2026504543000032.tif26157

[0069] Synthesis of intermediate N72-A A three-necked reaction flask equipped with a mechanical stirrer, thermometer, and condenser was purged with nitrogen. The raw materials, N1-1 (10 g, 36.63 mmol), N72-2 (5.72 g, 36.63 mmol), tetrakis(triphenylphosphine)palladium(0) (0.85 g, 0.73 mmol), potassium carbonate (10.11 g, 73.27 mmol), toluene (70 mL), ethanol (30 mL), and water (30 mL), were added sequentially. The mixture was stirred at 65 °C for 2 h. After completion of the reaction, the organic layer was extracted with ethyl acetate (EA), the remaining water was removed with anhydrous sodium sulfate, and the residue was dried and purified by column chromatography to obtain compound N72-A (9.50 g, 85% yield).

[0070] Synthesis of intermediate N72-B After purging with nitrogen, a three-necked reaction flask equipped with a mechanical stirrer, thermometer, and condenser was added with 9.50 g (31.14 mmol) of N72-A (as an intermediate), 6.82 g (31.14 mmol) of N73-3 (as an intermediate), 0.57 g (0.62 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.64 g (1.56 mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 5.99 g (62.28 mmol) of sodium t-butoxide, and 100 mL of toluene were sequentially added. The mixture was refluxed and stirred at 110 °C for 3 h. After completion of the reaction, the organic layer was extracted with ethyl acetate (EA), the remaining water was removed with anhydrous sodium sulfate, and the residue was dried and purified by column chromatography to obtain 11.10 g (73% yield) of compound N72-B.

[0071] After purging the atmosphere with nitrogen in a three-necked reaction flask equipped with a mechanical stirrer, thermometer, and condenser, 10 g (20.48 mmol) of N72-B (intermediate), 6.06 g (20.48 mmol) of N72-4, 0.37 g (0.41 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.42 g (1.02 mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 3.94 g (40.97 mmol) of sodium t-butoxide, and 100 mL of toluene were added sequentially. The mixture was refluxed and stirred at 110 °C for 3 h. After completion of the reaction, the organic layer was extracted with ethyl acetate (EA), the residual water was removed with anhydrous sodium sulfate, and the residue was dried and purified by column chromatography to obtain 10.82 g (75% yield) of the benzonaphthofuran-containing oxazole-based organic compound N-72. Elemental analysis: C51H32N2O2; theoretical: C, 86.91; H, 4.58; N, 3.97; O, 4.54; found: C, 86.93; H, 4.57; N, 3.96; HRMS (ESI) m / z [M+H]+: theoretical: 704.25; found: 705.26.

[0072] Example 7 This example provides a benzonaphthofuran-containing oxazole-based organic compound N-95, and the synthesis of the benzonaphthofuran-containing oxazole-based organic compound N-95 specifically includes the following steps: TIFF2026504543000033.tif32147

[0073] A three-necked reaction flask equipped with a mechanical stirrer, thermometer, and condenser was purged with nitrogen. The raw materials, N1-1 (10 g, 36.63 mmol), N95-2 (5.72 g, 36.63 mmol), tetrakis(triphenylphosphine)palladium(0) (0.85 g, 0.73 mmol), potassium carbonate (10.11 g, 73.27 mmol), toluene (70 mL), ethanol (30 mL), and water (30 mL), were added sequentially. The mixture was stirred at 65 °C for 2 h. After completion of the reaction, the organic layer was extracted with ethyl acetate (EA), the remaining water was removed with anhydrous sodium sulfate, and the residue was dried and purified by column chromatography to obtain compound N95-A (9.28 g, 83% yield).

[0074] After purging the atmosphere with nitrogen in a three-necked reaction flask equipped with a mechanical stirrer, thermometer, and condenser, 9.28 g (30.42 mmol) of N95-A, 6.67 g (30.42 mmol) of N72-3, 0.56 g (0.61 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.62 g (1.52 mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 5.85 g (60.84 mmol) of sodium t-butoxide, and 100 mL of toluene were added sequentially. The mixture was refluxed and stirred at 110 °C for 3 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate (EA), the remaining water was removed with anhydrous sodium sulfate, and the residue was dried and purified by column chromatography to obtain 10.69 g (72% yield) of compound N95-B.

[0075] After purging the atmosphere with nitrogen in a three-necked reaction flask equipped with a mechanical stirrer, thermometer, and condenser, 10 g (20.48 mmol) of N95-B, 6.06 g (20.48 mmol) of N95-4, 0.37 g (0.41 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.42 g (1.02 mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 3.94 g (40.97 mmol) of sodium t-butoxide, and 100 mL of toluene were added sequentially. The mixture was refluxed and stirred at 110 °C for 3 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate (EA), the residual water was removed with anhydrous sodium sulfate, and the residue was dried and purified by column chromatography to obtain 10.10 g (70% yield) of the benzonaphthofuran-containing oxazole-based organic compound N-95. Elemental analysis:C 51 H 32 N2O2; Calculated: C, 86.91; H, 4.58; N, 3.97; O, 4.54; Found: C, 86.90; H, 4.58; N, 3.98; HRMS (ESI) m / z [M+H]+: Calculated: 704.25; Found: 705.26.

[0076] Example 8 This example provides a benzonaphthofuran-containing oxazole-based organic compound N-134, and the synthesis of the benzonaphthofuran-containing oxazole-based organic compound N-134 specifically includes the following steps: TIFF2026504543000034.tif35115

[0077] After purging the atmosphere with nitrogen in a three-necked reaction flask equipped with a mechanical stirrer, thermometer, and condenser, 8.60 g (16.25 mmol) of N18-B (as intermediates), 4.10 g (16.25 mmol) of N134-4, 0.30 g (0.33 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.33 g (0.81 mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 3.12 g (32.50 mmol) of sodium t-butoxide, and 100 mL of toluene were added sequentially. The mixture was refluxed and stirred at 110 °C for 3 h. After completion of the reaction, the organic layer was extracted with ethyl acetate (EA), the residual water was removed with anhydrous sodium sulfate, and the residue was dried and purified by column chromatography to obtain 9.20 g (76% yield) of the benzonaphthofuran-containing oxazole-based organic compound N-134. Elemental analysis:C 53 H 35 N3O2; Calculated: C, 85.35; H, 4.73; N, 5.63; O, 4.29; Found: C, 85.33; H, 4.74; N, 5.64; HRMS (ESI) m / z [M+H]+: Calculated: 745.27; Found: 746.29.

[0078] Example 9 This example provides a benzonaphthofuran-containing oxazole-based organic compound N-148, and the synthesis of the benzonaphthofuran-containing oxazole-based organic compound N-148 specifically includes the following steps: TIFF2026504543000035.tif27147

[0079] After purging the atmosphere with nitrogen in a three-necked reaction flask equipped with a mechanical stirrer, thermometer, and condenser, 10 g (32.78 mmol) of N73-A (as an intermediate), 5.54 g (32.78 mmol) of N30-3 (as an intermediate), 0.60 g (0.66 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.67 g (1.64 mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 6.3 g (65.56 mmol) of sodium t-butoxide, and 100 mL of toluene were added sequentially. The mixture was refluxed and stirred at 110 °C for 3 h. After completion of the reaction, the organic layer was extracted with ethyl acetate (EA), the residual water was removed with anhydrous sodium sulfate, and the residue was dried and purified by column chromatography to obtain 11.34 g (79% yield) of compound N148-B.

[0080] After purging the atmosphere with nitrogen in a three-necked reaction flask equipped with a mechanical stirrer, thermometer, and condenser, 10 g (22.82 mmol) of N148-B (as intermediates), 6.57 g (22.82 mmol) of N18-4, 0.42 g (0.46 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.47 g (1.14 mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 4.39 g (45.64 mmol) of sodium t-butoxide, and 100 mL of toluene were added sequentially. The mixture was refluxed and stirred at 110 °C for 3 h. After completion of the reaction, the organic layer was extracted with ethyl acetate (EA), the residual water was removed with anhydrous sodium sulfate, and the residue was dried and purified by column chromatography to obtain 11.20 g (75% yield) of the benzonaphthofuran-containing oxazole-based organic compound N-148. Elemental analysis:C 47 H 30 N2O2; Calculated: C, 86.22; H, 4.62; N, 4.28; O, 4.89; Found: C, 86.22; H, 4.62; N, 4.28; HRMS (ESI) m / z [M+ H]+: Calculated: 654.23; Found: 655.21.

[0081] Example 10 This example provides an organic electroluminescent compound N-173, and the synthesis of the organic electroluminescent compound N-173 specifically includes the following steps: TIFF2026504543000036.tif34140

[0082] After purging the atmosphere with nitrogen in a three-necked reaction flask equipped with a mechanical stirrer, thermometer, and condenser, 10 g (32.78 mmol) of N73-A (as an intermediate), 4.69 g (32.78 mmol) of N173-3, 0.60 g (0.66 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.67 g (1.64 mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 6.30 g (65.56 mmol) of sodium t-butoxide, and 100 mL of toluene were added sequentially. The mixture was refluxed and stirred at 110 °C for 3 h. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), the remaining water was removed with anhydrous sodium sulfate, and the residue was dried and purified by column chromatography to obtain 9.73 g (72% yield) of compound N173-B.

[0083] After purging the atmosphere with nitrogen in a three-necked reaction flask equipped with a mechanical stirrer, thermometer, and condenser, 9.70 g (23.53 mmol) of N173-B (as intermediates), 6.97 g (23.53 mmol) of N173-4, 0.43 g (0.47 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.48 g (1.18 mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 4.52 g (47.07 mmol) of sodium t-butoxide, and 100 mL of toluene were added sequentially. The mixture was refluxed and stirred at 110 °C for 3 h. After completion of the reaction, the organic layer was extracted with ethyl acetate (EA), the remaining water was removed with anhydrous sodium sulfate, and the residue was dried and purified by column chromatography to obtain 10.35 g (70% yield) of compound N-173. Elemental analysis:C 45 H 28N2O2; Calculated: C, 85.97; H, 4.49; N, 4.46; O, 5.09; Found: C, 85.96; H, 4.48; N, 4.48; HRMS (ESI) m / z [M+H]+: Calculated: 628.22; Found: 629.24.

[0084] Example 11 This example provides an organic electroluminescent compound N-182, and the synthesis of the organic electroluminescent compound N-182 specifically includes the following steps: TIFF2026504543000037.tif32164

[0085] A three-necked reaction flask equipped with a mechanical stirrer, thermometer, and condenser was purged with nitrogen. The following raw materials were added sequentially: N182-1 (10 g, 36.63 mmol), N182-2 (5.72 g, 36.63 mmol), tetrakis(triphenylphosphine)palladium(0) (0.85 g, 0.73 mmol), potassium carbonate (10.11 g, 73.27 mmol), toluene (70 mL), ethanol (30 mL), and water (30 mL). The mixture was stirred at 65 °C for 2 h. After completion of the reaction, the organic layer was extracted with ethyl acetate (EA), the remaining water was removed with anhydrous sodium sulfate, and the residue was dried and purified by column chromatography to obtain compound N182-A (8.94 g, 80% yield).

[0086] After purging the atmosphere with nitrogen in a three-necked reaction flask equipped with a mechanical stirrer, thermometer, and condenser, 8.94 g (29.31 mmol) of N182-A (as an intermediate), 4.96 g (29.31 mmol) of N30-3, 0.54 g (0.59 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.60 g (1.47 mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 5.63 g (58.61 mmol) of sodium t-butoxide, and 100 mL of toluene were added sequentially. The mixture was refluxed and stirred at 110 °C for 3 h. After completion of the reaction, the organic layer was extracted with ethyl acetate (EA), the remaining water was removed with anhydrous sodium sulfate, and the residue was dried and purified by column chromatography to obtain 10.01 g (78% yield) of compound N182-B.

[0087] After purging the atmosphere with nitrogen in a three-necked reaction flask equipped with a mechanical stirrer, thermometer, and condenser, 10.01 g (22.85 mmol) of N182-B (intermediate), 6.76 g (22.85 mmol) of N1-4, 0.42 g (0.46 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.47 g (1.14 mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 4.39 g (45.69 mmol) of sodium t-butoxide, and 100 mL of toluene were added sequentially. The mixture was refluxed and stirred at 110 °C for 3 h. After completion of the reaction, the organic layer was extracted with ethyl acetate (EA), the remaining water was removed with anhydrous sodium sulfate, and the residue was dried and purified by column chromatography to obtain 11.21 g (75% yield) of compound N-182. Elemental analysis:C 47 H 30 N2O2; Calculated: C, 86.22; H, 4.62; N, 4.28; O, 4.89; Found: C, 86.24; H, 4.61; N, 4.27; HRMS (ESI) m / z [M+H]+: Calculated: 654.23; Found: 654.21.

[0088] Example 12 TIFF2026504543000038.tif43144

[0089] After purging the atmosphere with nitrogen in a three-necked reaction flask equipped with a mechanical stirrer, thermometer, and condenser, 8.94 g (29.31 mmol) of N182-A (as intermediate), 4.96 g (29.31 mmol) of N173-3 (as intermediate), 0.54 g (0.59 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.60 g (1.47 mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 5.63 g (58.61 mmol) of sodium t-butoxide, and 100 mL of toluene were added sequentially. The mixture was refluxed and stirred at 110 °C for 3 h. After completion of the reaction, the organic layer was extracted with ethyl acetate (EA), the residual water was removed with anhydrous sodium sulfate, and the residue was dried and purified by column chromatography to obtain 10.01 g (78% yield) of compound N207-B.

[0090] After purging the atmosphere with nitrogen in a three-necked reaction flask equipped with a mechanical stirrer, thermometer, and condenser, 10 g (24.26 mmol) of N207-B, 7.18 g (24.26 mmol) of N72-4, 0.44 g (0.49 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.50 g (1.21 mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 4.66 g (48.52 mmol) of sodium t-butoxide, and 100 mL of toluene were added sequentially. The mixture was refluxed and stirred at 110 °C for 3 h. After completion of the reaction, the organic layer was extracted with ethyl acetate (EA), the remaining water was removed with anhydrous sodium sulfate, and the residue was dried and purified by column chromatography to obtain 10.97 g (72% yield) of compound N-207. Elemental analysis:C 45 H 28 N2O2; Calculated: C, 85.97; H, 4.49; N, 4.46; O, 5.09; Found: C, 85.95; H, 4.49; N, 4.48; HRMS (ESI) m / z [M+H]+: Calculated: 628.22; Found: 628.21.

[0091] The preparation methods of Examples 13 to 21 are similar to that of Example 1, and specifically, the raw materials used and the obtained products in Examples 13 to 21 are shown in Table 1 below.

[0092] [Table 1] TIFF2026504543000040.tif225164

[0093] Data characterizing the products prepared in Examples 13-21 are presented in Table 2.

[0094] [Table 2]

[0095] Example 22 This example provides an organic electroluminescent compound M-3 in a light-emitting host material, and the synthesis of the organic electroluminescent compound M-3 specifically includes the following steps: TIFF2026504543000042.tif42149

[0096] A 100 ml three-necked round-bottom flask was prepared, and a stirrer was placed in it. A reflux condenser was connected to it. Under nitrogen protection, raw material A-3 (1 mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine (1.2 mmol), Pd(dppf)Cl (0.03 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL) were sequentially added. The mixture was heated to 60 °C and reacted for 5 hours. After completion of the reaction, the temperature was lowered to room temperature, and the mixture was quenched with saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator. The crude product was separated by column chromatography (ethyl acetate: n-hexane = 1:50) to obtain intermediate M-3-1 (yield 61%).

[0097] A 100 mL three-necked round-bottom flask was prepared, equipped with a stirrer and a reflux condenser. Under nitrogen protection, intermediate M-3-1 (1 mmol), 4,4,5,5-tetramethyl-2-(naphtho[2,1-b]benzofuran-1-yl)-1,3,2-dioxaborolane (C-1) (1.2 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL) were sequentially added. The mixture was heated to 90 °C and reacted for 5 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered, and suctioned. The filter cake was rinsed twice with deionized water and twice with ethanol. The crude product was further purified twice by recrystallization from o-dichlorobenzene to obtain organic electroluminescent compound M-3 (yield 42%). Elemental analysis:C 41 H 25 N3. Theoretical value: C,85.54;H,4.38;N,7.30;O,2.78;Actual value:C,85.48;H,4.50;N,7.24;HRMS(ESI)m / z[M+H] + :Theoretical value: 575.20; Actual value: 576.20.

[0098] Example 23 This example provides an organic electroluminescent compound M-54 in an emitting host material, and the synthesis of the organic electroluminescent compound M-54 specifically includes the following steps: TIFF2026504543000043.tif31110

[0099] A 100 mL three-necked round-bottom flask was prepared, and a stirrer was placed in it. A reflux condenser was connected to it. Under nitrogen protection, raw material A-54 (1 mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine (1.2 mmol), Pd(dppf)Cl (0.03 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL) were sequentially added. The mixture was heated to 60 °C and reacted for 5 hours. After completion of the reaction, the temperature was lowered to room temperature, and the mixture was quenched with saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator. The crude product was separated by column chromatography (ethyl acetate: n-hexane = 1:50) to obtain intermediate M-54-1 (yield 45%).

[0100] A 100 mL three-necked round-bottom flask was prepared, equipped with a stirrer and a reflux condenser, and under nitrogen protection, intermediate M-54-1 (1 mmol), 4,4,5,5-tetramethyl-2-(naphtho[2,1-b]benzofuran-5-yl)-1,3,2-dioxaborolane (C-4) (1.2 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL) were sequentially added. The mixture was heated to 90 °C and reacted for 5 h. After the reaction was completed, the mixture was cooled to room temperature, filtered, and suctioned. The filter cake was rinsed twice with deionized water and twice with ethanol. The crude product was further purified twice by recrystallization from o-dichlorobenzene to give organic electroluminescent compound 54 (yield 46%). Elemental analysis:C 41 H 25 N3. Theoretical value: C,85.54;H,4.38;N,7.30;O, 2.78;Actual value: C,85.44;H,4.54;N,7.24;HRMS(ESI)m / z[M+H] + :Theoretical value: 575.20; Actual value: 576.20.

[0101] Example 24 This example provides an organic electroluminescent compound M-58 in an emitting host material, and the synthesis of the organic electroluminescent compound M-58 specifically includes the following steps: TIFF2026504543000044.tif31136

[0102] A 100 mL three-necked round-bottom flask was prepared, equipped with a stirrer and a reflux condenser, and under nitrogen protection, raw material A-58 (1 mmol), 2-([1,1'-biphenyl]-3-yl)-4,6-dichloro-1,3,5-triazine, i.e., B-2 (1.2 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL) were sequentially added. The mixture was heated to 60 °C and reacted for 5 hours. After completion of the reaction, the temperature was lowered to room temperature, quenched with saturated aqueous ammonium chloride, extracted with ethyl acetate, and the organic phase was dried over anhydrous magnesium sulfate. The solvent was removed using a rotary evaporator, and the crude product was separated by column chromatography (ethyl acetate:n-hexane = 1:50) to obtain intermediate M-59-1 (yield 54%).

[0103] A 100 mL three-necked round-bottom flask was prepared, equipped with a stirrer and a reflux condenser. Under nitrogen protection, intermediate M-59-1 (1 mmol), 4,4,5,5-tetramethyl-2-(naphtho[2,1-b]benzofuran-2-yl)-1,3,2-dioxaborolane (C-3) (1.2 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL) were sequentially added. The mixture was heated to 90 °C and reacted for 5 h. After the reaction was completed, the mixture was cooled to room temperature, filtered, and suctioned. The filter cake was rinsed twice with deionized water and twice with ethanol. The crude product was further purified twice by recrystallization from o-dichlorobenzene to give organic electroluminescent compound M-58 (yield 71%). Elemental analysis:C 47 H 29 N3. Theoretical value: C,86.61;H,4.49;N,6.45;O, 2.45;Actual value: C,86.53;H,4.59;N,6.41;HRMS(ESI)m / z[M+H] + :Theoretical value: 651.23; Actual value: 652.24.

[0104] Example 25 This example provides an organic electroluminescent compound M-66 in a light-emitting host material, and the synthesis of the organic electroluminescent compound M-66 specifically includes the following steps: TIFF2026504543000045.tif37136

[0105] A 100 mL three-necked round-bottom flask was prepared, equipped with a stirrer and a reflux condenser, and under nitrogen protection, raw material A-66 (1 mmol), 2-([1,1':2',1'-triphenyl]-3-yl)-4,6-dichloro-1,3,5-triazine, i.e., B-5 ​​(1.2 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL) were sequentially added. The mixture was heated to 60 °C and reacted for 5 hours. After completion of the reaction, the temperature was lowered to room temperature, quenched with saturated aqueous ammonium chloride, extracted with ethyl acetate, and the organic phase was dried over anhydrous magnesium sulfate. The solvent was removed using a rotary evaporator, and the crude product was separated by column chromatography (ethyl acetate:n-hexane = 1:50) to obtain intermediate M-66-1 (yield 49%).

[0106] A 100 mL three-necked round-bottom flask was prepared, equipped with a stirrer and a reflux condenser, and under nitrogen protection, intermediate M-66-1 (1 mmol), 4,4,5,5-tetramethyl-2-(naphtho[2,1-b]benzofuran-2-yl)-1,3,2-dioxaborolane (C-1) (1.2 mmol), Pd(dppf)Cl (0.03 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL) were sequentially added. The mixture was heated to 90 °C and reacted for 5 h. After completion of the reaction, the mixture was cooled to room temperature, filtered, and suctioned. The filter cake was rinsed twice with deionized water and twice with ethanol. The crude product was further purified twice by recrystallization from o-dichlorobenzene to obtain compound M-66 (yield 57%). Elemental analysis:C 53 H 33N3O. Theoretical value: C,87.46;H,4.57;N,5.77;O, 2.20;Actual value: C,87.33;H,4.79;N,5.68;HRMS(ESI)m / z[M+H] + :Theoretical value: 727.26; Actual value: 728.24.

[0107] The preparation methods of Examples 26 to 33 are similar to that of Example 22, and specifically, the raw materials used and the obtained products in Examples 26 to 33 are shown in Table 3 below.

[0108] [Table 3] TIFF2026504543000047.tif128163

[0109] Data characterizing the products prepared in Examples 26-33 are presented in Table 4.

[0110] [Table 4]

[0111] Device Example This example provides an organic electroluminescence device. As shown in FIG. 1 , the device includes an anode 2, a hole injection layer 3, a hole transport layer 4, an emitting layer 5, an electron transport layer 6, an electron injection layer 7, and a cathode 8, which are stacked in this order on a substrate 1. The device has a structure of anode (glass substrate with indium tin oxide (ITO) coating) / hole injection layer (HIL) / hole transport layer (HTL) / emitting layer (EML) / electron transport layer (ETL) / electron injection layer (EIL) / cathode (Al).

[0112] The materials used to manufacture the organic electroluminescence device are as follows: TIFF2026504543000049.tif99157

[0113] The preparation method of compound B is the same as that of the benzonaphthofuran-containing oxazole-based organic compound N-1, except that intermediate N1-A is The difference is that the reaction mixture was changed to TIFF2026504543000050.tif1816, and compound B (yield 64%) was obtained. Elemental analysis:C 35 H 22 N2O2; Calculated: C, 83.65; H, 4.41; N, 5.57; O, 6.37; Found: C, 83.62; H, 4.41; N, 5.61; HRMS (ESI) m / z [M+H]+: Calculated: 502.17; Found: 503.32.

[0114] The preparation method of compound C is the same as that of organic electroluminescent compound N-1, except that raw material N1-3 is used. TIFF2026504543000051.tif2222, raw material N1-4 TIFF2026504543000052.tif1124 to obtain compound C (yield 60%). Elemental analysis:C 57 H 35 N3O2; Calculated: C, 86.23; H, 4.44; N, 5.29; O, 4.03; Found: C, 86.28; H, 4.47; N, 5.21; HRMS (ESI) m / z [M+H]+: Calculated: 793.27; Found: 794.25.

[0115] The fabrication of the above organic electroluminescent device includes the following steps:

[0116] 1) Cleaning the substrate A glass substrate coated with transparent ITO was subjected to ultrasonic treatment in an aqueous cleaner (components and concentrations of the aqueous cleaner: ethylene glycol-based solvent ≦10 wt%, triethanolamine ≦1 wt%), then rinsed with deionized water, ultrasonically degreased in a mixed solvent of acetone and ethanol (acetone to ethanol volume ratio 1:1), baked in a clean environment until all moisture was removed, and then cleaned with ultraviolet light and ozone.

[0117] 2) Preparation of the organic layer The ITO transparent substrate was transferred to the deposition equipment and 1 × 10 -6 ~2×10 -4 The system was evacuated to 100 Pa, and a hole injection layer (HIL), hole transport layer (HTL), light emitting layer (EML), electron transport layer (ETL), electron injection layer (EIL), and thick cathode (Al) were sequentially deposited on the anode film.

[0118] where: The material of the hole injection layer (HIL) is a mixture of NDP-9 and HT, and the specific mass ratio is as shown in Table 5. The materials for the hole transport layer (HTL) are listed in Table 5. The light-emitting layer (EML) was vacuum-deposited by co-evaporation. The materials for the light-emitting layer included a host material and a guest material. The guest material was (piq)2Ir(acac). The specific material and the ratio of the host material are shown in Table 5. The materials for the electron transport layer (ETL) are listed in Table 5. The material of the electron injection layer (EIL) is LiQ. The cathode is aluminum.

[0119] Some layers of the organic electroluminescent device and their materials and thicknesses are shown in Table 5.

[0120] [Table 5] TIFF2026504543000054.tif244164 TIFF2026504543000055.tif200164 The examples in the table indicate element examples, and the comparative examples in the table indicate element comparative examples.

[0121] Test Example Among the element examples, the organic electroluminescence elements obtained in element examples 1 to 24 and comparative examples 1 to 6 were tested. Instrumentation: The device characteristics such as current, voltage, brightness, and emission spectrum are tested synchronously using a PR 650 Spectral Scanning Luminance Meter and a Keithley K 2400 Digital Source Meter system. Test conditions: Photoelectric characteristics test conditions: current density is 10mA / cm 2 is. Life test: Current density 50mA / cm 2 The time (in hours) until the brightness of the device decreased to 95% of the original brightness was recorded. The performance test results of the device are shown in Table 6.

[0122] [Table 6] The examples in the table represent element examples, and the comparative examples in the table represent element comparative examples.

[0123] Obviously, the above examples are merely illustrative and do not limit the embodiments. Those skilled in the art can make various other changes or modifications based on the above description. It is not necessary to cover all the embodiments here, and it is impossible to cover all the embodiments. Any obvious changes or variations derived from these fall within the scope of the present invention. [Explanation of symbols]

[0124] 1 board 2 Anode 3. Hole injection layer 4. Hole transport layer 5. Light-emitting layer 6 Electron transport layer 7 Electron injection layer 8 cathode

Claims

1. An oxazole-based organic compound containing benzonaphthofuran, characterized by having a structure represented by the following formula (1): (In the formula (1), ring A is a benzene ring, Ar is selected from a substituted or unsubstituted C6 to C60 aryl group, a substituted or unsubstituted C6 to C60 arylamine group, a substituted or unsubstituted C3 to C60 heteroarylamine group, and a substituted or unsubstituted C3 to C30 heteroaryl group; L is selected from a substituted or unsubstituted C6 to C30 arylene group and a substituted or unsubstituted C3 to C30 heteroarylene group; The substituents in the substituted C6 to C60 aryl group, substituted C6 to C60 arylamine group, substituted C3 to C60 heteroarylamine group, substituted C3 to C30 heteroaryl group, substituted C6 to C30 arylene group, and substituted C3 to C30 heteroarylene group are each independently one or a combination of at least two selected from deuterium, halogen, cyano group, C1 to C12 alkyl group, C3 to C12 cycloalkyl group, C6 to C30 aryl group, C3 to C30 heteroaryl group, C6 to C60 arylamine group, and C3 to C60 heteroarylamine group.

2. Ar is selected from a substituted or unsubstituted C6 to C25 aryl group, a substituted or unsubstituted C6 to C25 arylamine group, a substituted or unsubstituted C3 to C25 heteroarylamine group, and a substituted or unsubstituted C3 to C20 heteroaryl group; wherein the substituents in the substituted C6 to C25 aryl group, the substituted C6 to C25 arylamine group, the substituted C3 to C25 heteroarylamine group, and the substituted C3 to C20 heteroaryl group are each independently one or a combination of at least two selected from deuterium, halogen, cyano group, C1 to C12 alkyl group, C3 to C12 cycloalkyl group, C6 to C30 aryl group, C3 to C30 heteroaryl group, C6 to C60 arylamine group, and C3 to C60 heteroarylamine group; Optionally, Ar is selected from a substituted or unsubstituted B group, wherein B group is selected from a phenyl group, a naphthyl group, a biphenyl group, a phenanthryl group, a fluoranthenyl group, a chrysenyl group, a triphenyl group, a triphenylenyl group, a phenalenyl group, a phenylnaphthyl group, a naphthylphenyl group, a dimethylfluorenyl group, a phenylmethylfluorenyl group, a diphenylfluorenyl group, a pyridyl group, a pyridylphenyl group, a phenylpyridyl group, a spirobifluorenyl group, a benzodimethylfluorenyl group, a benzodiphenylfluorenyl group, a benzospirobifluorenyl group, a dibenzofuryl group, a benzonaphthofuryl group, a benzonaphthothienyl group, a spiro[fluoren-9,9'-xanthene]yl group, a phenylmethylfluorenyl group, a dinaphthofuranyl group, a dinaphthothiophenyl group, a dibenzothiophenyl group, and an N,N-diphenylanilino group; 2. The oxazole-based organic compound containing benzonaphthofuran according to claim 1, wherein the substituent of the substituted group B is one or a combination of at least two selected from the group consisting of deuterium, halogen, cyano, C1 to C12 alkyl, C3 to C12 cycloalkyl, C6 to C30 aryl, C3 to C30 heteroaryl, C6 to C60 arylamine, and C3 to C60 heteroarylamine.

3. 3. The oxazole-based organic compound containing benzonaphthofuran according to claim 1, wherein Ar is selected from the group consisting of a phenyl group, a naphthyl group, a biphenyl group, a chrysenyl group, a phenanthryl group, a triphenyl group, a phenylnaphthyl group, a naphthylphenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a spirobifluorenyl group, a phenalenyl group, a dibenzofuryl group, a benzonaphthofuryl group, and an N,N-diphenylanilino group.

4. L is selected from substituted or unsubstituted C6 to C15 arylene groups, wherein the substituents in the substituted C6 to C15 arylene groups are each independently one or a combination of at least two selected from deuterium, halogen, and C1 to C62 alkyl groups; Optionally, L is selected from a phenylene group, a biphenylene group, and a naphthylene group; 4. The oxazole-based organic compound containing benzonaphthofuran according to claim 1, wherein optionally, L is selected from the group consisting of a phenylene group and a naphthylene group.

5. The oxazole-based organic compound containing benzonaphthofuran according to any one of claims 1 to 4, characterized in that the formula (1) is one selected from the structures represented by the following formulas 1-1 to 1-6. (Here, the definition of Ar is the same as in claim 1.)

6. The oxazole-based organic compound containing benzonaphthofuran according to any one of claims 1 to 5, wherein the oxazole-based organic compound containing benzonaphthofuran is any one selected from the following N-1 to N-208:

7. 7. A light-emitting host material comprising an oxazole-based organic compound containing the benzonaphthofuran according to claim 1.

8. 8. The light-emitting host material according to claim 7, comprising a first host material and a second host material, wherein the first host material is an oxazole-based organic compound containing the benzonaphthofuran according to any one of claims 1 to 6, and the second host material is an organic electroluminescent compound having a structure represented by the following formula (2): (In the formula (2), Ar1 is selected from a substituted or unsubstituted C6 to C60 aryl group and a substituted or unsubstituted C3 to C60 heteroaryl group, Substituents in the substituted C6 to C60 aryl group and substituted C3 to C630 heteroaryl group are each independently one or a combination of at least two selected from deuterium, halogen, cyano group, C1 to C12 alkyl group, C3 to C12 cycloalkyl group, C6 to C30 aryl group, C3 to C30 heteroaryl group, C6 to C60 arylamine group, and C3 to C60 heteroarylamine group; Optionally, Ar1 is selected from a substituted or unsubstituted C6 to C60 non-fused aryl group, a substituted or unsubstituted C3 to C60 non-fused heteroaryl group; the substituents in the substituted C6 to C60 non-fused aryl group and the substituted C3 to C60 non-fused heteroaryl group are each independently one or a combination of at least two selected from the group consisting of deuterium, halogen, cyano group, C1 to C12 alkyl group, C3 to C12 cycloalkyl group, C6 to C30 aryl group, C3 to C30 heteroaryl group, C6 to C60 arylamine group, and C3 to C60 heteroarylamine group; Optionally, Ar1 is selected from a substituted or unsubstituted C6 to C20 non-fused aryl group, a substituted or unsubstituted C3 to C20 non-fused heteroaryl group; the substituents in the substituted C6 to C20 non-fused aryl group and the substituted C3 to C20 non-fused heteroaryl group are each independently one or a combination of at least two selected from the group consisting of deuterium, halogen, cyano group, C1 to C12 alkyl group, C3 to C12 cycloalkyl group, C6 to C30 aryl group, C3 to C30 heteroaryl group, C6 to C60 arylamine group, and C3 to C60 heteroarylamine group; Optionally, Ar1 is selected from a substituted or unsubstituted A group, wherein A group is one selected from a phenyl group, a biphenyl group, and a triphenyl group; wherein the substituents in the substituted A group are selected from deuterium, phenyl, and naphthyl; Optionally, Ar1 is selected from a phenyl group, a biphenyl group, a triphenyl group, and a naphthylphenyl group.

9. the mass ratio of the first host material to the second host material is 9:1 to 1:9; optionally, a weight ratio of the first host material to the second host material is from 2:8 to 8:2; optionally, a weight ratio of the first host material to the second host material is from 3:7 to 7:3; 9. The light-emitting host material of claim 7, further optionally, wherein the weight ratio of the first host material to the second host material is from 4:6 to 6:

4.

10. An organic electroluminescent material comprising an oxazole-based organic compound containing the benzonaphthofuran according to any one of claims 1 to 6 or a light-emitting host material according to any one of claims 7 to 9.

11. a cathode, an anode, and an organic layer located between the cathode and the anode, wherein the organic layer contains the oxazole-based organic compound containing the benzonaphthofuran according to any one of claims 1 to 6, the light-emitting host material according to any one of claims 7 to 9, or the organic electroluminescent material according to claim 10; Optionally, the organic layer comprises one or more of a hole injection layer, a hole transport layer, an emissive layer, an electron transport layer, an electron injection layer; Optionally, the hole transport layer comprises an oxazole-based organic compound containing a benzonaphthofuran according to any one of claims 1 to 6, an emissive host material according to any one of claims 7 to 9, or an organic electroluminescent material according to claim 10; Optionally, the light-emitting layer comprises the oxazole-based organic compound containing the benzonaphthofuran according to any one of claims 1 to 6, the light-emitting host material according to any one of claims 7 to 9, or the organic electroluminescent material according to claim 10. An organic electroluminescent device.

12. Use of the organic electroluminescent device according to claim 11 in an optical fiber device, a lighting device, an electrophotographic photoreceptor device, a photoelectric converter, an organic solar cell, a switching element device, an organic light-emitting field effect transistor, an image sensor, or a dye laser.

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