Benzonaphthofuran-containing oxazole organic compound and use thereof

Abstract

The present application relates to the technical field of display, and in particular to a benzonaphthofuran-containing oxazole organic compound and a use thereof. The benzonaphthofuran-containing oxazole organic compound provided by the present application has a structure as shown below: formula (I). An organic light-emitting device containing the benzonaphthofuran-containing oxazole organic compound can have relatively low driving voltage, relatively high light-emitting efficiency and relatively long service life.

Description

An oxazole organic compound containing benzonaphthofuran and its application

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to the Chinese patent application filed with the Patent Office of China on December 29, 2023, with application number 202311868168.X, and invention name “A kind of oxazole organic compound containing benzonaphthofuran and its application”, and the Chinese patent application filed with the Patent Office of China on March 1, 2024, with application number 202410240330.1, and invention name “A kind of oxazole organic compound containing benzonaphthofuran and its application”, the entire contents of which are incorporated by reference into this application. Technical Field

[0003] The present application relates to the field of display technology, and in particular to an oxazole organic compound containing benzonaphthofuran and its application. Background Art

[0004] Organic electroluminescent device (OLED) is a device that changes electrical energy into light by applying electricity to an organic electroluminescent material, and generally has a structure comprising an anode, a cathode, and an organic layer between the anode and the cathode. The organic layer of the organic EL device can be composed of a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer (which comprises a host material and a doping material), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc., and the materials used for the organic layer are classified into hole injection materials, hole transport materials, electron blocking materials, light-emitting materials, electron buffer materials, hole blocking materials, electron transport materials, electron injection materials, etc. by their functions. In the organic EL device, due to the application of voltage, holes are injected into the light-emitting layer from the anode, and electrons are injected into the light-emitting layer from the cathode, and high-energy excitons are formed by the recombination of holes and electrons. Through this energy, the organic light-emitting compound reaches an excited state, and luminescence is generated by emitting light due to the energy generated by the excited state of the organic light-emitting compound returning to the ground state.

[0005] The most important factor determining the luminous efficiency of organic EL devices is the luminescent material. The luminescent material must have high quantum efficiency and high electron and hole mobility, and the resulting luminescent material layer must be uniform and stable. Luminescent materials are categorized by the color of their emitted light into blue, green, and red, as well as yellow and orange. Furthermore, luminescent materials can be further divided into host materials and dopant materials based on their function.

[0006] However, existing organic electroluminescent materials have low stability, and the HOMO and LUMO energy levels are poorly matched with adjacent energy levels, resulting in an unbalanced carrier mobility. This in turn causes organic electroluminescent devices containing such organic electroluminescent materials to have high driving voltages, low luminous efficiency, and short lifespans, severely limiting their application.

[0007] Summary of the Invention

[0008] The purpose of this application is to overcome the problems of low stability of existing organic electroluminescent materials, poor matching between HOMO and LUMO energy levels and adjacent energy levels, resulting in unbalanced carrier mobility, causing organic electroluminescent devices containing the organic electroluminescent materials to have high driving voltage, low luminous efficiency and short life, and thus provide an oxazole organic compound containing benzonaphthofuran and its application.

[0009] Definitions of substituent terms in this application:

[0010] As used herein, the term "halogen" may include fluorine, chlorine, bromine or iodine.

[0011] As used herein, the term "C1-C30 alkyl" refers to a monovalent substituent derived from a straight-chain or branched saturated hydrocarbon having 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.

[0012] As used herein, the term "C3-C30 cycloalkyl" refers to a cycloalkane derived from a monocyclic hydrocarbon or a polycyclic hydrocarbon having 1 to 30 ring main chain carbon atoms, and the cycloalkane may include cyclopropyl, cyclobutyl, adamantyl, and the like.

[0013] In the present application, aryl and arylene include monocyclic, polycyclic or condensed ring aromatic groups, the rings may be interrupted by short non-aromatic units, and may contain spiro structures. Aryl includes but is not limited to phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, anthracenyl, fluorenyl, spirobifluorenyl, etc., and arylene includes but is not limited to phenylene, biphenylene, terphenylene, naphthylene, phenanthrenyl, anthracenyl, fluorenyl, spirobifluorenyl, etc.

[0014] In the present application, heteroaryl and heteroarylene include monocyclic, polycyclic or condensed ring heteroaryl groups, and the rings may be interrupted by short non-aromatic units, and the heteroatoms include nitrogen, oxygen, and sulfur. Heteroaryl includes, but is not limited to, furyl, phenylthio, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzo thiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, and derivatives thereof; heteroarylene groups include but are not limited to furylene, phenylenethio, pyrroleene, thiophene ... yl, imidazolylene, pyrazolylene, thiazolylene, thiadiazolylene, isothiazolylene, isoxazolylene, oxazolylene, oxadiazolylene, triazinylene, tetrazinylene, triazolylene, tetrazolylene, furazolylene, pyridylene, pyrazinylene, pyrimidylene, pyridazinylene, benzofuranylene, benzothiophenylene, isobenzofuranylene, dibenzofuranylene, dibenzothiophenylene, benzimidazolylene oxazolyl, benzothiazolylene, benzoisothiazolylene, benzoisoxazolylene, benzoxazolylene, isoindolyl, indolyl, indazolylene, benzothiadiazolylene, quinolinylene, isoquinolinylene, cinnolinylene, quinazolinylene, quinoxalinylene, carbazolylene, phenoxazinylene, phenothiazinylene, phenanthridinylene, benzodioxolylene, dihydroacridinylene, and derivatives thereof.

[0015] 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 can be replaced by a substituent. When two or more substituents are present, the two or more substituents may be the same or different.

[0016] As used in this application, unless otherwise specified, hydrogen atoms include protium, deuterium, and tritium.

[0017] In the present application, the definition of a group defines the range of the number of carbon atoms, and the number of carbon atoms is any integer within the defined range. For example, a C6-C30 aromatic group represents an aromatic group, and the number of carbon atoms can be any integer within the range of 6-60, such as 6, 8, 10, 13, 15, 17, 20, 22, 25 or 30.

[0018] In this application, Indicates a connection key.

[0019] The scheme adopted in this application is as follows:

[0020] The present application provides an oxazole organic compound containing benzonaphthofuran, having a structure shown in the following formula (1):

[0021] In the formula (1), ring A is a benzene ring;

[0022] Ar is selected from a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 arylamine group, a substituted or unsubstituted C3-C60 heteroarylamine group, or a substituted or unsubstituted C3-C30 heteroaryl group;

[0023] L is selected from a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C30 heteroarylene group;

[0024] The substituents in the substituted C6-C60 aryl group, substituted C6-C60 arylamine group, substituted C3-C60 heteroarylamine group, substituted C3-C30 heteroaryl group, substituted C6-C30 arylene group, and substituted C3-C30 heteroarylene group are each independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl group, C3-C12 cycloalkyl group, C6-C30 aryl group, C3-C30 heteroaryl group, C6-C60 arylamine group, and C3-C60 heteroarylamine group.

[0025] Understandably, Ring A in formula (1) can be fused to ring C through positions 1, 2; 2, 3; 3, 4; N can be directly connected to any substitutable position in ring A, ring C, and ring D; L can be connected to any substitutable position in ring B.

[0026] Optionally, Ar is selected from substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C6-C25 arylamine, substituted or unsubstituted C3-C25 heteroarylamine, substituted or unsubstituted C3-C20 heteroaryl;

[0027] wherein the substituents in the substituted C6-C25 aryl group, the substituted C6-C25 arylamine group, the substituted C3-C25 heteroarylamine group, and the substituted C3-C20 heteroaryl group are each independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl group, C3-C12 cycloalkyl group, C6-C30 aryl group, C3-C30 heteroaryl group, C6-C60 arylamine group, and C3-C60 heteroarylamine group;

[0028] Optionally, Ar is selected from a substituted or unsubstituted B group, and the B group is selected from the following groups: phenyl, naphthyl, biphenyl, phenanthrenyl, fluoranthene, phenyl, terphenyl, triphenylene, phenalenyl, phenylnaphthyl, naphthylphenyl, dimethylfluorenyl, phenylmethylfluorenyl, diphenylfluorenyl, pyridyl, pyridylphenyl, phenylpyridyl, spirobifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirobifluorenyl, dibenzofuranyl, benzonaphthofuranyl, benzonaphthothienyl, spiro[fluorene-9,9'-xanthenyl]yl, phenylmethylfluorenyl, dinaphthofuranyl, dinaphthothienyl, dibenzothienyl, N,N-diphenylanilinoyl;

[0029] wherein the substituent of the substituted B group is selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine;

[0030] Optionally, Ar is selected from phenyl, naphthyl, biphenyl, phenyl, phenanthrenyl, terphenyl, phenylnaphthyl, naphthylphenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, phenanthrenyl, dibenzofuranyl, benzonaphthofuranyl, N,N-diphenylanilino.

[0031] 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 selected from one or a combination of at least two of deuterium, halogen, and C1-C62 alkyl;

[0032] Optionally, L is selected from phenylene, biphenylene, and naphthylene;

[0033] Optionally, L is selected from phenylene and naphthylene.

[0034] Optionally, the formula (1) is selected from one of the structures shown in the following formulas 1-1 to 1-6:

[0035] Wherein, Ar is as defined above.

[0036] Optionally, the formula (1) is selected from one of the structures shown in the following formulas 1-7 to 1-12:

[0037] Wherein, Ar is as defined above.

[0038] Optionally, the oxazole organic compound containing benzonaphthofuran is selected from any one of the following N-1 to N-208:

[0039] The present application provides a light-emitting host material, including the above-mentioned oxazole organic compound containing benzonaphthofuran.

[0040] Optionally, the light-emitting host material includes a first host material and a second host material, wherein the first host material is the above-mentioned oxazole organic compound containing benzonaphthofuran; and the second host material is an organic electroluminescent compound having the following structure (2):

[0041] In the formula (2), Ar1 is selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;

[0042] The substituents in the substituted C6-C60 aryl group and the substituted C3-C630 heteroaryl group are each independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 aromatic amine, and C3-C60 heteroaromatic amine groups.

[0043] 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;

[0044] The substituents in the substituted C6-C60 non-fused aromatic group and the substituted C3-C60 non-fused heteroaromatic group are each independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aromatic group, C3-C30 heteroaromatic group, C6-C60 aromatic amine group, and C3-C60 heteroaromatic amine group.

[0045] Optionally, Ar1 is selected from substituted or unsubstituted C6-C20 non-fused aryl, substituted or unsubstituted C3-C20 non-fused heteroaryl;

[0046] The substituents in the substituted C6-C20 non-fused aryl group and the substituted C3-C20 non-fused heteroaryl group are each independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 aromatic amine, and C3-C60 heteroaromatic amine groups.

[0047] Optionally, Ar1 is selected from a substituted or unsubstituted A group, and the A group is selected from one of the following groups: phenyl, biphenyl, terphenyl;

[0048] wherein the substituent in the substituted A group is selected from deuterium, phenyl, and naphthyl;

[0049] Optionally, Ar1 is selected from phenyl, biphenyl, terphenyl, and naphthylphenyl.

[0050] Optionally, the organic electroluminescent compound having the structure of the following formula (2) is selected from any one of the following M-1 to M-104:

[0051] Optionally, the mass ratio of the first main material to the second main material is 9:1-1:9;

[0052] Optionally, the mass ratio of the first main material to the second main material is 2:8-8:2;

[0053] Optionally, the mass ratio of the first main material to the second main material is 3:7-7:3;

[0054] Further optionally, the mass ratio of the first main material to the second main material is 4:6-6:4.

[0055] The present application also provides an organic electroluminescent material, including the above-mentioned oxazole organic compound containing benzonaphthofuran or the above-mentioned luminescent host material.

[0056] The present application provides an organic electroluminescent device, comprising a cathode, an anode, and an organic layer located between the cathode and the anode, wherein the organic layer comprises the above-mentioned oxazole organic compound containing benzonaphthofuran or the above-mentioned luminescent host material or the above-mentioned organic electroluminescent material;

[0057] Optionally, the organic layer comprises one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

[0058] Optionally, the hole transport layer comprises the aforementioned oxazole organic compound containing benzonaphthofuran or the aforementioned luminescent host material or the aforementioned organic electroluminescent material;

[0059] Optionally, the light-emitting layer comprises the above-mentioned oxazole organic compound containing benzonaphthofuran or the above-mentioned light-emitting host material or the above-mentioned organic electroluminescent material.

[0060] The present application provides applications of the above-mentioned organic electroluminescent device in optical fiber equipment, lighting equipment, electronic photographic photoreceptor equipment, photoelectric converters, organic solar cells, switching element equipment, organic light-emitting field-effect transistors, image sensors or dye lasers.

[0061] Beneficial effects of this application:

[0062] The oxazole organic compound containing benzonaphthofuran provided in the present application is based on the structure of formula (1), and further limiting the types of substituents can improve the structural stability of the compound. In addition, the HOMO and LUMO energy levels of the oxazole organic compound containing benzonaphthofuran have a high degree of matching with adjacent energy levels, so that the carrier mobility of the oxazole organic compound containing benzonaphthofuran is relatively balanced, thereby enabling the organic electroluminescent device containing the oxazole organic compound containing benzonaphthofuran to have a low driving voltage, high luminous efficiency and long life.

[0063] Furthermore, the oxazole organic compound containing benzonaphthofuran provided in the present application has good electron transport properties and can be used as an electron transport material or a luminescent material;

[0064] Furthermore, the present application provides an organic electroluminescent material comprising an oxazole organic compound containing benzonaphthofuran based on the structure of formula (1), thereby enabling an organic electroluminescent device comprising the organic electroluminescent material to have a lower driving voltage, higher luminous efficiency and longer life. BRIEF DESCRIPTION OF THE DRAWINGS

[0065] In order to more clearly illustrate the specific implementation methods of the present application or the technical solutions in the prior art, the following is a brief introduction to the drawings required for use in the specific implementation methods or the description of the prior art. Obviously, the drawings described below are some implementation methods of the present application. For ordinary technicians in this field, other drawings can be obtained based on these drawings without any creative work.

[0066] FIG1 is a structural diagram of an organic electroluminescent device in an embodiment of the device of the present application;

[0067] 1-substrate; 2-anode; 3-hole injection layer; 4-hole transport layer; 5-light-emitting layer; 6-electron transport layer; 7-electron injection layer; 8-cathode. DETAILED DESCRIPTION

[0068] The following examples are provided to further better understand the present application, but are not limited to the best implementation mode described herein, and do not limit the content and protection scope of the present application. Any product identical or similar to the present application obtained by anyone under the inspiration of the present application or by combining the features of the present application with other prior arts shall fall within the scope of protection of the present application.

[0069] If no specific experimental steps or conditions are specified in the examples, the conventional experimental steps or conditions described in the literature in this field can be used. If the manufacturer of the reagents or instruments is not specified, they are all commercially available conventional reagents.

[0070] The term "organic electroluminescent material" in the present disclosure means a material that can be used in an organic electroluminescent device and can include at least one compound. If necessary, the organic electroluminescent material can be included in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, a hole assist material, a luminescence assist material, an electron blocking material, a luminescent material (containing a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.

[0071] The term "multiple organic electroluminescent materials" in the present disclosure means one or more organic electroluminescent materials comprising a combination of at least two compounds, which may be included in any layer constituting the organic electroluminescent device. It may mean both a material before being included in the organic electroluminescent device (for example, before vapor deposition) and a material after being included in the organic electroluminescent device (for example, after vapor deposition). For example, a plurality of organic electroluminescent materials may be a combination of at least two compounds, which may be included in at least one of the following: a hole injection layer, a hole transport layer, a hole auxiliary layer, a luminescence auxiliary layer, an electron blocking layer, a luminescent layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. At least two compounds may be included in the same layer or different layers and may be mixed.

[0072] In the present application, the benzonaphthofuran-containing oxazole organic compound having the structure of formula (1) is prepared by the following synthetic route:

[0073] 1. Synthesis of intermediate Nn-A: The reaction materials Nn-1 and Nn-2 were subjected to Suzuki cross-coupling reaction, and the reaction formula is as follows:

[0074] 2. Synthesis of compound Nn: Buchwald reaction of intermediates Nn-A and Nn-B Cross-coupling reaction, the reaction formula is as follows:

[0075] In the present application, the compound represented by the structure of formula (2) is prepared by the following synthetic route:

[0076] The intermediate raw materials An, Bn, and Cn can be purchased directly or synthesized by conventional reaction pathways and conditions according to methods reported in existing literature.

[0077] The specific structures of the intermediate raw materials used in the examples provided in this application are as follows:

[0078] The specific structure of Bn is:

[0079] The specific structure of Cn is:

[0080] Example 1

[0081] This embodiment provides an oxazole organic compound N-1 containing benzonaphthofuran. The synthesis of the oxazole organic compound N-1 containing benzonaphthofuran specifically includes the following steps:

[0082] Synthesis of intermediate N1-A

[0083] After nitrogen replacement to a three-mouth reaction flask equipped with mechanical stirring, a thermometer, and a condenser tube, raw material 10g N1-1 (36.63mmol), 5.72g N1-2 (36.63mmol), 0.85g tetrakis triphenylphosphine palladium (0.73mmol), 10.11g potassium carbonate (73.27mmol), 70mL toluene, 30mL ethanol, and 30mL water were added sequentially. The mixture was stirred at 65°C for 2 hours. After the reaction was complete, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 10.06g of compound N1-A (yield 90%).

[0084] Synthesis of intermediate N1-B

[0085] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, intermediate 10 g N1-A (32.78 mmol), 3.1 g N1-3 (32.78 mmol), 0.6 g tris (dibenzylideneacetone) dipalladium (0.66 mmol), 0.67 g 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.64 mmol), 6.3 g sodium tert-butoxide (65.56 mmol), 100 mL of toluene were added sequentially, and the mixture was stirred at reflux for 3 hours at 110 ° C. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried and purified by column chromatography to obtain 8.31 g of compound N1-B (yield 82%).

[0086] Synthesis of compound N-1

[0087] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, intermediate 8.30 g N1-B (26.85 mmol), 7.95 g N1-4 (26.85 mmol), 0.49 g tris (dibenzylideneacetone) dipalladium (0.54 mmol), 0.55 g 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.34 mmol), 5.16 g sodium tert-butoxide (53.70 mmol), 100 mL of toluene were added sequentially, and the mixture was stirred at reflux for 3 hours at 110 ° C. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried and purified by column chromatography to obtain 11.80 g of oxazole organic compound N-1 containing benzonaphthofuran (yield 76%).

[0088] Elemental analysis: C 41 H 26 N2O2; theoretical value: C, 85.10; H, 4.53; N, 4.84; O, 5.53; found value: C, 85.12; H, 4.52; N, 4.83; HRMS (ESI) m / z [M+H] +: theoretical value: 578.20; found value: 579.21.

[0089] Example 2

[0090] This embodiment provides an oxazole organic compound N-6 containing benzonaphthofuran. The synthesis of the oxazole organic compound N-6 containing benzonaphthofuran specifically includes the following steps:

[0091] After nitrogen replacement of a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, intermediate 10 g N1-A (32.78 mmol), 10.92 g N6-3 (32.78 mmol), 0.6 g tris (dibenzylideneacetone) dipalladium (0.66 mmol), 0.67 g 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.64 mmol), 6.3 g sodium tert-butoxide (65.56 mmol), 100 mL of toluene were added sequentially, and the mixture was stirred at reflux for 3 hours at 110 ° C. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried and purified by column chromatography to obtain 14.41 g of compound N6-B (yield 73%).

[0092] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, 10 g of intermediate N6-B (16.60 mmol), 4.91 g of N1-4 (16.60 mmol), 0.30 g of tris (dibenzylideneacetone) dipalladium (0.33 mmol), 0.34 g of 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (0.83 mmol), 3.19 g of sodium tert-butoxide (33.21 mmol), and 100 mL of toluene were added sequentially, and the mixture was stirred under reflux at 110 ° C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 9.24 g of oxazole organic compound N-6 containing benzonaphthofuran (yield 68%).

[0093] Elemental analysis: C 60 H 38 N2O2; theoretical value: C, 88.00; H, 4.68; N, 3.42; O, 3.91; found value: C, 88.01; H, 4.68; N, 3.41; HRMS (ESI) m / z [M+H]+: theoretical value: 818.29; found value: 819.28.

[0094] Example 3

[0095] This embodiment provides an oxazole organic compound N-18 containing benzonaphthofuran. The synthesis of the oxazole organic compound N-18 containing benzonaphthofuran specifically includes the following steps:

[0096] After nitrogen replacement of a three-necked reaction flask equipped with mechanical stirring, a thermometer, and a condenser, intermediate 10 g N1-A (32.78 mmol), 8.53 g N18-3 (32.78 mmol), 0.60 g tris (dibenzylideneacetone) dipalladium (0.66 mmol), 0.67 g 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.64 mmol), 6.3 g sodium tert-butoxide (65.56 mmol), 100 mL of toluene were added sequentially, and the mixture was refluxed at 110 ° C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried and purified by column chromatography to obtain 13.19 g of compound N18-B (yield 76%).

[0097] After nitrogen replacement of a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, 10 g of N18-B (18.90 mmol), 5.59 g of N18-4 (18.90 mmol), 0.35 g of tris (dibenzylideneacetone) dipalladium (0.38 mmol), 0.39 g of 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (0.94 mmol), 3.63 g of sodium tert-butoxide (37.79 mmol), and 100 mL of toluene were added sequentially, and the mixture was stirred at reflux for 3 hours at 110 ° C. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 10.70 g of organic electroluminescent compound N-18 (yield 76%).

[0098] Elemental analysis: C 53 H 35 N3O2; theoretical value: C, 85.35; H, 4.73; N, 5.63; O, 4.29; found value: C, 85.37; H, 4.72; N, 5.62; HRMS (ESI) m / z [M+H] +: theoretical value: 745.27; found value: 746.26.

[0099] Example 4

[0100] This embodiment provides an oxazole organic compound N-30 containing benzonaphthofuran. The synthesis of the oxazole organic compound N-30 containing benzonaphthofuran specifically includes the following steps:

[0101] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, intermediate 10 g N1-A (32.78 mmol), 5.54 g N30-3 (32.78 mmol), 0.60 g tris (dibenzylideneacetone) dipalladium (0.66 mmol), 0.67 g 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.64 mmol), 6.30 g sodium tert-butoxide (65.56 mmol), 100 mL of toluene were added sequentially, and the mixture was stirred at reflux for 3 hours at 110 ° C. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried and purified by column chromatography to obtain 11.49 g of compound N30-B (yield 80%).

[0102] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, 10 g of intermediate N30-B (22.82 mmol), 6.75 g of N30-4 (22.82 mmol), 0.42 g of tris (dibenzylideneacetone) dipalladium (0.46 mmol), 0.47 g of 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.14 mmol), 4.39 g of sodium tert-butoxide (45.64 mmol), and 100 mL of toluene were added sequentially, and the mixture was refluxed at 110 ° C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 10.75 g of oxazole organic compound N-30 containing benzonaphthofuran (yield 72%).

[0103] Elemental analysis: C 47 H 30 N2O2; theoretical value: C, 86.22; H, 4.62; N, 4.28; O, 4.89; found value: C, 86.20; H, 4.63; N, 4.29; HRMS (ESI) m / z [M+H] +: theoretical value: 654.23; found value: 654.24.

[0104] Example 5

[0105] This embodiment provides an oxazole organic compound N-45 containing benzonaphthofuran. The synthesis of the oxazole organic compound N-45 containing benzonaphthofuran specifically includes the following steps:

[0106] After nitrogen substitution to a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, intermediate 10 g N1-A (32.78 mmol), 7.18 g N45-3 (32.78 mmol), 0.60 g tris (dibenzylideneacetone) dipalladium (0.66 mmol), 0.67 g 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.64 mmol), 6.30 g sodium tert-butoxide (65.56 mmol), 100 mL of toluene were added sequentially, and the mixture was stirred at reflux for 3 hours at 110 ° C. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried and purified by column chromatography to obtain 12.16 g of compound N45-B (yield 76%).

[0107] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, 7.50 g of intermediate N45-B (15.36 mmol), 3.87 g of N45-4 (15.36 mmol), 0.28 g of tris (dibenzylideneacetone) dipalladium (0.31 mmol), 0.31 g of 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (0.77 mmol), 2.95 g of sodium tert-butoxide (30.73 mmol), and 80 mL of toluene were added sequentially, and the mixture was refluxed at 110 ° C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 8.22 g of benzonaphthofuran-containing oxazole organic compound N-45 (yield 76%).

[0108] Elemental analysis: C 51 H 32 N2O2; theoretical value: C, 86.91; H, 4.58; N, 3.97; O, 4.54; found value: C, 86.93; H, 4.57; N, 3.96; HRMS (ESI) m / z [M+H] +: theoretical value: 704.25; found value: 705.26.

[0109] Example 6

[0110] This embodiment provides an oxazole organic compound N-72 containing benzonaphthofuran. The synthesis of the oxazole organic compound N-72 containing benzonaphthofuran specifically includes the following steps:

[0111] Synthesis of intermediate N72-A

[0112] After nitrogen replacement to a three-mouth reaction flask equipped with mechanical stirring, a thermometer, and a condenser tube, raw material 10g N1-1 (36.63mmol), 5.72g N72-2 (36.63mmol), 0.85g tetrakis triphenylphosphine palladium (0.73mmol), 10.11g potassium carbonate (73.27mmol), 70mL toluene, 30mL ethanol, and 30mL water were added sequentially. The mixture was stirred at 65°C for 2 hours. After the reaction was complete, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 9.50g of compound N72-A (yield 85%).

[0113] Synthesis of intermediate N72-B

[0114] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, 9.50 g of intermediate N72-A (31.14 mmol), 6.82 g of N73-3 (31.14 mmol), 0.57 g of tris (dibenzylideneacetone) palladium (0.62 mmol), 0.64 g of 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.56 mmol), 5.99 g of sodium tert-butoxide (62.28 mmol), and 100 mL of toluene were added sequentially, and the mixture was refluxed at 110 ° C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 11.10 g of compound N72-B (yield 73%).

[0115] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, 10 g of intermediate N72-B (20.48 mmol), 6.06 g of N72-4 (20.48 mmol), 0.37 g of tris (dibenzylideneacetone) dipalladium (0.41 mmol), 0.42 g of 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.02 mmol), 3.94 g of sodium tert-butoxide (40.97 mmol), and 100 mL of toluene were added sequentially, and the mixture was refluxed at 110 ° C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 10.82 g of oxazole organic compound N-72 containing benzonaphthofuran (yield 75%).

[0116] Elemental analysis: C51H32N2O2; theoretical value: C, 86.91; H, 4.58; N, 3.97; O, 4.54; found value: C, 86.93; H, 4.57; N, 3.96; HRMS (ESI) m / z [M+H]+: theoretical value: 704.25; found value: 705.26.

[0117] Example 7

[0118] This embodiment provides an oxazole organic compound N-95 containing benzonaphthofuran. The synthesis of the oxazole organic compound N-95 containing benzonaphthofuran specifically includes the following steps:

[0119] After nitrogen replacement to a three-mouth reaction flask equipped with mechanical stirring, a thermometer, and a condenser, raw material 10g N1-1 (36.63mmol), 5.72g N95-2 (36.63mmol), 0.85g tetrakis triphenylphosphine palladium (0.73mmol), 10.11g potassium carbonate (73.27mmol), 70mL toluene, 30mL ethanol, and 30mL water were added sequentially. The mixture was stirred at 65 ° C for 2 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried and purified by column chromatography to obtain 9.28g of compound N95-A (yield 83%).

[0120] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, 9.28 g of intermediate N95-A (30.42 mmol), 6.67 g of N72-3 (30.42 mmol), 0.56 g of tris (dibenzylideneacetone) palladium (0.61 mmol), 0.62 g of 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.52 mmol), 5.85 g of sodium tert-butoxide (60.84 mmol), and 100 mL of toluene were added sequentially, and the mixture was refluxed at 110 ° C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 10.69 g of compound N95-B (yield 72%).

[0121] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, 10 g of intermediate N95-B (20.48 mmol), 6.06 g of N95-4 (20.48 mmol), 0.37 g of tris (dibenzylideneacetone) dipalladium (0.41 mmol), 0.42 g of 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.02 mmol), 3.94 g of sodium tert-butoxide (40.97 mmol), and 100 mL of toluene were added sequentially, and the mixture was refluxed at 110 ° C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 10.10 g of benzonaphthofuran-containing oxazole organic compound N-95 (yield 70%).

[0122] Elemental analysis: C 51 H 32 N2O2; theoretical value: C, 86.91; H, 4.58; N, 3.97; O, 4.54; found value: C, 86.90; H, 4.58; N, 3.98; HRMS (ESI) m / z [M+H] +: theoretical value: 704.25; found value: 705.26.

[0123] Example 8

[0124] This embodiment provides an oxazole organic compound N-134 containing benzonaphthofuran. The synthesis of the oxazole organic compound N-134 containing benzonaphthofuran specifically includes the following steps:

[0125] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, 8.60 g of intermediate N18-B (16.25 mmol), 4.10 g of N134-4 (16.25 mmol), 0.30 g of tris (dibenzylideneacetone) dipalladium (0.33 mmol), 0.33 g of 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (0.81 mmol), 3.12 g of sodium tert-butoxide (32.50 mmol), and 100 mL of toluene were added sequentially, and the mixture was refluxed at 110 ° C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 9.20 g of benzonaphthofuran-containing oxazole organic compound N-134 (yield 76%).

[0126] Elemental analysis: C 53 H 35N3O2; theoretical value: C, 85.35; H, 4.73; N, 5.63; O, 4.29; found value: C, 85.33; H, 4.74; N, 5.64; HRMS (ESI) m / z [M+H] +: theoretical value: 745.27; found value: 746.29.

[0127] Example 9

[0128] This embodiment provides an oxazole organic compound N-148 containing benzonaphthofuran. The synthesis of the oxazole organic compound N-148 containing benzonaphthofuran specifically includes the following steps:

[0129] After nitrogen substitution to a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, intermediate 10 g N73-A (32.78 mmol), 5.54 g N30-3 (32.78 mmol), 0.60 g tris (dibenzylideneacetone) dipalladium (0.66 mmol), 0.67 g 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.64 mmol), 6.3 g sodium tert-butoxide (65.56 mmol), 100 mL of toluene were added sequentially, and the mixture was stirred at reflux for 3 hours at 110 ° C. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 11.34 g of compound N148-B (yield 79%).

[0130] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, 10 g of intermediate N148-B (22.82 mmol), 6.57 g of N18-4 (22.82 mmol), 0.42 g of tris (dibenzylideneacetone) dipalladium (0.46 mmol), 0.47 g of 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.14 mmol), 4.39 g of sodium tert-butoxide (45.64 mmol), and 100 mL of toluene were added sequentially, and the mixture was refluxed at 110 ° C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 11.20 g of benzonaphthofuran-containing oxazole organic compound N-148 (yield 75%).

[0131] Elemental analysis: C 47 H 30N2O2; theoretical value: C, 86.22; H, 4.62; N, 4.28; O, 4.89; found value: C, 86.22; H, 4.62; N, 4.28; HRMS (ESI) m / z [M+H] +: theoretical value: 654.23; found value: 655.21.

[0132] Example 10

[0133] This embodiment provides an organic electroluminescent compound N-173. The synthesis of the organic electroluminescent compound N-173 specifically includes the following steps:

[0134] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, intermediate 10 g N73-A (32.78 mmol), 4.69 g N173-3 (32.78 mmol), 0.60 g tris (dibenzylideneacetone) dipalladium (0.66 mmol), 0.67 g 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.64 mmol), 6.30 g sodium tert-butoxide (65.56 mmol), 100 mL of toluene were added sequentially, and the mixture was stirred at reflux for 3 hours at 110 ° C. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 9.73 g of compound N173-B (yield 72%).

[0135] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, 9.70 g of intermediate N173-B (23.53 mmol), 6.97 g of N173-4 (23.53 mmol), 0.43 g of tris (dibenzylideneacetone) dipalladium (0.47 mmol), 0.48 g of 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.18 mmol), 4.52 g of sodium tert-butoxide (47.07 mmol), and 100 mL of toluene were added sequentially, and the mixture was refluxed at 110 ° C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 10.35 g of compound N-173 (yield 70%).

[0136] Elemental analysis: C 45 H 28 N2O2; theoretical value: C, 85.97; H, 4.49; N, 4.46; O, 5.09; found value: C, 85.96; H, 4.48; N, 4.48; HRMS (ESI) m / z [M+H] +: theoretical value: 628.22; found value: 629.24.

[0137] Example 11

[0138] This embodiment provides an organic electroluminescent compound N-182. The synthesis of the organic electroluminescent compound N-182 specifically includes the following steps:

[0139] After nitrogen replacement to a three-mouth reaction flask equipped with mechanical stirring, a thermometer, and a condenser tube, raw material 10g N182-1 (36.63mmol), 5.72g N182-2 (36.63mmol), 0.85g tetrakis triphenylphosphine palladium (0.73mmol), 10.11g potassium carbonate (73.27mmol), 70mL toluene, 30mL ethanol, and 30mL water were added sequentially. The mixture was stirred at 65°C for 2 hours. After the reaction was complete, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 8.94g of compound N182-A (80% yield).

[0140] After nitrogen replacement of a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, intermediate 8.94g N182-A (29.31mmol), 4.96g N30-3 (29.31mmol), 0.54g tris (dibenzylideneacetone) palladium (0.59mmol), 0.60g 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.47mmol), 5.63g sodium tert-butoxide (58.61mmol), 100mL of toluene were added sequentially, and the mixture was refluxed at 110°C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried and purified by column chromatography to obtain 10.01g of compound N182-B (yield 78%).

[0141] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, 10.01 g of intermediate N182-B (22.85 mmol), 6.76 g of N1-4 (22.85 mmol), 0.42 g of tris (dibenzylideneacetone) dipalladium (0.46 mmol), 0.47 g of 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.14 mmol), 4.39 g of sodium tert-butoxide (45.69 mmol), and 100 mL of toluene were added sequentially, and the mixture was refluxed at 110 ° C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 11.21 g of compound N-182 (yield 75%).

[0142] Elemental analysis: C 47 H 30 N2O2; theoretical value: C, 86.22; H, 4.62; N, 4.28; O, 4.89; found value: C, 86.24; H, 4.61; N, 4.27; HRMS (ESI) m / z [M+H] +: theoretical value: 654.23; found value: 654.21.

[0143] Example 12

[0144] After nitrogen replacement of a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, intermediate 8.94 g N182-A (29.31 mmol), 4.96 g N173-3 (29.31 mmol), 0.54 g tris (dibenzylideneacetone) dipalladium (0.59 mmol), 0.60 g 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.47 mmol), 5.63 g sodium tert-butoxide (58.61 mmol), 100 mL of toluene were added sequentially, and the mixture was refluxed at 110 ° C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried and purified by column chromatography to obtain 10.01 g of compound N207-B (yield 78%).

[0145] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a condenser, 10 g of intermediate N207-B (24.26 mmol), 7.18 g of N72-4 (24.26 mmol), 0.44 g of tris (dibenzylideneacetone) dipalladium (0.49 mmol), 0.50 g of 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.21 mmol), 4.66 g of sodium tert-butoxide (48.52 mmol), and 100 mL of toluene were added sequentially, and the mixture was refluxed at 110 ° C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 10.97 g of compound N-207 (yield 72%).

[0146] Elemental analysis: C 45 H 28 N2O2; theoretical value: C, 85.97; H, 4.49; N, 4.46; O, 5.09; found value: C, 85.95; H, 4.49; N, 4.48; HRMS (ESI) m / z [M+H] +: theoretical value: 628.22; found value: 628.21.

[0147] The preparation methods of Examples 13-21 are similar to those of Example 1. Specifically, the raw materials used in Examples 13-21 and the products obtained are shown in Table 1 below.

[0148] Table 1

[0149] The characterization data of the products prepared in Examples 13-21 are shown in Table 2:

[0150] Table 2

[0151] Example 22

[0152] This embodiment provides an organic electroluminescent compound M-3 in a luminescent host material. The synthesis of the organic electroluminescent compound M-3 specifically includes the following steps:

[0153] Take a 100 ml three-necked round-bottom flask and place a stirring bar and a reflux tube on it. Under nitrogen protection, add raw material A-3 (1 mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine (1.2 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), 1,4-dioxane / water (10 mL / 2 mL) in sequence, heat to 60 degrees Celsius and react for 5 hours. After the reaction, cool to room temperature, quench with saturated ammonium chloride aqueous solution, extract with ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, use a rotary evaporator to remove the solvent, and separate the crude product by column chromatography (ethyl acetate: n-hexane = 1:50) to obtain intermediate M-3-1 (yield 61%).

[0154] Take a 100 ml three-necked round-bottom flask and place a stirring bar and a reflux tube on it. Under nitrogen protection, add the intermediate M-3-1 (1 mmol), 4,4,5,5-tetramethyl-2-(naphtho[2,1-b]benzofuran-1-yl)-1,3,2-dioxaborolane, i.e. C-1 (1.2 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), 1,4-dioxane / water (10 mL / 2 mL) in sequence, heat to 90 degrees Celsius and react for 5 hours. After the reaction is completed, cool to room temperature, filter, rinse the filter cake twice with deionized water and twice with ethanol, and then recrystallize and purify the crude product twice with o-dichlorobenzene to obtain the organic electroluminescent compound M-3 (yield 42%).

[0155] Elemental analysis: C 41 H 25N3. Calculated: C, 85.54; H, 4.38; N, 7.30; O, 2.78; Found: C, 85.48; H, 4.50; N, 7.24; HRMS (ESI) m / z [M+H] + : Theoretical value: 575.20; measured value: 576.20.

[0156] Example 23

[0157] This embodiment provides an organic electroluminescent compound M-54 in a luminescent host material. The synthesis of the organic electroluminescent compound M-54 specifically includes the following steps:

[0158] Take a 100 ml three-necked round-bottom flask and place a stirring bar and a reflux tube on it. Under nitrogen protection, add raw material A-54 (1 mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine (1.2 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), 1,4-dioxane / water (10 mL / 2 mL) in sequence, heat to 60 degrees Celsius and react for 5 hours. After the reaction, cool to room temperature and quench with saturated ammonium chloride aqueous solution. Extract with ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, remove the solvent using a rotary evaporator, and separate the crude product by column chromatography (ethyl acetate: n-hexane = 1:50) to obtain intermediate M-54-1 (yield 45%).

[0159] A 100 ml three-necked round-bottom flask was placed with a stirring bar and a reflux tube connected to the top. Under nitrogen protection, the intermediate M-54-1 (1 mmol), 4,4,5,5-tetramethyl-2-(naphtho[2,1-b]benzofuran-5-yl)-1,3,2-dioxaborolane, i.e. C-4 (1.2 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), 1,4-dioxane / water (10 mL / 2 mL) were added in sequence. The temperature was raised to 90 degrees Celsius for 5 hours. After the reaction, the temperature was lowered to room temperature, filtered, and the filter cake was rinsed twice with deionized water and twice with ethanol. The crude product was then purified twice by recrystallization from o-dichlorobenzene to obtain the organic electroluminescent compound 54 (yield 46%).

[0160] Elemental analysis: C 41 H 25 N3. Calculated: C, 85.54; H, 4.38; N, 7.30; O, 2.78; Found: C, 85.44; H, 4.54; N, 7.24; HRMS (ESI) m / z [M+H] + : Theoretical value: 575.20; measured value: 576.20.

[0161] Example 24

[0162] This embodiment provides an organic electroluminescent compound M-58 in a luminescent host material. The synthesis of the organic electroluminescent compound M-58 specifically includes the following steps:

[0163] A 100 ml three-necked round-bottom flask was placed with a stirring bar and a reflux tube connected to the top. 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), 1,4-dioxane / water (10 mL / 2 mL) were added in sequence. The temperature was raised to 60 degrees Celsius and the reaction was carried out for 5 hours. After the reaction, the temperature was lowered to room temperature and the reaction was quenched with saturated aqueous ammonium chloride solution. The reaction was extracted with ethyl acetate, and the organic phase was dried over anhydrous magnesium sulfate. 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-59-1 (yield 54%).

[0164] Take a 100 ml three-necked round-bottom flask and place a stirring bar and a reflux tube on it. Under nitrogen protection, add the intermediate M-59-1 (1 mmol), 4,4,5,5-tetramethyl-2-(naphtho[2,1-b]benzofuran-2-yl)-1,3,2-dioxaborolane, i.e. C-3 (1.2 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), 1,4-dioxane / water (10 mL / 2 mL) in sequence, heat to 90 degrees Celsius and react for 5 hours. After the reaction is completed, cool to room temperature, filter, rinse the filter cake twice with deionized water and twice with ethanol, and then recrystallize and purify the crude product twice with o-dichlorobenzene to obtain the organic electroluminescent compound M-58 (yield 71%).

[0165] Elemental analysis: C 47 H 29 N3. Calculated: C, 86.61; H, 4.49; N, 6.45; O, 2.45; Found: C, 86.53; H, 4.59; N, 6.41; HRMS (ESI) m / z [M+H] + : Theoretical value: 651.23; measured value: 652.24.

[0166] Example 25

[0167] This embodiment provides an organic electroluminescent compound M-66 in a luminescent host material. The synthesis of the organic electroluminescent compound M-66 specifically includes the following steps:

[0168] A 100 ml three-necked round-bottom flask was placed with a stirring bar and a reflux tube connected to the top. 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), 1,4-dioxane / water (10 mL / 2 mL) were added in sequence. The temperature was raised to 60 degrees Celsius for 5 hours. After the reaction, the temperature was lowered to room temperature and quenched with saturated aqueous ammonium chloride solution. The organic phase was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. 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-66-1 (yield 49%).

[0169] Take a 100 ml three-necked round-bottom flask and place a stirring bar and a reflux tube on it. Under nitrogen protection, add the intermediate M-66-1 (1 mmol), 4,4,5,5-tetramethyl-2-(naphtho[2,1-b]benzofuran-2-yl)-1,3,2-dioxaborolane, i.e. C-1 (1.2 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), 1,4-dioxane / water (10 mL / 2 mL) in sequence, heat to 90 degrees Celsius and react for 5 hours. After the reaction is completed, cool to room temperature, filter, rinse the filter cake twice with deionized water and twice with ethanol, and then recrystallize and purify the crude product twice with o-dichlorobenzene to obtain compound M-66 (yield 57%).

[0170] Elemental analysis: C 53 H 33 N3O. Calculated: C, 87.46; H, 4.57; N, 5.77; O, 2.20; Found: C, 87.33; H, 4.79; N, 5.68; HRMS (ESI) m / z [M+H] + : Theoretical value: 727.26; measured value: 728.24.

[0171] The preparation methods of Examples 26-33 are similar to those of Example 22. Specifically, the raw materials used in Examples 26-33 and the products obtained are shown in Table 3 below.

[0172] Table 3

[0173] The characterization data of the products prepared in Examples 26-33 are shown in Table 4:

[0174] Table 4

[0175] Device Examples

[0176] This embodiment provides an organic electroluminescent device, as shown in Figure 1, including an anode 2, a hole injection layer 3, a hole transport layer 4, a light-emitting layer 5, an electron transport layer 6, an electron injection layer 7 and a cathode 8 stacked in sequence on a substrate 1. The device structure is: anode (indium tin oxide (ITO) coated glass substrate) / hole injection layer (HIL) / hole transport layer (HTL) / light-emitting layer (EML) / electron transport layer (ETL) / electron injection layer (EIL) / cathode (Al).

[0177] The materials used to manufacture the organic electroluminescent device are as follows:

[0178] The preparation method of compound B is the same as that of oxazole organic compound N-1 containing benzonaphthofuran, except that By replacing intermediate N1-A, compound B was obtained (yield 64%).

[0179] Elemental analysis: C 35 H 22 N2O2; theoretical value: C, 83.65; H, 4.41; N, 5.57; O, 6.37; found value: C, 83.62; H, 4.41; N, 5.61; HRMS (ESI) m / z [M+H] +: theoretical value: 502.17; found value: 503.32.

[0180] The preparation method of compound C is the same as that of electroluminescent compound N-1, except that Substitute raw material N1-3, Substituting raw material N1-4, compound C was obtained (yield 60%).

[0181] Elemental analysis: C 57 H 35 N3O2; theoretical value: C, 86.23; H, 4.44; N, 5.29; O, 4.03; found value: C, 86.28; H, 4.47; N, 5.21; HRMS (ESI) m / z [M+H] +: theoretical value: 793.27; found value: 794.25.

[0182] The preparation of the organic electroluminescent device comprises the following steps:

[0183] 1) Substrate cleaning:

[0184] A glass substrate coated with transparent ITO was ultrasonically treated in an aqueous detergent (the composition and concentration of the aqueous detergent: ethylene glycol solvent ≤ 10wt%, triethanolamine ≤ 1wt%), then rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone and ethanol (acetone and ethanol volume ratio of 1:1), baked in a clean environment to completely remove moisture, and then cleaned with ultraviolet light and ozone.

[0185] 2) Preparation of organic layer:

[0186] The ITO transparent substrate was transferred to the evaporation equipment and vacuumed to 1×10 -6 to 2×10 -4 Pa, the hole injection layer (HIL) / hole transport layer (HTL) / luminescent layer (EML) / electron transport layer (ETL) / electron injection layer (EIL) / thick cathode (Al) are sequentially deposited on the anode film.

[0187] in:

[0188] The material of the hole injection layer (HIL) is a mixture of NDP-9 and HT, and the specific mass ratio is shown in Table 5;

[0189] The materials of the hole transport layer (HTL) are shown in Table 5;

[0190] The light-emitting layer (EML) was vacuum-deposited by co-evaporation. The materials of the light-emitting layer included a host material and a guest material, wherein the guest material was (piq)2Ir(acac). The specific materials of the host material and the ratio of the host material to the guest material are shown in Table 5.

[0191] The materials of the electron transport layer (ETL) are shown in Table 5;

[0192] The material of the electron injection layer (EIL) is LiQ;

[0193] The cathode is aluminum;

[0194] The materials and thicknesses of some layers of the organic electroluminescent device are shown in Table 5

[0195] Table 5

[0196] The examples in the table represent device examples, and the comparative examples in the table are device comparative examples.

[0197] Test Case

[0198] The organic electroluminescent devices obtained from device examples 1 to 24 and comparative examples 1 to 6 in the device examples were tested.

[0199] Instruments: The device's current, voltage, brightness, luminous spectrum and other characteristics are tested synchronously using a PR 650 spectrum scanning luminance meter and a Keithley K 2400 digital source meter system;

[0200] Test conditions: Photoelectric characteristics test conditions: current density is 10mA / cm2.

[0201] Life test: The current density is 50mA / cm2, and the time (in hours) when the device brightness drops to 95% of the original brightness is recorded. The device performance test results are shown in Table 6:

[0202] Table 6

[0203] The examples in the table represent device examples, and the comparative examples in the table are device comparative examples.

[0204] Obviously, the above embodiments are merely examples for clarity of explanation and are not intended to limit the implementation methods. Those skilled in the art will readily appreciate that other variations or modifications based on the above descriptions are possible. It is not necessary and impossible to enumerate all implementation methods here. Obvious variations or modifications arising therefrom remain within the scope of protection of the present invention.

Claims

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

2. The oxazole-based organic compound containing benzonaphthofuran according to claim 1, characterized in that, Ar is selected from substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C6-C25 arylamino, substituted or unsubstituted C3-C25 heteroarylamino, substituted or unsubstituted C3-C20 heteroaryl; Among them, the substituents in the substituted C6-C25 aryl, substituted C6-C25 arylamino, substituted C3-C25 heteroarylamino, and substituted C3-C20 heteroaryl are each independently selected from deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamino, and C3-C60 heteroarylamino, or a combination of one or at least two of them; Optionally, Ar is selected from substituted or unsubstituted B groups, and the B groups are selected from the following groups: phenyl, naphthyl, biphenyl, phenanthryl, fluoranthenyl, group, terphenyl, triphenylene, phenalenyl, phenylnaphthyl, naphthylphenyl, dimethylfluorenyl, phenylmethylfluorenyl, diphenylfluorenyl, pyridyl, pyridylphenyl, phenylpyridyl, spirobifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirobifluorenyl, dibenzofuranyl, benzonaphthofuranyl, benzonaphthothiophenyl, spiro[fluorene-9,9'-xanthene]yl, phenylmethylfluorenyl, dinaphthofuranyl, dinaphthothiophenyl, dibenzothiophenyl, N,N-diphenylanilino; Among them, the substituents of the substituted B group are selected from deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamino, and C3-C60 heteroarylamino, or a combination of one or at least two of them; 3. The oxazole-based organic compound containing benzonaphthofuran according to claim 1 or 2, characterized in that, Ar is selected from phenyl, naphthyl, biphenyl, fluorenyl, phenanthryl, terphenyl, phenylnaphthyl, naphthylphenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, phenalenyl, dibenzofuranyl, benzonaphthofuranyl, N,N-diphenylanilino.

4. The oxazole-based organic compound containing benzonaphthofuran according to any one of claims 1-3, characterized in that, L is selected from substituted or unsubstituted C6-C15 arylene; among them, the substituents in the substituted C6-C15 arylene are each independently selected from deuterium, halogen, and C1-C62 alkyl, or a combination of one or at least two of them; Optionally, L is selected from phenylene, biphenylene, naphthylene; Optionally, L is selected from phenylene, naphthylene.

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

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

7. A light-emitting host material, characterized in that, It includes the oxazole-based organic compound containing benzonaphthofuran according to any one of claims 1-6.

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

9. The light-emitting host material according to claim 7 or 8, characterized in that, The mass ratio of the first host material to the second host material is 9:1 - 1:9; Optionally, the mass ratio of the first host material to the second host material is 2:8 - 8:2; Optionally, the mass ratio of the first host material to the second host material is 3:7 - 7:3; Further optionally, the mass ratio of the first host material to the second host material is 4:6 - 6:

4.

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

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

12. Application 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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