Organic compound containing dibenzofuranyl and application thereof

Abstract

The invention relates to the technical field of display, in particular to an organic compound containing dibenzofuranyl and application of the organic compound. The organic compound containing the dibenzofuryl group has a structure shown in the specification. The organic electroluminescent device containing the organic compound containing the dibenzofuryl group has relatively low driving voltage, relatively high luminous efficiency and relatively long service life.

Description

Technical Field

[0001] This invention relates to the field of display technology, and more specifically to an organic compound containing a dibenzofuran group and its applications. Background Technology

[0002] Organic light-emitting diodes (OLEDs) are devices that convert electrical energy into light by applying electricity to organic light-emitting materials. They generally have a structure comprising an anode, a cathode, and an organic layer between the anode and cathode. The organic layer of an organic OLED can consist of a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer (containing a host material and dopant materials), an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. The materials used in the organic layer are classified according to their function as hole injection materials, hole transport materials, electron blocking materials, light-emitting materials, electron buffer materials, hole blocking materials, electron transport materials, and electron injection materials. In these organic OLEDs, due to the application of voltage, holes are injected from the anode into the light-emitting layer, and electrons are injected from the cathode into the light-emitting layer. The recombination of holes and electrons forms high-energy excitons. With this energy, the organic light-emitting compound reaches an excited state, and light is emitted by the energy generated when the excited state of the organic light-emitting compound returns to its ground state.

[0003] The most important factor determining the luminescence efficiency of organic EL devices is the luminescent material. The luminescent material must possess high quantum efficiency and high electron and hole mobility, and the resulting luminescent material layer must be uniform and stable. Luminescent materials are classified according to the color of their emission into blue, green, and red luminescent materials, as well as yellow and orange luminescent materials. Furthermore, luminescent materials can also be classified according to their function into host materials and dopant materials.

[0004] However, existing organic electroluminescent materials have low stability and poor matching between HOMO and LUMO energy levels and adjacent energy levels, resulting in an imbalance in carrier mobility. This leads to problems such as high driving voltage, low luminous efficiency, and short lifetime in organic electroluminescent devices containing these materials, which severely limits the application of organic electroluminescent devices. Summary of the Invention

[0005] The purpose of this invention is to overcome the problems of low stability, poor matching degree between HOMO and LUMO energy levels and adjacent energy levels in existing organic electroluminescent materials, which leads to unbalanced carrier mobility and consequently results in high driving voltage, low luminous efficiency and short lifetime of organic electroluminescent devices containing such materials. The invention provides an organic compound containing dibenzofuran group and its application.

[0006] In the definition of substituent terms in this invention:

[0007] As used in this invention, the term "halogen" may include fluorine, chlorine, bromine, or iodine.

[0008] As used in this invention, 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.

[0009] As used in this invention, the term "C3-C30 cycloalkyl" refers to a monocyclic or polycyclic hydrocarbon derived from a main chain of 1 to 30 carbon atoms, including cyclopropyl, cyclobutyl, adamantyl, etc.

[0010] In this invention, aryl and arylene groups include monocyclic, polycyclic, or fused-ring aryl groups, and the rings may be interrupted by short non-aromatic units and may contain spiro structures. Aryl groups include, but are not limited to, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracene, fluorene, and spirodifluorene, etc., and arylene groups include, but are not limited to, phenylene, biphenylene, terphenylene, naphthyl, phenanthryl, anthracene, fluorene, and spirodifluorene, etc.

[0011] In this invention, heteroaryl and hypoaryl groups include monocyclic, polycyclic, or fused-ring heteroaryl groups, wherein the rings can be interrupted by short non-aromatic units, and the heteroatoms include nitrogen, oxygen, and sulfur. Heteroaryl groups include, but are not limited to, furanyl, phenylthio, pyrroloyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetraazinyl, triazolyl, tetraazolyl, furazolidyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophene, isobenzofuranyl, dibenzofuranyl, dibenzothiophene, benzimidazolyl, and benzyl. Benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazoleyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, quinoxalinyl, carbazoleyl, phenoxazinyl, phenthiazinyl, phenanthidyl, benzo[m]dioxacyclopentenyl, dihydroacridyl, and their derivatives; heteroaryl groups include, but are not limited to, furanyl, phenylthio, and pyrroleyl. Imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl Azolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazoleyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinoxolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenthiazinyl, phenanthridineyl, benzom-dioxacyclopentenyl, dihydroacridylyl, and their derivatives, etc.

[0012] As used in this invention, the term "substituted" means that a hydrogen atom in a compound is replaced by another substituent. This 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 can be the same or different.

[0013] As used in this invention, unless otherwise stated, a hydrogen atom includes protium, deuterium, and tritium.

[0014] In this invention, the definition of a group specifies a range of carbon atoms, and the number of carbon atoms is any integer within the defined range, such as C6-C30 aryl. The number of carbon atoms representing an aryl group can be any integer within the range of 6-60, such as 6, 8, 10, 13, 15, 17, 20, 22, 25 or 30.

[0015] In this invention, Indicates a connection key.

[0016] The solution adopted in this invention is as follows:

[0017] This invention provides an organic compound containing a dibenzofuran group, having the structure shown in formula (1):

[0018] General preparation method

[0019] Ar1 is selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;

[0020] Ar2-Ar3 are each independently selected from substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups;

[0021] The substituents in the substituted C6-C30 aryl and substituted C3-C30 heteroaryl groups are each independently selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl.

[0022] It is understandable that for the structure shown in Equation 1 Ar1 can be substituted at any substituted position in ring A or ring B; Ar2 can be substituted at any substituted position in ring E or ring F; ring B is connected to ring C or ring D via a single bond; It can be substituted at any substituted position in ring D and ring E respectively.

[0023] Preferably, Ar1 is selected from hydrogen, deuterium, substituted or unsubstituted C6-C15 aryl groups;

[0024] In this case, each substituent in the substituted C6-C15 aryl group is independently selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl.

[0025] Preferably, Ar1 is selected from hydrogen, deuterium, and phenyl.

[0026] Preferably, Ar2 is selected from substituted or unsubstituted C6-C15 aryl groups;

[0027] In this case, each substituent in the substituted C6-C15 aryl group is independently selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl.

[0028] Preferably, Ar2 is selected from substituted or unsubstituted phenyl groups or substituted or unsubstituted naphthyl groups; wherein the substituents in the substituted phenyl groups or substituted naphthyl groups are selected from deuterium or C1-C6 alkyl groups.

[0029] Preferably, Ar3 is selected from substituted or unsubstituted C6-C20 aryl groups and substituted or unsubstituted C3-C20 heteroaryl groups;

[0030] The substituents in the substituted C6-C20 aryl and substituted C3-C20 heteroaryl are selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl.

[0031] Preferably, Ar3 is selected from substituted or unsubstituted A groups, and the A group is selected from phenyl, naphthyl, biphenyl, terphenyl, dibenzofuranyl, carbazoleyl, and phenylcarbazoleyl.

[0032] Wherein, the substituents in the substituted A group are selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl.

[0033] Preferably, Ar3 is selected from phenyl, naphthyl, biphenyl, terphenyl, dibenzofuranyl, carbazolyl, phenylcarbazolyl, 1-deuterium-substituted phenyl, 1-deuterium-substituted naphthyl, 2-deuterium-substituted phenyl, and 5-deuterium-substituted phenyl.

[0034] Preferably, formula (1) is selected from one of the structures shown in formulas 1-1 to 1-28 below:

[0035]

[0036]

[0037] The definitions of Ar1-Ar3 are the same as above;

[0038] Preferably, the formula (1) is selected from formula 1-1, formula 1-17, and formula 1-19.

[0039] Preferably, the organic compound containing dibenzofuran group is selected from any one of the following M-1 to M-77:

[0040]

[0041]

[0042]

[0043]

[0044]

[0045] The present invention also provides a luminescent host material, comprising a first host material and a second host material, wherein the first host material is an organic compound containing a dibenzofuran group as described above; and the second host material is an organic electroluminescent compound having the structure of the following formula (2):

[0046]

[0047] Where X is selected from O and S;

[0048] L'、L 1’ L 2’ Each is independently selected from the linking bond, substituted or unsubstituted C6-C30 arylene, or substituted or unsubstituted C3-C30 heteroarylene;

[0049] Ar 1’ Ar 2’ Ar is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 aromatic amino, substituted or unsubstituted C3-C60 heteroaryl, or substituted or unsubstituted C3-C60 heteroaryl.

[0050] Preferably, in equation (2), Ar 1’ Ar 2’ Ar is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C6-C15 aryl, substituted or unsubstituted C6-C18 arylamine, substituted or unsubstituted C3-C18 heteroaryl, and substituted or unsubstituted C3-C18 heteroaryl.

[0051] Wherein, the substituents in the substituted C6-C15 aryl, substituted C6-C18 arylamine, substituted C3-C18 heteroaryl, and substituted C3-C18 heteroaryl are each independently selected from one or a combination of at least two of the following: alkyl of C1-C6, cycloalkyl of C3-C12, aryl of C6-C25, heteroaryl of C3-C25, arylamine of C6-C60, and heteroaryl of C3-C60.

[0052] Preferably, the Ar 1’ Ar 2’ Ar and Ar are each independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted E groups, wherein the E groups are selected from the following groups: phenyl, naphthyl, biphenyl, phenanthrene, fluoranyl, ... alkyl, triphenyl, triphenylene, phenylnaphthyl, naphthylphenyl, dimethylfluorenyl, phenylmethylfluorenyl, diphenylfluorenyl, pyridyl, pyridylphenyl, phenylpyridyl, spirodifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirodifluorenyl, dibenzofuranyl, benzonaphthuryl, benzonaphthiophenyl, dibenzothiophenyl, diphenylamino, N,N-diphenylaniline;

[0053] Wherein, each of the substituents in the substituted E group is independently selected from one or a combination of at least two of the following: alkyl (C1-C6), cycloalkyl (C3-C12), aryl (C6-C25), heteroaryl (C3-C25), arylamine (C6-C60), and heteroarylamine (C3-C60).

[0054] Preferred, Ar 1’ -Ar 2’ Each is independently selected from phenyl, naphthyl, biphenyl, yl, triphenyl, phenylnaphthyl, naphthylphenyl, dimethylfluorenyl, diphenylfluorenyl, pyridyl, pyridylphenyl, phenylpyridyl, phenylcarbazolyl, phenylbenzocarbazolyl, phenylphenanthrocarbazolyl, spirodifluorenyl, spiro[fluoren-9,9'-oxanthracene]yl, phenylmethylfluorenyl, dibenzofuranyl, benzonaphthofuryl, diphenylamino, N,N-diphenylaniline;

[0055] Preferably, Ar is selected from phenyl or naphthyl;

[0056] The Ar 1’ Ar 2’ The radicals are independently selected from phenyl, naphthyl, dibenzofuranyl, benzonaphthofuranyl, diphenylamino, and N,N-diphenylaniline.

[0057] Preferably, L', L 1’ L 2’ Each is independently selected from the linking bond, substituted or unsubstituted C6-C12 arylene, or substituted or unsubstituted C3-C12 heteroarylene;

[0058] The substituents of the substituted C6-C12 arylene and the substituted C3-C12 heteroarylene are each independently selected from one or a combination of at least two of the following: alkyl groups of C1-C6, cycloalkyl groups of C3-C12, aryl groups of C6-C25, heteroaryl groups of C3-C25, aryl groups of C6-C60, and heteroaryl groups of C3-C60.

[0059] Preferably, L' is selected from naphthylene;

[0060] Preferred, L 1’ L 2’ Each is independently selected from the linking bond, phenylene, and naphthylene;

[0061] Preferably, X is selected from O.

[0062] Preferably, the organic electroluminescent compound having the structure of formula (2) is selected from one of N-1 to N-654:

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091] Preferably, the mass ratio of the first main material to the second main material is 9:1 to 1:9;

[0092] Preferably, the mass ratio of the first main material to the second main material is 2:8-8:2;

[0093] More preferably, the mass ratio of the first main material to the second main material is 3:7-7:3;

[0094] More preferably, the mass ratio of the first main material to the second main material is 4:6-6:4.

[0095] The present invention also provides an organic electroluminescent material, wherein the organic electroluminescent material comprises any of the above-described organic compounds containing dibenzofuran groups or the above-described light-emitting host materials.

[0096] The present invention also provides an organic electroluminescent device, the organic electroluminescent device comprising a cathode, an anode and an organic layer located between the cathode and the anode, the organic layer comprising the above-described organic compound containing dibenzofuran group or the above-described light-emitting host material or the above-described organic electroluminescent material;

[0097] Preferably, the organic layer comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer, which are stacked sequentially from the anode side to the cathode side.

[0098] The light-emitting layer comprises the organic compound containing dibenzofuran group described above, or the light-emitting host material described above, or the organic electroluminescent material described above.

[0099] The present invention also provides the application of the above-described organic electroluminescent devices in optical fiber equipment, lighting equipment, electrophotographic photosensitive equipment, photoelectric converters, organic solar cells, switching element equipment, organic light-emitting field-effect transistors, image sensors, or dye lasers.

[0100] The beneficial effects of this invention are:

[0101] The organic compound containing dibenzofuran group provided by the present invention is based on the structure of formula (1), and the type of substituent is further limited to improve the structural stability of the compound. Moreover, the HOMO and LUMO energy levels of the organic compound containing dibenzofuran group have a high degree of matching with the adjacent energy levels, so that the carrier mobility of the organic compound containing dibenzofuran group is more balanced. In this way, the organic electroluminescent device containing the organic compound containing dibenzofuran group has a lower driving voltage, higher luminous efficiency and longer lifetime.

[0102] Furthermore, the light-emitting host material provided by the present invention includes a first host material and a second host material, wherein the first host material is an organic compound containing a dibenzofuran group having the structure shown in formula (1); the second host material is a compound having the structure shown in formula (2). The two compounds complement each other to facilitate the matching of HOMO and LUMO energy levels with adjacent energy levels, so that the organic material composition obtains higher stability and a more balanced carrier mobility, thereby enabling the organic electroluminescent device containing the material to have a better lifetime, while also having a lower driving voltage and higher efficiency. Attached Figure Description

[0103] To more clearly illustrate the specific embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the specific embodiments or the prior art will be briefly introduced below. Obviously, the drawings described below are some embodiments of the present invention. For those skilled in the art, other drawings can be obtained from these drawings without creative effort.

[0104] Figure 1 This is a structural diagram of the organic electroluminescent device in the device embodiment of the present invention;

[0105] 1-Substrate; 2-Anode; 3-Hole injection layer; 4-Hole transport layer; 5-Light emission layer; 6-Electron transport layer; 7-Electron injection layer; 8-Cathode. Detailed Implementation

[0106] The following embodiments are provided to better understand the present invention and are not limited to the preferred embodiments described. They do not constitute a limitation on the content and scope of protection of the present invention. Any product that is the same as or similar to the present invention, derived by any person under the guidance of the present invention or by combining the features of the present invention with other prior art, falls within the protection scope of the present invention.

[0107] For experiments not specifically described in the examples, the procedures or conditions should be followed according to the conventional experimental procedures described in the literature in this field. Reagents or instruments whose manufacturers are not specified are all commercially available conventional reagent products.

[0108] The term "organic electroluminescent material" in this disclosure refers to a material that can be used in an organic electroluminescent device and may contain at least one compound. If desired, the organic electroluminescent material may be contained in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole assist material, a light-emitting assist material, an electron blocking material, a light-emitting 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.

[0109] The term "multiple organic electroluminescent materials" in this disclosure refers to one or more organic electroluminescent materials comprising a combination of at least two compounds, said materials being contained in any layer constituting an organic electroluminescent device. It can mean both materials contained before (e.g., before vapor deposition) and materials contained after (e.g., after vapor deposition) the organic electroluminescent device. For example, multiple organic electroluminescent materials can be a combination of at least two compounds, said materials being contained in at least one of: a hole injection layer, a hole transport layer, a hole assist layer, a light-emitting assist layer, an electron blocking layer, a light-emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. The at least two compounds can be contained in the same layer or different layers, and can be mixed-evaporated or co-evaporated, or can be evaporated individually.

[0110] In this invention, organic compounds containing dibenzofuran groups having the structure of formula (1) are prepared via the following synthetic route:

[0111]

[0112] Preparation of the required intermediate in organic compounds containing dibenzofuran groups having the structure of formula (1):

[0113] Synthesis of intermediate SubM30-A

[0114]

[0115] After purging the three-necked reaction flask with nitrogen, equipped with a mechanical stirrer, a cryostat, and a constant-pressure dropping funnel, SubM30-Aa (10 mmol) and 100 ml of tetrahydrofuran were added sequentially. Stirring was started, and the temperature was lowered to -70 to -80 °C. Then, n-butyllithium (12 mmol) was added dropwise while maintaining the system temperature during the addition. After the addition was complete, the temperature was maintained for 1 hour. D2O (20 mmol) was slowly added, and the temperature was naturally raised to 25 to 30 °C. 100 ml of water and 100 ml of toluene were added, and the mixture was stirred and separated. The aqueous phase was extracted once with 100 ml of toluene, separated, and the organic phases were combined. 7 g of anhydrous sodium sulfate was added to the organic phase, and the mixture was stirred and dried. The organic phase was filtered and concentrated (-0.08 to 0.09 MPa, 55 to 60 °C) until no liquid flowed out to obtain compound SubM30-A-1, with a yield of 76%.

[0116] After purging the three-necked reaction flask with nitrogen, equipped with a mechanical stirrer, thermometer, and condenser, intermediate SubM30-A-1 (10 mmol), starting material pinacol diboronate (12 mmol), 100 ml of 1,4-dioxane, potassium acetate (20 mmol), and Pd2(dba)3 (0.05 mmol) were added sequentially. The mixture was heated to 100 °C and reacted for 3 h. The temperature was lowered to 25–30 °C, and 100 ml of water and 100 ml of toluene were added. The mixture was stirred and separated. The aqueous phase was extracted once with 100 ml of toluene, separated, and the organic phases were combined. 7 g of anhydrous sodium sulfate was added to the organic phase, and the mixture was stirred and dried. The organic phase was filtered and concentrated (-0.08–0.09 MPa, 55–60 °C) until no liquid flowed out. 50 ml of a mixed solvent of dichloromethane and petroleum ether was added with stirring, and the mixture was cooled to 0–5 °C and filtered to obtain compound SubM30-A in 62% yield.

[0117] Synthesis of intermediate SubM31-A

[0118]

[0119] The preparation method of SubM31-A is the same as that of SubM30-A, except that SubM31-Aa is used instead of SubM30-Aa to obtain SubM31-A with a yield of 75%.

[0120] Synthesis of intermediate SubM32-A

[0121]

[0122] The preparation method of SubM32-A is the same as that of SubM30-A, except that SubM32-Aa is used instead of SubM30-Aa to obtain SubM32-A with a yield of 60%.

[0123] Synthesis of intermediate SubM33-A

[0124]

[0125] The preparation method of SubM33-A is the same as that of SubM30-A, except that SubM33-Aa is used instead of SubM30-Aa to obtain SubM33-A with a yield of 72%.

[0126] Synthesis of intermediate SubM33-B

[0127]

[0128] The preparation method of SubM34-B is the same as that of SubM30-A, except that SubM33-Ba is used instead of SubM30-Aa to obtain SubM33-B with a yield of 63%.

[0129] Synthesis of intermediate SubM33-C

[0130]

[0131] After purging the three-necked reaction flask with nitrogen, which is equipped with a mechanical stirrer, thermometer, and condenser, the following ingredients were added in sequence: SubM33-Ca (10 mmol), intermediate SubM33-B (10 mmol), potassium carbonate (20 mmol), Pd(PPh3)4 (0.05 mmol), 100 mL of 1,4-dioxane, and 30 mL of water. The stirring was started and the mixture was heated to 70–75 °C for 3 h. Cool to 25–30°C, add 100 mL of water and 100 mL of dichloromethane, stir and separate. Extract the aqueous phase once with 100 mL of dichloromethane, separate, combine the organic phases, add 7 g of anhydrous sodium sulfate to the organic phase, stir and dry, filter, concentrate the organic phase (-0.08–0.09 MPa, 55–60°C) until no liquid flows out, stir and add 20 mL of petroleum ether, cool to 0–5°C, filter to obtain crude product, recrystallize the crude product from toluene to obtain intermediate SubM33-C-1, yield 72%.

[0132] After purging the three-necked reaction flask with nitrogen, equipped with a mechanical stirrer, thermometer, and condenser, intermediate SubM33-C-1 (10 mmol), starting material pinacol diboronate (12 mmol), 100 mL of 1,4-dioxane, potassium acetate (20 mmol), and Pd2(dba)3 (0.05 mmol) were added sequentially. The mixture was heated to 100 °C and reacted for 3 h. The temperature was lowered to 25–30 °C, and 100 mL of water and 100 mL of toluene were added. The mixture was stirred and separated. The aqueous phase was extracted once with 100 mL of toluene, separated, and the organic phases were combined. 7 g of anhydrous sodium sulfate was added to the organic phase, and the mixture was stirred and dried. The organic phase was filtered and concentrated (-0.08–0.09 MPa, 55–60 °C) until no liquid flowed out. 50 mL of a mixed solvent of dichloromethane and petroleum ether was added with stirring, and the mixture was cooled to 0–5 °C and filtered to obtain intermediate SubM33-C in 70% yield.

[0133] Preparation of the intermediate required for organic electroluminescent compounds having the structure of formula (2):

[0134] Synthesis of intermediate N1-A

[0135]

[0136] After purging the three-necked reaction flask with nitrogen, which was equipped with a mechanical stirrer, thermometer, and condenser, intermediates N1-Aa (10 mmol), N1-Ab (10 mmol), 100 mL toluene, 20 mL ethanol, 20 mL water, potassium carbonate (20 mmol), and Pd(PPh3)4 (0.05 mmol) were added sequentially. The mixture was heated to 70–80 °C and reacted for 3 h. The temperature was then lowered to 25–30 °C, and 100 mL of water and 100 mL of toluene were added. The mixture was stirred and separated. The aqueous phase was extracted once with 100 mL of toluene, and the liquid phases were separated and combined. 7 g of anhydrous sodium sulfate was added to the organic phase, and the mixture was stirred and dried. The organic phase was filtered and concentrated (-0.08–0.09 MPa, 55–60 °C) until no liquid flowed out. 50 mL of a mixed solvent of dichloromethane and petroleum ether was added with stirring, and the mixture was cooled to 0–5 °C and filtered to obtain compound N1-A in 67% yield.

[0137] Elemental analysis: C 23 H 14 Theoretical values ​​of ClNO: C, 77.64; H, 3.97; Cl, ​​9.96; N, 3.94; O, 4.50; Measured values: C, 77.59; H, 3.98; Cl, ​​9.95; N, 3.98;

[0138] HRMS(ESI)m / z[M+H] + Theoretical value: 355.08; Measured value: 356.32.

[0139] The preparation steps of intermediates N2-A to N12-A are the same as those for N1-A, except that N1-Aa is replaced with brominated and chlorinated starting materials with different substitution sites than N1-Aa, and N1-Ab is replaced with borate ester starting materials with different substitution sites than N1-Ab:

[0140]

[0141]

[0142] Synthetic route of intermediate N13-A

[0143]

[0144] After purging the three-necked reaction flask with nitrogen, equipped with a mechanical stirrer, thermometer, and condenser, intermediates N13-Aa (10 mmol), N13-Ab (10 mmol), 100 mL toluene, 20 mL ethanol, 20 mL water, potassium carbonate (20 mmol), and Pd(PPh3)4 (0.05 mmol) were added sequentially. The mixture was heated to 70 °C and reacted for 3 h. The temperature was lowered to 25–30 °C, and 100 mL of water and 100 mL of toluene were slowly added with stirring and separation. The aqueous phase was extracted once with 100 mL of toluene, separated, and the organic phases were combined. The organic phase was washed several times with water until neutral, and then 7 g of anhydrous sodium sulfate was added with stirring and dried. The mixture was filtered, and the organic phase was concentrated (-0.08–0.09 MPa, 55–60 °C) until no liquid flowed out. 50 mL of a mixed solvent of dichloromethane and petroleum ether was added with stirring, and the mixture was cooled to 0–5 °C and filtered to obtain compound N13-A in 72% yield.

[0145] Elemental analysis: C 27 H 16 Theoretical values ​​of ClNO: C, 79.90; H, 3.97; Cl, ​​8.73; N, 3.45; O, 3.94; Measured values: C, 79.90; H, 3.97; Cl, ​​8.73; N, 3.45; O, 3.94;

[0146] HRMS(ESI)m / z[M+H] + Theoretical value: 405.09; Measured value: 406.12.

[0147] Example 1

[0148] This embodiment provides an organic electroluminescent compound N-1 in the luminescent host material. The synthesis of organic electroluminescent compound N-1 specifically includes the following steps:

[0149]

[0150] After purging the three-necked reaction flask with nitrogen, which is equipped with a mechanical stirrer, thermometer, and condenser, intermediate N1-B (10 mmol), intermediate N1-A (10 mmol), and 100 mL of toluene were added sequentially. The mixture was heated under reflux to remove water for 0.5 h, cooled to 70–80 °C, and sodium tert-butoxide (15 mmol), Pd2(dba)3 (0.05 mmol), and s-phos (0.1 mmol) were slowly added. After the system stabilized, the mixture was heated to 100–110 °C and reacted for 3 h. Cool to 25–30°C, add 100 mL of water and 100 mL of toluene, stir and separate the liquid. Extract the aqueous phase once with 100 mL of toluene, separate the liquid and combine the organic phases. Add 7 g of anhydrous sodium sulfate to the organic phase, stir and dry, filter, concentrate the organic phase (-0.08–0.09 MPa, 55–60°C) until no liquid flows out, stir and add 20 mL of petroleum ether, cool to 0–5°C, filter, and obtain the organic electroluminescent compound N-1, with a yield of 68%.

[0151] Elemental analysis: C 41 H 28 Theoretical N₂O values: C, 87.21; H, 5.00; N, 4.96; O, 2.83; Measured values: C, 87.15; H, 5.01; N, 4.99; HRMS(ESI) m / z [M+H] + Theoretical value: 564.22; Measured value: 565.31.

[0152] Example 2

[0153] This embodiment provides an organic electroluminescent compound N-5 as the luminescent host material. The synthesis of organic electroluminescent compound N-5 specifically includes the following steps:

[0154]

[0155] After purging the three-necked reaction flask with a mechanical stirrer, thermometer, and condenser with nitrogen, intermediate N6-B (10 mmol), intermediate N1-A (10 mmol), and 100 mL of toluene were added sequentially. The mixture was heated under reflux to remove water for 0.5 h, cooled to 70–80 °C, and sodium tert-butoxide (15 mmol), Pd2(dba)3 (0.05 mmol), and s-phos (0.1 mmol) were slowly added. After the system stabilized, the mixture was heated to 100–110 °C and reacted for 3 h. Cool to 25–30°C, add 100 mL of water and 100 mL of toluene, stir and separate the liquid. Extract the aqueous phase once with 100 mL of toluene, separate the liquid and combine the organic phases. Add 7 g of anhydrous sodium sulfate to the organic phase, stir and dry, filter, concentrate the organic phase (-0.08–0.09 MPa, 55–60°C) until no liquid flows out, stir and add 20 mL of petroleum ether, cool to 0–5°C, filter, and obtain the organic electroluminescent compound N-5, with a yield of 66%.

[0156] Elemental analysis: C 41 H 26 Theoretical N2O2 values: C, 85.10; H, 4.53; N, 4.84; O, 5.53; Measured values: C, 85.10; H, 4.53; N, 4.84; O, 5.53;

[0157] HRMS(ESI)m / z[M+H] + Theoretical value: 578.20; Measured value: 579.25.

[0158] Example 3

[0159] This embodiment provides an organic electroluminescent compound N-16 in the luminescent host material. The synthesis of organic electroluminescent compound N-16 specifically includes the following steps:

[0160]

[0161] After purging the three-necked reaction flask with a mechanical stirrer, thermometer, and condenser with nitrogen, intermediate N16-B (10 mmol), intermediate N16-A (10 mmol), and 100 mL of toluene were added sequentially. The mixture was heated under reflux to remove water for 0.5 h, cooled to 70–80 °C, and sodium tert-butoxide (15 mmol), Pd2(dba)3 (0.05 mmol), and s-phos (0.1 mmol) were slowly added. After the system stabilized, the mixture was heated to 100–110 °C and reacted for 3 h. Cool to 25–30°C, add 100 mL of water and 100 mL of toluene, stir and separate the liquid. Extract the aqueous phase once with 100 mL of toluene, separate the liquid and combine the organic phases. Add 7 g of anhydrous sodium sulfate to the organic phase, stir and dry, filter, concentrate the organic phase (-0.08–0.09 MPa, 55–60°C) until no liquid flows out, stir and add 20 mL of petroleum ether, cool to 0–5°C, filter, and obtain the organic electroluminescent compound N-16, with a yield of 61%.

[0162] Elemental analysis: C 51 H 32 Theoretical N₂O₂ values: C, 85.97; H, 4.49; N, 4.46; O, 5.09; Measured values: C, 85.94; H, 4.50; N, 4.48; HRMS(ESI) m / z [M+H] + Theoretical value: 628.22; Measured value: 629.25.

[0163] Example 4

[0164] This embodiment provides an organic electroluminescent compound N-18 as the host material for light emission. The synthesis of organic electroluminescent compound N-18 specifically includes the following steps:

[0165]

[0166] After purging the three-necked reaction flask with a mechanical stirrer, thermometer, and condenser with nitrogen, intermediate N18-B (10 mmol), intermediate N1-A (10 mmol), and 100 mL of toluene were added sequentially. The mixture was heated under reflux to remove water for 0.5 h, cooled to 70–80 °C, and sodium tert-butoxide (15 mmol), Pd2(dba)3 (0.05 mmol), and s-phos (0.1 mmol) were slowly added. After the system stabilized, the mixture was heated to 100–110 °C and reacted for 3 h. Cool to 25–30°C, add 100 mL of water and 100 mL of toluene, stir and separate the liquid. Extract the aqueous phase once with 100 mL of toluene, separate the liquid and combine the organic phases. Add 7 g of anhydrous sodium sulfate to the organic phase, stir and dry, filter, concentrate the organic phase (-0.08–0.09 MPa, 55–60°C) until no liquid flows out, stir and add 20 mL of petroleum ether, cool to 0–5°C, filter, and obtain the organic electroluminescent compound N-18, with a yield of 61%.

[0167] Elemental analysis: C 53 H 37 Theoretical N3O values: C, 86.98; H, 5.10; N, 5.74; O, 2.19; Measured values: C, 87.00; H, 5.11; N, 5.70; HRMS(ESI) m / z [M+H] + Theoretical value: 731.29; Measured value: 732.15.

[0168] Example 5

[0169] This embodiment provides an organic electroluminescent compound N-45 in the luminescent host material. The synthesis of organic electroluminescent compound N-45 specifically includes the following steps:

[0170]

[0171] After purging the three-necked reaction flask with a mechanical stirrer, thermometer, and condenser with nitrogen, intermediate N45-B (10 mmol), intermediate N1-A (10 mmol), and 100 mL of toluene were added sequentially. The mixture was heated under reflux to remove water for 0.5 h, cooled to 70–80 °C, and sodium tert-butoxide (15 mmol), Pd2(dba)3 (0.05 mmol), and s-phos (0.1 mmol) were slowly added. After the system stabilized, the mixture was heated to 100–110 °C and reacted for 3 h. Cool to 25–30°C, add 100 mL of water and 100 mL of toluene, stir and separate the liquid. Extract the aqueous phase once with 100 mL of toluene, separate the liquid and combine the organic phases. Add 7 g of anhydrous sodium sulfate to the organic phase, stir and dry, filter, concentrate the organic phase (-0.08–0.09 MPa, 55–60°C) until no liquid flows out, stir and add 20 mL of petroleum ether, cool to 0–5°C, filter, and obtain the organic electroluminescent compound N-45, with a yield of 65%.

[0172] Elemental analysis: C 49 H 32 Theoretical N2O values: C, 88.53; H, 4.85; N, 4.21; O, 2.41; Measured values: C, 88.49; H, 4.86; N, 4.24; HRMS(ESI) m / z [M+H] + Theoretical value: 664.25; Measured value: 665.19.

[0173] Example 6

[0174] This embodiment provides an organic electroluminescent compound N-130 in the luminescent host material. The synthesis of organic electroluminescent compound N-130 specifically includes the following steps:

[0175]

[0176] After purging the three-necked reaction flask with nitrogen, which is equipped with a mechanical stirrer, thermometer, and condenser, intermediate N130-B (10 mmol), intermediate N4-A (10 mmol), and 100 mL of toluene were added sequentially. The mixture was heated under reflux to remove water for 0.5 h, cooled to 70–80 °C, and sodium tert-butoxide (15 mmol), Pd2(dba)3 (0.05 mmol), and s-phos (0.1 mmol) were slowly added. After the system stabilized, the mixture was heated to 100–110 °C and reacted for 3 h. Cool to 25–30°C, add 100 mL of water and 100 mL of toluene, stir and separate the liquid. Extract the aqueous phase once with 100 mL of toluene, separate the liquid and combine the organic phases. Add 7 g of anhydrous sodium sulfate to the organic phase, stir and dry, filter, concentrate the organic phase (-0.08–0.09 MPa, 55–60°C) until no liquid flows out, stir and add 20 mL of petroleum ether, cool to 0–5°C, filter, and obtain the organic electroluminescent compound N-130, with a yield of 65%.

[0177] Elemental analysis: C 47 H 30 Theoretical N₂O₂ values: C, 86.22; H, 4.62; N, 4.28; O, 4.89; Measured values: C, 86.20; H, 4.61; N, 4.31; HRMS(ESI) m / z [M+H] + Theoretical value: 654.23; Measured value: 655.28.

[0178] Example 7

[0179] This embodiment provides an organic compound M-1 containing a dibenzofuran group. The synthesis of the organic compound M-1 containing a dibenzofuran group specifically includes the following steps:

[0180]

[0181] After purging the three-necked reaction flask with nitrogen, equipped with a mechanical stirrer, thermometer, and condenser, Sub-1-a (10 mmol), intermediate M1-A (10 mmol), 100 mL tetrahydrofuran, 20 mL water, potassium carbonate (20 mmol), and Pd(PPh3)4 (0.05 mmol) were added sequentially. The mixture was heated to 70–80 °C and reacted for 3 h. The temperature was then lowered to 25–30 °C, and 100 mL of water and 100 mL of toluene were added. The mixture was stirred and separated. The aqueous phase was extracted once with 100 mL of toluene, and the liquid phases were separated and combined. 7 g of anhydrous sodium sulfate was added to the organic phase, and the mixture was stirred and dried. The organic phase was filtered and concentrated (-0.08–0.09 MPa, 55–60 °C) until no liquid flowed out. 50 mL of a mixed solvent of dichloromethane and petroleum ether was added with stirring, and the mixture was cooled to 0–5 °C and filtered to obtain compound M1-B in 65% yield.

[0182] After purging the three-necked reaction flask with nitrogen, which is equipped with a mechanical stirrer, thermometer, and condenser, intermediate M1-B (10 mmol), intermediate Sub-1-b (10 mmol), potassium carbonate (20 mmol), Pd(PPh3)4 (0.05 mmol), 100 mL of 1,4-dioxane, and 30 mL of water were added in sequence. The stirring was turned on and the mixture was heated to 70-75 °C for 3 h. Cool to 25–30°C, add 100 mL of water and 100 mL of dichloromethane, stir and separate. Extract the aqueous phase once with 100 mL of dichloromethane, separate, combine the organic phases, add 7 g of anhydrous sodium sulfate to the organic phase, stir and dry, filter, concentrate the organic phase (-0.08–0.09 MPa, 55–60°C) until no liquid flows out, stir and add 20 mL of petroleum ether, cool to 0–5°C, filter to obtain crude product, recrystallize the crude product from toluene to obtain organic compound M-1 containing dibenzofuran group, yield 72%.

[0183] Elemental analysis: C47H29N3O Theoretical values: C, 86.61; H, 4.49; N, 6.45; O, 2.45; Measured values: C, 86.65; H, 4.7; N, 6.44; HRMS(ESI) m / z [M+H]+: Theoretical value: 651.23; Measured value: 652.23.

[0184] Example 8

[0185] This embodiment provides an organic compound M-4 containing a dibenzofuran group. The synthesis of the organic compound M-4 containing a dibenzofuran group specifically includes the following steps:

[0186]

[0187] After purging the three-necked reaction flask with nitrogen, equipped with a mechanical stirrer, thermometer, and condenser, the following ingredients were added sequentially: Sub-4-a (10 mmol), intermediate M4-A (10 mmol), potassium carbonate (20 mmol), Pd(PPh3)4 (0.05 mmol), 100 mL of 1,4-dioxane, and 30 mL of water. Stirring was started, and the mixture was heated to 70–75 °C for 3 h. The temperature was then lowered to 25–30 °C, and 100 mL of water and 100 mL of dichloromethane were added. The mixture was stirred and separated. The aqueous phase was extracted once with 100 mL of dichloromethane, separated, and the organic phases were combined. 7 g of anhydrous sodium sulfate was added to the organic phase, and the mixture was dried by stirring. The organic phase was filtered and concentrated (-0.08–0.09 MPa, 55–60 °C) until no liquid flowed out. 20 mL of petroleum ether was added with stirring, and the temperature was lowered to 0–5 °C. The mixture was filtered to obtain the crude product. The crude product was recrystallized from toluene to obtain product M4-B, with a yield of 66%.

[0188] After purging the three-necked reaction flask with nitrogen, which is equipped with a mechanical stirrer, thermometer, and condenser, intermediate M4-B (10 mmol), intermediate Sub-4-b (10 mmol), potassium carbonate (20 mmol), Pd(PPh3)4 (0.05 mmol), 100 mL of 1,4-dioxane, and 30 mL of water were added in sequence. The stirring was turned on and the mixture was heated to 70-75 °C for 3 h. Cool to 25–30°C, add 100 mL of water and 100 mL of dichloromethane, stir and separate. Extract the aqueous phase once with 100 mL of dichloromethane, separate, combine the organic phases, add 7 g of anhydrous sodium sulfate to the organic phase, stir and dry, filter, concentrate the organic phase (-0.08–0.09 MPa, 55–60°C) until no liquid flows out, stir and add 20 mL of petroleum ether, cool to 0–5°C, filter to obtain crude product, recrystallize the crude product from toluene to obtain organic compound M-4 containing dibenzofuran group, yield 72%.

[0189] Elemental analysis: C 53 H 42Theoretical N4O values: C, 85.92; H, 4.35; N, 7.56; O, 2.16; Measured values: C, 85.95; H, 4.33; N, 7.54; HRMS(ESI) m / z [M+H]+: Theoretical value: 740.26; Measured value: 740.36.

[0190] Example 9

[0191] This embodiment provides an organic compound M-6 containing a dibenzofuran group. The synthesis of the organic compound M-6 containing a dibenzofuran group specifically includes the following steps:

[0192]

[0193] Preparation of intermediate M6-B: The preparation method is the same as that of M4-B, except that Sub-6-a is used instead of Sub-4-a and M6-A is used instead of M4-A to obtain intermediate M6-B with a yield of 75%.

[0194] Preparation of organic compound M-6 containing dibenzofuran group: The preparation method is the same as that of M-4, except that intermediate M6-B is replaced by M4-B and Sub-1-b is replaced by Sub-4-b, to obtain organic compound M-6 containing dibenzofuran group, with a yield of 68%.

[0195] Elemental analysis: C47H24D5N3O Theoretical values: C, 85.95; H, 5.22; N, 6.40; O, 2.44; Measured values: C, 85.93; H, 5.20; N, 6.42; HRMS(ESI) m / z [M+H]+: Theoretical value: 656.26; Measured value: 657.26.

[0196] Example 10

[0197] This embodiment provides an organic compound M-13 containing a dibenzofuran group. The synthesis of the organic compound M-13 containing a dibenzofuran group specifically includes the following steps:

[0198]

[0199] Preparation of intermediate M13-B: The preparation method is the same as that of M1-B, except that M13-A is used instead of M1-A to obtain intermediate M13-B with a yield of 70%.

[0200] Preparation of organic compound M-13 containing dibenzofuran group: The preparation method is the same as that of M-1, except that intermediate M13-B is used instead of M1-B and Sub-13-b is used instead of Sub-1-b, to obtain organic compound M-13 containing dibenzofuran group, with a yield of 72%.

[0201] Elemental analysis: C47H29N3O Theoretical values: C, 86.61; H, 4.49; N, 6.45; O, 2.45; Measured values: C, 86.64; H, 4.48; N, 6.42; HRMS(ESI) m / z [M+H]+: Theoretical value: 651.23; Measured value: 652.31.

[0202] Example 11

[0203] This embodiment provides an organic compound M-19 containing a dibenzofuran group. The synthesis of the organic compound M-19 containing a dibenzofuran group specifically includes the following steps:

[0204]

[0205] After purging the three-necked reaction flask with nitrogen, equipped with a mechanical stirrer, thermometer, and condenser, Sub-1-a (10 mmol), intermediate M19-A (10 mmol), 100 mL tetrahydrofuran, 20 mL water, potassium carbonate (20 mmol), and Pd(PPh3)4 (0.05 mmol) were added sequentially. The mixture was heated to 70–80 °C and reacted for 3 h. The temperature was then lowered to 25–30 °C, and 100 mL of water and 100 mL of toluene were added. The mixture was stirred and separated. The aqueous phase was extracted once with 100 mL of toluene, and the two phases were separated. The combined organic phases were added, and 7 g of anhydrous sodium sulfate was added and stirred until dry. The mixture was filtered, and the organic phase was concentrated (-0.08–0.09 MPa, 55–60 °C) until no liquid flowed out. A mixed solvent of dichloromethane and petroleum ether was added with stirring, and the mixture was cooled to 0–5 °C and filtered to obtain intermediate M19-B in 65% yield.

[0206] After purging the three-necked reaction flask with nitrogen, which is equipped with a mechanical stirrer, thermometer, and condenser, intermediate M19-B (10 mmol), raw material Sub-1-b (10 mmol), potassium carbonate (20 mmol), Pd(PPh3)4 (0.05 mmol), 100 mL of 1,4-dioxane, and 30 mL of water were added in sequence. The stirring was turned on and the mixture was heated to 70-75 °C for 3 h. Cool to 25–30°C, add 100 mL of water and 100 mL of dichloromethane, stir and separate. Extract the aqueous phase once with 100 mL of dichloromethane, separate, combine the organic phases, add 7 g of anhydrous sodium sulfate to the organic phase, stir and dry, filter, concentrate the organic phase (-0.08–0.09 MPa, 55–60°C) until no liquid flows out, stir and add 20 mL of petroleum ether, cool to 0–5°C, filter to obtain crude product, recrystallize the crude product from toluene to obtain organic compound M-19 containing dibenzofuran group, yield 72%.

[0207] Elemental analysis: C47H29N3O Theoretical values: C, 86.61; H, 4.49; N, 6.45; O, 2.45; Measured values: C, 86.63; H, 4.48; N, 6.46; HRMS(ESI) m / z [M+H]+: Theoretical value: 651.23; Measured value: 652.21.

[0208] Example 12

[0209] This embodiment provides an organic compound M-29 containing a dibenzofuran group. The synthesis of the organic compound M-29 containing a dibenzofuran group specifically includes the following steps:

[0210]

[0211] After purging the three-necked reaction flask with nitrogen, equipped with a mechanical stirrer, thermometer, and condenser, Sub-1-a (10 mmol), intermediate M29-A (10 mmol), 100 mL tetrahydrofuran, 20 mL water, potassium carbonate (20 mmol), and Pd(PPh3)4 (0.05 mmol) were added sequentially. The mixture was heated to 70–80 °C and reacted for 3 h. The temperature was then lowered to 25–30 °C, and 100 mL of water and 100 mL of toluene were added. The mixture was stirred and separated. The aqueous phase was extracted once with 100 mL of toluene, and the liquid phases were separated and combined. 7 g of anhydrous sodium sulfate was added to the organic phase, and the mixture was stirred and dried. The organic phase was filtered and concentrated (-0.08–0.09 MPa, 55–60 °C) until no liquid flowed out. 50 mL of a mixed solvent of dichloromethane and petroleum ether was added with stirring, and the mixture was cooled to 0–5 °C and filtered to obtain compound M29-B in 64% yield.

[0212] After purging the three-necked reaction flask with nitrogen, which is equipped with a mechanical stirrer, thermometer, and condenser, intermediate M29-B (10 mmol), intermediate Sub-22-b (10 mmol), potassium carbonate (20 mmol), Pd(PPh3)4 (0.05 mmol), 100 mL of 1,4-dioxane, and 30 mL of water were added in sequence. The stirring was turned on and the mixture was heated to 70-75 °C for 3 h. Cool to 25–30°C, add 100 mL of water and 100 mL of dichloromethane, stir and separate. Extract the aqueous phase once with 100 mL of dichloromethane, separate, combine the organic phases, add 7 g of anhydrous sodium sulfate to the organic phase, stir and dry, filter, concentrate the organic phase (-0.08–0.09 MPa, 55–60°C) until no liquid flows out, stir and add 20 mL of petroleum ether, cool to 0–5°C, filter to obtain crude product, recrystallize the crude product from toluene to obtain organic compound M-29 containing dibenzofuran group, yield 66%. H, 4.49; N, 6.45; O, 2.45; Measured value: C, 86.63; H, 4.48; N, 6.44; HRMS(ESI) m / z [M+H]+: Theoretical value: 651.23; Measured value: 652.22.

[0213] Example 13

[0214] This embodiment provides an organic compound M-30 containing a dibenzofuran group. The synthesis of the organic compound M-30 containing a dibenzofuran group specifically includes the following steps:

[0215]

[0216] Preparation of intermediate Sub-30-a: After purging the three-necked reaction flask with mechanical stirrer, thermometer and condenser with nitrogen, add cyanuric chloride (10 mmol), SubM30-A (1.05 mmol), i.e. 4-D-phenylboronic acid ester, sodium carbonate (20 mmol), Pd(PPh3)2Cl2 (0.05 mmol) and tetrahydrofuran 100 mL in sequence, heat to 40-50℃ and react for 10 h. After the reaction was complete, 100 mL of water and 100 mL of dichloromethane were added, stirred, and separated. The aqueous phase was extracted once with 100 mL of dichloromethane, separated, and the organic phases were combined. 10 g of anhydrous sodium sulfate was added to the organic phase, stirred, dried, filtered, and the organic phase was concentrated (-0.08 to 0.09 MPa, 55 to 60 °C) until no liquid flowed out. 50 mL of a mixed solvent of dichloromethane and petroleum ether was added, stirred, cooled to 0 to 5 °C, and filtered to obtain intermediate Sub-30-A, with a yield of 51%.

[0217] Preparation of intermediate M30-B: The preparation method is the same as that of M4-B, except that Sub-30-a is used instead of Sub-4-a and M30-A is used instead of M4-A to obtain intermediate M30-B with a yield of 46%.

[0218] Preparation of organic compound M-30 containing dibenzofuran group: The preparation method is the same as that of M-4, except that intermediate M30-B is used instead of M4-B, and Sub-30-b is used instead of Sub-4-b, to obtain organic compound M-30 containing dibenzofuran group, with a yield of 58%.

[0219] Elemental analysis: C47H28DN3O Theoretical values: C, 86.48; H, 4.63; N, 6.44; O, 2.45; Measured values: C, 86.47; H, 4.61; N, 6.46; HRMS(ESI) m / z [M+H]+: Theoretical value: 652.24; Measured value: 653.23.

[0220] Example 14

[0221] This embodiment provides an organic compound M-31 containing a dibenzofuran group. The synthesis of the organic compound M-31 containing a dibenzofuran group specifically includes the following steps:

[0222]

[0223] Preparation of intermediate Sub-31-a: The preparation method is the same as that of Sub-30-a, except that Sub31-A is used instead of Sub30-A to obtain intermediate Sub-31-a with a yield of 56%.

[0224] Preparation of intermediate M31-B: The preparation method is the same as that of M4-B, except that Sub-31-a is replaced by Sub-4-a and M30-A is replaced by M4-A to obtain intermediate M31-B with a yield of 55%.

[0225] Preparation of organic compound M-31 containing dibenzofuran group: The preparation method is the same as that of M-4, except that intermediate M31-B is replaced by M4-B and Sub-31-b is replaced by Sub-4-b, to obtain organic compound M-31 containing dibenzofuran group, with a yield of 53%.

[0226] Elemental analysis: C47H27D2N3O Theoretical values: C, 86.35; H, 4.78; N, 6.43; O, 2.45; Measured values: C, 86.34; H, 4.77; N, 6.44; HRMS(ESI) m / z [M+H]+: Theoretical value: 653.24; Measured value: 654.25.

[0227] Example 15

[0228] This embodiment provides an organic compound M-32 containing a dibenzofuran group. The synthesis of the organic compound M-32 containing a dibenzofuran group specifically includes the following steps:

[0229]

[0230] Preparation of intermediate Sub-32-a: The preparation method is the same as that of Sub-30-a, except that Sub32-A is used instead of Sub30-A to obtain intermediate Sub-32-a with a yield of 66%.

[0231] Preparation of intermediate M32-B: The preparation method is the same as that of M4-B, except that Sub-32-a is used instead of Sub-4-a and M30-A is used instead of M4-A to obtain intermediate M32-B with a yield of 55%.

[0232] Preparation of organic compound M-32 containing dibenzofuran group: The preparation method is the same as that of M-4, except that intermediate M32-B is used instead of M4-B and Sub-31-b is used instead of Sub-4-b to obtain organic compound M-32 containing dibenzofuran group, with a yield of 57%.

[0233] Elemental analysis: C51H30DN3O Theoretical values: C, 87.16; H, 4.59; N, 5.98; O, 2.28; Measured values: C, 87.14; H, 4.57; N, 5.99; HRMS(ESI) m / z [M+H]+: Theoretical value: 702.25; Measured value: 703.25.

[0234] Example 15

[0235] This embodiment provides an organic compound M-33 containing a dibenzofuran group. The synthesis of the organic compound M-33 containing a dibenzofuran group specifically includes the following steps:

[0236]

[0237] Preparation of intermediate Sub-33-a: The preparation method is the same as that of Sub-30-a, except that Sub33-A is used instead of Sub30-A to obtain intermediate Sub-33-a with a yield of 59%.

[0238] Preparation of intermediate M33-B: The preparation method is the same as that of M4-B, except that Sub-33-a is used instead of Sub-4-a and SubM33-C is used instead of M4-A to obtain intermediate M33-B with a yield of 57%.

[0239] Preparation of organic compound M-33 containing dibenzofuran group: The preparation method is the same as that of M-4, except that intermediate M33-B is used instead of M4-B and Sub-33-b is used instead of Sub-4-b to obtain organic compound M-33 containing dibenzofuran group, with a yield of 66%.

[0240] Elemental analysis: C47H27D2N3O Theoretical values: C, 86.35; H, 4.78; N, 6.43; O, 2.45; Measured values: C, 86.33; H, 4.76; N, 6.46; HRMS(ESI) m / z [M+H]+: Theoretical value: 653.24; Measured value: 654.24.

[0241] Example 16

[0242] This embodiment provides an organic compound M-47 containing a dibenzofuran group. The synthesis of the organic compound M-47 containing a dibenzofuran group specifically includes the following steps:

[0243]

[0244] After purging the three-necked reaction flask with nitrogen, equipped with a mechanical stirrer, thermometer, and condenser, Sub-1-a (10 mmol), intermediate M47-A (10 mmol), 100 mL tetrahydrofuran, 20 mL water, potassium carbonate (20 mmol), and Pd(PPh3)4 (0.05 mmol) were added sequentially. The mixture was heated to 70–80 °C and reacted for 3 h. The temperature was then lowered to 25–30 °C, and 100 mL of water and 100 mL of toluene were added. The mixture was stirred and separated. The aqueous phase was extracted once with 100 mL of toluene, separated, and the organic phases were combined. 7 g of anhydrous sodium sulfate was added to the organic phase, and the mixture was stirred and dried. The organic phase was filtered and concentrated (-0.08–0.09 MPa, 55–60 °C) until no liquid flowed out. 50 mL of a mixed solvent of dichloromethane and petroleum ether was added with stirring, and the mixture was cooled to 0–5 °C and filtered to obtain compound M47-B in 68% yield.

[0245] After purging the three-necked reaction flask with nitrogen, which is equipped with a mechanical stirrer, thermometer, and condenser, intermediate M47-B (10 mmol), intermediate Sub-47-b (10 mmol), potassium carbonate (20 mmol), Pd(PPh3)4 (0.05 mmol), 100 mL of 1,4-dioxane, and 30 mL of water were added in sequence. The stirring was turned on and the mixture was heated to 70-75 °C for 3 h. Cool to 25–30°C, add 100 mL of water and 100 mL of dichloromethane, stir and separate. Extract the aqueous phase once with 100 mL of dichloromethane, separate, combine the organic phases, add 7 g of anhydrous sodium sulfate to the organic phase, stir and dry, filter, concentrate the organic phase (-0.08–0.09 MPa, 55–60°C) until no liquid flows out, stir and add 20 mL of petroleum ether, cool to 0–5°C, filter to obtain crude product, recrystallize the crude product from toluene to obtain organic compound M-47 containing dibenzofuran group, yield 65%. Elemental analysis: C47H29N3O Theoretical values: C, 86.61; H, 4.49; N, 6.45; O, 2.45; Measured values: C, 86.64; H, 4.48; N, 6.43; HRMS(ESI) m / z [M+H]+: Theoretical value: 651.23; Measured value: 652.22.

[0246] Example 17

[0247] This embodiment provides an organic compound M-53 containing a dibenzofuran group. The synthesis of the organic compound M-53 containing a dibenzofuran group specifically includes the following steps:

[0248]

[0249] After purging the three-necked reaction flask with nitrogen, equipped with a mechanical stirrer, thermometer, and condenser, Sub-1-a (10 mmol), intermediate M53-A (10 mmol), 100 mL tetrahydrofuran, 20 mL water, potassium carbonate (20 mmol), and Pd(PPh3)4 (0.05 mmol) were added sequentially. The mixture was heated to 70–80 °C and reacted for 3 h. The temperature was then lowered to 25–30 °C, and 100 mL of water and 100 mL of toluene were added. The mixture was stirred and separated. The aqueous phase was extracted once with 100 mL of toluene, and the liquid phases were separated and combined. 7 g of anhydrous sodium sulfate was added to the organic phase, and the mixture was stirred and dried. The organic phase was filtered and concentrated (-0.08–0.09 MPa, 55–60 °C) until no liquid flowed out. 50 mL of a mixed solvent of dichloromethane and petroleum ether was added with stirring, and the mixture was cooled to 0–5 °C and filtered to obtain compound M53-B in 68% yield.

[0250] After purging the three-necked reaction flask with nitrogen, which is equipped with a mechanical stirrer, thermometer, and condenser, intermediate M53-B (10 mmol), intermediate Sub-1-b (10 mmol), potassium carbonate (20 mmol), Pd(PPh3)4 (0.05 mmol), 100 mL of 1,4-dioxane, and 30 mL of water were added in sequence. The stirring was turned on and the mixture was heated to 70-75 °C for 3 h. Cool to 25–30°C, add 100 mL of water and 100 mL of dichloromethane, stir and separate. Extract the aqueous phase once with 100 mL of dichloromethane, separate, combine the organic phases, add 7 g of anhydrous sodium sulfate to the organic phase, stir and dry, filter, concentrate the organic phase (-0.08–0.09 MPa, 55–60°C) until no liquid flows out, stir and add 20 mL of petroleum ether, cool to 0–5°C, filter to obtain crude product, recrystallize the crude product from toluene to obtain organic compound M-53 containing dibenzofuran group, yield 61%. Elemental analysis: C47H29N3O Theoretical values: C, 86.61; H, 4.49; N, 6.45; O, 2.45; Measured values: C, 86.64; H, 4.48; N, 6.43; HRMS(ESI) m / z [M+H]+: Theoretical value: 651.23; Measured value: 652.23.

[0251] Example 18

[0252] This embodiment provides an organic compound M-61 containing a dibenzofuran group. The synthesis of the organic compound M-61 containing a dibenzofuran group specifically includes the following steps:

[0253]

[0254] After purging the three-necked reaction flask with nitrogen, equipped with a mechanical stirrer, thermometer, and condenser, Sub-61-a (10 mmol), intermediate M61-A (10 mmol), 100 mL tetrahydrofuran, 20 mL water, potassium carbonate (20 mmol), and Pd(PPh3)4 (0.05 mmol) were added sequentially. The mixture was heated to 70–80 °C and reacted for 3 h. The temperature was then lowered to 25–30 °C, and 100 mL of water and 100 mL of toluene were added. The mixture was stirred and separated. The aqueous phase was extracted once with 100 mL of toluene, and the two phases were separated. The combined organic phases were added to 7 g of anhydrous sodium sulfate, stirred, dried, filtered, and concentrated (-0.08–0.09 MPa, 55–60 °C) until no liquid flowed out. A mixed solvent of dichloromethane and petroleum ether was added with stirring, and the mixture was cooled to 0–5 °C and filtered to obtain compound M61-B in 60% yield.

[0255] After purging the three-necked reaction flask with nitrogen, which is equipped with a mechanical stirrer, thermometer, and condenser, intermediate M61-B (10 mmol), intermediate Sub-1-b (10 mmol), potassium carbonate (20 mmol), Pd(PPh3)4 (0.05 mmol), 100 mL of 1,4-dioxane, and 30 mL of water were added in sequence. The stirring was turned on and the mixture was heated to 70-75 °C for 3 h. Cool to 25–30°C, add 100 mL of water and 100 mL of dichloromethane, stir and separate. Extract the aqueous phase once with 100 mL of dichloromethane, separate, combine the organic phases, add 7 g of anhydrous sodium sulfate to the organic phase, stir and dry, filter, concentrate the organic phase (-0.08–0.09 MPa, 55–60°C) until no liquid flows out, stir and add 20 mL of petroleum ether, cool to 0–5°C, filter to obtain crude product, recrystallize the crude product from toluene to obtain organic compound M-61 containing dibenzofuran group, yield 58%.

[0256] Elemental analysis: C53H33N3O Theoretical values: C, 87.46; H, 4.57; N, 5.77; O, 2.20; Measured values: C, 87.48; H, 4.56; N, 5.77; HRMS(ESI) m / z [M+H]+: Theoretical value: 727.26; Measured value: 727.36.

[0257] Example 19

[0258] This embodiment provides an organic electroluminescent compound M-66. The synthesis of organic compound M-66 containing a dibenzofuran group specifically includes the following steps:

[0259]

[0260] After purging the three-necked reaction flask with nitrogen, equipped with a mechanical stirrer, thermometer, and condenser, Sub-66-a (10 mmol), intermediate M66-A (10 mmol), 100 mL tetrahydrofuran, 20 mL water, potassium carbonate (20 mmol), and Pd(PPh3)4 (0.05 mmol) were added sequentially. The mixture was heated to 70–80 °C and reacted for 3 h. The temperature was then lowered to 25–30 °C, and 100 mL of water and 100 mL of toluene were added. The mixture was stirred and separated. The aqueous phase was extracted once with 100 mL of toluene, and the two phases were separated. The combined organic phases were added to 7 g of anhydrous sodium sulfate, stirred, dried, filtered, and concentrated (-0.08–0.09 MPa, 55–60 °C) until no liquid flowed out. A mixed solvent of dichloromethane and petroleum ether was added with stirring, and the mixture was cooled to 0–5 °C and filtered to obtain compound M66-B in 60% yield.

[0261] After purging the three-necked reaction flask with nitrogen, equipped with a mechanical stirrer, thermometer, and condenser, intermediate M66-B (10 mmol), intermediate Sub-1-b (10 mmol), potassium carbonate (20 mmol), Pd(PPh3)4 (0.05 mmol), 100 mL of 1,4-dioxane, and 30 mL of water were added sequentially. The mixture was stirred and heated to 70–75 °C for 3 h. The temperature was then lowered to 25–30 °C, and 100 mL of water and 100 mL of dichloromethane were added. The mixture was stirred and separated. The aqueous phase was extracted once with 100 mL of dichloromethane, separated, and the organic phases were combined. 7 g of anhydrous sodium sulfate was added to the organic phase, and the mixture was stirred and dried. The organic phase was filtered and concentrated (-0.08–0.09 MPa, 55–60 °C) until no liquid flowed out. 20 mL of petroleum ether was added with stirring, and the temperature was lowered to 0–5 °C. The mixture was filtered to obtain the crude product. The crude product was recrystallized from toluene to obtain product M-66, with a yield of 58%.

[0262] Elemental analysis: C57H35N3O Theoretical values: C, 88.01; H, 4.54; N, 5.40; O, 2.06; Measured values: C, 88.04; H, 4.52; N, 5.40; HRMS(ESI) m / z [M+H]+: Theoretical value: 777.28; Measured value: 777.37.

[0263] Example 20

[0264] This embodiment provides an organic compound M-76 containing a dibenzofuran group. The synthesis of the organic compound M-76 containing a dibenzofuran group specifically includes the following steps:

[0265]

[0266] After purging the three-necked reaction flask with nitrogen, equipped with a mechanical stirrer, thermometer, and condenser, the following were added sequentially: Sub-76-a (10 mmol), intermediate M76-A (10 mmol), 100 mL tetrahydrofuran, 20 mL water, potassium carbonate (20 mmol), and Pd(PPh3)4 (0.05 mmol). The mixture was heated to 70–80 °C and reacted for 3 h. The temperature was then lowered to 25–30 °C, and 100 mL of water and 100 mL of toluene were added. The mixture was stirred and separated. The aqueous phase was extracted once with 100 mL of toluene, and the two phases were separated. The combined organic phases were added, and 7 g of anhydrous sodium sulfate was added and stirred until dry. The mixture was filtered, and the organic phase was concentrated (-0.08–0.09 MPa, 55–60 °C) until no liquid flowed out. A mixed solvent of dichloromethane and petroleum ether was added with stirring, and the mixture was cooled to 0–5 °C and filtered to obtain compound M76-B in 60% yield.

[0267] After purging the three-necked reaction flask with nitrogen, which was equipped with a mechanical stirrer, thermometer, and condenser, intermediate M76-B (10 mmol), intermediate Sub-30-b (10 mmol), potassium carbonate (20 mmol), Pd(PPh3)4 (0.05 mmol), 100 mL of 1,4-dioxane, and 30 mL of water were added sequentially. The mixture was stirred and heated to 70–75 °C for 3 h. The temperature was then lowered to 25–30 °C, and 100 mL of water and 100 mL of dichloromethane were added. The mixture was stirred and separated. The aqueous phase was extracted once with 100 mL of dichloromethane, separated, and the organic phases were combined. 7 g of anhydrous sodium sulfate was added to the organic phase, and the mixture was stirred and dried. The organic phase was filtered and concentrated (-0.08–0.09 MPa, 55–60 °C) until no liquid flowed out. 20 mL of petroleum ether was added with stirring, and the temperature was lowered to 0–5 °C. The mixture was filtered to obtain the crude product. The crude product was recrystallized from toluene to obtain product M-76, with a yield of 64%.

[0268] Elemental analysis: C53H33N3O Theoretical values: C, 87.46; H, 4.57; N, 5.77; O, 2.20; Measured values: C, 87.49; H, 4.56; N, 5.75; HRMS(ESI) m / z [M+H]+: Theoretical value: 727.26; Measured value: 728.37.

[0269] Device Examples

[0270] This embodiment provides an organic electroluminescent device, such as... Figure 1 As shown, the device includes 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, which are sequentially stacked 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).

[0271] The materials used to manufacture the organic electroluminescent device are as follows:

[0272]

[0273] The fabrication of the above-mentioned organic electroluminescent device includes the following steps:

[0274] The glass substrate coated with transparent ITO was ultrasonically treated in an aqueous cleaning agent (the composition and concentration of the aqueous cleaning agent: ethylene glycol solvent ≤10wt%, triethanolamine ≤1wt%), then rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone and ethanol (volume ratio of acetone and ethanol 1:1), baked in a clean environment until all moisture was removed, and then cleaned with ultraviolet light and ozone.

[0275] 2) Preparation of organic layer:

[0276] The ITO transparent substrate was transferred to an evaporation equipment and vacuumed to 1×10⁻⁶. -6 Up to 2×10 -4 Pa, hole injection layer (HIL) / hole transport layer (HTL) / light emission layer (EML) / electron transport layer (ETL) / electron injection layer (EIL) / thick cathode (Al) are sequentially deposited on the anode film.

[0277] in:

[0278] The hole injection layer (HIL) is a mixture of NDP-9 and HT, and the specific mass is shown in Table 1.

[0279] The materials of the hole transport layer (HTL) are shown in Table 1;

[0280] The light-emitting layer (EML) is vacuum-deposited by co-evaporation. The material of the light-emitting layer includes a host material and a guest material, wherein the guest material is (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 1.

[0281] The materials of the electron transport layer (ETL) are shown in Table 1;

[0282] The material of the electron injection layer (EIL) is LiQ;

[0283] The cathode is aluminum;

[0284] Table 1 shows some of the layers, their materials, and thicknesses in organic electroluminescent devices.

[0285] Table 1

[0286]

[0287]

[0288]

[0289]

[0290]

[0291] The examples in the table represent device examples, and the comparative examples in the table are device comparative examples.

[0292] Test case

[0293] The organic electroluminescent devices obtained in Device Examples 1-26 and Comparative Examples 1-3 in the device examples were tested.

[0294] Instruments: The current, voltage, brightness, emission spectrum and other characteristics of the device were tested simultaneously using a PR 650 spectral scanning luminance meter and a Keithley K2400 digital source meter system;

[0295] Test conditions: Photoelectric properties test conditions: current density is 10mA / cm2.

[0296] Lifetime test: The time (in hours) is recorded when the device brightness drops to 95% of its original brightness at a current density of 50mA / cm2.

[0297] The device performance test results are shown in Table 2:

[0298] Table 2

[0299]

[0300]

[0301] The light-emitting host material in this invention includes an organic compound containing a dibenzofuran group having the structure of formula (1) and an organic electroluminescent compound having the structure of formula (2). Compared with the combination of A, B, etc. disclosed in the prior art, it has significantly better performance and can have a lower driving voltage after being fabricated into a device.

[0302] Obviously, the above embodiments are merely illustrative examples for clear explanation and are not intended to limit the implementation. Those skilled in the art will recognize that other variations or modifications can be made based on the above description. It is neither necessary nor possible to exhaustively list all possible implementations here. However, obvious variations or modifications derived therefrom are still within the scope of protection of this invention.

Claims

1. An organic compound containing a dibenzofuran group, characterized in that, It has the structure shown in equation (1): Ar1 is selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; Ar2-Ar3 are each independently selected from substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups; The substituents in the substituted C6-C30 aryl and substituted C3-C30 heteroaryl groups are each independently selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl.

2. The organic compound containing a dibenzofuran group according to claim 1, characterized in that, Ar1 is selected from hydrogen, deuterium, substituted or unsubstituted C6-C15 aryl groups; In this case, each substituent in the substituted C6-C15 aryl group is independently selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl. Preferably, Ar1 is selected from hydrogen, deuterium, and phenyl.

3. The organic compound containing a dibenzofuran group according to claim 1 or 2, characterized in that, Ar2 is selected from substituted or unsubstituted C6-C15 aryl groups; In this case, each substituent in the substituted C6-C15 aryl group is independently selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl. Preferably, Ar2 is selected from substituted or unsubstituted phenyl groups or substituted or unsubstituted naphthyl groups; wherein the substituents in the substituted phenyl groups or substituted naphthyl groups are selected from deuterium or C1-C6 alkyl groups.

4. The organic compound containing a dibenzofuran group according to any one of claims 1-3, characterized in that, Ar3 is selected from substituted or unsubstituted C6-C20 aryl groups and substituted or unsubstituted C3-C20 heteroaryl groups; The substituents in the substituted C6-C20 aryl and substituted C3-C20 heteroaryl are selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl. Preferably, Ar3 is selected from substituted or unsubstituted A groups, and the A group is selected from phenyl, naphthyl, biphenyl, terphenyl, dibenzofuranyl, carbazoleyl, and phenylcarbazoleyl. Wherein, the substituents in the substituted A group are selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl. Preferably, Ar3 is selected from phenyl, naphthyl, biphenyl, terphenyl, dibenzofuranyl, carbazolyl, phenylcarbazolyl, 1-deuterium-substituted phenyl, 1-deuterium-substituted naphthyl, 2-deuterium-substituted phenyl, and 5-deuterium-substituted phenyl.

5. The organic compound containing a dibenzofuran group according to any one of claims 1-4, characterized in that, Equation (1) is selected from one of the structures shown in Equations 1-1 to 1-28 below: The definitions of Ar1-Ar3 are the same as in claim 1; Preferably, the formula (1) is selected from formula 1-1, formula 1-17, and formula 1-19.

6. The organic compound containing a dibenzofuran group according to any one of claims 1-5, characterized in that, The organic compound containing dibenzofuran group is selected from any one of the following M-1 to M-77:

7. A luminescent host material, characterized in that, It includes a first host material and a second host material, wherein the first host material is an organic compound containing a dibenzofuran group as described in any one of claims 1-6; and the second host material is an organic electroluminescent compound having the structure of the following formula (2): Where X is selected from O and S; L'、L 1’ L 2’ Each is independently selected from the linking bond, substituted or unsubstituted C6-C30 arylene, or substituted or unsubstituted C3-C30 heteroarylene; Ar 1’ Ar 2’ Ar is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 aromatic amino, substituted or unsubstituted C3-C60 heteroaryl, and substituted or unsubstituted C3-C60 heteroaryl.

8. The light-emitting host material according to claim 7, characterized in that, In the above equation (2), Ar 1’ Ar 2’ Ar is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C6-C15 aryl, substituted or unsubstituted C6-C18 arylamine, substituted or unsubstituted C3-C18 heteroaryl, and substituted or unsubstituted C3-C18 heteroaryl. Wherein, the substituents in the substituted C6-C15 aryl, substituted C6-C18 arylamine, substituted C3-C18 heteroaryl, and substituted C3-C18 heteroaryl are each independently selected from one or a combination of at least two of the following: alkyl of C1-C6, cycloalkyl of C3-C12, aryl of C6-C25, heteroaryl of C3-C25, arylamine of C6-C60, and heteroaryl of C3-C60. Preferably, the Ar 1’ Ar 2’ Ar and Ar are each independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted E groups, wherein the E groups are selected from the following groups: phenyl, naphthyl, biphenyl, phenanthrene, fluoranyl, ... alkyl, triphenyl, triphenylene, phenylnaphthyl, naphthylphenyl, dimethylfluorenyl, phenylmethylfluorenyl, diphenylfluorenyl, pyridyl, pyridylphenyl, phenylpyridyl, spirodifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirodifluorenyl, dibenzofuranyl, benzonaphthuryl, benzonaphthiophenyl, dibenzothiophenyl, diphenylamino, N,N-diphenylaniline; Wherein, each of the substituents in the substituted E group is independently selected from one or a combination of at least two of the following: alkyl (C1-C6), cycloalkyl (C3-C12), aryl (C6-C25), heteroaryl (C3-C25), arylamine (C6-C60), and heteroarylamine (C3-C60). Preferred, Ar 1’ -Ar 2’ Each is independently selected from phenyl, naphthyl, biphenyl, yl, triphenyl, phenylnaphthyl, naphthylphenyl, dimethylfluorenyl, diphenylfluorenyl, pyridyl, pyridylphenyl, phenylpyridyl, phenylcarbazolyl, phenylbenzocarbazolyl, phenylphenanthrocarbazolyl, spirodifluorenyl, spiro[fluoren-9,9'-oxanthracene]yl, phenylmethylfluorenyl, dibenzofuranyl, benzonaphthofuryl, diphenylamino, N,N-diphenylaniline; Preferably, Ar is selected from phenyl or naphthyl; The Ar 1’ Ar 2’ The radicals are independently selected from phenyl, naphthyl, dibenzofuranyl, benzonaphthofuranyl, diphenylamino, and N,N-diphenylaniline. Preferably, L', L 1’ L 2’ Each is independently selected from the linking bond, substituted or unsubstituted C6-C12 arylene, or substituted or unsubstituted C3-C12 heteroarylene; The substituents of the substituted C6-C12 arylene and the substituted C3-C12 heteroarylene are each independently selected from one or a combination of at least two of the following: alkyl groups of C1-C6, cycloalkyl groups of C3-C12, aryl groups of C6-C25, heteroaryl groups of C3-C25, aryl groups of C6-C60, and heteroaryl groups of C3-C60. Preferably, L' is selected from naphthylene; Preferred, L 1’ L 2’ Each is independently selected from the linking bond, phenylene, and naphthylene; Preferably, X is selected from O.

9. The light-emitting host material according to claim 7 or 8, characterized in that, Organic electroluminescent compounds having the structure of formula (2) are selected from one of the following N-1 to N-654:

10. The light-emitting host material according to any one of claims 7-9, characterized in that, The mass ratio of the first main material to the second main material is 9:1 to 1:9; Preferably, the mass ratio of the first main material to the second main material is 2:8-8:2; More preferably, the mass ratio of the first main material to the second main material is 3:7-7:3; More preferably, the mass ratio of the first main material to the second main material is 4:6-6:

4.

11. An organic electroluminescent material, characterized in that, The organic electroluminescent material includes any one of the organic compounds containing dibenzofuran groups according to claims 1-6 or the luminescent host material according to any one of claims 7-10.

12. 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, wherein the organic layer comprises the organic electroluminescent compound of any one of claims 1-6, the light-emitting host material of any one of claims 7-10, or the organic electroluminescent material of claim 11.

13. The application of the organic electroluminescent device of claim 12 in optical fiber equipment, lighting equipment, electrophotographic photosensitive equipment, photoelectric converters, organic solar cells, switching element equipment, organic light-emitting field-effect transistors, image sensors or dye lasers.

Images