Boron-nitrogen compound and organic electroluminescent device comprising same

Abstract

The invention relates to the technical field of preparation of organic photoelectric materials, in particular to a boron-nitrogen compound and an organic electroluminescent device comprising the same. The boron-nitrogen compound provided by the invention has carrier transport capability, and can effectively inhibit interaction among luminescent molecules. And meanwhile, the energy transmission performance between a subject and an object or a sensitizer can be improved by the large conjugated structural unit. Specifically, the boron-nitrogen compound provided by the invention is used as a functional layer, especially as an organic electroluminescent device manufactured by a luminescent layer, the current efficiency is improved, the lighting voltage is reduced, and meanwhile, the service life of the device is greatly prolonged.

Description

Technical Field

[0001] The invention relates to the technical field of organic photoelectric material preparation, and in particular to a boron nitrogen compound and an organic electroluminescent device containing the same. Background Art

[0002] With the development of multimedia technology and the improvement of information requirements, the requirements for panel display performance are getting higher and higher. Among them, OLED has a series of advantages such as autonomous luminescence, low-voltage DC drive, full curing, wide viewing angle, rich colors, etc., and has attracted widespread attention for its potential application in the new generation of display and lighting technology, and its application prospects are very broad. Organic electroluminescent devices are spontaneous luminescent devices. The mechanism of OLED luminescence is that under the action of an external electric field, electrons and holes are injected from the positive and negative electrodes respectively, and then migrate, recombine and decay in the organic material to produce luminescence. The typical structure of OLED includes one or more functional layers of cathode layer, anode layer, electron injection layer, electron transport layer, hole blocking layer, hole transport layer, hole injection layer and light-emitting layer. Although the research progress of organic electroluminescence is very rapid, there are still many problems to be solved. For example, high-efficiency, long-life, narrow-emission green light materials have always been a problem to be solved by technicians in this field. Summary of the invention

[0003] The purpose of the present invention is to provide a boron nitrogen compound and an organic electroluminescent device containing the same in view of the deficiencies in the prior art. The present invention effectively suppresses the interaction between luminescent molecules by introducing a spirocyclic large steric hindering group. By introducing a large conjugated structure to improve the carrier transport capacity of the boron nitrogen compound, the energy transfer performance between the host and the guest can be improved, and the concentration of high-energy excitons in the light-emitting layer can be reduced, thereby realizing a highly efficient, long-life, narrow-emission green light material.

[0004] In order to achieve the purpose of the present invention, the technical solution of the present invention is as follows:

[0005] According to one or more embodiments, the present invention provides a boron nitrogen compound having a general structure shown in the following formula I;

[0006] In Formula I, Ring A and Ring B are each independently selected from C6-C30 aryl and C6-C30 nitrogen heteroaryl, and Ring A or Ring B are not simultaneously selected from C6-C30 nitrogen heteroaryl; R1-R7 are monosubstituted or polysubstituted; R1 is selected from hydrogen, deuterium, C1-C24 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; when containing substitution, the substitution is selected from deuterium, C1-C24 alkyl, C3-C24 cycloalkyl, C R2-R4 are each independently selected from hydrogen, deuterium, C1-C24 alkyl; R5-R6 are each independently selected from C1-C24 alkyl, C3-C24 cycloalkyl, substituted or unsubstituted C6-C30 aryl, or R5 and R6 form a saturated or unsaturated C3-C15 membered ring with the carbon atom to which they are commonly attached; R7 is selected from hydrogen, deuterium, C1-C24 alkyl substituted or unsubstituted C6-C30 aryl, C5-C30 nitrogen heteroaryl.

[0007] Preferably, ring A is selected from phenyl and naphthyl, and ring B is selected from phenyl, naphthyl, pyridyl, quinolyl or quinoxalinyl.

[0008] Preferably, the R1 is monosubstituted, and R1 is selected from hydrogen, deuterium, C1-C12 alkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C2-C18 heteroaryl; when it contains substitution, the substitution is selected from one or more of deuterium, tert-butyl, adamantyl, and phenyl.

[0009] More preferably, R1 is selected from one or more of hydrogen, deuterium, tert-butyl, phenyl, biphenyl, tert-butylphenyl, tert-butylbiphenyl, terphenyl, pyridyl, 4-phenylpyridyl, dibenzofuranyl, dibenzothienyl, dimethylfluorenyl, diphenyltriazine, and adamantyl-substituted phenyl.

[0010] Preferably, R2, R3, and R4 are each the same or different and are selected from deuterium, methyl, ethyl, propyl, and tert-butyl.

[0011] R5-R6 are independently the same or different and are selected from methyl, phenyl, tert-butylphenyl, or R5 and R6 are linked to form a cyclopentyl, cyclohexyl or fluorene ring.

[0012] Preferably, R7 is selected from hydrogen, deuterium, phenyl, tert-butylphenyl, carbazolyl; more preferably, when ring B is selected from pyridyl, quinolyl or quinoxalinyl, R7 is selected from hydrogen or deuterium.

[0013] Preferably, the hydrogen atoms in Formula I of the present invention may be partially or completely replaced by deuterium.

[0014] According to one or more embodiments, the present invention provides a boron nitrogen compound, wherein the boron nitrogen compound is selected from any one of the chemical structures shown below, wherein "D" represents deuterium: .

[0015] According to one or more embodiments, the present invention also provides the use of a boron nitrogen compound having a general structure as shown in Formula I above in the preparation of an electronic device.

[0016] Furthermore, the electronic devices include organic electroluminescent devices (OLEDs), organic integrated circuits (O-ICs), organic field effect transistors (O-FETs), organic thin film transistors (O-TFTs), organic light emitting transistors (O-LETs), organic solar cells (O-SCs), organic photoelectric devices, organic optical detectors, organic photoreceptors, organic field quenching devices (O-FQDs), light emitting electrochemical cells (LECs), and organic laser diodes (O-lasers).

[0017] According to one or more embodiments, the present invention further provides an organic electroluminescent device, comprising a cathode, an anode and an organic functional layer therebetween; the organic functional layer comprises a boron nitrogen compound having a general structure as shown in Formula I above.

[0018] Furthermore, the organic functional layer further comprises a light-emitting layer, and the light-emitting layer comprises a boron-nitrogen compound having a general structure as shown in the above formula I. Preferably, the mass percentage of the boron-nitrogen compound is 0.1%-50%.

[0019] According to one or more embodiments, the present invention also provides an organic photoelectric device, comprising a first electrode; a second electrode facing the first electrode; and a light-emitting material layer disposed between the first electrode and the second electrode, wherein the light-emitting material layer comprises a boron nitrogen compound having a general structure as shown in the above formula I. For example, the boron nitrogen compound can be included in the light-emitting material layer as a dopant.

[0020] According to one or more embodiments, the present invention further provides a composition comprising a boron nitrogen compound having a general structure as shown in Formula I above.

[0021] According to one or more embodiments, the present invention also provides a preparation, the preparation comprising a boron nitrogen compound having a general structure as shown in Formula I above or a composition as described above and at least one solvent. The solvent is not particularly limited, and those skilled in the art may use, for example, unsaturated hydrocarbon solvents, halogenated saturated hydrocarbon solvents, halogenated unsaturated hydrocarbon solvents, ether solvents or ester solvents; wherein the unsaturated hydrocarbon solvent is toluene, xylene, mesitylene, tetralin, n-butylbenzene, sec-butylbenzene or tert-butylbenzene; the halogenated saturated hydrocarbon solvent is carbon tetrachloride, chloroform, dichloromethane, dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, hexyl chloride, bromohexane, chlorocyclohexane or bromocyclohexane; the halogenated unsaturated hydrocarbon solvent is chlorobenzene, dichlorobenzene or trichlorobenzene; the ether solvent is tetrahydrofuran or tetrahydropyran; the ester solvent is an alkyl benzoate.

[0022] According to one or more embodiments, the present invention further provides a display device, which includes one or more of the organic electroluminescent device or organic photoelectric device as described above.

[0023] According to one or more embodiments, the present invention further provides a lighting device, which comprises one or more of the organic electroluminescent device or organic photoelectric device as described above.

[0024] Compared with the prior art, the present invention has the following beneficial effects:

[0025] The present invention provides a boron nitrogen compound with good electron and hole receiving ability. The present invention can effectively inhibit the interaction between luminescent molecules by introducing a large sterically hindered spiro ring and a monosubstituted spiro ring group. The large conjugated fused ring structure and the monosubstituted dibenzofuran, dibenzothiophene, biphenyl, fluorenyl and other structural units can make the compound have the ability to enhance the energy transfer performance between the host and the guest (or sensitizer). Specifically, the organic electroluminescent device made of the boron nitrogen compound of the present invention as a functional layer, especially as a light-emitting layer, has a good current efficiency improvement effect, and the life of the device is also greatly improved. It shows that after most electrons and holes recombine, the energy is effectively transferred to the boron nitrogen compound, thereby achieving high luminous efficiency. DETAILED DESCRIPTION

[0026] The content of the present invention is described in detail below. The description of the constituent elements recorded below is sometimes based on representative embodiments or specific examples of the present invention, but the present invention is not limited to such embodiments or specific examples. By referring to the following specific embodiments and the examples contained therein, the present disclosure can be more easily understood. Before disclosing and describing the compounds, devices and / or methods of the present invention, it should be understood that, unless otherwise stated, they are not limited to specific synthetic methods or specific reagents, because this can be varied. It should also be understood that the terms used in the present invention are only used to describe specific aspects and are not intended to be limiting. Although any methods and materials similar or equivalent to those described in the present invention can be used in the practice or test, exemplary methods and materials are now described.

[0027] The term "alkyl" as used herein refers to a monovalent alkyl group having 1 to 24 carbon atoms, preferably 1 to 12 carbon atoms, more preferably 1 to 6 carbon atoms. Examples of this term include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-hexyl, etc.

[0028] The "cycloalkyl" of the present invention refers to a cyclic alkyl group having 3 to 24 carbon atoms and a monocyclic or polycyclic condensed ring, preferably 3 to 12 carbon atoms, which can be substituted by 1 to 3 alkyl groups at will. Such cycloalkyl groups include, for example, monocyclic structures such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexane, cyclooctyl, 1-methylcyclopropyl, 2-methylcyclopentyl, 2-methylcyclooctyl, methylcyclohexane, etc., or polycyclic structures such as adamantyl, etc.

[0029] The "aryl" of the present invention refers to an unsaturated aromatic carbocyclic ring having 6-30 carbon atoms and having a monocyclic (such as phenyl) or polycyclic condensation (such as naphthyl or anthracenyl), preferably having 6-18 carbon atoms, more preferably 1-12 carbon atoms. Preferred aryl groups include phenyl, biphenyl, naphthyl, phenanthrenyl, terphenyl, etc. Unless otherwise defined for individual substituents, such aryl groups may be optionally substituted by 1-3 of the following substituents: hydroxyl, acyl, acyloxy, alkyl, alkoxy, alkenyl, alkynyl, amino, aminoacyl, aryl, aryloxy, carboxyl, carboxyl ester, aminocarboxyl ester, cyano, halogen, nitro, heteroaryl, heterocycle, thioalkoxy, trihalomethyl, etc. Preferred substituents include alkyl, alkoxy, halogen, cyano, nitro, trihalomethyl and thioalkoxy. But not limited thereto.

[0030] The "heteroaryl" mentioned in the present invention refers to a general term for a group having 2-30 carbon atoms and one or more aromatic carbon atoms in the aromatic group are replaced by a heteroatom, preferably 5-18 carbon atoms, and the heteroatom includes but is not limited to oxygen (O), sulfur (S) or nitrogen (N), silicon (Si) or germanium (Ge) atoms. The heteroaryl group can be a monocyclic heteroaryl group or a condensed ring heteroaryl group. Examples may include pyridyl, pyrrolyl, pyridyl, thienyl, furanyl, indolyl, quinolyl, isoquinolyl, quinoxalinyl, triazine, benzothienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, etc., but are not limited thereto.

[0031] The substitution in the present invention may be by a single bond or by fusion.

[0032] As used in the specification and the appended claims, the singular forms "a", "an" and "the" include plural referents unless the context clearly dictates otherwise. Thus, for example, reference to "a component" includes a mixture of two or more components.

[0033] Unless otherwise stated, all commercial reagents involved in the following experiments were used directly after purchase.

[0034] In a preferred embodiment of the present invention, the OLED device of the present invention contains a hole transport layer, and the hole transport material can be preferably selected from known or unknown materials, and is particularly preferably selected from the following structures, but it does not mean that the present invention is limited to the following structures (Ph is phenyl): .

[0035] In a preferred embodiment of the present invention, the hole injection layer contained in the OLED device of the present invention. The preferred hole injection layer material of the present invention is the following structure, but it does not mean that the present invention is limited to the following structure: .

[0036] In a preferred embodiment of the present invention, the electron transport layer can be selected from at least one of the following compounds, but it does not mean that the present invention is limited to the following structures: .

[0037] The preparation method of the boron nitrogen compound and the luminescent properties of the device are explained in detail in conjunction with the following examples. The molecular structure formula of the relevant material is shown below:

[0038] Example 1: Synthesis of Compound 1

[0039] (1) Synthesis of compound 1-3: Compound 1-1 (279 mg, 1 mmoL) and compound 1-2 (334 mg, 1 mmoL) were dissolved in 50 mL DMF solution, and potassium carbonate (691 mg, 5 mmoL) was added. The reaction system was heated at 140°C for 36 hours and then cooled to room temperature. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3×100 mL). The organic phase was washed with water and dried with sodium sulfate. The solvent was removed by vacuum distillation, and the resulting crude product was separated and purified by silica gel chromatography with dichloromethane: petroleum ether (1:8) as the eluent to obtain product 1-3 (498 mg, yield 84%). Mass spectrum m / z, theoretical value 592.99; measured value M+H: 594.01.

[0040] (2) Synthesis of compound 1-5: BuLi (0.5 mL, 1 mmoL, 2M in hexane) was slowly added to a solution of compound 1-3 (593 mg, 1 mmoL) in anhydrous THF (50 mL) at -78°C. After 3 hours of reaction, 1-4 (180 mg, 1 mmoL) was slowly added. After slowly warming to room temperature, the reaction was allowed to proceed overnight, and 1 mL of ice water was added. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3×100 mL). The organic phase was washed with water and dried over sodium sulfate. The solvent was removed by vacuum distillation, and the residue was dissolved in acetic acid (100 mL), and concentrated hydrochloric acid (10 mL) was added dropwise. The reaction system was refluxed overnight and then cooled to room temperature. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3×100 mL). The organic phase was washed with water and dried over sodium sulfate. The solvent was removed by distillation under reduced pressure, and the crude product was separated and purified by silica gel chromatography with dichloromethane: petroleum ether (1:2) as the eluent to obtain product 1-5 (321 mg, yield 51%). Mass spectrum m / z, theoretical value 629.15; found value M+H: 630.17.

[0041] (3) Synthesis of compound 1-7: Compound 1-5 (629 mg, 1 mmoL) and compound 1-6 (339 mg, 1 mmoL) were dissolved in 50 mL toluene solution. Under nitrogen atmosphere, sodium tert-butoxide (192 mg, 2 mmoL), palladium acetate (12 mg, 0.05 mmoL), and tri-tert-butylphosphine tetrafluoroborate (145 mg, 0.5 mmoL) were added. The reaction system was refluxed for 36 hours and then cooled to room temperature. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3×100 mL). The organic phase was washed with water and dried with sodium sulfate. The solvent was removed by vacuum distillation, and the resulting crude product was separated and purified by silica gel chromatography with dichloromethane: petroleum ether (1:3) as the eluent to obtain product 1-7 (312 mg, yield 35%). Mass spectrum m / z, theoretical value 888.42; measured value M+H: 889.45.

[0042] (4) Synthesis of compound 1: Under nitrogen atmosphere and zero temperature, tert-butyl lithium (1.25 mL, 1.6 M pentane solution, 2 mmoL) was slowly added dropwise to a solution of compound 1-7 (888 mg, 1 mmoL) in tert-butylbenzene (100 mL). After the system was reacted at 60 °C for 4 hours, the temperature was lowered to -50 °C, and then BBr3 (494 mg, 2 mmoL) was added. After reacting at room temperature for 1 hour, N,N-diisopropylethylamine (259 mg, 2 mmoL) was added. The temperature was then raised to 120 °C for 12 hours. After cooling to room temperature, 5 mL of sodium acetate aqueous solution (1 M) was added. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3 × 100 mL). The organic phase was washed with water and dried over sodium sulfate. The solvent was removed by distillation under reduced pressure, and the crude product was separated and purified by silica gel chromatography with dichloromethane: petroleum ether (1:3) as the eluent to obtain product 1 (205 mg, yield 24%). Mass spectrum m / z, theoretical value 862.45; measured value M+H: 863.47.

[0043] Example 2: Synthesis of Compound 5 Compound 5 was prepared by referring to the preparation scheme of Example 1. The yield of the final product was 23%. Mass spectrum m / z, theoretical value 1062.51; measured value M+H: 1063.54.

[0044] Example 3: Synthesis of Compound 10 Compound 10 was prepared by referring to the preparation scheme of Example 1. The yield of the final product was 21%. Mass spectrum m / z, theoretical value 943.51; measured value M+H: 944.52.

[0045] Example 4: Synthesis of Compound 13 Compound 13 was prepared by referring to the preparation scheme of Example 1. The yield of the final product was 20%. Mass spectrum m / z, theoretical value 939.47; measured value M+H: 940.48.

[0046] Example 5: Synthesis of Compound 19 Compound 19 was prepared by referring to the preparation scheme of Example 1. The yield of the final product was 26%. Mass spectrum m / z, theoretical value 912.46; measured value M+H: 913.48.

[0047] Example 6: Synthesis of Compound 22 Compound 22 was prepared by referring to the preparation scheme of Example 1. The yield of the final product was 23%. Mass spectrum m / z, theoretical value 978.47; measured value M+H: 979.48.

[0048] Example 7: Synthesis of Compound 25 Compound 25 was prepared by referring to the preparation scheme of Example 1. The yield of the final product was 22%. Mass spectrum m / z, theoretical value 1040.52; measured value M+H: 1041.55.

[0049] Example 8: Synthesis of Compound 26 Compound 26 was prepared by referring to the preparation scheme of Example 1. The yield of the final product was 21%. Mass spectrum m / z, theoretical value 1162.54; measured value M+H: 1163.65.

[0050] Example 9: Synthesis of Compound 28 Compound 28 was prepared by referring to the preparation scheme of Example 1. The yield of the final product was 21%. Mass spectrum m / z, theoretical value: 1093.53; measured value: M+H: 1094.54.

[0051] Example 10: Synthesis of Compound 34 Compound 34 was prepared by referring to the preparation scheme of Example 1. The yield of the final product was 27%. Mass spectrum m / z, theoretical value: 1090.54; measured value: M+H: 1091.57.

[0052] Example 11: Synthesis of Compound 36 Compound 36 was prepared by referring to the preparation scheme of Example 1. The yield of the final product was 29%. Mass spectrum m / z, theoretical value: 1091.54; measured value: M+H: 1092.57.

[0053] Example 12: Synthesis of Compound 38 Compound 38 was prepared by referring to the preparation scheme of Example 1. The yield of the final product was 20%. Mass spectrum m / z, theoretical value 1202.54; measured value M+H: 1203.56.

[0054] Example 13: Synthesis of Compound 40 Compound 40 was prepared by referring to the preparation scheme of Example 1. The yield of the final product was 22%. Mass spectrum m / z, theoretical value 1014.51; measured value M+H: 1015.54.

[0055] Example 14: Synthesis of Compound 48 Compound 48 was prepared by referring to the preparation scheme of Example 1. The yield of the final product was 23%. Mass spectrum m / z, theoretical value: 1178.57; measured value: M+H: 1179.58.

[0056] Example 15: Synthesis of Compound 49 Compound 49 was prepared by referring to the preparation scheme of Example 1. The yield of the final product was 24%. Mass spectrum m / z, theoretical value 938.48; measured value M+H: 939.51.

[0057] Example 16: Synthesis of Compound 52 Compound 52 was prepared by referring to the preparation scheme of Example 1. The yield of the final product was 26%. Mass spectrum m / z, theoretical value 988.49; found value M+H: 989.50.

[0058] Example 17: Synthesis of Compound 55 Compound 55 was prepared by referring to the preparation scheme of Example 1. The yield of the final product was 21%. Mass spectrum m / z, theoretical value 943.50; measured value M+H: 944.53.

[0059] Example 18: Synthesis of Compound 60 Compound 60 was prepared by referring to the preparation scheme of Example 1. The yield of the final product was 22%. Mass spectrum m / z, theoretical value 1168.50; measured value M+H: 1169.52.

[0060] Example 19: Synthesis of Compound 66 Compound 66 was prepared by referring to the preparation scheme of Example 1. The yield of the final product was 23%. Mass spectrum m / z, theoretical value 1048.59; measured value M+H: 1049.65.

[0061] Example 20: Synthesis of Compound 71 Compound 71 was prepared by referring to the preparation scheme of Example 1. The yield of the final product was 20%. Mass spectrum m / z, theoretical value 1066.54; measured value M+H: 1067.56.

[0062] Example 21: Synthesis of Compound 73 Compound 73 was prepared by referring to the preparation scheme of Example 1. The yield of the final product was 20%. Mass spectrum m / z, theoretical value 1022.57; measured value M+H: 1023.59.

[0063] Example 22: Synthesis of Compound 79 Compound 79 was prepared by referring to the preparation scheme of Example 1. The yield of the final product was 23%. Mass spectrum m / z, theoretical value 863.44; measured value M+H: 864.47.

[0064] Example 23: Synthesis of Compound 84 Compound 84 was prepared by referring to the preparation scheme of Example 1. The yield of the final product was 22%. Mass spectrum m / z, theoretical value 1098.60; measured value M+H: 1099.66.

[0065] Example 24: Synthesis of Compound 87 Compound 87 was prepared by referring to the preparation scheme of Example 1. The yield of the final product was 35%. Mass spectrum m / z, theoretical value 991.50; measured value M+H: 992.51.

[0066] Example 25: Synthesis of Compound 88 Compound 88 was prepared by referring to the preparation scheme of Example 1. The yield of the final product was 22%. Mass spectrum m / z, theoretical value: 1032.46; measured value: M+H: 1033.48.

[0067] Example 26: Synthesis of Compound 90 Compound 90 was prepared by referring to the preparation scheme of Example 1. The yield of the final product was 26%. Mass spectrum m / z, theoretical value: 1090.52; found value: M+H: 1091.53.

[0068] Example 27: Synthesis of Compound 91 Compound 91 was prepared by referring to the preparation scheme of Example 1. The yield of the final product was 21%. Mass spectrum m / z, theoretical value: 1200.65; measured value: M+H: 1201.67.

[0069] Example 28: Synthesis of Compound 93 Compound 93 was prepared by referring to the preparation scheme of Example 1. The yield of the final product was 24%. Mass spectrum m / z, theoretical value: 1088.52; measured value: M+H: 1089.54.

[0070] Example 29: Synthesis of Compound 96 Compound 96 was prepared by referring to the preparation scheme of Example 1. The yield of the final product was 20%. Mass spectrum m / z, theoretical value 993.53; found value M+H: 994.56.

[0071] Example 30: Synthesis of Compound 100 Compound 100 was prepared by referring to the preparation scheme of Example 1. The yield of the final product was 23%. Mass spectrum m / z, theoretical value 1004.52; measured value M+H: 1005.55.

[0072] Example 31: Synthesis of Compound 103 Compound 103 was prepared by referring to the preparation scheme of Example 1. The yield of the final product was 25%. Mass spectrum m / z, theoretical value 964.49; found value M+H: 965.50.

[0073] Example 32: Synthesis of Compound 108 Compound 108 was prepared by referring to the preparation scheme of Example 1. The yield of the final product was 27%. Mass spectrum m / z, theoretical value: 1057.46; found value: M+H: 1058.49.

[0074] Example 33: Synthesis of Compound 115 Compound 115 was prepared by referring to the preparation scheme of Example 1. The yield of the final product was 24%. Mass spectrum m / z, theoretical value: 1090.54; found value: M+H: 1091.57.

[0075] Example 34: Synthesis of Compound 123 Compound 123 was prepared by referring to the preparation scheme of Example 1. The yield of the final product was 22%. Mass spectrum m / z, theoretical value: 1152.52; measured value: M+H: 1153.54.

[0076] Example 35: Synthesis of Compound 130 Compound 130 was prepared by referring to the preparation scheme of Example 1. The yield of the final product was 22%. Mass spectrum m / z, theoretical value 893.48; measured value M+H: 894.51.

[0077] Example 36: Synthesis of Compound 133 Compound 133 was prepared by referring to the preparation scheme of Example 1. The yield of the final product was 25%. Mass spectrum m / z, theoretical value 994.54; found value M+H: 995.56.

[0078] Example 37: Synthesis of Compound 139 Compound 139 was prepared by referring to the preparation scheme of Example 1. The yield of the final product was 24%. Mass spectrum m / z, theoretical value: 1043.51; measured value: M+H: 1044.53.

[0079] Example 38: Synthesis of Compound 146 Compound 146 was prepared by referring to the preparation scheme of Example 1. The yield of the final product was 23%. Mass spectrum m / z, theoretical value 987.47; found value M+H: 988.49.

[0080] Example 39: Synthesis of Compound 148 Compound 148 was prepared by referring to the preparation scheme of Example 1. The yield of the final product was 26%. Mass spectrum m / z, theoretical value 888.46; measured value M+H: 889.47.

[0081] Example 40: Synthesis of Compound 159 Compound 159 was prepared by referring to the preparation scheme of Example 1. The yield of the final product was 25%. Mass spectrum m / z, theoretical value 1129.65; measured value M+H: 1130.68.

[0082] Fabrication of OLED devices:

[0083] As a reference preparation method for a device embodiment, the present invention evaporates a p-doped material on the surface of an ITO glass with a light-emitting area of ​​2 mm×2 mm or on an anode, or co-evaporates the p-doped material with a hole transport material at a concentration of 1% to 50% to form a 5-100 nm hole injection layer (HIL), forms a 5-200 nm hole transport layer (HTL) on the hole injection layer, and then co-evaporates a host material (GH-1 and GH-2), GD-Ir and a boron nitrogen compound prepared by the present invention on the hole transport layer in a mass ratio of 61:35:3:1 to form a 10-100 nm light-emitting layer (EML), and finally co-evaporates to form a 30 nm electron transport layer (ETL), and then evaporates 70 nm of cathode Al, thereby manufacturing an organic electroluminescent diode.

[0084] In a preferred specific embodiment, the structure of the bottom-emitting OLED device provided by the present invention is: glass containing ITO is used as the anode, and HIL is HT-15:P-3 (mass ratio 97:3) evaporated in sequence, with a thickness of 10 nm; HTL is HT-15, with a thickness of 60 nm; EBL is HT-16, with a thickness of 20 nm, EML is (GH-1:GH-2:GD-Ir:Compound 1 (mass ratio 61:35:3:1), with a thickness of 35 nm, ETL is ET-8:LiQ (mass ratio 50:50), with a thickness of 30 nm; EIL is a 1 nm LiF layer; then cathode Al is evaporated to 70 nm to prepare an organic electroluminescent diode, which is recorded as Application Example 1.

[0085] Referring to the device structure provided in Application Example 1, the boron nitrogen compounds listed in Table 1 were selected as the implementation objects to replace Compound 1 to prepare organic electroluminescent diodes, which were respectively recorded as Application Examples 2 to Application Examples 23 and Comparative Example 1. The current efficiency and life of the device application examples and comparative examples prepared above were tested by standard methods, and the device luminescence characteristic data are shown in Table 1.

[0086] .

[0087] As can be seen from Table 1, the compounds of the present invention have higher current efficiency and lifespan after being prepared into electronic devices as light-emitting layer materials. Compared with Comparative Example 1, Application Examples 1 to 23 all show good device performance in terms of current efficiency and lifespan, and the improvement in the performance of each device is achieved based on the excellent electron transmission ability of the boron nitrogen compound material of the present invention. This shows that the boron nitrogen compound provided by the present invention has certain commercial application value.

[0088] The above description is only a preferred specific implementation manner of the present invention, but the protection scope of the present invention is not limited thereto. Any technician familiar with the technical field can make equivalent replacements or changes according to the technical scheme and inventive concept of the present invention within the technical scope disclosed by the present invention, which should be covered by the protection scope of the present invention.

Claims

1. A boron-nitrogen compound, characterized in that: The boron nitrogen compound has a general structure shown in the following formula I: ; In Formula I, Ring A and Ring B are each independently selected from C6-C30 aryl and C6-C30 nitrogen heteroaryl, and Ring A or Ring B are not simultaneously selected from C6-C30 nitrogen heteroaryl; R1-R7 are monosubstituted or polysubstituted; R1 is selected from hydrogen, deuterium, C1-C24 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; when containing substitution, the substitution is selected from deuterium, C1-C24 alkyl, C3-C24 cycloalkyl, C R2-R4 are each independently selected from hydrogen, deuterium, C1-C24 alkyl; R5-R6 are each independently selected from C1-C24 alkyl, C3-C24 cycloalkyl, substituted or unsubstituted C6-C30 aryl, or R5 and R6 form a saturated or unsaturated C3-C15 membered ring with the carbon atom to which they are commonly attached; R7 is selected from hydrogen, deuterium, C1-C24 alkyl substituted or unsubstituted C6-C30 aryl, C5-C30 nitrogen heteroaryl.

2. The boron nitrogen compound according to claim 1, characterized in that Ring A is selected from phenyl and naphthyl, and ring B is selected from phenyl, naphthyl, pyridyl, quinolyl or quinoxalinyl.

3. The boron nitrogen compound according to claim 1, characterized in that The R1 is monosubstituted, and R1 is selected from hydrogen, deuterium, C1-C12 alkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C2-C18 heteroaryl; when it contains substitution, the substitution is selected from one or more of deuterium, tert-butyl, adamantyl, and phenyl.

4. The boron nitrogen compound according to claim 1, characterized in that R2, R3, and R4 are each the same or different and are selected from deuterium, methyl, ethyl, propyl, and tert-butyl; R5-R6 are each the same or different and are selected from methyl, phenyl, and tert-butylphenyl, or R5 and R6 are connected to form a cyclopentyl, cyclohexyl, or fluorene ring; R7 is selected from hydrogen, deuterium, phenyl, tert-butylphenyl, and carbazole.

5. The boron nitrogen compound according to claim 1, characterized in that The boron nitrogen compound is selected from any one of the chemical structures shown below, wherein "D" represents deuterium: .

6. Use of the boron nitrogen compound according to any one of claims 1 to 5 in the preparation of electronic devices.

7. The use according to claim 6, characterized in that: The electronic device is an organic electroluminescent device, an organic integrated circuit, an organic field effect transistor, an organic photoelectric device, an organic thin film transistor, an organic light emitting transistor, an organic solar cell, an organic optical detector, an organic photoreceptor, an organic field quenching device, a light emitting electrochemical cell and / or an organic laser diode.

8. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises a cathode, an anode and an organic functional layer therebetween; the organic functional layer contains the boron nitrogen compound as claimed in any one of claims 1 to 5.

9. An organic optoelectronic device, characterized in that: The organic photoelectric device comprises a first electrode, a second electrode facing the first electrode, and a light-emitting material layer arranged between the first electrode and the second electrode; the light-emitting material layer contains the boron nitrogen compound as claimed in any one of claims 1 to 5.

10. A composition, characterized in that The composition comprises the boron nitrogen compound according to any one of claims 1 to 5.

11. A preparation, characterized in that The preparation comprises the boron nitrogen compound according to any one of claims 1 to 5 and at least one solvent.

12. A display or lighting device, characterized in that: The device comprises one or more of the organic electroluminescent device according to claim 8 and / or the organic photoelectric device according to claim 9.

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