A boron-containing resonant organic compound and an organic electroluminescent device comprising the same

Abstract

The present invention relates to a boron-containing resonant organic compound and an organic electroluminescent device comprising the same, belonging to the field of semiconductor technology. The structure of the compound provided by the present invention is shown in general formula (1): When the compound of the present invention is used as a doping material in the light-emitting layer material of an organic electroluminescent device, it can be used as a green light doping material for the light-emitting layer of an organic electroluminescent device, thereby improving the lifespan of the device.

Description

Technical Field

[0001] The present invention relates to the field of semiconductor technology, and particularly to a boron-containing resonant organic compound and an organic electroluminescent device comprising the same. Background Art

[0002] Compared with liquid crystal display (LCD), organic light-emitting diode (OLED) has technical advantages such as lighter and thinner, high color contrast, low power consumption, fast response, high definition, and flexibility, and is considered to dominate future display terminal products. With the advent of the 5G era, the new information display industry urgently needs iterative development. The early lower color gamut standards (BT.709 and DCIP3) can no longer meet the high-quality technical development requirements of display products. To achieve the performance requirements of ultra-high definition and higher picture quality for display products, the new generation of display standard (BT.2020) drives OLED luminescent materials to develop towards high color purity, which requires the core luminescent materials to have a narrower emission spectrum. Among the current commercial OLED red, green, and blue color display technologies, the blue light uses the triplet-triplet conversion (TTF) technology of traditional fluorescence. Although this technology has low efficiency, it has high color purity and basically meets the BT.2020 display index; the green and red lights use phosphorescent emission technology. This technology has high efficiency, and the red light is close to the BT.2020 display index. However, the green light is limited by the relatively wide emission spectrum of phosphorescence and has a large difference from the requirements of the high-definition display index. Therefore, it is very crucial to develop high-color-purity green OLED materials.

[0003] Since 2020, green light materials with a narrow full width at half maximum (FWHM < 30 nm) based on the boron-nitrogen resonance structure have been successively reported: DOI: 10.1002 / adom.201902142, DOI: 10.1002 / anie.202008264, DOI: 10.1021 / jacs.0c10081, DOI: 10.1038 / s41467-022-32607-3, DOI: 10.1002 / anie.202202380, etc., showing extremely high color purity and efficiency of this type of material and becoming the development trend of high-color-purity green OLEDs. However, there are still many technical difficulties in the development of green light ultra-high color purity materials containing boron-nitrogen structures, and the existing materials also have the defect that their efficiency and lifespan cannot meet the requirements of mass production. Developing narrow FWHM green light materials based on the boron-nitrogen resonance structure that can meet practical applications is a key technical point for the next generation of high-color-purity, high-color gamut coverage, high-efficiency, and high-immersion display devices.

[0004] In addition, the sensitization technology combines triplet exciton sensitizing materials (including but not limited to TADF materials and phosphorescent materials) with fluorescent doping materials. Using the triplet exciton sensitizing materials as the exciton sensitization medium, it makes full use of triplet excitons and transfers the energy to the fluorescent doping materials through energy transfer, which can also achieve a 100% internal quantum efficiency of the device. This technology can make up for the deficiency of the exciton utilization rate of fluorescent doping materials and effectively utilize the characteristics of high fluorescence quantum yield, high device stability, high color purity, and low cost of fluorescent doping materials, showing broad prospects in the application of OLEDs. The sensitization technology can simultaneously achieve efficiency comparable to that of phosphorescence and a relatively narrow full width at half maximum. Therefore, developing the sensitization technology based on boron-containing luminescent materials with a narrow full width at half maximum has unique advantages and strong potential for meeting the BT.2020 display standards. Summary of the Invention

[0005] In view of the above problems existing in the prior art, the present invention provides a boron-containing resonance organic compound and an organic electroluminescent device containing the same. The compound of the present invention is used as a green light doping material for the light-emitting layer of an organic electroluminescent device, which can significantly improve the lifespan of the device.

[0006] The technical solution of the present invention is as follows: A boron-containing resonance organic compound, the structure of the boron-containing resonance organic compound is shown in the general formula (1):

[0007]

[0008] In the general formula (1), R 1 ~R 19 each independently represents a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 ~C 10 alkyl group, a substituted or unsubstituted C 3 ~C 10 cycloalkyl group, a substituted or unsubstituted C 2 ~C 10 alkenyl group, a substituted or unsubstituted C 2 ~C 10 alkynyl group, a substituted or unsubstituted C 1 ~C 10 alkoxy group, a substituted or unsubstituted C 6 ~C 10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C 6 ~C 30 aryl group, a substituted or unsubstituted C 2 ~C 30 heteroaryl group, a substituted or unsubstituted C 2 ~C 30 boranyl group;

[0009] R 1 ~R 14 Any two adjacent groups among them can be connected to form a ring;

[0010] R 18 and R 19 can be connected to form a ring;

[0011] M 1 represents one of a substituted or unsubstituted C 6 -C 30 aromatic ring, a substituted or unsubstituted 5- to 30-membered heteroaromatic ring;

[0012] M 2 represents a six-membered ring substituted or unsubstituted by R;

[0013] The said R represents a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 ~C 10 alkyl group, a substituted or unsubstituted C 3 ~C 10 cycloalkyl group, a substituted or unsubstituted C 2 ~C 10 alkenyl group, a substituted or unsubstituted C 2 ~C 10 alkynyl group, a substituted or unsubstituted C 1 ~C 10 alkoxy group, a substituted or unsubstituted C 6 ~C 10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C 6 ~C 30 aryl group, a substituted or unsubstituted 5- to 30-membered heteroaryl group, a substituted or unsubstituted C 2 ~C 30 boranyl group;

[0014] The substitution mode of the said R is a single bond or a fused-ring connection;

[0015] When M 1 and M 2 both represent a substituted or unsubstituted benzene ring, R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 18 and R 19 do not simultaneously represent a hydrogen atom;

[0016] X represents a carbon atom or a silicon atom;

[0017] The substituents for replacing the above-mentioned replaceable groups are each independently selected from a deuterium atom, a tritium atom, a halogen atom, a cyano group, a C 1 -C 10 alkyl group, a deuterium- or tritium-substituted C 1 -C 10 alkyl group, a C 3 -C 10 cycloalkyl group, a C 6 -C 30 aryl group, a deuterium- or tritium-substituted C 6 -C 30 aryl group, a 5- to 30-membered heteroaryl group, a deuterium- or tritium-substituted C 2 -C 30 heteroaryl group, or one or more of the above;

[0018] The heteroatoms in the heteroaryl group and the heteroaromatic ring are each independently selected from one or more of O, S, N, Si, and B.

[0019] The present invention also provides an organic light-emitting device, which sequentially includes a substrate, a first electrode, a second electrode, and a functional layer, wherein the functional layer is located between the first electrode and the second electrode, and the functional layer contains the boron-containing resonance-type organic compound of the present invention.

[0020] The present invention also provides a material for an organic electroluminescent device, which contains the boron-containing resonance-type organic compound of the present invention.

[0021] The present invention also provides an application of the boron-containing resonance-type organic compound, which is applied to an organic electroluminescent device.

[0022] The present invention also provides a display element, which includes the organic electroluminescent device of the present invention.

[0023] The present invention also provides an illumination device, which includes the organic electroluminescent device of the present invention.

[0024] The present invention also provides an electronic device, which is equipped with the organic electroluminescent device of the present invention.

[0025] Compared with the prior art, the beneficial technical effects of the present invention are as follows:

[0026] (1) When the compound of the present invention is applied to an organic electroluminescent device, it can be used as a doping material for a light-emitting layer material, and can emit green fluorescence under the action of an electric field, and can be applied to the fields of organic electroluminescent lighting or organic electroluminescent display;

[0027] (2) When the compound of the present invention is used as a doping material and a phosphorus photosensitizer is introduced, the device lifetime can be effectively improved;

[0028] (3) The spectral FWHM of the compounds of the present invention is narrow, which can effectively improve the color gamut of the device;

[0029] The compounds of the present invention have the characteristic of narrow full width at half maximum and can be used as the green light doping material for the light-emitting layer of the organic electroluminescent device, thereby improving the lifespan of the device. Brief Description of the Drawings

[0030] Figure 1 It is a schematic structural diagram of the materials of the present invention applied to the OLED device;

[0031] Among them, 1 is the transparent substrate layer, 2 is the anode layer, 3 is the hole injection layer, 4 is the hole transport layer, 5 is the electron blocking layer, 6 is the light-emitting layer, 7 is the hole blocking layer, 8 is the electron transport layer, 9 is the electron injection layer, and 10 is the cathode layer;

[0032] Figure 2 It is the PL spectrogram of the compound 36 of the present invention in toluene solution (1×10 -5 M);

[0033] Figure 3 It is the PL spectrogram of the compound 48 of the present invention in toluene solution (1×10 -5 M);

[0034] Figure 4 It is the PL spectrogram of the compound 64 of the present invention in toluene solution (1×10 -5 M);

[0035] Figure 5 It is the PL spectrogram of the compound 533 of the present invention in toluene solution (1×10 -5 M);

[0036] Figure 6 It is the nuclear magnetic resonance hydrogen spectrum of the compound 36 of the present invention;

[0037] Figure 7 It is the nuclear magnetic resonance hydrogen spectrum of the compound 48 of the present invention;

[0038] Figure 8 It is the nuclear magnetic resonance hydrogen spectrum of the compound 64 of the present invention;

[0039] Figure 9 It is the nuclear magnetic resonance hydrogen spectrum of the compound 533 of the present invention. Detailed Embodiments

[0040] The present invention will be specifically described below in conjunction with the drawings and embodiments.

[0041] In the present invention, when describing electrodes, organic electroluminescent devices, and other structural bodies, terms indicating orientation such as "upper", "lower", "top", and "bottom" only represent the orientation in a specific state, and do not mean that the relevant structures can only exist in the stated orientation; on the contrary, if the structural body can change its position, for example, be inverted, the orientation of the structural body will change accordingly. Specifically, in the present invention, the "bottom" and "lower" sides of the electrode refer to the side of the electrode close to the substrate during the preparation process, and the opposite side away from the substrate is the "top" and "upper" sides.

[0042] In the present invention, the term "capable of forming a ring connection" or "can form a ring connection" means that two groups can be unconnected or can be connected to each other to form a ring, preferably through a C-C single bond, a C═C double bond, an O atom, an S atom, CQ 1 Q 2 、NQ 3 to form a ring, where Q 1 、Q 2 、Q 3 represents a substituted or unsubstituted C 1 -C 10 alkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, or a substituted or unsubstituted C 2 -C 30 heteroaryl group; preferably, it can form a substituted or unsubstituted 6-membered to 30-membered aromatic ring, a substituted or unsubstituted 5-membered to 30-membered heteroaromatic ring, or a substituted or unsubstituted 5-membered to 30-membered aliphatic ring.

[0043] In the present invention, the substituted or unsubstituted arylamino group described in the present invention means where Q 4 、Q 5 represent substituted or unsubstituted aromatic groups, and Q 4 、Q 5 preferably represent substituted or unsubstituted C 6 -C 30 aryl groups or substituted or unsubstituted C 2 -C 30 heteroaryl groups.

[0044] In the present invention, the substituted or unsubstituted C 6 -C 30An aryl group refers to a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted condensed tetraphenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted group, a substituted or unsubstituted meta-terphenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted indenyl group, a fused ring of a combination thereof or a combination of the aforementioned groups, but not limited thereto.

[0045] In the present invention, the substituted or unsubstituted C 2 -C 30 heteroaryl group, the substituted or unsubstituted C 5 -C 30 heteroaryl group, and the substituted or unsubstituted 5- to 30-membered heteroaryl group refer to a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzothiazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a fused ring of a combination thereof or a combination of the aforementioned groups, but not limited thereto.

[0046] The C 1 -C 10 alkyl group (including a straight-chain alkyl group and a branched-chain alkyl group) in the present invention refers to a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, an isobutyl group, a sec-butyl group, a neopentyl group, a n-pentyl group, an isopentyl group, an octyl group, a heptyl group, a n-decyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 3-methylpentyl group, a 1-butylpentyl group, etc., but not limited thereto.

[0047] The C 3 -C 10A cycloalkyl group refers to a monovalent monocyclic saturated hydrocarbon group including 3 to 10 carbon atoms as ring-forming atoms. In this text, C 4 -C 9 cycloalkyl groups are preferably used, more preferably C 5 -C 8 cycloalkyl groups, and particularly preferably C 5 -C 7 cycloalkyl groups. Non-limiting examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl, cycloheptyl, etc., but are not limited thereto.

[0048] The halogen atom in the present invention refers to a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

[0049] The C 1 -C 10 alkoxy group in the present invention refers to methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, isopropoxy, etc., but is not limited thereto.

[0050] The C 2 -C 10 alkenyl group in the present invention refers to vinyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylethenyl, styryl, 2,2-diphenylethenyl, 1,2-diphenylethenyl, 1,1-dimethylallyl, 1-methylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, etc., but is not limited thereto.

[0051] The C1-C10 alkynyl group in the present invention is preferably a C2-C8 alkynyl group, more preferably a C2-C5 alkynyl group, and non-limiting examples thereof may include ethynyl, propynyl, n-butynyl, isobutynyl, n-pentynyl, isopentynyl, neopentynyl, etc., but are not limited thereto.

[0052] The substituents for the substitution groups are optionally selected from one or more of a deuterium atom, a chlorine atom, a fluorine atom, a trifluoromethyl group, an adamantyl group, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-pentyl group, a tert-butyl group, a butyl group, a methoxy group, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a quinolinyl group, an isoquinolinyl group, a furyl group, a thienyl group, an indolyl group, a pyrrolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a 9,9-dimethylfluorenyl group, a spirofluorene group, a carbazolyl group, an N-phenylcarbazolyl group, a carbazolinyl group, an azaphenanthryl group.

[0053] The present invention provides a boron-containing resonance organic compound, and the structure of the boron-containing resonance organic compound is shown in the general formula (1):

[0054]

[0055] In general formula (1), R 1 ~R 19 each independently represents a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 ~C 10 alkyl group, a substituted or unsubstituted C 3 ~C 10 cycloalkyl group, a substituted or unsubstituted C 2 ~C 10 alkenyl group, a substituted or unsubstituted C 2 ~C 10 alkynyl group, a substituted or unsubstituted C 1 ~C 10 alkoxy group, a substituted or unsubstituted C 6 ~C 10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C 6 ~C 30 aryl group, a substituted or unsubstituted C 2 ~C 30 heteroaryl group, a substituted or unsubstituted C 2 ~C 30 boranyl group;

[0056] R 1 ~R 14 any two adjacent groups among them may be connected to form a ring;

[0057] R 18 and R 19 may be connected to form a ring;

[0058] M 1 represents a substituted or unsubstituted C 6 -C 30 aryl ring, a substituted or unsubstituted 5-30 membered heteroaryl ring;

[0059] M 2 represents a six-membered ring substituted or unsubstituted by R;

[0060] The said R represents a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 ~C 10 alkyl group, a substituted or unsubstituted C 3 ~C 10 cycloalkyl group, a substituted or unsubstituted C 2 ~C 10 alkenyl group, a substituted or unsubstituted C 2 ~C 10Alkynyl, substituted or unsubstituted C 1 ~C 10 Alkoxy, substituted or unsubstituted C 6 ~C 10 Aryloxy, substituted or unsubstituted arylamino, substituted or unsubstituted C 6 ~C 30 Aryl, substituted or unsubstituted 5 - 30 - membered heteroaryl, substituted or unsubstituted C 2 ~C 30 One of boranyl groups;

[0061] The substitution mode of the said R is single - bond or fused - ring connection;

[0062] When M 1 and M 2 both represent substituted or unsubstituted benzene rings, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 18 and R 19 do not all represent hydrogen atoms at the same time;

[0063] X represents a carbon atom or a silicon atom;

[0064] The substituents for substituting the above - mentioned substitutable groups are each independently selected from a deuterium atom, a tritium atom, a halogen atom, a cyano group, C 1 ~C 10 alkyl, deuterium - or tritium - substituted C 1 ~C 10 alkyl, C 3 ~C 10 cycloalkyl, C 6 ~C 30 aryl, deuterium - or tritium - substituted C 6 ~C 30 aryl, 5 - 30 - membered heteroaryl, deuterium - or tritium - substituted C 2 ~C 30 one or more of heteroaryl groups;

[0065] The heteroatoms in the said heteroaryl and heteroaromatic rings are each independently selected from one or more of O, S, N, Si, B.

[0066] In a preferred embodiment, in the general formula (1), R 1 -R 19 each occurrence, the same or different, represents a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, substituted or unsubstituted C 1 ~C 10alkyl, substituted or unsubstituted C 3 ~C 10 cycloalkyl, substituted or unsubstituted C 1 ~C 10 alkoxy, substituted or unsubstituted C 1 ~C 10 aryloxy, substituted or unsubstituted arylamino, substituted or unsubstituted C 6 ~C 30 aryl, substituted or unsubstituted C 2 ~C 30 heteroaryl;

[0067] R 1 -R 14 Any two adjacent ones of them can be connected to form a ring;

[0068] R 18 and R 19 can be connected to form a ring;

[0069] M 1 represents a substituted or unsubstituted C 6 ~C 30 aryl ring, or a substituted or unsubstituted 5- to 30-membered heteroaryl ring;

[0070] M 2 represents a substituted or unsubstituted six-membered ring;

[0071] When M 1 and M 2 both represent a substituted or unsubstituted benzene ring, R 1 -R 8 、R 18 and R 19 do not all represent hydrogen atoms;

[0072] X represents C, Si;

[0073] The substituents for the substituting groups are each independently selected from deuterium, tritium, a halogen atom, a cyano group, C 1 ~C 10 alkyl, deuterium- or tritium-substituted C 1 ~C 10 alkyl, C 6 ~C 30 aryl, deuterium- or tritium-substituted C 6 ~C 30 aryl, C 5 ~C 30 heteroaryl, deuterium- or tritium-substituted C 2 ~C 30 heteroaryl.

[0074] Preferred embodiment, the boron-containing resonant organic compound has a structure as shown in any one of General Formulas (1-1) to (1-3):

[0075]

[0076]

[0077] In General Formulas (1-1) to (1-3), R 1 -R 25 Each occurrence, which may be the same or different, represents a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 ~C 10 alkyl group, a substituted or unsubstituted C 3 ~C 10 cycloalkyl group, a substituted or unsubstituted C 1 ~C 10 alkoxy group, a substituted or unsubstituted C 1 ~C 10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C 6 ~C 30 aryl group, a substituted or unsubstituted C 2 ~C 30 heteroaryl group;

[0078] R 1 -R 25 Any two adjacent ones in R can be connected to form a ring;

[0079] Ar 3 Each occurrence, which may be the same or different, represents a substituted or unsubstituted C 1 ~C 10 alkyl group, a substituted or unsubstituted C 3 ~C 10 cycloalkyl group, a substituted or unsubstituted C 1 ~C 10 alkoxy group, a substituted or unsubstituted C 1 ~C 10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C 6 ~C 30 aryl group, a substituted or unsubstituted C 2 ~C 30 heteroaryl group;

[0080] X represents C or Si;

[0081] In General Formula (1-1), R 1 -R 8 、R 18 and R 19 do not simultaneously represent hydrogen atoms;

[0082] The substituents for the substituting groups are each independently selected from deuterium, tritium, a halogen atom, a cyano group, C 1 to C 10 alkyl, deuterium- or tritium-substituted C 1 to C 10 alkyl, C 6 to C 30 aryl, deuterium- or tritium-substituted C 6 to C 30 aryl, C 5 to C 30 heteroaryl, deuterium- or tritium-substituted C 2 to C 30 heteroaryl, and any one of them.

[0083] In a preferred embodiment, the boron-containing resonance-type organic compound has a structure represented by any one of general formulas (1-4) to (1-6):

[0084]

[0085]

[0086] In general formulas (1-4) to (1-6), the meanings of R 2 , R 7 , R 10 , R 13 , R 16 , R 18 , R 21 , and X are the same as defined in claim 2;

[0087] Ar 3 represents substituted or unsubstituted C 1 to C 10 alkyl, substituted or unsubstituted C 3 to C 10 cycloalkyl, substituted or unsubstituted C 1 to C 10 alkoxy, substituted or unsubstituted C 1 to C 10 aryloxy, substituted or unsubstituted arylamino, substituted or unsubstituted C 6 to C 30 aryl, substituted or unsubstituted C 2 to C 30 heteroaryl;

[0088] The substituents for the substituting groups are each independently selected from deuterium, tritium, a halogen atom, a cyano group, C 1 to C 10 alkyl, deuterium- or tritium-substituted C 1 to C 10 alkyl, C6 ~C 30 Aryl, deuterium- or tritium-substituted C 6 ~C 30 Aryl, C 5 ~C 30 Heteroaryl, deuterium- or tritium-substituted C 2 ~C 30 Any one of heteroaryls.

[0089] In a preferred embodiment, the structure of the boron-containing resonance-type organic compound is represented by any one of General Formulas (1-7) to (1-12):

[0090]

[0091] In General Formulas (1-7) to (1-12), each occurrence of R, which may be the same or different, represents a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 ~C 10 Alkyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, substituted or unsubstituted C 1 ~C 10 Alkoxy, substituted or unsubstituted C 1 ~C 10 Aryloxy, substituted or unsubstituted arylamino, substituted or unsubstituted C 6 ~C 30 Aryl, substituted or unsubstituted C 2 ~C 30 One of heteroaryls;

[0092] X represents C, Si;

[0093] The substituents for the substituent groups are each independently selected from deuterium, tritium, halogen atoms, cyano groups, C 1 ~C 10 Alkyl, deuterium- or tritium-substituted C 1 ~C 10 Alkyl, C 6 ~C 30 Aryl, deuterium- or tritium-substituted C 6 ~C 30 Aryl, C 5 ~C 30 Heteroaryl, deuterium- or tritium-substituted C 2 ~C 30 Any one of heteroaryls.

[0094] In a preferred embodiment, the R, R 1 -R 25Independently represented as one of a hydrogen atom, a deuterium atom, a tritium atom, a fluorine atom, a cyano group, an adamantyl group, a methyl group, a deuterated methyl group, a tritiated methyl group, a trifluoromethyl group, an ethyl group, a deuterated ethyl group, a tritiated ethyl group, an isopropyl group, a deuterated isopropyl group, a tritiated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a tritiated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a tritiated cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a deuterated phenyl group, a tritiated phenyl group, a biphenyl group, a deuterated biphenyl group, a tritiated biphenyl group, a terphenyl group, a deuterated terphenyl group, a tritiated terphenyl group, a diphenyl ether group, a methyl-substituted diphenyl ether group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a phenyl-substituted pyridyl group, a quinolinyl group, a furyl group, a thienyl group, a benzofuryl group, a dibenzofuryl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a spirofluorene group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group, an isopropyl-substituted phenyl group, a tert-butyl-substituted phenyl group, a methyl-substituted biphenyl group, an ethyl-substituted biphenyl group, an isopropyl-substituted biphenyl group, a tert-butyl-substituted biphenyl group, a deuterated methyl-substituted phenyl group, a deuterated ethyl-substituted phenyl group, a deuterated isopropyl-substituted phenyl group, a deuterated tert-butyl-substituted phenyl group, a deuterated methyl-substituted biphenyl group, a deuterated ethyl-substituted biphenyl group, a deuterated isopropyl-substituted biphenyl group, a deuterated tert-butyl-substituted biphenyl group, a tert-butyl-substituted dibenzofuryl group, a phenyl-substituted tert-butyl, an anthraquinonyl group, a phenyl-substituted triazinyl group, a phenyl-substituted boranyl group, a methoxy group, a tert-butoxy group;

[0095] The said Ar 3 Independently represented as one of a phenyl group, a deuterated phenyl group, a tritiated phenyl group, a biphenyl group, a deuterated biphenyl group, a tritiated biphenyl group, a terphenyl group, a deuterated terphenyl group, a tritiated terphenyl group, a diphenyl ether group, a methyl-substituted diphenyl ether group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a phenyl-substituted pyridyl group, a quinolinyl group, a furyl group, a thienyl group, a benzofuryl group, a dibenzofuryl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a spirofluorene group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group, an isopropyl-substituted phenyl group, a tert-butyl-substituted phenyl group, a methyl-substituted biphenyl group, an ethyl-substituted biphenyl group, an isopropyl-substituted biphenyl group, a tert-butyl-substituted biphenyl group, a deuterated methyl-substituted phenyl group, a deuterated ethyl-substituted phenyl group, a deuterated isopropyl-substituted phenyl group, a deuterated tert-butyl-substituted phenyl group, a deuterated methyl-substituted biphenyl group, a deuterated ethyl-substituted biphenyl group, a deuterated isopropyl-substituted biphenyl group, a deuterated tert-butyl-substituted biphenyl group, a phenyl-substituted amino group, a tert-butylbenzene-substituted amino group, a tert-butyl-substituted dibenzofuryl group, a phenyl-substituted tert-butyl, an anthraquinonyl group, a phenyl-substituted triazinyl group, a phenyl-substituted boranyl group, a methoxy group, a tert-butoxy group;

[0096] The said M 1represented by one of phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, diphenyl ether group, methyl-substituted diphenyl ether group, naphthyl, anthracenyl, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furyl, thienyl, benzofuryl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, phenyl-substituted amino, tert-butyl-substituted dibenzofuryl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, xanthenone group;

[0097] The M 2 represented by one of phenyl, deuterated phenyl, pyridyl, phenyl-substituted pyridyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl;

[0098] The substituents substituting the above-mentioned substituable groups are each independently selected from one or more of deuterium atom, chlorine atom, fluorine atom, trifluoromethyl, adamantyl, cyano group, methyl group, ethyl group, propyl group, isopropyl group, tert-pentyl group, tert-butyl group, butyl group, methoxy group, phenyl group, biphenyl group, naphthyl group, anthracenyl group, phenanthryl group, pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, benzoxazolyl group, benzothiazolyl group, quinoxalinyl group, quinolinyl group, isoquinolinyl group, furyl group, thienyl group, indolyl group, pyrrolyl group, dibenzofuryl group, dibenzothienyl group, 9,9-dimethylfluorenyl group, spirofluorene group, carbazolyl group, N-phenylcarbazolyl group, carbazolinyl group, azaphenanthryl group.

[0099] In a preferred embodiment, the R, R 1 -R 25 are each independently represented by the following structures:

[0100] hydrogen atom, cyano group,

[0101] any one of;

[0102] The Ar 3 is represented by any one of the following structures:

[0103]

[0104] any one of;

[0105] The M 1 is represented by any one of the following ring structures:

[0106]

[0107]

[0108] The said M 2 is represented as the following ring structure:

[0109]

[0110] The said Z is represented as C-R a ;

[0111] R a each occurrence is independently represented as a hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, adamantyl group, methyl group, deuterated methyl group, tritiated methyl group, trifluoromethyl group, ethyl group, deuterated ethyl group, tritiated ethyl group, isopropyl group, deuterated isopropyl group, tritiated isopropyl group, tert-butyl group, deuterated tert-butyl group, tritiated tert-butyl group, cyclopentyl group, deuterated cyclopentyl group, tritiated cyclopentyl group, methyl-substituted cyclopentyl group, cyclohexyl group, phenyl group, deuterated phenyl group, tritiated phenyl group, biphenyl group, deuterated biphenyl group, tritiated biphenyl group, terphenyl group, deuterated terphenyl group, tritiated terphenyl group, diphenyl ether group, methyl-substituted diphenyl ether group, naphthyl group, anthracenyl group, phenanthryl group, pyridyl group, phenyl-substituted pyridyl group, quinolinyl group, furyl group, thienyl group, benzofuryl group, dibenzofuryl group, dibenzothienyl group, carbazolyl group, N-phenylcarbazolyl group, 9,9-dimethylfluorenyl group, spirofluorene group, methyl-substituted phenyl group, ethyl-substituted phenyl group, isopropyl-substituted phenyl group, tert-butyl-substituted phenyl group, methyl-substituted biphenyl group, ethyl-substituted biphenyl group, isopropyl-substituted biphenyl group, tert-butyl-substituted biphenyl group, deuterated methyl-substituted phenyl group, deuterated ethyl-substituted phenyl group, deuterated isopropyl-substituted phenyl group, deuterated tert-butyl-substituted phenyl group, deuterated methyl-substituted biphenyl group, deuterated ethyl-substituted biphenyl group, deuterated isopropyl-substituted biphenyl group, deuterated tert-butyl-substituted biphenyl group, phenyl-substituted amino group, tert-butylbenzene-substituted amino group, tert-butyl-substituted dibenzofuryl group, phenyl-substituted tert-butyl group, xanthenone group, phenyl-substituted triazine group, phenyl-substituted boranyl group, methoxy group, tert-butoxy group.

[0112] In a preferred embodiment, the boron-containing resonance-type organic compound has a structure as shown in general formula (A-1):

[0113]

[0114] In general formula (A-1), R 1 ~R 19 each occurrence is independently represented as a hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C 1 ~C 10 alkyl group, substituted or unsubstituted C 3 ~C 10Cycloalkyl, substituted or unsubstituted C 2 ~C 10 Alkenyl, substituted or unsubstituted C 2 ~C 10 Alkynyl, substituted or unsubstituted C 1 ~C 10 Alkoxy, substituted or unsubstituted arylamino, substituted or unsubstituted C 6 ~C 30 Aryl, substituted or unsubstituted 5 - 30 - membered heteroaryl, substituted or unsubstituted C 2 ~C 30 One of boranyl groups;

[0115] R 1 ~R 19 Any two adjacent groups among them can be connected to form a ring;

[0116] M 1 Represents one of a substituted or unsubstituted C 6 -C 30 Aromatic ring, a substituted or unsubstituted 5 - 30 - membered heteroaromatic ring;

[0117] M 2 Represents a six - membered ring substituted or unsubstituted by R;

[0118] The said R represents a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 ~C 10 Alkyl, a substituted or unsubstituted C 3 ~C 10 Cycloalkyl, a substituted or unsubstituted C 2 ~C 10 Alkenyl, a substituted or unsubstituted C 2 ~C 10 Alkynyl, a substituted or unsubstituted C 1 ~C 10 Alkoxy, a substituted or unsubstituted arylamino, a substituted or unsubstituted C 6 ~C 30 Aryl, a substituted or unsubstituted 5 - 30 - membered heteroaryl, a substituted or unsubstituted C 2 ~C 30 One of boranyl groups;

[0119] The substitution mode of the said R is single - bond or fused - ring connection;

[0120] When M 1 and M 2 both represent substituted or unsubstituted benzene rings, R 1 、R 2 、R 3 、R 4 、R5 , R 6 , R 7 , R 8 , R 18 and R 19 are not simultaneously represented as hydrogen atoms;

[0121] The substituents used to replace the above-mentioned substituable groups are each independently selected from a deuterium atom, a halogen atom, a cyano group, C 1 ~C 10 alkyl, C 3 ~C 10 cycloalkyl, C 6 ~C 30 aryl, a 5- to 30-membered heteroaryl, or one or more of the foregoing;

[0122] The heteroatoms in the heteroaryl and heteroaromatic rings are each independently selected from one or more of O, S, N, Si, and B.

[0123] In a preferred embodiment, the boron-containing resonance organic compound has a structure represented by the general formula (A-2):

[0124]

[0125] In the general formula (A-2), R 1 ~R 23 are each independently represented as a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 ~C 10 alkyl, a substituted or unsubstituted C 3 ~C 10 cycloalkyl, a substituted or unsubstituted C 2 ~C 10 alkenyl, a substituted or unsubstituted C 2 ~C 10 alkynyl, a substituted or unsubstituted C 1 ~C 10 alkoxy, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C 6 ~C 30 aryl, a substituted or unsubstituted 5- to 30-membered heteroaryl, a substituted or unsubstituted C 2 ~C 30 boranyl, respectively;

[0126] R 1 ~R 23 any two adjacent groups among them may be connected to form a ring;

[0127] R 1 , R 2 , R 3 , R 4 , R 5 , R6 , R 7 , R 8 , R 18 and R 19 are not simultaneously represented as hydrogen atoms;

[0128] The substituents used to replace the above-mentioned substituable groups are each independently selected from one or more of a deuterium atom, a halogen atom, a cyano group, a C 1 ~C 10 alkyl group, a C 3 ~C 10 cycloalkyl group, a C 6 ~C 30 aryl group, a 5-30-membered heteroaryl group;

[0129] The heteroatoms in the heteroaryl group are each independently selected from one or more of O, S, N, Si, and B.

[0130] In a preferred embodiment, the boron-containing resonance organic compound has a structure represented by the general formula (A-3):

[0131]

[0132] In the general formula (A-3), the R 2 , R 7 , R 10 , R 13 , R 16 , R 21 each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 ~C 10 alkyl group, a substituted or unsubstituted C 3 ~C 10 cycloalkyl group, a substituted or unsubstituted C 2 ~C 10 alkenyl group, a substituted or unsubstituted C 2 ~C 10 alkynyl group, a substituted or unsubstituted C 1 ~C 10 alkoxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C 6 ~C 30 aryl group, a substituted or unsubstituted 5-30-membered heteroaryl group, a substituted or unsubstituted C 2 ~C 30 boranyl group;

[0133] The R 18 represents a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 ~C 10 alkyl group, a substituted or unsubstituted C 3 ~C 10Cycloalkyl, substituted or unsubstituted C 2 ~C 10 alkenyl, substituted or unsubstituted C 2 ~C 10 alkynyl, substituted or unsubstituted C 1 ~C 10 alkoxy, substituted or unsubstituted arylamino, substituted or unsubstituted C 6 ~C 30 aryl, substituted or unsubstituted 5 - 30 - membered heteroaryl, substituted or unsubstituted C 2 ~C 30 boranyl;

[0134] The substituents for substituting the above - mentioned substituable groups are each independently selected from a deuterium atom, a halogen atom, a cyano group, a C 1 ~C 10 alkyl, a C 3 ~C 10 cycloalkyl, a C 6 ~C 30 aryl, one or more of 5 - 30 - membered heteroaryl;

[0135] The heteroatoms in the heteroaryl are each independently selected from one or more of O, S, N, Si, B.

[0136] In a preferred embodiment, the M 1 is represented by a substituted or unsubstituted group as follows: phenyl, naphthyl, anthracenyl, phenanthryl, pyridyl, quinolinyl, furyl, thienyl, benzofuryl, benzothienyl, dibenzofuryl, dibenzothienyl, N - phenylcarbazolyl, 9,9 - dimethylfluorenyl, indolo[3,2,1 - jk]carbazolyl, 1,1,4,4 - tetramethyl - 1,2,3,4 - tetrahydronaphthyl, spirofluorene, any one of them;

[0137] The M 2 is represented by an R - substituted or unsubstituted group as follows: phenyl, naphthyl, anthracenyl, phenanthryl, pyridyl, quinolinyl, any one of them;

[0138] R represents a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorene group, a substituted or unsubstituted amino group, a substituted or unsubstituted triazine group;

[0139] The said R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23Are each independently represented by a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorene group, a substituted or unsubstituted amino group, a substituted or unsubstituted triazinyl group;

[0140] The substituents for the substituted groups are each independently selected from a deuterium atom, a chlorine atom, a fluorine atom, a trifluoromethyl group, an adamantyl group, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-pentyl group, a tert-butyl group, a butyl group, a methoxy group, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a quinolinyl group, an isoquinolinyl group, a furyl group, a thienyl group, an indolyl group, a pyrrolyl group, a dibenzofuryl group, a dibenzothienyl group, a 9,9-dimethylfluorenyl group, a spirofluorene group, a carbazolyl group, an N-phenylcarbazolyl group, a carbazolinyl group, an aza-phenanthryl group, or a combination of one or more thereof.

[0141] In a preferred embodiment, the M 1 Is represented by the following structure:

[0142]

[0143] Any one of;

[0144] The M 2 Is represented by the following structure:

[0145] Any one of;

[0146] The Z is represented by C-(H) or C-(R);

[0147] The R, R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 are each independently represented by the following structures:

[0148] a hydrogen atom, a deuterium atom, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a cyano group, a trifluoromethyl group,

[0149] any one of.

[0150] In a preferred embodiment, the M 1 is represented by the following structure:

[0151] any one of;

[0152] the M 2 is represented by the following structure:

[0153] any one of;

[0154] The Z is represented by C-(H) or C-(R);

[0155] The R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 20 , R 21 , R 22 , R 23Are each independently represented as the following structures:

[0156] A hydrogen atom, a deuterium atom, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, Any one of;

[0157] Said R 18 and R 19 Are each independently represented as the following structures:

[0158] A hydrogen atom, a cyano group, a tert-butyl group Any one of;

[0159] Said Ar 3 Is represented as the following structure: Any one of.

[0160] In a preferred embodiment, the specific structural formula of the boron-containing resonance organic compound is any one of the following structures:

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187] The present invention also provides an organic light-emitting device, which sequentially includes a substrate, a first electrode, a second electrode, and a functional layer. The functional layer is located between the first electrode and the second electrode, and the functional layer contains the boron-containing resonance organic compound.

[0188] In a preferred embodiment, the functional layer includes a light-emitting layer, the light-emitting layer includes a host material and a doping material, and the doping material is the boron-containing resonance organic compound.

[0189] In a preferred embodiment, the functional layer includes a light-emitting layer, the light-emitting layer includes a first host material, a second host material, and a doping material. At least one of the first host material and the second host material is a TADF material, and the doping material is the boron-containing resonance organic compound.

[0190] In a preferred embodiment, the functional layer includes a light-emitting layer, the light-emitting layer includes a host material, an exciton sensitizing material, and a doping material. The exciton sensitizing material is a metal element-containing complex, and the doping material is the boron-containing resonance organic compound.

[0191] The present invention also provides a material for an organic electroluminescent device, which contains the boron-containing resonance organic compound described above in the present invention.

[0192] The present invention also provides an application of the boron-containing resonance organic compound, which is applied to an organic electroluminescent device.

[0193] In a preferred embodiment, the organic light-emitting functional layer includes a light-emitting layer, and the application of the boron-containing resonance organic compound of the present invention is to the light-emitting layer.

[0194] The present invention also provides a display element, which includes the organic electroluminescent device of the present invention.

[0195] The present invention also provides an illumination device, which includes the organic electroluminescent device of the present invention.

[0196] The present invention also provides an electronic device, which is equipped with the organic electroluminescent device of the present invention.

[0197] The organic electroluminescent device of the present invention can be a bottom-emitting organic electroluminescent device, a top-emitting organic electroluminescent device, or a stacked organic electroluminescent device, and no specific limitation is imposed thereon.

[0198] The organic electroluminescent device of the present invention includes a substrate, a first electrode, an organic light-emitting functional layer, and a second electrode. Among them, the organic light-emitting functional layer includes a hole transport region, a light-emitting layer, and an electron transport region. The hole transport region includes a hole injection layer, a hole transport layer, and an electron blocking layer. The electron transport region includes a hole blocking layer, an electron transport layer, and an electron injection layer. In addition, a CPL layer can be provided on the second electrode.

[0199] As the substrate of the organic electroluminescent device of the present invention, any substrate commonly used in organic electroluminescent devices can be used. Examples are transparent substrates such as glass or transparent PI film substrates; opaque substrates such as silicon substrates. Different substrates have different mechanical strengths, thermal stabilities, transparencies, surface smoothnesses, and water resistances. Depending on the properties of the substrate, its usage directions are different. In the present invention, a transparent PI film substrate is preferably used. The thickness of the substrate is not particularly limited.

[0200] A first electrode is formed on a substrate, and the first electrode and the second electrode can be opposite to each other. The first electrode can be an anode. The first electrode can be a transmissive electrode, a semi-transmissive electrode or a reflective electrode. When the first electrode is a transmissive electrode, it can be formed using a transparent metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO) or indium tin zinc oxide (ITZO), etc. When the first electrode is a semi-transmissive electrode or a reflective electrode, it can include metals such as Ag, Mg, Al, Pt, Pd, Au, Ni, Nd, Ir or Cr, and can also be an alloy of several metals, or a combination of a metal, a metal oxide and a metal alloy. The thickness of the first electrode layer depends on the material used, usually being 50 - 500 nm, preferably 70 - 300 nm and more preferably 100 - 200 nm.

[0201] The organic functional material layer disposed between the first electrode and the second electrode sequentially includes a hole transport region, a light-emitting layer and an electron transport region from bottom to top.

[0202] In the present invention, examples of the hole transport region constituting the organic electroluminescent device can include a hole injection layer, a hole transport layer, an electron blocking layer, etc.

[0203] As the materials for the hole injection layer, the hole transport layer and the electron blocking layer, any material can be selected from the known related materials for organic electroluminescent devices for use.

[0204] The hole injection layer contains a host organic material that can conduct holes, and also contains a P-type doping material with a deep HOMO energy level (the corresponding LUMO energy level will also be deep). Based on empirical summary, in order to achieve smooth injection of holes from the anode to the organic film layer, the HOMO energy level of the host organic material that conducts holes used in the anode interface buffer layer must have certain characteristics with the P-doping material, so as to expect the occurrence of a charge transfer state between the host material and the doping material, achieve Ohmic contact between the buffer layer and the anode, and achieve efficient injection from the electrode to hole injection and conduction.

[0205] In view of the above empirical summary, therefore, for hole-type host organic materials with different HOMO energy levels, different P-doping materials need to be selected to match them in order to achieve Ohmic contact at the interface and improve the hole injection effect.

[0206] In one embodiment of the present invention, the hole injection layer comprises a P-type doping material having charge conductivity selected from the following: quinone derivatives such as tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ); or hexaazatriphenylene derivatives such as 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CN); or cyclopropane derivatives such as 4,4',4”-((1E,1'E,1”E)-cyclopropane-1,2,3-trimethylenetris(cyanomethylene))tris(2,3,5,6-tetrafluorobenzyl); or metal oxides such as tungsten oxide and molybdenum oxide, but not limited thereto.

[0207] In the hole injection layer of the present invention, the ratio of the hole transport material to the P-type doping material used is 99:1 - 95:5, preferably 99:1 - 97:3, by mass.

[0208] The thickness of the hole injection layer of the present invention can be 5 - 100 nm, preferably 5 - 50 nm, and more preferably 5 - 20 nm, but the thickness is not limited to this range.

[0209] Preferably, as the hole transport layer material of the present invention, any compound disclosed in the following prior arts can be selected:

[0210]

[0211] Preferably, the hole transport layer material of the present invention and the host organic material in the hole injection layer are selected from the same compound.

[0212] The thickness of the hole transport layer of the present invention can be 5 - 200 nm, preferably 10 - 150 nm, and more preferably 20 - 100 nm, but the thickness is not limited to this range.

[0213] In one embodiment of the present invention, as the electron blocking layer material of the present invention, any compound disclosed in the following prior arts can be selected:

[0214]

[0215] The thickness of the electron blocking layer of the present invention can be 1 - 50 nm, preferably 5 - 40 nm, but the thickness is not limited to this range.

[0216] After forming the hole injection layer, the hole transport layer and the electron blocking layer, a corresponding light-emitting layer is formed on the electron blocking layer.

[0217] The light-emitting layer may comprise a host material and a dopant material. The host material may be a common green host material in the art, and the dopant material is a boron-containing resonance-type organic compound represented by the general formula (1) of the present invention.

[0218] The light-emitting layer may comprise a single host material or a dual host material;

[0219] The dual host material comprises a first host material and a second host material. At least one of the first host material and the second host material is preferably a TADF material;

[0220] TADF material refers to a material with thermally activated delayed fluorescence properties, characterized by having a small energy level difference between the first singlet excited state and the first triplet excited state. Therefore, singlet excitons and triplet excitons generated can be utilized simultaneously in the device, enabling the utilization rate of excitons generated electrochemically inside the device to approach 100% as much as possible. Compared with traditional fluorescent materials, TADF materials have a higher exciton utilization rate.

[0221] The light-emitting layer may comprise a host material, an exciton sensitizing material, and a dopant material;

[0222] The exciton sensitizing material refers to a material that can enable the luminescent material in the light-emitting layer to fully utilize electrochemically generated excitons, so that the light-emitting layer finally generates the emission spectrum of the sensitized material. The exciton sensitizer may undertake functions such as exciton capture, exciton conversion, and exciton transfer in the electroluminescent device. The boron-containing resonance-type organic compound represented by the general formula (1) of the present invention and the exciton sensitizing material are used in combination, which has an obvious improvement effect on problems such as device efficiency improvement, exciton annihilation in the device, and efficiency reduction.

[0223] In the light-emitting layer of the present invention, the ratio of the host material to the dopant material used is 99:1 - 70:30, preferably 99:1 - 85:15, and more preferably 97:3 - 87:13, based on mass.

[0224] The thickness of the light-emitting layer can be adjusted to optimize the luminous efficiency and driving voltage. The preferred thickness range is 5 nm to 50 nm, further preferably 10 - 50 nm, and more preferably 15 - 40 nm, but the thickness is not limited to this range.

[0225] In the present invention, the electron transport region may sequentially include, from bottom to top, a hole blocking layer, an electron transport layer, and an electron injection layer disposed above the light-emitting layer, but is not limited thereto.

[0226] The hole blocking layer is a layer that blocks holes injected from the anode from passing through the light-emitting layer and entering the cathode, thereby prolonging the lifespan of the device and improving the performance of the device. The hole blocking layer of the present invention may be disposed above the light-emitting layer. As the hole blocking layer material of the organic electroluminescent device of the present invention, compounds known in the prior art having a hole blocking effect can be used, for example:

[0227]

[0228] The thickness of the hole blocking layer of the present invention can be 2 - 200 nm, preferably 5 - 150 nm, more preferably 5 - 50 nm, but the thickness is not limited to this range.

[0229] The electron transport layer can be disposed above the light emitting layer or (if present) the hole blocking layer. The electron transport layer material is a material that can easily receive electrons from the cathode and transfer the received electrons to the light emitting layer. A material with high electron mobility is preferred. As the electron transport layer of the organic electroluminescent device of the present invention, the electron transport layer materials disclosed in the prior art for organic electroluminescent devices can be used, for example:

[0230]

[0231] In a preferred embodiment of the present invention, the electron transport layer further includes other compounds conventionally used in the electron transport layer, such as, Alq3, LiQ, preferably LiQ.

[0232] The thickness of the electron transport layer of the present invention can be 10 - 80 nm, preferably 20 - 60 nm and more preferably 25 - 45 nm, but the thickness is not limited to this range.

[0233] The electron injection layer can be disposed above the electron transport layer. The electron injection layer material is usually a material preferably having a low work function, so that electrons can be easily injected into the organic functional material layer. As the electron injection layer material of the organic electroluminescent device of the present invention, the electron injection layer materials disclosed in the prior art for organic electroluminescent devices can be used, for example: LiF, Cs 2 CO 3 、CsF, Csq, NaF, MgF 2 、CaF 2 、Al 2 O 3 、Yb, etc.

[0234] The thickness of the electron injection layer of the present invention can be 0.1 - 5 nm, preferably 0.5 - 3 nm and more preferably 0.8 - 1.5 nm, but the thickness is not limited to this range.

[0235] The second electrode can be disposed above the electron transport region. The second electrode can be a cathode. The second electrode can be a transmissive electrode, a semi-transmissive electrode or a reflective electrode. When the second electrode is a transmissive electrode, the second electrode can include, for example, Li, Yb, Ca, LiF / Ca, LiF / Al, Al, Mg, BaF 2, Ba, Ag, or their compounds or mixtures; when the second electrode is a semi-transmissive electrode or a reflective electrode, the second electrode may include Ag, Mg, Yb, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, or their compounds or mixtures, but not limited thereto. The thickness of the cathode depends on the materials used.

[0236] The organic electroluminescent device of the present invention may further include a packaging structure. The packaging structure may be a protective structure for preventing external substances such as moisture and oxygen from entering the organic layer of the organic electroluminescent device. The packaging structure may be, for example, a can, such as a glass can or a metal can; or a thin film covering the entire surface of the organic layer.

[0237] A method for preparing the organic electroluminescent device of the present invention includes successively laminating an anode, a hole injection layer, a hole transport layer, an electron blocking layer, an organic film layer, an electron transport layer, an electron injection layer, and a cathode on a substrate, and optionally a covering layer. In this regard, methods such as vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing, or LITI may be used, but not limited thereto. In the present invention, vacuum evaporation is preferably used to form each layer. Those skilled in the art can conventionally select each process condition in the vacuum evaporation method according to actual needs.

[0238] Preparation of Compounds

[0239] Synthesis of Compound 5 in Example 1:

[0240]

[0241]

[0242] Synthesis of Intermediate M1:

[0243] Raw material A1 (11 mmol, 2.99 g) and raw material B1 (10 mmol, 2.04 g) were added to a three-necked flask, dissolved in a mixed solvent (70 mL of toluene, 35 mL of ethanol), and then Pd(PPh 3 ) 4 (0.10 mmol, 0.12 g), 15 mL of 3 mol / L K 2 CO 3 aqueous solution was added. The reaction was heated under reflux for 12 hours under nitrogen protection. Samples were taken for TLC to confirm the completion of the reaction. After cooling to room temperature, the reaction mixture was filtered through a diatomaceous earth pad, rinsed with chloroform, and the resulting filtrate was evaporated in vacuo. The obtained residue was purified by column chromatography on silica gel using hexane / toluene as the eluent to obtain Intermediate M1.

[0244] Synthesis of Intermediate N1:

[0245] Add intermediate M1 (18.4 mmol, 4.95 g), cesium carbonate (55.2 mmol, 18.0 g) into a three-necked flask. Under nitrogen protection, add 120 mL of anhydrous DMF, stir at room temperature for 30 minutes. Under nitrogen protection, add raw material C1 (40.5 mmol, 11.32 g). The solution is refluxed for 24 hours under magnetic stirring, cooled, filtered, washed with water, dried, and purified by column chromatography to obtain intermediate N1.

[0246] Synthesis of intermediate J1:

[0247] Dissolve intermediate N1 (5.1 mmol, 4.02 g) in 50 mL of tetrahydrofuran (THF) solution. Under the condition of nitrogen passing at -78 °C, slowly add 2.3 mL of a 2.5 M n-butyllithium hexane solution; after stirring at -78 °C for 2 hours, slowly add 15 mL of a THF solution of raw material D1 (5.5 mmol, 1.0 g). Then slowly heat the reaction mixture to room temperature and stir overnight. Add 20 mL of dilute hydrochloric acid (1 M) solution, distilled water and ethyl acetate to the reaction mixture, separate the aqueous layer, and extract three times with ethyl acetate. The combined organic layers are dried over sodium sulfate and filtered. After removing the solvent under reduced pressure, dissolve the crude product in anhydrous dichloromethane, and then slowly add 47% boron trifluoride-diethyl ether. The reaction mixture is stirred overnight and quenched slowly with an aqueous NaHCO 3 aqueous solution. Then separate the aqueous layer and extract with dichloromethane. Dry over sodium sulfate, filter, and evaporate by rotary evaporation, and purify by column chromatography to obtain intermediate J1.

[0248] Synthesis of intermediate K1:

[0249] Add intermediate J1 (20.0 mmol, 17.42 g) into a three-necked flask in sequence, add 200 mL of glacial acetic acid, and use nitrogen protection. Cool to 0 °C with a low-temperature bath and strictly avoid light. Add NBS (25 mmol, 4.45 g) in batches and stir at 0 °C for 11 hours. Concentrate the reaction solution and purify it by silica gel column to obtain intermediate K1.

[0250] Synthesis of compound 5:

[0251] In a sealed pressure-resistant tube, under nitrogen protection, intermediate K1 (10 mmol, 9.50 g) and 90 mL of o-dichlorobenzene were added. A 2.5 M solution of n-butyllithium in n-hexane (30 mmol, 12 mL) was added at -78 °C, the system was heated to 60 °C and reacted for 2 hours, then boron tribromide (15 mmol, 1.5 mL) was added at 0 °C, and the reaction was continued at room temperature for 5 hours. Then, N,N-diisopropylethylamine (20 mmol, 3.5 mL) was added to the system at 0 °C, and the mixture was heated to 200 °C and reacted for 12 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain compound 5. In a toluene solution (1×10 -5 M), the half-peak width is 26 nm.

[0252] Example 2 Synthesis of Compound 36:

[0253]

[0254] Synthesis of Intermediate M2:

[0255] Raw material A1 (11 mmol, 2.99 g) and raw material B2 (10 mmol, 3.16 g) were added to a three-necked flask, dissolved in a mixed solvent (70 mL of toluene, 35 mL of ethanol), then Pd(PPh 3 ) 4 (0.10 mmol, 0.12 g) and 15 mL of 3 mol / L aqueous K 2 CO 3 solution were added. The mixture was heated under reflux for 14 hours under nitrogen protection. Samples were taken for TLC to confirm the completion of the reaction. After cooling to room temperature, the reaction mixture was filtered through a diatomaceous earth pad, rinsed with chloroform, and the resulting filtrate was evaporated in vacuo. The obtained residue was purified by column chromatography on silica gel using hexane / toluene as the eluent to obtain intermediate M2.

[0256] Synthesis of Intermediate N2:

[0257] Intermediate M2 (18.4 mmol, 7.02 g) and cesium carbonate (55.2 mmol, 18.0 g) were added to a two-necked flask. 120 mL of anhydrous DMF was added under nitrogen protection, and the mixture was stirred at room temperature for 35 minutes. Then, raw material C1 (40.5 mmol, 11.32 g) was added under nitrogen protection. The solution was refluxed with magnetic stirring for 20 hours, cooled, filtered, washed with water, dried, and purified by column chromatography to obtain intermediate N2.

[0258] Synthesis of Intermediate J2:

[0259] Dissolve the intermediate N2 (5.1 mmol, 4.59 g) in 50 mL of tetrahydrofuran (THF) solution. Under the condition of nitrogen passing at -78 °C, slowly add 2.3 mL of a n-butyllithium (2.5 M, 5.7 mmol) hexane solution. After stirring at -78 °C for 3 hours, slowly add 15 mL of a THF solution of the raw material D1 (5.5 mmol, 1.0 g). Then slowly heat the reaction mixture to room temperature and stir overnight. Add 20 mL of dilute hydrochloric acid (1 M) solution, distilled water and ethyl acetate to the reaction mixture, separate the aqueous layer, and extract it three times with ethyl acetate. The combined organic layers are dried over sodium sulfate and filtered. After removing the solvent under reduced pressure, dissolve the crude product in anhydrous dichloromethane, and then slowly add 47% boron trifluoride-diethyl ether. Stir the reaction mixture overnight and quench it slowly with an aqueous NaHCO 3 aqueous solution. Then separate the aqueous layer and extract it with dichloromethane. Dry it over sodium sulfate, filter, and evaporate by rotary evaporation, and purify it by column chromatography to obtain the intermediate J2.

[0260] Synthesis of intermediate K2:

[0261] Add the intermediate J2 (20.0 mmol, 19.67 g) to a three-necked flask in sequence, add 200 mL of glacial acetic acid, and protect it with nitrogen. Cool it to 0 °C using a low-temperature bath and strictly avoid light. Add NBS (25 mmol, 4.45 g) in batches and stir at 0 °C for 12 hours. Concentrate the reaction solution and purify it by silica gel column to obtain the intermediate K2.

[0262] Synthesis of compound 36:

[0263] In a sealed pressure-resistant tube, under nitrogen protection, add the intermediate K2 (10 mmol, 10.6 g) and 90 mL of o-dichlorobenzene. Add a n-butyllithium (2.5 M) hexane solution (30 mmol, 12 mL) at -78 °C, heat the system to 60 °C and react for 3 hours. Then add boron tribromide (15 mmol, 1.5 mL) at 0 °C, transfer it to room temperature and continue to react for 6 hours. Then add N,N-diisopropylethylamine (20 mmol, 3.5 mL) to the system at 0 °C, heat it to 200 °C and react for 11 hours. After the reaction, reduce the pressure and concentrate the organic layer, and then purify it by silica gel column chromatography to obtain compound 36. The half-peak width in toluene solution (1×10 -5 M) is 28 nm.

[0264] Synthesis of compound 119 in Example 3:

[0265]

[0266] Synthesis of intermediate M3:

[0267] Add raw material A1 (11 mmol, 2.99 g) and raw material B3 (10 mmol, 3.3 g) into a three-necked flask, dissolve them with a mixed solvent (70 mL of toluene, 35 mL of ethanol), then add Pd(PPh 3 ) 4 (0.10 mmol, 0.12 g), 15 mL of 3 mol / L K 2 CO 3 aqueous solution, and heat under reflux for 12 hours under nitrogen protection. Take samples for thin-layer chromatography to confirm the completion of the reaction. After cooling to room temperature, filter the reaction mixture through a diatomaceous earth pad, rinse with chloroform, and evaporate the obtained filtrate under vacuum. Purify the obtained residue by column chromatography on silica gel using hexane / toluene as the eluent to obtain intermediate M3.

[0268] Synthesis of intermediate N3:

[0269] Add intermediate M3 (18.4 mmol, 7.27 g) and cesium carbonate (55.2 mmol, 18.0 g) into a two-necked flask, add 120 mL of anhydrous DMF under nitrogen protection, stir at room temperature for 35 minutes, add raw material C1 (40.5 mmol, 11.32 g) under nitrogen protection, reflux the solution with magnetic stirring for 23 hours, cool, filter, wash with water, dry, and column chromatograph to obtain intermediate N3.

[0270] Synthesis of intermediate J3:

[0271] Dissolve intermediate N3 (5.1 mmol, 4.66 g) in 60 mL of tetrahydrofuran (THF) solution. Under the condition of nitrogen passing at -78 °C, slowly add 2.3 mL of a 2.5 M n-butyllithium hexane solution; after stirring at -78 °C for 2.5 hours, slowly add 15 mL of a THF solution of raw material D1 (5.5 mmol, 1.0 g). Then slowly heat the reaction mixture to room temperature and stir overnight. Add 20 mL of 1 M hydrochloric acid solution, distilled water, and ethyl acetate to the reaction mixture, separate the aqueous layer, and extract it three times with ethyl acetate. Dry the combined organic layers with sodium sulfate and filter. After removing the solvent under reduced pressure, dissolve the crude product in anhydrous dichloromethane, and then slowly add 47% boron trifluoride-diethyl ether. Stir the reaction mixture overnight and slowly quench it with a NaHCO 3 aqueous solution. Then separate the aqueous layer and extract it with dichloromethane. Dry it with sodium sulfate, filter, and evaporate by rotary evaporation, and column chromatograph to obtain intermediate J3.

[0272] Synthesis of intermediate K3:

[0273] Add intermediate J3 (20.0 mmol, 19.95 g) to a three-necked flask in sequence, add 220 mL of glacial acetic acid, protect with nitrogen, cool to 0 °C using a low-temperature bath and strictly avoid light, add NBS (25 mmol, 4.45 g) in batches, and stir at 0 °C for 12 hours. Concentrate the reaction solution and purify it through a silica gel column to obtain intermediate K3.

[0274] Synthesis of compound 119:

[0275] In a sealed pressure-resistant tube, under nitrogen protection, add intermediate K3 (10 mmol, 10.76 g) and 120 mL of o-dichlorobenzene. Add a 2.5 M solution of n-butyllithium in n-hexane (30 mmol, 12 mL) at -78 °C, heat the system to 60 °C and react for 3 hours. Then add boron tribromide (15 mmol, 1.5 mL) at 0 °C, transfer to room temperature and continue to react for 6 hours. Then add N,N-diisopropylethylamine (20 mmol, 3.5 mL) to the system at 0 °C, heat to 200 °C and react for 13 hours. After the reaction is completed, reduce the pressure and concentrate the organic layer, and then purify it by silica gel column chromatography to obtain compound 119. The half-peak width in toluene solution (1×10 -5 M) is 27 nm.

[0276] Synthesis of compound 149 in Example 4:

[0277]

[0278]

[0279] Synthesis of intermediate Y1:

[0280] Add raw material E1 (2.50 mmol, 0.85 g), B 2 pin 2 (2.75 mmol, 0.70 g), PdCl 2 (dppf) (0.12 mmol, 0.09 g), AcOK (6.55 mmol, 0.64 g) and 1,4-Dioxane (10 mL) to a three-necked flask. Under a nitrogen atmosphere, heat to reflux at 110 °C for 2 hours. After cooling to room temperature, filter the reaction mixture through a diatomaceous earth pad, wash with chloroform, and evaporate the obtained filtrate in vacuo. Purify the obtained residue by silica gel column chromatography using hexane / ethyl acetate as the eluent to obtain intermediate Y1.

[0281] Synthesis of intermediate M4:

[0282] Add raw material A1 (11 mmol, 2.99 g) and intermediate Y1 (10 mmol, 3.86 g) into a three-necked flask, dissolve them with a mixed solvent (70 mL of toluene, 35 mL of ethanol), then add Pd(PPh 3 ) 4 (0.10 mmol, 0.12 g) and 15 mL of 3 mol / L K 2 CO 3 aqueous solution. Heat under reflux for 15 hours under nitrogen protection. Take samples for TLC to confirm the completion of the reaction. After cooling to room temperature, filter the reaction mixture through a diatomaceous earth pad, rinse with chloroform, and evaporate the obtained filtrate under vacuum. Purify the obtained residue by column chromatography on silica gel using hexane / toluene as the eluent to obtain intermediate M4.

[0283] Synthesis of intermediate N4:

[0284] Add intermediate M4 (18.4 mmol, 8.3 g) and cesium carbonate (55.2 mmol, 18.0 g) into a two-necked flask. Add 120 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 40 minutes. Then add raw material C1 (40.5 mmol, 11.3 g) under nitrogen protection. Reflux the solution with magnetic stirring for 21 hours, cool, filter, wash with water, dry, and purify by column chromatography to obtain intermediate N4.

[0285] Synthesis of intermediate J4:

[0286] Dissolve intermediate N4 (5.1 mmol, 4.95 g) in 50 mL of tetrahydrofuran (THF) solution. Slowly add 2.3 mL of a 2.5 M n-butyllithium hexane solution under nitrogen at -78 °C. After stirring at -78 °C for 2.5 hours, slowly add 15 mL of a THF solution of raw material D1 (5.5 mmol, 1.0 g). Then slowly heat the reaction mixture to room temperature and stir overnight. Add 20 mL of dilute hydrochloric acid (1 M) solution, distilled water, and ethyl acetate to the reaction mixture. Separate the aqueous layer and extract it three times with ethyl acetate. Dry the combined organic layers with sodium sulfate and filter. After removing the solvent under reduced pressure, dissolve the crude product in anhydrous dichloromethane, and then slowly add 47% boron trifluoride-diethyl ether. Stir the reaction mixture overnight and quench it slowly with NaHCO 3 aqueous solution. Then separate the aqueous layer and extract it with dichloromethane. Dry with sodium sulfate, filter, and evaporate by rotary evaporation, and purify by column chromatography to obtain intermediate J4.

[0287] Synthesis of intermediate K4:

[0288] To a three-necked flask, add intermediate J4 (20.0 mmol, 21.07 g) successively, add 230 mL of glacial acetic acid, and protect with nitrogen. Cool to 0 °C using a low-temperature bath and strictly avoid light. Add NBS (25 mmol, 4.45 g) in batches, and stir overnight at 0 °C. Concentrate the reaction solution and purify it through a silica gel column to obtain intermediate K4.

[0289] Synthesis of compound 149:

[0290] In a sealed pressure-resistant tube, under nitrogen protection, add intermediate K4 (10 mmol, 11.32 g) and 120 mL of o-dichlorobenzene. Add a 2.5 M n-butyllithium hexane solution (30 mmol, 12 mL) at -78 °C, heat the system to 60 °C and react for 3.5 hours. Then add boron tribromide (15 mmol, 1.5 mL) at 0 °C, transfer to room temperature and continue to react for 7 hours. Then add N,N-diisopropylethylamine (20 mmol, 3.5 mL) to the system at 0 °C, heat to 200 °C and react for 12 hours. After the reaction is completed, reduce the pressure and concentrate the organic layer, and then purify it by silica gel column chromatography to obtain compound 149. The half-peak width in toluene solution (1×10 -5 M) is 29 nm.

[0291] Synthesis of compound 165 in Example 5:

[0292]

[0293]

[0294] Synthesis of intermediate M5:

[0295] Add raw material A1 (11 mmol, 2.99 g) and raw material B5 (10 mmol, 3.3 g) to a three-necked flask, dissolve with a mixed solvent (70 mL of toluene, 35 mL of ethanol), then add Pd(PPh 3 ) 4 (0.10 mmol, 0.12 g), 15 mL of 3 mol / L K 2 CO 3 aqueous solution, and heat to reflux under nitrogen protection for 12.5 hours. Take a sample and spot on a plate to confirm that the reaction is complete. After cooling to room temperature, filter the reaction mixture through a diatomaceous earth pad, rinse with chloroform, and evaporate the obtained filtrate in vacuo. Purify the obtained residue by column chromatography on silica gel using hexane / toluene as the eluent to obtain intermediate M5.

[0296] Synthesis of intermediate N5:

[0297] Add intermediate M5 (18.4 mmol, 7.27 g) and cesium carbonate (55.2 mmol, 18.0 g) into a two-necked flask. Under nitrogen protection, add 120 mL of anhydrous DMF, stir at room temperature for 35 minutes. Under nitrogen protection, add raw material C1 (40.5 mmol, 11.32 g). The solution is refluxed for 22 hours under magnetic stirring, cooled, filtered, washed with water, dried, and purified by column chromatography to obtain intermediate N5.

[0298] Synthesis of intermediate J5:

[0299] Dissolve intermediate N5 (5.1 mmol, 4.66 g) in 50 mL of tetrahydrofuran (THF) solution. Under the condition of nitrogen passing at -78 °C, slowly add 2.3 mL of a 2.5 M n-butyllithium hexane solution; after stirring at -78 °C for 2.5 hours, slowly add 15 mL of a THF solution of raw material D1 (5.5 mmol, 1.0 g). Then slowly heat the reaction mixture to room temperature and stir overnight. Add 20 mL of dilute hydrochloric acid (1 M) solution, distilled water and ethyl acetate to the reaction mixture, separate the aqueous layer, and extract it three times with ethyl acetate. The combined organic layers are dried over sodium sulfate and filtered. After removing the solvent under reduced pressure, dissolve the crude product in anhydrous dichloromethane, and then slowly add 47% boron trifluoride-diethyl ether. The reaction mixture is stirred overnight and quenched slowly with an aqueous NaHCO 3 solution. Then separate the aqueous layer and extract it with dichloromethane. Dry over sodium sulfate, filter, and evaporate by rotary evaporation, and purify by column chromatography to obtain intermediate J5.

[0300] Synthesis of intermediate K5:

[0301] Add intermediate J5 (20.0 mmol, 19.95 g) into a three-necked flask in sequence, add 220 mL of glacial acetic acid, and use nitrogen protection. Cool it to 0 °C with a low-temperature bath and strictly avoid light. Add NBS (25 mmol, 4.45 g) in batches and stir at 0 °C for 12.5 hours. Concentrate the reaction solution and purify it by silica gel column to obtain intermediate K5.

[0302] Synthesis of compound 165:

[0303] In a sealed pressure-resistant tube, under nitrogen protection, add intermediate K5 (10 mmol, 10.76 g) and 120 mL of o-dichlorobenzene. Add a 2.5 M n-butyllithium hexane solution (30 mmol, 12 mL) at -78 °C, heat the system to 60 °C and react for 2 hours. Then add boron tribromide (15 mmol, 1.5 mL) at 0 °C, transfer to room temperature and continue to react for 5.5 hours. Then add N,N-diisopropylethylamine (20 mmol, 3.5 mL) to the system at 0 °C, heat to 200 °C and react for 12 hours. After the reaction is completed, reduce the pressure and concentrate the organic layer, and then purify by silica gel column chromatography to obtain compound 165. In a toluene solution (1×10 -5 M), the half-peak width is 27 nm.

[0304] Synthesis of Compound 208 in Example 6:

[0305]

[0306] Synthesis of Intermediate M6:

[0307] Add raw material A1 (11 mmol, 2.99 g) and raw material B6 (10 mmol, 3.14 g) to a three-necked flask, dissolve with a mixed solvent (70 mL of toluene, 35 mL of ethanol), then add Pd(PPh 3 ) 4 (0.10 mmol, 0.12 g), 15 mL of 3 mol / L K 2 CO 3 aqueous solution, and heat under reflux for 12 hours under nitrogen protection. Take a sample and spot-check the plate to confirm that the reaction is complete. After cooling to room temperature, filter the reaction mixture through a diatomaceous earth pad, wash with chloroform, and evaporate the obtained filtrate in vacuo. Purify the obtained residue by column chromatography on silica gel using hexane / toluene as the eluent to obtain intermediate M6.

[0308] Synthesis of Intermediate N6:

[0309] Add intermediate M6 (18.4 mmol, 6.98 g) and cesium carbonate (55.2 mmol, 18.0 g) to a two-necked flask, add 120 mL of anhydrous DMF under nitrogen protection, stir at room temperature for 25 minutes, add raw material C1 (40.5 mmol, 11.32 g) under nitrogen protection, reflux the solution under magnetic stirring for 20 hours, cool, filter, wash with water, dry, and column to obtain intermediate N6.

[0310] Synthesis of Intermediate J6:

[0311] Dissolve the intermediate N6 (5.1 mmol, 4.58 g) in 50 mL of tetrahydrofuran (THF) solution. Under the condition of nitrogen gas passing at -78 °C, slowly add 2.3 mL of a n-butyllithium (2.5 M, 5.7 mmol) n-hexane solution. After stirring at -78 °C for 1.5 hours, slowly add 15 mL of a THF solution of the raw material D1 (5.5 mmol, 1.0 g). Then slowly heat the reaction mixture to room temperature and stir overnight. Add 20 mL of dilute hydrochloric acid (1 M) solution, distilled water and ethyl acetate to the reaction mixture, separate the aqueous layer, and extract it three times with ethyl acetate. The combined organic layers are dried over sodium sulfate and filtered. After removing the solvent under reduced pressure, dissolve the crude product in anhydrous dichloromethane, and then slowly add 47% boron trifluoride-diethyl ether. Stir the reaction mixture overnight and quench it slowly with an aqueous NaHCO 3 solution. Then separate the aqueous layer and extract it with dichloromethane. Dry it over sodium sulfate, filter, and evaporate it by rotary evaporation, and purify it by column chromatography to obtain the intermediate J6.

[0312] Synthesis of intermediate K6:

[0313] Add the intermediate J6 (20.0 mmol, 19.63 g) to a three-necked flask in sequence, add 220 mL of glacial acetic acid, and protect it with nitrogen. Cool it to 0 °C using a low-temperature bath and strictly avoid light. Add NBS (25 mmol, 4.45 g) in batches and stir at 0 °C for 11.5 hours. Concentrate the reaction solution and purify it by silica gel column to obtain the intermediate K6.

[0314] Synthesis of compound 208:

[0315] In a sealed pressure-resistant tube, under nitrogen protection, add the intermediate K6 (10 mmol, 10.6 g) and 120 mL of o-dichlorobenzene. Add a n-butyllithium (2.5 M) n-hexane solution (30 mmol, 12 mL) at -78 °C, heat the system to 60 °C and react for 2 hours. Then add boron tribromide (15 mmol, 1.5 mL) at 0 °C, transfer it to room temperature and continue to react for 5.5 hours. Then add N,N-diisopropylethylamine (20 mmol, 3.5 mL) to the system at 0 °C, heat it to 200 °C and react for 12 hours. After the reaction is completed, reduce the pressure and concentrate the organic layer, and then purify it by silica gel column chromatography to obtain compound 208. The half-peak width in toluene solution (1×10 -5 M) is 28 nm.

[0316] Synthesis of compound 255 in Example 7:

[0317]

[0318] Synthesis of intermediate B1: Add raw material E1 (1.68 g, 5 mmol) and cesium carbonate (4.07 g, 12.5 mmol) into a two-necked flask, add 50 mL of anhydrous DMF under nitrogen protection, stir at room temperature for 30 min, add raw material C1 (1.4 g, 5 mmol) under nitrogen protection, stir at 140 ° C for 12 h under nitrogen protection, filter, wash with water, dry, and pass through a column with PE:EA=20:1 to obtain intermediate B1.

[0319] Synthesis of intermediate C1: Intermediate B1 (3.03 g, 5.1 mmol) was dissolved in 50 mL of tetrahydrofuran (THF) solution, and 3.8 mL of n-butyl lithium (1.6 M) n-hexane solution was slowly added under nitrogen at 0°C; after stirring at 0°C for 2 hours, 10 mL of tetrahydrofuran solution of raw material F1 (3.71 g, 12.7 mmol) was slowly added. The reaction mixture was then slowly heated to room temperature and stirred overnight. Dilute hydrochloric acid solution, distilled water and ethyl acetate were added to the reaction mixture, the water layer was separated, and extracted three times with ethyl acetate. The combined organic layer was dried over sodium sulfate and filtered. After removing the solvent under reduced pressure, the crude product was dissolved in anhydrous dichloromethane, and then 47% boron trifluoride-diethyl ether was slowly added. The reaction mixture was stirred overnight and treated with NaHCO 3 The aqueous solution was slowly quenched. The aqueous layer was then separated and extracted with dichloromethane. It was dried over sodium sulfate, filtered, and evaporated by rotary concentrator and passed through a column to obtain intermediate C1.

[0320] Synthesis of intermediate D1: Under nitrogen atmosphere, intermediate C1 (1.86 g, 2.5 mmol) was dissolved in 50 mL toluene solution, and raw intermediate G1 (0.70 g, 2.5 mmol), tri-tert-butylphosphine (0.025 g, 0.125 mmol), sodium tert-butoxide (0.62 g, 6.5 mmol) and palladium acetate (0.01 g, 0.04 mmol) were added and stirred vigorously. The resulting mixture was refluxed at 105 ° C for 10 hours and then allowed to reach room temperature. Ethyl acetate (100 mL) was then added. The mixture was washed 3 times with deionized water (100 mL). After drying over anhydrous magnesium sulfate overnight, ethyl acetate was evaporated under reduced pressure. The remaining mixture was poured into 100 mL of petroleum ether under stirring and filtered to obtain intermediate D1.

[0321] Synthesis of Compound 255: Under a nitrogen atmosphere at 0 °C, 10 mL of a 1.6 M solution of tert-butyllithium in n-pentane was slowly added to 300 mL of a solution of Intermediate D1 (11.77 g, 12.5 mmol) in tert-butylbenzene. After stirring at 60 °C for 2 hours, n-pentane was removed in vacuo. After adding boron tribromide (6.26 g, 25 mmol) at 0 °C, the reaction mixture was stirred at room temperature for 1 hour. After adding N,N-diisopropylethylamine (DIEA) (3.25 g, 25.2 mmol) at 0 °C, the reaction mixture was allowed to reach room temperature. After stirring at 130 °C for 6 hours, the reaction mixture was cooled to room temperature. Methanol was added to the reaction mixture to remove residual BBr 3 . The mixture was separated and extracted with water and dichloromethane. The combined organic layers were condensed in vacuo, passed through a column, and Compound 255 was obtained.

[0322] Synthesis of Compound 48 in Example 8:

[0323]

[0324] Synthesis of Intermediate M8:

[0325] Raw material A1 (10 mmol, 2.71 g) and raw material B8 (10 mmol, 1.72 g) were added to a three-necked flask, dissolved in a mixed solvent (60 mL of toluene, 30 mL of ethanol), and then Pd(PPh 3 ) 4 (0.10 mmol, 0.12 g), 15 mL of an aqueous solution of 3 mol / L K 2 CO 3 were added. The reaction was heated under reflux for 12.5 hours under nitrogen protection. Samples were taken for TLC to confirm complete reaction. After cooling to room temperature, the reaction mixture was filtered through a pad of diatomaceous earth, rinsed with chloroform, and the resulting filtrate was evaporated in vacuo. The residue obtained was purified by column chromatography on silica gel using hexane / toluene as the eluent to obtain Intermediate M8.

[0326] Synthesis of Intermediate N8:

[0327] Intermediate M8 (20 mmol, 6.38 g) and cesium carbonate (50 mmol, 16.3 g) were added to a two-necked flask. 80 mL of anhydrous DMF was added under nitrogen protection, and the mixture was stirred at room temperature for 35 minutes. Raw material C1 (50 mmol, 14.0 g) was added under nitrogen protection, and the solution was refluxed with magnetic stirring for 22 hours. After cooling, filtering, washing with water, drying, and passing through a column, Intermediate N8 was obtained.

[0328] Synthesis of Intermediate J8:

[0329] Dissolve the intermediate N8 (10 mmol, 8.38 g) in 100 mL of tetrahydrofuran (THF) solution. Under the condition of nitrogen passing at -78 °C, slowly add 4.4 mL of a 2.5 M n-butyllithium solution in n-hexane (11 mmol); after stirring at -78 °C for 2.5 hours, slowly add 30 mL of a THF solution of the raw material D1 (11 mmol, 1.98 g). Then slowly heat the reaction mixture to room temperature and stir overnight. Add 40 mL of dilute hydrochloric acid (1 M) solution, distilled water, and ethyl acetate to the reaction mixture, separate the aqueous layer, and extract it three times with ethyl acetate. The combined organic layers are dried over sodium sulfate and filtered. After removing the solvent under reduced pressure, dissolve the crude product in anhydrous dichloromethane, and then slowly add 47% boron trifluoride-diethyl ether. Stir the reaction mixture overnight and quench it slowly with an aqueous NaHCO 3 aqueous solution. Then separate the aqueous layer and extract it with dichloromethane. Dry it over sodium sulfate, filter, and evaporate by rotary evaporation, and purify by column chromatography to obtain the intermediate J8.

[0330] Synthesis of intermediate K8:

[0331] Add the intermediate J8 (10.0 mmol, 9.21 g) to a three-necked flask in sequence, add 100 mL of glacial acetic acid, protect it with nitrogen, cool it to 0 °C using a low-temperature bath and strictly avoid light, and add NBS (15.0 mmol, 2.67 g) in batches. Stir at 0 °C for 12.5 hours. Concentrate the reaction solution and purify it by silica gel column to obtain the intermediate K8.

[0332] Synthesis of compound 48:

[0333] In a sealed pressure-resistant tube, under nitrogen protection, add the intermediate K8 (10 mmol, 10.0 g) and 120 mL of tert-butylbenzene. Add a 2.5 M n-butyllithium solution in n-hexane (12 mmol, 4.8 mL) at -78 °C, heat the system to 60 °C and react for 2 hours, then add boron tribromide (15 mmol, 1.5 mL) at 0 °C, transfer it to room temperature and continue to react for 5.5 hours, then add N,N-diisopropylethylamine (20 mmol, 3.5 mL) to the system at 0 °C, heat to 165 °C and react for 12 hours. After the reaction is completed, reduce the pressure and concentrate the organic layer, and then purify it by silica gel column chromatography to obtain compound 48. The half-peak width in toluene solution (1×10 -5 M) is 24 nm.

[0334] Synthesis of compound 64 in Example 9:

[0335]

[0336] Synthesis of intermediate M9:

[0337] Add raw material A1 (10 mmol, 2.71 g) and raw material B9 (10 mmol, 1.72 g) into a three-necked flask, dissolve them with a mixed solvent (60 mL of toluene, 30 mL of ethanol), then add Pd(PPh 3 ) 4 (0.10 mmol, 0.12 g), 15 mL of 3 mol / L K 2 CO 3 aqueous solution. Heat under reflux for 12.5 hours under nitrogen protection. Take a sample and spot it on a TLC plate to confirm the completion of the reaction. After cooling to room temperature, filter the reaction mixture through a diatomaceous earth pad, rinse with chloroform, and evaporate the obtained filtrate under vacuum. Purify the obtained residue by column chromatography on silica gel using hexane / toluene as the eluent to obtain intermediate M9.

[0338] Synthesis of intermediate N9:

[0339] Add intermediate M9 (20 mmol, 6.38 g) and cesium carbonate (50 mmol, 16.3 g) into a two-necked flask. Add 80 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 35 minutes. Then add raw material C1 (50 mmol, 14.0 g) under nitrogen protection. Reflux the solution with magnetic stirring for 22 hours, cool, filter, wash with water, dry, and column-chromatograph to obtain intermediate N9.

[0340] Synthesis of intermediate J9:

[0341] Dissolve intermediate N9 (10 mmol, 8.38 g) in 100 mL of tetrahydrofuran (THF) solution. Under the condition of nitrogen passing at -78 °C, slowly add 4.4 mL of a 2.5 M n-butyllithium hexane solution; after stirring at -78 °C for 2.5 hours, slowly add 30 mL of a THF solution of raw material D1 (11 mmol, 1.98 g). Then slowly heat the reaction mixture to room temperature and stir overnight. Add 40 mL of dilute hydrochloric acid (1 M) solution, distilled water, and ethyl acetate to the reaction mixture, separate the aqueous layer, and extract it three times with ethyl acetate. Dry the combined organic layers with sodium sulfate and filter. After removing the solvent under reduced pressure, dissolve the crude product in anhydrous dichloromethane, and then slowly add 47% boron trifluoride-diethyl ether. Stir the reaction mixture overnight and quench it slowly with a NaHCO 3 aqueous solution. Then separate the aqueous layer and extract it with dichloromethane. Dry it with sodium sulfate, filter, and evaporate by rotary evaporation, and column-chromatograph to obtain intermediate J9.

[0342] Synthesis of intermediate K9:

[0343] To a three-necked flask, add intermediate J9 (10.0 mmol, 9.21 g) successively, add 100 mL of glacial acetic acid, and protect with nitrogen. Cool to 0 °C using a low-temperature bath and strictly avoid light. Add NBS (15.0 mmol, 2.67 g) in batches, and stir at 0 °C for 12.5 hours. Concentrate the reaction solution and purify it by silica gel column to obtain intermediate K9.

[0344] Synthesis of Compound 64:

[0345] In a sealed pressure-resistant tube, under nitrogen protection, add intermediate K9 (10 mmol, 10.0 g) and 120 mL of tert-butylbenzene. Add a 2.5 M solution of n-butyllithium in n-hexane (12 mmol, 4.8 mL) at -78 °C, heat the system to 60 °C and react for 2 hours. Then add boron tribromide (15 mmol, 1.5 mL) at 0 °C, transfer to room temperature and continue to react for 5.5 hours. Then add N,N-diisopropylethylamine (20 mmol, 3.5 mL) to the system at 0 °C, heat to 165 °C and react for 12 hours. After the reaction is completed, reduce the pressure and concentrate the organic layer, and then purify it by silica gel column chromatography to obtain Compound 64. The half-peak width in toluene solution (1×10 -5 M) is 24 nm.

[0346] Synthesis of Compound 533 in Example 10:

[0347]

[0348]

[0349] Synthesis of Intermediate M10:

[0350] Add raw material A1 (10 mmol, 2.71 g) and raw material B10 (10 mmol, 2.46 g) to a three-necked flask, dissolve with a mixed solvent (60 mL of toluene, 30 mL of ethanol), then add Pd(PPh 3 ) 4 (0.10 mmol, 0.12 g) and 15 mL of 3 mol / L K 2 CO 3 aqueous solution. Heat under reflux and react for 12.5 hours under nitrogen protection. Take a sample and spot on a plate to confirm that the reaction is complete. After cooling to room temperature, filter the reaction mixture through a diatomaceous earth pad, rinse with chloroform, and evaporate the obtained filtrate in vacuo. Purify the obtained residue by column chromatography on silica gel using hexane / toluene as the eluent to obtain intermediate M10.

[0351] Synthesis of Intermediate N10:

[0352] Add intermediate M10 (20 mmol, 7.86 g) and cesium carbonate (50 mmol, 16.3 g) to a two-necked flask. Under nitrogen protection, add 80 mL of anhydrous DMF, stir at room temperature for 35 minutes, and then add raw material C1 (50 mmol, 14.0 g) under nitrogen protection. The solution is refluxed for 22 hours with magnetic stirring, cooled, filtered, washed with water, dried, and purified by column chromatography to obtain intermediate N10.

[0353] Synthesis of intermediate J10:

[0354] Dissolve intermediate N10 (10 mmol, 9.12 g) in 100 mL of tetrahydrofuran (THF) solution. Under nitrogen flow at -78 °C, slowly add 4.4 mL of a 2.5 M n-butyllithium solution in hexane. After stirring at -78 °C for 2.5 hours, slowly add 30 mL of a THF solution of raw material D1 (11 mmol, 1.98 g). Then the reaction mixture is slowly heated to room temperature and stirred overnight. Add 40 mL of dilute hydrochloric acid (1 M) solution, distilled water, and ethyl acetate to the reaction mixture, separate the aqueous layer, and extract it three times with ethyl acetate. The combined organic layers are dried over sodium sulfate and filtered. After removing the solvent under reduced pressure, the crude product is dissolved in anhydrous dichloromethane, and then 47% boron trifluoride-diethyl ether is slowly added. The reaction mixture is stirred overnight and quenched slowly with an aqueous NaHCO 3 solution. Then the aqueous layer is separated and extracted with dichloromethane. It is dried over sodium sulfate, filtered, and evaporated by rotary evaporation, and purified by column chromatography to obtain intermediate J10.

[0355] Synthesis of intermediate K10:

[0356] Add intermediate J10 (10.0 mmol, 9.95 g) to a three-necked flask in sequence, add 100 mL of glacial acetic acid, and use nitrogen protection. Cool to 0 °C with a low-temperature bath and strictly avoid light. Add NBS (15.0 mmol, 2.67 g) in batches and stir at 0 °C for 12.5 hours. Concentrate the reaction solution and purify it by silica gel column to obtain intermediate K10.

[0357] Synthesis of compound 533:

[0358] In a sealed pressure-resistant tube, under nitrogen protection, add intermediate K10 (10 mmol, 10.7 g) and 120 mL of tert-butylbenzene. Add a 2.5 M n-butyllithium hexane solution (12 mmol, 4.8 mL) at -78 °C, heat the system to 60 °C and react for 2 hours. Then add boron tribromide (15 mmol, 1.5 mL) at 0 °C, transfer to room temperature and continue to react for 5.5 hours. Then add N,N-diisopropylethylamine (20 mmol, 3.5 mL) to the system at 0 °C, heat to 200 °C and react for 12 hours. After the reaction, reduce the pressure and concentrate the organic layer, and then purify by silica gel column chromatography to obtain compound 533. In a toluene solution (1×10 -5 M), the half-peak width is 24 nm.

[0359] Synthesize the following target compounds with reference to the preparation process of compound 255 in Example 7; the reaction conditions are the same, and the starting material C1 used is the same, except that the starting materials E, starting materials F and intermediate G listed in the following table are used;

[0360]

[0361] Synthesis of the series of intermediate G:

[0362]

[0363] Synthesis of intermediate G3: Under the condition of continuous stirring with nitrogen, add NaO(t-Bu) (3.36 g, 35 mmol), 100 mL of dehydrated toluene, raw material R1 (8.45 g, 30 mmol), raw material P1 (6.55 g, 32.5 mmol) and Pd-Cy-vBRIDP catalyst (0.25 g, 0.5 mmol) in sequence. Heat the obtained suspension to 100 °C with silicone oil and continuously stir at 100 °C for 2 hours under nitrogen. Extract three times with ethyl acetate, combine the organic phases, then dry with anhydrous sodium sulfate, filter and concentrate to obtain the crude product. Purify by recrystallization (ethyl acetate / petroleum ether) to obtain intermediate G3.

[0364]

[0365] Synthesis of intermediate G5: The raw material R3 (7.08 g, 25 mmol) was dissolved in 100 mL of toluene solution, and the raw material P3 (6.41 g, 25 mmol), tri-tert-butylphosphine (0.26 g, 1.25 mmol), sodium tert-butoxide (6.25 g, 65 mmol) and palladium acetate (0.09 g, 0.4 mmol) were added and stirred vigorously. The resulting mixture was refluxed at 105 ° C for 11 hours and then allowed to reach room temperature. Ethyl acetate (100 mL) was then added. The mixture was washed 3 times with deionized water (100 mL). After drying over anhydrous magnesium sulfate overnight, the ethyl acetate was evaporated under reduced pressure. The remaining mixture was poured into 100 mL of petroleum ether under stirring. Intermediate G5 was obtained after filtration.

[0366] The structural characteristics of the compounds obtained in each example are shown in Table 1

[0367] Table 1

[0368]

[0369]

[0370] Compound 255 has a PLQY of 98% and a FWHM of 25 nm;

[0371] Compound 373 has a PLQY of 94% and a FWHM of 26 nm;

[0372] Compound 438 has a PLQY of 98% and a FWHM of 25 nm;

[0373] Compound 20 has a PLQY of 97% and a FWHM of 25 nm;

[0374] Note: The PLQY (fluorescence quantum yield) and FWHM (half-maximum width) of compound 255, compound 373, compound 438 and compound 20 were measured in the thin film state by Horiba's Fluorolog-3 series fluorescence spectrometer.

[0375] The following describes in detail the application effect of the OLED material synthesized by the present invention in the device through device examples 1-13 and device comparison examples 1-2. The device manufacturing process of device examples 2-13 and device comparison examples 1-2 of the present invention is exactly the same as that of device example 1, and the same substrate material and electrode material are used. The film thickness of the electrode material is also the same. The difference is that the light-emitting layer material in the device is replaced. The layer structure and test results of each device embodiment are shown in Table 2-1 and Table 3 respectively.

[0376] Device Example 1

[0377] like Figure 1As shown, the transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (with a film thickness of 150 nm) is washed, that is, washed successively with a cleaning agent (Semiclean M-L20), pure water, and then dried, and then washed with ultraviolet-ozone to remove organic residues on the surface of the transparent ITO. On the ITO anode layer 2 after the above washing, using a vacuum evaporation device, HT-1 and HI-1 with a film thickness of 10 nm are evaporated as the hole injection layer 3, and the mass ratio of HT-1 and HI-1 is 97:3. Then, HT-1 with a thickness of 60 nm is evaporated as the hole transport layer 4. Subsequently, EB-1 with a thickness of 30 nm is evaporated as the electron blocking layer 5. After the evaporation of the above electron blocking material is completed, the light-emitting layer 6 of the OLED light-emitting device is fabricated. GH-1 and GH-2 are used as host materials, and compound 5 is used as a doping material. The mass ratio of GH-1, GH-2, and compound 5 is 69:30:1, and the film thickness of the light-emitting layer is 30 nm. After the above light-emitting layer 6, HB-1 is continuously evaporated by vacuum evaporation, with a film thickness of 5 nm, and this layer is the hole blocking layer 7. After the above hole blocking layer 7, ET-1 and Liq are continuously evaporated by vacuum evaporation, with a mass ratio of ET-1 and Liq of 1:1 and a film thickness of 30 nm, and this layer is the electron transport layer 8. On the electron transport layer 8, a LiF layer with a film thickness of 1 nm is fabricated by a vacuum evaporation device, and this layer is the electron injection layer 9. On the electron injection layer 9, a Mg:Ag electrode layer with a film thickness of 80 nm is fabricated by a vacuum evaporation device, and the mass ratio of Mg and Ag is 1:9, and this layer is used as the cathode layer 10.

[0378] The application effects of the OLED materials synthesized by the present invention in devices are described in detail below through device Examples 14-26 and device Comparative Examples 3-4. The manufacturing processes of the devices in device Examples 15-26 and device Comparative Examples 3-4 are exactly the same as those in device Example 14, and the same substrate materials and electrode materials are used, and the film thicknesses of the electrode materials are also kept consistent. The difference is that the light-emitting layer materials in the devices are replaced. The layer structures and test results of each device example are shown in Tables 2-2 and 3 respectively.

[0379] Device Example 14

[0380] The transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (with a film thickness of 150 nm) is washed, that is, washed successively with a cleaning agent (Semiclean M-L20), pure water, and then dried, and then washed with ultraviolet-ozone to remove organic residues on the surface of the transparent ITO. On the ITO anode layer 2 after the above washing, using a vacuum evaporation device, HT-1 and HI-1 with a film thickness of 10 nm are evaporated as the hole injection layer 3, and the mass ratio of HT-1 and HI-1 is 97:3. Then, HT-1 with a thickness of 60 nm is evaporated as the hole transport layer 4. Subsequently, EB-1 with a thickness of 30 nm is evaporated as the electron blocking layer 5. After the evaporation of the above electron blocking material is completed, the light-emitting layer 6 of the OLED light-emitting device is fabricated. GH-1 and GH-2 are used as the host materials, GD-1 is used as the first doping material, and compound 5 is used as the second doping material. The mass ratio of GH-1, GH-2, GD-1, and compound 5 is 66:30:3:1, and the film thickness of the light-emitting layer is 30 nm. After the above light-emitting layer 6, HB-1 is continuously vacuum-evaporated with a film thickness of 5 nm, and this layer is the hole blocking layer 7. After the above hole blocking layer 7, ET-1 and Liq are continuously vacuum-evaporated, and the mass ratio of ET-1 and Liq is 1:1, with a film thickness of 30 nm, and this layer is the electron transport layer 8. On the electron transport layer 8, a LiF layer with a film thickness of 1 nm is fabricated through a vacuum evaporation device, and this layer is the electron injection layer 9. On the electron injection layer 9, a Mg:Ag electrode layer with a film thickness of 80 nm is fabricated through a vacuum evaporation device, and the mass ratio of Mg and Ag is 1:9, and this layer is used as the cathode layer 10.

[0381] The molecular structural formulas of the related materials are as follows:

[0382]

[0383] After completing the OLED light-emitting device as described above, the anode and cathode are connected by a known driving circuit, and the current efficiency and the lifetime of the device are measured. The device examples and comparative examples prepared by the same method are shown in Tables 2-1 and 2-2; the test results of the current efficiency and lifetime of the obtained devices are shown in Table 3.

[0384] Table 2-1

[0385]

[0386]

[0387]

[0388] Table 2-2

[0389]

[0390] Table 3

[0391]

[0392] Note: The current efficiency and emission peak are measured using an IVL (current-voltage-luminance) test system (Suzhou FushiDa Scientific Instruments Co., Ltd.); the lifetime test system is the EAS-62C OLED device lifetime tester from System Technology Co., Ltd. in Japan; LT95 refers to the time when the device luminance decays to 95%; all data are measured at 10 mA / cm 2 under the test.

[0393] From the device data results in Table 3, it can be seen that the emission peak of the compound of the present invention is between 510 and 550 nm, and the green emission effect can be well achieved; compared with Device Comparative Examples 1 and 3, for the organic light-emitting devices of the present invention, whether in the single-doping system or the double-doping system, the device efficiency and lifetime are greatly improved compared with the OLED devices of known materials; compared with Device Comparative Examples 2 and 4, for the organic light-emitting devices of the present invention, whether in the single-doping system or the double-doping system, the lifetime is greatly improved compared with the OLED devices of known materials.

[0394] In summary, the above are only the preferred embodiments of the present invention and are not intended to limit the present invention. Any modifications, equivalent replacements, improvements, etc. made within the spirit and principle of the present invention shall be included within the protection scope of the present invention.

Claims

1. A boron-containing resonance organic compound, characterized in that: The structure of the boron-containing resonance organic compound is shown in the general formula (1): In general formula (1), R 1 , R 3 ~R 19 each independently represents, each time it appears, a hydrogen atom, a deuterium atom, a fluorine atom, a substituted or unsubstituted C 1 ~C 10 alkyl group, a substituted or unsubstituted C 3 ~C 10 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted condensed tetraphenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted group, a substituted or unsubstituted di-p-terphenyl group, one of; R 2 Each occurrence represents a fluorine atom, a substituted or unsubstituted C 1 ~C 10 alkyl group, a substituted or unsubstituted C 3 ~C 10 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted condensed tetraphenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted group, a substituted or unsubstituted terphenyl group, one of the following; M 1 represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted spirofluorene group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted meta-terphenyl group; M 2 represented as phenyl, deuterated phenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl; X represents a carbon atom or a silicon atom; The substituents used to replace the above-mentioned replaceable groups are each independently selected from a deuterium atom, a fluorine atom, an alkyl group having 1 to 6 carbon atoms, 1 1 to 10 alkyl group, a deuterium-substituted C 1 to 10 alkyl group, or one or more thereof.

2. A boron-containing resonance organic compound, characterized in that The structure of the boron-containing resonance organic compound is shown in any one of the general formulas (1-1) to (1-3): In General Formulas (1-1) to (1-3), R 1 , R 3 -R 25 Each occurrence, which may be the same or different, represents a hydrogen atom, a deuterium atom, a fluorine atom, a substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted C 3 to C 10 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted condensed tetraphenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted group, a substituted or unsubstituted di-p-terphenyl group, and the like; R 2 Each occurrence represents a fluorine atom, a substituted or unsubstituted C 1 ~C 10 alkyl group, a substituted or unsubstituted C 3 ~C 10 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted condensed tetraphenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted group, a substituted or unsubstituted terphenylene group, one of; Ar 3 Each occurrence of the same or different represents substituted or unsubstituted C 1 ~C 10 alkyl, substituted or unsubstituted C 3 ~C 10 cycloalkyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted condensed tetraphenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted group, or one of substituted or unsubstituted di-p-terphenyl; X represents C or Si; The substituents for the substituting groups are each independently selected from deuterium, fluorine atoms, C 1 ~C 10 alkyl, deuterium-substituted C 1 ~C 10 alkyl, and any one of them.

3. The boron-containing resonance organic compound according to claim 2, characterized in that The structure of the boron-containing resonance organic compound is shown in any one of the general formulas (1-4) to (1-6): In General Formulas (1-4) to (1-6), the meanings of R 2 , R 7 , R 10 , R 13 , R 16 , R 18 , R 21 and X are the same as those defined in Claim 2; Ar 3 represents substituted or unsubstituted C 1 ~C 10 alkyl, substituted or unsubstituted C 3 ~C 10 cycloalkyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted condensed tetraphenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted group, or one of substituted or unsubstituted di-p-terphenyl; The substituents for the substituting groups are each independently selected from deuterium, fluorine atoms, C 1 ~C 10 alkyl groups, deuterium-substituted C 1 ~C 10 alkyl groups, and any one of them.

4. The boron-containing resonance organic compound according to claim 2, characterized in that The structure of the boron-containing resonance organic compound is shown in any one of the general formulas (1-7), (1-8), (1-10) to (1-12): In General Formula (1-7), General Formula (1-8), General Formula (1-10) to General Formula (1-12), each occurrence of R, which may be the same or different, represents a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a substituted or unsubstituted C 1 ~C 10 alkyl group, a substituted or unsubstituted C 3 ~C 10 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted condensed tetraphenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted group, a substituted or unsubstituted di-p-terphenyl group, and the like; X represents C or Si; The substituents for the substituting groups are each independently selected from deuterium, fluorine atoms, C 1 ~C 10 alkyl groups, deuterium-substituted C 1 ~C 10 alkyl groups, and any one of them.

5. The boron-containing resonance organic compound according to claim 1, characterized in that Said R 1 , R 3 -R 19 are each independently represented by a hydrogen atom, a deuterium atom, a fluorine atom, an adamantyl group, a methyl group, a deuterated methyl group, a trifluoromethyl group, an ethyl group, a deuterated ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a 9,9-dimethylfluorenyl group, a spirofluorene group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group, an isopropyl-substituted phenyl group, a tert-butyl-substituted phenyl group, a methyl-substituted biphenyl group, an ethyl-substituted biphenyl group, an isopropyl-substituted biphenyl group, a tert-butyl-substituted biphenyl group, a deuterated methyl-substituted phenyl group, a deuterated ethyl-substituted phenyl group, a deuterated isopropyl-substituted phenyl group, a deuterated tert-butyl-substituted phenyl group, a deuterated methyl-substituted biphenyl group, a deuterated ethyl-substituted biphenyl group, a deuterated isopropyl-substituted biphenyl group, or a deuterated tert-butyl-substituted biphenyl group; The R 2 Each occurrence represents one of a fluorine atom, adamantyl, methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopentyl, deuterated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, naphthyl, anthracenyl, phenanthryl, 9,9-dimethylfluorenyl, spirofluorene, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl; The M 1 is one of phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, naphthyl, 9,9-dimethylfluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl; The M 2 is represented by one of phenyl, deuterated phenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, and tert-butyl-substituted phenyl.

6. The boron-containing resonance organic compound according to claim 2, characterized in that Said R 1 , R 3 -R 25 are each independently represented by one of a hydrogen atom, a deuterium atom, a fluorine atom, an adamantyl group, a methyl group, a deuterated methyl group, a trifluoromethyl group, an ethyl group, a deuterated ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a 9,9-dimethylfluorenyl group, a spirofluorene group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group, an isopropyl-substituted phenyl group, a tert-butyl-substituted phenyl group, a methyl-substituted biphenyl group, an ethyl-substituted biphenyl group, an isopropyl-substituted biphenyl group, a tert-butyl-substituted biphenyl group, a deuterated methyl-substituted phenyl group, a deuterated ethyl-substituted phenyl group, a deuterated isopropyl-substituted phenyl group, a deuterated tert-butyl-substituted phenyl group, a deuterated methyl-substituted biphenyl group, a deuterated ethyl-substituted biphenyl group, a deuterated isopropyl-substituted biphenyl group, a deuterated tert-butyl-substituted biphenyl group; The R 2 Each occurrence represents one of a fluorine atom, adamantyl, methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopentyl, deuterated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, naphthyl, anthryl, phenanthryl, 9,9-dimethylfluorenyl, spirofluorene, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl; The Ar 3 are each independently represented by phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, naphthyl, anthryl, phenanthryl, 9,9-dimethylfluorenyl, spirofluorene, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, or deuterated tert-butyl-substituted biphenyl.

7. The boron-containing resonance organic compound according to claim 3, characterized in that The R 7 , R 10 , R 13 , R 16 , R 18 , R 21 are each independently represented by one of a hydrogen atom, a deuterium atom, a fluorine atom, an adamantyl group, a methyl group, a deuterated methyl group, a trifluoromethyl group, an ethyl group, a deuterated ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a 9,9-dimethylfluorenyl group, a spirofluorene group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group, an isopropyl-substituted phenyl group, a tert-butyl-substituted phenyl group, a methyl-substituted biphenyl group, an ethyl-substituted biphenyl group, an isopropyl-substituted biphenyl group, a tert-butyl-substituted biphenyl group, a deuterated methyl-substituted phenyl group, a deuterated ethyl-substituted phenyl group, a deuterated isopropyl-substituted phenyl group, a deuterated tert-butyl-substituted phenyl group, a deuterated methyl-substituted biphenyl group, a deuterated ethyl-substituted biphenyl group, a deuterated isopropyl-substituted biphenyl group, and a deuterated tert-butyl-substituted biphenyl group; The R 2 are each independently represented by one of a fluorine atom, adamantyl, methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopentyl, deuterated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, naphthyl, anthryl, phenanthryl, 9,9-dimethylfluorenyl, spirofluorene, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl; The Ar 3 are each independently represented by one of phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, naphthyl, anthryl, phenanthryl, 9,9-dimethylfluorenyl, spirofluorene, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl.

8. The boron-containing resonance organic compound according to claim 4, characterized in that R represents one of a hydrogen atom, a deuterium atom, a fluorine atom, an adamantyl group, a methyl group, a deuterated methyl group, a trifluoromethyl group, an ethyl group, a deuterated ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a 9,9-dimethylfluorenyl group, a spirofluorene group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group, an isopropyl-substituted phenyl group, a tert-butyl-substituted phenyl group, a methyl-substituted biphenyl group, an ethyl-substituted biphenyl group, an isopropyl-substituted biphenyl group, a tert-butyl-substituted biphenyl group, a deuterated methyl-substituted phenyl group, a deuterated ethyl-substituted phenyl group, a deuterated isopropyl-substituted phenyl group, a deuterated tert-butyl-substituted phenyl group, a deuterated methyl-substituted biphenyl group, a deuterated ethyl-substituted biphenyl group, a deuterated isopropyl-substituted biphenyl group, a deuterated tert-butyl-substituted biphenyl group.

9. The boron-containing resonance organic compound according to claim 1, characterized in that Said R 1 , R 3 -R 19 Are each independently represented by the following structures: A hydrogen atom, any one of; The R 2 Each occurrence is represented by the following structure: any one of; The M 1 is represented as any one of the following ring structures: The said M 2 is represented as the following ring structure: wherein Z is represented as C-R a ; R a Each occurrence is independently represented by one of a hydrogen atom, a deuterium atom, a fluorine atom, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, and a deuterated tert-butyl group.

10. The boron-containing resonance organic compound according to claim 2, characterized in that Said R 1 , R 3 -R 25 Are each independently represented by the following structures: A hydrogen atom, any one of; The said R 2 Each occurrence is represented as the following structure: any one of; The Ar 3 is represented in the structure shown below: Any one of them.

11. The boron-containing resonance organic compound according to claim 3, characterized in that Said R 7 、R 10 、R 13 、R 16 、R 18 、R 21 are each independently represented as the following structures: A hydrogen atom, any one of; The R 2 are respectively independently represented in the following structures: any one of; The Ar 3 is represented in the following structure: Any one of them.

12. The boron-containing resonance organic compound according to claim 4, characterized in that R represents the following structure: Hydrogen atom, Any one of them.

13. A boron-containing resonance organic compound, characterized in that: The specific structural formula of the boron-containing resonance organic compound is any one of the following structures:

14. An organic electroluminescent device, sequentially comprising a substrate, a first electrode, a second electrode and a functional layer, the functional layer being located between the first electrode and the second electrode, characterized in that: The functional layer contains the boron-containing resonance organic compound according to any one of claims 1-13.

15. The organic electroluminescent device according to claim 14, wherein, the functional layer includes a light-emitting layer, the light-emitting layer includes a host material and a doping material, and the doping material is the boron-containing resonance organic compound according to any one of claims 1-13.

16. The organic electroluminescent device according to claim 14, wherein, the functional layer includes a light-emitting layer, the light-emitting layer includes a first host material, a second host material and a doping material, at least one of the first host material and the second host material is a TADF material, and the doping material is the boron-containing resonance organic compound according to any one of claims 1-13.

17. The organic electroluminescent device according to claim 14, wherein, the functional layer includes a light-emitting layer, the light-emitting layer includes a host material, an exciton sensitizing material and a doping material, the exciton sensitizing material is a metal element-containing complex, and the doping material is the boron-containing resonance organic compound according to any one of claims 1-13.

18. A material for an organic electroluminescent device, wherein, it contains the boron-containing resonance organic compound according to any one of claims 1-13.

19. An application of the boron-containing resonance organic compound according to any one of claims 1-13, wherein, it is applied to an organic electroluminescent device.

20. The application according to claim 19, wherein, the organic light-emitting functional layer includes a light-emitting layer, and the application of the boron-containing resonance organic compound according to any one of claims 1-14 is to the light-emitting layer.

21. A display element, wherein, it includes the organic electroluminescent device according to any one of claims 14-17.

22. A lighting device, wherein, it includes the organic electroluminescent device according to any one of claims 14-17.

23. An electronic device, wherein, it is equipped with the organic electroluminescent device according to any one of claims 14-17.

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