Boron-containing resonant organic compounds and organic electroluminescent devices containing same

Abstract

The present invention relates to a boron-containing resonant organic compound and an organic electroluminescent device containing the same, which belongs to the field of semiconductor technology. The structure of the compound provided in 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 in the light-emitting layer of the organic electroluminescent device, thereby improving the life of the device.

Description

[Technical Field]

[0001] The present invention relates to the field of semiconductor technology, and in particular to boron-containing resonant organic compounds and organic electroluminescent devices containing same. [Background technology]

[0002] Compared to liquid crystal displays (LCDs), organic light-emitting diodes (OLEDs) boast lightweight, thin, high color contrast, low power consumption, fast response, high definition, flexibility, and other technical advantages. OLEDs are expected to become the mainstream of future display terminal products. With the advent of the 5G era, the new information display industry urgently needs iterative development. Initial low-color gamut standards (BT.709 and DCIP3) can no longer meet the technological development demands of high-quality display products. To meet the performance requirements for ultra-high definition and high image quality in display products, the next-generation display standard (BT.2020) is pushing OLED emitting materials toward high color purity. This requires core emitting materials to have narrower emission spectra. Currently available OLEDs use conventional fluorescent triplet-triplet conversion (TTF) technology for red, green, and blue light. Although this technology has low efficiency, it provides high color purity and has already nearly met the BT.2020 display standard. Phosphorescent technology is used for green and red light. This technology offers high efficiency, and red light is approaching the BT.2020 display standard. However, green light is limited by the wide phosphorescent spectrum and is far from the requirements for high-definition displays. Therefore, it is extremely important to develop green OLED materials with high color purity.

[0003] Since 2020, a number of green light-emitting materials with narrow full width at half maximum (FWHM<30 nm) based on boron-nitrogen resonance structures have been 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.), demonstrating that these materials have extremely high color purity and efficiency, have therefore become a trend in the development of green OLEDs with high color purity. However, the development of green light-emitting materials with ultra-high color purity, including boron-nitrogen structures, remains challenging, and existing materials have drawbacks in efficiency and lifetime, making them difficult to meet the requirements for mass production. The development of green emitting materials with narrow full width at half maximum based on boron-nitrogen resonance structures and meeting the requirements of practical applications will be a key technology for next-generation display devices with high color purity, wide color gamut coverage, high efficiency, and strong immersive feeling.

[0004] Additionally, sensitization technology combines triplet exciton-sensitized materials (including, but not limited to, TADF materials and phosphorescent materials) with fluorescent doping materials. The triplet exciton-sensitized materials used as exciton-sensitizing media transfer energy to the fluorescent doping materials through energy transfer by fully utilizing triplet excitons. In this case, 100% internal quantum efficiency of the device can be achieved. This technology overcomes the insufficient exciton utilization of fluorescent doping materials and effectively achieves the advantages of fluorescent doping materials, such as high fluorescence quantum yield, high device stability, high color purity, and low cost, providing the prospect for widespread application in OLEDs. Sensitization technology can achieve efficiency comparable to phosphorescence and a relatively narrow full width at half maximum. Therefore, the development of sensitization technology based on boron-based emissive materials with narrow full width at half maximum offers unique advantages and strong potential for the BT.2020 display standard. Summary of the Invention [Problem to be solved by the invention]

[0005] The present invention has been made in view of the above-mentioned problems of the prior art, and aims to provide a boron-containing resonant organic compound and an organic electroluminescent device containing the same. The compound of the present invention can be used as a green light doping material in the light-emitting layer of an organic electroluminescent device, and can significantly improve the life of the device. [Means for solving the problem]

[0006] The present invention provides the following technical solution: A boron-containing resonant organic compound is provided. The structure of the boron-containing resonant organic compound is represented by the general formula (1):

[0007] [ka] is expressed as In general formula (1), R to R 19 are each independently a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, cyano, a substituted or unsubstituted C1 to C 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkynyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 10 aryloxy, substituted or unsubstituted arylamide, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C2-C 30 Heteroaryl, and substituted or unsubstituted C2-C 30 represents one of the boranyl groups, R1 to R 14 any two adjacent groups in the formula (I) can be linked to form a ring; R 18 and R 19can be linked to form a ring, M1 is a substituted or unsubstituted C6-C 30 and a substituted or unsubstituted 5- to 30-membered heteroaromatic ring, M2 represents an R-substituted or unsubstituted 6-membered ring; R is a deuterium atom, a tritium atom, a halogen atom, cyano, or a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkynyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 10 aryloxy, substituted or unsubstituted arylamide, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, and substituted or unsubstituted C2-C 30 represents one of the boranyl groups, The substitution mode of R is a single bond or a polycyclic bond; When M1 and M2 both represent a substituted or unsubstituted benzene ring, R1, R2, R3, R4, R5, R6, R7, R8, R 18 and R 19 do not all represent hydrogen atoms, X represents a carbon atom or a silicon atom; The substituents that can be substituted for the substitutable groups include deuterium atoms, tritium atoms, halogen atoms, cyano, C1-C 10 Alkyl, deuterium- or tritium-substituted C1-C 10 Alkyl, C3-C 10 Cycloalkyl, C6-C 30 Aryl, deuterium- or tritium-substituted C6-C 30 aryl, 5- to 30-membered heteroaryl, and deuterium- or tritium-substituted C2-C 30 and optionally selected from one or more of the heteroaryls Heteroatoms in heteroaryl and heteroaromatic rings are optionally selected from one or more of O, S, N, Si, and B.

[0008] The present invention further provides an organic light-emitting device having a substrate, a first electrode, a second electrode, and a functional layer in this order, wherein the functional layer is disposed between the first electrode and the second electrode, and the functional layer contains the boron-containing resonant organic compound according to the present invention.

[0009] The present invention further provides a material for an organic electroluminescent device, which comprises a boron-containing resonant organic compound according to the present invention.

[0010] The present invention further provides the use of the boron-containing resonant organic compound in an organic electroluminescent device.

[0011] The present invention further provides a display member comprising an organic light emitting device according to the present invention.

[0012] The present invention further provides a lighting device comprising an organic light emitting device according to the present invention.

[0013] The present invention further provides an electronic device carrying an organic light emitting device according to the present invention.

[0014] The present invention has the following significant technical advantages over the prior art: (1) When the compound of the present invention is used in an organic electroluminescent device, it can be used as a doping material for an emitting layer material, and can exhibit green fluorescence under the action of an electric field, and can be used in the field of organic electroluminescent lighting or organic electroluminescent display. (2) By incorporating a phosphorescent sensitizer, the compound of the present invention can be used as a doping material to effectively improve the life of the device. (3) The FWHM in the spectrum of the compound of the present invention is narrow, which can effectively improve the color gamut of the device.

[0015] The compounds of the present invention are characterized by a narrow full width at half maximum and can be used as green light doping materials in the light-emitting layer of organic electroluminescent devices, thereby improving the lifetime of the devices. [Brief explanation of the drawings]

[0016] [Figure 1] 1 is a diagram of the structure of materials used in an OLED device according to the present invention, where 1 is a transparent substrate layer, 2 is an anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is an emissive layer, 7 is a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, and 10 is a cathode layer. [Figure 2] FIG. 1 shows the PL spectrum of compound 36 according to the present invention in a toluene solution (1×10 −5 M). [Figure 3] FIG. 1 shows the PL spectrum of compound 48 according to the present invention in a toluene solution (1×10 −5 M). [Figure 4] FIG. 1 shows the PL spectrum of compound 64 according to the present invention in a toluene solution (1×10 −5 M). [Figure 5] FIG. 1 shows the PL spectrum of compound 533 according to the present invention in a toluene solution (1×10 −5 M). [Figure 6] FIG. 1 shows the hydrogen nuclear magnetic resonance spectrum of compound 36 according to the present invention. [Figure 7] FIG. 1 shows the hydrogen nuclear magnetic resonance spectrum of compound 48 according to the present invention. [Figure 8] FIG. 1 shows the hydrogen nuclear magnetic resonance spectrum of compound 64 according to the present invention. [Figure 9] FIG. 1 shows the hydrogen nuclear magnetic resonance spectrum of compound 533 according to the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0017] Hereinafter, the present invention will be specifically described with reference to the drawings and embodiments.

[0018] In the present invention, when describing electrodes, organic electroluminescent devices, and other structures, terms such as "top," "bottom," "upper," and "lower" used to indicate orientation simply indicate orientation in a specific state and do not mean that the related structure can only exist according to that orientation. Conversely, when the configuration of a structure changes, for example, when it is inverted, the orientation of the structure also changes accordingly. In particular, in the present invention, the "bottom" or "lower" side of an electrode is the side of the electrode that is closer to the substrate in the preparation process, and the opposite side that is away from the substrate is the "top" or "upper" side.

[0019] In the present invention, the terms "linked to form a ring" and "capable of linking to form a ring" mean that two groups may not be linked to each other or may be linked to each other to form a ring. Preferably, two groups are linked to form a ring by a C-C single bond, a C=C double bond, an O atom, a S atom, CQ1Q2, or NQ3, where Q1, Q2, and Q3 are each substituted or unsubstituted C1 to C 10 Alkyl, substituted or unsubstituted C6-C 30 or substituted or unsubstituted C2-C 30 Preferably, the two groups may be linked to form a substituted or unsubstituted 6- to 30-membered aromatic ring, a substituted or unsubstituted 5- to 30-membered heteroaromatic ring, or a substituted or unsubstituted 5- to 30-membered aliphatic ring.

[0020] In the present invention, the substituted or unsubstituted arylamide is

[0021] [ka] wherein Q4 and Q5 each represent a substituted or unsubstituted aromatic group, and Q4 and Q5 each preferably represent a substituted or unsubstituted C-C 30 or substituted or unsubstituted C2-C 30 represents a heteroaryl of the formula:

[0022] In the present invention, substituted or unsubstituted C6 to C 30 The aryl in the formula (I) is, but is not limited to, 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 fused tetraphenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted chrysenyl, substituted or unsubstituted diphenylphenyl, substituted or unsubstituted perylenyl, substituted or unsubstituted indenyl, combinations thereof, or fused ring combinations of the foregoing groups.

[0023] In the present invention, substituted or unsubstituted C2 to C 30 Heteroaryl, substituted or unsubstituted C5-C 30Heteroaryl, or substituted or unsubstituted 5- to 30-membered heteroaryl, is substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted oxadiazolyl, substituted or unsubstituted thiadiazolyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted benzofuryl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzimidazolyl, Examples of the substituted or unsubstituted alkyl radicals include, but are not limited to, substituted or unsubstituted aryl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridinyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, combinations thereof, or fused ring combinations of the foregoing groups.

[0024] C1 to C in the present invention 10 The alkyl (including straight chain alkyl and branched alkyl) is, but is not limited to, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, sec-butyl, neopentyl, n-pentyl, isopentyl, octyl, heptyl, n-decyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, or 1-butylpentyl.

[0025] C3 to C in the present invention 10The cycloalkyl in the above formula (I) is a monovalent, monocyclic, saturated hydrocarbon group having 3 to 10 carbon atoms as ring atoms. In this specification, C4 to C9 cycloalkyl is preferred, C5 to C8 cycloalkyl is more preferred, and C5 to C7 cycloalkyl is particularly preferred. Non-limiting examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl, and cycloheptyl.

[0026] The halogen atom in the present invention is a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0027] In the present invention, C1 to C10 alkoxy includes, but is not limited to, methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, or isopropoxy.

[0028] C2 to C in the present invention 10 Alkenyl includes, but is not limited to, ethenyl, 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, and the like.

[0029] C1 to C in the present invention 10 The alkynyl is preferably a C2-C8 alkynyl, more preferably a C2-C5 alkynyl, non-limiting examples of which include, but are not limited to, ethynyl, propynyl, n-butynyl, isobutynyl, n-pentynyl, isopentynyl, and neopentynyl.

[0030] The substituents for the group are arbitrarily selected from one or more of deuterium atoms, chlorine atoms, fluorine atoms, trifluoromethyl, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-pentyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, naphthyl, anthryl, phenanthryl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, benzoxazolyl group, benzothiazolyl, quinoxalinyl, quinolyl, isoquinolyl, furyl, thienyl, indolyl, pyrrolyl, dibenzofuryl, dibenzothienyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazolyl group, N-phenylcarbazolyl, carbazolinyl, and azaphenanthryl.

[0031] The present invention provides a boron-containing resonance organic compound, the structure of which is represented by the following general formula (1):

[0032] [ka] In general formula (1), R to R 19 are each independently a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, cyano, a substituted or unsubstituted C1 to C 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkynyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 10 aryloxy, substituted or unsubstituted arylamide, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C2-C 30 Heteroaryl, and substituted or unsubstituted C2-C 30 represents one of the boranyl groups, R1 to R 14 any two adjacent groups in the formula (I) can be linked to form a ring; R 18 and R19 can be linked to form a ring, M1 is a substituted or unsubstituted C6-C 30 and a substituted or unsubstituted 5- to 30-membered heteroaromatic ring, M2 represents an R-substituted or unsubstituted 6-membered ring; R is a deuterium atom, a tritium atom, a halogen atom, cyano, or a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkynyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 10 aryloxy, substituted or unsubstituted arylamide, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, and substituted or unsubstituted C2-C 30 represents one of the boranyl groups, The substitution mode of R is a single bond or a polycyclic bond; When M1 and M2 both represent a substituted or unsubstituted benzene ring, R1, R2, R3, R4, R5, R6, R7, R8, R 18 and R 19 do not all represent hydrogen atoms, X represents a carbon atom or a silicon atom; The substituents that can be substituted for the substitutable groups include deuterium atoms, tritium atoms, halogen atoms, cyano, C1-C 10 Alkyl, deuterium- or tritium-substituted C1-C 10 Alkyl, C3-C 10 Cycloalkyl, C6-C 30 Aryl, deuterium- or tritium-substituted C6-C 30 aryl, 5- to 30-membered heteroaryl, and deuterium- or tritium-substituted C2-C 30 and optionally selected from one or more of the heteroaryls Heteroatoms in heteroaryl and heteroaromatic rings are optionally selected from one or more of O, S, N, Si, and B.

[0033] In one solution, in general formula (1), R1 to R 19 are the same or different and are a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano, a substituted or unsubstituted C1 to C 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C1-C 10 aryloxy, substituted or unsubstituted arylamide, substituted or unsubstituted C6-C 30 and substituted or unsubstituted C2-C 30 represents one of the heteroaryls R1 to R 14 Any adjacent two of the following may be linked to form a ring: R 18 and R 19 can be linked to form a ring, M1 is a substituted or unsubstituted C6-C 30 or a substituted or unsubstituted 5- to 30-membered heteroaromatic ring, M2 represents a substituted or unsubstituted 6-membered ring; When M1 and M2 each represent a substituted or unsubstituted benzene ring, R1 to R8, R 18 and R 19 do not all represent hydrogen atoms, X represents C or Si; The substituents that replace the group include deuterium atoms, tritium atoms, halogen atoms, cyano, C1-C 10 Alkyl, deuterium- or tritium-substituted C1-C 10 Alkyl, C6-C 30 Aryl, deuterium- or tritium-substituted C6-C 30 Aryl, C5-C 30Heteroaryls of the formula (I) and deuterium- or tritium-substituted C2-C 30 and optionally selected from any one of the heteroaryls:

[0034] In a preferred solution, the structure of the boron-containing resonant organic compound is represented by the general formula (1-1) to the general formula (1-3):

[0035] [ka] It is represented by one of In the general formulas (1-1) to (1-3), R to R 25 are the same or different and are a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano, a substituted or unsubstituted C1 to C 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C1-C 10 aryloxy, substituted or unsubstituted arylamide, substituted or unsubstituted C6-C 30 and substituted or unsubstituted C2-C 30 represents one of the heteroaryls R1 to R 25 Any adjacent two of the following may be linked to form a ring: Ar3 are the same or different and are substituted or unsubstituted C1 to C 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C1-C 10 aryloxy, substituted or unsubstituted arylamide, substituted or unsubstituted C6-C 30 and substituted or unsubstituted C2-C 30 represents one of the heteroaryls X represents C or Si; In the general formula (1-1), R1 to R8, R18 , and R 19 do not all represent hydrogen atoms, The substituents for the group include deuterium, tritium, halogen atoms, cyano, C1-C 10 Alkyl, deuterium- or tritium-substituted C1-C 10 Alkyl, C6-C 30 Aryl, deuterium- or tritium-substituted C6-C 30 Aryl, C5-C 30 Heteroaryls of the formula (I) and deuterium- or tritium-substituted C2-C 30 and optionally selected from any one of the heteroaryls:

[0036] In a preferred solution, the structure of the boron-containing resonant organic compound is represented by the general formula (1-4) to the general formula (1-6):

[0037] [ka] It is represented by one of In the general formulas (1-4) to (1-6), R2, R7, R 10 , R 13 , R 16 , R 18 , R 21 and X have the same meaning as in claim 2; Ar3 is a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C1-C 10 aryloxy, substituted or unsubstituted arylamide, substituted or unsubstituted C6-C 30 and substituted or unsubstituted C2-C 30 represents one of the heteroaryls The substituents for the group include deuterium, tritium, halogen atoms, cyano, C1-C 10 Alkyl, deuterium- or tritium-substituted C1-C10 Alkyl, C6-C 30 Aryl, deuterium- or tritium-substituted C6-C 30 Aryl, C5-C 30 Heteroaryl, deuterium- or tritium-substituted C2-C 30 and optionally selected from any one of the heteroaryls:

[0038] In a preferred solution, the structure of the boron-containing resonant organic compound is represented by the general formula (1-7) to the general formula (1-12):

[0039] [ka] It is represented by one of In the general formulas (1-7) to (1-12), R may be the same or different and may be a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, cyano, a substituted or unsubstituted C1 to C6 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C1-C 10 aryloxy, substituted or unsubstituted arylamide, substituted or unsubstituted C6-C 30 and substituted or unsubstituted C2-C 30 represents one of the heteroaryls X represents C or Si; The substituents for the group, if necessary, include deuterium, tritium, halogen atoms, cyano, C1-C 10 Alkyl, deuterium- or tritium-substituted C1-C 10 Alkyl, C6-C 30 Aryl, deuterium- or tritium-substituted C6-C 30 Aryl, C5-C 30 Heteroaryl, deuterium- or tritium-substituted C2-C 30 and optionally selected from any one of the heteroaryls:

[0040] In the preferred solution, R and R1 to R 25 each independently represents a hydrogen atom, a deuterium atom, a tritium atom, a fluorine atom, cyano, adamantyl, methyl, deuterated methyl, tritiated methyl, trifluoromethyl, ethyl, deuterated ethyl, tritiated ethyl, isopropyl, deuterated isopropyl, tritiated butyl, tert-butyl, deuterated tert-butyl, tritiated tert-butyl, cyclopentyl, deuterated cyclopentyl, tritiated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, tritiated phenyl, diphenyl, deuterated diphenyl, tritiated diphenyl, triphenyl, deuterated triphenyl, tritiated triphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthryl, phenanthryl, pyridinyl, phenyl-substituted pyridinyl, quinolyl, furyl, thienyl, benzofuryl, phenyl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, tert-butyl-substituted dibenzofuryl, phenyl-substituted tert-butyl, xanthone, phenyl-substituted triazinyl, phenyl-substituted boranyl, methoxy, and tert-butoxy; Ar3 independently represents phenyl, deuterated phenyl, tritiated phenyl, diphenyl, deuterated diphenyl, tritiated diphenyl, triphenyl, deuterated triphenyl, tritiated triphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthryl, phenanthryl, pyridinyl, phenyl-substituted pyridinyl, quinolyl, furyl, thienyl, benzofuryl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl ether ... represents one of phenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuryl, phenyl-substituted tert-butyl, xanthone, phenyl-substituted triazinyl, phenyl-substituted boranyl, methoxy, and tert-butoxy; M1 represents one of phenyl, deuterated phenyl, diphenyl, deuterated diphenyl, triphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthryl, phenanthryl, pyridinyl, phenyl-substituted pyridinyl, quinolyl, 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 diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, and xanthone; M2 represents one of phenyl, deuterated phenyl, pyridinyl, phenyl-substituted pyridinyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, and tert-butyl-substituted phenyl; Substituents for the substitutable groups are optionally selected from one or more of deuterium, chlorine, fluorine, trifluoromethyl, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-pentyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, naphthyl, anthryl, phenanthryl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolyl, isoquinolyl, furyl, thienyl, indolyl, pyrrolyl, dibenzofuryl, dibenzothienyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazolyl, N-phenylcarbazolyl, carbazolinyl, and azaphenanthryl.

[0041] In the preferred solution, R and R1 to R 25 each independently represents a hydrogen atom, a cyano,

[0042] [ka] represents one of the following: Ar3 has the following structure:

[0043] [ka] represents one of the following: M1 is the following ring structure:

[0044] [ka] represents one of the following: M2 is the following ring structure:

[0045] [ka] represents Z is CR a represents R a are each independently a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, cyano, adamantyl, methyl, deuterated methyl, tritiated methyl, trifluoromethyl, ethyl, deuterated ethyl, tritiated ethyl, isopropyl, deuterated isopropyl, tritiated isopropyl, tert-butyl, deuterated tert-butyl, tritiated tert-butyl, cyclopentyl, deuterated cyclopentyl, tritiated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, tritiated phenyl, diphenyl, deuterated diphenyl, tritiated diphenyl, triphenyl, deuterated triphenyl, tritiated triphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthryl, phenanthryl, pyridinyl, phenyl-substituted pyridinyl, quinolyl, furyl, thienyl, benzofuryl, dibenzofuryl, dibenzothienyl, carbazolyl, N 6. The boron-containing resonant organic compound of claim 2, wherein the aryl group is one of phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuryl, phenyl-substituted tert-butyl, xanthone, phenyl-substituted triazinyl, phenyl-substituted boranyl, methoxy, and tert-butoxy.

[0046] In a preferred solution, the structure of the boron-containing resonant organic compound is represented by the general formula (A-1):

[0047] [ka] is expressed as In general formula (A-1), R to R 19 are each independently a hydrogen atom, a deuterium atom, a halogen atom, cyano, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkynyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted arylamide, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, and substituted or unsubstituted C2-C 30 represents one of the boranyl groups, R1 to R 19 any two adjacent groups in may be linked to form a ring; M1 is a substituted or unsubstituted C6-C 30 or a substituted or unsubstituted 5- to 30-membered heteroaromatic ring, M2 represents an R-substituted or unsubstituted 6-membered ring; R is a deuterium atom, a halogen atom, cyano, or a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkynyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted arylamide, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, and substituted or unsubstituted C2-C 30 represents one of the boranyl groups, The substitution mode of R is a single bond or a polycyclic bond; When M1 and M2 both represent a substituted or unsubstituted benzene ring, R1, R2, R3, R4, R5, R6, R7, R8, R 18 and R 19 do not all represent hydrogen atoms, The substituents that can be substituted for the substitutable groups include deuterium atoms, halogen atoms, cyano, C1-C 10 Alkyl, C3-C 10 Cycloalkyl, C6-C 30 and 5- to 30-membered heteroaryl, Heteroatoms in heteroaryl and heteroaromatic rings are optionally selected from one or more of O, S, N, Si, and B.

[0048] In a preferred solution, the structure of the boron-containing resonant organic compound is represented by the general formula (A-2):

[0049] [ka] is expressed as In general formula (A-2), R to R 23 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkynyl, substituted or unsubstituted C1-C 10 alkoxy, substituted or unsubstituted arylamide, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, and substituted or unsubstituted C2-C 30 represents any one of the following boranyls: R1 to R 23 any two adjacent groups in may be linked to form a ring; R1, R2, R3, R4, R5, R6, R7, R8, R 18 , and R 19 do not all represent hydrogen atoms, The substituents that can be substituted for the substitutable groups include deuterium atoms, halogen atoms, cyano, C1-C 10 Alkyl, C3-C 10 Cycloalkyl, C6-C 30 and 5- to 30-membered heteroaryl, The heteroatoms in the heteroaryl are optionally selected from one or more of O, S, N, Si, and B.

[0050] In a preferred solution, the structure of the boron-containing resonant organic compound is represented by the general formula (A-3):

[0051] [ka] is expressed as In general formula (A-3), R2, R7, R 10 , R 13 , R 16 and R 21 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1 to C 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkynyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted arylamide, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, and substituted or unsubstituted C2-C 30 represents one of the boranyl groups, R 18 is a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3-C 10Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkynyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted arylamide, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, and substituted or unsubstituted C2-C 30 represents one of the boranyl groups, The substituents that can be substituted for the substitutable groups include deuterium atoms, halogen atoms, cyano, C1-C 10 Alkyl, C3-C 10 Cycloalkyl, C6-C 30 and 5- to 30-membered heteroaryl, The heteroatoms in the heteroaryl are optionally selected from one or more of O, S, N, Si, and B.

[0052] In a preferred solution, M1 represents any one of the following substituted or unsubstituted groups: phenyl, naphthyl, anthryl, phenanthryl, pyridinyl, quinolyl, 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, and spirofluorenyl; M2 represents any one of the R-substituted or unsubstituted groups phenyl, naphthyl, anthryl, phenanthryl, pyridinyl, and quinolyl; R is a deuterium atom, a halogen atom, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridinyl, substituted or unsubstituted quinolyl, represents substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuryl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amido, or substituted or unsubstituted triazinyl; R1, R2, R3, R4, R5, R6, R7, R8, 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 , and R 23each independently represents a hydrogen atom, a deuterium atom, a halogen atom, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridinyl, substituted or unsubstituted cyclohex ... noryl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuryl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amido, or substituted or unsubstituted triazinyl; The substituents substituted on the group are arbitrarily selected from one or more of deuterium atoms, chlorine atoms, fluorine atoms, trifluoromethyl, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-pentyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, naphthyl, anthryl, phenanthryl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolyl, isoquinolyl, furyl, thienyl, indolyl, pyrrolyl, dibenzofuryl, dibenzothienyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazolyl, N-phenylcarbazolyl, carbazolinyl, and azaphenanthryl.

[0053] In a preferred solution, M1 has the following structure:

[0054] [ka] represents one of the following: M2 has the following structure:

[0055] [ka] represents one of the following: Z represents C—(H) or C—(R); R, R1, R2, R3, R4, R5, R6, R7, R8, 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 , and R 23 each independently represents a hydrogen atom, a deuterium atom, methyl, ethyl, isopropyl, tert-butyl, cyano, trifluoromethyl,

[0056] [ka] TIFF2025539594000018.tif124170 11. The boron-containing resonant organic compound of claim 1, 8, 9, or 10, wherein the compound is any one of:

[0057] In a preferred solution, M1 has the following structure:

[0058] [ka] represents one of the following: M2 has the following structure:

[0059] [ka] represents one of the following: Z represents C—(H) or C—(R); R, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 20 , R 21 , R 22 , and R 23 each independently represents a hydrogen atom, a deuterium atom, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl,

[0060] [ka] represents one of the following: R 18 and R 19 each independently represents a hydrogen atom, cyano, t-butyl,

[0061] [ka] TIFF2025539594000023.tif62170 represents one of the following: Ar3 has the following structure:

[0062] [ka] represents one of the following.

[0063] In a preferred solution, the specific structural formula of the boron-containing resonant organic compound is the following structure:

[0064] [ka] TIFF2025539594000026.tif230170 TIFF2025539594000027.tif255170 TIFF2025539594000028.tif226170 TIFF2025539594000029.tif243170 TIFF2025539594000030.tif249170 TIFF2025539594000031.tif229170 TIFF2025539594000032.tif252170 TIFF2025539594000033.tif255170 TIFF2025539594000034.tif233170 TIFF2025539594000035.tif231170 TIFF2025539594000036.tif229170 TIFF2025539594000037.tif238170 TIFF2025539594000038.tif252170 TIFF2025539594000039.tif222170 TIFF2025539594000040.tif226170 TIFF2025539594000041.tif241170 TIFF2025539594000042.tif243170 TIFF2025539594000043.tif242170 TIFF2025539594000044.tif242170 TIFF2025539594000045.tif244170 TIFF2025539594000046.tif245170 TIFF2025539594000047.tif245170 TIFF2025539594000048.tif243170 TIFF2025539594000049.tif245170 TIFF2025539594000050.tif246170 TIFF2025539594000051.tif247170 TIFF2025539594000052.tif236170 TIFF2025539594000053.tif255170 TIFF2025539594000054.tif255170 TIFF2025539594000055.tif255170 TIFF2025539594000056.tif229170 TIFF2025539594000057.tif247170 TIFF2025539594000058.tif228170 TIFF2025539594000059.tif217170 It is one of the following.

[0065] The present invention further provides an organic light-emitting device having a substrate, a first electrode, a second electrode, and a functional layer in this order, An organic light-emitting device is provided, wherein the functional layer is disposed between the first electrode and the second electrode, and the functional layer comprises the boron-containing resonant organic compound.

[0066] In a preferred solution, the functional layer comprises an emitting layer, the emitting layer comprising a host material and a doping material, the doping material being the boron-containing resonant organic compound.

[0067] In a preferred solution, the functional layer has an emitting layer, the emitting layer comprising a first host material, a second host material, and a doping material, wherein 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 resonant organic compound.

[0068] In a preferred solution, the functional layer has an emitting layer, which comprises a host material, an exciton-sensitized material, and a doping material, wherein the exciton-sensitized material is a complex containing a metal element, and the doping material is the boron-containing resonant organic compound.

[0069] The present invention further provides a material for an organic electroluminescent device, which comprises a boron-containing resonant organic compound according to the present invention.

[0070] The present invention further provides the use of the boron-containing resonant organic compound in an organic electroluminescent device.

[0071] In a preferred solution, the organic light-emitting functional layer has a light-emitting layer, and the light-emitting layer uses the boron-containing resonant organic compound of the present invention.

[0072] The present invention further provides a display member comprising an organic light emitting device according to the present invention.

[0073] The present invention further provides a lighting device comprising an organic light emitting device according to the present invention.

[0074] The present invention further provides an electronic device carrying an organic light emitting device according to the present invention.

[0075] The organic electroluminescent device in the present invention may be a bottom-emission organic electroluminescent device, a top-emission organic electroluminescent device, or a tandem organic electroluminescent device, but is not particularly limited thereto.

[0076] The organic electroluminescent device of the present invention comprises a substrate, a first electrode, an organic light-emitting functional layer, and a second electrode. The organic light-emitting functional layer comprises a hole transport region, a light-emitting layer, and an electron transport region. The hole transport region comprises a hole injection layer, a hole transport layer, and an electron blocking layer. The electron transport region comprises a hole blocking layer, an electron transport layer, and an electron injection layer. A CPL layer may also be provided on the second electrode.

[0077] The substrate of the organic electroluminescent device of the present invention may be any substrate commonly used in organic electroluminescent devices, including transparent substrates such as glass or transparent PI film substrates, and opaque substrates such as silicon substrates. Different substrates have different mechanical strength, thermal stability, transparency, surface smoothness, and waterproof properties. The direction in which the substrate is used varies depending on the different properties of the substrate. In the present invention, a transparent PI film substrate is preferably used. The thickness of the substrate is not particularly limited.

[0078] The first electrode is formed on the substrate. The first electrode and the second electrode may face each other. The first electrode may be an anode. The first electrode may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. If the first electrode is a transmissive electrode, it may 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). If the first electrode is a semi-transmissive or reflective electrode, it may contain Ag, Mg, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, or other metals, an alloy of several metals, or a combination of metals, metal oxides, and metal alloys. The thickness of the first electrode depends on the material used, but is typically 50 to 500 nm, preferably 70 to 300 nm, and more preferably 100 to 200 nm.

[0079] The organic functional material layer disposed between the first electrode and the second electrode has, from bottom to top, a hole transport region, a light emitting layer, and an electron transport region.

[0080] In the present invention, the hole transport region of the organic electroluminescent device includes a hole injection layer, a hole transport layer, an electron blocking layer, and the like.

[0081] The materials for the hole injection layer, hole transport layer, and electron blocking layer may be selected from any materials used in conventional organic electroluminescent devices.

[0082] The hole injection layer contains a host organic material capable of conducting holes, as well as a P-type doping material with a deep HOMO energy level (with a corresponding extremely deep LUMO energy level). Experimental studies have shown that, to facilitate hole injection from the anode into the organic film layer, as long as the HOMO energy level of the host organic material used in the buffer layer at the anode interface for hole conduction matches the HOMO energy level of the P-type doping material, a charge transfer state can be created between the host material and the doping material, an ohmic contact can be formed between the buffer layer and the anode, and effective hole injection from the electrode into the hole injection conduction layer can be achieved.

[0083] Considering the above empirical summary, different P-type doping materials are required to match hole-host organic materials with different HOMO energy levels, so that ohmic contacts can be formed at the interface and the hole injection effect can be improved.

[0084] In an embodiment of the present invention, the hole injection layer comprises a charge-conducting P-type doping material selected from, but not limited to, a quinone derivative such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ); or a hexaazatriphenylene derivative such as 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CN); or a cyclopropane derivative such as 2-(7-dicyanomethylene-1,3,4,5,6,8,9,10-octafluoro-7H-pyren-2-ylidene)-malononitrile; or a metal oxide such as tungsten oxide and molybdenum oxide.

[0085] In the hole injection layer of the present invention, the mass ratio of the hole transport material to the P-type doping material is 99:1 to 95:5, and preferably 99:1 to 97:3.

[0086] The thickness of the hole injection layer of the present invention is 5 nm to 100 nm, preferably 5 nm to 50 nm, and more preferably 5 nm to 20 nm, but the thickness is not limited to this range.

[0087] Preferably, the material of the hole transport layer of the present invention may be selected from any of the following compounds disclosed in the prior art:

[0088] [ka] The material of the hole transport layer and the host organic material in the hole injection layer of the present invention are preferably selected from the same compounds.

[0089] The thickness of the hole transport layer of the present invention is 5 nm to 200 nm, preferably 10 nm to 150 nm, and more preferably 20 nm to 100 nm, but is not limited to this range.

[0090] In an embodiment of the present invention, the material of the electron blocking layer of the present invention may be selected from any of the following compounds shown in the prior art:

[0091] [ka] The thickness of the electron blocking layer of the present invention is 1 nm to 50 nm, preferably 5 nm to 40 nm, but is not limited to this range.

[0092] After the hole injection layer, hole transport layer, and electron blocking layer are formed, a corresponding light-emitting layer is formed on the electron blocking layer.

[0093] The light-emitting layer may include a host material and a doping material. The host material may be a green light-emitting host material commonly used in the technical field. The doping material may be a boron-containing resonant organic compound represented by general formula (1) of the present invention.

[0094] The light-emitting layer may include a single host material or dual host materials.

[0095] The dual host material includes a first host material and a second host material, and preferably, at least one of the first host material and the second host material is a TADF material.

[0096] TADF materials are thermally activated delayed fluorescent materials characterized by a small energy gap between the first excited singlet state and the first excited triplet state. In this case, both the generated singlet and triplet excitons can be used in the device, and the utilization rate of excitons generated by excitation within the device can be as close to 100% as possible. Compared to conventional fluorescent materials, TADF materials have a higher exciton utilization rate.

[0097] The light-emitting layer may include a host material, an exciton-sensitized material, and a doping material.

[0098] An exciton-sensitized material is a material in which the light-emitting material in the light-emitting layer can fully utilize excitons, and the light-emitting layer exhibits the emission spectrum of the sensitized material. The exciton sensitizer may provide functions such as exciton capture, exciton conversion, and exciton transfer in an electroluminescent device. The combination of the boron-containing resonant organic compound represented by general formula (1) of the present invention with an exciton-sensitized material significantly improves device efficiency and solves problems such as exciton quenching and efficiency loss in the device.

[0099] In the light-emitting layer of the present invention, the mass ratio of the host material to the doping material is 99:1 to 70:30, preferably 99:1 to 85:15, and more preferably 97:3 to 87:13.

[0100] The thickness of the light-emitting layer may be adjusted to optimize the light-emitting efficiency and driving voltage. The thickness is preferably in the range of 5 nm to 50 nm, more preferably 10 nm to 50 nm, and even more preferably 15 nm to 40 nm, but is not limited to these ranges.

[0101] In the present invention, the electron transport region may have, from bottom to top, a hole blocking layer, an electron transport layer, and an electron injection layer provided on the light emitting layer in this order, but is not limited thereto.

[0102] The hole blocking layer is a layer that blocks holes injected from the anode and passing through the light-emitting layer to the cathode, thereby enabling the device to have a longer life and improve the device efficiency. The hole blocking layer of the present invention may be provided on the light-emitting layer. The material of the hole blocking layer of the organic electroluminescent device of the present invention can be a conventional compound having a hole blocking function, such as:

[0103] [ka] There is.

[0104] The thickness of the hole blocking layer of the present invention is 2 nm to 200 nm, preferably 5 nm to 150 nm, and more preferably 5 nm to 50 nm, but is not limited to this range.

[0105] The electron transport layer may be provided on the light-emitting layer or on the hole-blocking layer (if present). The material of the electron transport layer is a material that can easily accept electrons from the cathode and transfer the accepted electrons to the light-emitting layer. A material with high electron mobility is preferred. The electron transport layer of the organic electroluminescent device of the present invention may be made of any material disclosed in the prior art for the electron transport layer of an organic electroluminescent device, for example:

[0106] [ka] may be.

[0107] In a preferred embodiment of the present invention, the electron transport layer may further comprise another conventional compound for electron transport layers, such as Alq3 or LiQ, preferably LiQ.

[0108] The thickness of the electron transport layer of the present invention is 10 nm to 80 nm, preferably 20 nm to 60 nm, and more preferably 25 nm to 45 nm, but is not limited to this range.

[0109] An electron injection layer may be provided on the electron transport layer. Generally, the material of the electron injection layer preferably has a low work function so as to facilitate electron injection into the organic functional material layer. The electron injection layer of the organic electroluminescent device of the present invention may be made of any of the materials disclosed in the prior art for use in the electron injection layer of organic electroluminescent devices, such as LiF, Cs2CO3, CsF, Csq, NaF, MgF2, CaF2, Al2O3, and Yb.

[0110] The thickness of the electron injection layer of the present invention is 0.1 nm to 5 nm, preferably 0.5 nm to 3 nm, and more preferably 0.8 nm to 1.5 nm, but is not limited to this range.

[0111] A second electrode may be provided on the electron transport region. The second electrode may be a cathode. The second electrode may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. If the second electrode is a transmissive electrode, it may include, for example, Li, Yb, Ca, LiF / Ca, LiF / Al, Al, Mg, BaF2, Ba, Ag, or a compound or mixture thereof. If the second electrode is a semi-transmissive or reflective electrode, it may include, but is not limited to, Ag, Mg, Yb, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, or a compound or mixture thereof. The thickness of the cathode depends on the material used.

[0112] The organic electroluminescent device of the present invention may further have a packaging structure. The packaging structure may be a protective structure that prevents 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 film that covers the entire surface of the organic layer.

[0113] The method for preparing an organic electroluminescent device of the present invention includes sequentially stacking 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, a cathode, and an optional coating layer on a substrate. This method may include, but is not limited to, vacuum deposition, vacuum evaporation, spin coating, casting, LB printing, inkjet printing, laser printing, LITI, or other methods. In the present invention, each layer is preferably formed using a vacuum evaporation method. The processing conditions for the vacuum evaporation method may generally be selected by those skilled in the art according to actual requirements.

[0114] Preparation of compounds Example 1: Synthesis of Compound 5:

[0115] [ka] Synthesis of intermediate M1: A three-neck flask was charged with starting material A1 (11 mmol, 2.99 g) and starting material B1 (10 mmol, 2.04 g) and dissolved in a mixed solvent (70 mL toluene, 35 mL ethanol). Pd(PPh3)4 (0.10 mmol, 0.12 g) and 15 mL of 3 mol / L aqueous K2CO3 were then added. The mixture was heated to reflux under nitrogen protection and reacted for 12 hours. A sample of the reaction mixture was taken and spotted on a plate to confirm completion of the reaction. After cooling to room temperature, the reaction mixture was filtered through a pad of diatomaceous earth and washed with chloroform. The filtrate was evaporated under vacuum. The residue was purified by silica gel column chromatography using hexane / toluene as the eluent to obtain intermediate M1.

[0116] Synthesis of intermediate N1: Intermediate M1 (18.4 mmol, 4.95 g) and cesium carbonate (55.2 mmol, 18.0 g) were placed in a two-neck flask, and 120 mL of anhydrous DMF was added under nitrogen protection. The mixture was stirred at room temperature for 30 minutes. Starting material C1 (40.5 mmol, 11.32 g) was added under nitrogen protection. The solution was refluxed under magnetic stirring for 24 hours, then cooled, filtered, washed, dried, and subjected to column chromatography to obtain intermediate N1.

[0117] Synthesis of intermediate J1: Dissolve intermediate N1 (5.1 mmol, 4.02 g) in 50 mL of tetrahydrofuran (THF). Solution 2.3 of n-butyllithium (2.5 M, 5.7 mmol) in n-hexane. mL of starting material D1 is slowly added at -78°C under nitrogen. The mixture is stirred at -78°C for 2 hours. Next, 15 mL of a solution of starting material D1 (5.5 mmol, 1.0 g) in tetrahydrofuran is slowly added. The reaction mixture is then slowly warmed to room temperature and stirred overnight. To the reaction mixture, 20 mL of dilute hydrochloric acid (1 M), distilled water, and ethyl acetate are added. The aqueous layer is separated and extracted three times with ethyl acetate. The organic layers are combined, dried over sodium sulfate, and filtered. The solvent is removed under reduced pressure. The crude product is then dissolved in anhydrous dichloromethane. Next, 47% boron trifluoride-diethyl ether is slowly added. The reaction mixture is stirred overnight and then slowly quenched with aqueous NaHCO3 solution. The aqueous layer is then separated, extracted with dichloromethane, dried over sodium sulfate, filtered, concentrated by rotary evaporation, and subjected to column chromatography to obtain intermediate J1.

[0118] Synthesis of intermediate K1: Intermediate J1 (20.0 mmol, 17.42 g) and 200 mL of glacial acetic acid are added successively to a three-neck flask under nitrogen protection. The mixture is cooled to 0 °C in a cryogenic bath and protected from light. NBS (25 mmol, 4.45 g) is added in batches. The mixture is stirred at 0 °C for 11 h. The reaction solution is concentrated and purified by silica gel column chromatography to obtain intermediate K1.

[0119] Synthesis of compound 5: Intermediate K1 (10 mmol, 9.50 g) and 90 mL of o-dichlorobenzene are added to a sealed pressure tube under nitrogen protection. A 2.5 M solution of n-butyllithium in n-hexane (30 mmol, 12 mL) is added at -78 °C. The system is heated to 60 °C and reacted for 2 hours. Next, boron tribromide (15 mmol, 1.5 mL) is added at 0 °C. The system is then transferred to room temperature and reacted for another 5 hours. Next, N,N-diisopropylethylamine (20 mmol, 3.5 mL) is added to the system at 0 °C, and the system is heated to 200 °C and reacted for 12 hours. After the reaction, the organic layer is concentrated under reduced pressure and purified by silica gel column chromatography to obtain compound 5. A toluene solution (1 × 10-5 The full width at half maximum at M) is 26 nm.

[0120] Example 2: Synthesis of Compound 36:

[0121] [ka] Synthesis of intermediate M2: A three-neck flask was charged with starting material A1 (11 mmol, 2.99 g) and starting material B2 (10 mmol, 3.16 g) and dissolved in a mixed solvent (70 mL of toluene and 35 mL of ethanol). Pd(PPh3)4 (0.10 mmol, 0.12 g) and 15 mL of 3 mol / L aqueous K2CO3 were then added. The mixture was heated to reflux under nitrogen protection and reacted for 14 hours. A sample of the reaction mixture was taken and spotted on a plate to confirm completion of the reaction. After cooling to room temperature, the reaction mixture was filtered through a pad of diatomaceous earth and washed with chloroform. The filtrate was evaporated under vacuum. The residue was purified by silica gel column chromatography using hexane / toluene as the eluent to obtain intermediate M2.

[0122] Synthesis of intermediate N2: Add intermediate M2 (18.4 mmol, 7.02 g) and cesium carbonate (55.2 mmol, 18.0 g) to a two-neck flask and add 120 mL of anhydrous DMF under nitrogen protection. Stir the mixture at room temperature for 35 minutes. Add starting material C1 (40.5 mmol, 11.32 g) under nitrogen protection. Reflux the solution under magnetic stirring for 20 hours, then cool, filter, wash, dry, and subject to column chromatography to obtain intermediate N2.

[0123] Synthesis of intermediate J2: Dissolve intermediate N2 (5.1 mmol, 4.59 g) in 50 mL of tetrahydrofuran (THF). Solution 2.3 of n-butyllithium (2.5 M, 5.7 mmol) in n-hexane. mL of starting material D1 is slowly added at -78°C under nitrogen. The mixture is stirred at -78°C for 3 hours. Next, 15 mL of a solution of starting material D1 (5.5 mmol, 1.0 g) in tetrahydrofuran is slowly added. The reaction mixture is then slowly warmed to room temperature and stirred overnight. To the reaction mixture, 20 mL of dilute hydrochloric acid (1 M), distilled water, and ethyl acetate are added. The aqueous layer is separated and extracted three times with ethyl acetate. The organic layers are combined, dried over sodium sulfate, and filtered. The solvent is removed under reduced pressure. The crude product is then dissolved in anhydrous dichloromethane. Next, 47% boron trifluoride-diethyl ether is slowly added. The reaction mixture is stirred overnight and then slowly quenched with aqueous NaHCO3. The aqueous layer is then separated, extracted with dichloromethane, dried over sodium sulfate, filtered, concentrated by rotary evaporation, and subjected to column chromatography to obtain intermediate J2.

[0124] Synthesis of intermediate K2: To a three-neck flask, intermediate J2 (20.0 mmol, 19.67 g) and 200 mL of glacial acetic acid are added successively under nitrogen protection. The mixture is cooled to 0 °C in a cryogenic bath and protected from light. NBS (25 mmol, 4.45 g) is added in batches. The mixture is stirred at 0 °C for 12 h. The reaction solution is concentrated and purified by silica gel column chromatography to obtain intermediate K2.

[0125] Synthesis of compound 36: Intermediate K2 (10 mmol, 10.6 g) and 90 mL of o-dichlorobenzene are placed in a sealed pressure tube under nitrogen protection. A 2.5 M solution of n-butyllithium in n-hexane (30 mmol, 12 mL) is added at -78 °C. The system is heated to 60 °C and reacted for 3 hours. Next, boron tribromide (15 mmol, 1.5 mL) is added at 0 °C. The system is then transferred to room temperature and reacted for another 6 hours. Next, N,N-diisopropylethylamine (20 mmol, 3.5 mL) is added to the system at 0 °C, and the system is then heated to 200 °C and reacted for 11 hours. After the reaction, the organic layer is concentrated under reduced pressure and purified by silica gel column chromatography to obtain compound 36. A toluene solution (1 × 10-5 M) is 28 nm.

[0126] Example 3: Synthesis of Compound 119:

[0127] [ka] Synthesis of intermediate M3: A three-neck flask was charged with starting material A1 (11 mmol, 2.99 g) and starting material B3 (10 mmol, 3.3 g) and dissolved in a mixed solvent (70 mL toluene, 35 mL ethanol). Pd(PPh3)4 (0.10 mmol, 0.12 g) and 15 mL of 3 mol / L aqueous K2CO3 solution were then added. The mixture was heated to reflux under nitrogen protection and reacted for 12 hours. A sample of the reaction mixture was taken and spotted on a plate to confirm completion of the reaction. After cooling to room temperature, the reaction mixture was filtered through a pad of diatomaceous earth and washed with chloroform. The filtrate was evaporated under vacuum. The residue was purified by silica gel column chromatography using hexane / toluene as the eluent to obtain intermediate M3.

[0128] Synthesis of intermediate N3: Add intermediate M3 (18.4 mmol, 7.27 g) and cesium carbonate (55.2 mmol, 18.0 g) to a two-neck flask and add 120 mL of anhydrous DMF under nitrogen protection. Stir the mixture at room temperature for 35 minutes. Add starting material C1 (40.5 mmol, 11.32 g) under nitrogen protection. Reflux the solution under magnetic stirring for 23 hours, then cool, filter, wash, dry, and subject to column chromatography to obtain intermediate N3.

[0129] Synthesis of intermediate J3: Dissolve intermediate N3 (5.1 mmol, 4.66 g) in 60 mL of tetrahydrofuran (THF). Solution 2.3 of n-butyllithium (2.5 M, 5.7 mmol) in n-hexane. mL of starting material D1 is slowly added at -78°C under nitrogen. The mixture is stirred at -78°C for 2.5 hours. Next, 15 mL of a solution of starting material D1 (5.5 mmol, 1.0 g) in tetrahydrofuran is slowly added. The reaction mixture is then slowly warmed to room temperature and stirred overnight. To the reaction mixture, 20 mL of dilute hydrochloric acid (1 M), distilled water, and ethyl acetate are added. The aqueous layer is separated and extracted three times with ethyl acetate. The organic layers are combined, dried over sodium sulfate, and filtered. The solvent is removed under reduced pressure. The crude product is then dissolved in anhydrous dichloromethane. Next, 47% boron trifluoride-diethyl ether is slowly added. The reaction mixture is stirred overnight and then slowly quenched with aqueous NaHCO3 solution. The aqueous layer is then separated, extracted with dichloromethane, dried over sodium sulfate, filtered, concentrated by rotary evaporation, and subjected to column chromatography to obtain intermediate J3.

[0130] Synthesis of intermediate K3: To a three-neck flask, intermediate J3 (20.0 mmol, 19.95 g) and 220 mL of glacial acetic acid are added successively under nitrogen protection. The mixture is cooled to 0 °C in a cryogenic bath and protected from light. NBS (25 mmol, 4.45 g) is added in batches. The mixture is stirred at 0 °C for 12 h. The reaction solution is concentrated and purified by silica gel column chromatography to obtain intermediate K3.

[0131] Synthesis of compound 119: Intermediate K3 (10 mmol, 10.76 g) and 120 mL of o-dichlorobenzene are placed in a sealed pressure tube under nitrogen protection. A 2.5 M solution of n-butyllithium in n-hexane (30 mmol, 12 mL) is added at -78 °C. The system is heated to 60 °C and reacted for 3 hours. Next, boron tribromide (15 mmol, 1.5 mL) is added at 0 °C. The system is then transferred to room temperature and reacted for another 6 hours. Next, N,N-diisopropylethylamine (20 mmol, 3.5 mL) is added to the system at 0 °C, and the system is then heated to 200 °C and reacted for 13 hours. After the reaction, the organic layer is concentrated under reduced pressure and purified by silica gel column chromatography to obtain compound 119. A toluene solution (1 × 10 -5 The full width at half maximum (FWHM) is 27 nm.

[0132] Example 4: Synthesis of Compound 149:

[0133] [ka] Synthesis of intermediate Y1: A three-neck flask was charged with raw material E1 (2.50 mmol, 0.85 g), B2pin2 (2.75 mmol, 0.70 g), PdCl2(dppf) (0.12 mmol, 0.09 g), AcOK (6.55 mmol, 0.64 g), and 1,4-dioxane (10 mL) and heated to reflux at 110 °C for 2 h under a nitrogen atmosphere. After cooling to room temperature, the reaction mixture was filtered through a pad of diatomaceous earth and washed with chloroform. The filtrate was evaporated under vacuum. The residue was purified by silica gel column chromatography using hexane / ethyl acetate as the eluent to obtain intermediate Y1.

[0134] Synthesis of intermediate M4: A three-neck flask was charged with raw material A1 (11 mmol, 2.99 g) and intermediate Y1 (10 mmol, 3.86 g) and dissolved in a mixed solvent (70 mL toluene, 35 mL ethanol). Pd(PPh3)4 (0.10 mmol, 0.12 g) and 15 mL of 3 mol / L aqueous K2CO3 solution were then added. The mixture was heated to reflux under nitrogen protection and reacted for 15 hours. A sample of the reaction mixture was taken and spotted on a plate to confirm completion of the reaction. After cooling to room temperature, the reaction mixture was filtered through a pad of diatomaceous earth and washed with chloroform. The filtrate was evaporated under vacuum. The residue was purified by silica gel column chromatography using hexane / toluene as the eluent to obtain intermediate M4.

[0135] Synthesis of intermediate N4: Add intermediate M4 (18.4 mmol, 8.3 g) and cesium carbonate (55.2 mmol, 18.0 g) to a two-neck flask and add 120 mL of anhydrous DMF under nitrogen protection. Stir the mixture at room temperature for 40 minutes. Add starting material C1 (40.5 mmol, 11.3 g) under nitrogen protection. Reflux the solution under magnetic stirring for 21 hours, then cool, filter, wash, dry, and subject to column chromatography to obtain intermediate N4.

[0136] Synthesis of intermediate J4: Dissolve intermediate N4 (5.1 mmol, 4.95 g) in 50 mL of tetrahydrofuran (THF). Solution 2.3 of n-butyllithium (2.5 M, 5.7 mmol) in n-hexane. mL of starting material D1 is slowly added at -78°C under nitrogen. The mixture is stirred at -78°C for 2.5 hours. Next, 15 mL of a solution of starting material D1 (5.5 mmol, 1.0 g) in tetrahydrofuran is slowly added. The reaction mixture is then slowly warmed to room temperature and stirred overnight. 20 mL of dilute hydrochloric acid (1 M) solution, distilled water, and ethyl acetate are added to the reaction mixture. The aqueous layer is separated and extracted three times with ethyl acetate. The organic layers are combined, dried over sodium sulfate, and filtered. The solvent is removed under reduced pressure. The crude product is then dissolved in anhydrous dichloromethane. 47% boron trifluoride-diethyl ether is then slowly added. The reaction mixture is stirred overnight and then slowly quenched with aqueous NaHCO3 solution. The aqueous layer is then separated, extracted with dichloromethane, dried over sodium sulfate, filtered, concentrated by rotary evaporation, and subjected to column chromatography to obtain intermediate J4.

[0137] Synthesis of intermediate K4: To a three-neck flask, intermediate J4 (20.0 mmol, 21.07 g) and 230 mL of glacial acetic acid are added successively under nitrogen protection. The mixture is cooled to 0 °C in a cryostat and protected from light. NBS (25 mmol, 4.45 g) is added in batches. The mixture is stirred at 0 °C overnight. The reaction mixture is concentrated and purified by silica gel column chromatography to give intermediate K4.

[0138] Synthesis of compound 149: Intermediate K4 (10 mmol, 11.32 g) and 120 mL of o-dichlorobenzene are placed in a sealed pressure tube under nitrogen protection. At -78°C, a 2.5 M solution of n-butyllithium in n-hexane (30 mmol, 12 mL) is added. The system is heated to 60°C and reacted for 3.5 hours. Next, boron tribromide (15 mmol, 1.5 mL) is added at 0°C. The system is then transferred to room temperature and reacted for another 7 hours. Next, N,N-diisopropylethylamine (20 mmol, 3.5 mL) is added to the system at 0°C, and the system is then heated to 200°C and reacted for 12 hours. After the reaction, the organic layer is concentrated under reduced pressure and purified by silica gel column chromatography to obtain compound 149. A toluene solution (1 x 10 -5 M) is 29 nm.

[0139] Example 5: Synthesis of Compound 165:

[0140] [ka] Synthesis of intermediate M5: A three-neck flask was charged with starting material A1 (11 mmol, 2.99 g) and starting material B5 (10 mmol, 3.3 g) and dissolved in a mixed solvent (70 mL toluene, 35 mL ethanol). Pd(PPh3)4 (0.10 mmol, 0.12 g) and 15 mL of 3 mol / L aqueous K2CO3 solution were then added. The mixture was heated to reflux under nitrogen protection and reacted for 12.5 hours. A sample of the reaction mixture was taken and spotted on a plate to confirm completion of the reaction. After cooling the reaction mixture to room temperature, the reaction mixture was filtered through a pad of diatomaceous earth and washed with chloroform. The filtrate was evaporated under vacuum. The residue was purified by silica gel column chromatography using hexane / toluene as the eluent to obtain intermediate M5.

[0141] Synthesis of intermediate N5: Intermediate M5 (18.4 mmol, 7.27 g) and cesium carbonate (55.2 mmol, 18.0 g) were added to a two-neck flask, and 120 mL of anhydrous DMF was added under nitrogen protection. The mixture was stirred at room temperature for 35 minutes. Starting material C1 (40.5 mmol, 11.32 g) was added under nitrogen protection. The solution was refluxed under magnetic stirring for 22 hours, then cooled, filtered, washed, dried, and subjected to column chromatography to obtain intermediate N5.

[0142] Synthesis of Intermediate J5: Intermediate N5 (5.1 mmol, 4.66 g) is dissolved in 50 mL of tetrahydrofuran (THF). 2.3 mL of a solution of n-butyllithium (2.5 M, 5.7 mmol) in n-hexane is slowly added at −78°C under nitrogen. The mixture is stirred at −78°C for 2.5 hours. 15 mL of a solution of starting material D1 (5.5 mmol, 1.0 g) in tetrahydrofuran is slowly added. The reaction mixture is then slowly warmed to room temperature and stirred overnight. 20 mL of a dilute hydrochloric acid (1 M) solution, distilled water, and ethyl acetate are added to the reaction mixture. The aqueous layer is separated and extracted three times with ethyl acetate. The organic layers are combined, dried over sodium sulfate, and filtered. The solvent is removed under reduced pressure. The crude product is then dissolved in anhydrous dichloromethane. 47% boron trifluoride in diethyl ether is then slowly added. The reaction mixture is stirred overnight and then slowly quenched with aqueous NaHCO solution. The aqueous layer is then separated, extracted with dichloromethane, dried over sodium sulfate, filtered, concentrated by rotary evaporation, and subjected to column chromatography to give intermediate J5.

[0143] Synthesis of intermediate K5: To a three-neck flask, intermediate J5 (20.0 mmol, 19.95 g) and 220 mL of glacial acetic acid are added successively under nitrogen protection. The mixture is cooled to 0 °C in a cryogenic bath and protected from light. NBS (25 mmol, 4.45 g) is added in batches. The mixture is stirred at 0 °C for 12.5 h. The reaction solution is concentrated and purified by silica gel column chromatography to obtain intermediate K5.

[0144] Synthesis of compound 165: Intermediate K5 (10 mmol, 10.76 g) and 120 mL of o-dichlorobenzene are placed in a sealed pressure tube under nitrogen protection. A 2.5 M solution of n-butyllithium (30 mmol, 12 mL) in n-hexane is added at -78°C. The system is heated to 60°C and reacted for 2 hours. Next, boron tribromide (15 mmol, 1.5 mL) is added at 0°C. The system is then transferred to room temperature and reacted for an additional 5.5 hours. Next, N,N-diisopropylethylamine (20 mmol, 3.5 mL) is added to the system at 0°C, and the system is then heated to 200°C and reacted for 12 hours. After the reaction, the organic layer is concentrated under reduced pressure and purified by silica gel column chromatography to obtain compound 165. A toluene solution (1 x 10 -5 M) is 27 nm.

[0145] Example 6: Synthesis of Compound 208:

[0146] [ka] Synthesis of intermediate M6: A three-neck flask was charged with starting material A1 (11 mmol, 2.99 g) and starting material B6 (10 mmol, 3.14 g) and dissolved in a mixed solvent (70 mL toluene, 35 mL ethanol). Pd(PPh3)4 (0.10 mmol, 0.12 g) and 15 mL of 3 mol / L aqueous K2CO3 solution were then added. The mixture was heated to reflux under nitrogen protection and reacted for 12 hours. A sample of the reaction mixture was taken and spotted on a plate to confirm completion of the reaction. After cooling to room temperature, the reaction mixture was filtered through a pad of diatomaceous earth and washed with chloroform. The filtrate was evaporated under vacuum. The residue was purified by silica gel column chromatography using hexane / toluene as the eluent to obtain intermediate M6.

[0147] Synthesis of intermediate N6: Intermediate M6 (18.4 mmol, 6.98 g) and cesium carbonate (55.2 mmol, 18.0 g) were placed in a two-neck flask, and 120 mL of anhydrous DMF was added under nitrogen protection. The mixture was stirred at room temperature for 25 minutes. Starting material C1 (40.5 mmol, 11.32 g) was added under nitrogen protection. The solution was refluxed under magnetic stirring for 20 hours, then cooled, filtered, washed, dried, and subjected to column chromatography to obtain intermediate N6.

[0148] Synthesis of intermediate J6: Dissolve intermediate N6 (5.1 mmol, 4.58 g) in 50 mL of tetrahydrofuran (THF). Solution 2.3 of n-butyllithium (2.5 M, 5.7 mmol) in n-hexane. mL of starting material D1 is slowly added at -78°C under nitrogen. The mixture is stirred at -78°C for 1.5 hours. Next, 15 mL of a solution of starting material D1 (5.5 mmol, 1.0 g) in tetrahydrofuran is slowly added. The reaction mixture is then slowly warmed to room temperature and stirred overnight. 20 mL of dilute hydrochloric acid (1 M) solution, distilled water, and ethyl acetate are added to the reaction mixture. The aqueous layer is separated and extracted three times with ethyl acetate. The organic layers are combined, dried over sodium sulfate, and filtered. The solvent is removed under reduced pressure. The crude product is then dissolved in anhydrous dichloromethane. 47% boron trifluoride-diethyl ether is then slowly added. The reaction mixture is stirred overnight and then slowly quenched with aqueous NaHCO3 solution. The aqueous layer is then separated, extracted with dichloromethane, dried over sodium sulfate, filtered, concentrated by rotary evaporation, and subjected to column chromatography to obtain intermediate J6.

[0149] Synthesis of intermediate K6: To a three-neck flask, intermediate J6 (20.0 mmol, 19.63 g) and 220 mL of glacial acetic acid are added successively under nitrogen protection. The mixture is cooled to 0 °C in a cryogenic bath and protected from light. NBS (25 mmol, 4.45 g) is added in batches. The mixture is stirred at 0 °C for 11.5 h. The reaction mixture is concentrated and purified by silica gel column chromatography to give intermediate K6.

[0150] Synthesis of compound 208: Intermediate K6 (10 mmol, 10.6 g) and 120 mL of o-dichlorobenzene are added to a sealed pressure tube under nitrogen protection. A 2.5 M solution of n-butyllithium in n-hexane (30 mmol, 12 mL) is added at -78 °C. The system is heated to 60 °C and reacted for 2 hours. Next, boron tribromide (15 mmol, 1.5 mL) is added at 0 °C. The system is then transferred to room temperature and reacted for an additional 5.5 hours. Next, N,N-diisopropylethylamine (20 mmol, 3.5 mL) is added to the system at 0 °C, and the system is then heated to 200 °C and reacted for 12 hours. After the reaction, the organic layer is concentrated under reduced pressure and purified by silica gel column chromatography to obtain compound 208. A toluene solution (1 × 10 -5 The full width at half maximum (FWHM) is 28 nm.

[0151] Example 7 Synthesis of Compound 255:

[0152] [ka] Synthesis of intermediate B1: Add raw material E1 (1.68 g, 5 mmol) and cesium carbonate (4.07 g, 12.5 mmol) to a two-neck flask, and add 50 mL of anhydrous DMF under nitrogen protection. Stir the mixture at room temperature for 30 minutes. Add raw material C1 (1.4 g, 5 mmol) under nitrogen protection. Stir the mixture at 140 °C for 12 hours under nitrogen protection, then filter, wash, dry, and subject to column chromatography (PE:EA = 20:1) to obtain intermediate B1.

[0153] Synthesis of Intermediate C1: Intermediate B1 (3.03 g, 5.1 mmol) is dissolved in 50 mL of tetrahydrofuran (THF) solution. At 0 °C, 3.8 mL of a solution of n-butyllithium (1.6 M) in n-hexane is slowly added under nitrogen. The mixture is stirred at 0 °C for 2 hours. Next, 10 mL of a solution of starting material F1 (3.71 g, 12.7 mmol) in tetrahydrofuran is slowly added. The reaction mixture is then slowly warmed to room temperature and stirred overnight. Dilute hydrochloric acid solution, distilled water, and ethyl acetate are added to the reaction mixture. The aqueous layer is separated and extracted three times with ethyl acetate. The organic layers are combined, dried over sodium sulfate, and filtered. The solvent is removed under reduced pressure. The crude product is then dissolved in anhydrous dichloromethane. 47% boron trifluoride-diethyl ether is then slowly added. The reaction mixture is stirred overnight and then slowly quenched with aqueous NaHCO3 solution. The aqueous layer is then separated, extracted with dichloromethane, dried over sodium sulfate, filtered, concentrated by rotary evaporation, and subjected to column chromatography to give intermediate C1.

[0154] Synthesis of Intermediate D1: Under a nitrogen atmosphere, intermediate C1 (1.86 g, 2.5 mmol) was dissolved in 50 mL of toluene, and raw material 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. The mixture was vigorously stirred. The resulting mixture was refluxed at 105 °C for 10 hours and then cooled to room temperature. Ethyl acetate (100 mL) was then added. The mixture was washed three times with deionized water (100 mL) and dried over anhydrous magnesium sulfate overnight. The ethyl acetate was then evaporated under reduced pressure. The remaining mixture was poured into 100 mL of petroleum ether while stirring. The mixture was filtered to obtain intermediate D1.

[0155] Synthesis of Compound 255: Under a nitrogen atmosphere at 0°C, 10 mL of a solution of tert-butyllithium (1.6 M) in n-pentane is slowly added to 300 mL of a solution of intermediate D1 (11.77 g, 12.5 mmol) in tert-butylbenzene. The mixture is stirred at 60°C for 2 hours. Then, n-pentane is removed under vacuum. Boron tribromide (6.26 g, 25 mmol) is added at 0°C. The reaction mixture is then stirred at room temperature for 1 hour. N,N-diisopropylethylamine (DIEA) (3.25 g, 25.2 mmol) is added at 0°C. After reaching room temperature, the reaction mixture is stirred at 130°C for 6 hours. Then, the reaction mixture is cooled to room temperature. Methanol is added to the reaction mixture to remove residual BBr3. The mixture is separated and extracted with water and dichloromethane. The organic layers are combined, concentrated under vacuum, and subjected to column chromatography to obtain Compound 255.

[0156] Example 8: Synthesis of Compound 48:

[0157] [ka] Synthesis of intermediate M8: A three-neck flask was charged with starting material A1 (10 mmol, 2.71 g) and starting material B8 (10 mmol, 1.72 g) and dissolved in a mixed solvent (60 mL of toluene and 30 mL of ethanol). Pd(PPh3)4 (0.10 mmol, 0.12 g) and 15 mL of 3 mol / L aqueous K2CO3 solution were then added. The mixture was heated to reflux under nitrogen protection and reacted for 12.5 hours. A sample of the reaction mixture was taken and spotted on a plate to confirm completion of the reaction. After cooling to room temperature, the reaction mixture was filtered through a pad of diatomaceous earth and washed with chloroform. The filtrate was evaporated under vacuum. The residue was purified by silica gel column chromatography using hexane / toluene as the eluent to obtain intermediate M8.

[0158] Synthesis of intermediate N8: Intermediate M8 (20 mmol, 6.38 g) and cesium carbonate (50 mmol, 16.3 g) were placed in a two-neck flask, and 80 mL of anhydrous DMF was added under nitrogen protection. The mixture was stirred at room temperature for 35 minutes. Starting material C1 (50 mmol, 14.0 g) was added under nitrogen protection. The solution was refluxed under magnetic stirring for 22 hours, then cooled, filtered, washed, dried, and subjected to column chromatography to obtain intermediate N8.

[0159] Synthesis of intermediate J8: Intermediate N8 (10 mmol, 8.38 g) is dissolved in 100 mL of tetrahydrofuran (THF). At -78 °C, 4.4 mL of a solution of n-butyllithium (2.5 M, 11 mmol) in n-hexane is slowly added while introducing nitrogen. The mixture is stirred at -78 °C for 2.5 hours. Next, 30 mL of a solution of starting material D1 (11 mmol, 1.98 g) in tetrahydrofuran is slowly added. The reaction mixture is then slowly warmed to room temperature and stirred overnight. To the reaction mixture, 40 mL of a dilute hydrochloric acid (1 M) solution, distilled water, and ethyl acetate are added. The aqueous layer is separated and extracted three times with ethyl acetate. The organic layers are combined, dried over sodium sulfate, and filtered. The solvent is removed under reduced pressure. The crude product is then dissolved in anhydrous dichloromethane. 47% boron trifluoride-diethyl ether is then slowly added. The reaction mixture is stirred overnight and then slowly quenched with aqueous NaHCO solution. The aqueous layer is then separated, extracted with dichloromethane, dried over sodium sulfate, filtered, concentrated by rotary evaporation, and subjected to column chromatography to give intermediate J8.

[0160] Synthesis of intermediate K8: To a three-neck flask, intermediate J8 (10.0 mmol, 9.21 g) and 100 mL of glacial acetic acid are added successively under nitrogen protection. The mixture is cooled to 0 °C in a cryogenic bath and protected from light. NBS (15.0 mmol, 2.67 g) is added in batches. The mixture is stirred at 0 °C for 12.5 h. The reaction mixture is concentrated and purified by silica gel column chromatography to give intermediate K8.

[0161] Synthesis of compound 48: Intermediate K8 (10 mmol, 10.0 g) and 120 mL of tert-butylbenzene are placed in a sealed pressure tube under nitrogen protection. At -78°C, a 2.5 M solution of n-butyllithium in n-hexane (12 mmol, 4.8 mL) is added. The system is heated to 60°C and reacted for 2 hours. Next, boron tribromide (15 mmol, 1.5 mL) is added at 0°C. The system is then transferred to room temperature and reacted for an additional 5.5 hours. Next, N,N-diisopropylethylamine (20 mmol, 3.5 mL) is added to the system at 0°C, and the system is heated to 165°C and reacted for 12 hours. After the reaction, the organic layer is concentrated under reduced pressure and purified by silica gel column chromatography to obtain compound 48. A toluene solution (1 x 10 -5 The full width at half maximum at M) is 24 nm.

[0162] Example 9: Synthesis of Compound 64:

[0163] [ka] Synthesis of intermediate M9: A three-neck flask was charged with starting material A1 (10 mmol, 2.71 g) and starting material B9 (10 mmol, 1.72 g) and dissolved in a mixed solvent (60 mL of toluene and 30 mL of ethanol). Pd(PPh3)4 (0.10 mmol, 0.12 g) and 15 mL of 3 mol / L aqueous K2CO3 solution were then added. The mixture was heated to reflux under nitrogen protection and reacted for 12.5 hours. A sample of the reaction mixture was taken and spotted on a plate to confirm completion of the reaction. After cooling to room temperature, the reaction mixture was filtered through a pad of diatomaceous earth and washed with chloroform. The filtrate was evaporated under vacuum. The residue was purified by silica gel column chromatography using hexane / toluene as the eluent to obtain intermediate M9.

[0164] Synthesis of intermediate N9: Intermediate M9 (20 mmol, 6.38 g) and cesium carbonate (50 mmol, 16.3 g) were added to a two-neck flask, and 80 mL of anhydrous DMF was added under nitrogen protection. The mixture was stirred at room temperature for 35 minutes. Starting material C1 (50 mmol, 14.0 g) was added under nitrogen protection. The solution was refluxed under magnetic stirring for 22 hours, then cooled, filtered, washed, dried, and subjected to column chromatography to obtain intermediate N9.

[0165] Synthesis of intermediate J9: Intermediate N9 (10 mmol, 8.38 g) is dissolved in 100 mL of tetrahydrofuran (THF). At -78 °C, 4.4 mL of a solution of n-butyllithium (2.5 M, 11 mmol) in n-hexane is slowly added under nitrogen. The mixture is stirred at -78 °C for 2.5 hours. Next, 30 mL of a solution of starting material D1 (11 mmol, 1.98 g) in tetrahydrofuran is slowly added. The reaction mixture is then slowly warmed to room temperature and stirred overnight. To the reaction mixture, 40 mL of a dilute hydrochloric acid (1 M) solution, distilled water, and ethyl acetate are added. The aqueous layer is separated and extracted three times with ethyl acetate. The organic layers are combined, dried over sodium sulfate, and filtered. The solvent is removed under reduced pressure. The crude product is then dissolved in anhydrous dichloromethane. 47% boron trifluoride-diethyl ether is then slowly added. The reaction mixture is stirred overnight and then slowly quenched with aqueous NaHCO3 solution. The aqueous layer is then separated, extracted with dichloromethane, dried over sodium sulfate, filtered, concentrated by rotary evaporation, and subjected to column chromatography to provide intermediate J9.

[0166] Synthesis of intermediate K9: To a three-neck flask, intermediate J9 (10.0 mmol, 9.21 g) and 100 mL of glacial acetic acid are added successively under nitrogen protection. The mixture is cooled to 0 °C in a cryogenic bath and protected from light. NBS (15.0 mmol, 2.67 g) is added in batches. The mixture is stirred at 0 °C for 12.5 h. The reaction solution is concentrated and purified by silica gel column chromatography to obtain intermediate K9.

[0167] Synthesis of compound 64: Intermediate K9 (10 mmol, 10.0 g) and 120 mL of tert-butylbenzene are placed in a sealed pressure tube under nitrogen protection. At -78°C, a 2.5 M solution of n-butyllithium in n-hexane (12 mmol, 4.8 mL) is added. The system is heated to 60°C and reacted for 2 hours. Next, boron tribromide (15 mmol, 1.5 mL) is added at 0°C. The system is then transferred to room temperature and reacted for an additional 5.5 hours. Next, N,N-diisopropylethylamine (20 mmol, 3.5 mL) is added to the system at 0°C, and the system is heated to 165°C and reacted for 12 hours. After the reaction, the organic layer is concentrated under reduced pressure and purified by silica gel column chromatography to obtain compound 64. A toluene solution (1 x 10 -5 The full width at half maximum at M) is 24 nm.

[0168] Example 10: Synthesis of Compound 533:

[0169] [ka] Synthesis of intermediate M10: A three-neck flask was charged with starting material A1 (10 mmol, 2.71 g) and starting material B10 (10 mmol, 2.46 g) and dissolved in a mixed solvent (60 mL of toluene and 30 mL of ethanol). Pd(PPh3)4 (0.10 mmol, 0.12 g) and 15 mL of 3 mol / L aqueous K2CO3 solution were then added. The mixture was heated to reflux under nitrogen protection and reacted for 12.5 hours. A sample of the reaction mixture was taken and spotted on a plate to confirm completion of the reaction. After cooling to room temperature, the reaction mixture was filtered through a pad of diatomaceous earth and washed with chloroform. The filtrate was evaporated under vacuum. The residue was purified by silica gel column chromatography using hexane / toluene as the eluent to obtain intermediate M10.

[0170] Synthesis of intermediate N10: Add intermediate M10 (20 mmol, 7.86 g) and cesium carbonate (50 mmol, 16.3 g) to a two-neck flask and add 80 mL of anhydrous DMF under nitrogen protection. Stir the mixture at room temperature for 35 minutes. Add raw material C1 (50 mmol, 14.0 g) under nitrogen protection. Reflux the solution under magnetic stirring for 22 hours, then cool, filter, wash, dry, and subject to column chromatography to obtain intermediate N10.

[0171] Synthesis of intermediate J10: Intermediate N10 (10 mmol, 9.12 g) is dissolved in 100 mL of tetrahydrofuran (THF). At -78 °C, 4.4 mL of a solution of n-butyllithium (2.5 M, 11 mmol) in n-hexane is slowly added under nitrogen. The mixture is stirred at -78 °C for 2.5 hours. Next, 30 mL of a solution of starting material D1 (11 mmol, 1.98 g) in tetrahydrofuran is slowly added. The reaction mixture is then slowly warmed to room temperature and stirred overnight. To the reaction mixture, 40 mL of a dilute hydrochloric acid (1 M) solution, distilled water, and ethyl acetate are added. The aqueous layer is separated and extracted three times with ethyl acetate. The organic layers are combined, dried over sodium sulfate, and filtered. The solvent is removed under reduced pressure. The crude product is then dissolved in anhydrous dichloromethane. 47% boron trifluoride in diethyl ether is then slowly added. The reaction mixture is stirred overnight and then slowly quenched with aqueous NaHCO solution. The aqueous layer is then separated, extracted with dichloromethane, dried over sodium sulfate, filtered, concentrated by rotary evaporation, and subjected to column chromatography to give intermediate J10.

[0172] Synthesis of intermediate K10: Intermediate J10 (10.0 mmol, 9.95 g) and 100 mL of glacial acetic acid are added successively to a three-neck flask under nitrogen protection. The mixture is cooled to 0 °C in a cryogenic bath and protected from light. NBS (15.0 mmol, 2.67 g) is added in batches. The mixture is stirred at 0 °C for 12.5 h. The reaction mixture is concentrated and purified by silica gel column chromatography to give intermediate K10.

[0173] Synthesis of compound 533: Intermediate K10 (10 mmol, 10.7 g) and 120 mL of tert-butylbenzene were placed in a sealed pressure tube under nitrogen protection. At -78°C, a 2.5 M solution of n-butyllithium (12 mmol, 4.8 mL) in n-hexane was added. The system was heated to 60°C and reacted for 2 hours. Next, boron tribromide (15 mmol, 1.5 mL) was added at 0°C. The system was then transferred to room temperature and reacted for an additional 5.5 hours. Next, N,N-diisopropylethylamine (20 mmol, 3.5 mL) was added to the system at 0°C, and the system was then heated to 200°C and reacted for 12 hours. After the reaction, the organic layer was concentrated under reduced pressure and purified by silica gel column chromatography to obtain compound 533. A toluene solution (1 x 10 -5 The full width at half maximum at M) is 24 nm.

[0174] The following target compounds are synthesized using the same reaction conditions and the same raw material C1 as in Example 7 for compound 255. The difference is that raw materials E, F, and intermediate G shown in the following table are used.

[0175] [ka] Synthesis of G series intermediates:

[0176] [ka] Synthesis of Intermediate G3: NaO(t-Bu) (3.36 g, 35 mmol), 100 mL of anhydrous toluene, starting material R1 (8.45 g, 30 mmol), starting material P1 (6.55 g, 32.5 mmol), and Pd-Cy-vBRIDP catalyst (0.25 g, 0.5 mmol) were added sequentially under continuous stirring and nitrogen gas introduction. The resulting suspension was heated to 100 °C with silicone oil and stirred continuously at 100 °C for 2 hours under nitrogen gas introduction, followed by extraction with ethyl acetate three times. The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and concentrated to obtain the crude product. The crude product was purified by recrystallization (ethyl acetate / petroleum ether) to obtain Intermediate G3.

[0177] [ka] Synthesis of intermediate G5: Raw material R3 (7.08 g, 25 mmol) was dissolved in 100 mL of toluene, and 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) are added. The mixture is vigorously stirred. The resulting mixture is refluxed at 105 °C for 11 hours and then cooled to room temperature. Ethyl acetate (100 mL) is then added. The mixture is washed three times with deionized water (100 mL) and dried over anhydrous magnesium sulfate overnight. The ethyl acetate is then evaporated under reduced pressure. The remaining mixture is poured into 100 mL of petroleum ether with stirring. The mixture is filtered to give intermediate G5.

[0178] The structural characteristics of the compounds obtained in the examples are shown in Table 1.

[0179] [Table 1] TIFF2025539594000078.tif72170 The PLQY of compound 255 is 98% and the FWHM of compound 255 is 25 nm.

[0180] The PLQY of compound 373 is 94% and the FWHM of compound 373 is 26 nm.

[0181] The PLQY of compound 438 is 98% and the FWHM of compound 438 is 25 nm.

[0182] The PLQY of compound 20 is 97% and the FWHM of compound 20 is 25 nm.

[0183] NOTE: The PLQY (fluorescence quantum yield) and FWHM (full width at half maximum) of compound 255, compound 373, compound 438, and compound 20 in the film state were measured on a Horiba Fluorolog-3 series fluorescence spectrometer.

[0184] The following describes in detail the effects of using the OLED materials synthesized in the present invention in devices using Device Examples 1 to 13 and Device Comparative Examples 1 and 2. Device Examples 2 to 13, Device Comparative Examples 1 and 2, and Device Example 1 of the present invention all use the same device manufacturing process, substrate material, electrode material, and electrode material thickness. The only difference is that the light-emitting layer material in the device has been changed. Tables 2-1 and 3 show the layer structures and test results of device embodiments, respectively.

[0185] (Device Example 1) As shown in Figure 1, the transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (150 nm thick) is sequentially washed with a cleaner (Semiclean M-L20) and pure water. After drying, it is cleaned with ultraviolet ozone to remove organic residues from the transparent ITO surface. Next, using a vacuum deposition system, 10 nm thick films of HT-1 and HI-1 are deposited on the cleaned ITO anode layer 2 to serve as the hole injection layer 3. Here, the mass ratio of HT-1 to HI-1 is 97:3. Next, a 60 nm thick film of HT-1 is deposited as the hole transport layer 4. Next, a 30 nm thick film of EB-1 is deposited as the electron blocking layer 5. After the electron blocking material is deposited, the light-emitting layer 6 of the OLED light-emitting device is prepared using GH-1 and GH-2 as the host material and compound 5 as the doping material. The mass ratio of GH-1 to GH-2 to compound 5 is 69:30:1, and the thickness of the emitting layer is 30 nm. Further, under vacuum, a 5 nm thick film of HB-1 is formed on the emitting layer 6 to form a hole blocking layer 7. Further, under vacuum, a 30 nm thick film of ET-1 and Liq is formed on the hole blocking layer 7 to form an electron transport layer 8. The mass ratio of ET-1 to Liq is 1:1. Using a vacuum evaporation system, a 1 nm thick LiF layer is prepared on the electron transport layer 8 to form an electron injection layer 9. Using a vacuum evaporation system, an 80 nm thick Mg:Ag electrode layer is prepared on the electron injection layer 9 to form a cathode layer 10. The mass ratio of Mg to Ag is 1:9.

[0186] The following describes in detail the effects of using the OLED materials synthesized in the present invention in devices using Device Examples 14 to 26 and Device Comparative Examples 3 and 4. Device Examples 15 to 26, Device Comparative Examples 3 and 4, and Device Example 14 of the present invention all use the same device fabrication process, the same substrate material, the same electrode material, and the same thickness of the electrode material. The only difference is that the light-emitting layer material in the device has been changed. Tables 2-2 and 3 show the layer structures and test results of device embodiments, respectively.

[0187] (Device Example 14) The transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (150 nm thick) is sequentially washed with a cleaner (Semiclean M-L20) and pure water. After drying, it is cleaned with ultraviolet light and ozone to remove organic residues from the transparent ITO surface. Next, using a vacuum deposition system, 10 nm thick films of HT-1 and HI-1 are deposited on the cleaned ITO anode layer 2 to serve as the hole injection layer 3. The mass ratio of HT-1 to HI-1 is 97:3. Next, a 60 nm thick film of HT-1 is deposited as the hole transport layer 4. Next, a 30 nm thick film of EB-1 is deposited as the electron blocking layer 5. After the electron blocking materials are deposited, the light-emitting layer 6 of the OLED light-emitting device is prepared using GH-1 and GH-2 as the host material, GD-1 as the first doping material, and compound 5 as the second doping material. The mass ratio of GH-1 to GH-2 to GD-1 to compound 5 was 66:30:3:1, and the thickness of the emitting layer was 30 nm. A 5 nm thick film of HB-1 was then formed on the emitting layer 6 under vacuum to form a hole blocking layer 7. A 30 nm thick film of ET-1 and Liq was then formed on the hole blocking layer 7 under vacuum to form an electron transport layer 8. The mass ratio of ET-1 to Liq was 1:1. A 1 nm thick LiF layer was then formed on the electron transport layer 8 using a vacuum evaporation system to form an electron injection layer 9. An 80 nm thick Mg:Ag electrode layer was then formed on the electron injection layer 9 using a vacuum evaporation system to form a cathode layer 10. The mass ratio of Mg to Ag was 1:9.

[0188] The molecular structures of the relevant materials are shown below.

[0189] [ka] After the above-described OLED light-emitting device is fabricated, the anode and cathode are connected by a well-known driving circuit, and the current efficiency and lifetime of the device are measured. Tables 2-1 and 2-2 show examples and comparative examples of devices prepared in the same manner. Table 3 shows the test results of the current efficiency and lifetime of the obtained devices.

[0190] [Table 2-1] TIFF2025539594000081.tif255170 TIFF2025539594000082.tif111170 [Table 2-2] TIFF2025539594000084.tif255170 TIFF2025539594000085.tif255170 TIFF2025539594000086.tif42170

[0191] [Table 3] Note: The current efficiency and peak luminance were measured using an IVL (current-voltage-luminance) measurement device (Suzhou Fstar Scientific Instruments). The life test device was a Nippon Giken Kogyo EAS-62C OLED device life tester. LT95 is the time required for the device luminance to decay to 95%. All data are based on a current of 10 mA / cm. 2 was measured.

[0192] From the device data results in Table 3, it can be seen that the emission peak of the compound of the present invention is from 510 nm to 550 nm, and a good green light emission effect can be obtained. Compared with the device comparison examples 1 and 3, the device efficiency and lifetime of the organic light-emitting device of the present invention are significantly improved compared to the OLED device made of conventional materials, regardless of whether it is a single-doped system or a double-doped system. Compared with the device comparison examples 2 and 4, the lifetime of the organic light-emitting device of the present invention is significantly improved compared to the OLED device made of conventional materials, regardless of whether it is a single-doped system or a double-doped system.

[0193] In summary, the above description is merely a preferred embodiment of the present invention, and does not limit the present invention. It should be noted that any modifications, equivalent replacements, and improvements made within the spirit and principle of the present invention fall within the protection scope of the present invention.

Claims

1. A boron-containing resonant organic compound, The structure of the boron-containing resonant organic compound is represented by the following general formula (1): 【Chemistry 1】 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, a substituted or unsubstituted C 1 ~C 10 Alkyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, 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 C 6 ~C 10 aryloxy, substituted or unsubstituted arylamide, substituted or unsubstituted C 6 ~C 30 aryl, substituted or unsubstituted C 2 ~C 30 Heteroaryl of the formula: 2 ~C 30 represents one of the boranyl groups, R 1 ~R 14 any two adjacent groups in the formula (I) can be linked to form a ring; R 18 and R 19 can be linked to form a ring, M 1 is a substituted or unsubstituted C 6 ~C 30 and a substituted or unsubstituted 5- to 30-membered heteroaromatic ring, M 2 represents an R-substituted or unsubstituted 6-membered ring; R is a deuterium atom, a tritium atom, a halogen atom, cyano, or a substituted or unsubstituted C 1 ~C 10 alkyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, 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 C 6 ~C 10 aryloxy, substituted or unsubstituted arylamide, substituted or unsubstituted C 6 ~C 30 aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, and substituted or unsubstituted C 2 ~C 30 represents one of the boranyl groups, The substitution mode of R is a single bond or a polycyclic bond; M 1 and M 2 When 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 all represent hydrogen atoms, X represents a carbon atom or a silicon atom; The substituents that replace the substitutable groups are deuterium atoms, tritium atoms, halogen atoms, cyano, 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- to 30-membered heteroaryl, and deuterium- or tritium-substituted C 2 ~C 30 and optionally selected from one or more of the heteroaryls Boron-containing resonant organic compounds, wherein the heteroatoms in the heteroaryl and heteroaromatic rings are optionally selected from one or more of O, S, N, Si, and B.

2. In general formula (1), R 1 ~R 19 are the same or different and are hydrogen atoms, deuterium atoms, tritium atoms, halogen atoms, cyano, 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 arylamide, substituted or unsubstituted C 6 ~C 30 and substituted or unsubstituted C 2 ~C 30 represents one of the heteroaryls R 1 ~R 14 Any adjacent two of the following may be linked to form a ring: R 18 and R 19 can be linked to form a ring, M 1 is a substituted or unsubstituted C 6 ~C 30 or a substituted or unsubstituted 5- to 30-membered heteroaromatic ring, M 2 represents a substituted or unsubstituted 6-membered ring, M 1 and M 2 When both represent a substituted or unsubstituted benzene ring, R 1 ~R 8 , R 18 and R 19 do not all represent hydrogen atoms, X represents C or Si; The substituents that replace the group include deuterium atoms, tritium atoms, halogen atoms, cyano, 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 Heteroaryls of the formula: 2 ~C 30 2. The boron-containing resonant organic compound according to claim 1, wherein the heteroaryl is selected from any one of the following:

3. The structure of the boron-containing resonant organic compound is represented by general formula (1-1) to general formula (1-3): 【Chemistry 2】 It is represented by one of In the general formulae (1-1) to (1-3), R 1 ~R 25 are the same or different and are hydrogen atoms, deuterium atoms, tritium atoms, halogen atoms, cyano, 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 arylamide, substituted or unsubstituted C 6 ~C 30 and substituted or unsubstituted C 2 ~C 30 represents one of the heteroaryls R 1 ~R 25 Any adjacent two of the following may be linked to form a ring: Ar 3 are the same or different, 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 arylamide, substituted or unsubstituted C 6 ~C 30 and substituted or unsubstituted C 2 ~C 30 represents one of the heteroaryls X represents C or Si; In general formula (1-1), R 1 ~R 8 , R 18 , and R 19 do not all represent hydrogen atoms, The substituents that replace the group include deuterium, tritium, halogen atoms, cyano, 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 Heteroaryls of the formula: 2 ~C 30 3. The boron-containing resonant organic compound according to claim 2, wherein the heteroaryl is selected from any one of the following:

4. The structure of the boron-containing resonant organic compound is represented by general formula (1-4) to general formula (1-6): 【Transformation 3】 It is represented by one of In the general formulae (1-4) to (1-6), R 2 , R 7 , R 10 , R 13 , R 16 , R 18 , R 21 and X have the same meaning as in claim 2; Ar 3 is 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 arylamide, substituted or unsubstituted C 6 ~C 30 and substituted or unsubstituted C 2 ~C 30 represents one of the heteroaryls The substituents that replace the group include deuterium, tritium, halogen atoms, cyano, 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 3. The boron-containing resonant organic compound according to claim 2, wherein the heteroaryl is selected from any one of the following:

5. The structure of the boron-containing resonant organic compound is represented by general formula (1-7) to general formula (1-12): 【Chemistry 4】 It is represented by one of In the general formulas (1-7) to (1-12), R may be the same or different and may represent a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, cyano, 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 arylamide, substituted or unsubstituted C 6 ~C 30 and substituted or unsubstituted C 2 ~C 30 represents one of the heteroaryls X represents C or Si; The substituents for the group may be, if necessary, deuterium, tritium, halogen atoms, cyano, 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 3. The boron-containing resonant organic compound according to claim 2, wherein the heteroaryl is selected from any one of the following:

6. R and R 1 ~R 25 each independently represents a hydrogen atom, a deuterium atom, a tritium atom, a fluorine atom, cyano, adamantyl, methyl, deuterated methyl, tritiated methyl, trifluoromethyl, ethyl, deuterated ethyl, tritiated ethyl, isopropyl, deuterated isopropyl, tritiated butyl, tert-butyl, deuterated tert-butyl, tritiated tert-butyl, cyclopentyl, deuterated cyclopentyl, tritiated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, tritiated phenyl, diphenyl, deuterated diphenyl, tritiated diphenyl, triphenyl, deuterated triphenyl, tritiated triphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthryl, phenanthryl, pyridinyl, phenyl-substituted pyridinyl, quinolyl, furyl, thienyl, benzofuryl, phenyl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, tert-butyl-substituted dibenzofuryl, phenyl-substituted tert-butyl, xanthone, phenyl-substituted triazinyl, phenyl-substituted boranyl, methoxy, and tert-butoxy; Ar 3 are independently selected from phenyl, deuterated phenyl, tritiated phenyl, diphenyl, deuterated diphenyl, tritiated diphenyl, triphenyl, deuterated triphenyl, tritiated triphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthryl, phenanthryl, pyridinyl, phenyl-substituted pyridinyl, quinolyl, furyl, thienyl, benzofuryl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl phenyl-substituted phenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuryl, phenyl-substituted tert-butyl, xanthone, phenyl-substituted triazinyl, phenyl-substituted boranyl, methoxy, and tert-butoxy; M 1 represents one of phenyl, deuterated phenyl, diphenyl, deuterated diphenyl, triphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthryl, phenanthryl, pyridinyl, phenyl-substituted pyridinyl, quinolyl, 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 diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, and xanthone; M 2 represents one of phenyl, deuterated phenyl, pyridinyl, phenyl-substituted pyridinyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, and tert-butyl-substituted phenyl; 6. The boron-containing resonant organic compound according to claim 2, wherein the substituent for the substitutable group is arbitrarily selected from one or more of deuterium, chlorine, fluorine, trifluoromethyl, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-pentyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, naphthyl, anthryl, phenanthryl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolyl, isoquinolyl, furyl, thienyl, indolyl, pyrrolyl, dibenzofuryl, dibenzothienyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazolyl, N-phenylcarbazolyl, carbazolinyl, and azaphenanthryl.

7. R and R 1 ~R 25 each independently represents a hydrogen atom, a cyano, 【Transformation 5】 represents one of the following: Ar 3 has the following structure: 【Transformation 6】 represents one of the following: M 1 is the following ring structure: 【Transformation 7】 represents one of the following: M 2 is the following ring structure: 【Transformation 8】 represents Z is CR a represents R a are each independently a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, cyano, adamantyl, methyl, deuterated methyl, tritiated methyl, trifluoromethyl, ethyl, deuterated ethyl, tritiated ethyl, isopropyl, deuterated isopropyl, tritiated isopropyl, tert-butyl, deuterated tert-butyl, tritiated tert-butyl, cyclopentyl, deuterated cyclopentyl, tritiated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, tritiated phenyl, diphenyl, deuterated diphenyl, tritiated diphenyl, triphenyl, deuterated triphenyl, tritiated triphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthryl, phenanthryl, pyridinyl, phenyl-substituted pyridinyl, quinolyl, furyl, thienyl, benzofuryl, dibenzofuryl, dibenzothienyl, carbazolyl, N 6. The boron-containing resonant organic compound of claim 2, wherein the substituted or unsubstituted phenyl is substituted or unsubstituted phenyl, phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuryl, phenyl-substituted tert-butyl, xanthone, phenyl-substituted triazinyl, phenyl-substituted boranyl, methoxy, and tert-butoxy.

8. The structure of the boron-containing resonant organic compound is represented by the general formula (A-1): 【Chemistry 9】 is expressed as In general formula (A-1), R 1 ~R 19 each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano, a substituted or unsubstituted C 1 ~C 10 alkyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, 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 arylamide, substituted or unsubstituted C 6 ~C 30 aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, and substituted or unsubstituted C 2 ~C 30 represents one of the boranyl groups, R 1 ~R 19 any two adjacent groups in may be linked to form a ring; M 1 is a substituted or unsubstituted C 6 ~C 30 or a substituted or unsubstituted 5- to 30-membered heteroaromatic ring, M 2 represents an R-substituted or unsubstituted 6-membered ring; R is a deuterium atom, a halogen atom, cyano, or a substituted or unsubstituted C 1 ~C 10 alkyl, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, 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 arylamide, substituted or unsubstituted C 6 ~C 30 aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, and substituted or unsubstituted C 2 ~C 30 represents one of the boranyl groups, The substitution mode of R is a single bond or a polycyclic bond; M 1 and M 2 When 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 all represent hydrogen atoms, The substituents that replace the substitutable groups are deuterium atoms, halogen atoms, cyano, C 1 ~C 10 Alkyl, C 3 ~C 10 Cycloalkyl, C 6 ~C 30 and 5- to 30-membered heteroaryl, 2. The boron-containing resonant organic compound of claim 1, wherein the heteroatoms in the heteroaryl and heteroaromatic rings are optionally selected from one or more of O, S, N, Si, and B.

9. The structure of the boron-containing resonant organic compound is represented by the general formula (A-2): 【Chemistry 10】 is expressed as In general formula (A-2), R 1 ~R 23 are each independently a hydrogen atom, a deuterium 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 2 ~C 10 Alkenyl, substituted or unsubstituted C 2 ~C 10 Alkynyl, substituted or unsubstituted C 1 ~C 10 alkoxy, substituted or unsubstituted arylamide, substituted or unsubstituted C 6 ~C 30 aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, and substituted or unsubstituted C 2 ~C 30 represents any one of the following boranyls: R 1 ~R 23 any two adjacent groups in may be linked to form a ring; 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, The substituents that replace the substitutable groups are deuterium atoms, halogen atoms, cyano, C 1 ~C 10 Alkyl, C 3 ~C 10 Cycloalkyl, C 6 ~C 30 and 5- to 30-membered heteroaryl, 2. The boron-containing resonant organic compound of claim 1, wherein the heteroatom in the heteroaryl is optionally selected from one or more of O, S, N, Si, and B.

10. The structure of the boron-containing resonant organic compound is represented by the general formula (A-3): 【Chemistry 11】 is expressed as In general formula (A-3), R 2 , R 7 , R 10 , R 13 , R 16 and 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, substituted or unsubstituted C 3 ~C 10 Cycloalkyl, 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 arylamide, substituted or unsubstituted C 6 ~C 30 aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, and substituted or unsubstituted C 2 ~C 30 represents one of the boranyl groups, R 18 represents a deuterium 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 2 ~C 10 Alkenyl, substituted or unsubstituted C 2 ~C 10 Alkynyl, substituted or unsubstituted C 1 ~C 10 alkoxy, substituted or unsubstituted arylamide, substituted or unsubstituted C 6 ~C 30 aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, and substituted or unsubstituted C 2 ~C 30 represents one of the boranyl groups, The substituents that replace the substitutable groups are deuterium atoms, halogen atoms, cyano, C 1 ~C 10 Alkyl, C 3 ~C 10 Cycloalkyl, C 6 ~C 30 and 5- to 30-membered heteroaryl, 10. The boron-containing resonant organic compound of claim 9, wherein the heteroatom in the heteroaryl is optionally selected from one or more of O, S, N, Si, and B.

11. M 1 represents any one of the following substituted or unsubstituted groups: phenyl, naphthyl, anthryl, phenanthryl, pyridinyl, quinolyl, 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, and spirofluorenyl; M 2 represents any one of the R-substituted or unsubstituted groups phenyl, naphthyl, anthryl, phenanthryl, pyridinyl, and quinolyl; R is a deuterium atom, a halogen atom, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridinyl, substituted or unsubstituted quinolyl, represents substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuryl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amido, or substituted or unsubstituted triazinyl; 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 , and R 23 each independently represents a hydrogen atom, a deuterium atom, a halogen atom, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridinyl, substituted or unsubstituted cyclohex ... noryl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuryl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amido, or substituted or unsubstituted triazinyl; 11. The boron-containing resonant organic compound of claim 1, 8, 9, or 10, wherein the substituents for the group are arbitrarily selected from one or more of deuterium atoms, chlorine atoms, fluorine atoms, trifluoromethyl, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-pentyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, naphthyl, anthryl, phenanthryl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolyl, isoquinolyl, furyl, thienyl, indolyl, pyrrolyl, dibenzofuryl, dibenzothienyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazolyl, N-phenylcarbazolyl, carbazolinyl, and azaphenanthryl.

12. M 1 has the following structure: 【Chemistry 12】 represents one of the following: M 2 has the following structure: 【Chemistry 13】 represents one of the following: Z represents C-(H) or C-(R); 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 18 , R 19 , R 20 , R 21 , R 22 , and R 23 each independently represents a hydrogen atom, a deuterium atom, methyl, ethyl, isopropyl, tert-butyl, cyano, trifluoromethyl, 【Chemistry 14】 【change】 11. The boron-containing resonant organic compound of claim 1, 8, 9, or 10, wherein the compound is any one of:

13. M 1 has the following structure: 【Chemistry 15】 represents one of the following: M 2 has the following structure: 【Chemistry 16】 represents one of the following: Z represents C-(H) or C-(R); 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 , and R 23 each independently represents a hydrogen atom, a deuterium atom, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, 【Chemistry 17】 represents one of the following: R 18 and R 19 each independently represents a hydrogen atom, cyano, t-butyl, [Chemistry 18] 【change】 represents one of the following: Ar 3 has the following structure: 【Chemistry 19】 13. The boron-containing resonant organic compound according to claim 1, wherein the boron-containing resonant organic compound is any one of the following:

14. A specific structural formula of the boron-containing resonant organic compound is the following structure: 【Chemistry 20】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 2. The boron-containing resonant organic compound according to claim 1, wherein the compound is any one of the following:

15. An organic light-emitting device having, in this order, a substrate, a first electrode, a second electrode, and a functional layer, 15. An organic light-emitting device, wherein the functional layer is disposed between the first electrode and the second electrode, the functional layer comprising the boron-containing resonant organic compound according to claim 1 .

16. the functional layer has an emitting layer, the emitting layer including a host material and a doping material; 16. An organic light-emitting device according to claim 15, wherein the doping material is a boron-containing resonant organic compound according to any one of claims 1 to 14.

17. the functional layer has an emitting layer, the emitting layer including a first host material, a second host material, and a doping material; 16. The organic light-emitting device of claim 15, wherein at least one of the first host material and the second host material is a TADF material, and the doping material is a boron-containing resonant organic compound according to any one of claims 1 to 14.

18. the functional layer has an emitting layer, the emitting layer including a host material, an exciton-sensitized material, and a doping material; the exciton-sensitized material is a complex containing a metal element, 16. An organic light-emitting device according to claim 15, wherein the doping material is a boron-containing resonant organic compound according to any one of claims 1 to 14.

19. 15. A material for an organic electroluminescent device comprising a boron-containing resonant organic compound according to any one of claims 1 to 14.

20. 15. Use of a boron-containing resonant organic compound according to any one of claims 1 to 14 in an organic electroluminescent device.

21. The use according to claim 20, wherein the organic light-emitting functional layer has a light-emitting layer, and the light-emitting layer uses the boron-containing resonant organic compound according to any one of claims 1 to 14.

22. 19. A display member comprising an organic light emitting device according to any one of claims 15 to 18.

23. 19. A lighting device comprising an organic light emitting device according to any one of claims 15 to 18.

24. 19. An electronic device comprising an organic light-emitting device according to any one of claims 15 to 18.

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