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

Abstract

The present application relates to a kind of boron-containing resonance type organic compound and the organic electroluminescent device comprising it, belong to semiconductor technical field, the present application provides the structure of compound as shown in general formula (A): The compound of the present application is used as the doping material in the light-emitting layer material of OLED light-emitting device, can be used as the light-emitting layer green light doping material of organic electroluminescent device, so as to improve the life of device.

Description

Technical Field

[0001] This invention relates to the field of semiconductor technology, and more particularly to a boron-containing resonant organic compound and an organic electroluminescent device containing the same. Background Technology

[0002] Organic light-emitting diodes (OLEDs) offer significant advantages over liquid crystal displays (LCDs), including being lighter and thinner, having higher color contrast, lower power consumption, faster response times, higher resolution, and greater flexibility. They are considered poised to dominate future display terminal products. With the advent of the 5G era, the new information display industry urgently needs to evolve. Early color gamut standards (BT.709 and DCIP3) are no longer sufficient to meet the high-quality technological demands of display products. To achieve ultra-high definition and higher image quality, the new generation display standard (BT.2020) is driving the development of OLED luminescent materials towards higher color purity, requiring core luminescent materials to have a narrower emission spectrum. Currently, among the three commercially available OLED color display technologies (red, green, and blue), blue light uses traditional fluorescent triplet-triplet transition (TTF) technology. This technology has lower efficiency but higher color purity, and it has basically met the BT.2020 display specifications. Green and red light use phosphorescence technology, which has high efficiency. Red light is close to the BT.2020 display specifications, while green light is limited by the wider emission spectrum of phosphorescence, which is significantly different from the requirements of high-definition display specifications. Therefore, developing high color purity green OLED materials is crucial.

[0003] Since 2020, green light materials with narrow half-width at half-maximum (WHM < 30nm) based on boron-nitrogen resonant structures have been successively reported: DOI:10.1002 / adom.201902142, DOI:10.1002 / anie.202008264, DOI:10.1021 / jacs.0c10081, DOI:10.1038 / s41467-022-32607-3, DOI:10.1002 / anie.202202380, etc., demonstrating the extremely high color purity and efficiency of this type of material, which has become the development trend of high color purity green OLED. However, there are still many technical challenges in the development of green ultra-high color purity materials with boron-nitrogen structures. Existing materials also have the drawbacks of insufficient efficiency and lifespan to meet the needs of mass production. Developing narrow half-peak width green light materials based on boron-nitrogen resonant structures that can meet practical applications is a key technology for the next generation of display devices with high color purity, high color gamut coverage, high efficiency and high immersion.

[0004] In addition, sensitization technology combines triplet exciton sensitizing materials (including but not limited to TADF materials and phosphorescent materials) with fluorescent doping materials. By using triplet exciton sensitizing materials as exciton sensitization media, it makes full use of triplet excitons and transfers energy to fluorescent doping materials through energy transfer, which can also achieve 100% in-device quantum efficiency. This technology can make up for the shortcomings of insufficient exciton utilization of fluorescent doping materials and effectively leverage the characteristics of high fluorescence quantum yield, high device stability, high color purity and low cost of fluorescent doping materials, which has broad prospects for OLED applications. For example, CN107507921A and CN110492006A disclose a light-emitting layer combination technology using TADF materials with a minimum singlet and triplet energy level difference of less than or equal to 0.2 eV as the main body and boron-containing materials as dopants; CN110492005A and CN110492009A disclose a light-emitting layer combination scheme using exciton complexes as the main body and boron-containing materials as dopants; both can achieve efficiencies comparable to phosphorescence and relatively narrow half-peak widths (HWHM). Therefore, developing sensitization technologies based on narrow HWHM boron-containing light-emitting materials has unique advantages and strong potential for improving BT.2020 display performance. Summary of the Invention

[0005] To address the aforementioned problems in the prior art, this invention provides a boron-containing resonant organic compound and an organic electroluminescent device comprising the same. The compound of this invention can be used as a green doping material for the emitting layer of an organic electroluminescent device.

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

[0007]

[0008] Each occurrence of Z is independently represented as C-(H) or C-(R0); each occurrence of R0 is independently represented as a deuterium atom, tritium atom, halogen atom, cyano group, or substituted or unsubstituted C1 to C2 groups. 10 Alkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted aromatic amino groups, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 heteroaryl, substituted or unsubstituted C2-C 30 One of the boron alkyl groups; any adjacent R0s can be linked to form a ring;

[0009] M1 and M2 independently represent substituted or unsubstituted C6-C, respectively.30 aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0010] R0 and M2 can be linked to form a ring; M1 and M2 can be linked to other groups through carbon atoms to form a ring;

[0011] The substituents used to replace the aforementioned substituted groups are selected from deuterium atoms, tritium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl groups, C3-C 10 cycloalkyl, C6-C 30 Aryl, C2~C 30 One or more of the heteroaryl groups;

[0012] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0013] In a preferred embodiment, the structure of the boron-containing resonance organic compound is shown in general formula (1):

[0014]

[0015] Each occurrence of Z is independently represented as C-(H) or C-(R0); each occurrence of R0 is independently represented as a deuterium atom, tritium atom, halogen atom, cyano group, or substituted or unsubstituted C1 to C2 groups. 10 Alkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted aromatic amino groups, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 heteroaryl, substituted or unsubstituted C2-C 30 One of the boroalkyl groups;

[0016] R a R b R c R d R e R f Each of the following can be represented independently as a hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, or substituted or unsubstituted C1-C group. 10 Alkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted aromatic amino groups, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C2-C 30 One of the boroalkyl groups;

[0017] M1 and M2 independently represent substituted or unsubstituted C6-C, respectively. 30 aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0018] R b M1 and M2 can form a ring; M1 and M2 can form a ring with other groups through carbon atoms;

[0019] The substituents used to replace the aforementioned substituted groups are selected from deuterium atoms, tritium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl groups, C3-C 10 cycloalkyl, C6-C 30 Aryl, C2~C 30 One or more of the heteroaryl groups;

[0020] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0021] In a preferred embodiment, the structure of the boron-containing resonance organic compound is shown in general formula (A-1), general formula (A-2), or general formula (A-3):

[0022]

[0023] In general formulas (A-1) to (A-3), the Z is defined in general formula (A);

[0024] X is represented as O or S;

[0025] Each occurrence of Z1 is independently represented as C-(H) or C-(R1); each occurrence of R1 is independently represented as a deuterium atom, tritium atom, halogen atom, cyano group, or substituted or unsubstituted C1 to C1. 10 Alkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted aromatic amino groups, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 heteroaryl, substituted or unsubstituted C2-C 30 One of the boroalkyl groups; any adjacent R1s can be linked to form a ring;

[0026] The R mEach of the following can be represented independently as a hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, or substituted or unsubstituted C1-C group. 10 Alkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted aromatic amino groups, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 heteroaryl, substituted or unsubstituted C2-C 30 One of the boroalkyl groups;

[0027] The substituents used to replace the aforementioned substituted groups are selected from deuterium atoms, tritium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl groups, C3-C 10 cycloalkyl, C6-C 30 Aryl, C2~C 30 One or more of the heteroaryl groups;

[0028] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0029] In a preferred embodiment, the structure of the boron-containing resonance organic compound is shown in general formula (1-1), general formula (1-2), or general formula (1-3):

[0030]

[0031] In general formulas (1-1) to (1-3), Z and R a R b R c R d R e R f Same as the limitations in general formula (1);

[0032] X is represented as O or S;

[0033] Each occurrence of Z1 is independently represented as C-(H) or C-(R1); each occurrence of R1 is independently represented as a deuterium atom, tritium atom, halogen atom, cyano group, or substituted or unsubstituted C1 to C1. 10 Alkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted aromatic amino groups, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30heteroaryl, substituted or unsubstituted C2-C 30 One of the boroalkyl groups;

[0034] The R m Each of the following can be represented independently as a hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, or substituted or unsubstituted C1-C group. 10 Alkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted aromatic amino groups, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 heteroaryl, substituted or unsubstituted C2-C 30 One of the boroalkyl groups;

[0035] The substituents used to replace the aforementioned substituted groups are selected from deuterium atoms, tritium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl groups, C3-C 10 cycloalkyl, C6-C 30 Aryl, C2~C 30 One or more of the heteroaryl groups;

[0036] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0037] In a preferred embodiment, the boron-containing resonance organic compound has the structure shown in general formulas (1-4), (1-5), or (1-6):

[0038]

[0039] In general formulas (1-4) to (1-6), Z, M1, M2, and R... b R c R d R e R f Same as the limitation in general formula (1).

[0040] In a preferred embodiment, the structure of the boron-containing resonance organic compound is shown in general formula (1-7) or general formula (1-8):

[0041]

[0042] In general formulas (1-7) and (1-8), Z, Z1, X, and R... a R c R d R e R fR m Same limitations as mentioned above.

[0043] In a preferred embodiment, the structure of the boron-containing resonance organic compound is shown in general formula (2-1) or general formula (2-2):

[0044]

[0045] In general formulas (2-1) and (2-2), Z, Z1, and R... c R d R e R f Same limitations as mentioned above.

[0046] X1 is represented as O or S;

[0047] Each occurrence of Z2 is independently represented as C-(H) or C-(R2); each occurrence of R2 is independently represented as a deuterium atom, tritium atom, halogen atom, cyano group, or substituted or unsubstituted C1 to C2 group. 10 Alkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted aromatic amino groups, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 heteroaryl, substituted or unsubstituted C2-C 30 One of the boron alkyl groups; any two adjacent R2s can be linked to form a ring;

[0048] The substituents used to replace the aforementioned substituted groups are selected from deuterium atoms, tritium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl groups, C3-C 10 cycloalkyl, C6-C 30 Aryl, C2~C 30 One or more of the heteroaryl groups;

[0049] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0050] In a preferred embodiment, M1 and M2 represent substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiophenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted indole[3,2,1-jk]carbazolyl, substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, or substituted or unsubstituted spirofluorenyl.

[0051] The R a R b R c R d R e R f R m Each of these can be independently represented as a hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted isopropyl group, substituted or unsubstituted tert-butyl group, substituted or unsubstituted cyclohexyl group, substituted or unsubstituted adamantyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted diphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthracene group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted pyridyl group, substituted or unsubstituted... Substituted quinolinyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amino, substituted or unsubstituted triazineyl;

[0052] R0, R1, and R2 are independently represented as deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted isopropyl group, substituted or unsubstituted tert-butyl group, substituted or unsubstituted cyclohexyl group, substituted or unsubstituted adamantyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted diphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthracene group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted pyridyl group, and substituted... Or unsubstituted quinolinyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiophene, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amino, substituted or unsubstituted triazineyl;

[0053] The substituents used for the substituent groups are selected from one or more of the following: deuterium atom, chlorine atom, fluorine atom, trifluoromethyl, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheneyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheninyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazoleyl, N-phenylcarbazoleyl, carbazolinyl, and aziphenanthryl.

[0054] Preferably, M1 and M2 are represented by the following structure:

[0055]

[0056] Any one of them;

[0057] The range of Z is the same as that defined in general formula (1);

[0058] The R a R b R c R d R e R f R m Each can be represented independently as:

[0059] Hydrogen atom, deuterium atom, methyl, ethyl, isopropyl, tert-butyl, cyano any one of them;

[0060] R0, R1, and R2 are each independently represented as follows:

[0061] Deuterium atom, methyl, ethyl, isopropyl, tert-butyl, cyano Any one of them.

[0062] In a preferred embodiment, the boron-containing resonance organic compound has a specific structural formula of any one of the following:

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074] An organic light-emitting device comprises, in sequence, a substrate, a first electrode, a second electrode, and a functional layer, wherein the functional layer is located between the first electrode and the second electrode, and the functional layer contains the boron-containing resonant organic compound.

[0075] Preferably, the functional layer includes a light-emitting layer, which comprises a host material and a dopant material, wherein the dopant material is the boron-containing resonant organic compound.

[0076] Preferably, the functional layer includes a light-emitting layer, which includes a first host material, a second host material, and a dopant material. At least one of the first host material and the second host material is a TADF material, and the dopant material is the boron-containing resonant organic compound.

[0077] In a preferred embodiment, the functional layer includes a light-emitting layer, which comprises a host material, an exciton-sensitizing material, and a dopant material. The exciton-sensitizing material is a complex containing a metal element, and the dopant material is the boron-containing resonant organic compound.

[0078] Compared with the prior art, the beneficial technical effects of the present invention are as follows:

[0079] (1) The compound of the present invention can be used as a dopant material for OLED devices, and can emit green fluorescence under the action of an electric field. It can be applied to OLED lighting or OLED display fields.

[0080] (2) The compound of the present invention, as a doping material, introduces a phosphorus photosensitizer, which can effectively improve the device lifetime;

[0081] (3) The compounds of this invention have a narrower FWHM spectrum, which can effectively improve the color gamut of the device;

[0082] The compounds of this invention have a narrow half-width at half-maximum (WHM) characteristic and can be used as green light doping materials for the light-emitting layer of organic electroluminescent devices, thereby improving the device's lifetime. Attached Figure Description

[0083] Figure 1 This is a schematic diagram of the structure of an OLED device in which the materials listed in this invention are applied;

[0084] Wherein, 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 a light-emitting 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. Detailed Implementation

[0085] The present invention will now be described in detail with reference to the accompanying drawings and embodiments.

[0086] In this invention, the terms "upper," "lower," "top," and "bottom," used to describe electrodes, organic electroluminescent devices, and other structures, indicate orientation only in a specific state and do not imply that the structure can only exist in that orientation. Conversely, if the structure can be repositioned, such as by inverting it, the orientation of the structure changes accordingly. Specifically, in this invention, the "bottom" or "lower" side of the electrode refers to the side of the electrode closer to the substrate during fabrication, while the opposite side farther from the substrate is the "top" or "upper" side.

[0087] In this invention, "can be linked into a ring" means that the two groups can be unlinked or linked together to form a ring, preferably linked by a C-C single bond, an O atom, an S atom, CQ1Q2, and NQ3, where Q1, Q2, and Q3 represent substituted or unsubstituted C1-C groups.10 Alkyl, substituted or unsubstituted C6-C 30 Aryl or substituted or unsubstituted C2-C 30 Mixed aromatic compounds.

[0088] In this invention, the substituted or unsubstituted aromatic amino group refers to... Wherein Q4 and Q5 represent substituted or unsubstituted aromatic groups, and Q4 and Q5 preferably represent substituted or unsubstituted C6-C groups. 30 Aryl or substituted or unsubstituted C2-C 30 Mixed aromatic compounds.

[0089] In this invention, C6-C is substituted or unsubstituted. 30 Aryl groups refer to substituted or unsubstituted phenyl groups, substituted or unsubstituted naphthyl groups, substituted or unsubstituted anthraquinyl groups, substituted or unsubstituted fluorenyl groups, substituted or unsubstituted dimethylfluorenyl groups, substituted or unsubstituted diphenylfluorenyl groups, substituted or unsubstituted spirofluorenyl groups, substituted or unsubstituted phenanthrene groups, substituted or unsubstituted tetraphenyl groups, substituted or unsubstituted pyrene groups, substituted or unsubstituted biphenyl groups, substituted or unsubstituted para-triphenyl groups, substituted or unsubstituted meta-triphenyl groups, and substituted or unsubstituted phenyl groups. The group may contain, but is not limited to, a fused ring consisting of a substituted or unsubstituted triphenyl group, a substituted or unsubstituted peryl group, a substituted or unsubstituted indole group, a combination thereof, or a combination of the aforementioned groups.

[0090] In this invention, substituted or unsubstituted C2-C 30 Heteroaryl refers to substituted or unsubstituted furanyl, substituted or unsubstituted thiophene, substituted or unsubstituted pyrrole, 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 pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted triazine, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophene, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted... The fused ring of substituted indolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted naphridyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridineyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenthiazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted fumonyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoleyl, combinations thereof, or combinations of the foregoing groups, but not limited thereto.

[0091] The C1-C of this invention 10 Alkyl groups (including straight-chain alkyl and branched-chain alkyl) refer 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, 1-butylpentyl, etc., but are not limited to these.

[0092] The C3-C of this invention 10 Cycloalkyl refers to a monovalent monocyclic saturated hydrocarbon group comprising 3 to 10 carbon atoms as cyclic atoms. In this document, C4-C9 cycloalkyl groups are preferred, C5-C8 cycloalkyl groups are more preferred, and C5-C7 cycloalkyl groups are particularly preferred. Non-limiting examples may include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl, and cycloheptyl.

[0093] The halogen atom mentioned in this invention refers to a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0094] The C1-C of this invention 10 Alkoxy groups include, but are not limited to, alkoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, or isopropoxy.

[0095] The C2-C of this invention 10 Alkenyl refers to vinyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1,1-dimethylallyl, 1-methylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, and 3-phenyl-1-butenyl, etc., but is not limited to these.

[0096] The substituents used for the substituent groups are selected from one or more of the following: deuterium atom, chlorine atom, fluorine atom, trifluoromethyl, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthrene, pyridinyl, pyrazinyl, pyrazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheneyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheninyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazoleyl, N-phenylcarbazoleyl, carbazolinyl, and aziphenanthreneyl.

[0097] As the substrate for the organic electroluminescent device of this invention, any substrate commonly used in organic electroluminescent devices can be used. Examples include transparent substrates, such as glass or transparent PI film substrates; and opaque substrates, such as silicon substrates. Different substrates have different mechanical strengths, thermal stability, transparency, surface smoothness, and water resistance. Their application varies depending on their properties. In this invention, a transparent PI film substrate is preferred. There are no particular limitations on the thickness of the substrate.

[0098] A first electrode is formed on a substrate, and the first electrode and a second electrode may be opposite 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. When 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). When the first electrode is a semi-transmissive electrode or a reflective electrode, it may include metals such as Ag, Mg, Al, Pt, Pd, Au, Ni, Nd, Ir, or Cr, or it may be an alloy of several metals, or a combination of metals, metal oxides, or metal alloys. The thickness of the first electrode layer depends on the material used, and is typically 50-500 nm, preferably 70-300 nm, and more preferably 100-200 nm.

[0099] The organic functional material layer disposed between the first electrode and the second electrode includes, from bottom to top, a hole transport region, a light-emitting layer, and an electron transport region.

[0100] In this invention, the hole transport region constituting the organic electroluminescent device can be exemplified by a hole injection layer, a hole transport layer, an electron blocking layer, etc.

[0101] As for the materials used in the hole injection layer, hole transport layer, and electron blocking layer, any material can be selected from known materials used in organic electroluminescent devices.

[0102] The hole injection layer comprises a host organic material capable of conducting holes, and a p-type doped material with a deep HOMO level (correspondingly, a deep LUMO level). Based on empirical observations, to achieve smooth hole injection from the anode to the organic film, the HOMO level of the host organic material used in the anode interface buffer layer must possess certain characteristics with the p-doped material. This is necessary to enable charge transfer states between the host and doped materials, achieve ohmic contact between the buffer layer and the anode, and realize efficient hole injection conduction from the electrode to the hole injection layer.

[0103] Based on the above empirical summary, for hole-based host organic materials with different HOMO energy levels, it is necessary to select different P-doped materials to match them in order to achieve ohmic contact at the interface and improve the hole injection effect.

[0104] Preferably, the main organic material used as the hole injection layer of the present invention may be selected from compounds disclosed in the prior art:

[0105]

[0106] Preferably, the p-type doped material is a charge-conducting compound disclosed in the prior art. The p-type dopant can be selected from compounds disclosed in any of the following documents: WO2011073149A, EP1968131A1, EP2276085A1, EP2213662A1, EP1722602A1, EP2045848A1, DE10200703122. 0A1, US20100181555A1, US20100102709A1, WO2009003455A1, WO2010094378A1, WO2011120709A1, US20100096600A1, DE102012209523A1, CN101728485A and WO2012095143A1, but not limited to these.

[0107] In one embodiment of the invention, the hole injection layer comprises a p-type dopant material selected from the following charge-conducting materials: quinone derivatives, such as tetracyanoquinone dimethyl (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethyl (F4-TCNQ); or hexaazatriphenyl derivatives, such as 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenyl (HAT-CN); or cyclopropane derivatives, such as 4,4',4”-((1E,1'E,1”E)-cyclopropane-1,2,3-trimethylenetris(cyanoformyl))tris(2,3,5,6-tetrafluorobenzyl); or metal oxides, such as tungsten oxide and molybdenum oxide, but not limited thereto.

[0108] In the hole injection layer of the present invention, the ratio of hole transport material to P-type doped material is 99:1-95:5, preferably 99:1-97:3, based on mass.

[0109] The thickness of the hole injection layer of the present invention can be 5-100 nm, preferably 5-50 nm, and more preferably 5-20 nm, but the thickness is not limited to this range.

[0110] Preferably, the hole transport layer material of the present invention may be selected from the compounds disclosed in the prior art:

[0111]

[0112] Preferably, the main organic material used as the hole transport layer material and the hole injection layer of the present invention is selected from the same compound.

[0113] The thickness of the hole transport layer of the present invention can be 5-200 nm, preferably 10-150 nm, and more preferably 20-100 nm, but the thickness is not limited to this range.

[0114] In one embodiment of the present invention, the electron blocking layer material may be selected from the compounds disclosed in the prior art:

[0115]

[0116] The thickness of the electron blocking layer of the present invention can be 1-50 nm, preferably 5-40 nm, but the thickness is not limited to this range.

[0117] After forming the hole injection layer, hole transport layer, and electron blocking layer, a corresponding light-emitting layer is formed on top of the electron blocking layer.

[0118] The light-emitting layer may include a host material and a dopant material. The host material may be a green light host material commonly used in the art, and the dopant material may be a boron-containing resonant organic compound represented by the general formula (1) of this invention.

[0119] The light-emitting layer can contain a single-substrate material or a dual-substrate material;

[0120] The dual-body material comprises a first body material and a second body material, wherein preferably at least one of the first body material and the second body material is a TADF material;

[0121] TADF materials refer to materials with thermally activated delayed fluorescence properties. They are characterized by a small energy difference between the first excited singlet and triplet states, allowing for the simultaneous utilization of both singlet and triplet excitons generated within the device, thus enabling the exciton utilization rate of electrogenerated excitons within the device to approach 100%. Compared to traditional fluorescent materials, TADF materials exhibit higher exciton utilization.

[0122] The light-emitting layer may include a host material, an exciton-sensitizing material, and a dopant material;

[0123] Exciton-sensitized materials refer to materials that enable the luminescent material in the luminescent layer to fully utilize electroexcitons, thereby allowing the luminescent layer to ultimately produce the emission spectrum of the sensitized material. Exciton sensitizers may perform functions such as exciton capture, exciton conversion, and exciton transfer in electroluminescent devices. The boron-containing resonance organic compound shown in the general formula (1) of this invention, when used in combination with the exciton-sensitized material, has a significant improvement effect on problems such as device efficiency improvement, exciton annihilation in the device, and efficiency reduction.

[0124] In the light-emitting layer of the present invention, the ratio of the host material to the dopant material is 99:1-70:30, preferably 99:1-85:15 and more preferably 97:3-87:13, based on mass.

[0125] The thickness of the light-emitting layer can be adjusted to optimize luminous efficiency and driving voltage. The preferred thickness range is 5 nm to 50 nm, more preferably 10-50 nm, and even more preferably 15-40 nm, but the thickness is not limited to this range.

[0126] In this invention, the electron transport region may include, from bottom to top, a hole blocking layer, an electron transport layer, and an electron injection layer disposed on the light-emitting layer, but is not limited thereto.

[0127] A hole-blocking layer is a layer that prevents holes injected from the anode from penetrating the light-emitting layer and entering the cathode, thereby extending the device's lifetime and improving its performance. The hole-blocking layer of this invention can be disposed on top of the light-emitting layer. As the hole-blocking layer material for the organic electroluminescent device of this invention, compounds with hole-blocking properties known in the prior art can be used, for example:

[0128]

[0129] The thickness of the hole blocking layer of the present invention can be 2-200nm, preferably 5-150nm, more preferably 5-50nm, but the thickness is not limited to this range.

[0130] An electron transport layer may be disposed above the light-emitting layer or (if present) a hole-blocking layer. The electron transport layer material is one that readily receives electrons from the cathode and transfers these received electrons to the light-emitting layer. Preferably, a material with high electron mobility is used. As the electron transport layer of the organic electroluminescent device of the present invention, electron transport layer materials disclosed in the prior art for organic electroluminescent devices can be used, for example:

[0131]

[0132] In a preferred embodiment of the invention, the electron transport layer further includes other compounds conventionally used in electron transport layers, such as Alq3, LiQ, preferably LiQ.

[0133] The thickness of the electron transport layer of the present invention can be 10-80 nm, preferably 20-60 nm and more preferably 25-45 nm, but the thickness is not limited to this range.

[0134] An electron injection layer can be disposed above the electron transport layer. The electron injection layer material is typically preferably a material with a low work function, which facilitates electron injection into the organic functional material layer. As the electron injection layer material for the organic electroluminescent device of this invention, electron injection layer materials disclosed in the prior art for organic electroluminescent devices can be used, such as LiF, Cs₂CO₃, CsF, Csq, NaF, MgF₂, CaF₂, Al₂O₃, Yb, etc.

[0135] The thickness of the electron injection layer of the present invention can be 0.1-5 nm, preferably 0.5-3 nm and more preferably 0.8-1.5 nm, but the thickness is not limited to this range.

[0136] The second electrode may be disposed above the electron transport region. The second electrode may be a cathode. The second electrode may be a transmission electrode, a semi-transmission electrode, or a reflection electrode. When the second electrode is a transmission electrode, it may include, for example, Li, Yb, Ca, LiF / Ca, LiF / Al, Al, Mg, BaF, Ba, Ag, or compounds or mixtures thereof; when the second electrode is a semi-transmission electrode or a reflection electrode, it may include Ag, Mg, Yb, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, or compounds or mixtures thereof, but is not limited thereto. The thickness of the cathode depends on the material used.

[0137] The organic electroluminescent device of the present invention may further include an encapsulation structure. The encapsulation structure may be a protective structure preventing external substances such as moisture and oxygen from entering the organic layer of the organic electroluminescent device. The encapsulation structure may be, for example, a can, such as a glass or metal can; or a thin film covering the entire surface of the organic layer.

[0138] The method for preparing the organic electroluminescent device of the present invention includes sequentially laminating an anode, a hole injection layer, a hole transport layer, an electron blocking layer, an organic film layer, an electron transport layer, an electron injection layer, and a cathode, and optionally a capping layer, onto a substrate. In this regard, methods such as vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing, or LITI can be used, but are not limited thereto. In the present invention, vacuum evaporation is preferably used to form the various layers. Those skilled in the art can conventionally select the various process conditions in the vacuum evaporation method according to actual needs.

[0139] I) Preparation of intermediates

[0140] Synthesis of intermediate J1:

[0141]

[0142] Add raw material M1 (5 mmol, 1.68 g) and cesium carbonate (12.5 mmol, 4.07 g) to a two-necked flask. Add 50 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 30 minutes. Add raw material M2 (5 mmol, 1.40 g) under nitrogen protection and stir at 140 °C for 12 hours under nitrogen protection. Filter, wash with water, dry, and pass through a column with PE:EA = 20:1 to obtain intermediate Y1.

[0143] Intermediate Y1 (5.1 mmol, 3.03 g) was dissolved in 50 mL of tetrahydrofuran (THF) solution. Under nitrogen purging at 0 °C, 3.8 mL of n-butyllithium (1.6 M) n-hexane solution was slowly added. After stirring at 0 °C for 2 hours, 10 mL of tetrahydrofuran solution of starting material M3 (5.5 mmol, 0.99 g) was slowly added. The reaction mixture was then slowly heated to room temperature and stirred overnight. Dilute hydrochloric acid solution, distilled water, and ethyl acetate were added to the reaction mixture. The aqueous layer was separated and extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate and filtered. After removing the solvent under reduced pressure, the crude product was dissolved in anhydrous dichloromethane, and then 47% boron trifluoride-diethyl ether was slowly added. The reaction mixture was stirred overnight and slowly quenched with an aqueous solution of NaHCO3. The aqueous layer was then separated and extracted with dichloromethane. The product was dried over sodium sulfate, filtered, and evaporated by rotary evaporation. The resulting product was then column chromatography to obtain intermediate J1.

[0144] Synthesis of intermediate J2:

[0145]

[0146] In a round-bottom flask, Pd(OAc)₂ (0.4 mmol, 0.08 g), Ag₂O (10 mmol, 2.32 g), NaOAc (5 mmol, 0.41 g), starting material M5 (10 mmol, 2.60 g), and starting material M4 (20 mmol, 4.26 g) were added and stirred for 16 hours at 30 °C in 100 mL of 1,3,3,3-hexafluoro-2-propanol. The resulting mixture was then diluted with EtOAc and filtered through diatomaceous earth. The mixture was washed with an appropriate amount of EtOAc, and the filtrate was evaporated to dryness under reduced pressure. The crude product was purified by column chromatography to give intermediate Y₂.

[0147] Intermediate Y2 (2.50 mmol, 0.86 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) were added to a three-necked flask and heated under nitrogen atmosphere at 110 °C for 2 hours. After cooling to room temperature, the reaction mixture was filtered through a diatomaceous earth filter, washed with chloroform, and the resulting filtrate was evaporated under vacuum. The residue was purified by silica gel column chromatography using hexane / ethyl acetate as eluent to give intermediate J2.

[0148] Synthesis of intermediate J3:

[0149]

[0150] In a round-bottom flask, Pd(OAc)₂ (0.4 mmol, 0.08 g), Ag₂O (10 mmol, 2.32 g), NaOAc (5 mmol, 0.41 g), starting material M5 (10 mmol, 2.60 g), and starting material M6 (20 mmol, 4.26 g) were added and stirred at 30 °C in 100 mL of 1,3,3,3-hexafluoro-2-propanol for 10 hours. The resulting mixture was then diluted with EtOAc and filtered through diatomaceous earth. The mixture was washed with an appropriate amount of EtOAc, and the filtrate was evaporated to dryness under reduced pressure. The crude product was purified by column chromatography to give intermediate Y3.

[0151] Intermediate Y3 (2.50 mmol, 0.86 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) were added to a three-necked flask and heated under nitrogen atmosphere at 110 °C for 2 hours. After cooling to room temperature, the reaction mixture was filtered through a diatomaceous earth filter, washed with chloroform, and the resulting filtrate was evaporated under vacuum. The residue was purified by silica gel column chromatography using hexane / ethyl acetate as eluent to give intermediate J3.

[0152] Synthesis of intermediate J4:

[0153]

[0154] In a round-bottom flask, Pd(OAc)₂ (0.4 mmol, 0.08 g), Ag₂O (10 mmol, 2.32 g), NaOAc (5 mmol, 0.41 g), starting material M5 (10 mmol, 2.60 g), and starting material M7 (20 mmol, 3.94 g) were added and stirred for 14 hours at 30 °C in 100 mL of 1,3,3,3-hexafluoro-2-propanol. The resulting mixture was then diluted with EtOAc and filtered through diatomaceous earth. The mixture was washed with an appropriate amount of EtOAc, and the filtrate was evaporated to dryness under reduced pressure. The crude product was purified by column chromatography to give intermediate Y4.

[0155] Intermediate Y4 (2.50 mmol, 0.82 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) were added to a three-necked flask and heated under nitrogen atmosphere at 110 °C for 2 hours. After cooling to room temperature, the reaction mixture was filtered through a diatomaceous earth filter, washed with chloroform, and the resulting filtrate was evaporated under vacuum. The residue was purified by silica gel column chromatography using hexane / ethyl acetate as eluent to give intermediate J4.

[0156] Synthesis of intermediate J5:

[0157]

[0158] In a round-bottom flask, Pd(OAc)₂ (0.4 mmol, 0.08 g), Ag₂O (10 mmol, 2.32 g), NaOAc (5 mmol, 0.41 g), starting material M5 (10 mmol, 2.60 g), and starting material M8 (20 mmol, 3.94 g) were added and stirred for 14 hours at 30 °C in 100 mL of 1,3,3,3-hexafluoro-2-propanol. The resulting mixture was then diluted with EtOAc and filtered through diatomaceous earth. The mixture was washed with an appropriate amount of EtOAc, and the filtrate was evaporated to dryness under reduced pressure. The crude product was purified by column chromatography to give intermediate Y5.

[0159] Intermediate Y5 (2.50 mmol, 0.82 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) were added to a three-necked flask and heated under nitrogen atmosphere at 110 °C for 2 hours. After cooling to room temperature, the reaction mixture was filtered through a diatomaceous earth filter, washed with chloroform, and the resulting filtrate was evaporated under vacuum. The residue was purified by silica gel column chromatography using hexane / ethyl acetate as eluent to give intermediate J5.

[0160] Synthesis of intermediate J6:

[0161]

[0162] Under nitrogen protection, starting material M9 (335 mmol, 50 g) was dissolved in anhydrous ACN (500 mL). The reaction system was cooled to 0 °C, and NBS (335 mmol, 59.63 g) was slowly added. After the addition was complete, the mixture was stirred for 3 hours while maintaining the temperature. The reaction was then quenched with water, extracted with ethyl acetate and washed with saturated brine, dried over anhydrous Na₂SO₄, and the solvent was evaporated. Column chromatography was used to obtain intermediate Y6.

[0163] Under nitrogen protection, intermediate Y6 (136 mmol, 31 g), starting material M10 (136 mmol, 24.2 g), and K2CO3 (408 mmol, 56.26 g) were dissolved in 1,4-Dioxane (310 mL) and water (100 mL). PdCl2 (dppf) (2.71 mmol, 1.99 g) was added, and the reaction system was reacted at 80 °C for 16 hours. After the reaction was complete, the mixture was filtered while hot, extracted with ethyl acetate and washed with saturated brine, dried over anhydrous Na2SO4, and the solvent was evaporated. Column chromatography was then used to obtain intermediate Y7.

[0164] Under nitrogen protection, intermediate Y7 (178 mmol, 50 g) was dissolved in anhydrous THF (400 mL). The reaction system was cooled to 0 °C, and a solution of concentrated hydrochloric acid (81.7 mL) in water (235 mL) was slowly added dropwise. After the addition was complete, a solution of NaNO2 (267 mmol, 18.39 g) in water (90 mL) was slowly added dropwise, maintaining the reaction temperature below 5 °C. After the addition was complete, the reaction system was stirred for 15 minutes. A solution of KI (355 mmol, 59 g) in water (371.5 mL) was added dropwise to the reaction system, maintaining the reaction temperature below 5 °C. After the addition was complete, the system was stirred for 2 hours at this temperature. The reaction was then quenched with saturated sodium sulfite solution, extracted with ethyl acetate and washed with saturated brine, dried over anhydrous Na2SO4, and the solvent was evaporated. Column chromatography was used to obtain intermediate Y8.

[0165]

[0166] In a round-bottom flask, Pd(OAc)₂ (0.4 mmol, 0.08 g), Ag₂O (10 mmol, 2.32 g), NaOAc (5 mmol, 0.41 g), intermediate Y8 (10 mmol, 3.92 g), and starting material M8 (20 mmol, 3.93 g) were added and stirred for 18 hours at 30 °C in 100 mL of 1,3,3,3-hexafluoro-2-propanol. The resulting mixture was then diluted with EtOAc and filtered through diatomaceous earth. The mixture was washed with an appropriate amount of EtOAc, and the filtrate was evaporated to dryness under reduced pressure. The crude product was purified by column chromatography to give intermediate Y9.

[0167] Intermediate Y9 (2.50 mmol, 1.15 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) were added to a three-necked flask and heated under nitrogen atmosphere at 110 °C for 3 hours. After cooling to room temperature, the reaction mixture was filtered through a diatomaceous earth filter, washed with chloroform, and the resulting filtrate was evaporated under vacuum. The residue was purified by silica gel column chromatography using hexane / ethyl acetate as eluent to give intermediate J6.

[0168] Synthesis of intermediate J7:

[0169]

[0170] In a round-bottom flask, Pd(OAc)₂ (0.4 mmol, 0.08 g), Ag₂O (10 mmol, 2.32 g), NaOAc (5 mmol, 0.41 g), starting material M11 (10 mmol, 3.14 g), and starting material M8 (20 mmol, 3.92 g) were added and stirred at 30 °C in 100 mL of 1,3,3,3-hexafluoro-2-propanol for 15 hours. The resulting mixture was then diluted with EtOAc and filtered through diatomaceous earth. The mixture was washed with an appropriate amount of EtOAc, and the filtrate was evaporated to dryness under reduced pressure. The crude product was purified by column chromatography to give intermediate Y10.

[0171] Intermediate Y10 (2.50 mmol, 0.96 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) were added to a three-necked flask and heated under nitrogen atmosphere at 110 °C for 2 hours. After cooling to room temperature, the reaction mixture was filtered through a diatomaceous earth filter, washed with chloroform, and the resulting filtrate was evaporated under vacuum. The residue was purified by silica gel column chromatography using hexane / ethyl acetate as eluent to give intermediate J7.

[0172] II) Preparation of Compounds

[0173] Example 1: Synthesis of Compound 4:

[0174]

[0175] Under nitrogen purging, intermediate J1 (11 mmol, 6.94 g) and starting material D1 (10 mmol, 2.54 g) were added to a three-necked flask and dissolved in a mixed solvent (70 mL toluene, 35 mL ethanol). Then, Pd(PPh3)4 (0.10 mmol, 0.12 g) and 15 mL of 3 mol / L K2CO3 aqueous solution were added. The mixture was heated to reflux for 12 hours under nitrogen protection. A sample was spotted onto a TLC plate to confirm complete reaction. After cooling to room temperature, the reaction mixture was filtered through a diatomaceous earth filter, washed with chloroform, and the resulting filtrate was evaporated under vacuum. The residue was purified by column chromatography on silica gel using hexane / toluene as eluent to obtain intermediate K1.

[0176] In a sealed, pressure-resistant tube under nitrogen protection, intermediate K1 (10 mmol, 6.78 g) and 90 mL of o-dichlorobenzene were added. A 2.5 M solution of tert-butyllithium in n-hexane (12 mmol, 30 mL) was added at -78 °C, the system was heated to 60 °C and reacted for 2 hours. Then, boron tribromide (15 mmol, 1.5 mL) was added at 0 °C, and the reaction was continued at room temperature for 5 hours. Next, N,N-diisopropylethylamine (20 mmol, 3.5 mL) was added at 0 °C, the system was heated to 200 °C and reacted for 10 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain compound 4. In toluene solution (1 × 10⁻⁶ g / mL) -5 The half-width at half maximum (WHM) is 30 nm. 1H NMR(400MHz,Chloroform-d)δ8.95(d,1H),8.36–8.17(m,1H),7.95(m,1H),7.84(m,3H),7.72 –7.57(m,1H),7.53–7.37(m,7H),7.31(m,2H),7.06(m,2H),6.89–6.73(m,2H),1.30(d,18H).

[0177] Example 2: Synthesis of compound 33:

[0178]

[0179] Intermediate J1 (11 mmol, 6.94 g) and intermediate J2 (10 mmol, 3.92 g) were added to a three-necked flask and dissolved in a mixed solvent (70 mL toluene, 35 mL ethanol). Then, Pd(PPh3)4 (0.10 mmol, 0.12 g) and 15 mL of 3 mol / L K2CO3 aqueous solution were added, and the mixture was heated to reflux under nitrogen protection for 13 hours. A sample was spotted onto a TLC plate to confirm the completeness of the reaction. After cooling to room temperature, the reaction mixture was filtered through a diatomaceous earth filter, washed with chloroform, and the resulting filtrate was evaporated under vacuum. The residue was purified by column chromatography on silica gel using hexane / toluene as eluent to give intermediate K2.

[0180] In a sealed, pressure-resistant tube under nitrogen protection, intermediate K2 (10 mmol, 8.17 g) and 90 mL of o-dichlorobenzene were added. A 2.5 M solution of tert-butyllithium in n-hexane (12 mmol, 30 mL) was added at -78 °C, the system was heated to 60 °C and reacted for 2 hours. Then, boron tribromide (15 mmol, 1.5 mL) was added at 0 °C, and the reaction was continued at room temperature for 5 hours. Next, N,N-diisopropylethylamine (20 mmol, 3.5 mL) was added at 0 °C, the system was heated to 200 °C and reacted for 12 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to give compound 33. In toluene solution (1 × 10⁻⁶) -5 The half-width at half maximum (WHM) is 26 nm.

[0181] Example 3: Synthesis of Compound 88:

[0182]

[0183] Intermediate J1 (11 mmol, 6.94 g) and intermediate J3 (10 mmol, 3.92 g) were added to a three-necked flask and dissolved in a mixed solvent (70 mL toluene, 35 mL ethanol). Then, Pd(PPh3)4 (0.10 mmol, 0.12 g) and 15 mL of 3 mol / L K2CO3 aqueous solution were added, and the mixture was heated to reflux under nitrogen protection for 10 hours. A sample was spotted onto a TLC plate to confirm the completeness of the reaction. After cooling to room temperature, the reaction mixture was filtered through a diatomaceous earth filter, washed with chloroform, and the resulting filtrate was evaporated under vacuum. The residue was purified by column chromatography on silica gel using hexane / toluene as the eluent to give intermediate K3.

[0184] In a sealed, pressure-resistant tube under nitrogen protection, intermediate K3 (10 mmol, 8.17 g) and 90 mL of o-dichlorobenzene were added. A 2.5 M solution of tert-butyllithium in n-hexane (12 mmol, 30 mL) was added at -78 °C, the system was heated to 60 °C and reacted for 2 hours. Then, boron tribromide (15 mmol, 1.5 mL) was added at 0 °C, and the reaction was continued at room temperature for 5 hours. Next, N,N-diisopropylethylamine (20 mmol, 3.5 mL) was added at 0 °C, the system was heated to 200 °C and reacted for 12 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to give compound 88. In toluene solution (1 × 10⁻⁶) -5 The half-width at half maximum (WHM) is 28 nm. 1 H NMR(400MHz,Chloroform-d)δ8.97(d,1H),8.34–8.19(m,1H),7.83(m,2H),7.69 (m,1H),7.55–7.24(m,12H),7.09(m,2H),6.83–6.74(m,2H),1.73–0.87(m,27H).

[0185] Example 4: Synthesis of compound 144:

[0186]

[0187] Intermediate J1 (11 mmol, 6.94 g) and intermediate J4 (10 mmol, 3.76 g) were added to a three-necked flask and dissolved in a mixed solvent (70 mL toluene, 35 mL ethanol). Then, Pd(PPh3)4 (0.10 mmol, 0.12 g) and 15 mL of 3 mol / L K2CO3 aqueous solution were added, and the mixture was heated to reflux under nitrogen protection for 13 hours. A sample was spotted onto a TLC plate to confirm complete reaction. After cooling to room temperature, the reaction mixture was filtered through a diatomaceous earth filter, washed with chloroform, and the resulting filtrate was evaporated under vacuum. The residue was purified by column chromatography on silica gel using hexane / toluene as eluent to give intermediate K4.

[0188] In a sealed, pressure-resistant tube under nitrogen protection, intermediate K4 (10 mmol, 8 g) and 90 mL of o-dichlorobenzene were added. A 2.5 M solution of tert-butyllithium in n-hexane (12 mmol, 30 mL) was added at -78 °C, the system was heated to 60 °C and reacted for 2 hours. Then, boron tribromide (15 mmol, 1.5 mL) was added at 0 °C, and the reaction was continued at room temperature for 5 hours. Next, N,N-diisopropylethylamine (20 mmol, 3.5 mL) was added at 0 °C, the system was heated to 200 °C and reacted for 12 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to give compound 144. In toluene solution (1 × 10⁻⁶), -5 The half-width at half maximum (WHM) is 26 nm.

[0189] Example 5: Synthesis of Compound 199:

[0190]

[0191] Intermediate J1 (11 mmol, 6.94 g) and intermediate J5 (10 mmol, 3.76 g) were added to a three-necked flask and dissolved in a mixed solvent (70 mL toluene, 35 mL ethanol). Then, Pd(PPh3)4 (0.10 mmol, 0.12 g) and 15 mL of 3 mol / L K2CO3 aqueous solution were added, and the mixture was heated to reflux under nitrogen protection for 13 hours. A sample was spotted onto a TLC plate to confirm complete reaction. After cooling to room temperature, the reaction mixture was filtered through a diatomaceous earth filter, washed with chloroform, and the resulting filtrate was evaporated under vacuum. The residue was purified by column chromatography on silica gel using hexane / toluene as eluent to give intermediate K5.

[0192] In a sealed, pressure-resistant tube under nitrogen protection, intermediate K5 (10 mmol, 8 g) and 90 mL of o-dichlorobenzene were added. A 2.5 M solution of tert-butyllithium in n-hexane (12 mmol, 30 mL) was added at -78 °C, the system was heated to 60 °C and reacted for 2 hours. Then, boron tribromide (15 mmol, 1.5 mL) was added at 0 °C, and the reaction was continued at room temperature for 5 hours. Next, N,N-diisopropylethylamine (20 mmol, 3.5 mL) was added at 0 °C, the system was heated to 200 °C and reacted for 12 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to give compound 199. In toluene solution (1 × 10⁻⁶) -5 The half-width at half maximum (WHM) is 28 nm. 1 H NMR(400MHz,Chloroform-d)δ8.94(d,1H),8.33–8.17(m,1H),7.85(m,2H),7.74–7.59(m,2H),7.51 –7.40(m,7H),7.37–7.23(m,3H),7.10(m,2H),7.03(d,1H),6.86–6.75(m,2H),1.66–0.86(m,27H).

[0193] Example 6: Synthesis of compound 224:

[0194]

[0195] Intermediate J1 (11 mmol, 6.94 g) and intermediate J6 (10 mmol, 5.09 g) were added to a three-necked flask and dissolved in a mixed solvent (70 mL toluene, 35 mL ethanol). Then, Pd(PPh3)4 (0.10 mmol, 0.12 g) and 15 mL of 3 mol / L K2CO3 aqueous solution were added, and the mixture was heated to reflux under nitrogen protection for 14 hours. A sample was spotted onto a TLC plate to confirm complete reaction. After cooling to room temperature, the reaction mixture was filtered through a diatomaceous earth filter, washed with chloroform, and the resulting filtrate was evaporated under vacuum. The residue was purified by column chromatography on silica gel using hexane / toluene as eluent to give intermediate K6.

[0196] In a sealed, pressure-resistant tube under nitrogen protection, intermediate K6 (10 mmol, 9.33 g) and 90 mL of o-dichlorobenzene were added. A 2.5 M solution of tert-butyllithium in n-hexane (12 mmol, 30 mL) was added at -78 °C, the system was heated to 60 °C and reacted for 2 hours. Then, boron tribromide (15 mmol, 1.5 mL) was added at 0 °C, and the reaction was continued at room temperature for 5 hours. Next, N,N-diisopropylethylamine (20 mmol, 3.5 mL) was added at 0 °C, the system was heated to 200 °C and reacted for 12 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to give compound 224. In toluene solution (1 × 10⁻⁶ g / mL) -5 The half-width at half maximum (WHM) is 28 nm. 1 H NMR(400MHz,Chloroform-d)δ8.92(d,1H),8.34–8.18(m,1H),7.81(m,2H),7.71–7.53(m,3H),7.50–7 .38(m,7H),7.36–7.19(m,5H),7.16–7.07(m,2H),7.01(d,1H),6.88–6.71(m,2H),1.84–0.95(m,36H).

[0197] Example 7: Synthesis of compound 239:

[0198]

[0199] Intermediate J1 (11 mmol, 6.94 g) and intermediate J7 (10 mmol, 4.30 g) were added to a three-necked flask and dissolved in a mixed solvent (70 mL toluene, 35 mL ethanol). Then, Pd(PPh3)4 (0.10 mmol, 0.12 g) and 15 mL of 3 mol / L K2CO3 aqueous solution were added, and the mixture was heated to reflux under nitrogen protection for 14 hours. A sample was spotted onto a TLC plate to confirm the completeness of the reaction. After cooling to room temperature, the reaction mixture was filtered through a diatomaceous earth filter, washed with chloroform, and the resulting filtrate was evaporated under vacuum. The residue was purified by column chromatography on silica gel using hexane / toluene as eluent to give intermediate K7.

[0200] In a sealed, pressure-resistant tube under nitrogen protection, intermediate K7 (10 mmol, 8.55 g) and 90 mL of o-dichlorobenzene were added. A 2.5 M solution of tert-butyllithium in n-hexane (12 mmol, 30 mL) was added at -78 °C, the system was heated to 60 °C and reacted for 2 hours. Then, boron tribromide (15 mmol, 1.5 mL) was added at 0 °C, and the reaction was continued at room temperature for 5 hours. Next, N,N-diisopropylethylamine (20 mmol, 3.5 mL) was added at 0 °C, the system was heated to 200 °C and reacted for 12 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to give compound 239. In toluene solution (1 × 10⁻⁶) -5 The half-width at half maximum (WHM) is 27 nm. 1 H NMR(400MHz,Chloroform-d)δ8.96(d,1H),8.37–8.16(m,1H),7.89(m,2H),7.58–7.23(m, 10H),7.17–7.07(m,2H),6.97(d,1H),6.87–6.76(m,2H),6.67(m,1H),1.73–1.04(m,34H).

[0201] Note: Half-width at half-maximum (FWHM) was measured using a Horiba Fluorolog-3 series fluorescence spectrometer.

[0202] The structural characterization of the compounds obtained in each embodiment is shown in Table 1.

[0203] Table 1

[0204]

[0205] The following describes in detail the application effects of the OLED materials synthesized in this invention in devices through device examples 1-7 and device comparative examples 1-2. Device examples 2-7 and device comparative examples 1-2 of this invention have the same fabrication process as device example 1, and use the same substrate and electrode materials, with consistent electrode film thickness. The only difference is the replacement of the light-emitting layer material in the device. The layer structure and test results of each device example are shown in Tables 2 and 4, respectively.

[0206] Device Example 1

[0207] like Figure 1As shown, the transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (film thickness 150nm) is washed sequentially with a cleaning agent (Semiclean M-L20), followed by washing with pure water, drying, and then ultraviolet-ozone washing to remove organic residues from the transparent ITO surface. After the above washing, HT-1 and HI-1 with a thickness of 10nm are deposited on the ITO anode layer 2 using a vacuum evaporation apparatus as a hole injection layer 3, with a mass ratio of HT-1 to HI-1 of 97:3. Next, a 60nm thick layer of HT-1 is deposited as a hole transport layer 4. Subsequently, a 30nm thick layer of EB-1 is deposited as an electron blocking layer 5. After the electron blocking materials are deposited, the light-emitting layer 6 of the OLED light-emitting device is fabricated, using GH-1 and GH-2 as the host materials and compound 4 as the dopant material, with a mass ratio of GH-1, GH-2, and compound 4 of 69:30:1. The light-emitting layer film thickness is 30nm. Following the aforementioned light-emitting layer 6, HB-1 is vacuum-deposited to a thickness of 5 nm; this layer serves as the hole-blocking layer 7. Following the hole-blocking layer 7, ET-1 and Liq are vacuum-deposited at a mass ratio of 1:1, resulting in a film thickness of 30 nm; this layer serves as the electron transport layer 8. On the electron transport layer 8, a LiF layer with a thickness of 1 nm is fabricated using a vacuum evaporation apparatus; this layer serves as the electron injection layer 9. On the electron injection layer 9, an 80 nm thick Mg:Ag electrode layer is fabricated using a vacuum evaporation apparatus, with a Mg:Ag mass ratio of 1:9; this layer serves as the cathode layer 10.

[0208] The application effects of the OLED material synthesized in this invention in devices are described in detail below through device examples 8-14 and device comparative examples 3-4. The fabrication processes of device examples 9-14 and device comparative examples 3-4 are completely identical to those of device example 8, and the same substrate and electrode materials are used, with the electrode film thickness remaining consistent. The only difference is the replacement of the light-emitting layer material in the device. The layer structures and test results of each device example are shown in Tables 3 and 4, respectively.

[0209] Device Example 8

[0210] The transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (film thickness 150nm) is washed sequentially with a cleaning agent (Semiclean M-L20), followed by washing with pure water, drying, and then ultraviolet-ozone washing to remove organic residues from the transparent ITO surface. After the above washing, a 10nm thick layer of HT-1 and HI-1 is deposited on the ITO anode layer 2 using a vacuum evaporation apparatus as a hole injection layer 3, with a mass ratio of HT-1 to HI-1 of 97:3. Next, a 60nm thick layer of HT-1 is deposited as a hole transport layer 4. Finally, a 30nm thick layer of EB-1 is deposited as an electron blocking layer 5. After the electron blocking material is deposited, the emitting layer 6 of the OLED light-emitting device is fabricated. GH-1 and GH-2 are used as the host materials, GD-1 is used as the first dopant, and compound 4 is used as the second dopant. The mass ratio of GH-1, GH-2, GD-1, and compound 4 is 66.5:30:3:0.5, and the thickness of the emitting layer is 30 nm. After the emitting layer 6, HB-1 is vacuum-deposited to a thickness of 5 nm; this layer is the hole blocking layer 7. After the hole blocking layer 7, ET-1 and Liq are vacuum-deposited to a mass ratio of 1:1, with a thickness of 30 nm; this layer is the electron transport layer 8. On the electron transport layer 8, a LiF layer with a thickness of 1 nm is fabricated using a vacuum evaporation apparatus; this layer is the electron injection layer 9. On the electron injection layer 9, a Mg:Ag electrode layer with a thickness of 80 nm is fabricated using a vacuum evaporation apparatus; the mass ratio of Mg to Ag is 1:9; this layer is used as the cathode layer 10.

[0211] The molecular structural formulas of the relevant materials are shown below:

[0212]

[0213]

[0214] After completing the OLED light-emitting device as described above, the anode and cathode are connected using a known driving circuit, and the current efficiency and lifetime of the device are measured. Examples and comparisons of devices prepared using the same method are shown in Tables 2 and 3; the test results for the current efficiency and lifetime of the obtained devices are shown in Table 4.

[0215] Table 2

[0216]

[0217]

[0218] Table 3

[0219]

[0220] Table 4

[0221]

[0222] Note: Current efficiency and emission peak were measured using an IVL (current-voltage-brightness) testing system (Suzhou Fushida Scientific Instruments Co., Ltd.); the lifetime testing system was the EAS-62C OLED device lifetime tester from System Technology Inc., Japan; LT95 refers to the time it takes for the device brightness to decay to 95%; all data are within 10 mA / cm². 2 Next test.

[0223] As can be seen from the device data results in Table 4, compared with Comparative Examples 1 and 3, the organic light-emitting device of the present invention exhibits a significant improvement in lifetime compared to OLED devices made of known materials, regardless of whether it is in a single-doped or double-doped system. When using an exciton-sensitized material as the first dopant, the device efficiency is significantly improved compared to single-doped devices. Compared with Comparative Examples 2 and 4, the organic light-emitting device of the present invention exhibits a significant improvement in lifetime compared to OLED devices made of known materials, regardless of whether it is in a single-doped or double-doped system.

[0224] In summary, the above are merely preferred embodiments of the present invention and are not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention should be included within the protection scope of the present invention.

Claims

1. A boron-containing resonance-type organic compound, characterized in that: The structure of the boron-containing resonance-type organic compound is shown in general formula (A): Each occurrence of Z is independently represented as C-(H) or C-(R0); each occurrence of R0 is independently represented as a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1 to C2 group. 10 Alkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted aromatic amino groups, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 heteroaryl, substituted or unsubstituted C2-C 30 One of the boron alkyl groups; M1 and M2 are respectively represented independently as one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiophene, or substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl. M1 and M2 are linked to other groups through carbon atoms to form a ring; The substituents used to replace the aforementioned substituted groups are optionally selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl groups, C3-C 10 cycloalkyl, C6-C 30 Aryl, C2~C 30 One or more of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

2. The boron-containing resonance-type organic compound according to claim 1, characterized in that, The structure of the boron-containing resonance organic compound is shown in general formula (1): Each occurrence of Z is independently represented as C-(H) or C-(R0); each occurrence of R0 is independently represented as a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1 to C2 group. 10 Alkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted aromatic amino groups, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 heteroaryl, substituted or unsubstituted C2-C 30 One of the boron alkyl groups; R a R b R c R d R e R f Each can be represented independently as a hydrogen atom, deuterium atom, halogen atom, cyano group, or substituted or unsubstituted C1-C. 10 Alkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted aromatic amino groups, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 heteroaryl, substituted or unsubstituted C2-C 30 One of the boron alkyl groups; M1 and M2 are respectively represented independently as one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiophene, or substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl. M1 and M2 are linked to other groups through carbon atoms to form a ring; The substituents used to replace the aforementioned substituted groups are optionally selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl groups, C3-C 10 cycloalkyl, C6-C 30 Aryl, C2~C 30 One or more of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

3. The boron-containing resonance-type organic compound according to claim 2, characterized in that, The structures of the boron-containing resonance-type organic compounds are shown in general formulas (1-1), (1-2), or (1-3): In general formulas (1-1) to (1-3), Z and R a R b R c R d R e R f Same as the limitations in general formula (1); X is represented as O or S; Each occurrence of Z1 is independently represented as C-(H) or C-(R1); each occurrence of R1 is independently represented as a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1 to C1 group. 10 Alkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted aromatic amino groups, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 heteroaryl, substituted or unsubstituted C2-C 30 One of the boroalkyl groups; any adjacent R1s can be linked to form a ring; The R m Each can be represented independently as a hydrogen atom, deuterium atom, halogen atom, cyano group, or substituted or unsubstituted C1-C. 10 Alkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted aromatic amino groups, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 heteroaryl, substituted or unsubstituted C2-C 30 One of the boron alkyl groups; The substituents used to replace the aforementioned substituted groups are optionally selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl groups, C3-C 10 cycloalkyl, C6-C 30 Aryl, C2~C 30 One or more of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

4. The boron-containing resonance-type organic compound according to claim 2, characterized in that, The structures of the boron-containing resonance organic compounds are shown in general formulas (1-4), (1-5), or (1-6): In general formulas (1-4) to (1-6), Z, M1, M2, and R... b R c R d R e R f Same as the limitation in general formula (1).

5. The boron-containing resonance-type organic compound according to claim 3, characterized in that, The structures of the boron-containing resonance-type organic compounds are shown in general formulas (1-7) or (1-8): In general formulas (1-7) and (1-8), Z, Z1, X, and R... a R c R d R e R f R m Same as the limitation in claim 3.

6. The boron-containing resonance-type organic compound according to claim 3, characterized in that, The structure of the boron-containing resonance organic compound is shown in general formula (2-1) or general formula (2-2): In general formulas (2-1) and (2-2), Z, Z1, and R... c R d R e R f Same as the limitation in claim 3; X1 is represented as O or S; Each occurrence of Z2 is independently represented as C-(H) or C-(R2); each occurrence of R2 is independently represented as a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1 to C2 group. 10 Alkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted aromatic amino groups, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 heteroaryl, substituted or unsubstituted C2-C 30 One of the boron alkyl groups; any two adjacent R2s can be linked to form a ring; The substituents used to replace the aforementioned substituted groups are optionally selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl groups, C3-C 10 cycloalkyl, C6-C 30 Aryl, C2~C 30 One or more of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

7. The boron-containing resonance-type organic compound according to claim 1, characterized in that, M1 and M2 represent substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiophene, or substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl. The R0 represents a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted diphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracene group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, or a substituted or unsubstituted quinolinyl group. Substituted or unsubstituted furanyl, substituted or unsubstituted thiophene, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amino, substituted or unsubstituted triazineyl; The substituents used for the substituent groups are selected from one or more of the following: deuterium, chlorine, fluorine, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthrene, pyridinyl, pyrazinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheneyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheninyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazoleyl, N-phenylcarbazoleyl, carbazolinyl, and azirphenanthreneyl.

8. The boron-containing resonance-type organic compound according to claim 2, characterized in that, M1 and M2 represent substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiophene, or substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl. The R a R b R c R d R e R f Each of these can be independently represented as a hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted isopropyl group, substituted or unsubstituted tert-butyl group, substituted or unsubstituted cyclohexyl group, substituted or unsubstituted adamantyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted diphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthraquinyl group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted pyridyl group, substituted or unsubstituted [unspecified] group. Quinolinyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amino, substituted or unsubstituted triazineyl; The R0 represents a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted diphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracene group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, or a substituted or unsubstituted quinolinyl group. Substituted or unsubstituted furanyl, substituted or unsubstituted thiophene, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amino, substituted or unsubstituted triazineyl; The substituents used for the substituent groups are selected from one or more of the following: deuterium, chlorine, fluorine, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthrene, pyridinyl, pyrazinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheneyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheninyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazoleyl, N-phenylcarbazoleyl, carbazolinyl, and azirphenanthreneyl.

9. The boron-containing resonance-type organic compound according to claim 3 or 5, characterized in that, The R a R b R c R d R e R f R m Each of these can be independently represented as a hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted isopropyl group, substituted or unsubstituted tert-butyl group, substituted or unsubstituted cyclohexyl group, substituted or unsubstituted adamantyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted diphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthraquinyl group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted pyridyl group, substituted or unsubstituted [unspecified] group. Quinolinyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amino, substituted or unsubstituted triazineyl; R0 and R1 are independently represented as deuterium atom, halogen atom, cyano group, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted isopropyl group, substituted or unsubstituted tert-butyl group, substituted or unsubstituted cyclohexyl group, substituted or unsubstituted adamantyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted diphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthracene group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted pyridyl group, substituted or unsubstituted Quinolinyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiophene, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amino, substituted or unsubstituted triazineyl; The substituents used for the substituent groups are selected from one or more of the following: deuterium, chlorine, fluorine, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthrene, pyridinyl, pyrazinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheneyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheninyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazoleyl, N-phenylcarbazoleyl, carbazolinyl, and azirphenanthreneyl.

10. The boron-containing resonance-type organic compound according to claim 4, characterized in that, M1 and M2 represent substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiophene, or substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl. The R b R c R d R e R f Each of these can be independently represented as a hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted isopropyl group, substituted or unsubstituted tert-butyl group, substituted or unsubstituted cyclohexyl group, substituted or unsubstituted adamantyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted diphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthraquinyl group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted pyridyl group, substituted or unsubstituted [unspecified] group. Quinolinyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amino, substituted or unsubstituted triazineyl; The R0 represents a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted diphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracene group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, or a substituted or unsubstituted quinolinyl group. Substituted or unsubstituted furanyl, substituted or unsubstituted thiophene, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amino, substituted or unsubstituted triazineyl; The substituents used for the substituent groups are selected from one or more of the following: deuterium, chlorine, fluorine, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthrene, pyridinyl, pyrazinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheneyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheninyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazoleyl, N-phenylcarbazoleyl, carbazolinyl, and azirphenanthreneyl.

11. The boron-containing resonance-type organic compound according to claim 6, characterized in that, The R c R d R e R f Each of these can be independently represented as a hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted isopropyl group, substituted or unsubstituted tert-butyl group, substituted or unsubstituted cyclohexyl group, substituted or unsubstituted adamantyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted diphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthraquinyl group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted pyridyl group, substituted or unsubstituted [unspecified] group. Quinolinyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amino, substituted or unsubstituted triazineyl; R0, R1, and R2 are independently represented as a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted diphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracene group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, and a substituted or unsubstituted phenyl group. Substituted quinolinyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amino, substituted or unsubstituted triazineyl; The substituents used for the substituent groups are selected from one or more of the following: deuterium, chlorine, fluorine, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthrene, pyridinyl, pyrazinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheneyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheninyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazoleyl, N-phenylcarbazoleyl, carbazolinyl, and azirphenanthreneyl.

12. The boron-containing resonance-type organic compound according to claim 1, characterized in that, M1 and M2 are represented as shown in the following structure: Any one of them; The range of Z is the same as that defined in general formula (1); R0 is represented as: Deuterium atom, methyl, ethyl, isopropyl, tert-butyl, cyano Any one of them.

13. The boron-containing resonance-type organic compound according to claim 2, characterized in that, M1 and M2 are represented as shown in the following structure: Any one of them; The range of Z is the same as that defined in general formula (1); The R a R b R c R d R e R f Each can be represented independently as: Hydrogen atom, deuterium atom, methyl, ethyl, isopropyl, tert-butyl, cyano Any one of them; R0 is represented as: Deuterium atom, methyl, ethyl, isopropyl, tert-butyl, cyano Any one of them.

14. The boron-containing resonance-type organic compound according to claim 3 or 5, characterized in that, The R a R b R c R d R e R f R m Each can be represented independently as: Hydrogen atom, deuterium atom, methyl, ethyl, isopropyl, tert-butyl, cyano Any one of them; R0 and R1 are independently represented as follows: Deuterium atom, methyl, ethyl, isopropyl, tert-butyl, cyano Any one of them.

15. The boron-containing resonance-type organic compound according to claim 4, characterized in that, M1 and M2 are represented as shown in the following structure: Any one of them; The range of Z is the same as that defined in general formula (1); The R a R b R c R d R e R f Each can be represented independently as: Hydrogen atom, deuterium atom, methyl, ethyl, isopropyl, tert-butyl, cyano Any one of them; R0 is represented as: Deuterium atom, methyl, ethyl, isopropyl, tert-butyl, cyano Any one of them.

16. The boron-containing resonance-type organic compound according to claim 6, characterized in that, The R c R d R e R f Each can be represented independently as: Hydrogen atom, deuterium atom, methyl, ethyl, isopropyl, tert-butyl, cyano Any one of them; R0, R1, and R2 are each independently represented as follows: Deuterium atom, methyl, ethyl, isopropyl, tert-butyl, cyano Any one of them.

17. The boron-containing resonance-type organic compound according to claim 1, characterized in that: The specific structural formula of the boron-containing resonance-type organic compound is any one of the following structures:

18. An organic light-emitting device, comprising a substrate, a first electrode, a second electrode, and a functional layer, wherein the functional layer is located between the first electrode and the second electrode, characterized in that: The functional layer comprises the boron-containing resonance-type organic compound according to any one of claims 1-17; The functional layer includes a light-emitting layer, which comprises a host material and a dopant material, wherein the dopant material is a boron-containing resonant organic compound as described in any one of claims 1-17.

19. The organic light-emitting device according to claim 18, characterized in that, The functional layer includes a light-emitting layer, which comprises a first host material, a second host material, and a dopant material. At least one of the first host material and the second host material is a TADF material, and the dopant material is a boron-containing resonant organic compound as described in any one of claims 1-17.

20. The organic light-emitting device according to claim 18, wherein the functional layer comprises a light-emitting layer, the light-emitting layer comprises a host material, an exciton-sensitizing material and a dopant material, the exciton-sensitizing material is a complex containing a metal element, and the dopant material is a boron-containing resonant organic compound according to any one of claims 1-17.

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