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 compounds and the organic electroluminescent device comprising it, belong to semiconductor material technical field, the present application provides the structure of boron-containing resonance type organic compound as shown in general formula 1: The present application boron-containing resonance type organic compound is used as the doping material in the light-emitting layer material of organic electroluminescent device, can be used as the green light doping material of the light-emitting layer of organic electroluminescent device, so as to improve the luminous efficiency and life of device.

Description

Technical Field

[0001] This invention relates to the field of semiconductor materials technology, and in particular 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 iterative development. 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 performance requirements, the new generation display standard (BT.2020) is driving the development of organic electroluminescent materials towards higher color purity, which necessitates that the core light-emitting material 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. In addition, green phosphorescence naturally has a high shoulder peak, making it relatively difficult to improve the color gamut display under traditional device structures. Therefore, developing a new generation of high color purity green organic electroluminescent 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 reported successively. Furthermore, several papers on green boron-nitrogen narrow-emission materials and device effects were reported in 2022 and 2023, such as: DOI: 10.1002 / anie.202301930, DOI: 10.1038 / s41566-022-01106-8, DOI: 10.1002 / anie.202313254, DOI: 10.1038 / s41566-022-01083-y, DOI: 10.1002 / anie.202202380, etc., demonstrating the high color purity and efficiency of these materials, which have great potential as a new generation of green organic electroluminescent display materials. 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 fully utilizes triplet excitons and transfers energy to fluorescent doping materials through energy transfer, achieving 100% in-device quantum efficiency (DOI: 10.1038 / ncomms5016, DOI: 10.1038 / s41566-022-00958-4). This technology can compensate for the insufficient exciton utilization of fluorescent doping materials and effectively leverage the high fluorescence quantum yield, high device stability, high color purity, and low cost of fluorescent doping materials, showing broad prospects for OLED applications. For example, CN 107507921A and CN 110492006A 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; CN 110492005A and CN 110492009A disclose a light-emitting layer combination scheme using excitocomplexes as the main body and boron-containing materials as dopants; both can achieve efficiencies comparable to phosphorescence and relatively narrow half-width at half-maximum (HWHM). Therefore, developing sensitization technology 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 containing the same. The compound of this invention can achieve green light emission.

[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 1:

[0007]

[0008] In general formula 1, M1 and M2 are independently represented as C6 to C6 molecules substituted or unsubstituted by one or more R molecules. 30 The aromatic ring, C2-C2 with or without one or more R-substituted or unsubstituted R-substituted rings. 30 Heteroaromatic rings, C6-C6 substituted or unsubstituted with one or more R groups. 30 The aliphatic ring, C formed by the fusion of two or more aromatic rings, heteroaromatic rings, or aliphatic rings, substituted or unsubstituted with one or more Rs. 10 ~C 30 One type of fused ring;

[0009] The presence of R, whether the same or different, indicates a deuterium atom, a halogen atom, a cyano group, or C1-C1 atoms that are substituted or unsubstituted. 10Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, borane alkyl group substituted or unsubstituted, and silane alkyl group substituted or unsubstituted;

[0010] The replacement of R is either a single bond or a parallel ring connection;

[0011] R1, R2, and R3 are independently represented as hydrogen atom, deuterium atom, halogen atom, cyano group, and C1-C1 atoms substituted or unsubstituted with substituents, respectively. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, borane alkyl group substituted or unsubstituted, and silane alkyl group substituted or unsubstituted;

[0012] Ar1, Ar2, Ar3, and Ar4 are independently represented as hydrogen atoms, deuterium atoms, halogen atoms, and C1-C1 atoms with or without substituents, respectively. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30One of heteroaryl, substituted or unsubstituted boronyl groups;

[0013] Ar1 and Ar2 are either not connected or connected in a ring;

[0014] Ar3 and Ar4 are either not connected or connected in a ring;

[0015] When Ar1 and Ar2, and Ar3 and Ar4 are simultaneously connected to form a ring, Ar4 and R1 are connected through... Connect them into a ring;

[0016] Z1 and Z2 are independently represented as hydrogen atom, deuterium atom, halogen atom, and C1-C1 atoms substituted or unsubstituted, respectively. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted boronyl groups;

[0017] When Z appears the same or different each time, it is represented as C-(H) or C-(R0);

[0018] R0 represents a deuterium atom, a halogen atom, a cyano group, or a C1-C1 group that is substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, borane alkyl group substituted or unsubstituted, and silane alkyl group substituted or unsubstituted;

[0019] The substituents are selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups;

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

[0021] Furthermore, the structure of the boron-containing resonance organic compound is shown in general formula 1-1 or general formula 1-2:

[0022]

[0023] In General Formulas 1-1 and 1-2, the meanings of M1, Ar1, Ar2, Ar3, Ar4, Z, R1, R2, and R3 are the same as those defined in General Formula 1 above.

[0024] Furthermore, the structure of the boron-containing resonance organic compound is shown in general formula 2-1 or general formula 2-2:

[0025]

[0026] In general formulas 2-1 and 2-2, the meanings of M1, M2, Ar1, Ar2, Ar3, Ar4, Z, Z1, and Z2 are the same as those defined in general formula 1 above;

[0027] M3 represents C6-C6 substituted or unsubstituted with one or more R groups. 30 The aromatic ring, C2-C2 with or without one or more R-substituted or unsubstituted R-substituted rings. 30 Heteroaromatic rings, C6-C6 substituted or unsubstituted with one or more R groups. 30 The aliphatic ring, C formed by the fusion of two or more aromatic rings, heteroaromatic rings, or aliphatic rings, substituted or unsubstituted with one or more Rs. 10 ~C 30 One type of fused ring;

[0028] The presence of R, whether the same or different, indicates a deuterium atom, a halogen atom, a cyano group, or C1-C1 atoms that are substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, borane alkyl group substituted or unsubstituted, and silane alkyl group substituted or unsubstituted;

[0029] The replacement of R is either a single bond or a parallel ring connection;

[0030] The substituents are selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups;

[0031] The heteroaryl group and the heteroatom in the heteroaryl ring are selected from one or more of O, S, N, Si, and B;

[0032] Preferably, the structure of the boron-containing resonance organic compound is shown in any one of general formulas 2-3 to 2-11:

[0033]

[0034]

[0035] In general formulas 2-3 to 2-11, the meanings of M1, Ar1, Ar2, Ar3, Ar4, Z, Z1, and Z2 are the same as those defined in general formula 1 above;

[0036] M3 represents C6-C6 substituted or unsubstituted with one or more R groups. 30 The aromatic ring, C2-C2 with or without one or more R-substituted or unsubstituted R-substituted rings. 30 Heteroaromatic rings, C6-C6 substituted or unsubstituted with one or more R groups. 30 The aliphatic ring, C formed by the fusion of two or more aromatic rings, heteroaromatic rings, or aliphatic rings, substituted or unsubstituted with one or more Rs. 10 ~C 30 One type of fused ring;

[0037] The presence of R, whether the same or different, indicates a deuterium atom, a halogen atom, a cyano group, or C1-C1 atoms that are substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, borane alkyl group substituted or unsubstituted, and silane alkyl group substituted or unsubstituted;

[0038] The replacement of R is either a single bond or a parallel ring connection;

[0039] The substituents are selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups;

[0040] The heteroaryl group and the heteroatom in the heteroaryl ring are selected from one or more of O, S, N, Si, and B;

[0041] Furthermore, the structure of the boron-containing resonance organic compound is shown in any one of general formulas 3-1 to 3-15:

[0042]

[0043]

[0044] In formulas 3-1 to 3-15, the meanings of Ar1, Ar2, Ar3, Ar4, Z, Z1, and Z2 are the same as those defined in formula 1 above; preferably, the structure of the boron-containing resonance organic compound is shown in any one of formulas (4-1) to (4-6):

[0045]

[0046]

[0047] In general formulas (4-1) to (4-6), the meaning of Z is the same as that defined in general formula 1 above.

[0048] Furthermore, the structure of the boron-containing resonance organic compound is shown in any one of general formulas 5-1 to 5-4:

[0049]

[0050] In general formulas 5-1 to 5-4, the meanings of Ar1, Ar2, Ar3, Ar4, R1, R2, R3, Z1, and Z2 are the same as those defined in general formula 1 above;

[0051] The R4, R5, R6, R7, R8, R9, R 10 Each of the following can be represented independently as a hydrogen atom, deuterium atom, halogen atom, cyano group, or C1-C1 atoms substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, borane alkyl group substituted or unsubstituted, and silane alkyl group substituted or unsubstituted;

[0052] The m7 is represented as 0, 1, 2, 3, 4 or 5;

[0053] The m4, m5, m6, m8, m 10 Each can be independently represented as 0, 1, 2, 3, or 4;

[0054] The m9, m 11 Each can be independently represented as 0, 1, 2, or 3;

[0055] The substituents are selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups;

[0056] The heteroaryl group and the heteroatom in the heteroaryl ring are selected from one or more of O, S, N, Si, and B;

[0057] Preferably, the structure of the boron-containing resonance organic compound is as shown in any one of general formulas 5-5 to 5-8:

[0058]

[0059] In general formulas 5-5 to 5-8, the meanings of Ar1, Ar2, Ar3, Ar4, R1, R2, R3, Z1, and Z2 are the same as those defined in general formula 1 above;

[0060] The R4, R5, R6, R7, R8, R9, R 10 Each of the following can be represented independently as a hydrogen atom, deuterium atom, halogen atom, cyano group, or C1-C1 atoms substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, borane alkyl group substituted or unsubstituted, and silane alkyl group substituted or unsubstituted;

[0061] The m7 is represented as 0, 1, 2, 3, 4 or 5;

[0062] The m4, m8, m 10 Each can be independently represented as 0, 1, 2, 3, or 4;

[0063] The substituents are selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups;

[0064] The heteroaryl group and the heteroatom in the heteroaryl ring are selected from one or more of O, S, N, Si, and B;

[0065] Further, M1, M2, and M3 represent any one of the following groups substituted or unsubstituted by one or more R groups: phenyl, naphthyl, anthraceneyl, phenanthryl, pyridyl, quinolinyl, furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, indole[3,2,1-jk]carbazoyl, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, and spirofluorenyl;

[0066] R and RO represent a deuterium atom, a halogen atom, a cyano group, a methyl group (substituted or unsubstituted), an ethyl group (substituted or unsubstituted), an isopropyl group (substituted or unsubstituted), a tert-butyl group (substituted or unsubstituted), a cyclohexyl group (substituted or unsubstituted), a cyclopentyl group (substituted or unsubstituted), an adamantyl group (substituted or unsubstituted), a phenyl group (substituted or unsubstituted), a diphenyl group (substituted or unsubstituted), a terphenyl group (substituted or unsubstituted), a naphthyl group (substituted or unsubstituted), anthracene group (substituted or unsubstituted), a phenanthryl group (substituted or unsubstituted), a pyridyl group (substituted or unsubstituted), a quinolinyl group (substituted or unsubstituted), and a furanyl group (substituted or unsubstituted). Thiophene group substituted or unsubstituted, benzofuran group substituted or unsubstituted, benzothiophene group substituted or unsubstituted, dibenzofuran group substituted or unsubstituted, dibenzothiophene group substituted or unsubstituted, carbazolyl group substituted or unsubstituted, 9,9-dimethylfluorenyl group substituted or unsubstituted, 9,9-diphenylfluorenyl group substituted or unsubstituted, spirofluorenyl group substituted or unsubstituted, triazine group substituted or unsubstituted, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl group substituted or unsubstituted, diphenylamino group substituted or unsubstituted, indole group substituted or unsubstituted, benzoindole group substituted or unsubstituted;

[0067] The R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10Represented as deuterium atom, halogen atom, cyano group, 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), cyclopentyl 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 group (substituted or unsubstituted), furanyl group (substituted or unsubstituted), etc. Substituted or unsubstituted thiophene group, substituted or unsubstituted benzofuran group, substituted or unsubstituted benzothiophene group, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted dibenzothiophene group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted 9,9-dimethylfluorenyl group, substituted or unsubstituted 9,9-diphenylfluorenyl group, substituted or unsubstituted spirofluorenyl group, substituted or unsubstituted triazine group, substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl group, substituted or unsubstituted diphenylamino group, substituted or unsubstituted indole group, substituted or unsubstituted benzoindole group;

[0068] Ar1, Ar2, Ar3, Ar4, Z1, and Z2 are independently represented as hydrogen atom, deuterium atom, halogen atom, cyano group, 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), cyclopentyl 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 group (substituted or unsubstituted), and so on. Substituent-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 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted triazineyl, substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, substituted or unsubstituted diphenylamino, substituted or unsubstituted indoleyl, substituted or unsubstituted benzoindoleyl;

[0069] The substituents are selected from one or more of the following: deuterium, chlorine, fluorine, trifluoromethyl, 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, indoleyl, pyrroleyl, dibenzofuranyl, dibenzothiapheneyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazolyl, N-phenylcarbazolyl, carbazolinyl, azirphenanthreneyl, diphenylamino, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, and benzoindoleyl.

[0070] Furthermore, the specific structural formula of the boron-containing resonance organic compound is any one of the following structures:

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088] The present invention also provides an organic light-emitting device comprising a substrate, a first electrode, an organic functional material layer, and a second electrode, wherein the first electrode is located on the substrate, the organic functional material layer is located on the first electrode, and the second electrode is located on the functional layer, and the organic functional material layer contains the boron-containing resonant organic compound of the present invention.

[0089] Furthermore, the organic functional material 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 of the present invention.

[0090] Preferably, the light-emitting layer comprises a first host material, a second host material, and a dopant material, wherein 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 this invention.

[0091] Furthermore, the light-emitting layer comprises a host material, an exciton-sensitizing material, and a dopant material, characterized in that: the exciton-sensitizing material is a complex containing a metal element, and the dopant material is the boron-containing organic compound described in this invention.

[0092] Compared with the prior art, the beneficial technical effects of the present invention are as follows:

[0093] (1) The compound of the present invention can be used in organic electroluminescent devices as a doping material for the light-emitting layer. It can emit green fluorescence under the action of an electric field and can be applied in the fields of OLED lighting or OLED display.

[0094] (2) The compounds of the present invention have a narrower FWHM spectrum, which can effectively improve the color gamut of the device.

[0095] (3) The compound of the present invention, as a green light doping material, can significantly improve device efficiency and device lifetime. Attached Figure Description

[0096] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device using the materials listed in this invention;

[0097] 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

[0098] The present invention will now be described in detail with reference to the accompanying drawings and embodiments.

[0099] 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.

[0100] In this invention, the linking into rings refers to linking into aromatic rings, heteroaromatic rings, or aliphatic rings, preferably linking into C6-C6 rings. 30 Aromatic rings, C2-C 30 heterocyclic aromatic rings or C6-C 30 Aliphatic rings are preferably linked by single bonds, double bonds, -O-, -S-, -N(R'1)-, -C(R'2)(R'3)-, -Si(R'4)(R'5)- or -C(R'6)=C(R'7)-, and are preferably linked by substituted or unsubstituted benzene rings, substituted or unsubstituted naphthalene rings, or substituted or unsubstituted cyclohexane;

[0101] R'1, R'2, R'3, R'4, R'5, R'6, and R'7 are independently represented as C1 to C2 groups, substituted or unsubstituted. 10Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C6-C6 with or without substituents 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0102] R'2 and R'3 are not connected or are linked by single bonds, double bonds, -O-, -S-, -N(ph)-, dimethyl-substituted methylene, or diphenyl-substituted methylene to form a ring.

[0103] R'4 and R'5 are not connected or are linked by single bonds, double bonds, -O-, -S-, -N(ph)-, dimethyl-substituted methylene, or diphenyl-substituted methylene to form a ring.

[0104] R'6 and R'7 are not connected or are linked by single bonds, double bonds, -O-, -S-, -N(ph)-, dimethyl-substituted methylene, or diphenyl-substituted methylene to form a ring.

[0105] In this invention, the substituted or unsubstituted aromatic amino group refers to... Wherein Q1 and Q2 represent aromatic groups that are substituted or unsubstituted, and Q1 and Q2 preferably represent C6-C6 groups that are substituted or unsubstituted. 30 The aryl group may be substituted or unsubstituted at C2-C2. 30 Mixed aromatic compounds.

[0106] In this invention, C6 to C6 are substituted or unsubstituted. 30 Aryl refers to an aryl group with 6 to 30 carbon atoms, substituted or unsubstituted, preferably an aryl group with 6 to 20 carbon atoms, preferably an aryl group with 6 to 18 carbon atoms, preferably an aryl group with 6 to 10 carbon atoms, preferably substituted or unsubstituted phenyl, naphthyl, anthracene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirofluorenyl, phenanthyl, fused tetraphenyl, pyrene, diphenyl, terphenyl, etc. The following are examples of compounds: triphenylene, perylene, indene, and 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, but not limited to these.

[0107] In this invention, C6~C 30 Aryl refers to an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, more preferably an aryl group having 6 to 18 carbon atoms, and more preferably an aryl group having 6 to 10 carbon atoms. Other preferred aryl groups include phenyl, naphthyl, anthraceneyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirofluorenyl, phenanthryl, tetraphenyl, pyrene, diphenyl, and terphenyl. The compounds include, but are not limited to, triphenyl, peryl, indole, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl.

[0108] In this invention, deuterium-substituted C6-C 30 The aryl group refers to a deuterated aryl group with 6 to 30 carbon atoms, preferably a deuterated aryl group with 6 to 20 carbon atoms, preferably a deuterated aryl group with 6 to 18 carbon atoms, preferably a deuterated aryl group with 6 to 10 carbon atoms, and preferably a deuterated phenyl, deuterated naphthyl, deuterated anthracene, deuterated fluorenyl, deuterated dimethylfluorenyl, deuterated diphenylfluorenyl, deuterated spirofluorenyl, deuterated phenanthrene, deuterated tetraphenyl, deuterated pyrene, deuterated diphenyl, deuterated terphenyl, and deuterated... The compounds include, but are not limited to, deuterated triphenyl, deuterated peryl, deuterated indyl, and deuterated 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl.

[0109] In this invention, C2 to C3 are substituted or unsubstituted. 30A heteroaryl group refers to a heteroaryl group having 2 to 30 carbon atoms, either substituted or unsubstituted, preferably a heteroaryl group having 2 to 20 carbon atoms, preferably a heteroaryl group having 4 to 20 carbon atoms, preferably a heteroaryl group having 4 to 10 carbon atoms, preferably a heteroaryl group having 5 to 10 carbon atoms, preferably a heteroaryl group having 6 to 12 carbon atoms, and preferably a furan with substituted or unsubstituted carbon atoms. Thiophene group (substituted or unsubstituted), pyrrole group (substituted or unsubstituted), pyrazol group (substituted or unsubstituted), imidazo group (substituted or unsubstituted), triazol group (substituted or unsubstituted), oxazol group (substituted or unsubstituted), thiazolyl group (substituted or unsubstituted), oxadiazol group (substituted or unsubstituted), thiadiazol group (substituted or unsubstituted), pyridinyl group (substituted or unsubstituted), pyrimidinyl group (substituted or unsubstituted), pyrazine group (substituted or unsubstituted). Triazine group (substituted or unsubstituted), benzofuran group (substituted or unsubstituted), benzothiophene group (substituted or unsubstituted), benzimidazolyl group (substituted or unsubstituted), indolyl group (substituted or unsubstituted), quinolinyl group (substituted or unsubstituted), isoquinolinyl group (substituted or unsubstituted), quinazolinyl group (substituted or unsubstituted), quinolinyl group (substituted or unsubstituted), naphthidyl group (substituted or unsubstituted), benzoxazine group (substituted or unsubstituted), and others. The following are examples of substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridineyl, substituted or unsubstituted benzinyl, substituted or unsubstituted benzithiazinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted furanyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted benzoindolyl, but not limited to these.

[0110] In this invention, C2~C 30Heteroaryl refers to heteroaryl groups with 2 to 30 carbon atoms, preferably heteroaryl groups with 2 to 20 carbon atoms, more preferably heteroaryl groups with 4 to 20 carbon atoms, more preferably heteroaryl groups with 4 to 10 carbon atoms, more preferably heteroaryl groups with 6 to 12 carbon atoms, and preferably furanyl, thiophene, pyrrole, pyrazolyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, pyridazolyl, etc. The following are not limited to: pyridyl, pyrazinyl, triazinyl, benzofuranyl, benzothiophenyl, benzoimidazolyl, indolyl, quinolinyl, isoquinolinyl, quinazolinyl, quinolinyl, naphridyl, benzooxazinyl, benzothiazinyl, acridineyl, benazinoyl, benazinoyl, benazinoyl, benazinoyl, fumonyl, dibenzofuranyl, dibenzothiaphenyl, carbazoleyl, N-phenylcarbazoleyl, benzoindolyl.

[0111] In this invention, deuterium-substituted C2-C 30 The heteroaryl group refers to a heteroaryl group with 5 to 30 deuterated carbon atoms, preferably a heteroaryl group with 5 to 20 deuterated carbon atoms, preferably a heteroaryl group with 5 to 10 deuterated carbon atoms, preferably a heteroaryl group with 6 to 12 deuterated carbon atoms, preferably deuterated furanyl, deuterated thiophene, deuterated pyrrole, deuterated pyrazolyl, deuterated imidazolyl, deuterated triazolyl, deuterated oxazolyl, deuterated thiazolyl, deuterated oxadiazolyl, deuterated thiadiazolyl, deuterated pyridyl, deuterated pyrimidinyl, deuterated pyrazinyl, deuterated triazine, and deuterated... Substituted benzofuranyl, deuterated benzothiophenyl, deuterated benzimidazolyl, deuterated indolyl, deuterated quinolinyl, deuterated isoquinolinyl, deuterated quinazolinyl, deuterated quinolinyl, deuterated naphthidyl, deuterated benzoxazinyl, deuterated benzothiazinyl, deuterated acridineyl, deuterated benzazinyl, deuterated benzthiazinyl, deuterated benzoxazinyl, deuterated fumonyl, deuterated dibenzofuranyl, deuterated dibenzothiaphenyl, deuterated carbazoyl, deuterated substituted N-phenylcarbazoyl, deuterated benzoindolyl, but not limited to these.

[0112] In this invention, the number of heteroatoms in the heteroaryl group is 1-5, preferably 1-4, preferably 1-3, preferably 1-2, and preferably 1.

[0113] The C1-C1 components of this invention, whether substituted or unsubstituted, are... 10Alkyl groups (including straight-chain alkyl and branched-chain alkyl) refer to alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted, preferably alkyl groups having 1 to 7 carbon atoms, preferably alkyl groups having 1 to 5 carbon atoms, preferably alkyl groups having 1 to 4 carbon atoms, preferably methyl, ethyl, propyl, isopropyl, butyl, etc., substituted or unsubstituted. Tert-butyl, isobutyl with or without a substituent, sec-butyl with or without a substituent, neopentyl with or without a substituent, n-pentyl with or without a substituent, isopentyl with or without a substituent, octyl with or without a substituent, heptyl with or without a substituent, n-decyl with or without a substituent, 1-methylpentyl with or without a substituent, 2-methylpentyl with or without a substituent, 3-methylpentyl with or without a substituent, 1-butylpentyl with or without a substituent, etc., but not limited to these.

[0114] The C1 to C of this invention 10 Alkyl (including straight-chain alkyl and branched-chain alkyl) refers to an alkyl group having 1 to 10 carbon atoms, preferably an alkyl group having 1 to 7 carbon atoms, preferably an alkyl group having 1 to 5 carbon atoms, preferably an alkyl group having 1 to 4 carbon atoms, preferably 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 not limited to these.

[0115] The deuterium-substituted C1-C of the present invention 10 Alkyl (including straight-chain alkyl and branched-chain alkyl) refers to a deuterated alkyl group having 1 to 10 carbon atoms, preferably a deuterated alkyl group having 1 to 7 carbon atoms, preferably a deuterated alkyl group having 1 to 5 carbon atoms, preferably a deuterated alkyl group having 1 to 4 carbon atoms, preferably deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated butyl, deuterated tert-butyl, deuterated isobutyl, deuterated sec-butyl, deuterated neopentyl, deuterated n-pentyl, deuterated isopentyl, deuterated octyl, deuterated heptyl, deuterated n-decyl, deuterated 1-methylpentyl, deuterated 2-methylpentyl, deuterated 3-methylpentyl, deuterated 1-butylpentyl, etc., but not limited to these.

[0116] The C3-C3 groups described in this invention, whether substituted or unsubstituted, are... 10Cycloalkyl groups are preferably C4-C9 cycloalkyl groups, substituted or unsubstituted, and more preferably C5-C9 cycloalkyl groups, substituted or unsubstituted. 10 Cycloalkyl groups, non-limiting examples of which may include, but are not limited to, cyclopropyl groups substituted or unsubstituted with substituents, cyclobutyl groups substituted or unsubstituted with substituents, cyclopentyl groups substituted or unsubstituted with substituents, cyclohexyl groups substituted or unsubstituted with substituents, 4-methylcyclohexyl groups substituted or unsubstituted with substituents, 4,4-dimethylcyclohexyl groups substituted or unsubstituted with substituents, adamantyl groups substituted or unsubstituted with substituents, and cycloheptyl groups substituted or unsubstituted with substituents.

[0117] The C3~C of this invention 10 Cycloalkyl groups are preferably C4-C9 cycloalkyl groups, more preferably C5-C9 cycloalkyl groups. 10 Cycloalkyl groups, non-limiting examples of which may include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl and cycloheptyl.

[0118] The deuterium-substituted C3-C of the present invention 10 The cycloalkyl group is preferably a deuterated C4-C9 cycloalkyl group, more preferably a deuterated C5-C9 cycloalkyl group. 10 Cycloalkyl groups, non-limiting examples of which may include, but are not limited to, deuterated cyclopropyl, deuterated cyclobutyl, deuterated cyclopentyl, deuterated cyclohexyl, deuterated 4-methylcyclohexyl, deuterated 4,4-dimethylcyclohexyl, deuterated adamantyl and deuterated cycloheptyl.

[0119] The halogen atom mentioned in this invention refers to a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0120] 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.

[0121] In this invention, the substituents used for the substituent groups are selected from deuterium, cyano, adamantyl, methyl, ethyl, n-propyl, isopropyl, tert-amyl, tert-butyl, n-butyl, isobutyl, sec-butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthrene, furanyl, thiophene, indole, pyrrole, dibenzofuranyl, dibenzothiophene, 9,9-dimethylfluorenyl, spirofluorenyl, carbazole, N-phenylcarbazole, diphenylamino, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, and methyl-substituted benzene. One or more of the following: methyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, adamantyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, and deuterated tert-butyl-substituted diphenyl.

[0122] 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 glass substrate is preferred. There are no particular limitations on the thickness of the substrate.

[0123] 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, typically 50-500 nm, preferably 70-300 nm, and more preferably 100-200 nm.

[0124] 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.

[0125] 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.

[0126] 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.

[0127] 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.

[0128] 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.

[0129] Preferably, the main organic material used as the hole injection layer of the present invention may be selected from the following prior art:

[0130] The compounds disclosed in JP1996048656A, CN1702065A, CN101535256A, CN103108859A, US20120112176A1, JP1989142657A, and CN105439999A, but not limited thereto.

[0131] 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.

[0132] 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.

[0133] 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 meter.

[0134] 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.

[0135] Preferably, the hole transport layer material of the present invention may be selected from the compounds disclosed in the prior art:

[0136]

[0137] 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.

[0138] 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.

[0139] In one embodiment of the present invention, the electron blocking layer material may be selected from the compounds disclosed in the prior art:

[0140]

[0141]

[0142] 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.

[0143] 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.

[0144] The light-emitting layer may comprise 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 Formula 1 of the present invention.

[0145] The light-emitting layer can contain a single-substrate material or a dual-substrate material;

[0146] 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;

[0147] 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.

[0148] The light-emitting layer may include a host material, an exciton-sensitizing material, and a dopant material;

[0149] 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.

[0150] 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.

[0151] 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.

[0152] 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.

[0153] 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:

[0154]

[0155] 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.

[0156] 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:

[0157]

[0158] 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.

[0159] 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.

[0160] 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.

[0161] 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.

[0162] 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, BaF2, 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, Mo, Ti, or mixtures thereof, but is not limited thereto. The thickness of the cathode depends on the material used.

[0163] 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.

[0164] 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, a light-emitting layer, a hole blocking 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.

[0165] Synthesis Examples

[0166] All raw materials involved in the synthesis embodiments of the present invention can be purchased from the market or obtained by conventional preparation methods in the art;

[0167] Synthesis of intermediate C-1:

[0168]

[0169] Add raw material B-1 (25 mmol, 10.07 g), potassium carbonate (62.5 mmol, 8.64 g), tricyclohexylphosphine (1.25 mmol, 0.35 g), and palladium acetate (0.4 mmol, 0.09 g) to a two-necked flask. Add 100 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 36 minutes. Add raw material A-1 (25 mmol, 6.73 g) under nitrogen protection and stir at 145 °C for 13 hours under nitrogen protection. Filter, wash with water, dry, and pass through a column to obtain intermediate C-1.

[0170] Synthesis of intermediate C-2:

[0171]

[0172] The synthesis of intermediate C-2 is similar to that of intermediate C-1, except that raw material B-2 is used instead of raw material B-1.

[0173] Synthesis of intermediate C-3:

[0174]

[0175] Starting material A-3 (10 mmol, 3.22 g) was dissolved in 120 mL of tetrahydrofuran (THF) solution. Under nitrogen purging at -78 °C, 4.7 mL of n-butyllithium (2.5 M, 11.7 mmol) n-hexane solution was slowly added. After stirring at -78 °C for 7.5 hours, 30 mL of tetrahydrofuran solution of starting material B-3 (10 mmol, 1.80 g) was slowly added. The reaction mixture was then slowly heated to room temperature and stirred overnight. 30 mL of dilute hydrochloric acid (1.0 M), 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 then slowly quenched with an aqueous sodium bicarbonate (NaHCO3) solution. Next, the aqueous layer was separated, extracted with dichloromethane, dried with sodium sulfate, filtered, distilled under reduced pressure, and passed through a column to obtain intermediate C-3.

[0176] Synthesis of intermediate C-4:

[0177]

[0178] The synthesis of intermediate C-4 is similar to that of intermediate C-3, except that raw material B-3 is replaced by raw material B-4.

[0179] Synthesis of intermediate C-5:

[0180]

[0181] The synthesis of intermediate C-5 is similar to that of intermediate C-3, except that raw material A-5 is used instead of raw material A-3.

[0182] Synthesis of intermediates C-6 and D-6:

[0183]

[0184] Add raw material B-2 (25 mmol, 7.26 g), potassium carbonate (62.5 mmol, 8.6 g), tricyclohexylphosphine (1.25 mmol, 0.35 g), and palladium acetate (0.4 mmol, 90 mg) to a two-necked flask. Add 100 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 1.5 hours. Add raw material A-6 (25 mmol, 8.29 g) under nitrogen protection and stir at 140 °C for 16 hours under nitrogen protection. Filter, wash with water, dry, and pass through a column to obtain intermediates C-6 and D-6.

[0185] Synthesis of intermediates C-7 and D-7:

[0186]

[0187] The synthesis of intermediates C-7 and D-7 is the same as that of intermediates C-6 and D-6, except that raw material A-7 is used to replace raw material A-6 and raw material B-7 is used to replace raw material B-2.

[0188] Synthesis of compound 87:

[0189]

[0190] Add raw material E-1 (20 mmol, 4.98 g) and cesium carbonate (55.2 mmol, 17.99 g) to a two-necked flask. Add 220 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 40 minutes. Add intermediate C-1 (20 mmol, 10.88 g) under nitrogen protection. Reflux the solution under magnetic stirring for 40 hours. Cool, filter, wash with water, dry, and pass through a column to obtain intermediate F-1.

[0191] Intermediate F-1 (15 mmol, 11.59 g) and cesium carbonate (30 mmol, 9.77 g) were added to a two-necked flask. Under nitrogen protection, 120 mL of anhydrous DMF was added and the mixture was stirred at room temperature for 35 minutes. Under nitrogen protection, intermediate C-3 (15 mmol, 6.08 g) was added. The solution was refluxed for 32 hours with magnetic stirring. After cooling, filtration, washing with water, drying, and column chromatography, intermediate G-1 was obtained.

[0192] In a three-necked flask under nitrogen protection, intermediate G-1 (10 mmol, 11.58 g) and 140 mL of o-dichlorobenzene were added. A 2.5 M solution of n-butyllithium in n-hexane (12 mmol, 4.8 mL) was added at -78 °C, the system was heated to 75 °C and reacted for 5.5 h. Then, boron tribromide (15 mmol, 1.5 mL) was added at 0 °C, and the reaction was continued at room temperature for 7.5 h. Next, N,N-diisopropylethylamine (20 mmol, 3.5 mL) was added at 0 °C, the system was heated to 135 °C and reacted for 16 h. After the reaction was complete, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to give compound 87. Compound 87 was reacted in toluene solution (1 × 10⁻⁶) -5 The half-width at half maximum (WHM) was 21 nm, obtained by measuring a Horiba Fluorolog-3 series fluorescence spectrometer.

[0193] Synthesis of compound 117:

[0194]

[0195] The synthesis of intermediate G-2 is the same as that of intermediate G-1, except that intermediate C-3 is replaced by intermediate C-7.

[0196] The synthesis of compound 117 is similar to that of compound 87, except that intermediate G-1 is replaced by intermediate G-2. Compound 117 is synthesized in toluene solution (1×10⁻⁶). -5 The half-width of the M peak was 22 nm, obtained by measuring the peak width using a Horiba Fluorolog-3 series fluorescence spectrometer.

[0197] Synthesis of compound 140:

[0198]

[0199] The synthesis of intermediate G-3 is the same as that of intermediate G-1, except that intermediate C-3 is replaced by intermediate C-4.

[0200] The synthesis of compound 140 is similar to that of compound 87, except that intermediate G-1 is replaced by intermediate G-3. Compound 140 is synthesized in toluene solution (1×10⁻⁶). -5 The half-width of the M peak was 22 nm, obtained by measuring the peak width using a Horiba Fluorolog-3 series fluorescence spectrometer.

[0201] Synthesis of compound 204:

[0202]

[0203] The synthesis of intermediate F-4 is similar to that of intermediate F-1, except that intermediate C-1 is replaced by intermediate C-2.

[0204] The synthesis of intermediate G-4 is the same as that of intermediate G-1, except that intermediate F-1 is replaced by intermediate F-4 and intermediate C-3 is replaced by intermediate C-5.

[0205] The synthesis of compound 204 is similar to that of compound 87, except that intermediate G-1 is replaced by intermediate G-4. Compound 204 is synthesized in toluene solution (1×10⁻⁶). -5 The half-width of the M peak was 22 nm, obtained by measuring the peak width using a Horiba Fluorolog-3 series fluorescence spectrometer.

[0206] Synthesis of Compound 1:

[0207]

[0208] The synthesis of intermediate F-5 is similar to that of intermediate F-1, except that raw material E-5 is used instead of raw material E-1.

[0209] The synthesis of intermediate G-5 is the same as that of intermediate G-1, except that intermediate F-1 is replaced by intermediate F-5.

[0210] The synthesis of compound 1 is similar to that of compound 87, except that intermediate G-1 is replaced by intermediate G-5. Compound 1 is synthesized in toluene solution (1×10⁻⁶). -5 The half-width at half maximum (WHM) was 23 nm, obtained by measuring a Horiba Fluorolog-3 series fluorescence spectrometer.

[0211] Synthesis of compound 59:

[0212]

[0213] The synthesis of intermediate G-6 is the same as that of intermediate G-1, except that intermediate F-1 is replaced by intermediate F-5 and intermediate C-3 is replaced by intermediate C-4.

[0214] The synthesis of compound 59 is similar to that of compound 87, except that intermediate G-1 is replaced by intermediate G-6. Compound 59 is synthesized in toluene solution (1×10⁻⁶). -5 The half-width at half maximum (WHM) was 23 nm, obtained by measuring a Horiba Fluorolog-3 series fluorescence spectrometer.

[0215] Synthesis of compound 242:

[0216]

[0217] Add raw material E-7 (20 mmol, 6.71 g) and cesium carbonate (55.2 mmol, 17.99 g) to a two-necked flask. Add 260 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 63 minutes. Add raw material F-7 (20 mmol, 5.59 g) under nitrogen protection. Reflux the solution under magnetic stirring for 36 hours. Cool, filter, wash with water, dry, and pass through a column to obtain intermediate G-7.

[0218] Intermediate G-7 (10 mmol, 5.95 g) was dissolved in 120 mL of tetrahydrofuran (THF) solution. Under nitrogen purging at -78 °C, 4.7 mL of tert-butyllithium (2.5 M, 11.7 mmol) n-hexane solution was slowly added. After stirring at -78 °C for 5.5 hours, 30 mL of tetrahydrofuran solution of starting material H-7 (10 mmol, 2.82 g) was slowly added. The reaction mixture was then slowly heated to room temperature and stirred overnight. 30 mL of dilute hydrochloric acid (1.0 M), 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 then slowly quenched with an aqueous solution of sodium bicarbonate (NaHCO3). Next, the aqueous layer was separated, extracted with dichloromethane, dried with sodium sulfate, filtered, distilled under reduced pressure, and passed through a column to obtain intermediate I-7.

[0219] Intermediate I-7 (5 mmol, 3.67 g), intermediate C-3 (5 mmol, 2.03 g), CuI catalyst (1 mmol, 0.19 g), and K3PO4 (25 mmol, 5.31 g) were added sequentially to a three-necked flask. Then, under a nitrogen atmosphere, trans-1,2-cyclohexanediamine (1.8 mmol, 0.21 g) and 90 mL of dioxane were added. The mixture was stirred at 106 °C for 22 hours. The reaction mixture was then cooled to room temperature, diluted with toluene, filtered through silica gel, and concentrated. The compounds were separated by silica gel column chromatography to obtain intermediate J-7.

[0220] In a three-necked flask under nitrogen protection, intermediate J-7 (10 mmol, 10.58 g) and 140 mL of o-dichlorobenzene were added. A 2.5 M solution of tert-butyllithium in n-hexane (12 mmol, 4.8 mL) was added at -78 °C, the system was heated to 68 °C and reacted for 7.5 h. Then, boron tribromide (15 mmol, 1.5 mL) was added at 0 °C, and the mixture was transferred to room temperature and reacted for another 8 h. Next, N,N-diisopropylethylamine (20 mmol, 3.5 mL) was added at 0 °C, the system was heated to 130 °C and reacted for 16 h. After the reaction was complete, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to give compound 242. Compound 242 was reacted in toluene solution (1 × 10⁻⁶) -5 The half-width of the M peak was 22 nm, obtained by measuring the peak width using a Horiba Fluorolog-3 series fluorescence spectrometer.

[0221] Synthesis of compound 248:

[0222]

[0223] The synthesis of intermediate J-8 is similar to that of intermediate J-7, except that intermediate C-3 is replaced by intermediate C-4.

[0224] The synthesis of compound 248 is similar to that of compound 239, except that intermediate J-7 is replaced by intermediate J-8. Compound 248 is synthesized in toluene solution (1×10⁻⁶). -5 The half-width at half maximum (WHM) was 23 nm, obtained by measuring a Horiba Fluorolog-3 series fluorescence spectrometer.

[0225] The structural characterization of the compounds obtained in each embodiment is shown in Table 1.

[0226] Table 1

[0227]

[0228] The following details the application effects of the organic electroluminescent materials synthesized in this invention in devices through Device Examples 1-8 and Comparative Examples 1-3. Device Examples 2-8 and Comparative Examples 1-3 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. The layer structures and test results of each device example are shown in Tables 2-1 and 3, respectively.

[0229] Device Example 1

[0230] like Figure 1As shown, the transparent substrate layer 1 is transparent glass. 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 organic electroluminescent device is fabricated, using GH-1 and GH-2 as the host materials and compound 87 as the dopant material, with a mass ratio of GH-1, GH-2, and compound 87 of 69:30:1. The light-emitting layer has a film thickness of 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.

[0231] The application effects of the organic electroluminescent materials synthesized in this invention in devices are described in detail below through device examples 9-34 and device comparative examples 4-6. The fabrication processes of device examples 10-34 and device comparative examples 4-6 are exactly the same as those of device example 9, and the same substrate and electrode materials are used. The film thickness of the electrode materials is also kept consistent. The only difference is that the light-emitting layer material in the device is replaced. The layer structure and test results of each device example are shown in Tables 2-2 and 3, respectively.

[0232] Device Example 9

[0233] The transparent substrate layer 1 is transparent glass. 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 light-emitting layer 6 of the organic electroluminescent device is fabricated. GH-1 and GH-2 are used as the host materials, GD-1 as the first dopant, and compound 87 as the second dopant. The mass ratio of GH-1, GH-2, GD-1, and compound 87 is 66.5:30:3:0.5, and the thickness of the light-emitting layer is 30 nm. After the light-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 by vacuum evaporation device, with a Mg:Ag mass ratio of 1:9. This layer is used as the cathode layer 10.

[0234] The molecular structural formulas of the relevant materials are shown below:

[0235]

[0236]

[0237] After the organic electroluminescent device is completed 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 2-1 and 2-2; the test results of the current efficiency and lifetime of the obtained devices are shown in Table 3.

[0238] Table 2-1

[0239]

[0240]

[0241]

[0242]

[0243]

[0244] Table 3

[0245]

[0246]

[0247] Note: Current efficiency and peak luminance were measured using an IVL (current-voltage-luminance) 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's brightness to decay to 95%; all data are within 10 mA / cm². 2 Next test.

[0248] As can be seen from the device data results in Table 3, compared with the comparative compounds ref-1, ref-2, and ref-3, the compounds of the present invention can achieve green light emission effect very well and have higher current efficiency; compared with devices of comparative examples 1-6, the current efficiency and lifetime of the devices are significantly improved compared with devices of known materials.

[0249] 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 1: In general formula 1, M1 and M2 are independently represented as C6 to C6 molecules substituted or unsubstituted by one or more R molecules. 30 The aromatic ring, C2-C2 with or without one or more R-substituted or unsubstituted R-substituted rings. 30 Heteroaromatic rings, C6-C6 substituted or unsubstituted with one or more R groups. 30 The aliphatic ring, C formed by the fusion of two or more aromatic rings, heteroaromatic rings, or aliphatic rings, substituted or unsubstituted with one or more Rs. 10 ~C 30 One type of fused ring; The presence of R, whether the same or different, indicates a deuterium atom, a halogen atom, a cyano group, or C1-C1 atoms that are substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, borane alkyl group substituted or unsubstituted, and silane alkyl group substituted or unsubstituted; The replacement of R is either a single bond or a parallel ring connection; R1, R2, and R3 are independently represented as hydrogen atom, deuterium atom, halogen atom, cyano group, and C1-C1 atoms substituted or unsubstituted with substituents, respectively. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, borane alkyl group substituted or unsubstituted, and silane alkyl group substituted or unsubstituted; Ar1, Ar2, Ar3, and Ar4 are independently represented as hydrogen atoms, deuterium atoms, halogen atoms, and C1-C1 atoms with or without substituents, respectively. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted boronyl groups; Ar1 and Ar2 are either not connected or connected in a ring; Ar3 and Ar4 are either not connected or connected in a ring; When Ar1 and Ar2, and Ar3 and Ar4 are simultaneously connected to form a ring, Ar4 and R1 are connected through... Connect them into a ring; Z1 and Z2 are independently represented as hydrogen atom, deuterium atom, halogen atom, and C1-C1 atoms substituted or unsubstituted, respectively. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted boronyl groups; When Z appears the same or different each time, it is represented as C-(H) or C-(R0); R0 represents a deuterium atom, a halogen atom, a cyano group, or a C1-C1 group that is substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, borane alkyl group substituted or unsubstituted, and silane alkyl group substituted or unsubstituted; The substituents are selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups; The heteroaryl group and the heteroatom in the heteroaryl ring are 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-type organic compound is shown in general formula 1-1 or general formula 1-2: In General Formulas 1-1 and 1-2, the meanings of M1, Ar1, Ar2, Ar3, Ar4, Z, R1, R2, and R3 are the same as those defined in General Formula 1 of claim 1.

3. The boron-containing resonance-type organic compound according to claim 1, characterized in that: The structure of the boron-containing resonance-type organic compound is shown in general formula 2-1 or general formula 2-2: In general formulas 2-1 and 2-2, the meanings of M1, M2, Ar1, Ar2, Ar3, Ar4, Z, Z1, and Z2 are the same as those defined in general formula 1 of claim 1; M3 represents C6-C6 substituted or unsubstituted with one or more R groups. 30 The aromatic ring, C2-C2 with or without one or more R-substituted or unsubstituted R-substituted rings. 30 Heteroaromatic rings, C6-C6 substituted or unsubstituted with one or more R groups. 30 The aliphatic ring, C formed by the fusion of two or more aromatic rings, heteroaromatic rings, or aliphatic rings, substituted or unsubstituted with one or more Rs. 10 ~C 30 One type of fused ring; The presence of R, whether the same or different, indicates a deuterium atom, a halogen atom, a cyano group, or C1-C1 atoms that are substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, borane alkyl group substituted or unsubstituted, and silane alkyl group substituted or unsubstituted; The replacement of R is either a single bond or a parallel ring connection; The substituents are selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups; The heteroaryl group and the heteroatom in the heteroaryl ring are selected from one or more of O, S, N, Si, and B; Preferably, the structure of the boron-containing resonance organic compound is shown in any one of general formulas 2-3 to 2-11: In formulas 2-3 to 2-11, the meanings of M1, Ar1, Ar2, Ar3, Ar4, Z, Z1, and Z2 are the same as those defined in formula 1 of claim 1; M3 represents C6-C6 substituted or unsubstituted with one or more R groups. 30 The aromatic ring, C2-C2 with or without one or more R-substituted or unsubstituted R-substituted rings. 30 Heteroaromatic rings, C6-C6 substituted or unsubstituted with one or more R groups. 30 The aliphatic ring, C formed by the fusion of two or more aromatic rings, heteroaromatic rings, or aliphatic rings, substituted or unsubstituted with one or more Rs. 10 ~C 30 One type of fused ring; The presence of R, whether the same or different, indicates a deuterium atom, a halogen atom, a cyano group, or C1-C1 atoms that are substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, borane alkyl group substituted or unsubstituted, and silane alkyl group substituted or unsubstituted; The replacement of R is either a single bond or a parallel ring connection; The substituents are selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups; The heteroaryl group and the heteroatom in the heteroaryl ring are selected from one or more of O, S, N, Si, and B.

4. 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 any one of general formulas 3-1 to 3-15: In formulas 3-1 to 3-15, the meanings of Ar1, Ar2, Ar3, Ar4, Z, Z1, and Z2 are the same as those defined in formula 1 of claim 1; Preferably, the structure of the boron-containing resonance organic compound is shown in any one of general formulas (4-1) to (4-6): In general formulas (4-1) to (4-6), the meaning of Z is the same as that defined in general formula 1 of claim 1.

5. 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 any one of general formulas 5-1 to 5-4: In general formulas 5-1 to 5-4, the meanings of Ar1, Ar2, Ar3, Ar4, R1, R2, R3, Z1, and Z2 are the same as those defined in general formula 1 of claim 1; The R4, R5, R6, R7, R8, R9, R 10 Each of the following can be represented independently as a hydrogen atom, deuterium atom, halogen atom, cyano group, or C1-C1 atoms substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, borane alkyl group substituted or unsubstituted, and silane alkyl group substituted or unsubstituted; The m7 is represented as 0, 1, 2, 3, 4 or 5; The m4, m5, m6, m8, m 10 Each can be independently represented as 0, 1, 2, 3, or 4; The m9, m 11 Each can be independently represented as 0, 1, 2, or 3; The substituents are selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups; The heteroaryl group and the heteroatom in the heteroaryl ring are selected from one or more of O, S, N, Si, and B; Preferably, the structure of the boron-containing resonance organic compound is shown in any one of general formulas 5-5 to 5-8: In formulas 5-5 to 5-8, the meanings of Ar1, Ar2, Ar3, Ar4, R1, R2, R3, Z1, and Z2 are the same as those defined in formula 1 of claim 1; The R4, R5, R6, R7, R8, R9, R 10 Each of these can be represented independently as a hydrogen atom, deuterium atom, halogen atom, cyano group, C1-C10 alkyl group (substituted or unsubstituted), C3-C10 cycloalkyl group (substituted or unsubstituted), C2-C10 alkenyl group (substituted or unsubstituted), C2-C10 alkynyl group (substituted or unsubstituted), C6-C10 aryloxy group (substituted or unsubstituted), arylamine group (substituted or unsubstituted), C6-C30 aryl group (substituted or unsubstituted), and C2-C10 aryl group (substituted or unsubstituted). 30 One of heteroaryl, borane alkyl group substituted or unsubstituted, and silane alkyl group substituted or unsubstituted; The m7 is represented as 0, 1, 2, 3, 4 or 5; The m4, m8, m 10 Each can be independently represented as 0, 1, 2, 3, or 4; The substituents are selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 Any one or more of the heteroaryl groups; The heteroaryl group and the heteroatom in the heteroaryl ring are selected from one or more of O, S, N, Si, and B.

6. The boron-containing organic compound according to any one of claims 1-5, characterized in that, M1, M2, and M3 represent any one of the following groups substituted or unsubstituted with one or more R groups: phenyl, naphthyl, anthraceneyl, phenanthryl, pyridyl, quinolinyl, furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, indole[3,2,1-jk]carbazoyl, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, and spirofluorenyl. R and RO represent a deuterium atom, a halogen atom, a cyano group, a methyl group (substituted or unsubstituted), an ethyl group (substituted or unsubstituted), an isopropyl group (substituted or unsubstituted), a tert-butyl group (substituted or unsubstituted), a cyclohexyl group (substituted or unsubstituted), a cyclopentyl group (substituted or unsubstituted), an adamantyl group (substituted or unsubstituted), a phenyl group (substituted or unsubstituted), a diphenyl group (substituted or unsubstituted), a terphenyl group (substituted or unsubstituted), a naphthyl group (substituted or unsubstituted), anthracene group (substituted or unsubstituted), a phenanthryl group (substituted or unsubstituted), a pyridyl group (substituted or unsubstituted), a quinolinyl group (substituted or unsubstituted), and a furanyl group (substituted or unsubstituted). Thiophene group substituted or unsubstituted, benzofuran group substituted or unsubstituted, benzothiophene group substituted or unsubstituted, dibenzofuran group substituted or unsubstituted, dibenzothiophene group substituted or unsubstituted, carbazolyl group substituted or unsubstituted, 9,9-dimethylfluorenyl group substituted or unsubstituted, 9,9-diphenylfluorenyl group substituted or unsubstituted, spirofluorenyl group substituted or unsubstituted, triazine group substituted or unsubstituted, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl group substituted or unsubstituted, diphenylamino group substituted or unsubstituted, indole group substituted or unsubstituted, benzoindole group substituted or unsubstituted; The R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 Represented as deuterium atom, halogen atom, cyano group, 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), cyclopentyl 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 group (substituted or unsubstituted), furanyl group (substituted or unsubstituted), etc. Substituted or unsubstituted thiophene group, substituted or unsubstituted benzofuran group, substituted or unsubstituted benzothiophene group, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted dibenzothiophene group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted 9,9-dimethylfluorenyl group, substituted or unsubstituted 9,9-diphenylfluorenyl group, substituted or unsubstituted spirofluorenyl group, substituted or unsubstituted triazine group, substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl group, substituted or unsubstituted diphenylamino group, substituted or unsubstituted indole group, substituted or unsubstituted benzoindole group; Ar1, Ar2, Ar3, Ar4, Z1, and Z2 are independently represented as hydrogen atom, deuterium atom, halogen atom, cyano group, 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), cyclopentyl 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 group (substituted or unsubstituted), and so on. Substituent-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 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted triazineyl, substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, substituted or unsubstituted diphenylamino, substituted or unsubstituted indoleyl, substituted or unsubstituted benzoindoleyl; The substituents are selected from one or more of the following: deuterium, chlorine, fluorine, trifluoromethyl, 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, indoleyl, pyrroleyl, dibenzofuranyl, dibenzothiapheneyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazolyl, N-phenylcarbazolyl, carbazolinyl, azirphenanthreneyl, diphenylamino, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, and benzoindoleyl.

7. 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:

8. An organic light-emitting device, comprising a substrate, a first electrode, an organic functional material layer, and a second electrode, wherein the first electrode is located on the substrate, the organic functional material layer is located on the first electrode, and the second electrode is located on the functional layer, characterized in that: The organic functional material layer contains the boron-containing resonant organic compound as described in any one of claims 1-7.

9. The organic light-emitting device according to claim 8, wherein the organic functional material layer comprises a light-emitting layer, characterized in that: The light-emitting layer 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 1-7. Preferably, the light-emitting layer comprises a first host material, a second host material, and a dopant material, wherein 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 1-7.

10. The organic light-emitting device according to claim 9, wherein the light-emitting layer comprises a host material, an exciton-sensitizing material, and a dopant material, characterized in that: The exciton sensitizing material is a complex containing a metal element, and the doping material is a boron-containing organic compound as described in any one of claims 1-7.

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