A resonance type organic compound and an organic light emitting device comprising the same

Abstract

The present application relates to a kind of resonance type organic compound and the organic light-emitting device comprising it, belong to semiconductor technical field, the present application provides the structure of compound as shown in general formula (1): The compound of the present application has narrow half-width, high fluorescent quantum yield, when being used as the doping material in the light-emitting layer material of OLED light-emitting device, the current efficiency of device is significantly improved, and the luminous color purity and device life are also greatly improved.

Description

Technical Field

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

[0002] Traditional fluorescent doped materials, limited by early technologies, can only emit light using 25% of singlet excitons generated by electrical excitation. This results in low internal quantum efficiency (maximum 25%) and external quantum efficiency generally below 5%, significantly lower than that of phosphorescent devices. Phosphorescent materials, due to the strong spin-orbit coupling at the heavy atom centers, enhance intersystem crossing and can effectively utilize both singlet and triplet excitons generated by electrical excitation for emission, achieving an internal quantum efficiency of 100%.

[0003] With the advent of the 5G era, higher requirements have been placed on color rendering standards. In addition to high efficiency and stability, luminescent materials also need narrower half-widths (HWHMs) to improve the purity of the emitted color in devices. Fluorescent dopants can achieve high fluorescence quantum density and narrow HWHM through molecular engineering. Significant breakthroughs have been achieved in blue fluorescent dopants, with the HWHM of boron-based materials reduced to below 30 nm. However, research on the green light region, which is more sensitive to the human eye, has mainly focused on phosphorescent dopants. However, the peak shape of these dopants is difficult to narrow using simple methods. Therefore, researching efficient green fluorescent dopants with narrow HWHMs is of great significance in meeting higher color rendering standards.

[0004] In addition, sensitization technology combines triplet exciton sensitizing materials with fluorescent doping materials. By using triplet exciton sensitizing materials as exciton sensitization media, it makes full use of triplet excitons and transfers energy to fluorescent doping materials through energy transfer, achieving 100% in-device quantum efficiency. This technology can make up for the shortcomings of insufficient exciton utilization in 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 in OLED applications.

[0005] Boron compounds with resonant structures are more likely to achieve narrow half-width emission (HWHM). When applied to sensitized fluorescence technology, these materials can enable the fabrication of devices with high efficiency and narrow HWHM emission. For example, CN 107507921 A and CN 110492006 A 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 110492005 A and CN 110492009 A disclose a light-emitting layer combination scheme using exciton complexes as the main body and boron-containing materials as dopants; both achieve efficiencies comparable to phosphorescence and relatively narrow HWHM. Therefore, developing sensitization technology based on narrow HWHM boron-based light-emitting materials has unique advantages and strong potential for achieving BT.2020 display performance. Summary of the Invention

[0006] To address the aforementioned problems in the prior art, the applicant of this invention provides a resonant organic compound and an organic light-emitting device comprising the same. The compound of this invention can be used as a green light-doping material in the light-emitting layer of an organic electroluminescent device, thereby improving the device's efficiency and lifespan.

[0007] The technical solution of the present invention is as follows: a resonance-type organic compound, the structure of which is shown in general formula (1):

[0008]

[0009] In general formula (1), Z represents CH or CR. a ;

[0010] R a Each instance of the same or different is represented as a deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted aromatic amino groups, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups;

[0011] Z1, Z2, Z3, Z4, Z5, Z6, Z7, and Z8 are each independently represented as CH or CR. b ;

[0012] R b Each instance of the same or different is represented as a deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted aromatic amino groups, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups;

[0013] X is independently represented as O, S, N-(R) c ), C-(R d (R) e ), Si-(R) f (R) g );

[0014] R c R d R e R f R gIndicated as substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups;

[0015] M1 represents substituted or unsubstituted C6-C. 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl groups;

[0016] R c R d R e R f R g It can be connected to M1 to form a ring;

[0017] R1, R2, R3, R4, R5, R6, and R7 are independently represented as hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C atom, respectively. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted aromatic amino groups, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups;

[0018] The substituents used for the substituent groups are optionally selected from halogen atoms, deuterium atoms, cyano groups, C1-C... 10 Alkyl, C5-C 10 cycloalkyl, C5-C 10 Cycloalkenyl, C1-C 10 alkoxy groups, C3-C 20 cycloalkyl, C6-C 30 Aryl, C3-C 30 One or more of the heteroaryl groups;

[0019] The heteroatom in the heteroaryl group is selected from one of O, S, N, and Si.

[0020] In a preferred embodiment, the structure of the resonance-type organic compound is shown in any one of general formulas (1-1) to (1-8):

[0021]

[0022]

[0023] In general formulas (1-1) to (1-8), the definitions of Z, M1, Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8, R1, R2, R3, R4, R5, R6, and R7 are the same as those in the above description.

[0024] In a preferred embodiment, the structure of the resonance-type organic compound is shown in any one of general formulas (2-1) to (2-5):

[0025]

[0026]

[0027] In general formulas (2-1) to (2-5), the definitions of Z, X, M1, Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8, R4, R5, R6, and R7 are the same as those in the above description.

[0028] In a preferred embodiment, the structure of the resonance-type organic compound is shown in any one of general formulas (3-1) to (3-5):

[0029]

[0030] In general formulas (3-1) to (3-5), the definitions of Z, Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8, R1, R2, R3, R4, R5, R6, R7, and X are the same as those in the above description.

[0031] X1 is represented as O or S;

[0032] The R8, R9, R 10 R 11 R 12 R 13 R 14 Represented independently as hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted aromatic amino groups, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups;

[0033] The substituents used for the substituent groups are optionally selected from halogen atoms, deuterium atoms, cyano groups, C1-C... 10 Alkyl, C5-C 10 cycloalkyl, C5-C 10 Cycloalkenyl, C1-C 10 alkoxy groups, C3-C 20 cycloalkyl, C6-C30 Aryl, C3-C 30 One or more of the heteroaryl groups;

[0034] The heteroatom in the heteroaryl group is selected from one of O, S, N, and Si.

[0035] In the preferred embodiment, R1, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 12 R 13 R 14 Each instance of the same or different element is represented by a hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted isopropyl group, substituted or unsubstituted tert-butyl group, substituted or unsubstituted cyclohexyl group, substituted or unsubstituted adamantyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted diphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthracene group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted pyridyl group, substituted or Unsubstituted quinolinyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amino, substituted or unsubstituted triazineyl;

[0036] The R a R b Each instance of the same or different element is represented by a hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted isopropyl group, substituted or unsubstituted tert-butyl group, substituted or unsubstituted cyclohexyl group, substituted or unsubstituted adamantyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted diphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthracene group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted pyridyl group, substituted or Unsubstituted quinolinyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amino, substituted or unsubstituted triazineyl;

[0037] The R c R d R e R f R g The following are represented as substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, etc. Substituted or unsubstituted furanyl, substituted or unsubstituted thiophene, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amino.

[0038] The M1 represents one of the following: substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiophenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted indole[3,2,1-jk]carbazoyl, and substituted or unsubstituted 4a,9a-dimethyl-9-phenyl-1,2,3,4-tetrahydrocarbazoyl.

[0039] The substituents used for the substituent groups are selected from one or more of the following: deuterium atom, chlorine atom, fluorine atom, trifluoromethyl, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthrene, pyridinyl, pyrazinyl, pyrazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheneyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheninyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazoleyl, N-phenylcarbazoleyl, carbazolinyl, and aziphenanthreneyl.

[0040] In a preferred embodiment, M1 is represented by any of the following ring structures:

[0041]

[0042] The definition of Z in the above formula is the same as the limitation mentioned above;

[0043] In the preferred embodiment, the R a R b It can be represented as the structure shown below:

[0044]

[0045] Any one of them;

[0046] In the preferred embodiment, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 12 R 13 R 14 R c It can be represented as the structure shown below:

[0047] hydrogen atom,

[0048] Any one of the following. Preferably, the resonance-type organic compound has a specific structural formula of any one of the following:

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065] The present invention also provides an organic light-emitting device comprising a cathode, an anode, and a functional layer, wherein the functional layer is located between the cathode and the anode, and the functional layer of the organic light-emitting device contains the resonant organic compound.

[0066] Preferably, the functional layer includes a light-emitting layer, which comprises a host material and a dopant material, wherein the dopant material is the resonant organic compound.

[0067] In a preferred embodiment, 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 the resonant organic compound.

[0068] In a preferred embodiment, the light-emitting layer comprises a host material, an exciton-sensitizing material, and a dopant material, wherein the exciton-sensitizing material is a complex containing a metal element, and the dopant material is the resonant organic compound.

[0069] Compared with the prior art, the beneficial technical effects of the present invention are as follows:

[0070] (1) The compound of the present invention can be used as a dopant material for OLED devices, and can emit green fluorescence under the action of an electric field. It can be applied to OLED lighting or OLED display fields.

[0071] (2) The compound of the present invention is used as a doping material, and phosphorescent material is introduced as an exciton sensitizer, which can effectively improve the device lifetime;

[0072] (3) The compounds of the present invention have a narrower FWHM spectrum, which can effectively improve the color gamut of the device and improve the luminous efficiency of the device;

[0073] The compounds of this invention have narrow half-widths and can be used as doping materials for the light-emitting layer of organic electroluminescent devices, thereby improving the purity of the emitted color and the lifetime of the device. Attached Figure Description

[0074] Figure 1 This is a schematic diagram of the structure of an OLED device in which the materials listed in this invention are applied;

[0075] 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

[0076] The present invention will now be described in detail with reference to the accompanying drawings and embodiments.

[0077] 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.

[0078] In this invention, C6-C is substituted or unsubstituted. 30 Aryl groups refer to substituted or unsubstituted phenyl groups, substituted or unsubstituted naphthyl groups, substituted or unsubstituted anthraquinyl groups, substituted or unsubstituted fluorenyl groups, substituted or unsubstituted dimethylfluorenyl groups, substituted or unsubstituted diphenylfluorenyl groups, substituted or unsubstituted spirofluorenyl groups, substituted or unsubstituted phenanthrene groups, substituted or unsubstituted tetraphenyl groups, substituted or unsubstituted pyrene groups, substituted or unsubstituted biphenyl groups, substituted or unsubstituted para-triphenyl groups, substituted or unsubstituted meta-triphenyl groups, and substituted or unsubstituted phenyl groups. The compounds may be substituted or unsubstituted triphenyl, substituted or unsubstituted peryl, substituted or unsubstituted indole, but are not limited thereto.

[0079] In this invention, C3-C is substituted or unsubstituted. 30Heteroaryl refers to substituted or unsubstituted furanyl, substituted or unsubstituted thiophene, substituted or unsubstituted pyrrole, substituted or unsubstituted pyrazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted oxadiazolyl, substituted or unsubstituted thiadiazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted triazine, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophene, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted... The fused ring of substituted indolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted naphridyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridineyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenthiazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted fumonyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoleyl, combinations thereof, or combinations of the foregoing groups, but not limited thereto.

[0080] The C1-C of this invention 10 Alkyl groups (including straight-chain alkyl and branched-chain alkyl) refer to methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, sec-butyl, neopentyl, n-pentyl, isopentyl, octyl, heptyl, n-decyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 1-butylpentyl, etc., but are not limited to these.

[0081] The C3-C of this invention 10 Cycloalkyl refers to a monovalent monocyclic saturated hydrocarbon group comprising 3 to 10 carbon atoms as cyclic atoms. In this document, C4-C9 cycloalkyl groups are preferred, C5-C8 cycloalkyl groups are more preferred, and C5-C7 cycloalkyl groups are particularly preferred. Non-limiting examples may include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl, and cycloheptyl.

[0082] 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 plastic substrates; and opaque substrates, such as silicon substrates. Different substrates have different mechanical strengths, thermal stability, transparency, surface smoothness, and water resistance. Depending on the properties of the substrate, its application direction varies. In this invention, a transparent PI film substrate is preferred. There are no particular limitations on the thickness of the substrate.

[0083] 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 Ag, Mg, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, or a mixture of metals. 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.

[0084] 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.

[0085] In this paper, the hole transport region constituting an organic electroluminescent device can be listed as a hole injection layer, a hole transport layer, an electron blocking layer, etc.

[0086] 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 OLED devices.

[0087] Examples of the aforementioned materials include phthalocyanine derivatives, triazole derivatives, triarylmethane derivatives, triarylamine derivatives, oxazole derivatives, oxadiazole derivatives, hydrazone derivatives, stilbene derivatives, pyridinium derivatives, polysilane derivatives, imidazole derivatives, phenylenediamine derivatives, amino-substituted quinone derivatives, styrene-based anthracene derivatives, styrene-based amine derivatives, styrene compounds, fluorene derivatives, spirofluorene derivatives, silazane derivatives, aniline copolymers, porphyrin compounds, carbazole derivatives, polyaryl alkane derivatives, polyphenylene oxide and its derivatives, polythiophene and its derivatives, poly-N-vinylcarbazole derivatives, thiophene oligomers and other conductive polymers, aromatic tertiary amine compounds, and styrene aminations. Compounds, triamines, tetraamines, benzidines, propyne diamine derivatives, p-phenylenediamine derivatives, m-phenylenediamine derivatives, 1,1'-bis(4-diarylaminophenyl)cyclohexane, 4,4'-bis(diarylamine)biphenyls, bis[4-(diarylamino)phenyl]methanes, 4,4'-bis(diarylamino)terphenyls, 4,4'-bis(diarylamino)tetraphenyls, 4,4'-bis(diarylamino)diphenyl ethers, 4,4'-bis(diarylamino)diphenylsulfanes, bis[4-(diarylamino)phenyl]dimethylmethanes, bis[4-(diarylamino)phenyl]-bis(trifluoromethyl)methanes, or 2,2-diphenylethylene compounds, etc.

[0088] Furthermore, depending on the device configuration requirements, the hole transport film layer between the electron blocking and hole injection layers of an organic electroluminescent device can be a single film layer or a stacked structure of multiple hole transport materials. In this paper, the film thickness of the various hole carrier conduction films with different functions is not particularly limited.

[0089] 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.

[0090] Based on the above empirical summary, different P-doped materials need to be selected to match the hole-based host materials of different HOMO energy levels in order to achieve ohmic contact at the interface and improve the hole injection effect.

[0091] Therefore, in one embodiment of the present invention, in order to improve hole injection, the hole injection layer further 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.

[0092] 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.

[0093] 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.

[0094] 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.

[0095] 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.

[0096] 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.

[0097] The light-emitting layer may include a host material and a dopant material. The host material may be a green light host material commonly used in the art, and the dopant material may be a resonant organic compound represented by the general formula (1) of this invention.

[0098] The light-emitting layer can contain a single-substrate material or a dual-substrate material;

[0099] 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;

[0100] 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.

[0101] The light-emitting layer may include a host material, an exciton-sensitizing material, and a dopant material;

[0102] 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 resonant organic compound shown in general formula (1) of this invention, when used in combination with exciton-sensitized materials, has a significant effect on improving device efficiency, exciton annihilation in the device, and efficiency reduction.

[0103] 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.

[0104] 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.

[0105] 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.

[0106] A hole-blocking layer is a layer that prevents holes injected from the anode from passing through the light-emitting layer and entering the cathode, thereby extending the device's lifetime and improving its efficiency. The hole-blocking layer of this invention can be disposed above 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, such as phenanthroline derivatives like copper hydroxide (BCP), metal complexes of hydroxyquinoline derivatives like aluminum(III)bis(2-methyl-8-quinoline)-4-phenylphenol (BAlq), various rare earth complexes, oxazole derivatives, triazole derivatives, triazine derivatives, pyrimidine derivatives like 9,9'-(5-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-1,3-phenylene)bis(9H-carbazole), etc. The thickness of the hole-blocking layer of this invention can be 2-200 nm, preferably 5-150 nm, but the thickness is not limited to this range.

[0107] 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 the received electrons to the light-emitting layer. Materials with high electron mobility are preferred. As the electron transport layer of the organic electroluminescent device of the present invention, electron transport layer materials known in the prior art for organic electroluminescent devices can be used, such as metal complexes of hydroxyquinoline derivatives represented by Alq3, BAlq and Liq, various rare earth metal complexes, triazole derivatives, triazine derivatives such as 2,4-bis(9,9-dimethyl-9H-fluoren-2-yl)-6-(naphthyl-2-yl)-1,3,5-triazine (CAS No.: 1459162-51-6), imidazole derivatives such as 2-(4-(9,10-bis(naphthyl-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole (CAS No.: 561064-11-7, commonly known as LG201), oxadiazole derivatives, thiadiazole derivatives, carbodiimide derivatives, quinoxaline derivatives, phenanthroline derivatives, silicon-based compound derivatives, etc. 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.

[0108] An electron injection layer may be disposed above the electron transport layer. The electron injection layer material is typically preferably a material with a low work function, allowing electrons to be easily injected into the organic functional material layer. As the electron injection layer material for the organic electroluminescent device of the present invention, electron injection layer materials known in the art for organic electroluminescent devices can be used, such as lithium; lithium salts, such as lithium 8-hydroxyquinoline, lithium fluoride, lithium carbonate, or lithium azide; or cesium salts, such as cesium fluoride, cesium carbonate, or cesium azide. The thickness of the electron injection layer of the present invention may 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.

[0109] The second electrode may be disposed above the electron transport region. The second electrode may be a cathode. The second electrode may be a transmission electrode, a semi-transmission electrode, or a reflection electrode. When the second electrode is a transmission electrode, it may include, for example, Li, Yb, Ca, LiF / Ca, LiF / Al, Al, Mg, BaF, Ba, Ag, or compounds or mixtures thereof; when the second electrode is a semi-transmission electrode or a reflection electrode, it may include Ag, Mg, Yb, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, or compounds or mixtures thereof, but is not limited thereto. The thickness of the cathode depends on the material used.

[0110] 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.

[0111] The method for preparing the organic electroluminescent device of the present invention includes sequentially laminating an anode, a hole injection layer, a hole transport layer, an electron blocking layer, an organic film layer, an electron transport layer, an electron injection layer, and a cathode, and optionally a capping layer, onto a substrate. In this regard, methods such as vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing, or LITI can be used, but are not limited thereto. In the present invention, vacuum evaporation is preferably used to form the various layers. Those skilled in the art can conventionally select the various process conditions in the vacuum evaporation method according to actual needs.

[0112] Synthesis Examples

[0113] All raw materials involved in the synthesis embodiments of this invention can be purchased from the market or obtained by conventional preparation methods in the art.

[0114] I. Synthesis of intermediate J

[0115] 1. Synthesis of intermediate J1:

[0116]

[0117] Under nitrogen protection, starting material M1 (367 mg), starting material M2 (228 mg), potassium tert-butoxide (168 mg), Pd2(dba)3 (46 mg), tri-tert-butylphosphine (30 mg), and 20 mL of anhydrous toluene were added to a three-necked flask, and the mixture was refluxed for 18 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate Y1. LC-MS: Measured value: 467.22 ([M+H) + Theoretical value: 466.10.

[0118] Under nitrogen protection, intermediate Y1 (467 mg), starting material M3 (120 mg), and 10 mL of trifluoroacetic acid solution were added to a three-necked flask, and the mixture was reacted in an ice-water bath for 3 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate Y2. LC-MS: Measured value: 551.29 ([M+H)) + Theoretical value: 550.16.

[0119] In a double-necked flask under nitrogen protection, intermediate Y2 (196 mg) was dissolved in 15 mL of anhydrous THF. The mixture was then cooled to -78 °C and held for 10 min. Subsequently, 1.6 M n-BuLi (2.1 mL) was added dropwise to the reaction mixture over 10 min, and the mixture was stirred at -78 °C for 1 h. Then, starting material M4 (137 mg) was added to the mixture, and the mixture was stirred overnight at room temperature. The reaction was then quenched with water, and after removing the solvent under vacuum, the residue was extracted with CH2Cl2 and water. The organic phase was dried over anhydrous Na2SO4, and the solvent was removed under vacuum. The residue was recrystallized from petroleum ether. After filtration, the residue was dissolved in 30 mL of CH3COOH, and then 1 mL of HCl was added. The mixture was stirred at 110 °C for 5 h. After cooling to room temperature, the mixture was poured into 100 mL of ice water and filtered to obtain the crude product. The crude product was purified by silica gel column chromatography (petroleum ether / CH2Cl2 = 10 / 1) to obtain intermediate Y3. LC-MS: Measured value: 635.14 ([M+H]) + Theoretical value: 634.30.

[0120] Intermediate Y3 (651 mg), NaOH (1 mg), and 15 mL of ethanol solution were added to a three-necked flask and reacted at room temperature for 5 hours. After the reaction was complete, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate J1. LC-MS: Measured value: 551.09 ([M+H)) + Theoretical value: 550.24.

[0121] 2. Synthesis of intermediate J2:

[0122]

[0123] Under nitrogen protection, starting material M1 (367 mg), starting material M5 (172 mg), potassium tert-butoxide (168 mg), Pd2(dba)3 (46 mg), tri-tert-butylphosphine (30 mg), and 20 mL of anhydrous toluene were added to a three-necked flask, and the mixture was refluxed for 18 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate Y4. LC-MS: Measured value: 411.12 ([M+H) + Theoretical value: 410.04.

[0124] Under nitrogen protection, intermediate Y4 (411 mg), starting material M3 (121 mg), and 10 mL of trifluoroacetic acid solution were added to a three-necked flask, and the mixture was reacted in an ice-water bath for 3 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate Y5. LC-MS: Measured value: 495.23 ([M+H) + Theoretical value: 494.10.

[0125] In a double-necked flask under nitrogen protection, intermediate Y5 (176 mg) was dissolved in 15 mL of anhydrous THF. The mixture was then cooled to -78 °C and held at this temperature for 10 min. Subsequently, 1.6 M n-BuLi (2.1 mL) was added dropwise to the reaction mixture over 10 min, and the mixture was stirred at -78 °C for 1 h. Then, starting material M4 (137 mg) was added to the mixture, and the mixture was stirred overnight at room temperature. The reaction was then quenched with water, and after removing the solvent under vacuum, the residue was extracted with CH2Cl2 and water. The organic phase was dried over anhydrous Na2SO4, and the solvent was removed under vacuum. The residue was recrystallized from petroleum ether. After filtration, the residue was dissolved in 30 mL of CH3COOH, and then 1 mL of HCl was added. The mixture was stirred at 110 °C for 5 h. After cooling to room temperature, the mixture was poured into 100 mL of ice water and filtered to obtain the crude product. The crude product was purified by silica gel column chromatography (petroleum ether / CH2Cl2 = 10 / 1) to obtain intermediate Y6. LC-MS: Measured value: 579.31 ([M+H]) + Theoretical value: 578.24.

[0126] Intermediate Y6 (595 mg), NaOH (1 mg), and 15 mL of ethanol solution were added to a three-necked flask and reacted at room temperature for 5 hours. After the reaction was complete, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate J2. LC-MS: Measured value: 495.28 ([M+H)) + Theoretical value: 494.18.

[0127] II. Synthesis of Compounds in Examples

[0128] Example 1: Synthesis of Compound 28:

[0129]

[0130]

[0131] Preparation of intermediate U1:

[0132] Under nitrogen protection, starting material N1 (335 mg), phenylboronic acid (122 mg), potassium carbonate (207 mg), Pd(PPh3)4 (58 mg), 20 mL of anhydrous toluene, and 5 mL of water were added to a three-necked flask, and the mixture was refluxed for 10 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate U1. LC-MS: Measured value: 284.99 ([M+H) + Theoretical value: 283.94.

[0133] Preparation of intermediate K1:

[0134] Under nitrogen protection, intermediates U1 (286 mg), J1 (551 mg), potassium tert-butoxide (168 mg), Pd2(dba)3 (46 mg), tri-tert-butylphosphine (30 mg), and 20 mL of anhydrous toluene were added to a three-necked flask, and the mixture was refluxed for 12 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate K1. LC-MS: Measured value: 755.18 ([M+H)) + Theoretical value: 754.26.

[0135] Preparation of intermediate P1:

[0136] In a three-necked flask under nitrogen protection, intermediate K1 (755 mg), starting material B1 (195 mg), cesium carbonate (49 mg), and 30 mL of anhydrous DMF were added. The mixture was heated to 120 °C in the dark and reacted for 20 hours. After natural cooling to room temperature, 100 mL of water was added, the mixture was filtered, and the precipitate was collected. The precipitate was dissolved in 20 mL of dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography to obtain intermediate P1. LC-MS: Measured value: 885.22 ([M+H) + Theoretical value: 884.35.

[0137] Preparation of compound 28:

[0138] In a sealed, pressure-resistant tube under nitrogen protection, intermediate P1 (886 mg) and 15 mL of anhydrous o-dichlorobenzene were added. After cooling to -78 °C, 30 mL of 2.5 M tert-butyllithium-n-hexane solution was added dropwise. The mixture was heated to 60 °C and reacted for 4 hours. The reaction was then cooled to -42 °C, and 1.5 mL of boron tribromide was added dropwise. After slowly restoring to room temperature, the reaction was allowed to continue for 8 hours. At 0 °C, 2.6 mL of ultra-dry N,N-diisopropylethylamine was added dropwise. The reaction mixture was heated to 180 °C and reacted for 48 hours. After cooling to room temperature, the low-boiling solvent was removed by vacuum distillation. The solution was dissolved in dichloromethane, filtered, dried over anhydrous sodium sulfate, and the filtrate was collected. The filtrate was concentrated and purified by column chromatography to give compound 28. Elemental analysis of the structure (C...) 63 H 47 Theoretical values ​​for BN₂O: C, 88.10; H, 5.52; N, 3.26; Measured values: C, 88.01; H, 5.45; N, 3.19. LC-MS: Measured value: 859.40 ([M+H]). + Theoretical value: 858.38. 1 ¹H NMR (400MHz, Chloroform-d) δ 7.99 (m, 2H), 7.83 (m, 2H), 7.66–7.55 (m, 4H), 7.49–7.25 (m, 11H), 7.19 (d, 1H), 7.16–7.11 (m, 1H), 7.04–6.95 (m, 3H), 6.91 (d, 1H), 6.83–6.77 (m, 3H), 6.61 (d, 1H), 1.69 (d, 18H). In toluene solution (1×10⁻⁶) -5 The full width at half maximum (FWHM) is 21 nm.

[0139] Example 2: Synthesis of Compound 146:

[0140]

[0141] Preparation of intermediate K2:

[0142] Under nitrogen protection, starting material A1 (310 mg), intermediate J1 (551 mg), potassium tert-butoxide (168 mg), Pd2(dba)3 (46 mg), tri-tert-butylphosphine (30 mg), and 20 mL of anhydrous toluene were added to a three-necked flask, and the mixture was refluxed for 12 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate K2. LC-MS: Measured value: 779.36 ([M+H) + Theoretical value: 778.24.

[0143] Preparation of intermediate P2:

[0144] In a three-necked flask under nitrogen protection, intermediate K2 (780 mg), starting material B2 (188 mg), cesium carbonate (49 mg), and 20 mL of anhydrous DMF were added. The mixture was heated to 120 °C in the dark and reacted for 20 hours. After natural cooling to room temperature, 100 mL of water was added, the mixture was filtered, and the precipitate was collected. The precipitate was dissolved in 20 mL of dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography to obtain intermediate P2. LC-MS: Measured value: 903.18 ([M+H)) + Theoretical value: 902.21.

[0145] Preparation of intermediate T2:

[0146] Intermediate P2 (444 mg) and tert-butylbenzene (50 mL) were added sequentially to a sealed pressure-resistant tube. The temperature was lowered to -78°C, and a hexane solution of n-butyllithium (1 mL) was slowly added. The mixture was then stirred and brought to room temperature. Subsequently, the hexane was removed under negative pressure at 60°C. Nitrogen protection was then introduced, and the reaction proceeded for 2 hours. Boron tribromide (1.5 mL) was added at -45°C, and the temperature was maintained with stirring for 4 hours. The temperature was then slowly restored to room temperature, and the mixture was stirred at room temperature for 12 hours. DIPEA (N,N-diisopropylethylamine) (2.6 mL) was added under ice-water bath conditions, and the mixture was heated to 150°C and refluxed for 35 hours. The reaction was cooled to room temperature, and the solution was filtered through diatomaceous earth. The organic phase was collected, and high-boiling solvents were removed by vacuum distillation. The solution was dissolved in dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography using toluene as the developing solvent to obtain intermediate T2. LC-MS: Measured value: 833.40 ([M+H) + Theoretical value: 832.29.

[0147] Preparation of compound 146:

[0148] Under nitrogen protection, intermediate T2 (163 mg) and CuCN (27 mg) were dissolved in 5 mL of LDM, heated to 150 °C and stirred for 12 hours. After cooling to room temperature, the solution was filtered through diatomaceous earth and washed with dichloromethane. The filtrate was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give compound 146. Elemental analysis of the structure (C...) 58 H 42 BN3S) Theoretical values: C, 84.56; H, 5.14; N, 5.10; S, 3.89; Measured values: C, 84.57; H, 5.13; N, 5.08; S, 3.93. LC-MS: Measured value: 824.25 ([M+H]) + Theoretical value: 823.32. 1¹H NMR (400 MHz, Chloroform-d) δ 8.08–7.93 (m, 2H), 7.83 (m, 2H), 7.69–7.57 (m, 2H), 7.50–7.28 (m, 11H), 7.23–7.09 (m, 2H), 7.06–6.92 (m, 3H), 6.86–6.73 (m, 2H), 1.63 (d, 18H). In toluene solution (1 × 10⁻⁶) -5 The half-width at half maximum (WHM) is 22 nm.

[0149] Example 3: Synthesis of Compound 270:

[0150]

[0151] Preparation of intermediate K3:

[0152] Under nitrogen protection, starting material A2 (266 mg), intermediate J2 (495 mg), potassium tert-butoxide (168 mg), Pd2(dba)3 (46 mg), tri-tert-butylphosphine (30 mg), and 10 mL of anhydrous toluene were added to a three-necked flask, and the mixture was refluxed for 12 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate K3. LC-MS: Measured value: 679.09 ([M+H)) + Theoretical value: 678.22.

[0153] Preparation of intermediate P3:

[0154] Add raw material B3 (279 mg) and 50 mL of anhydrous DMF sequentially to a three-necked flask. Under nitrogen protection, add mineral oil-coated (65%) NaH (net content 29 mg) in portions under ice-water bath conditions. Stir the mixture for 0.5 hours, then slowly add intermediate K3 (679 mg) solution dissolved in 20 mL of anhydrous DMF. After the reaction is complete, quench the reaction with 100 mL of water and filter out the large amount of precipitate. Collect the precipitate, dry it with dichloromethane solution and anhydrous sodium sulfate, filter it, concentrate the reaction solution, and purify it by silica gel column chromatography using petroleum ether as the developing solvent to obtain intermediate P3. LC-MS: Measured value: 938.38 ([M+H) + Theoretical value: 937.42.

[0155] Preparation of compound 270:

[0156] In a sealed, pressure-resistant tube under nitrogen protection, intermediate P3 (939 mg) and 15 mL of anhydrous o-dichlorobenzene were added. After cooling to -78 °C, 30 mL of 2.5 M tert-butyllithium-n-hexane solution was added dropwise. The mixture was heated to 60 °C and reacted for 4 hours. The reaction was then cooled to -42 °C, and 1.5 mL of boron tribromide was added dropwise. After slowly restoring to room temperature, the reaction was allowed to continue for 8 hours. At 0 °C, 2.6 mL of ultra-dry N,N-diisopropylethylamine was added dropwise. The reaction mixture was heated to 180 °C and reacted for 48 hours. After cooling to room temperature, the low-boiling solvent was removed by vacuum distillation. The solution was dissolved in dichloromethane, filtered, dried over anhydrous sodium sulfate, and the filtrate was collected. The filtrate was concentrated and purified by column chromatography to give compound 270. Elemental analysis of the structure (C...) 67 H 54 BN3) Theoretical values: C, 88.24; H, 5.97; N, 4.61; Measured values: C, 88.21; H, 6.04; N, 4.64. LC-MS: Measured value: 912.23 ([M+H]) + Theoretical value: 911.44. 1 ¹H NMR (400MHz, Chloroform-d) δ 8.95 (d, 1H), 8.36 (m, 1H), 7.95 (m, 2H), 7.83 (m, 2H), 7.66–7.59 (m, 3H), 7.43 (m, 2H), 7.37–7.29 (m, 5H), 7.28–7.23 (m, 2H), 7.21 (d, 1H), 7.15 (m, 1H), 7.13–7.06 (m, 3H), 6.99–6.90 (m, 2H), 6.83–6.77 (m, 2H), 1.73 (s, 9H), 1.61 (d, 18H). In toluene solution (1×10⁻⁶) -5 The half-width at half maximum (WHM) is 23 nm.

[0157] Example 4: Synthesis of compound 282:

[0158]

[0159] Preparation of intermediate U2:

[0160] The following ingredients were added sequentially to a three-necked flask: N2 (99 mg), B4 (165 mg), CuI catalyst (10 mg), and K3PO4 (318 mg). Then, under a nitrogen atmosphere, trans-1,2-cyclohexanediamine (9 mg) and 30 mL of dioxane were added. The mixture was stirred at 110 °C for 16 hours. The reaction mixture was then cooled to room temperature, diluted with toluene, filtered through silica gel, and concentrated. The compound was separated by silica gel column chromatography (toluene:hexane = 1:2) to give intermediate U2. LC-MS: Measured value: 400.11 ([M+H) +Precision quality: 399.05.

[0161] Preparation of intermediate K4:

[0162] Under nitrogen protection, starting material A3 (347 mg), intermediate J1 (551 mg), potassium tert-butoxide (168 mg), Pd2(dba)3 (46 mg), tri-tert-butylphosphine (30 mg), and 20 mL of anhydrous toluene were added to a three-necked flask, and the mixture was refluxed for 12 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate K4. LC-MS: Measured value: 815.23 ([M+H) + Theoretical value: 814.18.

[0163] Preparation of intermediate Q4:

[0164] The following were added sequentially to a three-necked flask: starting material B5 (149 mg), intermediate K4 (816 mg), CuI catalyst (19 mg), and K3PO4 (637 mg). Then, under a nitrogen atmosphere, trans-1,2-cyclohexanediamine (29 mg) and 50 mL of dioxane were added. The mixture was stirred at 110 °C for 18 hours. The reaction mixture was then cooled to room temperature, diluted with toluene, filtered through silica gel, and concentrated. The compound was separated by silica gel column chromatography (toluene:hexane = 1:2) to obtain intermediate Q4. LC-MS: Measured value: 884.41 ([M+H) + Precision quality: 883.37.

[0165] Preparation of intermediate P4:

[0166] Intermediate U2 (399 mg), intermediate Q4 (885 mg), CuI catalyst (19 mg), and K3PO4 (637 mg) were added sequentially to a three-necked flask. Then, under a nitrogen atmosphere, trans-1,2-cyclohexanediamine (29 mg) and 50 mL of dioxane were added. The mixture was stirred at 110 °C for 16 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 (toluene:hexane = 1:2) to obtain intermediate P4. LC-MS: Measured value: 1155.54 ([M+H) + Precision quality: 1154.51.

[0167] Preparation of compound 282:

[0168] In a sealed, pressure-resistant tube under nitrogen protection, intermediate P4 (1156 mg) and 15 mL of anhydrous o-dichlorobenzene were added. After cooling to -78 °C, 30 mL of 2.5 M tert-butyllithium-n-hexane solution was added dropwise. The mixture was heated to 60 °C and reacted for 4 hours. The reaction was then cooled to -42 °C, and 1.5 mL of boron tribromide was added dropwise. After slowly restoring to room temperature, the reaction was allowed to continue for 8 hours. At 0 °C, 2.6 mL of ultra-dry N,N-diisopropylethylamine was added dropwise. The reaction mixture was heated to 180 °C and reacted for 48 hours. After cooling to room temperature, the low-boiling solvent was removed by vacuum distillation. The solution was dissolved in dichloromethane, filtered, dried over anhydrous sodium sulfate, and the filtrate was collected. The filtrate was concentrated and purified by column chromatography to obtain compound 282. Elemental analysis of the structure (C...) 83 H 65 BN4) Theoretical values: C, 88.28; H, 5.80; N, 4.96; Measured values: C, 88.22; H, 5.78; N, 5.01. LC-MS: Measured value: 1129.57 ([M+H]) + Theoretical value: 1128.53. In toluene solution (1×10⁻⁶) -5 The half-width at half maximum (WHM) is 20 nm.

[0169] Note: Half-width at half-maximum (FWHM) was measured using a Horiba Fluorolog-3 series fluorescence spectrometer.

[0170] Device Examples

[0171] The following describes in detail the application effects of the OLED material synthesized in the present invention in devices through device examples 1-4 and device comparative examples 1-3. Device examples 2-4 and device comparative examples 1-3 of the present invention have the same fabrication process as device example 1, and use the same substrate material and electrode material, with the same electrode film thickness. The only difference is the replacement of the light-emitting layer material in the device. The layer structure and test results of each device example are shown in Tables 1 and 2, respectively.

[0172] Device Example 1

[0173] like Figure 1As shown, the transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (film thickness 150nm) is washed sequentially with a cleaning agent (Semiclean M-L20), followed by washing with pure water, drying, and then ultraviolet-ozone washing to remove organic residues from the transparent ITO surface. After the above washing, HT-1 and HI-1 with a thickness of 10nm are deposited on the ITO anode layer 2 using a vacuum evaporation apparatus as a hole injection layer 3, with a mass ratio of HT-1 to HI-1 of 97:3. Next, a 60nm thick layer of HT-1 is deposited as a hole transport layer 4. Subsequently, a 30nm thick layer of EB-1 is deposited as an electron blocking layer 5. After the electron blocking materials are deposited, the light-emitting layer 6 of the OLED light-emitting device is fabricated, using GH-1 and GH-2 as the host materials and compound 28 as the dopant material, with a mass ratio of GH-1, GH-2, and compound 28 of 69:30:1, and 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.

[0174] The application effects of the OLED materials synthesized in this invention in devices are described in detail below through device examples 5-8 and device comparative examples 4-6. The fabrication processes of device examples 6-8 and device comparative examples 4-6 are exactly the same as those of device example 5, and the same substrate materials 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 1 and 2, respectively.

[0175] Device Example 5

[0176] The transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (film thickness 150nm) is washed sequentially with a cleaning agent (Semiclean M-L20), followed by washing with pure water, drying, and then ultraviolet-ozone washing to remove organic residues from the transparent ITO surface. After the above washing, a 10nm thick layer of HT-1 and HI-1 is deposited on the ITO anode layer 2 using a vacuum evaporation apparatus as a hole injection layer 3, with a mass ratio of HT-1 to HI-1 of 97:3. Next, a 60nm thick layer of HT-1 is deposited as a hole transport layer 4. Finally, a 30nm thick layer of EB-1 is deposited as an electron blocking layer 5. After the electron blocking material is deposited, the emitting layer 6 of the OLED light-emitting device is fabricated. GH-1 and GH-2 are used as the host materials, GD-1 is used as the first dopant, and compound 28 is used as the second dopant. The mass ratio of GH-1, GH-2, GD-1, and compound 28 is 66:30:3:1, and the thickness of the emitting layer is 30 nm. After the emitting layer 6, HB-1 is vacuum-deposited to a thickness of 5 nm; this layer is the hole blocking layer 7. After the hole blocking layer 7, ET-1 and Liq are vacuum-deposited to a mass ratio of 1:1; the thickness of this layer is 30 nm; this layer is the electron transport layer 8. On the electron transport layer 8, a LiF layer with a thickness of 1 nm is fabricated using a vacuum evaporation apparatus; this layer is the electron injection layer 9. On the electron injection layer 9, a Mg:Ag electrode layer with a thickness of 80 nm is fabricated using a vacuum evaporation apparatus; the mass ratio of Mg to Ag is 1:9; this layer is used as the cathode layer 10.

[0177] The molecular structural formulas of the relevant materials are shown below:

[0178]

[0179] After completing the OLED light-emitting device as described above, the anode and cathode are connected using a known driving circuit, and the current efficiency and lifetime of the device are measured. Examples and comparative examples of devices prepared using the same method are shown in Table 1; the test results for the current efficiency and lifetime of the obtained devices are shown in Table 2.

[0180] Table 1

[0181]

[0182]

[0183] Table 2

[0184]

[0185] Note: Current efficiency and emission peak were measured using an IVL (current-voltage-brightness) testing system (Suzhou Fushida Scientific Instruments Co., Ltd.); the lifetime testing system was the EAS-62C OLED device lifetime tester from System Technology Inc., Japan; LT95 refers to the time it takes for the device brightness to decay to 95%; all data are within 10 mA / cm². 2 Next test.

[0186] As can be seen from the device data results in Table 2, compared with the devices in Comparative Examples 1-6, the organic light-emitting devices of the present invention achieve significant improvements in current efficiency and lifetime compared with OLED devices made of known materials, whether in a single-doped or double-doped system; when using an exciton-sensitized material as the first dopant, the device efficiency is significantly improved compared with the single-doped system.

[0187] 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 resonance type organic compound, characterized by comprising: The structure of the resonance type organic compound is shown in any one of general formula (1): In general formula (1), Z is represented as C-H or C-R a ; R a each occurrence is the same or different represents a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C3-C 30 heteroaryl group; Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8are each independently C-H or C-R b ; R b Each instance of the same or different element is represented by a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1-C group. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted aromatic amino, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups; X independently represents O, S, N-(R c ); R c substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl; The M1 is represented by any one of the following ring structures: R1, R2, R3, R4, R5, R6, and R7 are independently represented as hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C atom, respectively. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted aromatic amino, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups; The substituents used for the substituent groups are optionally selected from halogen atoms, deuterium atoms, cyano groups, C1-C... 10 Alkyl, C1-C 10 alkoxy groups, C3-C 20 cycloalkyl, C6-C 30 Aryl, C3-C 30 One or more of the heteroaryl groups; The heteroatom in the heteroaryl group is optionally selected from one of O, S, N, Si.

2. The resonant organic compound according to claim 1, characterized by The structure of the resonance type organic compound is shown in any one of general formula (1-1) to general formula (1-3): In general formula (1-1) to general formula (1-3), the M1, Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8, R1, R2, R3, R4, R5, R6, R7 are defined as in claim 1. Z is represented by C-H or C-R a ; R a Each instance of the same or different element is represented by a deuterium atom, a halogen atom, a cyano group, or a C1-C group. 10 Alkyl, C3-C 10 cycloalkyl, C6-C 30 aryl, C3-C 30 It is one of the heteroaryl groups.

3. The resonant organic compound according to claim 1, wherein The structure of the resonance type organic compound is shown in any one of general formula (2-1) to general formula (2-5): In general formula (2-1) to general formula (2-5), the X, M1, Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8, R4, R5, R6, R7 are defined as in claim 1. Z is represented by C-H or C-R a ; R a Each instance of the same or different element is represented by a deuterium atom, a halogen atom, a cyano group, or a C1-C group. 10 Alkyl, C3-C 10 cycloalkyl, C6-C 30 aryl, C3-C 30 It is one of the heteroaryl groups.

4. The resonant organic compound according to claim 1, wherein The structure of the resonance type organic compound is shown in any one of general formula (3-1) to general formula (3-2): In general formula (3-1) to general formula (3-2), the Z, Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8, R1, R2, R3, R4, R5, R6, R7, X are defined as in claim 1. The X1 is represented by O or S; R8, R9, R 10 , R 11 each independently represents one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted arylamine group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C3-C 30 heteroaryl group; The substituents used for the substituent groups are optionally selected from halogen atoms, deuterium atoms, cyano groups, C1-C... 10 Alkyl, C3-C 20 cycloalkyl, C6-C 30 Aryl, C3-C 30 One or more of the heteroaryl groups; The heteroatom in the heteroaryl group is optionally selected from one of O, S, N, Si.

5. A resonance type organic compound, characterized by comprising: The structure of the resonance type organic compound is shown in any one of general formula (3-3) to general formula (3-5): In General Formula (3-3) to General Formula (3-5), Z is represented by C-H or C-R a ; R a Each instance of the same or different element is represented by a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1-C group. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted aromatic amino, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups; Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8are each independently C-H or C-R b ; R b Each instance of the same or different element is represented by a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1-C group. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted aromatic amino, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups; R1, R2, R3, R4, R5, R6, and R7 are independently represented as hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C atom, respectively. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted aromatic amino, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups; R8, R9, R 10 , R 11 , R 12 , R 13 , R 14 each independently represents one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C3-C 30 heteroaryl group; The substituents for the substituent groups are optionally one or more selected from the group consisting of a halogen atom, a deuterium atom, a cyano group, a C1-C6 10 alkyl group, a C3-C6 20 cycloalkyl group, a C1-C6 10 alkoxy group, a C6-C10 30 aryl group, a C3-C10 30 heteroaryl group; The heteroatom in the heteroaryl group is optionally selected from one of O, S, N, Si.

6. The resonant organic compound according to claim 1, wherein The R1, R3, R4, R5, R6, R7, each occurrence, are the same or different and represent a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted triazinyl group; R a , R b each occurrence, the same or different, represents a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted triazinyl group; R c substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolyl, substituted or unsubstituted furanyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl; The M1 is represented by one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group; The substituents for the substituent group are optionally one or more of a deuterium atom, a chlorine atom, a fluorine atom, an adamantyl group, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-pentyl group, a tert-butyl group, a butyl group, a methoxy group, a biphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a pyridazyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalyl group, a quinolyl group, an isoquinolyl group, a furanyl group, a thienyl group, an indolyl group, a pyrrolyl group, a dibenzofuranyl group, a dibenzothienyl group, a 9,9-dimethylfluorenyl group, a spirofluorenyl group, a carbazolyl group, an N-phenylcarbazolyl group, a carbazolinyl group, a phenanthrolinyl group.

7. The resonant organic compound according to claim 2, wherein The R1, R3, R4, R5, R6, R7, each occurrence, are represented by a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted triazinyl group; R a each occurrence, identically or differently, represents a deuterium atom, a halogen atom, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a cyclohexyl group, an adamantyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyridyl group, a quinolyl group, a furanyl group, a thienyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, a spirofluorenyl group, a triazinyl group; R b each occurrence, identically or differently, represents a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted triazinyl group; The M1 is represented by one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group; The substituents for the substituent group are optionally one or more of a deuterium atom, a chlorine atom, a fluorine atom, an adamantyl group, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-pentyl group, a tert-butyl group, a butyl group, a methoxy group, a biphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a pyridazyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalyl group, a quinolyl group, an isoquinolyl group, a furanyl group, a thienyl group, an indolyl group, a pyrrolyl group, a dibenzofuranyl group, a dibenzothienyl group, a 9,9-dimethylfluorenyl group, a spirofluorenyl group, a carbazolyl group, an N-phenylcarbazolyl group, a carbazolinyl group, a phenanthrolinyl group.

8. The resonant organic compound according to claim 3, wherein R4, R5, R6, R7, each occurrence, identically or differently, represent a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted triazinyl group; R a each occurrence, identically or differently, represents a deuterium atom, a halogen atom, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a cyclohexyl group, an adamantyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyridyl group, a quinolyl group, a furanyl group, a thienyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, a spirofluorenyl group, a triazinyl group; R b each occurrence, identically or differently, represents a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted triazinyl group; The R c The following are represented as substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiophenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl; M1represents one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group; the substituents for the substituent group are optionally one or more of a deuterium atom, a chlorine atom, a fluorine atom, an adamantyl group, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-pentyl group, a tert-butyl group, a butyl group, a methoxy group, a phenyl group, a biphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalyl group, a quinolyl group, an isoquinolyl group, a furanyl group, a thienyl group, an indolyl group, a pyrrolyl group, a dibenzofuranyl group, a dibenzothienyl group, a 9,9-dimethylfluorenyl group, a spirofluorenyl group, a carbazolyl group, a N-phenylcarbazolyl group, a carbazolinyl group, a phenanthrolinyl group.

9. The resonant organic compound according to claim 4, wherein R1, R3, R4, R5, R6, R7, R8, R9, R 10 , R 11 each occurrence, the same or different, represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted triazinyl group; R a , R b each occurrence, the same or different, represents a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted triazinyl group; R c substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolyl, substituted or unsubstituted furanyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl; the substituents for the substituent group are optionally one or more of a deuterium atom, a chlorine atom, a fluorine atom, an adamantyl group, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-pentyl group, a tert-butyl group, a butyl group, a methoxy group, a phenyl group, a biphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalyl group, a quinolyl group, an isoquinolyl group, a furanyl group, a thienyl group, an indolyl group, a pyrrolyl group, a dibenzofuranyl group, a dibenzothienyl group, a 9,9-dimethylfluorenyl group, a spirofluorenyl group, a carbazolyl group, a N-phenylcarbazolyl group, a carbazolinyl group, a phenanthrolinyl group.

10. The resonant organic compound according to claim 5, wherein R1, R3, R4, R5, R6, R7, R8, R9, R 10 , R 11 , R 12 , R 13 , R 14 each occurrence, the same or different, represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted triazinyl group; R a , R b each occurrence, the same or different, represents a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted triazinyl group; R c substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolyl, substituted or unsubstituted furanyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl; the substituents for the substituent group are optionally one or more of a deuterium atom, a chlorine atom, a fluorine atom, an adamantyl group, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-pentyl group, a tert-butyl group, a butyl group, a methoxy group, a phenyl group, a biphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalyl group, a quinolyl group, an isoquinolyl group, a furanyl group, a thienyl group, an indolyl group, a pyrrolyl group, a dibenzofuranyl group, a dibenzothienyl group, a 9,9-dimethylfluorenyl group, a spirofluorenyl group, a carbazolyl group, a N-phenylcarbazolyl group, a carbazolinyl group, a phenanthrolinyl group.

11. The resonant organic compound according to claim 1, wherein The R a , R b is represented as a structure shown below: Any one of them; R1, R2, R3, R4, R5, R6, R7are represented by the following structures: a hydrogen atom, Any one of them; The R c is represented as a structure shown below: Any of the foregoing.

12. The resonant organic compound according to claim 2, wherein The R a is represented as a structure shown below: any of the following: The R b is represented as a structure shown below: Any one of them; R1, R2, R3, R4, R5, R6, R7are represented by the following structures: a hydrogen atom, Any of the foregoing.

13. The resonant organic compound according to claim 3, wherein The R a is represented as a structure shown below: Any one of them; The R b is represented as a structure shown below: Any one of them; R1, R2, R3, R4, R5, R6, R7are represented by the following structures: a hydrogen atom, Any one of; the R c is represented as a structure shown below: Any of the foregoing.

14. The resonant organic compound according to claim 4, wherein The R a , R b is represented as a structure shown below: Any one of them; R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 , R 11 are represented as structures shown below: a hydrogen atom, Any one of them; The R c is represented as a structure shown below: Any of the foregoing.

15. The resonant organic compound according to claim 5, wherein The R a , R b is represented as a structure shown below: Any one of them; R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 , R 11 , R 12 , R 13 , R 14 are represented as structures shown below. a hydrogen atom, Any one of them; The R c is represented by the structure shown below: Any of the foregoing.

16. The resonant organic compound according to claim 1, wherein The substituted or unsubstituted C6-C 30 Aryl groups refer to substituted or unsubstituted phenyl groups, substituted or unsubstituted naphthyl groups, substituted or unsubstituted anthraquinyl groups, substituted or unsubstituted fluorenyl groups, substituted or unsubstituted dimethylfluorenyl groups, substituted or unsubstituted diphenylfluorenyl groups, substituted or unsubstituted spirofluorenyl groups, substituted or unsubstituted phenanthrene groups, substituted or unsubstituted tetraphenyl groups, substituted or unsubstituted pyrene groups, substituted or unsubstituted biphenyl groups, substituted or unsubstituted para-triphenyl groups, substituted or unsubstituted meta-triphenyl groups, and substituted or unsubstituted phenyl groups. alkyl, substituted or unsubstituted triphenylene, substituted or unsubstituted perylene, substituted or unsubstituted indole; The substituted or unsubstituted C3-C 30 Heteroaryl refers to substituted or unsubstituted furanyl, substituted or unsubstituted thiophene, substituted or unsubstituted pyrrole, substituted or unsubstituted pyrazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted oxadiazolyl, substituted or unsubstituted thiadiazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted triazine, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophene, and substituted or unsubstituted benzene. Imidazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted naphthinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridineyl, substituted or unsubstituted benzazinyl, substituted or unsubstituted benzathiazinyl, substituted or unsubstituted benzazinyl, substituted or unsubstituted fumonyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl; The C1-C 10 Alkyl groups refer to methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, sec-butyl, neopentyl, n-pentyl, isopentyl, octyl, heptyl, n-decyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, and 1-butylpentyl. said C3-C 10 Cycloalkyl means cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl and cycloheptyl.

17. A resonant organic compound, characterized by, a hydrogen atom, 18. An organic light emitting device comprising a cathode, an anode, and a functional layer, the functional layer being located between the cathode and the anode, characterized in that, the specific structural formula of the resonance type organic compound is any one of the following structures:

19. The organic light emitting device of claim 18, wherein, the functional layer comprises a light emitting layer, the light emitting layer comprises a host material and a doping material, the doping material is the resonance type organic compound according to any one of claims 1-17.

20. The organic light emitting device of claim 18, wherein the light emitting layer comprises a host material, an exciton sensitizing material, and a dopant material. the light emitting layer comprises a first host material, a second host material and a doping material, at least one of the first host material and the second host material is a TADF material, and the doping material is the resonance type organic compound according to any one of claims 1-17. the exciton sensitization material is a complex containing a metal element, and the doping material is the resonance type organic compound according to any one of claims 1-17.

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