Resonant organic compound and use thereof

Abstract

The application relates to a resonance type organic compound and application thereof, and belongs to the technical field of semiconductors. The structure of the compound is shown in general formula (1). The compound has a narrow half-peak width and a high fluorescence quantum yield. When the compound is used as a doping material in a light-emitting layer material of an OLED light-emitting device, the current efficiency of the device is remarkably improved, and the light-emitting color purity and the device life are also greatly improved.

Description

TECHNICAL FIELD

[0001] The present application relates to the field of semiconductor technology, in particular to a resonance type organic compound and application thereof. BACKGROUND

[0002] The conventional fluorescent dopant material is limited by the early technology, and can only utilize 25% singlet exciton formed by electric excitation to emit light, the internal quantum efficiency of the device is low (the highest is 25%), and the external quantum efficiency is generally lower than 5%, which has a great gap with the efficiency of phosphorescent device. The phosphorescent material can effectively utilize singlet exciton and triplet exciton formed by electric excitation to emit light due to the strong spin-orbit coupling of heavy atom center, so that the internal quantum efficiency of the device reaches 100%.

[0003] With the coming of the 5G era, higher requirements are put forward for the color rendering standard, and the luminescent material needs to be high-efficiency, stable, and also needs to be narrower half-peak width to improve the color purity of device light emission. The fluorescent dopant material can realize high fluorescent quantum and narrow half-peak width through molecular engineering, and the blue fluorescent dopant material has achieved a breakthrough in stage, and the half-peak width of boron-based material can be reduced to below 30 nm; while the green light region which is more sensitive to human eyes, the research mainly focuses on phosphorescent dopant material, but it is difficult to narrow the emission peak shape by simple method, therefore, in order to meet the higher color rendering standard, it is of great significance to study the high-efficiency green fluorescent dopant material with narrow half-peak width.

[0004] In addition, the sensitization technology combines triplet exciton sensitization material with fluorescent dopant material, uses triplet exciton sensitization material as exciton sensitization medium, fully utilizes triplet exciton, and transfers energy to fluorescent dopant material through energy transfer, so that the internal quantum efficiency of the device reaches 100%. This technology can make up for the shortcomings of insufficient utilization rate of exciton of fluorescent dopant material, effectively play the characteristics of high fluorescent quantum yield, high device stability, high color purity and low cost of fluorescent dopant material, and has broad prospects in OLED application.

[0005] The boron-based compound with resonance structure is easier to realize narrow half-peak width emission, and the application of this kind of material in the sensitized fluorescent technology can realize the preparation of high-efficiency and narrow half-peak width emission device. In CN 107507921 A and CN 110492006 A, a luminescent layer combination technology is disclosed, in which the TADF material with a lowest singlet and triplet energy level difference less than or equal to 0.2eV is used as the host, and the boron-based material is used as the dopant; in CN 110492005 A and CN 110492009 A, a luminescent layer combination scheme is disclosed, in which the exciplex is used as the host, and the boron-based material is used as the dopant; both of them can realize the efficiency comparable to phosphorescent and relatively narrow half-peak width. Therefore, the development of the sensitization technology based on the narrow half-peak width boron-based luminescent material has unique advantages and strong potential in the face of BT.2020 display indicators. Summary of the Invention

[0006] To address the aforementioned problems in the existing technology, the applicant of this invention provides a resonance-type organic compound and its applications. In general formula (1), a resonance-type organic compound is formed by introducing a carbazole-indole fused ring structure, which has the significant effects of regulating light color, improving quantum yield, and increasing device lifetime.

[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 is represented as C-R1; each occurrence of R1, whether the same or different, is represented by H, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C. 10 Alkyl or silyl groups, substituted amino groups, substituted or unsubstituted C6-C groups 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl groups;

[0010] Ar1 represents C1-C with or without substitution. 10 Alkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl groups;

[0011] X is represented as C(R2)(R3), Si(R4)(R5), N(R6), O, S;

[0012] M1 indicates substituted or unsubstituted C6-C. 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl groups;

[0013] The presence of the same or different R2, R3, R4, and R5 each time indicates H, deuterium atom, substituted or unsubstituted C1-C atom. 10 Alkyl or silyl, substituted or unsubstituted C2-C 10 alkenyl, substituted amino, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl groups;

[0014] R6 indicates substituted or unsubstituted C1-C. 10 Alkyl or silyl, substituted or unsubstituted C2-C 10 alkenyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30The heteroaryl group; R6 can be linked with M1 to form a five- or six-membered heterocycle;

[0015] Z1, Z2, and Z3 represent CR respectively. a CR b CR c ;R a R b R c Each occurrence of the same or different C1-C is represented by H, substituted or unsubstituted C1-C. 10 Alkyl, alkenyl or silyl, substituted or unsubstituted amino, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl groups; and R a R b R c Not simultaneously represented as H; R a R b R c Each pair can be connected to form a loop;

[0016] The substituents used for the substituent groups are optionally selected from halogen atoms, deuterium atoms, cyano groups, C1-C... 10 Alkyl, 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;

[0017] The heteroatom in the heteroaryl group is selected from one of O, S, N, and Si.

[0018] The preferred structure of the resonance-type organic compound is shown in general formula (1-1):

[0019]

[0020] In general formula (1-1), the definitions of Z, M1, X, Z1, Z2, and Z3 are the same as those in the above-mentioned limitations.

[0021] Preferably, the structure of the resonance-type organic compound is shown in any one of general formulas (1-2) to (1-8):

[0022]

[0023]

[0024] In general formulas (1-2) to (1-8), the definitions of Z, Ar1, Z1, v2, and Z3 are the same as those defined above.

[0025] Ar2 and Ar3 represent substituted or unsubstituted C1-C. 10 Alkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl groups;

[0026] R7 and R8 represent hydrogen atoms, substituted or unsubstituted C1-C atoms. 10 Alkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl groups;

[0027] Y is represented as C(R2)(R3), Si(R4)(R5), N(R6), O, S;

[0028] The presence of the same or different R2, R3, R4, and R5 each time indicates H, deuterium atom, substituted or unsubstituted C1-C atom. 10 Alkyl or silyl, substituted or unsubstituted C2-C 10 alkenyl, substituted amino, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl groups;

[0029] R6 indicates substituted or unsubstituted C1-C. 10 Alkyl or silyl, substituted or unsubstituted C2-C 10 alkenyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl groups;

[0030] The substituents used for the substituent groups are optionally selected from halogen atoms, deuterium atoms, cyano groups, C1-C... 10 Alkyl, 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;

[0031] The heteroatom in the heteroaryl group is selected from one of O, S, N, and Si.

[0032] Preferably, the structure of the resonance-type organic compound is shown in any one of general formulas (2) to (6):

[0033]

[0034] In general formulas (2) to (6), the definitions of Z, M1, and X are the same as those in the above-mentioned limitations.

[0035] The preferred structures of the resonance-type organic compounds are shown in general formulas (7) to (14):

[0036]

[0037] In general formulas (7) to (14), the definitions of Z, Z1, Z2, and Z3 are the same as those in the above-mentioned limitations.

[0038] Preferably, M1 is represented as any of the following ring structures:

[0039]

[0040]

[0041] Preferably, R1, R a R b R c It can be represented as the structure shown below:

[0042] hydrogen atom, Any one of them;

[0043] Preferably, Ar1, Ar2, Ar3, R6, R7, and R8 are represented in the following structure:

[0044] Any one of them.

[0045] Preferably, R1, whether appearing the same or different, is represented by hydrogen, deuterium atom, tritium atom, halogen atom, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, etc. 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;

[0046] The recurrence of R2, R3, R4, and R5, whether identical or different, is represented by H, deuterium atom, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclohexyl, 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, or substituted or unsubstituted quinoline. Substituent or unsubstituted furanyl, substituted or unsubstituted thiophene, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amino, substituted or unsubstituted triazineyl;

[0047] The recurrence of R6, R7, and R8, whether identical or different, represents 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 vinyl, substituted or unsubstituted propenyl, 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 pyridine. The following compounds are listed: pyridyl, 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, and substituted or unsubstituted triazineyl.

[0048] The R a R b R cEach instance of the same or different is represented by H, deuterium atom, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted vinyl, substituted or unsubstituted propenyl, substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinone, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted Substituted quinolinyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amino, substituted or unsubstituted triazineyl;

[0049] Ar1, Ar2, and Ar3 represent phenyl or tert-butyl-substituted phenyl groups;

[0050] 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, and substituted or unsubstituted indole[3,2,1-jk]carbazoyl.

[0051] The substituents used for the substituent groups are selected from one or more of the following: deuterium, chlorine, fluorine, trifluoromethyl, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthrene, pyridinyl, pyrazinyl, pyrazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheneyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheninyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazoleyl, N-phenylcarbazoleyl, carbazolinyl, and azirphenanthreneyl.

[0052] Preferably, the specific structural formula of the resonance-type organic compound is any one of the following structures:

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062] An organic light-emitting device includes 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 any of the resonant organic compounds described above.

[0063] In a preferred embodiment, the functional layer includes a light-emitting layer, which is a resonant organic compound as described in any of the preceding embodiments.

[0064] 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 any of the resonant organic compounds described above.

[0065] 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 any of the above-mentioned resonant organic compounds.

[0066] Compared with the prior art, the beneficial technical effects of the present invention are as follows:

[0067] (1) The compound of the present invention can be used as a doping material for the light-emitting layer in OLED devices. It can emit fluorescence under the action of an electric field and can be applied to OLED lighting or OLED display fields.

[0068] (2) The compound of the present invention has a high fluorescence quantum efficiency as a doping material, and the fluorescence quantum efficiency of the material is close to 100%;

[0069] (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;

[0070] (4) The introduction of the carbazole indole fused ring structure is beneficial to further enhance the resonance effect of the molecule, which makes the emission spectrum of the material narrower.

[0071] (5) The introduction of the carbazole-indole fused ring structure can further improve the delocalization of the electron cloud, increase the oscillator strength of the excited state, and reduce the recombination energy of the molecule, thereby reducing the Stokes shift and narrowing the half-peak width.

[0072] The compounds of this invention have narrow half-width and high fluorescence quantum yield, 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

[0073] Figure 1 This is a schematic diagram of the structure of an OLED device in which the materials listed in this invention are applied;

[0074] 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

[0075] The present invention will now be described in detail with reference to the accompanying drawings and embodiments.

[0076] 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.

[0077] 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.

[0078] In this invention, C3-C is substituted or unsubstituted. 30 Heteroaryl refers to substituted or unsubstituted furanyl, substituted or unsubstituted thiophene, substituted or unsubstituted pyrrole, substituted or unsubstituted pyrazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted oxadiazolyl, substituted or unsubstituted thiadiazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted triazine, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophene, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted... The fused ring of substituted indolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted naphridyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridineyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenthiazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted fumonyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoleyl, combinations thereof, or combinations of the foregoing groups, but not limited thereto.

[0079] 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.

[0080] The C3-C of this invention 20 Cycloalkyl refers to a monovalent monocyclic saturated hydrocarbon group comprising 3 to 20 carbon atoms as cyclic atoms. In this document, C5-C is preferred. 10 Cycloalkyl. Non-limiting examples may include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl and cycloheptyl.

[0081] 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; opaque substrates, such as silicon substrates; and flexible PI film substrates. Different substrates have different mechanical strengths, thermal stability, transparency, surface smoothness, and water resistance. Their application varies depending on their properties. In this invention, a transparent substrate is preferred. There are no particular limitations on the thickness of the substrate.

[0082] 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.

[0083] 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.

[0084] 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.

[0085] 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.

[0086] 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.

[0087] Furthermore, depending on the device configuration requirements, the hole transport film layer between the hole transport auxiliary layer and the hole injection layer of the 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.

[0088] 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.

[0089] 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.

[0090] 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.

[0091] 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.

[0092] 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.

[0093] 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.

[0094] The thickness of the electron blocking layer of the present invention can be 1-20 nm, preferably 5-10 nm, but the thickness is not limited to this range.

[0095] 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.

[0096] 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.

[0097] 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.

[0098] 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 15-30 nm, but the thickness is not limited to this range.

[0099] 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.

[0100] 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, and pyrimidine derivatives such as 9,9′-(5-(6-([1,1′-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-1,3-phenylene)bis(9H-carbazole) (CAS No.: 1345338-69-3), etc. The thickness of the hole blocking layer of the present invention can be 2-200 nm, preferably 5-150 nm and more preferably 10-100 nm, but the thickness is not limited to this range.

[0101] 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.

[0102] 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.

[0103] 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, typically 10-50 nm, preferably 15-20 nm.

[0104] 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.

[0105] 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.

[0106] Synthesis Examples

[0107] All raw materials involved in the synthesis embodiments of the present invention can be purchased from the market or obtained by conventional preparation methods in the art;

[0108] Example 1: Synthesis of Compound 58:

[0109]

[0110] Preparation of intermediate J1:

[0111] In a three-necked flask under nitrogen protection, starting material M1 (20.0 mmol) and (Boc)₂O (25.0 mmol) were dissolved in 250 mL of tetrahydrofuran. 5 mmol of DMAP (4-dimethylaminopyridine) was added, and the mixture was stirred at room temperature for 2 h. The suspension was filtered, and the solid was washed with 100 mL of tetrahydrofuran and 200 mL of ethyl acetate to obtain intermediate J1. LC-MS: Measured value: 357.28 ([M+H) + Theoretical value: 356.15.

[0112] Preparation of intermediate J2:

[0113] Intermediate J1 (20.0 mmol), starting material N1 (25.0 mmol), CuI catalyst (3 mmol), and K3PO4 (55 mmol) were added sequentially to a three-necked flask. Then, under a nitrogen atmosphere, 4 mmol of trans-1,2-cyclohexanediamine and 180 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 J2. LC-MS: Measured value: 489.38 ([M+H)). +Theoretical value: 488.25.

[0114] Preparation of intermediate J3:

[0115] Intermediate J2 (25.0 mmol) was added to a single-necked flask and heated at 230 °C for 1.5 h. The molten solid was cooled and purified by MPLC with silica gel and heptane / ethyl acetate to obtain intermediate J3. LC-MS: Measured value: 389.35 ([M+H)). + Theoretical value: 388.19.

[0116] Preparation of intermediate K1:

[0117] The following were added sequentially to a three-necked flask: starting material A1 (15.0 mmol), intermediate J3 (15.0 mmol), CuI catalyst (2 mmol), and K3PO4 (45 mmol). Then, under a nitrogen atmosphere, 3 mmol of trans-1,2-cyclohexanediamine and 160 mL of dioxane were added. The mixture was stirred at 110 °C for 15 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 K1. LC-MS: Measured value: 633.22 ([M+H) + Theoretical value: 632.16.

[0118] Preparation of intermediate P1:

[0119] The following were added sequentially to a three-necked flask: starting material B1 (15.0 mmol), intermediate K1 (15.0 mmol), CuI catalyst (2 mmol), and K3PO4 (45 mmol). Then, under a nitrogen atmosphere, 3 mmol of trans-1,2-cyclohexanediamine and 160 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 compounds were separated by silica gel column chromatography (toluene:hexane = 1:2) to obtain intermediate P1. LC-MS: Measured value: 702.41 ([M+H) + Theoretical value: 701.35.

[0120] Preparation of intermediate Q1:

[0121] The following were added sequentially to a three-necked flask: starting material C1 (15.0 mmol), intermediate P1 (15.0 mmol), CuI catalyst (2 mmol), and K3PO4 (45 mmol). Then, under a nitrogen atmosphere, 3 mmol of trans-1,2-cyclohexanediamine and 160 mL of dioxane were added. The mixture was stirred at 110 °C for 20 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 Q1. LC-MS: Measured value: 941.57 ([M+H) + Theoretical value: 940.43.

[0122] Preparation of compound 58:

[0123] Intermediate Q1 (5.0 mmol) and tert-butylbenzene (50 mL) were added sequentially to a low-temperature flask. The mixture was cooled to -78 °C, and a hexane solution of n-butyllithium (5.5 mmol) 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 gas was then introduced for protection, and after 2 hours of reaction, BBr3 (6.0 mmol) was added at -42 °C. The mixture was stirred for 2 hours and then slowly brought to room temperature. After stirring at room temperature for 10 hours, DIPEA (N,N-diisopropylethylamine) (10 mmol) was added under ice-water bath conditions, and the mixture was heated to 120 °C and refluxed for 36 hours. The reaction was cooled to room temperature, and the solution was filtered through diatomaceous earth. The organic phase was collected, and the high-boiling solvent was removed by vacuum distillation. The solution was dissolved in dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography. Toluene was used as the developing solvent to obtain compound 58. LC-MS: Measured value: 915.52 ([M+H]+), theoretical value: 914.45. 1 ¹H NMR (400MHz, Chloroform-d) δ 8.24–8.17 (m, 2H), 7.98–7.87 (m, 2H), 7.63 (m, 4H), 7.44–7.25 (m, 11H), 7.24–7.15 (m, 3H), 7.13–7.07 (m, 2H), 7.05–6.98 (m, 3H), 6.93 (d, 1H), 1.34–1.27 (m, 27H). In toluene solution (1×10⁻⁶) -5 The half-width at half maximum (WHM) is 26 nm.

[0124] Example 2: Synthesis of compound 72:

[0125]

[0126]

[0127] Preparation of intermediate K2:

[0128] The synthesis of intermediate K2 is based on intermediate K1, except that intermediate J3 is replaced with starting material D1 to obtain intermediate K2. LC-MS: Measured value: 564.28 ([M+H)) + Theoretical value: 563.10.

[0129] Preparation of intermediate P2:

[0130] The synthesis of intermediate P2 is based on intermediate P1, except that starting material B2 replaces starting material B1, and intermediate K2 replaces intermediate K1, yielding intermediate P2. LC-MS: Measured value: 765.44 ([M+H)) + Theoretical value: 764.39.

[0131] Preparation of intermediate Q2:

[0132] Intermediate Q2 was synthesized using the same method as intermediate Q1, except that intermediate P2 was used instead of intermediate P1 to obtain intermediate Q2. LC-MS: Measured value: 1004.37 (M+H) + Theoretical value: 1003.46.

[0133] Preparation of compound 72:

[0134] The synthesis of compound 72 was based on compound 58, except that intermediate Q1 was replaced with intermediate Q2, yielding compound 72. LC-MS: Measured value: 978.53 ([M+H]+), theoretical value: 977.49. In toluene solution (1×10⁻⁶) -5 The full width at half maximum (FWHM) is 21 nm.

[0135] Example 3: Synthesis of Compound 79:

[0136]

[0137] Preparation of intermediate K3:

[0138] The synthesis of intermediate K3 referenced intermediate K1, except that intermediate J3 was replaced with starting material D2. LC-MS: Measured value: 579.23 ([M+H)) + Theoretical value: 578.11.

[0139] Preparation of intermediate P3:

[0140] Intermediate P3 was synthesized using intermediate P1 as a reference, except that intermediate K3 was used instead of intermediate K1 to obtain intermediate P3. LC-MS: Measured value: 648.45 (M+H) +Theoretical value: 647.31.

[0141] Preparation of intermediate Q3:

[0142] Intermediate Q3 was synthesized using the same method as intermediate Q1, except that intermediate P1 was replaced with intermediate P3 to obtain intermediate Q3. LC-MS: Measured value: 887.27 (M+H) + Theoretical value: 886.38.

[0143] Preparation of compound 79:

[0144] The synthesis of compound 79 was based on compound 58, except that intermediate Q1 was replaced by intermediate Q3, resulting in compound 79. LC-MS: Measured value: 861.39 ([M+H]+), theoretical value: 860.41. 1 ¹H NMR (400 MHz, Chloroform-d) δ 8.20 (m, 1H), 8.00–7.84 (m, 2H), 7.69–7.57 (m, 3H), 7.42–7.16 (m, 12H), 7.15–6.96 (m, 12H), 6.93 (d, 1H), 1.30 (d, 18H). In toluene solution (1 × 10⁻⁶) -5 The half-width at half maximum (WHM) is 25 nm.

[0145] Example 4: Synthesis of Compound 116:

[0146]

[0147] Preparation of intermediate K4:

[0148] Intermediate K4 was synthesized using the same method as intermediate K1, except that intermediate J3 was replaced by starting material D1 and starting material A1 was replaced by starting material A2. LC-MS: Measured value: 584.21 ([M+H)) + Theoretical value: 583.07.

[0149] Preparation of intermediate P4:

[0150] The synthesis of intermediate P4 referenced intermediate P1, except that starting material B2 replaced starting material B1, and intermediate K4 replaced intermediate K1, yielding intermediate P4. LC-MS: Measured value: 785.44 ([M+H)) + Theoretical value: 784.36.

[0151] Preparation of intermediate Q4:

[0152] Intermediate Q4 was synthesized using the same method as intermediate Q1, except that intermediate P4 was used instead of intermediate P1 to obtain intermediate Q4. LC-MS: Measured value: 1024.29 (M+H) + Theoretical value: 1023.43.

[0153] Preparation of compound 116:

[0154] The synthesis of compound 116 is based on compound 58, except that intermediate Q1 is replaced by intermediate Q4, yielding compound 116. LC-MS: Measured value: 998.57 ([M+H]+), theoretical value: 997.46. In toluene solution (1×10⁻⁶) -5 The half-width at half maximum (WHM) is 23 nm.

[0155] Example 5: Synthesis of Compound 123:

[0156]

[0157] Preparation of intermediate K5:

[0158] Intermediate K5 was synthesized using the same method as intermediate K1, except that intermediate J3 was replaced by starting material D3 and starting material A1 was replaced by starting material A3. LC-MS: Measured value: 470.28 (M+H) + Theoretical value: 469.12.

[0159] Preparation of intermediate P5:

[0160] Intermediate P5 was synthesized using intermediate P1 as a reference, except that intermediate K5 was used instead of intermediate K1 to obtain intermediate P5. LC-MS: Measured value: 539.39 (M+H) + Theoretical value: 538.31.

[0161] Preparation of intermediate Q5:

[0162] Intermediate Q5 was synthesized using the same method as intermediate Q1, except that intermediate P5 was used instead of intermediate P1 to obtain intermediate Q5. LC-MS: Measured value: 778.45 (M+H) + Theoretical value: 777.38.

[0163] Preparation of intermediate L1:

[0164] The synthesis of intermediate L1 is based on reference compound 58, except that intermediate Q1 is replaced by intermediate Q5 to obtain intermediate L1. LC-MS: Measured value: 752.34 ([M+H]+), theoretical value: 751.41.

[0165] Preparation of intermediate T1:

[0166] Intermediate L1 (10.0 mmol), pinacol diboronate (15 mmol), [Ir(COD)(OCH3)]2 (0.06 mmol), and 150 mL of tetrahydrofuran were added sequentially to a single-necked flask. The reaction was carried out at room temperature for 12 hours under nitrogen protection. The reaction was then filtered, the organic phase was concentrated, and the compounds were separated by silica gel column chromatography using petroleum ether:ethyl acetate = 1:1 as the developing solvent to obtain intermediate T1. This reaction exhibited relatively good selectivity (refer to DOI: 10.31635 / ccschem.021.202101033), with boron-p-boron esters showing even higher activity and selectivity. LC-MS: Measured value: 878.55 ([M+H) + Theoretical value: 877.49.

[0167] Preparation of compound 123:

[0168] Intermediate T1 (10.0 mmol), starting material E1 (10.0 mmol), Pd(PPh3)4 catalyst (0.1 mmol), 150 mL of tetrahydrofuran:water = 10:1 mixed solution, and potassium carbonate (20 mmol) were added sequentially to a two-necked flask. The mixture was then stirred at 80 °C for 5.5 hours under nitrogen protection. After cooling, the liquid-liquid phase was separated and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The compound was separated by silica gel column chromatography using petroleum ether:ethyl acetate = 5:1 as the developing solvent to obtain compound 123. LC-MS: Measured value: 983.57 ([M+H) + Theoretical value: 982.49. 1 ¹H NMR (400MHz, Chloroform-d) δ 8.67–8.54 (m, 4H), 8.26–8.16 (m, 1H), 8.00–7.90 (m, 1H), 7.68–7.60 (m, 2H), 7.59–7.47 (m, 6H), 7.42–7.22 (m, 5H), 7.18–6.95 (m, 11H), 6.74 (s, 2H), 2.58–1.98 (m, 27H). In toluene solution (1×10⁻⁶) -5 The half-width at half maximum (WHM) is 27 nm.

[0169] Example 6: Synthesis of Compound 147:

[0170]

[0171] Preparation of intermediate K6:

[0172] In a three-necked flask, starting material A3 (12.0 mmol), starting material B1 (20.0 mmol), CuI catalyst (3 mmol), and K3PO4 (45 mmol) were added sequentially. Then, under a nitrogen atmosphere, 4 mmol of trans-1,2-cyclohexanediamine and 160 mL of dioxane were added. The mixture was stirred at 110 °C for 19 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 K6. LC-MS: Measured value: 407.28 ([M+H) + Theoretical value: 406.22.

[0173] Preparation of intermediate P6:

[0174] The following were added sequentially to a three-necked flask: starting material C1 (24.0 mmol), intermediate K6 (12.0 mmol), CuI catalyst (3 mmol), and K3PO4 (45 mmol). Then, under a nitrogen atmosphere, 4 mmol of trans-1,2-cyclohexanediamine and 160 mL of dioxane were added. The mixture was stirred at 110 °C for 20 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 give intermediate P6. LC-MS: Measured value: 885.40 ([M+H)). + Theoretical value: 884.36.

[0175] Preparation of intermediate L2:

[0176] The synthesis of intermediate L2 is based on reference compound 58, except that intermediate Q1 is replaced by intermediate P6 to obtain intermediate L2. LC-MS: Measured value: 859.27 ([M+H]+), theoretical value: 858.39.

[0177] Preparation of intermediate T2:

[0178] Intermediate T2 was synthesized using intermediate T1 as a reference, except that intermediate L1 was replaced with intermediate L2. LC-MS: Measured value: 985.51 ([M+H)) + Theoretical value: 984.47.

[0179] Preparation of compound 147:

[0180] Compound 147 was synthesized using the same method as compound 123, except that intermediate T1 was replaced with intermediate T2. LC-MS: Measured value: 1090.56 ([M+H)). + Theoretical value: 1089.47. 1¹H NMR (400 MHz, Chloroform-d) 68.71–8.50 (m, 4H), 8.20 (m, 2H), 8.03–7.87 (m, 2H), 7.70–7.48 (m, 10H), 7.44–7.23 (m, 8H), 7.16–7.07 (m, 4H), 7.05–6.95 (m, 6H), 6.74 (s, 2H), 1.31 (s, 18H). In toluene solution (1 × 10⁻⁶) -5 The half-width at half maximum (WHM) is 25 nm.

[0181] Example 7: Synthesis of Compound 191:

[0182]

[0183] Preparation of intermediate K7:

[0184] Intermediate K7 was synthesized using the same method as intermediate K1, except that intermediate J3 was replaced by reactant D4 and reactant A1 was replaced by reactant A4. LC-MS: Measured value: 600.28 (M+H) + Theoretical value: 599.18.

[0185] Preparation of intermediate P7:

[0186] Intermediate P7 was synthesized using intermediate P1 as a reference, except that intermediate K7 was used instead of intermediate K1 to obtain intermediate P7. LC-MS: Measured value: 669.41 ([M+H)) + Theoretical value: 668.38.

[0187] Preparation of intermediate Q7:

[0188] Intermediate Q7 was synthesized using the same method as intermediate Q1, except that intermediate P7 was used instead of intermediate P1 to obtain intermediate Q7. LC-MS: Measured value: 908.53 ([M+H)). + Theoretical value: 907.45.

[0189] Preparation of compound 191:

[0190] In a three-necked flask under nitrogen protection, 2 mmol of boron tribromide and 1 mmol of intermediate Q7 were dissolved in 30 mL of 1,2,4-trichlorobenzene. After stirring at 180 °C for 24 hours, the reaction mixture was diluted with 50 mL of dichloromethane, and 100 mL of sodium phosphate buffer (pH 6) was added at 0 °C. The aqueous layer was separated and extracted three times with 100 mL of dichloromethane. The crude product was purified by silica gel column chromatography (eluent: hexane / CH2Cl2 = 5 / 1), washed with acetonitrile and GPC (eluent: 1,2-dichloromethane) to give the target compound 191. LC-MS: Measured value: 916.48 ([M+H) + Precision quality: 915.44. 1 ¹H NMR (400MHz, Chloroform-d) δ 8.20 (m, 2H), 7.98–7.87 (m, 2H), 7.66–7.52 (m, 6H), 7.48–7.41 (m, 2H), 7.40–7.34 (m, 1H), 7.34–7.25 (m, 4H), 7.17 (m, 1H), 7.14–7.07 (m, 4H), 7.06–6.98 (m, 5H), 1.37–1.29 (m, 27H). In toluene solution (1×10⁻⁶) -5 The half-width at half maximum (WHM) is 24 nm.

[0191] Example 8: Synthesis of Compound 197:

[0192]

[0193] Preparation of intermediate K8:

[0194] Intermediate K8 was synthesized using the same method as intermediate K1, except that intermediate J3 was replaced by starting material D5 and starting material A1 was replaced by starting material A4. LC-MS: Measured value: 536.25 (M+H) + Theoretical value: 535.19.

[0195] Preparation of intermediate P8:

[0196] Intermediate P8 was synthesized using intermediate P1 as a reference, except that intermediate K1 was replaced with intermediate K8 to obtain intermediate P8. LC-MS: Measured value: 605.33 ([M+H)) + Theoretical value: 604.38.

[0197] Preparation of intermediate Q8:

[0198] Intermediate Q8 was synthesized using the same method as intermediate Q1, except that intermediate P1 was replaced with intermediate P8. LC-MS: Measured value: 844.41 (M+H) + Theoretical value: 843.46.

[0199] Preparation of compound 197:

[0200] The synthesis of compound 197 was based on compound 191, except that intermediate Q7 was replaced with intermediate Q8, yielding compound 197. LC-MS: Measured value: 852.49 ([M+H)). + ), Measured value: 851.44. 1 ¹H NMR (400MHz, Chloroform-d) δ 8.20 (m, 2H), 8.00–7.84 (m, 2H), 7.69–7.50 (m, 6H), 7.43–7.19 (m, 5H), 7.16–6.95 (m, 6H), 6.87 (t, 1H), 2.09–1.51 (m, 32H). In toluene solution (1×10⁻⁶) -5 The half-width at half maximum (WHM) is 25 nm.

[0201] For the same type of coupling reaction, since the solvent, catalyst type, and reaction temperature are the same, the reaction time can be adjusted according to conventional techniques, so it has not been repeated.

[0202] Note: FWHM (half-maximum width) was measured using a Horiba Fluorolog-3 series fluorescence spectrometer in thin film condition.

[0203] The structural characterization of the compounds obtained in each embodiment is shown in Table 1.

[0204] Table 1

[0205]

[0206]

[0207] The compounds of this invention can be used as doping materials for the light-emitting layer in light-emitting devices.

[0208] Device Examples

[0209] The following details the application effects of the OLED materials synthesized in this invention in devices through Device Examples 1-8 and Comparative Examples 1-3. Device Examples 2-8 and Comparative Examples 1-3 of this invention have the same fabrication process as Device Example 1, and use the same substrate and electrode materials, with consistent electrode film thickness. The only difference is the replacement of the light-emitting layer material. The layer structures and test results of each device example are shown in Tables 2 and 3, respectively.

[0210] Device Example 1

[0211] like Figure 1 As 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 58 as the dopant material, with a mass ratio of GH-1, GH-2, and compound 58 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, a Mg:Ag electrode layer with a thickness of 80 nm is fabricated using a vacuum evaporation apparatus, with a Mg:Ag mass ratio of 1:9; this layer serves as the cathode layer 10.

[0212] The application effects of the OLED material synthesized in this invention in devices are described in detail below through device examples 9-16 and device comparative examples 4-6. Device examples 10-16 and device comparative examples 4-6 of this invention have the same fabrication process as device example 9, 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 2 and 3, respectively.

[0213] Device Example 9

[0214] 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 58 is used as the second dopant. The mass ratio of GH-1, GH-2, GD-1, and compound 58 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, with a thickness of 30 nm; this layer is the electron transport layer 8. On the electron transport layer 8, a LiF layer with a thickness of 1 nm is fabricated using a vacuum evaporation apparatus; this layer is the electron injection layer 9. On the electron injection layer 9, a Mg:Ag electrode layer with a thickness of 80 nm is fabricated using a vacuum evaporation apparatus; the mass ratio of Mg to Ag is 1:9; this layer is used as the cathode layer 10.

[0215] The molecular structural formulas of the relevant materials are shown below:

[0216]

[0217] 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 2; the test results for the current efficiency and lifetime of the obtained devices are shown in Table 3.

[0218] Table 2

[0219]

[0220]

[0221] Table 3

[0222]

[0223]

[0224] Note: Voltage, 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.

[0225] As can be seen from the device data results in Table 3, 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 that in single-doped systems.

[0226] 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 in that, The structure of the resonance-type organic compound is shown in any one of general formulas (1-2) to (1-4) and (1-8): In general formulas (1-2) to (1-4) and (1-8), Z is represented as C-R1; each occurrence of R1, whether the same or different, is represented by H, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C. 10 Alkyl or silyl groups, substituted amino groups, substituted or unsubstituted C6-C groups 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl groups; Ar1 represents substituted or unsubstituted C6-C. 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl groups; Z1, Z2, and Z3 represent CR respectively. a CR b CR c ;R a R b R c Each occurrence of the same or different C1-C is represented by H, substituted or unsubstituted C1-C. 10 Alkyl or silyl groups, substituted amino groups, substituted or unsubstituted C6-C groups 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl groups; and R a R b R c Not simultaneously represented by H; Ar2 represents substituted or unsubstituted C6-C. 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl groups; R7 and R8 represent hydrogen atoms, substituted or unsubstituted C1-C atoms. 10 Alkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 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 selected from one of O, S, N, and Si.

2. A resonance-type organic compound, characterized in that, The structure of the resonance-type organic compound is shown in any one of general formulas (5) to (6): In general formulas (2) to (6), Z is represented as C-R1; Each occurrence of R1, whether the same or different, is represented by H, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C. 10 Alkyl or silyl groups, substituted amino groups, substituted or unsubstituted C6-C groups 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl groups; X is represented as N(R6); R6 indicates substituted or unsubstituted C6-C. 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl groups; M1 represents a substituted or unsubstituted phenyl group. One of them; M2 is represented as: 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 selected from one of O, S, N, and Si.

3. A resonance-type organic compound, characterized in that, The structures of the resonance-type organic compounds are shown in general formulas (8) to (10): In general formulas (8) to (10), Z is represented as C-R1; each occurrence of R1, whether the same or different, is represented by H, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C. 10 Alkyl or silyl groups, substituted amino groups, substituted or unsubstituted C6-C groups 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl groups; Z1, Z2, and Z3 represent CR respectively. a CR b CR c ;R a R b R c Each occurrence of the same or different C1-C is represented by H, substituted or unsubstituted C1-C. 10 Alkyl or silyl groups, substituted amino groups, substituted or unsubstituted C6-C groups 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl groups; and R a R b R c Not simultaneously represented by H; 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 selected from one of O, S, N, and Si.

4. The resonance-type organic compound according to claim 1, characterized in that, The R1, R a R b R c It can be represented as the structure shown below: hydrogen atom, Any one of them; R7 and R8 are represented as shown in the following structure: Any one of them; The Ar1 is represented by the following structure: Any one of them.

5. The resonance-type organic compound according to claim 2, characterized in that, M1 can be represented by any of the following ring structures: M2 can be represented by any of the following ring structures: R1 is represented by the following structure: hydrogen atom, Any one of them; The R6 is represented by the following structure: Any one of them.

6. The resonance-type organic compound according to claim 3, characterized in that, The R1, R a R b R c It can be represented as the structure shown below: hydrogen atom, Any one of them.

7. The resonance-type organic compound according to claim 1, characterized in that, Each instance of R1, whether identical or different, is represented by hydrogen, 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 pyridine group. The following compounds are listed: pyridyl, 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 triazineyl. The recurrence of R7 and R8, whether identical or different, represents 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 vinyl, substituted or unsubstituted propenyl, 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... Substituted pyridyl, 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 triazineyl; The R a R b R c Each instance of the same or different is represented by H, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted vinyl, substituted or unsubstituted propenyl, 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, 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 triazineyl; Ar2 represents a phenyl or tert-butyl-substituted phenyl; 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.

8. The resonance-type organic compound according to claim 2, characterized in that, Each instance of R1, whether identical or different, is represented by hydrogen, 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 pyridine group. The following compounds are listed: pyridyl, 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 triazineyl. The R6 represents substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted triphenyl, 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 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted triazineyl; 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.

9. The resonance-type organic compound according to claim 3, characterized in that, Each instance of R1, whether identical or different, is represented by hydrogen, 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 thiophene, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amino, substituted or unsubstituted triazineyl; The R a R b R c Each instance of the same or different is represented by H, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted vinyl, substituted or unsubstituted propenyl, 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, substituted or unsubstituted furanyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amino, substituted or unsubstituted triazineyl; The substituents used for the substituent groups are selected from one or more of the following: deuterium 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.

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

11. 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, characterized in that, The functional layer includes a light-emitting layer, which is a resonant organic compound as described in any one of claims 1-10.

12. The organic light-emitting device according to claim 11, characterized in that, The light-emitting layer comprises a first host material, a second host material, and a dopant material, wherein at least one of the first host material and the second host material is a TADF material, and the dopant material is a resonant organic compound as described in any one of claims 1-10.

13. The organic light-emitting device according to claim 11, wherein the light-emitting layer comprises a host material, an exciton-sensitizing material, and a dopant material, characterized in that, The exciton sensitizing material is a complex containing a metal element, and the doping material is a resonance-type organic compound as described in any one of claims 1-10.

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