A resonance type organic compound and its application

Abstract

The present invention relates to a resonance type organic compound and its application, belonging to the field of semiconductor technology. The present invention provides a compound having a structure as shown in the general formula (1): the compound of the present invention has a narrow half-peak width and a high fluorescence quantum yield. When used as a doping material in a light-emitting layer material of an OLED light-emitting device, the current efficiency of the device is significantly improved, and the luminous color purity and device life are also greatly improved.

Description

Technical Field

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

[0002] Traditional fluorescent doped materials are limited by early technologies and can only use 25% of singlet excitons formed by electrical excitation to emit light. The internal quantum efficiency of the device is low (up to 25%), and the external quantum efficiency is generally less than 5%, which is far behind the efficiency of phosphorescent devices. Phosphorescent materials can effectively use singlet and triplet excitons formed by electrical excitation to emit light, due to the strong spin-orbit coupling of the heavy atom center, which enhances intersystem crossing, so that the internal quantum efficiency of the device can reach 100%.

[0003] With the advent of the 5G era, higher requirements are placed on color rendering standards. In addition to being efficient and stable, luminescent materials also require a narrower half-width to improve the purity of the device's luminescent color. Fluorescent doped materials can achieve high fluorescence quantum and narrow half-width through molecular engineering. Blue fluorescent doped materials have achieved a phased breakthrough, and the half-width of boron materials can be reduced to below 30nm. In the green light region, which is more sensitive to the human eye, research is mainly focused on phosphorescent doped materials, but their luminescent peak shape is difficult to narrow by simple methods. Therefore, in order to meet higher color rendering standards, it is of great significance to study efficient green fluorescent doped materials with narrow half-width.

[0004] In addition, the sensitization technology combines triplet exciton-sensitizing materials with fluorescent doping materials, uses triplet exciton-sensitizing materials as exciton-sensitizing media, makes full use of triplet excitons, and transfers energy to fluorescent doping materials through energy transfer, which can also achieve 100% device quantum efficiency. This technology can make up for the shortcomings of insufficient exciton utilization of fluorescent doping materials, and effectively give play to the characteristics of high fluorescence quantum yield, high device stability, high color purity and low price of fluorescent doping materials, and has broad prospects in OLEDs applications.

[0005] Boron compounds with a resonant structure are more likely to achieve narrow half-width luminescence. Such materials are used in sensitized fluorescence technology to achieve the preparation of devices with high efficiency and narrow half-width emission. For example, CN 107507921 A and CN 110492006 A disclose a luminescent layer combination technology with a TADF material having a difference between the lowest singlet and the lowest triplet energy level of less than or equal to 0.2eV as the main body and a boron-containing material as the doping; CN 110492005 A and CN 110492009 A disclose a luminescent layer combination scheme with an exciplex as the main body and a boron-containing material as the doping; both can achieve efficiency comparable to phosphorescence and a relatively narrow half-width. Therefore, the development of sensitization technology based on narrow half-width boron-based luminescent materials has unique advantages and strong potential in terms of BT.2020 display indicators. Summary of the invention

[0006] In view of the above problems existing in the prior art, the applicant of the present invention provides a resonance type organic compound and its application. In the general formula (1), the resonance type organic compound is formed by introducing the structure of carbazole indole fused ring, which has the effect of significantly adjusting light color, improving quantum yield and improving device life.

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

[0008]

[0009] In the general formula (1), Z is C-R1; R1, which is the same or different each time, is H, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C1-C 10 alkenyl or silane, substituted or unsubstituted arylamine, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl, substituted or unsubstituted C1-C 10 One of the alkoxy groups; adjacent R1 groups may be connected to form a ring;

[0010] M1 and M2 represent substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl;

[0011] Ar1 and Ar2 are independently 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 heteroaryl;

[0012] Ar2 and M1 can be connected to form a ring;

[0013] The substituents for the substituent groups are selected from halogen atoms, deuterium atoms, cyano groups, C1-C 10 Alkyl, C5-C 10 Cycloalkyl, C5-C 10 Cycloalkenyl, C1-C 10 Alkoxy, C3-C 20 Cycloalkyl, C6-C 30 Aryl, C3-C 30 one or more of heteroaryl groups;

[0014] The heteroatom in the heteroaryl group is selected from one of O, S, N and Si.

[0015] In a preferred embodiment, the structure of the resonance type organic compound is shown in any one of the general formulas (1-1) to (1-2):

[0016]

[0017] In general formula (1-1) to general formula (1-2), the definitions of Z, M1, M2, Ar1 and Ar2 are the same as those defined above;

[0018] Z1, Z2, Z3, Z4, Z5, Z6, and Z7 are independently represented by CH or C-R2; R2, which is the same or different each time, is represented by H, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C1-C 10 alkenyl or silane, substituted or unsubstituted arylamine, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl, substituted or unsubstituted C1-C 10 One of the alkoxy groups; adjacent R2 groups may be connected to form a ring;

[0019] The substituents for the substituent groups are selected from halogen atoms, deuterium atoms, cyano groups, C1-C 10 Alkyl, C5-C 10 Cycloalkyl, C5-C 10 Cycloalkenyl, C1-C 10 Alkoxy, C3-C 20 Cycloalkyl, C6-C 30 Aryl, C3-C 30 one or more of heteroaryl groups;

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

[0021] In a preferred embodiment, the structure of the resonance type organic compound is shown in any one of the general formulas (1-3) to (1-9):

[0022]

[0023]

[0024] In general formula (1-3) to general formula (1-9), the definitions of Z, Ar1 and Ar2 are the same as those defined above;

[0025] Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8, Z9, Z10 , Z 11 Each independently represents CH or C-R2; R2, which is the same or different each time, represents H, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C1-C 10 alkenyl or silane, substituted or unsubstituted arylamine, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl, substituted or unsubstituted C1-C 10 One of the alkoxy groups; adjacent R2 groups may be connected to form a ring;

[0026] Ar3 represents a 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 heteroaryl;

[0027] The substituents for the substituent groups are selected from halogen atoms, deuterium atoms, cyano groups, C1-C 10 Alkyl, C5-C 10 Cycloalkyl, C5-C 10 Cycloalkenyl, C1-C 10 Alkoxy, C3-C 20 Cycloalkyl, C6-C 30 Aryl, C3-C 30 one or more of heteroaryl groups;

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

[0029] In a preferred embodiment, the structure of the resonance type organic compound is shown in any one of the general formulas (2-1) to (2-8):

[0030]

[0031] In general formula (2-1) to general formula (2-8), the definitions of Z, M1, Ar1 and Ar2 are the same as those defined above.

[0032] Preferably, the M1 is represented by any one of the following ring structures:

[0033]

[0034] The M2 is represented by any of the following ring structures:

[0035]

[0036] The definition of Z in the above formula is the same as defined above.

[0037] In a preferred embodiment, the structure of the organic compound is as shown in general formula (3-1) to general formula (3-9):

[0038]

[0039]

[0040] In general formula (3-1) to general formula (3-9), the definition of Z is the same as defined above.

[0041] In a preferred embodiment, the R1 and R2 are the same or different each time and are represented by hydrogen, a deuterium atom, a tritium 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 phenanthrenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted substituted 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, substituted or unsubstituted amine, substituted or unsubstituted triazine, substituted or unsubstituted 4a,9a-dimethyl-9-phenyl-1,2,3,4-tetrahydrocarbazole;

[0042] The Ar1, Ar2, and Ar3 are independently 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 anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyridine. substituted or unsubstituted quinolyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amine;

[0043] The M1 and M2 are represented by substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolyl, substituted or unsubstituted furyl, 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 indole [3,2,1-jk] carbazolyl, substituted or unsubstituted 4a,9a-dimethyl-9-phenyl-1,2,3,4-tetrahydrocarbazole;

[0044] The substituent for the substituent group is optionally selected from one or more of a deuterium atom, a chlorine atom, a fluorine atom, a trifluoromethyl group, an adamantyl group, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-amyl group, a tert-butyl group, a butyl group, a methoxy group, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl 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, and an azaphenanthryl group.

[0045] In a preferred embodiment, Ar1, Ar2 and Ar3 are represented by the following structure:

[0046]

[0047] In a preferred embodiment, R1 and R2 are represented by the following structure:

[0048]

[0049] In a preferred embodiment, the specific structural formula of the resonance-type organic compound is any one of the following structures:

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060] An organic light-emitting device comprises 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 comprises the resonance type organic compound.

[0061] Preferably, the functional layer comprises a light-emitting layer, the light-emitting layer comprises a main material and a doping material, and the doping material is the resonance-type organic compound.

[0062] In a preferred embodiment, the light-emitting layer comprises a first main material, a second main material and a doping material, at least one of the first main material and the second main material is a TADF material, and the doping material is the resonance-type organic compound.

[0063] In a preferred embodiment, the light-emitting layer comprises a main material, an exciton-sensitizing material and a doping material, wherein the exciton-sensitizing material is a complex containing a metal element, and the doping material is the resonance-type organic compound.

[0064] Compared with the prior art, the beneficial technical effects of the present invention are:

[0065] (1) The compounds of the present invention are applied to OLED devices and can be used as doping materials for light-emitting layer materials. They can emit fluorescence under the action of an electric field and can be applied to OLED lighting or OLED display fields;

[0066] (2) The spectral FWHM of the compound of the present invention is relatively narrow, which can effectively improve the color gamut of the device and the luminous efficiency of the device;

[0067] (3) The introduction of a spatial structural unit into the compound of the present invention is conducive to further enhancing the resonance effect of the molecule, thereby further narrowing the emission spectrum of the material;

[0068] (4) The compounds of the present invention introduce spatial stereostructure units, which can further increase the molecular volume and reduce the accumulation of molecules, thereby achieving the effect of increasing lifespan.

[0069] The compound of the invention has a narrow half-peak width and a large spatial volume, and can be used as a doping material for the light-emitting layer of an organic electroluminescent device, thereby improving the light-emitting color purity and life of the device. BRIEF DESCRIPTION OF THE DRAWINGS

[0070] Figure 1 This is a schematic diagram of the structure of an OLED device in which the materials listed in the present invention are applied;

[0071] Among them, 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 DESCRIPTION

[0072] The present invention is described in detail below in conjunction with the accompanying drawings and embodiments.

[0073] In the present invention, when describing electrodes and organic electroluminescent devices, as well as other structures, the words "upper", "lower", "top" and "bottom" used to indicate orientation only indicate the orientation in a certain state, and do not mean that the related structure can only exist in the orientation described; on the contrary, if the structure can change its position, such as inverted, the orientation of the structure will be changed accordingly. Specifically, in the present invention, the "bottom" or "lower" side of the electrode refers to the side of the electrode close to the substrate during the preparation process, and the opposite side away from the substrate is the "top" or "upper" side.

[0074] In the present invention, the substituted or unsubstituted C6-C 30Aryl refers to substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted tetraphenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted The invention may include, but is not limited to, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylenyl group, and a substituted or unsubstituted indenyl group.

[0075] In the present invention, substituted or unsubstituted C2-C 30 The heteroaryl group refers to a substituted or unsubstituted furanyl, a substituted or unsubstituted thienyl, a substituted or unsubstituted pyrrolyl, a substituted or unsubstituted pyrazolyl, a substituted or unsubstituted imidazolyl, a substituted or unsubstituted triazolyl, a substituted or unsubstituted oxazolyl, a substituted or unsubstituted thiazolyl, a substituted or unsubstituted oxadiazolyl, a substituted or unsubstituted thiadiazolyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted benzofuranyl, a substituted or unsubstituted benzothienyl, a substituted or unsubstituted benzimidazolyl, a substituted or unsubstituted The invention also includes substituted indolyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridinyl, substituted or unsubstituted phenathiazinyl, substituted or unsubstituted phenathiazinyl, substituted or unsubstituted phenathiazinyl, substituted or unsubstituted phenathiazinyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, combinations thereof, or fused rings of combinations of the foregoing groups, but is not limited thereto.

[0076] The C1-C 10 Alkyl (including straight-chain alkyl and branched alkyl) refers 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 and the like, but is not limited thereto.

[0077] The C3-C 10Cycloalkyl refers to a monovalent monocyclic saturated hydrocarbon group including 3 to 10 carbon atoms as ring atoms. In this article, C4-C9 cycloalkyl is preferably used, C5-C8 cycloalkyl is more preferably used, and C5-C7 cycloalkyl is particularly preferably used. Non-limiting examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl and cycloheptyl, but are not limited thereto.

[0078] As the substrate of the organic electroluminescent device of the present invention, any substrate commonly used in organic electroluminescent devices can be used. Examples are transparent substrates such as glass or transparent plastic substrates; 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 use direction is different. In the present invention, a transparent PI film substrate is preferably used. The thickness of the substrate is not particularly limited.

[0079] A first electrode is formed on a substrate, and the first electrode and the second electrode may be opposite to 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 metal mixture. The thickness of the first electrode layer depends on the material used, and is typically 50-500nm, preferably 70-300nm and more preferably 100-200nm.

[0080] 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.

[0081] Herein, the hole transport region constituting the organic electroluminescent device can be exemplified by a hole injection layer, a hole transport layer, an electron blocking layer, and the like.

[0082] As the material for the hole injection layer, the hole transport layer, and the electron blocking layer, any material can be selected from known related materials used for OLED devices.

[0083] Examples of the above materials include phthalocyanine derivatives, triazole derivatives, triarylmethane derivatives, triarylamine derivatives, oxazole derivatives, oxadiazole derivatives, hydrazone derivatives, stilbene derivatives, pyridoline derivatives, polysilane derivatives, imidazole derivatives, phenylenediamine derivatives, amino-substituted quilone derivatives, styryl anthracene derivatives, styrylamine derivatives and the like, fluorene derivatives, spirofluorene derivatives, silazane derivatives, aniline copolymers, porphyrin compounds, carbazole derivatives, polyarylalkane derivatives, polyphenylene vinyl and its derivatives, polythiophene and its derivatives, poly-N-vinylcarbazole derivatives, thiophene oligomers and the like, conductive polymer oligomers, aromatic tertiary amine compounds, styrene amination compounds, compounds, triamines, tetraamines, benzidines, propargyl diamine derivatives, p-phenylenediamine derivatives, m-phenylenediamine derivatives, 1,1'-bis(4-diarylaminophenyl)cyclohexane, 4,4'-bis(diarylamino)biphenyls, bis[4-(diarylamino)phenyl]methanes, 4,4'-bis(diarylamino)terphenyls, 4,4'-bis(diarylamino)quaterphenyls, 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.

[0084] Furthermore, according to the device matching requirements, the hole transport film layer between the electron blocking layer and the hole injection layer of the organic electroluminescent device can be a single film layer or a superposition structure of multiple hole transport materials. In this article, for the above-mentioned hole carrier conduction film layers with different functions, their film thickness is not particularly limited.

[0085] The hole injection layer contains a main organic material that can conduct holes, and also contains a P-type dopant material with a deep HOMO energy level (the corresponding LUMO energy level will also be very deep). Based on empirical summary, in order to achieve smooth injection of holes from the anode to the organic film layer, the HOMO energy level of the main organic material that conducts holes used in the anode interface buffer layer must have certain characteristics with the P-doped material, so that the charge transfer state between the main material and the dopant material can be realized, the ohmic contact between the buffer layer and the anode can be achieved, and the efficient injection from the electrode to the hole injection conduction can be achieved.

[0086] In view of the above empirical summary, for hole-type host materials with different HOMO energy levels, different P-doped materials need to be selected to match them in order to achieve ohmic contact at the interface and improve the hole injection effect.

[0087] Therefore, in one embodiment of the present invention, in order to better inject holes, the hole injection layer also includes a P-type doping material with charge conductivity selected from the following: quinone derivatives, such as tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ); or hexaazatriphenylene derivatives, such as 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (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 to these.

[0088] In the hole injection layer of the present invention, the ratio of the hole transport material to the P-type doping material used is 99:1-95:5, preferably 99:1-97:3, based on mass.

[0089] The thickness of the hole injection layer of the present invention may be 5-100 nm, preferably 5-50 nm, and more preferably 5-20 nm, but the thickness is not limited to this range.

[0090] The thickness of the hole transport layer of the present invention may be 5-200 nm, preferably 10-150 nm, and more preferably 20-100 nm, but the thickness is not limited to this range.

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

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

[0093] The light-emitting layer may include a host material and a dopant material. The host material may be a common green light host material in the art, and the dopant material may be a resonance-type organic compound represented by the general formula (1) of the present invention.

[0094] The light-emitting layer may contain a single host material or a dual host material;

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

[0096] TADF materials refer to materials with thermally activated delayed fluorescence properties, characterized by a small energy level difference between the first excited singlet state and the first excited triplet state, so that the singlet excitons and triplet excitons generated can be used simultaneously in the device, making the utilization rate of the excitons generated by the device as close to 100% as possible. Compared with traditional fluorescent materials, TADF materials have a higher exciton utilization rate.

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

[0098] Exciton sensitizing materials refer to materials that can make the luminescent material in the luminescent layer fully utilize the electroinduced excitons, so that the luminescent layer finally produces the emission spectrum of the sensitized material. Exciton sensitizers may undertake functions such as exciton capture, exciton conversion, and exciton transfer in electroluminescent devices. The resonant organic compound represented by the general formula (1) of the present invention and the exciton sensitizing material are used in combination, which has a significant improvement effect on the problems of device efficiency improvement, exciton annihilation in the device, and efficiency reduction.

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

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

[0101] In the present 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.

[0102] The hole blocking layer is a layer that blocks the holes injected from the anode from passing through the light-emitting layer and entering the cathode, thereby extending the life of the device and improving the efficiency of the device. The hole blocking layer of the present invention can be arranged on the light-emitting layer. As the hole blocking layer material of the organic electroluminescent device of the present invention, compounds with hole blocking effects known in the prior art can be used, for example, phenanthroline derivatives such as bathocuproin (referred to as BCP), metal complexes of hydroxyquinoline derivatives such as aluminum (III) bis (2-methyl-8-quinoline) -4-phenylphenolate (BAlq), various rare earth complexes, oxazole derivatives, triazole derivatives, triazine derivatives, 9,9'-(5-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-1,3-phenylene) bis (9H-carbazole) and the like pyrimidine derivatives. The thickness of the hole blocking layer of the present invention can be 2-200nm, preferably 5-150nm, but the thickness is not limited to this range.

[0103] The electron transport layer may be disposed on the light emitting layer or (if present) the hole blocking layer. The electron transport layer material is a material that easily receives electrons from the cathode and transfers the received electrons to the light emitting layer. Preferably, the material has a high electron mobility. As the electron transport layer of the organic electroluminescent device of the present invention, the electron transport layer materials for organic electroluminescent devices known in the prior art can be used, for example, metal complexes of hydroxyquinoline derivatives represented by Alq3, BAlq and Liq, various rare earth metal complexes, triazole derivatives, 2,4-bis(9,9-dimethyl-9H-fluorene-2-yl)-6-(naphthalene-2-yl)-1,3,5-triazine (CAS No.: 1459162-51-6) and other triazine derivatives, 2-(4-(9,10-di(naphthalene-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole (CAS No.: 561064-11-7, commonly known as LG201) and other imidazole derivatives, 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 may be 10-80 nm, preferably 20-60 nm, and more preferably 25-45 nm, but the thickness is not limited to this range.

[0104] The electron injection layer may be disposed above the electron transport layer. The electron injection layer material is generally preferably a material having a low work function so that electrons are easily injected into the organic functional material layer. As the electron injection layer material of the organic electroluminescent device of the present invention, the electron injection layer material for organic electroluminescent devices known in the prior art can be used, for example, lithium; lithium salts such as 8-hydroxyquinoline lithium, lithium fluoride, lithium carbonate or lithium azide; or cesium salts, 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.

[0105] The second electrode may be disposed above the electron transport region. The second electrode may be a cathode. The second electrode may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the second electrode is a transmissive electrode, the second electrode may include, for example, Li, Yb, Ca, LiF / Ca, LiF / Al, Al, Mg, BaF, Ba, Ag, or a compound or mixture thereof; when the second electrode is a semi-transmissive electrode or a reflective electrode, the second electrode may include Ag, Mg, Yb, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, or a compound or mixture thereof, but is not limited thereto. The thickness of the cathode depends on the material used.

[0106] The organic electroluminescent device of the present invention may further include an encapsulation structure. The encapsulation structure may be a protective structure that prevents foreign 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 can or a metal can; or a thin film covering the entire surface of the organic layer.

[0107] The method for preparing the organic electroluminescent device of the present invention comprises 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 successively on a substrate, and optionally a covering layer. In this regard, vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing or LITI methods can be used, but are not limited thereto. In the present invention, it is preferred to use a vacuum evaporation method to form the various layers. Those skilled in the art can conventionally select various process conditions in the vacuum evaporation method according to actual needs.

[0108] Synthesis Example

[0109] The raw materials involved in the synthesis examples of the present invention can be purchased from the market or prepared by conventional preparation methods in the art.

[0110] I. Synthesis of Intermediate J

[0111] 1. Synthesis of intermediate J1:

[0112]

[0113] In a three-necked flask, under nitrogen protection, the raw material M1 (0.5mmol) was dissolved in 5mL of dichloromethane, 0.55mmol of tert-butyl hypochlorite was added, TMEDA (0.5mmol) was added after 30 seconds and stirred at room temperature for 2 minutes. Then the raw material N1 (0.75mmol) and 1N sulfuric acid solution (0.5mL) were added to the mixture and continued to stir at room temperature for 5 minutes. The resulting solution was diluted with dichloromethane (20mL) and then washed with H2O (30mL). The organic layer was dried and filtered using Na2SO4, and then concentrated and dried under vacuum. The residue was purified by silica gel column chromatography (PE / EtOAc=10:1) to obtain intermediate J1. LC-MS: Measured value: 339.23 ([M+H] + ), theoretical value: 338.18.

[0114] 2. Synthesis of intermediates J2 and J3:

[0115]

[0116] Under nitrogen protection, 10 mmol of raw material M2, 25 mmol of raw material M3, 1 mmol of CuI, 15 mmol of cesium carbonate, 2 mmol of o-phenanthroline and 10 mL of anhydrous DMF were added to a three-necked flask and reacted at room temperature for 4 hours. After the reaction was completed, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain intermediate a-1. LC-MS: Measured value: 339.24 ([M+H] + ), theoretical value: 338.20.

[0117] Add 1 mmol of intermediate a-1, 1 mmol of raw material M4, and 10 mml of methanol to a sealed pressure tube, add 300 mg of concentrated sulfuric acid dropwise, reflux and stir for 8 hours, cool the reaction solution to room temperature, dilute with 20 ml of dichloromethane, and separate by column chromatography to obtain intermediate b-1 and intermediate b-2. Intermediate b-1: LC-MS: Measured value: 293.23 ([M+H] + ), theoretical value: 292.19. 1 HNMR (400 MHz, Chloroform-d): δ1.41-1.79 (12H, m), 1.91-2.25 (6H, m), 2.29-2.58 (4H, m), 7.29 (2H, d); Intermediate b-2: LC-MS: Measured value: 293.34 ([M+H] + ), theoretical value: 292.19. 1 H NMR (400MHz, Chloroform-d): δ1.44-1.68(10H,m), 1.73-2.25(8H,m), 2.31-2.50(4H,m), 6.76(2H,d).

[0118] In a sealed pressure tube, under nitrogen protection, 10 mmol of intermediate b-1 was added to anhydrous o-dichlorobenzene, and 22 mmol of methyl lithium (n-hexane) solution was added dropwise at -40 degrees Celsius. After stirring for 3 hours, the room temperature was restored. The reaction solution was concentrated and separated by column chromatography to obtain intermediate c-1. LC-MS: Measured value: 325.33 ([M+H] + ), theoretical value: 324.26.

[0119] Under nitrogen protection, 10 mmol of intermediate c-1, 11 mmol of raw material M4, 15 mmol of sodium tert-butoxide, 0.5 mmol of palladium acetate, 1.5 mmol of tri-tert-butylphosphine and 40 mL of anhydrous toluene were added to a three-necked flask and refluxed for 20 hours. After the reaction was completed, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate J2. LC-MS: Measured value: 457.41 ([M+H] + ), theoretical value: 456.35.

[0120] In a sealed pressure tube, under nitrogen protection, 10 mmol of intermediate b-2 was added to anhydrous o-dichlorobenzene, and 22 mmol of methyl lithium (n-hexane) solution was added dropwise at -40 degrees Celsius. After stirring for 3 hours, the room temperature was restored. The reaction solution was concentrated and separated by column chromatography to obtain intermediate c-2. LC-MS: Measured value: 325.29 ([M+H] + ), theoretical value: 324.26.

[0121] Under nitrogen protection, 10 mmol of intermediate c-2, 11 mmol of raw material M5, 15 mmol of sodium tert-butoxide, 0.5 mmol of palladium acetate, 1.5 mmol of tri-tert-butylphosphine and 40 mL of anhydrous toluene were added to a three-necked flask and refluxed for 15 hours. After the reaction was completed, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate J3. LC-MS: Measured value: 457.44 ([M+H] + ), theoretical value: 456.35.

[0122] 3. Synthesis of Intermediate J4

[0123]

[0124] Under nitrogen protection, 10 mmol of raw material M5, 11 mmol of raw material M6, 15 mmol of sodium tert-butoxide, 0.5 mmol of palladium acetate, 1.5 mmol of tri-tert-butylphosphine and 40 mL of anhydrous toluene were added to a three-necked flask and refluxed for 15 hours. After the reaction was completed, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate J4. LC-MS: Measured value: 459.22 ([M+H] + ), theoretical value: 458.27.

[0125] II. Synthesis of Example Compounds

[0126] Example 1 Synthesis of Compound 20:

[0127]

[0128] Preparation of intermediate K1:

[0129] Raw material A1 (20.0 mmol), raw material B1 (22.0 mmol), CuI catalyst (2 mmol), K3PO4 (45 mmol) were added to a three-necked flask in sequence, and then 3 mmol of trans-1,2-cyclohexanediamine and 160 mL of dioxane were added under a nitrogen atmosphere. After stirring at 110°C for 15 hours, the reaction mixture was 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 K1. LC-MS: Measured value: 470.28 ([M+H] + ), theoretical value: 469.12.

[0130] Preparation of intermediate P1:

[0131] To a three-necked flask, add intermediate K1 (20.0 mmol), intermediate J1 (22.0 mmol), CuI catalyst (2 mmol), K3PO4 (45 mmol), and then continue to add 3 mmol trans-1,2-cyclohexanediamine and 160 mL dioxane under a nitrogen atmosphere. After stirring at 110°C for 16 hours, the reaction mixture is cooled to room temperature, diluted with toluene, filtered through silica gel, and concentrated. The compound is separated by silica gel column chromatography (toluene: hexane = 1:2) to obtain intermediate P1. LC-MS: Measured value: 728.40 ([M+H] + ), theoretical value: 727.37.

[0132] Preparation of intermediate W1:

[0133] Add intermediate P1 (5.0mmol) and tert-butylbenzene (50mL) in turn to a low-temperature eggplant-shaped bottle, cool to -78°C, slowly add n-butyl lithium (5.5mmol) in n-hexane solution, then stir and warm to room temperature, then remove n-hexane at 60°C under negative pressure; then connect nitrogen protection, react for 2 hours, add BBr3 (6.0mmol) at -42°C, keep stirring for 2 hours, slowly return to room temperature, stir at room temperature for 12 hours, add DIPEA (N,N-diisopropylethylamine) (10mmol) in an ice-water bath, heat to 120°C and reflux for 36 hours, cool the reaction to room temperature, filter the solution with diatomaceous earth, collect the organic phase and remove the high boiling point solvent by vacuum distillation, dissolve with dichloromethane, dry with anhydrous sodium sulfate, filter, concentrate the organic phase and purify with a silica gel column, use toluene as a developing solvent to obtain intermediate W1. LC-MS: Measured value: 702.48 ([M+H] + ), theoretical value: 701.39.

[0134] Preparation of intermediate T1:

[0135] Add intermediate W1 (10.0 mmol), biboronic acid pinacol ester (15 mmol), [Ir(COD)(OCH3)]2 (0.06 mmol), and 150 mL of tetrahydrofuran to a single-mouth bottle in sequence, react at room temperature for 12 hours, and protect with nitrogen, then filter the reaction, concentrate the organic phase, and separate the compound through a silica gel column with petroleum ether: ethyl acetate = 1:1 as the developing solvent to obtain intermediate T1. The reaction has relatively good selectivity (reference DOI: 10.31635 / ccschem.021.202101033), and boron esters at the para position of boron have higher activity and selectivity. LC-MS: Measured value: 828.53 ([M+H] + ), theoretical value: 827.48.

[0136] Preparation of compound 20:

[0137] Into a two-necked flask were added intermediate T1 (10.0 mmol), raw material E1 (11.0 mmol), Pd(PPh3)4 catalyst (0.1 mmol), 150 mL of a mixed solution of tetrahydrofuran: water = 10:1, and potassium carbonate (20 mmol), followed by nitrogen protection and stirring at 80 °C for 5.5 hours. After cooling, the liquids were separated and the organic phase was collected, dried over anhydrous sodium sulfate, filtered and concentrated, and the compound was separated by passing through a silica gel column with petroleum ether: ethyl acetate = 5:1 as the developing solvent to obtain compound 20. 1 H NMR (400MHz, Chloroform-d) δ8.76–8.43 (m, 4H), 7.58–7.48 (m, 6H), 7.44–7.37 (m, 2H), 7.36–7.28 (m, 6H), 7.24 (dd, 1H), 7.13–6.94 (m, 10H), 6.74 (s, 2H), 2.56–2.26 (m, 2H), 1.73–1.47 (m, 6H), 1.30 (d, 18H). Toluene solution (1×10 -5 The half-peak width is 26 nm.

[0138] Example 2 Synthesis of Compound 30:

[0139]

[0140] Preparation of intermediate K2:

[0141] The synthesis of intermediate K2 refers to intermediate K1, except that raw material A2 is used to replace raw material A1 to obtain intermediate K2. LC-MS: Measured value: 616.06 ([M+H] + ), theoretical value: 615.25.

[0142] Preparation of intermediate P2:

[0143] The synthesis of intermediate P2 refers to intermediate P1, except that intermediate K2 is used to replace intermediate K1 to obtain intermediate P2. LC-MS: Measured value: 874.57 ([M+H] + ), theoretical value: 873.50.

[0144] Preparation of compound 30:

[0145] In a three-necked flask, under nitrogen protection, 2mmol of boron tribromide and 1mmol of intermediate P2 were dissolved in 30mL of 1,2,4-trichlorobenzene. After stirring at 180°C for 20 hours, the reaction mixture was diluted with dichloromethane (50mL), and 100mL of sodium phosphate buffer solution with pH=6 was added at 0°C. The aqueous layer was separated and extracted with dichloromethane (100mL, three times). 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 obtain the target compound 30. 1 H NMR (400MHz, Chloroform-d) δ8.20 (m, 1H), 7.90 (m, 1H), 7.65–7.51 (m, 4H), 7.45–7.20 (m, 9H), 7.16–6.92 (m, 10H), 2.49–2.31 (m, 2H), 1.75–1.46 (m, 6H), 1.41–1.19 (m, 27H). Toluene solution (1×10 -5 The half-peak width is 24 nm.

[0146] Example 3 Synthesis of Compound 43:

[0147]

[0148] Preparation of intermediate K3:

[0149] The synthesis of intermediate K3 refers to intermediate K1, except that raw material A3 is used to replace raw material A1, and intermediate J3 is used to replace raw material B1 to obtain intermediate K3. LC-MS: Measured value: 721.41 ([M+H] + ), theoretical value: 720.28.

[0150] Preparation of intermediate P3:

[0151] The synthesis of intermediate P3 refers to intermediate P1, except that intermediate K3 is used to replace intermediate K1 to obtain intermediate P3. LC-MS: Measured value: 979.47 ([M+H] + ), theoretical value: 978.54.

[0152] Preparation of compound 43:

[0153] The synthesis of compound 43 refers to compound 20, except that intermediate P3 is used to replace intermediate P1 to obtain compound 43. 1 H NMR (400MHz, Chloroform-d) δ7.63–7.56 (m, 2H), 7.48–7.27 (m, 10H), 7.24 (dd, 1H), 7.14–6.94 (m, 8H), 6.74 (s, 2H), 6.70 (s, 1H), 2.49–2.33 (m, 2H), 2.07–1.94 (m, 2H), 1.84–1.38 (m, 20H), 1.36–1.17 (m, 21H). Toluene solution (1×10 -5 The half-peak width is 29 nm.

[0154] Example 4 Synthesis of Compound 86:

[0155]

[0156] Preparation of intermediate K4:

[0157] The synthesis of intermediate K4 was based on intermediate K1, except that raw material A4 was used to replace raw material A1, and intermediate J4 was used to replace raw material B1 to obtain intermediate K4. LC-MS: Measured value: 703.08 ([M+H] + ), theoretical value: 702.24.

[0158] Preparation of intermediate P4:

[0159] The synthesis of intermediate P4 was based on intermediate P1, except that intermediate K4 was used to replace intermediate K1 to obtain intermediate P4. LC-MS: Measured value: 961.27 ([M+H] + ), theoretical value: 960.49.

[0160] Preparation of compound 86:

[0161] The synthesis of compound 86 was based on compound 20, except that intermediate P4 was used to replace intermediate P1 to obtain compound 86. -5 The half-peak width is 23 nm.

[0162] Example 5 Synthesis of Compound 115:

[0163]

[0164]

[0165] Preparation of intermediate K5:

[0166] The synthesis of intermediate K5 refers to intermediate K1, except that raw material A4 is used to replace raw material A1, and raw material B2 is used to replace raw material B1 to obtain intermediate K5. LC-MS: Measured value: 564.28 ([M+H] + ), theoretical value: 563.10.

[0167] Preparation of intermediate P5:

[0168] The synthesis of intermediate P5 refers to intermediate P1, except that intermediate K5 is used to replace intermediate K1 to obtain intermediate P5. LC-MS: Measured value: 822.40 ([M+H] + ), theoretical value: 821.35.

[0169] Preparation of compound 115:

[0170] The synthesis of compound 115 was based on compound 20, except that intermediate P5 was used to replace intermediate P1 to obtain compound 115. -5 The half-peak width is 21 nm.

[0171] Example 6 Synthesis of Compound 118:

[0172]

[0173] Preparation of intermediate K6:

[0174] The synthesis of intermediate K6 refers to intermediate K1, except that raw material A3 is used to replace raw material A1, and raw material B2 is used to replace raw material B1 to obtain intermediate K6. LC-MS: Measured value: 584.21 ([M+H] + ), theoretical value: 583.07.

[0175] Preparation of intermediate P6:

[0176] The synthesis of intermediate P6 refers to intermediate P1, except that intermediate K6 is used to replace intermediate K1 to obtain intermediate P6. LC-MS: Measured value: 842.25 ([M+H] + ), theoretical value: 841.32.

[0177] Preparation of compound 118:

[0178] The synthesis of compound 118 was based on compound 20, except that intermediate P6 was used to replace intermediate P1 to obtain compound 118. 1HNMR (400MHz, Chloroform-d) δ8.65 (d, 1H), 7.98–7.80 (m, 3H), 7.67–7.20 (m, 25H), 7.17–6.90 (m, 5H), 2.54–2.28 (m, 2H), 1.79–1.41 (m, 6H). In toluene solution (1×10 -5 The half-peak width is 22 nm.

[0179] Example 7 Synthesis of Compound 144:

[0180]

[0181] Preparation of intermediate K7:

[0182] The synthesis of intermediate K7 refers to intermediate K1, except that raw material A5 is used to replace raw material A1, and raw material B3 is used to replace raw material B1 to obtain intermediate K7. LC-MS: Measured value: 653.18 ([M+H] + ), theoretical value: 652.13.

[0183] Preparation of intermediate P7:

[0184] The synthesis of intermediate P7 was based on intermediate P1, except that intermediate K7 was used to replace intermediate K1 to obtain intermediate P7. LC-MS: Measured value: 911.20 ([M+H] + ), theoretical value: 910.38.

[0185] Preparation of compound 144:

[0186] The synthesis of compound 144 was based on compound 20, except that intermediate P7 was used to replace intermediate P1 to obtain compound 144. 1HNMR (400 MHz, Chloroform-d) δ7.95–7.84 (m, 3H), 7.72–7.56 (m, 6H), 7.54–7.15 (m, 18H), 7.14–6.94 (m, 5H), 2.47–2.34 (m, 2H), 1.73–1.47 (m, 6H), 1.35 (s, 9H). In toluene solution (1×10 -5 The half-peak width is 26 nm.

[0187] Example 8 Synthesis of Compound 175:

[0188]

[0189]

[0190] Preparation of intermediate K8:

[0191] The synthesis of intermediate K8 refers to intermediate K1, except that raw material A6 is used to replace raw material A1, and intermediate J2 is used to replace raw material B1 to obtain intermediate K8. LC-MS: Measured value: 924.37 ([M+H] + ), theoretical value: 923.45.

[0192] Preparation of intermediate P8:

[0193] The synthesis of intermediate P8 refers to intermediate P1, except that intermediate K8 is used to replace intermediate K1 to obtain intermediate P8. LC-MS: Measured value: 1182.84 ([M+H] + ), theoretical value: 1181.70.

[0194] Preparation of compound 175:

[0195] The synthesis of compound 175 was based on compound 20, except that intermediate P8 was used instead of intermediate P1 to obtain compound 175. 1 HNMR (400MHz, Chloroform-d) δ7.44–7.37 (m, 2H), 7.36–7.27 (m, 5H), 7.24 (dd, 1H), 7.15–6.92 (m, 17H), 6.79 (s, 2H), 2.49–2.32 (m, 2H), 2.07–1.93 (m, 2H), 1.82–1.39 (m, 20H), 1.38–1.18 (m, 39H). Toluene solution (1×10 -5 The half-peak width is 27 nm.

[0196] Example 9 Synthesis of Compound 224:

[0197]

[0198] Preparation of intermediate K9:

[0199] The synthesis of intermediate K9 refers to intermediate K1, except that raw material A6 is used to replace raw material A1, and raw material B4 is used to replace raw material B1 to obtain intermediate K9. LC-MS: Measured value: 798.19 ([M+H] + ), theoretical value: 797.22.

[0200] Preparation of intermediate P9:

[0201] The synthesis of intermediate P9 refers to intermediate P1, except that intermediate K9 is used to replace intermediate K1 to obtain intermediate P9. LC-MS: Measured value: 1056.52 ([M+H] + ), theoretical value: 1055.47.

[0202] Preparation of compound 224:

[0203] The synthesis of compound 224 was based on compound 20, except that intermediate P9 was used instead of intermediate P1 to obtain compound 224. 1 HNMR (400MHz, Chloroform-d) δ8.00–7.86 (m, 3H), 7.75 (d, 1H), 7.68–7.58 (m, 3H), 7.45–7.15 (m, 14H), 7.15–6.92 (m, 13H), 2.50–2.30 (m, 2H), 1.79–1.43 (m, 6H), 1.32 (s, 18H). Toluene solution (1×10 -5 The half-peak width is 23 nm.

[0204] Example 10 Synthesis of Compound 227:

[0205]

[0206] Preparation of intermediate K10:

[0207] Raw material A4 (19.0 mmol), intermediate J1 (20.0 mmol), CuI catalyst (2 mmol), K3PO4 (45 mmol) were added to a three-necked flask in sequence, followed by the addition of 3 mmol of trans-1,2-cyclohexanediamine and 160 mL of dioxane under a nitrogen atmosphere. After stirring at 110°C for 15 hours, the reaction mixture was 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 K10. LC-MS: Measured value: 583.22 ([M+H] + ), theoretical value: 582.14.

[0208] Preparation of intermediate Q1:

[0209] The synthesis of intermediate Q1 refers to intermediate K10, except that intermediate K10 is used to replace raw material A4, and raw material B5 is used to replace intermediate J1 to obtain intermediate Q1. LC-MS: Measured value: 652.27 ([M+H] + ), theoretical value: 651.34.

[0210] Preparation of intermediate P10:

[0211] The synthesis of intermediate P10 refers to intermediate K10, except that raw material B6 is used to replace raw material A4, and intermediate Q1 is used to replace intermediate J1 to obtain intermediate P10. LC-MS: Measured value: 891.45 ([M+H] + ), theoretical value: 890.41.

[0212] Preparation of compound 227:

[0213] The synthesis of compound 227 was based on compound 20, except that intermediate P10 was used instead of intermediate P1 to obtain compound 227. 1 H NMR (400MHz, Chloroform-d) δ8.24 (m, 1H), 8.06–7.90 (m, 1H), 7.70–7.57 (m, 2H), 7.47–7.19 (m, 12H), 7.17–6.95 (m, 8H), 6.90 (d, 3H), 2.51–2.32 (m, 2H), 1.77–1.44 (m, 6H), 1.30 (d, 18H). Toluene solution (1×10 -5 The half-peak width is 25 nm.

[0214] Note: The half-peak width (FWHM) is obtained by testing the Fluorolog-3 series fluorescence spectrometer of Horiba.

[0215] The structural characteristics of the compounds obtained in each example are shown in Table 1

[0216] Table 1

[0217]

[0218] The compound of the present invention is used in a light-emitting device and can be used as a doping material for a light-emitting layer.

[0219] Device Embodiment

[0220] The following describes in detail the application effect of the OLED material synthesized by the present invention in the device through device embodiments 1-10 and device comparative examples 1-2. The device manufacturing process of device embodiments 2-10 and device comparative examples 1-2 of the present invention is exactly the same as that of device embodiment 1, and the same substrate material and electrode material are used. The film thickness of the electrode material is also the same. The difference is that the light-emitting layer material in the device is replaced. The layer structure and test results of each device embodiment are shown in Table 2 and Table 3 respectively.

[0221] Device Example 1

[0222] like Figure 1As shown, the transparent substrate layer 1 is a transparent PI film, and the ITO anode layer 2 (film thickness is 150nm) is washed, that is, washing with a cleaning agent (Semiclean M-L20), washing with pure water, drying, and then ultraviolet-ozone washing to remove organic residues on the surface of the transparent ITO. On the ITO anode layer 2 after the above washing, a vacuum evaporation device is used to evaporate HT-1 and HI-1 with a film thickness of 10nm as a hole injection layer 3, and the mass ratio of HT-1 and HI-1 is 97:3. Then evaporate HT-1 with a thickness of 60nm as a hole transport layer 4. Then evaporate EB-1 with a thickness of 30nm as an electron blocking layer 5. After the above electron blocking material is evaporated, the light-emitting layer 6 of the OLED light-emitting device is prepared, using GH-1 and GH-2 as the main materials, compound 20 as the doping material, GH-1, GH-2 and compound 20 The mass ratio is 69:30:1, and the film thickness of the light-emitting layer is 30nm. After the above-mentioned light-emitting layer 6, HB-1 was vacuum-deposited to a thickness of 5 nm, which was the hole blocking layer 7. After the above-mentioned hole blocking layer 7, ET-1 and Liq were vacuum-deposited to a thickness of 30 nm, with a mass ratio of ET-1 to Liq of 1:1. On the electron transport layer 8, a LiF layer with a thickness of 1 nm was made by vacuum evaporation, which was the electron injection layer 9. On the electron injection layer 9, a Mg:Ag electrode layer with a thickness of 80 nm was made by vacuum evaporation, with a mass ratio of Mg to Ag of 1:9, which was used as the cathode layer 10.

[0223] The following describes in detail the application effect of the OLED material synthesized by the present invention in the device through device examples 11-20 and device comparative examples 3-4. The device manufacturing process of device examples 12-20 and device comparative examples 3-4 of the present invention is exactly the same as that of device example 11, and the same substrate material and electrode material are used. The film thickness of the electrode material is also the same. The difference is that the light-emitting layer material in the device is replaced. The layer structure and test results of each device embodiment are shown in Table 2 and Table 3 respectively.

[0224] Device Example 11

[0225] The transparent substrate layer 1 is a transparent PI film, and the ITO anode layer 2 (film thickness is 150nm) is washed, that is, washed with a cleaning agent (Semiclean M-L20), washed with pure water, dried, and then washed with ultraviolet-ozone to remove organic residues on the surface of the transparent ITO. On the ITO anode layer 2 after the above washing, a vacuum evaporation device is used to evaporate HT-1 and HI-1 with a film thickness of 10nm as the hole injection layer 3, and the mass ratio of HT-1 to HI-1 is 97:3. Then, HT-1 with a thickness of 60nm is evaporated as the hole transport layer 4. Then, EB-1 with a thickness of 30nm is evaporated as the electron blocking layer 5. After the above-mentioned electron blocking material is deposited, the light-emitting layer 6 of the OLED light-emitting device is prepared, using GH-1 and GH-2 as the main materials, GD-1 as the first doping material, and compound 20 as the second doping material. The mass ratio of GH-1, GH-2, GD-1 and compound 20 is 66:30:3:1, and the thickness of the light-emitting layer is 30nm. After the above-mentioned light-emitting layer 6, HB-1 is vacuum-deposited with a film thickness of 5nm. This layer is the hole blocking layer 7. After the above-mentioned hole blocking layer 7, ET-1 and Liq are vacuum-deposited. The mass ratio of ET-1 and Liq is 1:1, and the film thickness is 30nm. This layer is the electron transport layer 8. On the electron transport layer 8, a LiF layer with a film thickness of 1nm is prepared by a vacuum evaporation device. This layer is the electron injection layer 9. On the electron injection layer 9, a Mg:Ag electrode layer with a film thickness of 80nm is prepared by a vacuum evaporation device. The mass ratio of Mg and Ag is 1:9. This layer is used as the cathode layer 10.

[0226] The molecular structure formula of the relevant materials is shown below:

[0227]

[0228] After the OLED light emitting device is completed as described above, the anode and cathode are connected by a known driving circuit, and the current efficiency and life of the device are measured. The device examples and comparative examples prepared by the same method are shown in Table 2; the test results of the current efficiency and life of the obtained device are shown in Table 3.

[0229] Table 2

[0230]

[0231]

[0232] Table 3

[0233]

[0234] Note: Current efficiency and luminescence peak are tested using IVL (current-voltage-luminance) test system (Suzhou Fushida Scientific Instrument Co., Ltd.); life test system is EAS-62C OLED device life tester from Japan System Technology Co., Ltd.; LT95 refers to the time it takes for the device brightness to decay to 95%; all data are at 10mA / cm 2 Next test.

[0235] It can be seen from the device data results in Table 3 that, compared with device comparison examples 1-4, the organic light-emitting device of the present invention, whether in a single-doping system or a double-doping system, has a greatly improved current efficiency and lifespan relative to OLED devices of known materials; when an exciton-sensitizing material is used as the first doping, the device efficiency is significantly improved compared to a single-doping system.

[0236] In summary, the above are only 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 in 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 general formula (1): In the general formula (1), Z is C-R1; R1, which is the same or different each time, is H, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups; adjacent R1 are not connected or connected to form a ring; M1 and M2 represent substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl; Ar1 and Ar2 are independently 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 heteroaryl; Ar2 and M1 are not connected or connected to form a ring; The substituents for the substituent groups are selected from halogen atoms, deuterium atoms, cyano groups, C1-C 10 Alkyl, C5-C 10 Cycloalkyl, C5-C 10 Cycloalkenyl, C1-C 10 Alkoxy, C6-C 30 Aryl, C3-C 30 one or more of heteroaryl groups; The heteroatom in the heteroaryl group is selected from one of O, S, N and Si.

2. The resonance type organic compound according to claim 1, characterized in that The structure of the resonance type organic compound is shown in any one of the general formulas (1-1) to (1-2): In general formula (1-1) to general formula (1-2), the definitions of Z, M1, M2, Ar1 and Ar2 are the same as those in claim 1; Z1, Z2, Z3, Z4, Z5, Z6, and Z7 are independently represented by CH or C-R2; R2, which is the same or different each time, represents a deuterium atom, a halogen atom, a cyano group, a C1-C 10 Alkyl, C6-C 30 Aryl, C3-C 30 One of the heteroaryl groups; adjacent R2 are not connected or connected to form a ring; The heteroatom in the heteroaryl group is selected from one of O, S, N and Si.

3. The resonance type organic compound according to claim 1, characterized in that The M1 is represented by any of the following ring structures: The M2 is represented by any of the following ring structures: In the above formula, Z is represented by C-R1; R1, which is the same or different each time, is represented by H, a deuterium atom, a halogen atom, a cyano group, a C1-C 10 Alkyl, C6-C 30 Aryl, C3-C 30 One of the heteroaryl groups; adjacent R1 are not connected or connected to form a ring; 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 each time appears, the same or different, and represents hydrogen, 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 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 phenanthrenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted furanyl group, 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 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted triazineyl, substituted or unsubstituted 4a,9a-dimethyl-9-phenyl-1,2,3,4-tetrahydrocarbazole; Ar1 and Ar2 are independently 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 biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, 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 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl; The M1 and M2 are represented by substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolyl, substituted or unsubstituted furyl, 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 9,9-dimethylfluorenyl, substituted or unsubstituted indole [3,2,1-jk] carbazolyl, substituted or unsubstituted 4a,9a-dimethyl-9-phenyl-1,2,3,4-tetrahydrocarbazole; The substituent for the substituent group is optionally selected from 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-amyl group, a tert-butyl group, an n-butyl group, a methoxy group, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl 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, and an azaphenanthryl group.

5. The resonance type organic compound according to claim 2, characterized in that: The R1 each time appears, the same or different, and represents hydrogen, 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 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 phenanthrenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted furanyl group, 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 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted triazineyl, substituted or unsubstituted 4a,9a-dimethyl-9-phenyl-1,2,3,4-tetrahydrocarbazole; The R2 each time appears the same or different represents a deuterium atom, a halogen atom, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a quinolyl group, a furyl group, a thienyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, a spirofluorenyl group, a triazine group, a 4a,9a-dimethyl-9-phenyl-1,2,3,4-tetrahydrocarbazole group; Ar1 and Ar2 are independently 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 biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, 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 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl; The M1 and M2 are represented by substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolyl, substituted or unsubstituted furyl, 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 9,9-dimethylfluorenyl, substituted or unsubstituted indole [3,2,1-jk] carbazolyl, substituted or unsubstituted 4a,9a-dimethyl-9-phenyl-1,2,3,4-tetrahydrocarbazole; The substituent for the substituent group is optionally selected from 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-amyl group, a tert-butyl group, an n-butyl group, a methoxy group, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl 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, and an azaphenanthryl group.

6. The resonance type organic compound according to claim 3, characterized in that: The R1 each time appears the same or different represents hydrogen, a deuterium atom, a halogen atom, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a quinolyl group, a furyl group, a thienyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, a spirofluorenyl group, a triazine group, a 4a,9a-dimethyl-9-phenyl-1,2,3,4-tetrahydrocarbazole group; Ar1 and Ar2 are independently 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 biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, 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 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl; The substituent for the substituent group is optionally selected from 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-amyl group, a tert-butyl group, an n-butyl group, a methoxy group, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl 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, and an azaphenanthryl group.

7. A resonance type organic compound, characterized in that The structure of the resonance type organic compound is shown in any one of the general formulas (1-3) to (1-9): In the general formula (1-3) to the general formula (1-9), Z is represented by C-R1; R1, which is the same or different each time, is represented by H, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups; adjacent R1 are not connected or connected to form a ring; Ar2 represents a 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 heteroaryl; Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8, Z9, Z 10 , Z 11 Each independently represents CH or C-R2; R2, which is the same or different each time, represents a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups; adjacent R2 are not connected or connected to form a ring; Ar3 represents a 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 heteroaryl; The substituents for the substituent groups are selected from halogen atoms, deuterium atoms, cyano groups, C1-C 10 Alkyl, C5-C 10 Cycloalkyl, C5-C 10 Cycloalkenyl, C1-C 10 Alkoxy, C6-C 30 Aryl, C3-C 30 one or more of heteroaryl groups; The heteroatom in the heteroaryl group is selected from one of O, S, N and Si.

8. The resonance type organic compound according to claim 7, characterized in that: The R1 each time appears, the same or different, and represents hydrogen, 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 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 phenanthrenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted furanyl group, 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 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted triazineyl, substituted or unsubstituted 4a,9a-dimethyl-9-phenyl-1,2,3,4-tetrahydrocarbazole; The R2 each time appears, 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 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 phenanthrenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted furanyl group , 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 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted triazine, substituted or unsubstituted 4a,9a-dimethyl-9-phenyl-1,2,3,4-tetrahydrocarbazole; Ar2 and Ar3 are independently 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 biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, 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 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl; The substituent for the substituent group is optionally selected from 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-amyl group, a tert-butyl group, an n-butyl group, a methoxy group, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl 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, and an azaphenanthryl group.

9. A resonance type organic compound, characterized in that: The structure of the resonance type organic compound is shown in any one of the general formulas (2-1) to (2-8): In the general formula (2-1) to the general formula (2-8), Z is represented by C-R1; R1, which is the same or different each time, is represented by H, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups; adjacent R1 are not connected or connected to form a ring; M1 represents a substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl; Ar1 and Ar2 are independently 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 heteroaryl; Ar2 and M1 are not connected or connected to form a ring; The substituents for the substituent groups are selected from halogen atoms, deuterium atoms, cyano groups, C1-C 10 Alkyl, C5-C 10 Cycloalkyl, C5-C 10 Cycloalkenyl, C1-C 10 Alkoxy, C6-C 30 Aryl, C3-C 30 one or more of heteroaryl groups; The heteroatom in the heteroaryl group is selected from one of O, S, N and Si.

10. The resonance type organic compound according to claim 9, characterized in that: The R1 each time appears, the same or different, and represents hydrogen, 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 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 phenanthrenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted furanyl group, 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 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted triazineyl, substituted or unsubstituted 4a,9a-dimethyl-9-phenyl-1,2,3,4-tetrahydrocarbazole; Ar1 and Ar2 are independently 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 biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, 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 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl; The M1 represents 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 9,9-dimethylfluorenyl group, a substituted or unsubstituted indole [3,2,1-jk] carbazolyl group, or a substituted or unsubstituted 4a,9a-dimethyl-9-phenyl-1,2,3,4-tetrahydrocarbazole group; The substituent for the substituent group is optionally selected from 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-amyl group, a tert-butyl group, an n-butyl group, a methoxy group, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl 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, and an azaphenanthryl group.

11. A resonance type organic compound, characterized in that: The structure of the resonance type organic compound is shown in general formula (3-3) to general formula (3-9): In the general formula (3-1) to the general formula (3-9), Z is represented by C-R1; R1, which is the same or different each time, is represented by H, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups; adjacent R1 are not connected or connected to form a ring; The Z1, Z2, and Z3 are independently represented by CH or C-R2; R2 is the same or different each time and represents a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups; adjacent R2 are not connected or connected to form a ring; The substituents for the substituent groups are selected from halogen atoms, deuterium atoms, cyano groups, C1-C 10 Alkyl, C5-C 10 Cycloalkyl, C5-C 10 Cycloalkenyl, C1-C 10 Alkoxy, C6-C 30 Aryl, C3-C 30 one or more of heteroaryl groups; The heteroatom in the heteroaryl group is selected from one of O, S, N and Si.

12. The resonance type organic compound according to claim 11, characterized in that: The R1 each time appears, the same or different, and represents hydrogen, 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 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 phenanthrenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted furanyl group, 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 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted triazineyl, substituted or unsubstituted 4a,9a-dimethyl-9-phenyl-1,2,3,4-tetrahydrocarbazole; The R2 each time appears, 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 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 phenanthrenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted furanyl group , 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 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted triazine, substituted or unsubstituted 4a,9a-dimethyl-9-phenyl-1,2,3,4-tetrahydrocarbazole; The substituent for the substituent group is optionally selected from 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-amyl group, a tert-butyl group, an n-butyl group, a methoxy group, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl 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, and an azaphenanthryl group.

13. 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:

14. 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 of the organic light-emitting device comprises the resonance-type organic compound according to any one of claims 1 to 13. 15 . The organic light-emitting device according to claim 14 , wherein the functional layer comprises a light-emitting layer, the light-emitting layer comprises a host material and a doping material, and the doping material is the resonance-type organic compound according to any one of claims 1 to 13 .

16. The organic light-emitting device according to claim 14, wherein the functional layer comprises a light-emitting layer, and the light-emitting layer comprises a first main material, a second main material and a doping material, and at least one of the first main material and the second main material is a TADF material, and the doping material is the resonance-type organic compound according to any one of claims 1 to 13.

17. The organic light-emitting device according to claim 15, wherein the light-emitting layer comprises a host material, an exciton sensitizing material and a doping material, wherein: The exciton sensitizing 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 to 13.

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