A resonant organic compound and an organic electroluminescent device containing the same

Abstract

The present invention relates to a resonance-type organic compound and an organic electroluminescent device containing the same, belonging to the field of semiconductor technology. The structure of the compound provided by the present invention is shown in general formula (1): When the compound of the present invention is used as a green light doping material in the light-emitting layer material of an OLED light-emitting device, the current efficiency of the device is significantly improved, and the luminescent 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 an organic electroluminescent device containing the same. Background Art

[0002] Traditional fluorescent doped materials, limited by early technology, can only utilize the 25% of singlet excitons formed by electrical excitation to emit light. This results in low internal quantum efficiency (up to 25%) and external quantum efficiency generally below 5%, significantly lagging behind the efficiency of phosphorescent devices. However, phosphorescent materials, due to the strong spin-orbit coupling at the heavy atom center that enhances intersystem crossing, can effectively utilize singlet and triplet excitons formed by electrical excitation to emit light, resulting in a device internal quantum efficiency of 100%.

[0003] With the advent of the 5G era, higher requirements are being placed on color rendering standards. In addition to being efficient and stable, luminescent materials also need to have a narrower half-width to improve the color purity of the device's luminescent color. Fluorescent doping materials can achieve high fluorescence quantum and narrow half-width through molecular engineering. Blue fluorescent doping materials have achieved a phased breakthrough, and the half-width of boron-based materials can be reduced to below 30nm. However, research in the green light region, to which the human eye is more sensitive, has mainly focused on phosphorescent doping materials. However, their luminescent peak shape is difficult to narrow through simple methods. Therefore, to meet higher color rendering standards, it is of great significance to study efficient green fluorescent doping 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, fully utilizes triplet excitons, and transfers energy to fluorescent doping materials through energy transfer, which can also achieve 100% device internal 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 resonant structures 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 TADF material with a difference between the lowest singlet state and the lowest triplet state energy level of less than or equal to 0.2eV as the main body, and a boron-containing material as the doping luminescent layer combination technology; 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.

[0006] The DABNA-1 structure publicly reported in the paper (CAS: 1689552-89-3, 10.1002 / adma.201505491) is a good blue light building unit; in 2020, the prior art disclosed a compound introducing a pyrene ring (CN114315876A), which adjusted the light color and improved the device life to a certain extent. Although the above solutions have improved the life of the device to a certain extent, there is still a big gap with the current industry needs. Summary of the Invention

[0007] To address the above-mentioned problems in the prior art, the present invention provides a resonant organic compound and an organic electroluminescent device comprising the same. The structure of the resonant organic compound of the present invention is shown in general formula (1). By simultaneously introducing a pyrene ring and a five-membered heterocyclic structure, a highly efficient resonant organic compound can be formed, which has the effects of significantly adjusting light color, narrowing the half-peak width, and enhancing molecular stability, thereby improving the efficiency and life of the device.

[0008] The technical solution of the present invention is as follows: a resonance type organic compound, the structure of the resonance type organic compound is shown in the general formula (1):

[0009]

[0010] In the general formula (1), M1 and M2 rings are substituted or unsubstituted C6-C 30 Aromatic ring, substituted or unsubstituted C4-C 30 heteroaromatic rings;

[0011] Z is represented by C-R1; R1, 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 or silyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C1-C 10 aryloxy, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of heteroaryl, substituted or unsubstituted arylamine;

[0012] X1 and X2 represent O, S, N(R2), and R2 represents a substituted or unsubstituted C1-C 10 Alkyl or silyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C3-C 10substituted or unsubstituted arylamine, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 and R2 may be connected to the M1 or M2 ring to form a ring.

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

[0014] The heteroatoms in the heteroaryl group are selected from one or more of O, S, N, and Si.

[0015] Preferably, at least one of the M1 and M2 rings represents a structure represented by general formula (1-1);

[0016]

[0017] “*” indicates the site of connection;

[0018] Z is represented by C-R1; R1, 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 or silyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C1-C 10 aryloxy, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of heteroaryl, substituted or unsubstituted arylamine;

[0019] The X3 is represented by O, S, N (R3); R3 is the same or different each time and represents a substituted or unsubstituted C1-C 10 Alkyl or silyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups;

[0020] The substituents for the substituent group are optionally selected from halogen atoms, deuterium atoms, cyano groups, C1-C10 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;

[0021] The heteroatoms in the heteroaryl group are selected from one or more of O, S, N, and Si.

[0022] In a preferred embodiment, the M1 ring represents a structure represented by the general formula (1-1), and the M2 ring represents a substituted or unsubstituted C6-C 30 Aromatic ring, substituted or unsubstituted C4-C 30 heteroaromatic ring.

[0023] In a preferred embodiment, the M2 ring represents a structure represented by the general formula (1-1), and the M1 ring represents a substituted or unsubstituted C6-C 30 Aromatic ring, substituted or unsubstituted C4-C 30 heteroaromatic ring.

[0024] In a preferred embodiment, the M1 and M2 rings represent the structure shown in general formula (1-1).

[0025] In a preferred embodiment, the structure of the resonance-type organic compound is shown in any one of general formulas (2) to (6):

[0026]

[0027] In general formula (2) to general formula (6), the definitions of Z, X1, and X2 are the same as those defined above;

[0028] The X3 is represented by O, S, N (R3); each occurrence of R3 is the same or different and represents a substituted or unsubstituted C1-C 10 Alkyl or silyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups;

[0029] The X4 is represented by O, S, N (R4); each occurrence of R4 is the same or different and represents a substituted or unsubstituted C1-C 10 Alkyl or silyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C30 One of the heteroaryl groups;

[0030] The substituents for the substituent group are optionally selected from halogen atoms, deuterium atoms, cyano groups, C1-C 10 Alkyl, C5-C 10 Cycloalkyl, C5-C 10 Cycloalkenyl, C1-C 10 Alkoxy, C3-C 20 Cycloalkyl, C6-C 30 Aryl, C3-C 30 one or more of heteroaryl groups;

[0031] The heteroatoms in the heteroaryl group are selected from one or more of O, S, N, and Si.

[0032] In a preferred embodiment, the structure of the resonance-type organic compound is shown in any one of general formulas (7) to (13):

[0033]

[0034] In general formula (7) to general formula (13), the definition of Z is the same as that defined above;

[0035] The X3 is represented by O, S, N (R3); R3 is the same or different each time and represents a substituted or unsubstituted C1-C 10 Alkyl or silyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups;

[0036] The X4 is represented by O, S, N (R4); each occurrence of R4 is the same or different and represents a substituted or unsubstituted C1-C 10 Alkyl or silyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups;

[0037] The substituents for the substituent group are optionally selected from halogen atoms, deuterium atoms, cyano groups, C1-C 10 Alkyl, C5-C 10 Cycloalkyl, C5-C 10 Cycloalkenyl, C1-C 10 Alkoxy, C3-C 20 Cycloalkyl, C6-C 30 Aryl, C3-C 30one or more of heteroaryl groups;

[0038] The heteroatoms in the heteroaryl group are selected from one or more of O, S, N, and Si.

[0039] In a preferred embodiment, the structure of the resonance-type organic compound is shown in any one of the general formulas (14) to (21):

[0040]

[0041] In general formula (14) to general formula (21), the definition of Z is the same as that defined above;

[0042] The X3 is represented by O, S, N (R3); each occurrence of R3 is the same or different and represents a substituted or unsubstituted C1-C 10 Alkyl or silyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups;

[0043] The X4 is represented by O, S, N (R4); each occurrence of R4 is the same or different and represents a substituted or unsubstituted C1-C 10 Alkyl or silyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups;

[0044] The R a 、R b 、R c 、R d 、R e Represented by H, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C 10 Alkyl or silyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C1-C 10 aryloxy, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of heteroaryl, substituted or unsubstituted arylamine;

[0045] The substituents for the substituent group are optionally selected from halogen atoms, deuterium atoms, cyano groups, C1-C 10 Alkyl, C5-C 10Cycloalkyl, 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;

[0046] The heteroatoms in the heteroaryl group are selected from one or more of O, S, N, and Si.

[0047] In a preferred embodiment, the structure of the resonance-type organic compound is shown in any one of general formulas (22) to (29):

[0048]

[0049] In general formula (22) to general formula (29), Z, X3, X4, R a 、R c 、R d 、R e is as defined above;

[0050] In a preferred embodiment, R1 is hydrogen, deuterium, tritium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopentyl, 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 phenanthrenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, 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 amino, substituted or unsubstituted triazinyl, substituted or unsubstituted adamantyl;

[0051] R2 is 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 vinyl group, a substituted or unsubstituted propenyl 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 furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted triazinyl group, or a substituted or unsubstituted adamantyl group;

[0052] R3 and R4 are each selected from the group consisting of 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 phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted triazinyl group, and a substituted or unsubstituted adamantyl group.

[0053] The M1 and M2 rings are represented by a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted pyrene ring, a substituted or unsubstituted furan ring, a substituted or unsubstituted thiophene ring, a substituted or unsubstituted pyrrole ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted indole ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted dibenzothiophene ring, or a substituted or unsubstituted carbazole ring;

[0054] The R a 、R b 、R c 、R d 、R e represented by hydrogen, deuterium, tritium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopentyl, 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 phenanthrenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl , substituted or unsubstituted furyl, substituted or unsubstituted thienyl, 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 amino, substituted or unsubstituted triazinyl, substituted or unsubstituted adamantyl;

[0055] The substituents for the substituent group are 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 phenanthrenyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a quinolyl group, an isoquinolyl group, a furyl 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 azaphenanthrenyl group.

[0056] Preferably, the R2 is represented by the structure shown below:

[0057]

[0058] Preferably, R1, R3, R4, R a 、R b 、R c 、R d 、R e It is represented by the following structure:

[0059] In a preferred embodiment, the specific structural formula of the resonance-type organic compound is any one of the following structures:

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071] The present invention also provides an organic light-emitting device comprising a cathode, an anode and a functional layer, wherein the functional layer is located between the cathode and the anode, and the functional layer of the organic light-emitting device comprises the resonance-type organic compound.

[0072] In a preferred embodiment, the functional layer of the organic light-emitting device 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.

[0073] In a preferred embodiment, the light-emitting layer of the organic light-emitting device comprises a first host material, a second host material and a doping material, at least one of the first host material and the second host material is a TADF material, and the doping material is the resonance-type organic compound.

[0074] In a preferred embodiment, the light-emitting layer of the organic light-emitting device 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.

[0075] Compared with the prior art, the present invention has the following beneficial technical effects:

[0076] (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.

[0077] (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 enhance the luminous efficiency of the device;

[0078] (3) The compounds of the present invention reduce the intramolecular ring tension by introducing a pentacyclic heterocyclic structure, which is beneficial to improving the bond stability of the molecule;

[0079] (4) The compound of the present invention adds a cyclic structure to the five-membered heterocyclic ring, which protects the olefin bond and helps to improve the thermal stability of the molecule;

[0080] The compound of the present invention 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

[0081] 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;

[0082] 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

[0083] The present invention will be described in detail below with reference to the accompanying drawings and embodiments.

[0084] In the present invention, when describing electrodes, organic electroluminescent devices, and other structures, terms such as "upper," "lower," "top," and "bottom" that indicate orientation refer only to a particular state and do not imply that the structure can exist only in the described orientation. Conversely, if the structure can be repositioned, such as inverted, the orientation of the structure will change accordingly. Specifically, in the present invention, the "bottom" or "lower" side of an electrode refers to the side of the electrode closest to the substrate during fabrication, while the opposite side, farther from the substrate, is the "top" or "upper" side.

[0085] As the substrate for the organic electroluminescent device of the present invention, any substrate commonly used for organic electroluminescent devices can be used. Examples include transparent substrates such as glass or transparent plastic substrates, and opaque substrates such as silicon substrates. Different substrates have varying mechanical strength, thermal stability, transparency, surface smoothness, and water resistance. Depending on the properties of the substrate, its use varies. In the present invention, a transparent PI film substrate is preferably used. The thickness of the substrate is not particularly limited.

[0086] 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 50-500 nm, preferably 70-300 nm, and more preferably 100-200 nm.

[0087] 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.

[0088] 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.

[0089] As materials for the hole injection layer, the hole transport layer, and the electron blocking layer, any material can be selected from known materials used in OLED devices.

[0090] Examples of the above materials include phthalocyanine derivatives, triazole derivatives, triarylmethane derivatives, triarylamine derivatives, oxazole derivatives, oxadiazole derivatives, hydrazone derivatives, stilbene derivatives, pyridinoline derivatives, polysilane derivatives, imidazole derivatives, phenylenediamine derivatives, amino-substituted quilone derivatives, styrylanthracene derivatives, styrylamine derivatives and other styrene compounds, 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 other 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.

[0091] Furthermore, depending on the device configuration, the hole transport layer between the electron blocking and hole injection layers of the organic electroluminescent device can be a single layer or a stacked structure of multiple hole transport materials. In this document, the thickness of the various hole carrier conducting layers with different functions described above is not particularly limited.

[0092] The hole injection layer contains a host 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 hole injection from the anode to the organic film layer, the HOMO energy level of the host organic material used in the anode interface buffer layer must have certain characteristics with the P-doped material. Only then can the charge transfer state between the host material and the dopant material be achieved, and ohmic contact between the buffer layer and the anode can be achieved, achieving efficient injection and conduction of holes from the electrode.

[0093] 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.

[0094] Therefore, in one embodiment of the present invention, in order to better inject holes, the hole injection layer further includes a P-type dopant 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(cyanoformylidene))tris(2,3,5,6-tetrafluorobenzyl); or metal oxides, such as tungsten oxide and molybdenum oxide, but not limited thereto.

[0095] In the hole injection layer of the present invention, the ratio of the hole transport material to the P-type doping material is 99:1-95:5, preferably 99:1-97:3, based on mass.

[0096] 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.

[0097] 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.

[0098] 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.

[0099] 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.

[0100] 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.

[0101] The light-emitting layer may contain a single host material or a dual host material;

[0102] The dual host material comprises a first host material and a second host material, wherein at least one of the first host material and the second host material is preferably a TADF material;

[0103] TADF materials exhibit thermally activated delayed fluorescence (TADF), characterized by a small energy difference between the first excited singlet and triplet states. This allows for simultaneous utilization of both singlet and triplet excitons within the device, resulting in a near 100% utilization rate of electrically generated excitons within the device. Compared to traditional fluorescent materials, TADF materials exhibit higher exciton utilization.

[0104] The light-emitting layer may comprise a host material, an exciton-sensitizing material, and a dopant material;

[0105] Exciton-sensitizing materials refer to materials that enable the luminescent material in the luminescent layer to fully utilize electrically induced excitons, thereby ultimately producing an emission spectrum of the sensitized material. Exciton sensitizers may perform functions such as exciton capture, exciton conversion, and exciton transfer in electroluminescent devices. The combination of the resonant organic compound represented by general formula (1) of the present invention and the exciton-sensitizing material significantly improves device efficiency, exciton annihilation, and efficiency reduction in the device.

[0106] In the light-emitting layer of the present invention, the ratio of the host material to the dopant material used is 99:1-70:30, preferably 99:1-85:15 and more preferably 97:3-87:13, based on mass.

[0107] The thickness of the light-emitting layer can be adjusted to optimize the luminous efficiency and 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.

[0108] 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.

[0109] The hole blocking layer is a layer that blocks 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 performance of the device. The hole blocking layer of the present invention can be arranged above 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 bathocuproine (referred to as BCP), metal complexes of hydroxyquinoline derivatives such as aluminum (III) bis(2-methyl-8-quinolinol)-4-phenylphenolate (BAlq), various rare earth complexes, oxazole derivatives, triazole derivatives, triazine derivatives, pyrimidine derivatives such as 9,9'-(5-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-1,3-phenylene)bis(9H-carbazole), etc. The thickness of the hole blocking layer of the present invention can be 2-200 nm, preferably 5-150 nm, but the thickness is not limited to this range.

[0110] The electron transport layer can be disposed on the light-emitting layer or (if present) the hole blocking layer. The electron transport layer material is a material that readily accepts 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, 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-fluoren-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.

[0111] The electron injection layer may be provided 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 materials 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 such as cesium fluoride, cesium carbonate or cesium azide. The thickness of the electron injection layer of the present invention may be 0.1-5 nm, preferably 0.5-3 nm and more preferably 0.8-1.5 nm, but the thickness is not limited to this range.

[0112] 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, but is not limited to, 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. The thickness of the cathode depends on the material used.

[0113] 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 or metal can, or a thin film covering the entire surface of the organic layer.

[0114] The method for preparing an organic electroluminescent device of the present invention comprises sequentially laminating an anode, a hole injection layer, a hole transport layer, an electron blocking layer, an organic film layer, an electron transport layer, an electron injection layer, and a cathode, and optionally a cover layer, on a substrate. 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, vacuum evaporation is preferably used to form the various layers. Those skilled in the art can conventionally select the various process conditions in the vacuum evaporation method according to actual needs.

[0115] Synthesis Example

[0116] 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;

[0117] Example 1 Synthesis of Compound 51:

[0118]

[0119] Preparation of intermediate J1:

[0120] To a three-necked flask were added raw material A1 (5.0 mmol), raw material B1 (5.0 mmol), 0.5 mmol of CuI catalyst, and K3PO4 (15 mmol), followed by the addition of 0.75 mmol of trans-1,2-cyclohexanediamine and 160 mL of N,N-dimethylformamide under a nitrogen atmosphere. After stirring at 110°C for 16 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 J1. LC-MS: Measured value: 616.32 ([M+H] + ), exact mass: 615.25.

[0121] Preparation of intermediate K1:

[0122] The synthesis of intermediate K1 was based on intermediate J1, except that intermediate J1 was used to replace raw material A1, and raw material C1 was used to replace raw material B1 to obtain intermediate K1. LC-MS: Measured value: 801.56 ([M+H] + ), exact mass: 800.47.

[0123] Preparation of compound 51:

[0124] In a three-necked flask, under nitrogen protection, 2 mmol of boron tribromide and 1 mmol of intermediate K1 were dissolved in 30 mL of 1,2,4-trichlorobenzene. After stirring at 180°C for 24 hours, the reaction mixture was diluted with dichloromethane (50 mL) and 100 mL of sodium phosphate buffer solution (pH = 6) was added at 0°C. The aqueous layer was separated and extracted with dichloromethane (100 mL, 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 51. LC-MS: Measured value: 809.59 ([M+H] + ), exact mass: 808.46. 1 H NMR (400MHz, Chloroform-d) δ8.20 (m, 1H), 7.94–7.85 (m, 1H), 7.66–7.52 (m, 4H), 7.49–7.39 (m, 2H), 7.35–7.24 (m, 2H), 7.20–6.96 (m, 11H), 2.60–1.89 (m, 36H). The toluene solution (1×10 -5 M) has a FWHM of 24 nm.

[0125] Example 2 Synthesis of Compound 92:

[0126]

[0127] Preparation of intermediate J2:

[0128] The synthesis of intermediate J2 was similar to that of intermediate J1, except that raw material B2 was used instead of raw material B1 to obtain intermediate J2. LC-MS: Measured value: 660.27 ([M+H] + ), exact mass: 659.22.

[0129] Preparation of intermediate K2:

[0130] The synthesis of intermediate K2 was based on intermediate J1, except that intermediate J2 was used to replace raw material A1, and raw material C1 was used to replace raw material B1 to obtain intermediate K2. LC-MS: Measured value: 845.56 ([M+H] + ), exact mass: 844.44.

[0131] Preparation of compound 92:

[0132] The synthesis of compound 92 was based on compound 51, except that intermediate K2 was used instead of intermediate K1 to obtain the target compound 92. LC-MS: Measured value: 853.51 ([M+H] +), exact mass: 852.43. 1 H NMR (400MHz, Chloroform-d) δ8.57 (d, 1H), 8.23 ​​(m, 1H), 7.96–7.82 (m, 1H), 7.68–7.25 (m, 17H), 7.23–6.98 (m, 6H), 2.97–2.54 (m, 27H). The toluene solution (1×10 -5 M) has a FWHM of 26 nm.

[0133] Example 3 Synthesis of Compound 107:

[0134]

[0135]

[0136] Preparation of intermediate J3:

[0137] The synthesis of intermediate J3 was similar to that of intermediate J1, except that raw material B3 was used instead of raw material B1 to obtain intermediate J3. LC-MS: Measured value: 614.33 ([M+H] + ), exact mass: 613.23.

[0138] Preparation of intermediate K3:

[0139] The synthesis of intermediate K3 was based on intermediate J1, except that intermediate J3 was used to replace raw material A1, and raw material C2 was used to replace raw material B1 to obtain intermediate K3. LC-MS: Measured value: 799.42 ([M+H] + ), exact mass: 798.45.

[0140] Preparation of compound 107:

[0141] The synthesis of compound 107 was based on compound 51, except that intermediate K3 was used instead of intermediate K1 to obtain the target compound 107. LC-MS: Measured value: 807.48 ([M+H] + ), accurate mass: 806.44. The toluene solution (1×10 - 5 M) has a FWHM of 22 nm.

[0142] Example 4 Synthesis of Compound 145:

[0143]

[0144] Preparation of intermediate J4:

[0145] The synthesis of intermediate J4 was based on intermediate J1, except that raw material B4 was used instead of raw material B1 to obtain intermediate J4. LC-MS: Measured value: 748.29 ([M+H] + ), exact mass: 747.34.

[0146] Preparation of intermediate K4:

[0147] The synthesis of intermediate K4 was based on intermediate J1, except that intermediate J4 was used to replace raw material A1, and raw material C3 was used to replace raw material B1 to obtain intermediate K4. LC-MS: Measured value: 1005.73 ([M+H] + ), exact mass: 1004.60.

[0148] Preparation of compound 145:

[0149] The synthesis of compound 145 was based on compound 51, except that intermediate K4 was used instead of intermediate K1 to obtain the target compound 145. LC-MS: Measured value: 1013.64 ([M+H] + ), exact mass: 1012.59. 1 H NMR (400MHz, Chloroform-d) δ8.24 (m, 1H), 7.97–7.86 (m, 1H), 7.80–7.75 (m, 1H), 7.68–7.36 (m, 9H), 7.33–6.95 (m, 11H), 2.83–2.28 (m, 54H). The toluene solution (1×10 -5 M) has a FWHM of 23 nm.

[0150] Example 5 Synthesis of Compound 177:

[0151]

[0152] Preparation of intermediate K5:

[0153] The synthesis of intermediate K5 refers to intermediate J1, except that intermediate J3 is used to replace raw material A1, and raw material C4 is used to replace raw material B1 to obtain intermediate K5. LC-MS: Measured value: 871.55 ([M+H] + ), exact mass: 870.49.

[0154] Preparation of compound 177:

[0155] The synthesis of compound 177 was based on compound 51, except that intermediate K5 was used instead of intermediate K1 to obtain the target compound 177. LC-MS: Measured value: 879.57 ([M+H] + ), exact mass: 878.48.1 H NMR (400MHz, Chloroform-d) δ8.95 (d, 1H), 8.42–8.31 (m, 1H), 8.15 (m, 1H), 7.96–7.86 (m, 2H), 7.84–7.76 (m, 1H), 7.67–7.40 (m, 6H), 7.17–6.95 (m, 6H), 2.73–2.03 (m, 45H). The toluene solution (1×10 -5 M) has a FWHM of 25 nm.

[0156] Example 6 Synthesis of Compound 244:

[0157]

[0158] Preparation of intermediate K6:

[0159] To a three-necked flask were added raw material A1 (5.0 mmol), raw material C3 (10.0 mmol), CuI catalyst 0.8 mmol, and K3PO4 (20 mmol), followed by the addition of 1.0 mmol of trans-1,2-cyclohexanediamine and 160 mL of N,N-dimethylformamide under a nitrogen atmosphere. After stirring at 110°C for 20 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 K6. LC-MS: Measured value: 929.53 ([M+H] + ), exact mass: 928.48.

[0160] Preparation of compound 244:

[0161] The synthesis of compound 244 was based on compound 51, except that intermediate K6 was used instead of intermediate K1 to obtain the target compound 244. LC-MS: Measured value: 937.41 ([M+H] + ), exact mass: 936.47. 1 H NMR (400MHz, Chloroform-d) δ8.05–7.96 (m, 2H), 7.85–7.76 (m, 2H), 7.62–7.52 (m, 6H), 7.46 (dd, 2H), 7.15–6.97 (m, 8H), 2.65–2.08 (m, 45H). The toluene solution (1×10 -5 M) has a FWHM of 29 nm.

[0162] Example 7 Synthesis of Compound 252:

[0163]

[0164] Preparation of intermediate J7:

[0165] The synthesis of intermediate J7 was similar to that of intermediate J1, except that raw material C3 was used instead of raw material B1 to obtain intermediate J7. LC-MS: Measured value: 672.16 ([M+H] + ), exact mass: 671.22.

[0166] Preparation of intermediate K7:

[0167] The synthesis of intermediate K7 was based on intermediate J1, except that intermediate J7 was used to replace raw material A1, and raw material C4 was used to replace raw material B1 to obtain intermediate K7. LC-MS: Measured value: 929.58 ([M+H] + ), exact mass: 928.48.

[0168] Preparation of compound 252:

[0169] The synthesis of compound 252 was based on compound 51, except that intermediate K7 was used instead of intermediate K1 to obtain the target compound 252. LC-MS: Measured value: 937.54 ([M+H] + ), exact mass: 936.47. 1 H NMR (400MHz, Chloroform-d) δ8.20 (m, 1H), 7.96–7.87 (m, 1H), 7.86–7.75 (m, 2H), 7.67–7.39 (m, 8H), 7.17–6.93 (m, 8H), 2.69–2.12 (m, 45H). The toluene solution (1×10 -5 M) has a FWHM of 30 nm.

[0170] Example 8 Synthesis of Compound 256:

[0171]

[0172] Preparation of intermediate K8:

[0173] The synthesis of intermediate K8 was based on intermediate J1, except that intermediate J7 was used instead of raw material A1, and raw material C5 was used instead of raw material B1 to obtain intermediate K8. LC-MS: Measured value: 913.48 ([M+H] + ), exact mass: 912.51.

[0174] Preparation of compound 256:

[0175] The synthesis of compound 256 was based on compound 51, except that intermediate K8 was used instead of intermediate K1 to obtain the target compound 256. LC-MS: Measured value: 921.56 ([M+H] + ), exact mass: 920.49. 1 H NMR (400MHz, Chloroform-d) δ8.21 (m, 1H), 7.99–7.84 (m, 1H), 7.80 (dd, 1H), 7.69–7.42 (m, 7H), 7.35 (d, 1H), 7.27–6.90 (m, 9H), 2.78–1.95 (m, 45H). The toluene solution (1×10 -5 M) has a FWHM of 32 nm.

[0176] The structural characteristics of the compounds obtained in each example are shown in Table 1

[0177] Table 1

[0178]

[0179] The compounds of the present invention can be used as doping materials for the light-emitting layer in light-emitting devices. Fluorescence quantum yields of the compounds prepared in the above examples of the present invention were tested, and the fluorescence quantum yields of Compounds 51, 92, 107, 145, 177, 244, 252, and 256 were as high as 91.6% to 96.2%.

[0180] PLQY (fluorescence quantum yield) and FWHM (full width at half maximum) were measured by Horiba's Fluorolog-3 series fluorescence spectrometer.

[0181] The compound of the present invention has a high fluorescence quantum efficiency as a doping material, and the fluorescence quantum efficiency of the material is close to 100%. At the same time, the spectral FWHM of the material is narrow, which can effectively improve the color gamut of the device and improve the luminous efficiency of the device.

[0182] Device Examples

[0183] The following describes in detail the application effects of the OLED materials synthesized by the present invention in devices using device Examples 1-8 and Comparative Examples 1-4. The device fabrication processes for Device Examples 2-8 and Comparative Examples 1-4 are identical to those of Device Example 1, utilizing the same substrate and electrode materials, with the same electrode thickness. The only difference is the material used in the light-emitting layer. The layer structures and test results for each device example are shown in Tables 3 and 4, respectively.

[0184] Device Example 1

[0185] like Figure 1 As shown, the transparent substrate layer 1 is a transparent PI film, and the ITO anode layer 2 (film thickness of 150nm) is washed, that is, washed with a detergent (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 and 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 evaporation is completed, the light-emitting layer 6 of the OLED light-emitting device is prepared, using GH-1 and GH-2 as the main materials, compound 51 as the doping material, the mass ratio of GH-1, GH-2 and compound 51 is 69:30:1, and the light-emitting layer thickness is 30nm. After the light-emitting layer 6, HB-1 was vacuum-deposited to a thickness of 5 nm. This layer served as the hole-blocking layer 7. After the hole-blocking layer 7, ET-1 and Liq were vacuum-deposited in a 1:1 weight ratio to form a 30 nm thick film. This served as the electron-transporting layer 8. On the electron-transporting layer 8, a 1 nm thick LiF layer was vacuum-deposited. This served as the electron-injection layer 9. On the electron-injection layer 9, an 80 nm thick Mg:Ag electrode layer was vacuum-deposited in a 1:9 weight ratio. This served as the cathode layer 10.

[0186] The following describes in detail the application effects of the OLED materials synthesized by the present invention in devices using device Examples 9-16 and Comparative Examples 5-8. The device fabrication processes for Device Examples 10-16 and Comparative Examples 5-8 are identical to those of Device Example 9, utilizing the same substrate and electrode materials, with the same electrode thickness. The only difference is the material used in the light-emitting layer. The layer structures and test results for each device example are shown in Tables 3 and 4, respectively.

[0187] Device Example 9

[0188] The transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (film thickness 150nm) is washed, i.e., washed with a detergent (Semiclean M-L20), washed with pure water, dried, and then subjected to UV-ozone cleaning to remove organic residues from the transparent ITO surface. On the washed ITO anode layer 2, a 10nm thick layer of HT-1 and HI-1 is deposited using a vacuum evaporation device as the hole injection layer 3. The mass ratio of HT-1 to HI-1 is 97:3. HT-1 is then evaporated to a thickness of 60nm as the hole transport layer 4. EB-1 is then evaporated to a thickness of 30nm as the electron blocking layer 5. After the electron-blocking material deposition was completed, the light-emitting layer 6 of the OLED light-emitting device was formed. GH-1 and GH-2 were used as the host materials, GD-1 was used as the first dopant material, and Compound 51 was used as the second dopant material. The mass ratio of GH-1, GH-2, GD-1, and Compound 51 was 66:30:3:1, and the light-emitting layer had a thickness of 30 nm. Following the light-emitting layer 6, HB-1 was vacuum-deposited to a thickness of 5 nm. This layer served as the hole-blocking layer 7. Following the hole-blocking layer 7, ET-1 and Liq were vacuum-deposited to a thickness of 30 nm. The electron-transporting layer 8 was formed by vacuum deposition of ET-1 and Liq in a mass ratio of 1:1. A 1 nm thick LiF layer was deposited on the electron-transporting layer 8 using a vacuum deposition apparatus. This layer served as the electron-injection layer 9. An 80 nm thick Mg:Ag electrode layer was deposited on the electron-injection layer 9 using a vacuum deposition apparatus. The mass ratio of Mg:Ag was 1:9. This layer served as the cathode layer 10.

[0189] The molecular structure formula of the relevant materials is shown below:

[0190]

[0191]

[0192] After completing the OLED light-emitting device as described above, the anode and cathode were connected using a known drive circuit, and the device's current efficiency and lifetime were measured. Examples and comparative examples of devices prepared using the same method are shown in Table 3; the test results for the current efficiency and lifetime of the resulting devices are shown in Table 4.

[0193] Table 3

[0194]

[0195]

[0196] Table 4

[0197]

[0198] Note: Voltage, current efficiency, and luminescence peak were measured using an IVL (current-voltage-luminance) test system (Suzhou Fushida Scientific Instrument Co., Ltd.); the lifespan test system was an EAS-62C OLED device lifespan tester from Japan System Giken Co., Ltd.; LT95 refers to the time it takes for the device's luminance to decay to 95%; all data are measured at 10 mA / cm 2 Next test.

[0199] It can be seen from the device data results in Table 4 that, compared with device comparison examples 1-8, the organic light-emitting devices of the present invention, whether in a single-doping system or a dual-doping system, have significantly improved current efficiency and life compared to OLED devices made of known materials; when an exciton-sensitizing material is used as the first dopant, the device life is significantly improved compared to that of a single-doping system.

[0200] In summary, the above are only preferred embodiments of the present invention and are not intended to limit the present invention. Any modifications, equivalent replacements, improvements, etc. made within the spirit and principles of the present invention should be included in the scope of protection 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), the M1 ring represents the structure shown in the general formula (1-1); "*" indicates the site of connection; Said X3 is represented by O, S; The M2 ring is represented by a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted benzofuran ring, or a substituted or unsubstituted benzothiophene ring; Z is represented by C-R1; each occurrence of R1 is the same or different and represents H, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl or silyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups; X1 and X2 represent O, S, N(R2), and R2 represents a substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups; The substituents for the substituent group are optionally selected from halogen atoms, deuterium atoms, cyano groups, C1-C 10 Alkyl, C5-C 10 Cycloalkyl, C5-C 10 Cycloalkenyl, C1-C 10 Alkoxy, C3-C 20 Cycloalkyl, C6-C 30 Aryl, C3-C 30 one or more of heteroaryl groups; The heteroatoms in the heteroaryl group are selected from one or more of O, S, N, and Si.

2. The resonance type organic compound according to claim 1, characterized in that The M1 and M2 rings represent the structure shown in the general formula (1-1); "*" indicates the site of connection; Z is represented by C-R1; each occurrence of R1 is the same or different and represents H, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl or silyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups; Said X3 is represented by O, S; The substituents for the substituent group are optionally selected from halogen atoms, deuterium atoms, cyano groups, C1-C 10 Alkyl, C5-C 10 Cycloalkyl, C5-C 10 Cycloalkenyl, C1-C 10 Alkoxy, C3-C 20 Cycloalkyl, C6-C 30 Aryl, C3-C 30 one or more of heteroaryl groups; The heteroatoms in the heteroaryl group are selected from one or more of O, S, N, and Si.

3. A resonance type organic compound, characterized in that The structure of the resonance-type organic compound is shown in any one of general formulas (2) to (6): In general formula (2) to general formula (6), 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 or silyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups; X1 and X2 represent O, S, N(R2), and R2 represents a substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups; Said X3 is represented by O, S; Said X4 is represented by O, S; The substituents for the substituent group are optionally selected from halogen atoms, deuterium atoms, cyano groups, C1-C 10 Alkyl, C5-C 10 Cycloalkyl, C5-C 10 Cycloalkenyl, C1-C 10 Alkoxy, C3-C 20 Cycloalkyl, C6-C 30 Aryl, C3-C 30 one or more of heteroaryl groups; The heteroatoms in the heteroaryl group are selected from one or more of O, S, N, and Si.

4. A resonance type organic compound, characterized in that The structure of the resonance-type organic compound is shown in any one of general formulas (7) to (13): In general formulas (7) to (13), 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 or silyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups; Said X3 is represented by O, S; Said X4 is represented by O, S; The substituents for the substituent group are optionally selected from halogen atoms, deuterium atoms, cyano groups, C1-C 10 Alkyl, C5-C 10 Cycloalkyl, C5-C 10 Cycloalkenyl, C1-C 10 Alkoxy, C3-C 20 Cycloalkyl, C6-C 30 Aryl, C3-C 30 one or more of heteroaryl groups; The heteroatoms in the heteroaryl group are selected from one or more of O, S, N, and Si.

5. A resonance type organic compound, characterized in that The structure of the resonance-type organic compound is shown in any one of general formulas (14) to (21): In general formulas (14) to (21), 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 or silyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups; Said X3 is represented by O, S; Said X4 is represented by O, S; The R a 、R b 、R c 、R d 、R e Represented by H, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C 10 Alkyl or silyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups; The substituents for the substituent group are optionally selected from halogen atoms, deuterium atoms, cyano groups, C1-C 10 Alkyl, C5-C 10 Cycloalkyl, C5-C 10 Cycloalkenyl, C1-C 10 Alkoxy, C3-C 20 Cycloalkyl, C6-C 30 Aryl, C3-C 30 one or more of heteroaryl groups; The heteroatoms in the heteroaryl group are selected from one or more of O, S, N, and Si.

6. The resonance type organic compound according to claim 1, characterized in that R1 is hydrogen, deuterium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopentyl, 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 phenanthrenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinoline substituted or unsubstituted furyl, substituted or unsubstituted thienyl, 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 amino, substituted or unsubstituted triazinyl, substituted or unsubstituted adamantyl; R2 is a substituted or unsubstituted cyclohexyl 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 furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted triazinyl group, or a substituted or unsubstituted adamantyl group; The M1 ring is a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring; The M2 ring is represented by one of a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted benzofuran ring, and a substituted or unsubstituted benzothiophene ring; The substituents for the substituent group are 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 phenanthrenyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a quinolyl group, an isoquinolyl group, a furyl 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 azaphenanthrenyl group.

7. The resonance type organic compound according to claim 2, characterized in that R1 is hydrogen, deuterium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopentyl, 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 phenanthrenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinoline substituted or unsubstituted furyl, substituted or unsubstituted thienyl, 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 amino, substituted or unsubstituted triazinyl, substituted or unsubstituted adamantyl; R2 is a substituted or unsubstituted cyclohexyl 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 furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted triazinyl group, or a substituted or unsubstituted adamantyl group; The M1 ring is a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring; The M2 ring is a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring; The substituents for the substituent group are 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 phenanthrenyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a quinolyl group, an isoquinolyl group, a furyl 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 azaphenanthrenyl group.

8. The resonance type organic compound according to claim 3, characterized in that R1 is hydrogen, deuterium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopentyl, 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 phenanthrenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinoline substituted or unsubstituted furyl, substituted or unsubstituted thienyl, 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 amino, substituted or unsubstituted triazinyl, substituted or unsubstituted adamantyl; R2 is a substituted or unsubstituted cyclohexyl 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 furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted triazinyl group, or a substituted or unsubstituted adamantyl group; The substituents for the substituent group are 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 phenanthrenyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a quinolyl group, an isoquinolyl group, a furyl 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 azaphenanthrenyl group.

9. The resonance type organic compound according to claim 4, characterized in that R1 is hydrogen, deuterium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopentyl, 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 phenanthrenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinoline substituted or unsubstituted furyl, substituted or unsubstituted thienyl, 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 amino, substituted or unsubstituted triazinyl, substituted or unsubstituted adamantyl; The substituents for the substituent group are 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 phenanthrenyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a quinolyl group, an isoquinolyl group, a furyl 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 azaphenanthrenyl group.

10. The resonance type organic compound according to claim 5, characterized in that R1 is hydrogen, deuterium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopentyl, 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 phenanthrenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinoline substituted or unsubstituted furyl, substituted or unsubstituted thienyl, 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 amino, substituted or unsubstituted triazinyl, substituted or unsubstituted adamantyl; The R a 、R b 、R c 、R d 、R e represented by hydrogen, deuterium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopentyl, 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 phenanthrenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, One of a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted triazinyl group, and a substituted or unsubstituted adamantyl group; The substituents for the substituent group are 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 phenanthrenyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a quinolyl group, an isoquinolyl group, a furyl 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 azaphenanthrenyl group.

11. 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:

12. 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 11.

13. The organic light-emitting device according to claim 12, characterized in that: The functional layer comprises a light-emitting layer, and the light-emitting layer comprises a host material and a doping material, wherein the doping material is the resonance-type organic compound according to any one of claims 1 to 11.

14. The organic light-emitting device according to claim 13, characterized in that: The light-emitting layer comprises a first host material, a second host material and a doping material, at least one of the first host material and the second host material is a TADF material, and the doping material is the resonance-type organic compound according to any one of claims 1 to 11.

15. The organic light-emitting device according to claim 13, 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 11.

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