Resonant organic compound and use thereof

Abstract

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

Description

[0001] This application is a divisional application of prior application number 202211452811.6, filed on November 21, 2022, entitled "A Resonance Organic Compound and Its Application". Technical Field

[0002] This invention relates to the field of semiconductor technology, and more particularly to a resonant organic compound and its applications. Background Technology

[0003] Traditional fluorescent doped materials, limited by early technologies, can only emit light using 25% of singlet excitons generated by electrical excitation. This results in low internal quantum efficiency (maximum 25%) and external quantum efficiency generally below 5%, significantly lower than that of phosphorescent devices. Phosphorescent materials, due to the strong spin-orbit coupling at the heavy atom centers, enhance intersystem crossing and can effectively utilize both singlet and triplet excitons generated by electrical excitation for emission, achieving an internal quantum efficiency of 100%.

[0004] With the advent of the 5G era, higher requirements have been placed on color rendering standards. In addition to high efficiency and stability, luminescent materials also need narrower half-widths (HWHMs) to improve the purity of the emitted color in devices. Fluorescent dopants can achieve high fluorescence quantum density and narrow HWHM through molecular engineering. Significant breakthroughs have been achieved in blue fluorescent dopants, with the HWHM of boron-based materials reduced to below 30 nm. However, research on the green light region, which is more sensitive to the human eye, has mainly focused on phosphorescent dopants. However, the peak shape of these dopants is difficult to narrow using simple methods. Therefore, researching efficient green fluorescent dopants with narrow HWHMs is of great significance in meeting higher color rendering standards.

[0005] In addition, sensitization technology combines triplet exciton sensitizing materials with fluorescent doping materials. By using triplet exciton sensitizing materials as exciton sensitization media, it makes full use of triplet excitons and transfers energy to fluorescent doping materials through energy transfer, achieving 100% in-device quantum efficiency. This technology can make up for the shortcomings of insufficient exciton utilization in fluorescent doping materials and effectively leverage the high fluorescence quantum yield, high device stability, high color purity, and low cost of fluorescent doping materials, showing broad prospects in OLED applications.

[0006] Boron compounds with resonant structures are more likely to achieve narrow half-width emission (HWHM). When applied to sensitized fluorescence technology, these materials can enable the fabrication of devices with high efficiency and narrow HWHM emission. For example, CN 107507921 A and CN 110492006 A disclose a light-emitting layer combination technology using TADF materials with a minimum singlet and triplet energy level difference of less than or equal to 0.2 eV as the main body and boron-containing materials as dopants; CN 110492005 A and CN 110492009 A disclose a light-emitting layer combination scheme using exciton complexes as the main body and boron-containing materials as dopants; both achieve efficiencies comparable to phosphorescence and relatively narrow HWHM. Therefore, developing sensitization technology based on narrow HWHM boron-based light-emitting materials has unique advantages and strong potential for achieving BT.2020 display performance. Summary of the Invention

[0007] To address the aforementioned problems in the existing technology, the applicant of this invention provides a resonance-type organic compound and its applications.

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

[0009]

[0010] In general formula (1), Z is represented as C-R1;

[0011] Y can be independently represented as C-R2R3 and N-R4, with at least one Y represented as N-R4;

[0012] The recurrence of R1, R2, R3, and R4, whether identical or different, represents H, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C atom. 10 Alkyl, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Silyl, substituted or unsubstituted aromatic amino, 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;

[0013] M1 and M2 represent substituted or unsubstituted C6-C. 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl groups;

[0014] Ar1 represents C1-C with or without substitution. 10 Alkyl, substituted or unsubstituted C2-C 10alkenyl, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 The heteroaryl group; Ar1 ​​and M1 can be linked to form a ring;

[0015] The substituents used for the substituent groups are optionally selected from halogen atoms, deuterium atoms, cyano groups, C1-C... 10 Alkyl, C5-C 10 cycloalkyl, C5-C 10 Cycloalkenyl, C1-C 10 alkoxy groups, C3-C 20 cycloalkyl, C6-C 30 Aryl, C3-C 30 heteroaryl, C2-C 30 One or more of the aromatic amino groups;

[0016] The heteroatom in the heteroaryl group is selected from one of O, S, N, and Si.

[0017] The structure of the preferred resonance-type organic compound is shown in general formula (1-A):

[0018]

[0019] In the general formula (1-A), Z is represented as C-R1;

[0020] Y is independently represented as C-R2R3 and N-R4;

[0021] The recurrence of R1, R2, and R3, whether identical or different, represents H, deuterium atom, halogen atom, cyano group, or substituted or unsubstituted C1-C atom. 10 Alkyl, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Silyl, substituted or unsubstituted aromatic amino, 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;

[0022] R4 represents 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;

[0023] M1 and M2 represent substituted or unsubstituted C6-C. 30aryl, substituted or unsubstituted C3-C 30 heteroaryl groups;

[0024] Ar1 represents C1-C with or without substitution. 10 Alkyl, substituted or unsubstituted C2-C 10 alkenyl, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 The heteroaryl group; Ar1 ​​and M1 can be linked to form a ring;

[0025] The substituents used for the substituent groups are optionally selected from halogen atoms, deuterium atoms, cyano groups, C1-C... 10 Alkyl, C5-C 10 cycloalkyl, C5-C 10 Cycloalkenyl, C1-C 10 alkoxy groups, C3-C 20 cycloalkyl, C6-C 30 Aryl, C3-C 30 heteroaryl, C2-C 30 One or more of the aromatic amino groups;

[0026] The heteroatom in the heteroaryl group is selected from one of O, S, N, and Si.

[0027] Preferably, the structure of the resonance-type organic compound is shown in any one of general formulas (1-1) to (1-4):

[0028]

[0029]

[0030] In general formulas (1-1) to (1-4), the definitions of Z, M1, M2, and Ar1 are the same as those in the above content;

[0031] Z1, Z2, Z3, Z4, Z5, Z6, and Z7 are independently represented as CH or C-R5; each occurrence of R5, whether the same or different, represents a deuterium atom, a halogen atom, a cyano group, or a C1-C group. 10 Alkyl, C2-C 30 Aromatic amino group, C6-C 30 aryl, C3-C 30 One of the heteroaryl groups;

[0032] Ar2 represents C1-C with or without substitution. 10 Alkyl, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C 30 heteroaryl groups;

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

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

[0035] Preferably, the structure of the resonance-type organic compound is shown in any one of general formulas (1-5) to (1-14):

[0036]

[0037]

[0038] In general formulas (1-5) to (1-14), the definitions of Z and Ar1 are the same as those in the above content;

[0039] Z1, Z2, Z3, Z4, Z5, Z6, and Z7 are independently represented as CH or C-R5; each occurrence of R5, whether the same or different, represents a deuterium atom, a halogen atom, a cyano group, or a C1-C group. 10 Alkyl, C2-C 30 Aromatic amino group, C6-C 30 aryl, C3-C 30 One of the heteroaryl groups;

[0040] Ar2 and Ar3 are independently represented as substituted or unsubstituted C1-C, respectively. 10 Alkyl, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl groups;

[0041] The substituents used for the substituent groups are optionally selected from halogen atoms, deuterium atoms, cyano groups, C1-C... 10 Alkyl, C5-C 10 cycloalkyl, C5-C 10 Cycloalkenyl, C1-C 10 alkoxy groups, C3-C 20cycloalkyl, C6-C 30 Aryl, C3-C 30 One or more of the heteroaryl groups;

[0042] The heteroatom in the heteroaryl group is selected from one of O, S, N, and Si.

[0043] Preferably, the structure of the resonance-type organic compound is shown in any one of general formulas (2-1) to (2-10):

[0044]

[0045]

[0046] In general formulas (2-1) to (2-10), the definitions of Z, M1 and Ar1 are the same as those in the above content;

[0047] Ar2 represents C1-C with or without substitution. 10 Alkyl, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl groups;

[0048] The substituents used for the substituent groups are optionally selected from halogen atoms, deuterium atoms, cyano groups, C1-C... 10 Alkyl, C5-C 10 cycloalkyl, C5-C 10 Cycloalkenyl, C1-C 10 alkoxy groups, C3-C 20 cycloalkyl, C6-C 30 Aryl, C3-C 30 One or more of the heteroaryl groups;

[0049] The heteroatom in the heteroaryl group is selected from one of O, S, N, and Si.

[0050] Preferably, M1 is represented as any of the following ring structures:

[0051]

[0052] M2 can be represented by any of the following ring structures:

[0053]

[0054]

[0055] The definition of Z in the above formula is the same as the limitation mentioned above.

[0056] Preferably, the organic compound has the structure shown in general formulas (3-1) to (3-12):

[0057]

[0058]

[0059] In general formulas (3-1) to (3-12), the definition of Z is the same as the limitation in the above content;

[0060] Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8, Z9, Z 10 Z 11 Z 12 Individually represented as CH or C-R5; each occurrence of R5, whether the same or different, indicates a deuterium atom, halogen atom, cyano group, or C1-C. 10 Alkyl, C2-C 30 Aromatic amino group, C6-C 30 aryl, C3-C 30 It is one of the heteroaryl groups.

[0061] Preferably, the structure of the organic compound is shown in any one of general formulas (4-1) to (4-7):

[0062]

[0063] In general formulas (4-1) to (4-7), the definition of Z is the same as the limitation in the above content;

[0064] Z1, Z2, Z3, Z4, Z5, and Z6 are independently represented as CH or C-R5; each occurrence of R5, whether the same or different, represents a deuterium atom, a halogen atom, a cyano group, or a C1-C group. 10 Alkyl, C2-C 30 Aromatic amino group, C6-C 30 aryl, C3-C 30 One of the heteroaryl groups;

[0065] Ar2 and Ar3 are independently represented as substituted or unsubstituted C1-C, respectively. 10 Alkyl, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl groups;

[0066] Ra and Rb are independently represented as hydrogen atoms, substituted or unsubstituted C1-C atoms, respectively. 10 Alkyl, substituted or unsubstituted C3-C 10cycloalkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl groups;

[0067] The substituents used for the substituent groups are optionally selected from halogen atoms, deuterium atoms, cyano groups, C1-C... 10 Alkyl, C5-C 10 cycloalkyl, C5-C 10 Cycloalkenyl, C1-C 10 alkoxy groups, C3-C 20 cycloalkyl, C6-C 30 Aryl, C3-C 30 One or more of the heteroaryl groups;

[0068] The heteroatom in the heteroaryl group is selected from one of O, S, N, and Si.

[0069] Preferably, R1 to R5 appearing in the same or different forms are represented by hydrogen, deuterium atom, halogen atom, cyano group, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted isopropyl group, substituted or unsubstituted tert-butyl group, substituted or unsubstituted cyclohexyl group, substituted or unsubstituted adamantyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted diphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthracene group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted pyridyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted furfural group. alkyl, substituted or unsubstituted thiophene, substituted or unsubstituted benzofuran, substituted or unsubstituted benzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, 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 triazine, substituted or unsubstituted 4a,9a-dimethyl-9-phenyl-1,2,3,4-tetrahydrocarbazole;

[0070] Ar1, Ar2, and Ar3 are independently represented as substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted vinyl, substituted or unsubstituted propenyl, substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthryl, and substituted or unsubstituted pyridine, respectively. alkyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiophene, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amino;

[0071] M1 and M2 represent one of the following: substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiophenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted indole[3,2,1-jk]carbazolyl, and substituted or unsubstituted 4a,9a-dimethyl-9-phenyl-1,2,3,4-tetrahydrocarbazolyl.

[0072] The R a R bRepresented as hydrogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiopheneyl, etc. Substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amino, substituted or unsubstituted triazine, substituted or unsubstituted 4a,9a-dimethyl-9-phenyl-1,2,3,4-tetrahydrocarbazole;

[0073] The substituents used for the substituent groups are selected from one or more of the following: deuterium atom, chlorine atom, fluorine atom, trifluoromethyl, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthrene, pyridinyl, pyrazinyl, pyrazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheneyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheninyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazoleyl, N-phenylcarbazoleyl, carbazolinyl, and aziphenanthreneyl.

[0074] In a preferred embodiment, R1, R2, R3, R4, and R5 are represented by the following structure:

[0075] hydrogen atom,

[0076] Any one of them;

[0077] The Ar1, Ar2, Ar3, and R a R b It can be represented as the structure shown below:

[0078]

[0079] Any one of them.

[0080] Preferably, the specific structural formula of the resonance-type organic compound is any one of the following structures:

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096] An organic light-emitting device includes a cathode, an anode, and a functional layer, wherein the functional layer is located between the cathode and the anode, and the functional layer of the organic light-emitting device contains the resonant organic compound.

[0097] Preferably, the functional layer includes a light-emitting layer, which comprises a host material and a dopant material, wherein the dopant material is the resonant organic compound.

[0098] In a preferred embodiment, the light-emitting layer comprises a first host material, a second host material, and a dopant material, wherein at least one of the first host material and the second host material is a TADF material, and the dopant material is the resonant organic compound.

[0099] In a preferred embodiment, the light-emitting layer comprises a host material, an exciton-sensitizing material, and a dopant material, wherein the exciton-sensitizing material is a complex containing a metal element, and the dopant material is the resonant organic compound.

[0100] Compared with the prior art, the beneficial technical effects of the present invention are as follows:

[0101] (1) The compound of the present invention can be used as a dopant material for OLED devices, and can emit fluorescence under the action of an electric field. It can be applied to OLED lighting or OLED display fields.

[0102] (2) The compound of the present invention is used as a doping material, and phosphorescent material is introduced as an exciton sensitizer, which can effectively improve the device lifetime;

[0103] (3) The compounds of the present invention have a narrower FWHM spectrum, which can effectively improve the color gamut of the device and improve the luminous efficiency of the device;

[0104] The compounds of this invention have narrow half-widths and can be used as doping materials for the light-emitting layer of organic electroluminescent devices, thereby improving the purity of the emitted color and the lifetime of the device. Attached Figure Description

[0105] Figure 1 This is a schematic diagram of the structure of an OLED device in which the materials listed in this invention are applied;

[0106] Wherein, 1 is a transparent substrate layer, 2 is an anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light-emitting layer, 7 is a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, and 10 is a cathode layer. Detailed Implementation

[0107] The present invention will now be described in detail with reference to the accompanying drawings and embodiments.

[0108] In this invention, the terms "upper," "lower," "top," and "bottom," used to describe electrodes, organic electroluminescent devices, and other structures, indicate orientation only in a specific state and do not imply that the structure can only exist in that orientation. Conversely, if the structure can be repositioned, such as by inverting it, the orientation of the structure changes accordingly. Specifically, in this invention, the "bottom" or "lower" side of the electrode refers to the side of the electrode closer to the substrate during fabrication, while the opposite side farther from the substrate is the "top" or "upper" side.

[0109] In this invention, C6-C is substituted or unsubstituted. 30 Aryl groups refer to substituted or unsubstituted phenyl groups, substituted or unsubstituted naphthyl groups, substituted or unsubstituted anthraquinyl groups, substituted or unsubstituted fluorenyl groups, substituted or unsubstituted dimethylfluorenyl groups, substituted or unsubstituted diphenylfluorenyl groups, substituted or unsubstituted spirofluorenyl groups, substituted or unsubstituted phenanthrene groups, substituted or unsubstituted tetraphenyl groups, substituted or unsubstituted pyrene groups, substituted or unsubstituted biphenyl groups, substituted or unsubstituted para-triphenyl groups, substituted or unsubstituted meta-triphenyl groups, and substituted or unsubstituted phenyl groups. The compounds may be substituted or unsubstituted triphenyl, substituted or unsubstituted peryl, substituted or unsubstituted indole, but are not limited thereto.

[0110] In this invention, C3-C is substituted or unsubstituted. 30 Heteroaryl refers to substituted or unsubstituted furanyl, substituted or unsubstituted thiophene, substituted or unsubstituted pyrrole, substituted or unsubstituted pyrazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted oxadiazolyl, substituted or unsubstituted thiadiazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted triazine, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophene, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted... The fused ring of substituted indolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted naphridyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridineyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenthiazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted fumonyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoleyl, combinations thereof, or combinations of the foregoing groups, but not limited thereto.

[0111] The C1-C of this invention 10 Alkyl groups (including straight-chain alkyl and branched-chain alkyl) refer to methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, sec-butyl, neopentyl, n-pentyl, isopentyl, octyl, heptyl, n-decyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 1-butylpentyl, etc., but are not limited to these.

[0112] The C3-C of this invention 10 Cycloalkyl refers to a monovalent monocyclic saturated hydrocarbon group comprising 3 to 10 carbon atoms as cyclic atoms. In this document, C4-C9 cycloalkyl groups are preferred, C5-C8 cycloalkyl groups are more preferred, and C5-C7 cycloalkyl groups are particularly preferred. Non-limiting examples may include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl, and cycloheptyl.

[0113] As the substrate for the organic electroluminescent device of this invention, any substrate commonly used in organic electroluminescent devices can be used. Examples include transparent substrates, such as glass or transparent plastic substrates; and opaque substrates, such as silicon substrates. Different substrates have different mechanical strengths, thermal stability, transparency, surface smoothness, and water resistance. Depending on the properties of the substrate, its application direction varies. In this invention, a transparent PI film substrate is preferred. There are no particular limitations on the thickness of the substrate.

[0114] A first electrode is formed on a substrate, and the first electrode and a second electrode may be opposite each other. The first electrode may be an anode. The first electrode may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the first electrode is a transmissive electrode, it may be formed using a transparent metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium tin zinc oxide (ITZO). When the first electrode is a semi-transmissive electrode or a reflective electrode, it may include Ag, Mg, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, or a mixture of metals. The thickness of the first electrode layer depends on the material used, typically 50-500 nm, preferably 70-300 nm, and more preferably 100-200 nm.

[0115] 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.

[0116] In this paper, the hole transport region constituting an organic electroluminescent device can be listed as a hole injection layer, a hole transport layer, an electron blocking layer, etc.

[0117] As for the materials used in the hole injection layer, hole transport layer, and electron blocking layer, any material can be selected from known materials used in OLED devices.

[0118] Examples of the aforementioned materials include phthalocyanine derivatives, triazole derivatives, triarylmethane derivatives, triarylamine derivatives, oxazole derivatives, oxadiazole derivatives, hydrazone derivatives, stilbene derivatives, pyridinium derivatives, polysilane derivatives, imidazole derivatives, phenylenediamine derivatives, amino-substituted quinone derivatives, styrene-based anthracene derivatives, styrene-based amine derivatives, styrene compounds, fluorene derivatives, spirofluorene derivatives, silazane derivatives, aniline copolymers, porphyrin compounds, carbazole derivatives, polyaryl alkane derivatives, polyphenylene oxide and its derivatives, polythiophene and its derivatives, poly-N-vinylcarbazole derivatives, thiophene oligomers and other conductive polymers, aromatic tertiary amine compounds, and styrene aminations. Compounds, triamines, tetraamines, benzidines, propyne diamine derivatives, p-phenylenediamine derivatives, m-phenylenediamine derivatives, 1,1'-bis(4-diarylaminophenyl)cyclohexane, 4,4'-bis(diarylamine)biphenyls, bis[4-(diarylamino)phenyl]methanes, 4,4'-bis(diarylamino)terphenyls, 4,4'-bis(diarylamino)tetraphenyls, 4,4'-bis(diarylamino)diphenyl ethers, 4,4'-bis(diarylamino)diphenylsulfanes, bis[4-(diarylamino)phenyl]dimethylmethanes, bis[4-(diarylamino)phenyl]-bis(trifluoromethyl)methanes, or 2,2-diphenylethylene compounds, etc.

[0119] Furthermore, depending on the device configuration requirements, the hole transport film layer between the electron blocking and hole injection layers of an organic electroluminescent device can be a single film layer or a stacked structure of multiple hole transport materials. In this paper, the film thickness of the various hole carrier conduction films with different functions is not particularly limited.

[0120] The hole injection layer comprises a host organic material capable of conducting holes, and a p-type doped material with a deep HOMO level (correspondingly, a deep LUMO level). Based on empirical observations, to achieve smooth hole injection from the anode to the organic film, the HOMO level of the host organic material used in the anode interface buffer layer must possess certain characteristics with the p-doped material. This is necessary to enable charge transfer states between the host and doped materials, achieve ohmic contact between the buffer layer and the anode, and realize efficient hole injection conduction from the electrode to the hole injection layer.

[0121] Based on the above empirical summary, different P-doped materials need to be selected to match the hole-based host materials of different HOMO energy levels in order to achieve ohmic contact at the interface and improve the hole injection effect.

[0122] Therefore, in one embodiment of the present invention, in order to improve hole injection, the hole injection layer further comprises a p-type dopant material selected from the following charge-conducting materials: quinone derivatives, such as tetracyanoquinone dimethyl (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethyl (F4-TCNQ); or hexaazatriphenyl derivatives, such as 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenyl (HAT-CN); or cyclopropane derivatives, such as 4,4',4”-((1E,1'E,1”E)-cyclopropane-1,2,3-trimethylenetris(cyanoformyl))tris(2,3,5,6-tetrafluorobenzyl); or metal oxides, such as tungsten oxide and molybdenum oxide, but not limited thereto.

[0123] In the hole injection layer of the present invention, the ratio of hole transport material to P-type doped material is 99:1-95:5, preferably 99:1-97:3, based on mass meter.

[0124] The thickness of the hole injection layer of the present invention can be 5-100 nm, preferably 5-50 nm, and more preferably 5-20 nm, but the thickness is not limited to this range.

[0125] The thickness of the hole transport layer of the present invention can be 5-200 nm, preferably 10-150 nm, and more preferably 20-100 nm, but the thickness is not limited to this range.

[0126] The thickness of the electron blocking layer of the present invention can be 1-50 nm, preferably 5-40 nm, but the thickness is not limited to this range.

[0127] After forming the hole injection layer, hole transport layer, and electron blocking layer, a corresponding light-emitting layer is formed on top of the electron blocking layer.

[0128] The light-emitting layer may include a host material and a dopant material. The host material may be a green light host material commonly used in the art, and the dopant material may be a resonant organic compound represented by the general formula (1) of this invention.

[0129] The light-emitting layer can contain a single-substrate material or a dual-substrate material;

[0130] The dual-body material comprises a first body material and a second body material, wherein preferably at least one of the first body material and the second body material is a TADF material;

[0131] TADF materials refer to materials with thermally activated delayed fluorescence properties. They are characterized by a small energy difference between the first excited singlet and triplet states, allowing for the simultaneous utilization of both singlet and triplet excitons generated within the device, thus enabling the exciton utilization rate of electrogenerated excitons within the device to approach 100%. Compared to traditional fluorescent materials, TADF materials exhibit higher exciton utilization.

[0132] The light-emitting layer may include a host material, an exciton-sensitizing material, and a dopant material;

[0133] Exciton-sensitized materials refer to materials that enable the luminescent material in the luminescent layer to fully utilize electroexcitons, thereby allowing the luminescent layer to ultimately produce the emission spectrum of the sensitized material. Exciton sensitizers may perform functions such as exciton capture, exciton conversion, and exciton transfer in electroluminescent devices. The resonant organic compound shown in general formula (1) of this invention, when used in combination with exciton-sensitized materials, has a significant effect on improving device efficiency, exciton annihilation in the device, and efficiency reduction.

[0134] In the light-emitting layer of the present invention, the ratio of the host material to the dopant material is 99:1-70:30, preferably 99:1-85:15 and more preferably 97:3-87:13, based on mass.

[0135] The thickness of the light-emitting layer can be adjusted to optimize luminous efficiency and driving voltage. The preferred thickness range is 5 nm to 50 nm, more preferably 10-50 nm, and even more preferably 15-40 nm, but the thickness is not limited to this range.

[0136] In this invention, the electron transport region may include, from bottom to top, a hole blocking layer, an electron transport layer, and an electron injection layer disposed on the light-emitting layer, but is not limited thereto.

[0137] A hole-blocking layer is a layer that prevents holes injected from the anode from passing through the light-emitting layer and entering the cathode, thereby extending the device's lifetime and improving its efficiency. The hole-blocking layer of this invention can be disposed above the light-emitting layer. As the hole-blocking layer material for the organic electroluminescent device of this invention, compounds with hole-blocking properties known in the prior art can be used, such as phenanthroline derivatives like copper hydroxide (BCP), metal complexes of hydroxyquinoline derivatives like aluminum(III)bis(2-methyl-8-quinoline)-4-phenylphenol (BAlq), various rare earth complexes, oxazole derivatives, triazole derivatives, triazine derivatives, pyrimidine derivatives like 9,9'-(5-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-1,3-phenylene)bis(9H-carbazole), etc. The thickness of the hole-blocking layer of this invention can be 2-200 nm, preferably 5-150 nm, but the thickness is not limited to this range.

[0138] An electron transport layer may be disposed above the light-emitting layer or (if present) a hole-blocking layer. The electron transport layer material is one that readily receives electrons from the cathode and transfers the received electrons to the light-emitting layer. A material with high electron mobility is preferred. As the electron transport layer of the organic electroluminescent device of the present invention, electron transport layer materials known in the prior art for organic electroluminescent devices can be used, such as metal complexes of hydroxyquinoline derivatives represented by Alq3, BAlq and Liq, various rare earth metal complexes, triazole derivatives, triazine derivatives such as 2,4-bis(9,9-dimethyl-9H-fluoren-2-yl)-6-(naphthyl-2-yl)-1,3,5-triazine (CAS No.: 1459162-51-6), imidazole derivatives such as 2-(4-(9,10-bis(naphthyl-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole (CAS No.: 561064-11-7, commonly known as LG201), oxadiazole derivatives, thiadiazole derivatives, carbodiimide derivatives, quinoxaline derivatives, phenanthroline derivatives, silicon-based compound derivatives, etc. The thickness of the electron transport layer of the present invention can be 10-80 nm, preferably 20-60 nm and more preferably 25-45 nm, but the thickness is not limited to this range.

[0139] An electron injection layer may be disposed above the electron transport layer. The electron injection layer material is typically preferably a material with a low work function, allowing electrons to be easily injected into the organic functional material layer. As the electron injection layer material for the organic electroluminescent device of the present invention, electron injection layer materials known in the art for organic electroluminescent devices can be used, such as lithium; lithium salts, such as lithium 8-hydroxyquinoline, lithium fluoride, lithium carbonate, or lithium azide; or cesium salts, such as cesium fluoride, cesium carbonate, or cesium azide. The thickness of the electron injection layer of the present invention may be 0.1-5 nm, preferably 0.5-3 nm, and more preferably 0.8-1.5 nm, but the thickness is not limited to this range.

[0140] The second electrode may be disposed above the electron transport region. The second electrode may be a cathode. The second electrode may be a transmission electrode, a semi-transmission electrode, or a reflection electrode. When the second electrode is a transmission electrode, it may include, for example, Li, Yb, Ca, LiF / Ca, LiF / Al, Al, Mg, Ba, Ag, or compounds or mixtures thereof; when the second electrode is a semi-transmission electrode or a reflection electrode, it may include Ag, Mg, Yb, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, or compounds or mixtures thereof, but is not limited thereto. The thickness of the cathode depends on the material used.

[0141] The organic electroluminescent device of the present invention may further include an encapsulation structure. The encapsulation structure may be a protective structure preventing external substances such as moisture and oxygen from entering the organic layer of the organic electroluminescent device. The encapsulation structure may be, for example, a can, such as a glass or metal can; or a thin film covering the entire surface of the organic layer.

[0142] The method for preparing the organic electroluminescent device of the present invention includes sequentially laminating an anode, a hole injection layer, a hole transport layer, an electron blocking layer, an organic film layer, an electron transport layer, an electron injection layer, and a cathode, and optionally a capping layer, onto a substrate. In this regard, methods such as vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing, or LITI can be used, but are not limited thereto. In the present invention, vacuum evaporation is preferably used to form the various layers. Those skilled in the art can conventionally select the various process conditions in the vacuum evaporation method according to actual needs.

[0143] Synthesis Examples

[0144] All raw materials involved in the synthesis embodiments of this invention can be purchased from the market or obtained by conventional preparation methods in the art.

[0145] I. Synthesis of intermediate J

[0146] 1. Synthesis of intermediate J1:

[0147]

[0148] 184.9 mmol of starting material M1 was dissolved in 150 mL of dioxane, and then 203.3 mmol of starting material M2 was added. 20 mL of concentrated sulfuric acid was added dropwise to the reaction solution under ice bath conditions, and the reaction solution was then stirred at 110 °C for 3 hours. After the reaction was complete, the reaction solution was cooled to room temperature and filtered. The residue was dissolved in 200 mL of water, the pH was adjusted to alkaline with sodium hydroxide solution, and then extracted with 200 mL of dichloromethane. The residue was then washed successively with water, saturated brine, dried over anhydrous sodium sulfate, and concentrated to obtain intermediate Y1. LC-MS: Measured value: 273.12 ([M+H) + Theoretical value: 272.15.

[0149] 87.8 mmol of intermediate Y1 was dissolved in 250 mL of tetrahydrofuran, and 395.1 mmol of sodium hydroxide was added under ice bath conditions. After reacting for 1 hour, 92.1 mmol of p-toluenesulfonyl chloride was added in portions to the reaction solution, and the reaction solution was stirred at 25 °C for 15 hours. After the reaction was completed, the reaction solution was diluted with 200 mL of ethyl acetate, then washed successively with water, saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate = 20 / 1) to give intermediate Y2. LC-MS: Measured value: 427.22 ([M+H) +Theoretical value: 426.16.

[0150] 81.7 mmol of intermediate Y2 was dissolved in 350 mL of dioxane, followed by the addition of 350 mL of dioxane in 4N hydrochloric acid. The reaction mixture was stirred at room temperature for 16 hours. After the reaction was complete, the pH was adjusted to alkaline with sodium bicarbonate solution, and the aqueous phase was extracted with ethyl acetate (100 mL × 3). The combined organic phases were washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (dichloromethane / methanol = 20 / 1) to obtain intermediate Y3. LC-MS: Measured value: 327.29 ([M+H) + Theoretical value: 326.11.

[0151] 79.4 mmol of intermediate Y3 was dissolved in 250 mL of toluene, followed by the addition of 95.2 mmol of starting material M12, 7.9 mmol of BINAP, 158.8 mmol of sodium tert-butoxide, and 3.9 mmol of Pd2(dba)3. After purging the air three times with nitrogen, the reaction mixture was stirred at 105 °C for 16 hours. After the reaction was complete, the mixture was diluted with 200 mL of ethyl acetate, then washed successively with water, saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate = 50 / 1) to obtain intermediate Y4. LC-MS: Measured value: 403.08 ([M+H) + Theoretical value: 402.14.

[0152] 33.9 mmol of intermediate Y4 was dissolved in 90 mL of dioxane and 90 mL of methanol, and then 135.6 mmol of sodium tert-butoxide was rapidly added. The reaction mixture was stirred at 90 °C for 16 hours. After the reaction was complete, the reaction mixture was cooled to room temperature and concentrated. The residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate = 20 / 1) to give intermediate J1. LC-MS: Measured value: 249.35 ([M+H) + Theoretical value: 248.13.

[0153] 2. Synthesis of intermediate J2:

[0154]

[0155] 79.4 mmol of intermediate Y3 was dissolved in 250 mL of toluene, followed by the addition of 95.2 mmol of starting material M3, 7.9 mmol of BINAP, 158.8 mmol of sodium tert-butoxide, and 3.9 mmol of Pd2(dba)3. After purging the air three times with nitrogen, the reaction mixture was stirred at 105 °C for 16 hours. After the reaction was complete, the mixture was diluted with 200 mL of ethyl acetate, then washed successively with water, saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate = 50 / 1) to obtain intermediate Y5. LC-MS: Measured value: 515.33 ([M+H) + Theoretical value: 514.27.

[0156] 33.9 mmol of intermediate Y5 was dissolved in 90 mL of dioxane and 90 mL of methanol, and then 135.6 mmol of sodium tert-butoxide was rapidly added. The reaction mixture was stirred at 90 °C for 16 hours. After the reaction was complete, the reaction mixture was cooled to room temperature and concentrated. The residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate = 20 / 1) to give intermediate J2. LC-MS: Measured value: 361.19 ([M+H) + Theoretical value: 360.26.

[0157] 3. Synthesis of intermediate J3:

[0158]

[0159] Under nitrogen protection, 10 mmol of starting material M4, 25 mmol of starting material M5, 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 the reaction was carried out at room temperature for 4 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 a-1. LC-MS: Measured value: 339.24 ([M+H)) + Theoretical value: 338.20.

[0160] 1 mmol of intermediate a-1, 1 mmol of starting material M6, and 10 ml of methanol were added to a sealed, pressure-resistant tube. 300 mg of concentrated sulfuric acid was added dropwise, and the mixture was refluxed and stirred for 8 hours. The reaction solution was cooled to room temperature, diluted with 20 ml of dichloromethane, and separated by column chromatography to obtain intermediate b-1. Intermediate b-1: LC-MS: Measured value: 293.34 ([M+H)) + Theoretical value: 292.19.

[0161] In a sealed, pressure-resistant tube under nitrogen protection, 10 mmol of intermediate b-1 was added to anhydrous o-dichlorobenzene. 22 mmol of methyllithium (n-hexane) solution was added dropwise at -40°C. After stirring for 3 hours, the mixture was allowed to return to room temperature. The reaction solution was concentrated and separated by column chromatography to obtain intermediate c-1. LC-MS: Measured value: 325.29 ([M+H)) + Theoretical value: 324.26.

[0162] Under nitrogen protection, 10 mmol of intermediate c-1, 11 mmol of starting material M12, 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 the mixture was refluxed for 15 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate J3. LC-MS: Measured value: 401.37 ([M+H)) + Theoretical value: 400.29.

[0163] 4. Synthesis of intermediate J4

[0164]

[0165] Under nitrogen protection, 10 mmol of starting material M7, 11 mmol of starting material M8, 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 the mixture was refluxed for 15 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate J4. LC-MS: Measured value: 409.31 ([M+H)) + Theoretical value: 408.26.

[0166] 5. Synthesis of intermediate J5

[0167]

[0168] Under nitrogen protection and anhydrous / oxygen-free conditions, 78.4 mmol of starting material M7 was dissolved in 100 mL of anhydrous THF. The reaction system was cooled to -20°C, and 41 mL of 2M i-PrMgCl₂ was slowly added dropwise. After the addition was complete, the temperature was maintained and stirring continued for 1 hour. 78.4 mmol of acetone was mixed with 20 mL of anhydrous THF and slowly added to the reaction system. The mixture was then slowly raised to room temperature and stirred for 3 hours. The reaction was subsequently quenched with saturated ammonium chloride solution. The mixture was extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated. The final product was then subjected to silica gel column chromatography (petroleum ether / ethyl acetate = 5 / 1) to obtain intermediate Y6. LC-MS: Measured value: 250.88 ([M+H) + Theoretical value: 249.98.

[0169] 60 mmol of intermediate Y6 was dissolved in 300 mL of anhydrous DCM. The reaction system was cooled to 0 °C, and 60 mmol of Et3SiH and 10 mL of 6 M BF3-Et2O were slowly added sequentially. After reacting for 1 hour, the reaction was quenched with saturated sodium bicarbonate solution. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated. Intermediate J5 was obtained by column chromatography (petroleum ether). LC-MS: 234.93 ([M+H)) + Theoretical value: 233.99.

[0170] 6. Synthesis of intermediate J6

[0171]

[0172] 12 mmol of starting material M7 and 11 mmol of starting material M8 were added to a three-necked flask and dissolved in a mixed solvent (70 mL toluene, 35 mL ethanol). Then, 0.1 mmol of Pd(PPh3)4 and 15 mL of 3 mol / L K2CO3 aqueous solution were added. The mixture was heated to reflux for 12 hours under nitrogen protection. A sample was spotted onto a TLC plate to confirm complete reaction. After cooling to room temperature, the reaction mixture was filtered through a diatomaceous earth filter, washed with chloroform, and the resulting filtrate was evaporated under vacuum. The residue was purified by column chromatography on silica gel using hexane / toluene as eluent to give intermediate J6. LC-MS: Measured value: 379.14 ([M+H) + Precision quality: 378.08.

[0173] 7. Synthesis of intermediate J7

[0174]

[0175] Under nitrogen protection, 335 mmol of starting material M9 was dissolved in 500 mL of anhydrous ACN. The reaction system was cooled to 0°C, and 335 mmol of NBS was slowly added. After the addition was complete, the mixture was stirred for 3 hours while maintaining the temperature. The reaction was then quenched with water, extracted successively with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated. The resulting product was then subjected to silica gel column chromatography (petroleum ether / ethyl acetate = 20 / 1) to obtain intermediate Y7. LC-MS: Measured value: 228.17 ([M+H) + Theoretical value: 227.03.

[0176] Under nitrogen protection, 136 mmol of intermediate Y7, 136 mmol of starting material M10, and 408 mmol of potassium carbonate were dissolved in 310 mL of 1,4-dioxane and 100 mL of water. 2.71 mmol of Pd(dppf)Cl2 was added, and the reaction mixture was reacted at 80 °C for 16 hours. After the reaction was complete, the mixture was filtered while hot, extracted successively with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated. The resulting product was then subjected to silica gel column chromatography (petroleum ether / ethyl acetate = 20 / 1) to obtain intermediate Y8. LC-MS: Measured value: 282.36 ([M+H) + Theoretical value: 281.21.

[0177] Under nitrogen protection, 178 mmol of intermediate Y8 was dissolved in 400 mL of anhydrous THF. The reaction system was cooled to 0°C, and a solution of concentrated hydrochloric acid (81.7 mL) in water (235 mL) was slowly added dropwise. After the addition was complete, a solution of 267 mmol of NaNO2 in water (90 mL) was slowly added dropwise. The reaction temperature was kept below 5°C. After the addition was complete, stirring was continued for 15 minutes. A solution of 355 mmol of KI in water (371.5 mL) was added dropwise to the reaction system, keeping the reaction temperature below 5°C. After the addition was complete, stirring was continued for 2 hours. The reaction was then quenched with saturated sodium sulfite solution, extracted successively with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated. The intermediate Y9 was then obtained by silica gel column chromatography (petroleum ether). LC-MS: Measured value: 393.24 ([M+H) + Theoretical value: 392.10.

[0178] Under nitrogen protection and anhydrous and oxygen-free conditions, 337 mmol of starting material M11, 370 mmol of B2Pin2, and 101 mmol of KOAc were dissolved in 500 mL of DMF. 6.73 mmol of Pd(dppf)Cl2 was added, and the mixture was stirred at 100 °C for 16 hours. After the reaction was complete, the mixture was filtered while hot, and most of the DMF was concentrated using an oil pump. The solution was then dissolved in ethyl acetate, washed successively with water, saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated. The solution was then subjected to silica gel column chromatography (petroleum ether / ethyl acetate = 20 / 1) to obtain intermediate Y10. LC-MS: Measured value: 256.29 ([M+H) + Theoretical value: 255.12.

[0179] Under nitrogen protection and anhydrous and oxygen-free conditions, 384 mmol of intermediate Y9, 384 mmol of intermediate Y10, and 551 mmol of potassium carbonate were dissolved in 720 mL of 1,4-dioxane and 150 mL of water. 3.67 mmol of Pd(dppf)Cl2 was added, and the reaction mixture was reacted at 60 °C for 16 hours. After the reaction was complete, the mixture was filtered while hot, extracted successively with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated. The resulting product was then subjected to silica gel column chromatography (petroleum ether / ethyl acetate = 50 / 1) to obtain intermediate Y11. LC-MS: Measured value: 394.31 ([M+H) + Theoretical value: 393.23.

[0180] 300 mL of acetonitrile was added to intermediate Y11 (25.4 mmol) and CuBr2 (127 mmol). The reaction system was cooled to 0 °C, and then 10.24 mL of Isoamyl nitrite was slowly added dropwise. After reacting for 16 hours, the reaction was quenched with ammonia solution, extracted successively with ethyl acetate, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated, and intermediate J7 was obtained by column chromatography (petroleum ether). LC-MS: 457.38 ([M+H)) + Theoretical value: 456.13.

[0181] II. Synthesis of Compounds in Examples

[0182] Example 1: Synthesis of Compound 65:

[0183]

[0184] Preparation of intermediate K1:

[0185] Intermediate J1 (20 mmol) and 120 mL of anhydrous DMF were added sequentially to a three-necked flask. Under nitrogen protection, mineral oil-coated (65%) NaH (net content 15 mmol) was added in portions under ice-water bath conditions. The mixture was stirred for 0.5 hours, and a solution of raw material A1 (10 mmol) dissolved in 30 mL of anhydrous DMF was slowly added dropwise. After the reaction was complete, 150 mL of water was added to quench the reaction, and the large amount of precipitate was filtered out. The precipitate was collected, dried over anhydrous sodium sulfate solution in dichloromethane, filtered, concentrated, and purified by silica gel column chromatography using petroleum ether as the developing solvent to obtain intermediate K1. LC-MS: Measured value: 649.28 ([M+H) + Theoretical value: 648.19.

[0186] Preparation of intermediate P1:

[0187] Intermediate K1 (5.0 mmol) and tert-butylbenzene (50 mL) were added sequentially to a low-temperature flask. The mixture was cooled to -78 °C, and a hexane solution of n-butyllithium (5.5 mmol) was slowly added. The mixture was then stirred and brought to room temperature. Hexane was removed under negative pressure at 60 °C. Nitrogen gas was then introduced for protection, and the reaction proceeded for 2 hours. BBr3 (6.0 mmol) was added at -42 °C, and the mixture was stirred for another 2 hours. The temperature was then slowly restored to room temperature, and the mixture was stirred at room temperature for 12 hours. DIPEA (N,N-diisopropylethylamine) (10 mmol) was added under ice-water bath conditions, and the mixture was refluxed at 120 °C for 36 hours. The reaction was cooled to room temperature, and the solution was filtered through diatomaceous earth. The organic phase was collected, and high-boiling solvents were removed by vacuum distillation. The solution was dissolved in dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography using toluene as the developing solvent to obtain intermediate P1. LC-MS: Measured value: 579.33 ([M+H)). + Theoretical value: 578.26.

[0188] Preparation of intermediate T1:

[0189] Intermediate P1 (10.0 mmol), pinacol diboronate (15 mmol), [Ir(COD)(OCH3)]2 (0.06 mmol), and 150 mL of tetrahydrofuran were added sequentially to a single-necked flask. The reaction was carried out at room temperature for 12 hours under nitrogen protection. The reaction was then filtered, the organic phase was concentrated, and the compounds were separated by silica gel column chromatography using petroleum ether:ethyl acetate = 1:1 as the developing solvent to obtain intermediate T1. This reaction exhibited relatively good selectivity (refer to DOI: 10.31635 / ccschem.021.202101033), with boron-p-boron esters showing higher activity and selectivity. LC-MS: Measured value: 705.40 ([M+H) + Theoretical value: 704.35.

[0190] Preparation of compound 65:

[0191] Intermediate T1 (10.0 mmol), starting material E1 (11.0 mmol), Pd(PPh3)4 catalyst (0.1 mmol), 150 mL of a tetrahydrofuran:water mixture (10:1), and potassium carbonate (20 mmol) were added sequentially to a two-necked flask. The mixture was then stirred at 80 °C for 5.5 hours under nitrogen protection. After cooling, the liquid-liquid phase was separated and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The compound was separated by silica gel column chromatography using petroleum ether:ethyl acetate (5:1) as the developing solvent to obtain compound 65. (1 × 10⁻⁶) -5 The half-width at half maximum (WHM) is 27 nm.

[0192] Example 2: Synthesis of Compound 81:

[0193]

[0194] Preparation of intermediate K2:

[0195] Intermediate J1 (10 mmol) and 100 mL of anhydrous DMF were added sequentially to a three-necked flask. Under nitrogen protection, mineral oil-coated (65%) NaH (net content 12 mmol) was added in portions under ice-water bath conditions. The mixture was stirred for 0.5 hours, and a solution of raw material A2 (10 mmol) dissolved in 20 mL of anhydrous DMF was slowly added dropwise. After the reaction was complete, 150 mL of water was added to quench the reaction, and the large amount of precipitate was filtered out. The precipitate was collected, dried over anhydrous sodium sulfate solution in dichloromethane, filtered, concentrated, and purified by silica gel column chromatography using petroleum ether as the developing solvent to obtain intermediate K2. LC-MS: Measured value: 497.31 ([M+H) + Theoretical value: 496.10.

[0196] Preparation of intermediate P2:

[0197] Add raw material B1 (10 mmol) and 100 mL of anhydrous DMF sequentially to a three-necked flask. Under nitrogen protection, add mineral oil-coated (65%) NaH (net content 12 mmol) in portions under ice-water bath conditions. Stir the mixture for 0.5 hours, then slowly add intermediate K2 (10 mmol) solution dissolved in 20 mL of anhydrous DMF. After the reaction is complete, quench the reaction with 150 mL of water and filter out the large amount of precipitate. Collect the precipitate, dry it with dichloromethane solution and anhydrous sodium sulfate, filter it, concentrate the reaction solution, and purify it by silica gel column chromatography using petroleum ether as the developing solvent to obtain intermediate P2. LC-MS: Measured value: 809.17 ([M+H) + Theoretical value: 808.22.

[0198] Preparation of compound 81:

[0199] Intermediate P2 (5.0 mmol) and tert-butylbenzene (50 mL) were added sequentially to a low-temperature flask. The mixture was cooled to -78 °C, and a hexane solution of n-butyllithium (5.5 mmol) was slowly added. The mixture was then stirred and brought to room temperature. Subsequently, the hexane was removed under negative pressure at 60 °C. Nitrogen gas was then introduced for protection, and after 2 hours of reaction, BBr3 (6.0 mmol) was added at -42 °C. The mixture was stirred for 2 hours and then slowly brought to room temperature. After stirring at room temperature for 12 hours, DIPEA (N,N-diisopropylethylamine) (10 mmol) was added under ice-water bath conditions, and the mixture was heated to 120 °C and refluxed for 36 hours. The reaction was cooled to room temperature, and the solution was filtered through diatomaceous earth. The organic phase was collected, and the high-boiling solvent was removed by vacuum distillation. The solution was dissolved in dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography using toluene as the developing solvent to obtain the target compound 81. -5 The half-width at half maximum (WHM) is 23 nm.

[0200] Example 3: Synthesis of Compound 142:

[0201]

[0202] Preparation of intermediate K3:

[0203] Intermediate K3 was synthesized using intermediate K2 as a reference, except that intermediate J1 was replaced with intermediate J2. LC-MS: Measured value: 609.36 (M+H) + Theoretical value: 608.22.

[0204] Preparation of intermediate P3:

[0205] The synthesis of intermediate P3 referenced intermediate P2, except that intermediate K3 replaced intermediate K2, and starting material B2 replaced starting material B1, yielding intermediate P3. LC-MS: Measured value: 908.44 ([M+H)) + Theoretical value: 907.35.

[0206] Preparation of compound 142:

[0207] The synthesis of compound 142 is based on compound 81, except that intermediate P2 is replaced by intermediate P3, yielding compound 142. In toluene solution (1×10⁻⁶) -5 The full width at half maximum (FWHM) is 21 nm.

[0208] Example 4: Synthesis of Compound 154:

[0209]

[0210]

[0211] Preparation of intermediate K4:

[0212] The synthesis of intermediate K4 referenced intermediate K2, except that intermediate J7 replaced starting material A2, and intermediate J2 replaced intermediate J1, yielding intermediate K4. LC-MS: Measured value: 797.43 ([M+H)) + Theoretical value: 796.38.

[0213] Preparation of intermediate P4:

[0214] The synthesis of intermediate P4 referenced intermediate P2, except that intermediate K4 replaced intermediate K2, and starting material B3 replaced starting material B1, yielding intermediate P4. LC-MS: Measured value: 1096.56 (M+H) + Theoretical value: 1095.51.

[0215] Preparation of compound 154:

[0216] The synthesis of compound 154 is based on compound 81, except that intermediate P2 is replaced by intermediate P4, yielding compound 154. In toluene solution (1×10⁻⁶) -5 The half-width at half maximum (WHM) is 25 nm.

[0217] Example 5: Synthesis of Compound 199:

[0218]

[0219] Preparation of intermediate K5:

[0220] Intermediate K5 was synthesized using the same method as intermediate K2, except that intermediate J5 was used to replace starting material A2. LC-MS: Measured value: 463.29 ([M+H)). + Theoretical value: 462.11.

[0221] Preparation of intermediate P5:

[0222] The synthesis of intermediate P5 referenced intermediate P2, except that intermediate K5 replaced intermediate K2, and intermediate J3 replaced starting material B1, yielding intermediate P5. LC-MS: Measured value: 843.46 ([M+H)) + Theoretical value: 842.39.

[0223] Preparation of compound 199:

[0224] The synthesis of compound 199 is based on compound 81, except that intermediate P2 is replaced by intermediate P5, yielding compound 199. In toluene solution (1×10⁻⁶)-5 The half-width at half maximum (WHM) is 27 nm.

[0225] Example 6: Synthesis of Compound 256:

[0226]

[0227] Preparation of intermediate K6:

[0228] The synthesis of intermediate K6 referenced intermediate K2, except that intermediate J7 was used to replace starting material A2 to obtain intermediate K6. LC-MS: Measured value: 685.18 ([M+H)) + Theoretical value: 684.25.

[0229] Preparation of intermediate P6:

[0230] The synthesis of intermediate P6 referenced intermediate P2, except that intermediate K6 replaced intermediate K2, and intermediate J4 replaced starting material B1, yielding intermediate P6. LC-MS: Measured value: 1073.56 ([M+H)) + Theoretical value: 1072.50.

[0231] Preparation of compound 256:

[0232] The synthesis of compound 256 is based on compound 81, except that intermediate P2 is replaced by intermediate P6 to obtain compound 256. In toluene solution (1×10⁻⁶) -5 The half-width at half maximum (WHM) is 29 nm.

[0233] Example 7: Synthesis of Compound 262:

[0234]

[0235] Preparation of intermediate K7:

[0236] Intermediate K7 was synthesized using the same method as intermediate K2, except that intermediate J6 was used to replace starting material A2. LC-MS: Measured value: 607.14 ([M+H)). + Theoretical value: 606.20.

[0237] Preparation of intermediate P7:

[0238] The synthesis of intermediate P7 referenced intermediate P2, except that intermediate K7 replaced intermediate K2, and starting material B4 replaced starting material B1, yielding intermediate P7. LC-MS: Measured value: 919.21 ([M+H)) + Theoretical value: 918.33.

[0239] Preparation of compound 262:

[0240] The synthesis of compound 262 is based on compound 81, except that intermediate P2 is replaced by intermediate P7 to obtain compound 262. In toluene solution (1×10⁻⁶) -5 The half-width at half maximum (WHM) is 23 nm.

[0241] Example 8: Synthesis of compound 305:

[0242]

[0243] Preparation of intermediate P8:

[0244] The synthesis of intermediate P8 is based on intermediate P2, except that starting material B1 is replaced by starting material B5. LC-MS: Measured value: 807.28 ([M+H)). + Theoretical value: 806.20.

[0245] Preparation of compound 305:

[0246] The synthesis of compound 305 is based on compound 81, except that intermediate P2 is replaced by intermediate P8, yielding compound 305. In toluene solution (1×10⁻⁶) -5 The half-width at half maximum (WHM) is 20 nm.

[0247] Note: Half-width at half-maximum (FWHM) was measured using a Horiba Fluorolog-3 series fluorescence spectrometer.

[0248] The structural characterization of the compounds obtained in each embodiment is shown in Table 1.

[0249] Table 1

[0250]

[0251] The compounds of this invention can be used as doping materials for the light-emitting layer in light-emitting devices.

[0252] Device Examples

[0253] The following describes in detail the application effects of the OLED material synthesized in the present invention in devices through device examples 1-8 and device comparative examples 1-2. The fabrication processes of device examples 2-8 and device comparative examples 1-2 are completely identical to those of device example 1, and the same substrate and electrode materials are used, with the electrode film thickness remaining consistent. The only difference is the replacement of the light-emitting layer material in the device. The layer structures and test results of each device example are shown in Tables 2 and 3, respectively.

[0254] Device Example 1

[0255] like Figure 1 As shown, the transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (film thickness 150nm) is washed sequentially with a cleaning agent (Semiclean M-L20), then with pure water, dried, and finally with ultraviolet-ozone to remove organic residues from the transparent ITO surface. After the above washing, HT-1 and HI-1 with a thickness of 10nm are deposited on the ITO anode layer 2 using a vacuum evaporation apparatus as a hole injection layer 3, with a mass ratio of HT-1 to HI-1 of 97:3. Next, a 60nm thick layer of HT-1 is deposited as a hole transport layer 4. Subsequently, a 30nm thick layer of EB-1 is deposited as an electron blocking layer 5. After the electron blocking materials are deposited, the light-emitting layer 6 of the OLED light-emitting device is fabricated, using GH-1 and GH-2 as the host materials and compound 65 as the dopant material, with a mass ratio of GH-1, GH-2, and compound 65 of 69:30:1. The light-emitting layer has a film thickness of 30nm. Following the aforementioned light-emitting layer 6, HB-1 is vacuum-deposited to a thickness of 5 nm; this layer serves as the hole-blocking layer 7. Following the hole-blocking layer 7, ET-1 and Liq are vacuum-deposited at a mass ratio of 1:1, resulting in a film thickness of 30 nm; this layer serves as the electron transport layer 8. On the electron transport layer 8, a LiF layer with a thickness of 1 nm is fabricated using a vacuum evaporation apparatus; this layer serves as the electron injection layer 9. On the electron injection layer 9, an 80 nm thick Mg:Ag electrode layer is fabricated using a vacuum evaporation apparatus, with a Mg:Ag mass ratio of 1:9; this layer serves as the cathode layer 10.

[0256] The application effects of the OLED material synthesized in this invention in devices are described in detail below through device examples 9-16 and device comparative examples 3-4. Device examples 10-16 and device comparative examples 3-4 of this invention have the same fabrication process as device example 9, and use the same substrate material and electrode material, with the same electrode film thickness. The only difference is the replacement of the light-emitting layer material in the device. The layer structure and test results of each device example are shown in Tables 2 and 3, respectively.

[0257] Device Example 9

[0258] The transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (film thickness 150nm) is washed sequentially with a cleaning agent (Semiclean M-L20), followed by washing with pure water, drying, and then ultraviolet-ozone washing to remove organic residues from the transparent ITO surface. After the above washing, a 10nm thick layer of HT-1 and HI-1 is deposited on the ITO anode layer 2 using a vacuum evaporation apparatus as a hole injection layer 3, with a mass ratio of HT-1 to HI-1 of 97:3. Next, a 60nm thick layer of HT-1 is deposited as a hole transport layer 4. Finally, a 30nm thick layer of EB-1 is deposited as an electron blocking layer 5. After the electron blocking material is deposited, the emitting layer 6 of the OLED light-emitting device is fabricated. GH-1 and GH-2 are used as the host materials, GD-1 is used as the first dopant, and compound 65 is used as the second dopant. The mass ratio of GH-1, GH-2, GD-1, and compound 65 is 66:30:3:1, and the thickness of the emitting layer is 30 nm. After the emitting layer 6, HB-1 is vacuum-deposited to a thickness of 5 nm; this layer is the hole blocking layer 7. After the hole blocking layer 7, ET-1 and Liq are vacuum-deposited to a mass ratio of 1:1, with a thickness of 30 nm; this layer is the electron transport layer 8. On the electron transport layer 8, a LiF layer with a thickness of 1 nm is fabricated using a vacuum evaporation apparatus; this layer is the electron injection layer 9. On the electron injection layer 9, a Mg:Ag electrode layer with a thickness of 80 nm is fabricated using a vacuum evaporation apparatus; the mass ratio of Mg to Ag is 1:9; this layer is used as the cathode layer 10.

[0259] The molecular structural formulas of the relevant materials are shown below:

[0260]

[0261]

[0262] After completing the OLED light-emitting device as described above, the anode and cathode are connected using a known driving circuit, and the current efficiency and lifetime of the device are measured. Examples and comparative examples of devices prepared using the same method are shown in Table 2; the test results for the current efficiency and lifetime of the obtained devices are shown in Table 3.

[0263] Table 2

[0264]

[0265]

[0266] Table 3

[0267]

[0268] Note: Current efficiency and emission peak were measured using an IVL (current-voltage-brightness) testing system (Suzhou Fushida Scientific Instruments Co., Ltd.); the lifetime testing system was the EAS-62C OLED device lifetime tester from System Technology Inc., Japan; LT95 refers to the time it takes for the device brightness to decay to 95%; all data are within 10 mA / cm². 2 Next test.

[0269] As can be seen from the device data results in Table 3, compared with the devices in Comparative Examples 1-4, the organic light-emitting devices of the present invention achieve significant improvements in current efficiency and lifetime compared with OLED devices made of known materials, whether in a single-doped or double-doped system; when using an exciton-sensitized material as the first dopant, the device efficiency is significantly improved compared with that in the single-doped system.

[0270] In summary, the above are merely preferred embodiments of the present invention and are not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention should be included within the protection scope of the present invention.

Claims

1. A resonance-type organic compound, characterized in that, The structure of the resonance-type organic compound is shown in any one of general formulas (4-2) to (4-7): In general formulas (4-2) to (4-7), Z is represented as C-R1; Each occurrence of R1, whether identical or different, is represented by H, deuterium atom, halogen atom, cyano group, or substituted or unsubstituted C1-C. 10 Alkyl, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Silyl, 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; Z1, Z2, and Z3 are independently represented as CH or C-R5; each occurrence of R5, whether the same or different, represents a deuterium atom, a halogen atom, a cyano group, or a C1-C group. 10 Alkyl, C6-C 30 aryl, C3-C 30 One of the heteroaryl groups; Ar2 and Ar3 are respectively represented as substituted or unsubstituted C6-C. 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl groups; Ra and Rb are independently represented as hydrogen atoms, substituted or unsubstituted C1-C atoms, respectively. 10 Alkyl, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl groups; The substituents used for the substituent groups are optionally selected from halogen atoms, deuterium atoms, cyano groups, C1-C... 10 Alkyl, C5-C 10 cycloalkyl, C1-C 10 alkoxy groups, C6-C 30 Aryl, C3-C 30 One or more of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one of O, S, N, and Si.

2. A resonance-type organic compound, characterized in that, The structure of the resonance-type organic compound is shown in any one of general formulas (1-5), (1-6), (1-8) to (1-13): In general formulas (1-5), (1-6), (1-8) to (1-13), Z is represented as C-R1; Each occurrence of R1, whether identical or different, is represented by H, deuterium atom, halogen atom, cyano group, or substituted or unsubstituted C1-C. 10 Alkyl, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Silyl, 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; Z1, Z2, Z3, Z4, Z5, Z6, and Z7 are independently represented as CH or C-R5; each occurrence of R5, whether the same or different, represents a deuterium atom, a halogen atom, a cyano group, or a C1-C group. 10 Alkyl, C6-C 30 aryl, C3-C 30 One of the heteroaryl groups; Ar2 represents substituted or unsubstituted C6-C. 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl groups; The substituents used for the substituent groups are optionally selected from halogen atoms, deuterium atoms, cyano groups, C1-C... 10 Alkyl, C5-C 10 cycloalkyl, C1-C 10 alkoxy groups, C6-C 30 Aryl, C3-C 30 One or more of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one of O, S, N, and Si.

3. The resonance-type organic compound according to claim 1, characterized in that, Each instance of R1, whether identical or different, is represented by hydrogen, deuterium atom, halogen atom, cyano group, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted isopropyl group, substituted or unsubstituted tert-butyl group, substituted or unsubstituted cyclohexyl group, substituted or unsubstituted adamantyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted diphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthracene group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted pyridyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted... Substituted furanyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted triazineyl, substituted or unsubstituted 4a,9a-dimethyl-9-phenyl-1,2,3,4-tetrahydrocarbazole; The R5, whether appearing the same or different each time, is represented by hydrogen, deuterium atom, halogen atom, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, diphenyl, terphenyl, naphthyl, anthracene, phenanthryl, pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, carbazoyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl, triazine, 4a,9a-dimethyl-9-phenyl-1,2,3,4-tetrahydrocarbazole; Ar2 and Ar3 are respectively independently represented as substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiophenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl; The substituents used for the substituent groups are selected from one or more of the following: deuterium atom, chlorine atom, fluorine atom, trifluoromethyl, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthrene, pyridinyl, pyrazinyl, pyrazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheneyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheninyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazoleyl, N-phenylcarbazoleyl, carbazolinyl, and aziphenanthreneyl.

4. The resonance-type organic compound according to claim 2, characterized in that, Each instance of R1, whether identical or different, is represented by hydrogen, deuterium atom, halogen atom, cyano group, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted isopropyl group, substituted or unsubstituted tert-butyl group, substituted or unsubstituted cyclohexyl group, substituted or unsubstituted adamantyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted diphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthracene group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted pyridyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted... Substituted furanyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted triazineyl, substituted or unsubstituted 4a,9a-dimethyl-9-phenyl-1,2,3,4-tetrahydrocarbazole; The R5, whether appearing the same or different each time, is represented by hydrogen, deuterium atom, halogen atom, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, diphenyl, terphenyl, naphthyl, anthracene, phenanthryl, pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, carbazoyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl, triazine, 4a,9a-dimethyl-9-phenyl-1,2,3,4-tetrahydrocarbazole; Ar2 represents substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiophenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl; The substituents used for the substituent groups are selected from one or more of the following: deuterium atom, chlorine atom, fluorine atom, trifluoromethyl, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthrene, pyridinyl, pyrazinyl, pyrazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheneyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheninyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazoleyl, N-phenylcarbazoleyl, carbazolinyl, and aziphenanthreneyl.

5. 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:

6. An organic light-emitting device comprising a cathode, an anode, and a functional layer, wherein the functional layer is located between the cathode and the anode, characterized in that, The functional layer includes a light-emitting layer, which comprises a host material and a dopant material, wherein the dopant material is a resonant organic compound as described in any one of claims 1-5.

7. The organic light-emitting device according to claim 6, characterized in that, The functional layer includes a light-emitting layer, which comprises a first host material, a second host material, and a dopant material. At least one of the first host material and the second host material is a TADF material, and the dopant material is a resonant organic compound as described in any one of claims 1-5.

8. The organic light-emitting device according to claim 6, wherein the light-emitting layer comprises a host material, an exciton-sensitizing material, and a dopant material, characterized in that, The exciton sensitizing material is a complex containing a metal element, and the doping material is a resonance-type organic compound as described in any one of claims 1-5.

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