Luminescent material, organic electroluminescent device and preparation method

Abstract

The invention discloses a luminescent material, an organic electroluminescent device and a preparation method, and relates to the technical field of organic electroluminescence. The structural general formula of the luminescent material is shown as a formula (1) or a formula (2), ar1, Ar2 and Ar5 are respectively and independently a substituted or unsubstituted C6-C60 aryl group and a substituted or unsubstituted C4-C60 heteroaryl group; ar3 is a group containing triphenylsilane and having a total number of carbon atoms of 18-160; ar4 is selected from one of the following structures:,..., and the like. The luminescent material provided by the invention is a pure green luminescent material, and has high color purity, high efficiency, high stability, good solubility and film-forming suitability.

Description

Technical Field

[0001] This invention relates to the field of organic electroluminescence technology, and more particularly to a luminescent material, an organic electroluminescent device, and a preparation method thereof. Background Technology

[0002] In the optoelectronic field, organic light-emitting diodes (OLEDs) have attracted attention due to their high brightness, strong contrast, and good color saturation, and have been widely used in mobile phones, televisions, and automotive displays. For ultra-high-definition displays, luminescent materials not only need to possess a narrow emission half-width (FWHM) to achieve high color purity, but also need to maintain good thermal stability and device lifetime under high brightness. However, existing fluorescent, phosphorescent, and traditional thermally activated delayed fluorescence (TADF) materials generally have broad emission bands and obvious vibrational structures, often relying on filters to improve color purity, thereby reducing photon utilization and limiting device efficiency and lifetime.

[0003] In recent years, multiple resonance thermally activated delayed fluorescence (MR-TADF) materials developed based on B / N atom-doped polycyclic aromatic hydrocarbons have benefited from their rigid structural framework and localized electronic properties, enabling them to achieve efficient narrow-band emission and are considered as strong candidate materials for next-generation high color gamut displays.

[0004] However, existing MR-TADF materials still face several key challenges in practical device applications, such as luminescence quenching caused by intermolecular stacking and aggregation, and efficiency roll-off and lifetime degradation under high brightness, making it difficult to simultaneously achieve high color purity, high efficiency, and device stability. Therefore, it is urgent to develop luminescent material systems that combine high color purity, high efficiency, and high stability, and to improve their adaptability in devices, especially in solution processing and inkjet printing processes.

[0005] Therefore, existing technologies still need to be improved and developed. Summary of the Invention

[0006] In view of the shortcomings of the prior art, the purpose of this invention is to provide a luminescent material, an organic electroluminescent device and a preparation method, aiming to provide a luminescent material with high color purity, high efficiency and high stability.

[0007] The technical solution of the present invention is as follows: In a first aspect, the present invention provides a luminescent material, wherein the luminescent material has a general structural formula as shown in formula (1) or formula (2):

[0008] Among them, Ar1, Ar2, and Ar5 are each independently substituted C6-C. 60 Aryl, unsubstituted C6-C 60Aryl, substituted C4-C 60 heteroaryl or unsubstituted C4-C 60 Mixed aromatics; Ar3 is a group containing 18-160 carbon atoms in a triphenylsilane group; Ar4 is selected from one of the following structures: , , , , and ; X1, X2, X3, X4, and X5 are each independently selected from single bonds, O, S, Se, and CR. a R b SiR a R b NR c One of them; and when X1, X2, or X3 is a single bond, it can fuse with Ar1, Ar2, or Ar5 to form a five-membered ring, six-membered ring, or seven-membered ring structure; R a R b R c Each group is independently selected from H, D (deuterium), F, Cl, Br, I, benzyl, ester, amide, carbonyl, aldehyde, nitro, and unsubstituted C1-C groups. 30 Alkyl, substituted C1-C 30 Alkyl groups (such as trifluoromethyl), unsubstituted C1-C 10 Alkoxy, substituted C1-C 10 Alkoxy, unsubstituted C3-C 30 cycloalkyl, substituted C3-C 30 cycloalkyl, unsubstituted C1-C 30 Alkylthio, substituted C1-C 30 Alkylthio, unsubstituted C6-C 30 Aryl, substituted C6-C 30 Aryl, unsubstituted C4-C 30 heteroaryl, substituted C4-C 30 One of the heteroaryl groups; Indicates the connection site.

[0009] The luminescent material provided by this invention is a pure green luminescent material that combines high color purity, high efficiency, high stability, good solubility, and film-forming compatibility. Specifically, this luminescent material is a multi-resonance compound with a rigid multi-resonance molecular framework and exhibits narrow-band green light emission. This invention introduces non-conjugated three-dimensional structural units of triphenylsilane and its derivatives into the structure of the luminescent material. While maintaining the narrow-band pure green light emission characteristics of the boron-based multi-resonance framework, this invention improves the morphological and thermal stability of the material, as well as its solubility and solution film-forming properties. Furthermore, it significantly reduces intermolecular stacking, suppresses harmful intermolecular aggregation and aggregation-induced non-radiative decay (i.e., it can suppress intermolecular stacking, non-radiative transition channels, and aggregation-induced quenching, reducing non-radiative losses). This is beneficial for improving device stability and external quantum efficiency in electroluminescent devices, thereby achieving synergistic optimization of high color purity, high efficiency, and long lifetime. Meanwhile, the luminescent material exhibits better solubility and film-forming compatibility, making it suitable for solution processing and inkjet printing to prepare the luminescent layer of organic electroluminescent devices. This meets the requirements of printing processes for material solubility, film uniformity, and device reliability, thus satisfying the development needs of printed display devices. Using the luminescent material provided by this invention as the guest material for the luminescent layer in the preparation of organic electroluminescent devices enables these devices to possess narrow-band emission, high external quantum efficiency, and significantly extended device lifetime.

[0010] Alternatively, Ar3 is selected from one of the following structures: , , , , and ; Wherein, R2 to R8 are located at any connectable position on their respective benzene rings, and R2 to R8 are monosubstituted or polysubstituted, each independently selected from at least one of the following groups: H, D, , , , , and ; in, Indicating the connection sites, R9 and R10 are located at any connectable position on their respective benzene rings. R9 and R10 are each independently selected from H, D, F, Cl, Br, I, benzyl, ester, amide, carbonyl, aldehyde, nitro, and unsubstituted C1-C groups. 30 Alkyl, substituted C1-C 30 Alkyl groups (such as trifluoromethyl, cyano-substituted C1-C) 30 Alkyl, trifluoromethyl substituted C1-C 30Alkyl), unsubstituted C1-C 10 Alkoxy, substituted C1-C 10 Alkoxy, unsubstituted C1-C 10 Alkylamino, substituted C1-C 10 Alkylamino, unsubstituted C3-C 10 cycloalkyl, substituted C3-C 10 cycloalkyl, unsubstituted C1-C 30 Alkylthio, substituted C1-C 30 Alkylthio, unsubstituted C6-C 30 Aryl, substituted C6-C 30 Aryl, unsubstituted C4-C 30 heteroaryl, substituted C4-C 30 One of the heteroaryl groups.

[0011] In this invention, R2 to R8 are monosubstituted or polysubstituted. For example, when R2 on a certain benzene ring in a certain structure is polysubstituted, each R2 can be independently selected from the above-mentioned groups.

[0012] In addition, the benzene rings of the structures shown in formulas (3)-(8) can be fully deuterated (e.g., R2 to R8 are all D) or partially deuterated (e.g., some R2 to R8 are D).

[0013] Modification with these triphenylsilanes, tetraphenylsilanes and their derivatives (i.e., the introduction of these non-conjugated three-dimensional molecular configurations into luminescent materials) can suppress the spectral broadening problem caused by π-π stacking, thereby enabling the luminescent materials to have high color purity; it can significantly reduce intermolecular stacking, suppress harmful intermolecular aggregation and nonradiative transition channels, which is beneficial to improving device stability and external quantum efficiency in electroluminescent devices; it can also improve the morphological stability and thermal stability of the material, and improve solubility and solution film-forming properties.

[0014] Optionally, the substituted C6-C 60 Aryl, substituted C4-C 60 The substituents in the heteroaryl group are each independently selected from H, D, F, Cl, Br, I, nitrile, acyl, or unsubstituted C1-C. 30 Alkyl, substituted C1-C 30 Alkyl groups (e.g., trifluoromethyl), unsubstituted C1-C 10 Alkoxy, substituted C1-C 10 Alkoxy, unsubstituted C3-C 30 cycloalkyl, substituted C3-C 30 cycloalkyl, unsubstituted C1-C 30 Alkylthio, substituted C1-C 30 Alkylthio, unsubstituted C6-C30 Aryl, substituted C6-C 30 Aryl, unsubstituted C4-C 30 heteroaryl, substituted C4-C 30 One of the heteroaryl groups.

[0015] Alternatively, Ar1, Ar2, and Ar5 may each be independently selected from one of the following structures:

[0016] ; in, Indicates the linking site. R11 is located at any connectable position on its benzene ring. In different structural formulas, R11 is independently selected from H, D, F, Cl, Br, I, cyano, benzyl, ester, amide, carbonyl, aldehyde, nitro, substituted amino, unsubstituted amino, substituted borane, unsubstituted borane, and substituted C1-C. 30 Alkyl groups (e.g., trifluoromethyl, cyano-substituted C1-C) 30 Alkyl groups), unsubstituted C1-C 30 Alkyl, substituted C1-C 10 Alkoxy, unsubstituted C1-C 10 Alkoxy, substituted C1-C 10 Alkylamino, unsubstituted C1-C 10 Alkylamino, substituted C3-C 30 cycloalkyl, unsubstituted C3-C 30 cycloalkyl, substituted C1-C 30 Alkylthio, unsubstituted C1-C 30 Alkylthio, substituted C6-C 30 Aryl, unsubstituted C6-C 30 Aryl, substituted C4-C 30 heteroaryl, unsubstituted C4-C 30 One of the heteroaryl groups.

[0017] In some embodiments, R11 in different structural formulas is independently selected from H, D, F, Cl, Br, I, cyano, adamantyl, methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopentyl, deuterated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthracene, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazoyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl The following are considered as a derivative of the following: ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, phenyl-substituted amino (e.g., diphenylamino), tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthoneyl, phenyl-substituted triazineyl, phenyl-substituted boronyl, methoxy, and tert-butoxy.

[0018] Optionally, the luminescent material is selected from one of the following structures:

[0019] .

[0020] A second aspect of the present invention provides a method for preparing the luminescent material as described above, comprising the following steps: Will and or After the reaction, we get That is, the luminescent material; or, Will and or After the reaction, we get That is, the luminescent material; Where X is a halogen (such as Br, Cl, etc.).

[0021] In this invention, the synthesis route of the luminescent material is convenient, and the prepared luminescent material is a narrow-band pure green luminescent material with good solubility, easy purification, and is beneficial for scale-up and industrial production.

[0022] A third aspect of the present invention provides an organic electroluminescent device, comprising a first electrode, a light-emitting layer, and a second electrode sequentially stacked thereon; the light-emitting layer comprises the light-emitting material of the present invention as described above.

[0023] Optionally, the organic electroluminescent device includes a refractive layer, a first electrode, an electron injection layer, an electron transport layer, a light-emitting layer, a hole transport layer, a hole injection layer, and a second electrode, which are stacked sequentially. Specifically, such as Figure 1 As shown, the organic electroluminescent device provided by the present invention includes a refractive layer 8, a first electrode 7, an electron injection layer 6, an electron transport layer 5, a light-emitting layer 4, a hole transport layer 3, a hole injection layer 2, and a second electrode 1, which are stacked sequentially.

[0024] The luminescent layer comprises a host material, an exciton-sensitizing material, and a guest material. The host material comprises a TADF material, the exciton-sensitizing material comprises a complex containing a metal element, and the guest material comprises the luminescent material. The mass ratio of the host material, exciton sensitizing material, and guest material is (60~94.5):(5~30):(0.5~5). For example, it can be 60:5:0.5, 60:15:0.5, 60:30:0.5, 94.5:5:0.5, 94.5:15:0.5, 94.5:30:0.5, 60:5:5, 60:15:5, 60:30:5, 94.5:5:5, 94.5:15:5, or 94.5:30:5, etc. TADF materials refer to materials with thermally activated delayed fluorescence properties. They have a small energy level difference between the first excited singlet state and the first excited triplet state, thus allowing the simultaneous utilization of generated singlet and triplet excitons in the device, making the exciton utilization rate of electroinduced excitons within the device as close to 100% as possible. Compared to traditional fluorescent materials, TADF materials have a higher exciton utilization rate.

[0025] 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-sensitized materials play a role in exciton capture, exciton conversion, and exciton transfer in electroluminescent devices. The luminescent material and exciton-sensitized material shown in formula (1) of this invention are used together to significantly improve problems such as device efficiency, exciton annihilation in the device, and efficiency reduction.

[0026] In this invention, the main material can be a single main material or a dual main material. The dual main material includes a first main material and a second main material, and at least one of the first main material and the second main material is a TADF material.

[0027] The dual-body material is selected from one of the following combinations 1 to 3, but is not limited thereto: Combination 1: Combination 2: Combination 3: .

[0028] The hole injection layer material (i.e., hole injection material) can be at least one of the following materials and their derivatives, or materials obtained by doping or passivation: PEODT:PSS (poly(3,4-ethylenedioxythiophene):poly(styrenesulfonic acid)), HAT-CN (2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzophenanthrene), PANI:PSS (polyaniline:poly(styrenesulfonic acid)), graphene, and C60.

[0029] The hole transport layer material (i.e., the hole transport material) can be at least one of the following materials and their derivatives, or materials obtained by doping or passivation: TFB (poly[(9,9-di-n-octylfluorenyl-2,7-diyl)-alt-(4,4'-(N-(4-n-butyl)phenyl)-diphenylamine)]), PVK (polyvinylcarbazole), PFB ([N,N'-(4-n-butylphenyl)-N,N'-diphenyl-p-phenylenediamine]-[9,9-di-n-octylfluorenyl-2,7-diyl] copolymer), TPD (N,N'-bis(3-methylphenyl)-N,N'-diphenyl-1,1'-biphenyl-4,4'-diamine), TCTA (4,4',4''-tris(carbazole-9-yl)triphenylamine), TAPC (4,4'-cyclohexylbis[N,N-di(4-methylphenyl)aniline]), Poly-TPD (polyTPD), NPB (N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine), CBP (4,4'-bis(9-carbazole)biphenyl).

[0030] The electron transport layer material (i.e., the electron transport material) can be at least one of the following materials and their derivatives, or materials obtained by doping or passivation: Liq (lithium 8-hydroxyphosphate), Alq3 (aluminum 8-hydroxyphosphate), Znq2 (zinc 8-hydroxyphosphate), Beq2 (beryllium octahydroxyquinoline), TPBi (1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene), TSPO1 (diphenyl[4] (triphenylsilyl)phenyl]oxyphosphine), TmPyPB (1,3,5) 3 (3) pyridyl 3 phenylbenzene), BPhen (4,7) Diphenyl 1,10 (Phenanolide).

[0031] The material of the electron injection layer (i.e., the electron injection material) can be at least one of the following materials and their derivatives, as well as materials obtained by doping or passivation: Yb (ytterbium), LiF, lithium oxide, aluminum oxide, titanium oxide, and zinc oxide.

[0032] The material of the first electrode (cathode) includes, but is not limited to, at least one of Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, and ITO (indium tin oxide).

[0033] The material of the second electrode (anode) includes, but is not limited to, at least one of ITO, FTO (fluorine-doped SnO2), AZO (aluminum-doped ZnO), and IZO (indium zinc oxide).

[0034] The material of the refractive layer includes, but is not limited to, one of the following materials: .

[0035] In some embodiments, the thickness of the refractive layer is 10 nm-200 nm (preferably 10 nm-100 nm), the thickness of the first electrode is 1 nm-200 nm (preferably 5 nm-100 nm), the thickness of the electron injection layer is 1 nm-200 nm (preferably 5 nm-100 nm), the thickness of the electron transport layer is 1 nm-200 nm (preferably 5 nm-150 nm, more preferably 10 nm-100 nm), the thickness of the light-emitting layer is 1 nm-200 nm (preferably 10 nm-100 nm, more preferably 20 nm-70 nm), the thickness of the hole transport layer is 1 nm-200 nm (preferably 5 nm-150 nm, more preferably 10 nm-100 nm), the thickness of the hole injection layer is 1 nm-200 nm (preferably 5 nm-50 nm, more preferably 5-20 nm), and the thickness of the second electrode is 1 nm-200 nm.

[0036] A fourth aspect of the present invention provides a method for fabricating the organic electroluminescent device of the present invention as described above, comprising the following steps: Provide a second electrode; An emitting layer and a first electrode are sequentially formed on the second electrode to obtain the organic electroluminescent device.

[0037] Optionally, the preparation method specifically includes the following steps: Provide a second electrode; A hole injection layer, a hole transport layer, and a light-emitting layer are sequentially formed on the second electrode using inkjet printing; an electron transport layer, an electron injection layer, a first electrode, and a refractive layer are sequentially formed on the light-emitting layer using vacuum evaporation.

[0038] Beneficial Effects: The luminescent material provided by this invention is a pure green luminescent material that combines high color purity, high efficiency, high stability, good solubility, and film-forming compatibility. Specifically, this luminescent material is a multi-resonance compound with a rigid multi-resonance molecular framework and exhibits narrow-band green light emission. This invention introduces non-conjugated three-dimensional structural units of triphenylsilane and its derivatives into the structure of the luminescent material. While maintaining the narrow-band pure green light emission characteristics of the boron-based multi-resonance framework, it can improve the morphological stability and thermal stability of the material, and enhance its solubility and solution film-forming properties. Furthermore, it can significantly reduce intermolecular stacking, suppress harmful intermolecular aggregation and aggregation-induced non-radiative decay (i.e., suppress intermolecular stacking, non-radiative transition channels, and aggregation-induced quenching, reducing non-radiative losses). This is beneficial for improving device stability and external quantum efficiency in electroluminescent devices, thereby achieving synergistic optimization of high color purity, high efficiency, and long lifetime. Meanwhile, the luminescent material exhibits better solubility and film-forming compatibility, making it suitable for solution processing and inkjet printing to prepare the luminescent layer of organic electroluminescent devices. This meets the requirements of printing processes for material solubility, film uniformity, and device reliability, thus satisfying the development needs of printed display devices. Using the luminescent material provided by this invention as the guest material for the luminescent layer in the preparation of organic electroluminescent devices enables these devices to possess narrow-band emission, high external quantum efficiency, and significantly extended device lifetime. Attached Figure Description

[0039] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device.

[0040] Figure 2 The electroluminescence spectra of the devices in Application Examples 17, 18 and 26 are shown. Detailed Implementation

[0041] This invention provides a luminescent material, an organic electroluminescent device, and a preparation method thereof. To make the objectives, technical solutions, and effects of this invention clearer and more explicit, the invention is further described in detail below. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.

[0042] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains. The terminology used in this specification is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention.

[0043] In the following embodiments, some symbols have the following meanings: t Bu3PHBF4: Tri-tert-butylphosphine tetrafluoroborate; tBuONa: Sodium tert-butoxide; Pd2(dba)3: Tris(dibenzylideneacetone)dipalladium; S-Phos: 2-Dicyclohexyl(2',6'-dimethoxy-[1,1'-biphenyl]-2-yl)phosphine; Pd(PPh3)4: Tetra(triphenylphosphine)palladium; DMF: N,N-dimethylformamide.

[0044] In the following embodiments, unless otherwise specified, the raw materials and equipment used are all commercially available products.

[0045] Example 1 The synthetic route for compound S1 is as follows:

[0046] Following the above synthetic route, this embodiment provides a method for preparing a luminescent material (i.e., compound S1), comprising the following steps: Under an inert atmosphere, 1,3-dibromo-5-chlorobenzene (22.45 mmol), 2,4,6-trimethylaniline (18.69 mmol), and Pd2(dba)3 (0.37 mmol) were added. t Bu3PHBF4 (1.49 mmol) and t BuONa (37.38 mmol) was dissolved in ultradry toluene (40 mL) and stirred at 110 °C for 10 hours. After cooling to room temperature, the mixture was extracted with dichloromethane, and the organic phases were combined. The organic solvent was removed by vacuum distillation, and the mixture was purified by silica gel column chromatography (eluent: petroleum ether / dichloromethane = 5 / 1, v / v) to give compound S1-1 (yield: 87%).

[0047] Under an inert atmosphere, compound S1-1 (8.65 mmol) was... (20.76 mmol), Pd2(dba)3 (0.26 mmol), S-Phos (0.69 mmol) and t BuONa (34.60 mmol) was added to the reaction flask. Then, ultra-dry xylene (35 mL) was injected. The reaction system was heated and stirred at 120 °C for 12 hours. After cooling to room temperature, the reaction mixture was extracted with dichloromethane and water. The organic phase was collected and dried under vacuum, and then purified by silica gel column chromatography (eluent: petroleum ether / dichloromethane = 4 / 1, v / v) to give compound S1-2 (yield: 82%).

[0048] Under inert gas protection, compound S1-2 (2.80 mmol) was added to a pressure-resistant tube and dissolved in ultra-dry o-dichlorobenzene (15 mL). Excess boron tribromide (16.8 mmol) was added, and the mixture was heated to 220 °C for 24 hours. After the reaction was complete, the mixture was cooled to room temperature and quenched by slow addition of methanol in an ice-water bath, resulting in the precipitation of a large amount of solid. The solid was then filtered under reduced pressure, and the residue was collected and purified by silica gel column chromatography (eluent: petroleum ether / dichloromethane = 4 / 1, v / v) to give compound S1-3 (yield: 65%).

[0049] Under inert gas protection, compound S1-3 (0.96 mmol) was... 1.16 mmol of Pd(PPh3)4 (0.11 mmol) and 1.92 mmol of K2CO3 were mixed in a mixed solvent of toluene, ethanol, and water (toluene:ethanol:water = 2:1:1, volume ratio), and heated to 100 °C for 12 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with dichloromethane and water. The filtrate was then evaporated to dryness. The solution was then purified by silica gel column chromatography (eluent: petroleum ether / dichloromethane = 4 / 1, volume ratio) to obtain the luminescent material, compound S1 (yield: 78%).

[0050] The test data for compound S1 are as follows: The proton NMR data are 1 H NMR (500 MHz, CDCl3) d (ppm): 9.23 (s, 2H), 7.90 (d, J = 7.6 Hz, 2H), 7.64 (d, J = 8.2 Hz, 2H), 7.57–7.49 (m, 6H), 7.48 (d, J =8.3 Hz, 2H), 7.44–7.33 (m, 9H), 7.32 (d, J = 8.3 Hz, 2H), 7.31–7.26 (m, 6H), 7.21 (s, 4H), 6.38 (s, 2H), 2.50 (s, 6H), 1.95 (s, 12H). The carbon NMR data are as follows: 13 CNMR (126 MHz, CDCl 3 ) d(ppm): 157.73, 151.53, 146.28, 145.92, 142.75, 142.67,138.55, 137.55, 137.34, 137.18, 136.10, 135.55, 134.90, 131.05, 130.66,129.45, 128.80, 128.55, 128.22, 128.05, 127.95, 127.88, 127.70, 127.35,124.45, 122.25, 121.52, 115.50, 111.88, 106.19, 102.34, 21.40, 17.72. Mass spectrometry data are MS (MALDI-TOF): m / z 1019.42 [M + ].

[0051] Example 2 Synthetic route of compound S2:

[0052] Following the above synthetic route, this embodiment provides a method for preparing a luminescent material (i.e., compound S2), which is largely the same as in Example 1, except that 2,4,6-trimethylaniline is replaced with [other substance] when preparing compound S2-1. When preparing compound S2-2, Replace with The prepared compound S2 was a pale yellow solid powder, with a yield of 75%.

[0053] The test data for compound S2 are as follows: The proton NMR data are 1 H NMR (500 MHz, CDCl3) d (ppm): 9.22 (s, 2H), 8.10 (d, J = 7.8 Hz, 2H), 7.96 (d, J = 7.6 Hz, 2H), 7.90 (d, J = 7.6 Hz, 2H), 7.66(d, J = 8.2 Hz, 2H), 7.60–7.50 (m, 6H), 7.49 (d, J = 8.3 Hz, 2H), 7.46–7.22 (m,21H), 7.34 (d, J= 8.3 Hz, 2H), 7.21 (s, 4H), 6.39 (s, 2H), 1.95 (s, 12H). The carbon NMR data are: 13 C NMR (126 MHz, CDCl 3 ) d (ppm): 158.00, 151.85, 149.20, 147.15,146.45, 145.98, 143.35, 142.95, 141.15, 139.80, 139.05, 138.40, 137.95,137.60, 137.35, 136.30, 135.85, 135.25, 134.95, 134.40, 131.15, 130.75,129.60, 128.95, 128.70, 128.35, 128.20, 128.05, 127.90, 127.75, 127.60, 127.40, 125.00, 123.20, 121.65, 115.58, 111.98, 106.28, 102.45, 17.75. Mass spectrometry data are MS (MALDI-TOF): m / z 1175.43 [M + ].

[0054] Example 3 Synthetic route of compound S3:

[0055] Following the above synthetic route, this embodiment provides a method for preparing a luminescent material (i.e., compound S3), which is largely the same as in Example 2, except that: when preparing S3-2, [the following is omitted as it is not directly related to the previous sentence] Replace with The prepared compound S3 was a pale yellow solid powder, with a yield of 72%.

[0056] The test data for compound S3 are as follows: The proton NMR data are 1 H NMR (500 MHz, CDCl3) d (ppm): 9.28 (s, 2H), 8.55 (d, J = 8.4 Hz, 2H), 8.36 (d, J = 7.9 Hz, 2H), 8.20 (t, J = 7.6 Hz, 2H), 8.06 (d, J= 8.1 Hz, 2H), 7.96–7.88 (m, 4H), 7.80–7.72 (m, 6H), 7.67 (d, J = 8.3 Hz, 2H), 7.60–7.50 (m, 10H), 7.49–7.38 (m, 9H), 7.37–7.26 (m, 4H), 7.33 (d, J =8.3 Hz, 2H), 7.24–7.12 (m, 6H), 6.40 (s, 2H), 2.06 (s, 12H). The carbon NMR data are as follows: 13 C NMR (126 MHz, CDCl 3 ) d (ppm): 158.00, 151.85, 149.20, 147.15, 146.45,145.98, 143.35, 142.95, 141.15, 139.80, 139.05, 138.40, 137.95, 137.60,137.35, 136.30, 135.85, 135.25, 134.95, 134.40, 131.15, 130.75, 129.60,128.95, 128.70, 128.35, 128.20, 128.05, 127.90, 127.75, 127.60, 127.40, 125.00, 123.20, 121.65, 115.58, 111.98, 106.28, 102.45, 17.74. Mass spectrometry data are MS (MALDI-TOF): m / z 1163.53 [M + ].

[0057] Example 4 Synthetic route of compound S4:

[0058] Following the above synthetic route, this embodiment provides a method for preparing a luminescent material (i.e., compound S4), comprising the following steps: Under an inert atmosphere, (22.20 mmol) 18.50 mmol of DMF and 44.40 mmol of Cs₂CO₃ were dissolved in ultradry DMF (90 mL) and stirred at 80 °C for 24 hours. After cooling to room temperature, the mixture was extracted with dichloromethane, and the organic phases were combined. The organic solvent was removed by vacuum distillation, and the mixture was purified by silica gel column chromatography (eluent: petroleum ether / dichloromethane = 6 / 1, v / v) to give compound S4-1 (yield: 92%).

[0059] Under an inert atmosphere, compound S4-1 (6.22 mmol) was... (6.53 mmol) and Cs2CO3 (12.44 mmol) were dissolved in ultradry DMF (40 mL) and stirred at 150 °C for 24 hours. After cooling to room temperature, the mixture was extracted with dichloromethane, the organic phases were combined, the organic solvent was removed by vacuum distillation, and the mixture was purified by silica gel column chromatography (eluent: petroleum ether / dichloromethane = 5 / 1, v / v) to give compound S4-2 (yield: 88%).

[0060] Under an inert atmosphere, compound S4-2 (5.14 mmol) was dissolved in anhydrous trimethylbenzene (25 mL), cooled to 0 °C, and tert-butyllithium (7.71 mmol) was added dropwise. The mixture was then heated to 60 °C and stirred for 3 h. After cooling back to 0 °C, boron tribromide (20.55 mmol) was added, and the reaction was carried out at room temperature for 2 h. Subsequently, N,N-diisopropylethylamine (41.1 mmol) was added, and the reaction was carried out at 150 °C for 12 h. After cooling to room temperature, the mixture was quenched with methanol, extracted with dichloromethane, and the organic phases were combined. The organic solvent was removed by vacuum distillation, and the mixture was purified by silica gel column chromatography (eluent: petroleum ether / dichloromethane = 5 / 1, v / v) to give compound S4-3 (yield: 38%).

[0061] Under inert gas protection, compound S4-3 (1.26 mmol) was... 1.64 mmol of Pd(PPh3)4 (0.10 mmol) and 2.27 mmol of K2CO3 were mixed in a mixed solvent of toluene, ethanol, and water (toluene:ethanol:water = 2:1:1, volume ratio), and heated to 100 °C for 12 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with dichloromethane and water. The filtrate was then evaporated to dryness. The solution was then purified by silica gel column chromatography (eluent: petroleum ether / dichloromethane = 4 / 1, volume ratio) to give compound S4 (yield: 82%).

[0062] The test data for compound S4 are as follows: The proton NMR data are 1 H NMR (500 MHz, CDCl3) d (ppm): 9.01 (d, J= 1.7 Hz,1H), 9.00 (s, 1H), 8.64 (d, J = 7.5 Hz, 1H), 8.54 (d, J = 7.7 Hz, 1H), 8.46 (s,1H), 8.44 (d, J = 7.9 Hz, 1H), 8.37 (d, J = 1.8 Hz, 1H), 8.36 (s, 1H), 8.23 ​​(s,1H), 8.18 (d, J = 2.0 Hz, 1H), 8.13 (d, J = 8.8 Hz, 1H), 7.96 (d, J = 7.7 Hz, 1H), 7.76 – 7.73 (m, 7H), 7.72 (d, J = 8.2 Hz, 1H), 7.64 (t, J = 7.5 Hz, 1H), 7.60 (t, J = 7.6 Hz, 1H), 7.56 (dd, J = 8.7, 2.1 Hz, 1H), 7.48 (dq, J = 12.1, 7.7, 6.7 Hz, 12H), 1.71 (s, 9H), 1.57 (s, 9H). The carbon NMR data are: 13C NMR (126MHz, CDCl3) δ (ppm): 145.60, 145.05, 144.32, 142.55, 141.70, 141.25, 139.40,138.35, 138.18, 138.05, 136.70, 136.45, 135.75, 135.45, 134.25, 130.25,129.95, 129.42, 129.28, 128.85, 128.25, 128.05, 127.70, 127.15, 126.90,126.78, 125.90, 124.55, 124.48, 123.80, 123.62, 122.45, 121.75, 121.45, 120.75, 120.50, 119.68, 117.25, 116.95, 114.30, 114.12, 109.95, 107.95, 107.20, 34.98, 34.78, 32.22, 31.88. Mass spectrometry data are MS (MALDI-TOF): m / z 953.42 [M + ].

[0063] Example 5 Synthetic route of compound S5:

[0064] Following the above synthetic route, this embodiment provides a method for preparing the luminescent material (i.e., compound S5), which is largely the same as in Example 4, except that: when preparing S5-2, [the following is omitted as the text is incomplete and requires further context]. Replace with The prepared compound S5 was an orange-yellow solid powder with a yield of 76%.

[0065] The test data for compound S5 are as follows: The proton NMR data are 1 H NMR (500 MHz, CDCl3) d (ppm): 9.02 – 8.99 (m, 1H),8.98 (s, 1H), 8.97 (d, J = 8.6 Hz, 1H), 8.78 (d, J = 1.9 Hz, 1H), 8.57 (d, J =1.1 Hz, 1H), 8.53 (dt, J = 7.5, 3.5 Hz, 1H), 8.44 (d, J= 1.1 Hz, 1H), 8.39 (d, J = 1.8 Hz, 1H), 8.25 (d, J = 1.9 Hz, 1H), 8.22 (d, J = 2.1 Hz, 1H), 8.19 (d, J = 8.8 Hz, 1H), 7.98 (dt, J = 7.9, 1.4 Hz, 1H), 7.78 – 7.70 (m, 11H), 7.67 –7.43 (m, 17H), 1.54 (s, 9H), 1.49 (s, 9H). The carbon NMR data are as follows: 13 C NMR (126 MHz, CDCl3) δ (ppm): 145.38, 144.87, 144.16, 142.38, 141.51, 141.09, 139.20,138.21, 138.07, 137.90, 136.50, 136.27, 135.56, 135.26, 134.10, 130.10,129.79, 129.26, 129.17, 128.68, 128.07, 127.92, 127.51, 126.97, 126.71,126.58, 125.70, 124.38, 124.34, 123.59, 123.45, 122.29, 121.55, 121.26, 120.54, 120.29, 119.47, 117.03, 116.78, 114.08, 114.00, 109.75, 107.74, 107.00, 34.97, 34.75, 32.20, 31.86. Mass spectrometry data are MS (MALDI-TOF): m / z 1028.47 [M + ].

[0066] Example 6 Synthetic route of compound S6:

[0067] Following the above synthetic route, this embodiment provides a method for preparing a luminescent material (i.e., compound S6), which is largely the same as in Example 4, except that: when preparing S6-2, [the following is omitted as it is not directly related to the previous sentence] Replace with The prepared compound S6 was an orange-yellow solid powder with a yield of 79%.

[0068] The test data for compound S6 are as follows: The proton NMR data are 1 H NMR (500 MHz, CDCl3) d (ppm): 8.95 (d, J = 8.6 Hz, 1H), 8.88 (d, J = 2.0 Hz, 1H), 8.80 (s, 1H), 8.66 (d, J = 8.3 Hz, 1H), 8.57 (s,1H), 8.50 (d, J = 1.8 Hz, 1H), 8.33–8.24 (m, 3H), 8.20 (d, J = 7.8 Hz, 1H), 8.01 (d, J = 7.7 Hz, 1H), 7.84–7.71 (m, 10H), 7.67–7.60 (m, 3H), 7.56–7.45 (m,12H), 7.41 (t, J = 7.5 Hz, 1H), 1.54 (s, 9H), 1.48 (s, 9H). The carbon NMR data are: 13C NMR (126 MHz, CDCl3) δ (ppm): 146.05, 145.60, 144.95, 144.30, 142.70,141.95, 141.40, 141.10, 139.55, 139.10, 138.60, 138.25, 138.05, 137.85,136.95, 136.70, 136.35, 135.95, 135.60, 135.25, 134.80, 130.25, 130.05,129.85, 129.55, 129.30, 129.18, 128.90, 128.70, 128.35, 128.20, 128.08, 127.95, 127.60, 127.25, 126.95, 126.75, 126.55, 125.85, 124.75, 124.40, 123.85, 123.55, 122.40, 121.65, 120.60, 120.25, 119.55, 117.10, 116.85, 114.20, 114.05, 110.05, 108.10, 107.25, 34.98, 34.78, 32.22, 31.88. Mass spectrometry data are MS (MALDI-TOF): m / z 987.41 [M + ].

[0069] Example 7 This embodiment provides a luminescent material (i.e., compound S7, whose structural formula is...). The preparation method is largely the same as in Example 6, except that: during preparation, [the following is omitted as the text is incomplete and requires further context]. Replace with The prepared compound S7 was an orange-yellow solid powder with a yield of 86%.

[0070] The test data for compound S7 are as follows: The proton NMR data are 1 H NMR (500 MHz, CDCl3) d(ppm): 9.07–8.99 (m, 3H), 8.80 (d, J = 2.0 Hz, 1H), 8.55 (s, 1H), 8.45–8.38 (m, 3H), 8.28 (s, 2H), 8.21(d, J = 2.0 Hz, 1H), 8.10–8.04 (m, 2H), 7.79 (d, J = 7.1 Hz, 2H), 7.74 (t, J= 7.8 Hz, 2H), 7.67–7.64 (m, 12H), 7.61 (t, J = 7.4 Hz, 2H), 7.58–7.53 (m,3H), 7.51–7.47 (m, 2H), 7.47–7.43 (m, 6H), 7.39 (t, J = 7.2 Hz, 9H), 1.55 (s, 9H), 1.49 (s, 9H). The carbon NMR data are as follows: 13 C NMR (126 MHz, CDCl3) δ (ppm): 146.06,145.12, 144.62, 144.56, 144.36, 142.70, 141.66, 140.48, 139.50, 138.66,138.45, 138.22, 137.92, 136.96, 136.45, 134.80, 134.00, 130.22, 129.77,129.44, 128.15, 128.06, 127.84, 127.04, 126.94, 126.86, 126.09, 124.78, 124.43, 123.82, 123.64, 122.37, 121.78, 120.75, 120.48, 119.64, 117.09, 116.99, 114.33, 114.20, 114.09, 109.98, 108.00, 107.36, 35.06, 34.82, 32.18, 31.87. Mass spectrometry data MS (MALDI-TOF): m / z 1246.52 [M + ].

[0071] Example 8 This embodiment provides a luminescent material (i.e., compound S8, whose structural formula is...). The preparation method of ) is largely the same as that of Example 5, except that: during preparation, Replace with The prepared compound S8 was an orange-yellow solid powder with a yield of 88%.

[0072] The test data for compound S8 are as follows: The proton NMR data are 1 H NMR (500 MHz, CDCl3) d (ppm): 9.08 – 8.99 (m, 3H),8.81 (d, J = 2.0 Hz, 1H), 8.56 (s, 1H), 8.46 – 8.39 (m, 3H), 8.29 (s, 2H), 8.22 (d, J = 2.1 Hz, 1H), 8.11 – 8.05 (m, 2H), 7.78 (d, J = 6.9 Hz, 2H), 7.74(t, J = 7.8 Hz, 2H), 7.67 – 7.64 (m, 12H), 7.61 (t, J = 7.4 Hz, 2H), 7.58 –7.53 (m, 3H), 7.51 – 7.47 (m, 2H), 7.47 – 7.43 (m, 6H), 7.39 (t, J = 7.2 Hz, 12H), 1.55 (s, 9H), 1.49 (s, 9H). The carbon NMR data are: 13 C NMR (126 MHz, CDCl3) d (ppm): 146.04, 145.10, 144.59, 144.55, 144.35, 142.67, 141.63, 140.44,139.46, 138.63, 138.43, 138.20, 137.90, 136.93, 136.42, 134.77, 133.96,130.19, 129.74, 129.41, 128.12, 128.03, 127.81, 127.01, 126.91, 126.83,126.06, 124.75, 124.40, 123.79, 123.61, 122.34, 121.75, 120.73, 120.45, 119.61, 117.06, 116.97, 114.30, 114.18, 114.07, 109.96, 107.97, 107.34, 35.06, 34.82, 32.18, 31.87. Mass spectrometry data are MS (MALDI-TOF): m / z 1286.55 [M + ].

[0073] Example 9 Synthetic route of compound S9:

[0074] Following the above synthetic route, this embodiment provides a method for preparing a luminescent material (i.e., compound S9), which is largely the same as in Example 4, except that: when preparing S9-1 and S9-2, [the following method is used]. and Replace all with The prepared compound S9 was an orange-yellow solid powder with a yield of 74%.

[0075] The test data for compound S9 are as follows: The proton NMR data are 1 H NMR (500 MHz, CDCl3) d (ppm): 8.98 (d, J = 2.0 Hz, 1H), 8.86 (d, J = 8.4 Hz, 1H), 8.78 (s, 1H), 8.64 (dd, J = 8.4, 2.0 Hz, 1H),8.56 (s, 1H), 8.45 (d, J = 1.8 Hz, 1H), 8.32–8.25 (m, 2H), 8.12 (d, J = 7.7 Hz, 1H), 7.82 (d, J = 7.6 Hz, 2H), 7.76 (t, J = 7.6 Hz, 2H), 7.71–7.64 (m, 6H), 7.63–7.54 (m, 12H), 7.53–7.45 (m, 8H), 7.44–7.34 (m, 10H). The carbon NMR data are as follows: 13 C NMR (126 MHz, CDCl3) d(ppm): 146.22, 145.48, 144.92, 144.60, 143.95,142.80, 141.92, 141.35, 140.60, 139.75, 139.05, 138.72, 138.40, 138.18,137.98, 137.35, 136.92, 136.55, 135.90, 135.55, 135.10, 134.72, 134.10,129.85, 129.45, 129.30, 128.60, 128.35, 128.18, 127.92, 127.70, 127.35, 127.10, 126.92, 126.75, 126.55, 124.85, 124.45, 123.85, 123.60, 122.45, 121.80, 120.80, 120.50, 119.70, 117.20, 116.95, 114.35, 114.15, 110.05, 108.10, 107.30. Mass spectrometry data are MS (MALDI-TOF): m / z 1081.39 [M + ].

[0076] Example 10 This embodiment provides a luminescent material (i.e., compound S10, whose structural formula is: The preparation method of ) is largely the same as that of Example 9, except that: during preparation, Replace with The prepared compound S10 was an orange solid powder with a yield of 82%.

[0077] The test data for compound S10 are as follows: The proton NMR data are 1 H NMR (500 MHz, CDCl3) δ (ppm): 9.00 (d, J = 2.1 Hz, 1H), 8.88 (d, J = 8.5 Hz, 1H), 8.80 (s, 1H), 8.66 (dd, J = 8.5, 2.1 Hz, 1H),8.57 (s, 1H), 8.46 (d, J = 1.9 Hz, 1H), 8.33–8.26 (m, 2H), 8.13 (d, J = 7.8 Hz, 1H), 7.83 (d, J= 7.6 Hz, 2H), 7.77 (t, J = 7.7 Hz, 2H), 7.72–7.64 (m, 6H), 7.63–7.54 (m, 22H), 7.53–7.44 (m, 12H), 7.43–7.33 (m, 10H). The carbon NMR data are as follows: 13 C NMR (126 MHz, CDCl3) δ (ppm): 146.25, 145.52, 144.96, 144.64, 144.00,142.85, 141.98, 140.68, 139.82, 138.78, 138.48, 138.25, 138.02, 137.42,136.62, 135.98, 135.62, 135.18, 134.80, 134.18, 129.90, 129.68, 129.50,129.35, 128.90, 128.65, 128.40, 128.22, 128.10, 127.98, 127.75, 127.42, 127.18, 126.98, 126.80, 126.60, 124.90, 123.90, 123.65, 122.50, 121.85, 120.85, 120.55, 119.75, 117.25, 117.00, 114.40, 114.20, 110.10, 108.15, 107.35. Mass spectrometry data are MS (MALDI-TOF): m / z 1340.46 [M + ].

[0078] Example 11 Synthetic route of compound S11:

[0079] Following the above synthetic route, this embodiment provides a method for preparing a luminescent material (i.e., compound S11), which is largely the same as in Example 9, except that: when preparing S11-2, [the following is omitted as it is not directly related to the previous sentence] Replace with The prepared compound S11 was an orange-yellow solid powder with a yield of 74%.

[0080] The test data for compound S11 are as follows: The proton NMR data are 1 H NMR (500 MHz, CDCl3) δ (ppm): 9.10–9.01 (m, 3H),8.83 (d, J= 2.0 Hz, 1H), 8.58 (s, 1H), 8.47–8.40 (m, 3H), 8.30 (s, 2H), 8.23(d, J = 2.1 Hz, 1H), 8.12–8.05 (m, 2H), 7.79 (d, J = 7.6 Hz, 2H), 7.74 (t, J =7.8 Hz, 2H), 7.68–7.60 (m, 12H), 7.58–7.48 (m, 10H), 7.47–7.36 (m, 7H), 1.36 (s, 18H), 1.31 (s, 18H). The carbon NMR data are as follows: 13 C NMR (126 MHz, CDCl3) δ (ppm):146.10, 145.25, 144.75, 144.58, 144.40, 142.80, 141.70, 140.55, 139.60,138.75, 138.55, 138.30, 138.05, 137.15, 136.65, 135.10, 134.30, 130.35,129.95, 129.55, 128.30, 128.15, 127.95, 127.20, 127.05, 126.95, 126.20,124.90, 124.55, 123.95, 123.70, 122.50, 121.90, 120.90, 120.60, 119.80, 117.30, 117.10, 114.45, 114.25, 110.10, 108.10, 107.45, 35.20, 34.95, 31.90, 31.55. Mass spectrometry data are MS (MALDI-TOF): m / z 1292.63 [M + ].

[0081] Example 12 This embodiment provides a luminescent material (i.e., compound S12, whose structural formula is...). The preparation method of ) is largely the same as that of Example 11, except that: during preparation, Replace with The prepared compound S12 was an orange-yellow solid powder with a yield of 76%.

[0082] The test data for compound S12 are as follows: The proton NMR data are 1H NMR (500 MHz, CDCl3) d (ppm): 9.08–8.99 (m, 3H),8.82 (d, J = 2.0 Hz, 1H), 8.57 (s, 1H), 8.46–8.39 (m, 3H), 8.30 (s, 2H), 8.22(d, J = 2.0 Hz, 1H), 8.11–8.05 (m, 2H), 7.80 (d, J = 7.7 Hz, 2H), 7.75 (t, J =7.8 Hz, 2H), 7.69–7.62 (m, 6H), 7.56–7.50 (m, 4H), 1.36 (s, 18H), 1.31 (s, 18H). The carbon NMR data are as follows: 13 C NMR (126 MHz, CDCl3) δ (ppm): 146.10, 145.25,144.75, 144.58, 144.40, 142.80, 141.70, 140.55, 139.60, 138.75, 138.55,138.30, 138.05, 137.15, 136.65, 135.10, 134.30, 130.35, 129.95, 129.55,128.30, 128.15, 127.95, 127.20, 127.05, 126.95, 126.20, 124.90, 124.55, 123.95, 123.70, 122.50, 121.90, 120.90, 120.60, 119.80, 117.30, 117.10, 114.45, 114.25, 110.10, 108.10, 107.45, 35.20, 34.95, 31.90, 31.55. Mass spectrometry data are MS (MALDI-TOF): m / z 1311.75 [M + ].

[0083] Example 13 Synthetic route of compound S13:

[0084] Following the above synthetic route, this embodiment provides a method for preparing a luminescent material (i.e., compound S13), which is largely the same as in Example 12, except that: when preparing S13-1, [the following is omitted as it is not directly related to the previous sentence] Replace with The prepared compound S13 was an orange-yellow solid powder with a yield of 76%.

[0085] The test data for compound S13 are as follows: The proton NMR data are 1 H NMR (500 MHz, CDCl3) δ (ppm): 9.10–9.02 (m, 3H),8.83 (d, J = 2.0 Hz, 1H), 8.59 (s, 1H), 8.48–8.41 (m, 3H), 8.31 (s, 2H), 8.23(d, J = 2.0 Hz, 1H), 8.12–8.06 (m, 2H), 7.80 (d, J = 7.8 Hz, 2H), 7.73 (t, J =7.8 Hz, 2H), 7.68–7.62 (m, 4H), 7.56–7.50 (m, 3H), 1.36 (s, 18H), 1.31 (s, 18H). The carbon NMR data are as follows: 13 C NMR (126 MHz, CDCl3) δ (ppm):146.08, 145.24,144.74, 144.56, 144.38, 142.82, 141.68, 140.54, 139.58, 138.74, 138.54,138.28, 138.02, 137.14, 136.64, 135.08, 134.28, 130.34, 129.94, 129.54,128.28, 128.14, 127.94, 127.18, 127.03, 126.94, 126.20, 124.88, 124.54, 123.94, 123.68, 122.48, 121.88, 120.88, 120.58, 119.78, 117.28, 117.08, 114.44, 114.24, 110.08, 108.08, 107.44, 35.18, 34.93, 31.88, 31.53. Mass spectrometry data are MS (MALDI-TOF): m / z 1271.73 [M + ].

[0086] Example 14 This embodiment provides a luminescent material (i.e., compound S14, whose structural formula is...). The preparation method of ) is largely the same as that of Example 13, except that: during preparation, Replace with The prepared compound S14 was an orange-yellow solid powder with a yield of 78%.

[0087] The test data for compound S14 are as follows: The proton NMR data are 1 H NMR (500 MHz, CDCl3) δ (ppm): 9.12–9.03 (m, 3H),8.84 (d, J = 2.0 Hz, 1H), 8.60 (s, 1H), 8.49–8.41 (m, 3H), 8.32 (s, 2H), 8.24(d, J = 2.1 Hz, 1H), 8.13–8.06 (m, 2H), 7.86 (d, J =8.2 Hz, 2H), 7.79 (d, J =7.7 Hz, 2H), 7.74 (t, J = 7.8 Hz, 2H), 7.69–7.62 (m, 10H), 7.58–7.49 (m, 8H), 7.47–7.41 (m, 6H), 1.36 (s, 18H), 1.31 (s, 18H). The carbon NMR data are: 13 C NMR (126MHz, CDCl3) δ (ppm): 146.12, 145.28, 144.78, 144.60, 144.42, 142.86, 141.72,140.58, 139.62, 138.78, 138.58, 138.32, 138.06, 137.18, 136.68, 135.12,134.32, 130.38, 129.98, 129.58, 128.32, 128.18, 127.98, 127.22, 127.07,126.98, 126.24, 124.92, 124.58, 123.98, 123.72, 122.52, 121.92, 120.92, 120.62, 119.82, 117.32, 117.12, 114.48, 114.28, 110.12, 108.12, 107.48, 35.20, 34.95, 31.90, 31.55. Mass spectrometry data are MS (MALDI-TOF): m / z 1252.60 [M + ].

[0088] Example 15 Synthetic route of compound S15:

[0089] Following the above synthetic route, this embodiment provides a method for preparing a luminescent material (i.e., compound S15), comprising the following steps: Under an inert atmosphere, (12.35 mmol) (16.06 mmol), Pd2(dba)3 (0.25 mmol), t Bu3PHBF4 (0.99 mmol) and t BuONa (24.70 mmol) was dissolved in ultradry toluene (30 mL) and stirred at 110 °C for 8 hours. After cooling to room temperature, the mixture was extracted with dichloromethane, and the organic phases were combined. The organic solvent was removed by vacuum distillation, and the mixture was purified by silica gel column chromatography (eluent: petroleum ether / dichloromethane = 5 / 1, v / v) to give compound S15-1 (yield: 88%).

[0090] Under an inert atmosphere, compound S15-1 (9.68 mmol) was... (6.45 mmol), Pd2(dba)3 (0.13 mmol), t Bu3PHBF4 (0.52 mmol) and t BuONa (12.90 mmol) was added to the reaction flask. Then, ultra-dry xylene (25 mL) was injected. The reaction system was heated and stirred at 100 °C for 10 hours. After cooling to room temperature, the reaction mixture was extracted with dichloromethane and water. The organic phase was collected and dried under vacuum, and then purified by silica gel column chromatography (eluent: petroleum ether / dichloromethane = 4 / 1, v / v) to give compound S15-2 (yield: 74%).

[0091] Under an inert atmosphere, compound S15-2 (4.64 mmol) was... (2.10 mmol), Pd2(dba)3 (0.06 mmol), t Bu3PHBF4 (0.17 mmol) and tBuONa (4.22 mmol) was added to the reaction flask. Then, ultra-dry xylene (20 mL) was injected. The reaction system was heated and stirred at 110 °C for 12 hours. After cooling to room temperature, the reaction mixture was extracted with dichloromethane and water. The organic phase was collected and dried under vacuum, and then purified by silica gel column chromatography (eluent: petroleum ether / dichloromethane = 4 / 1, v / v) to give compound S15-3 (yield: 68%).

[0092] Under inert gas protection, compound S15-3 (1.40 mmol) was added to a pressure-resistant tube and dissolved in ultra-dry o-dichlorobenzene (10 mL). Excess boron tribromide (19.6 mmol) was added, and the mixture was heated to 220 °C for 36 hours. After the reaction was complete, the mixture was cooled to room temperature and quenched by slow addition of methanol in an ice-water bath, resulting in the precipitation of a large amount of solid. The solid was then filtered under reduced pressure, and the residue was collected and purified by silica gel column chromatography (eluent: petroleum ether / dichloromethane = 3 / 1, v / v) to give compound S15-4 (yield: 76%).

[0093] Under inert gas protection, compound S15-4 (0.93 mmol) was... 1.21 mmol of Pd(PPh3)4 (0.10 mmol) and 1.88 mmol of K2CO3 were mixed in a mixed solvent of toluene, ethanol, and water (toluene:ethanol:water = 2:1:1, volume ratio), and heated to 100 °C for 12 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with dichloromethane and water. The filtrate was then evaporated to dryness. The solution was then purified by silica gel column chromatography (eluent: petroleum ether / dichloromethane = 3 / 1, volume ratio) to give compound S15 (yield: 83%, pale yellow solid powder).

[0094] The test data for compound S15 are as follows: The proton NMR data are 1 H NMR (500 MHz, CDCl3) d (ppm): 10.95 (s, 1H), 9.69 (s, 2H), 7.93 (d, J = 7.6 Hz, 2H), 7.62 (d, J = 8.0 Hz, 2H), 7.53 (d, J = 6.5Hz, 18H), 7.51 – 7.45 (m, 8H), 7.44 – 7.29 (m, 26H), 7.19 (t, J = 7.8 Hz, 2H), 7.07 (d, J= 7.6 Hz, 4H), 6.31 (s, 2H), 6.29 (s, 2H), 5.78 (s, 1H), 2.01 (s, 12H), 1.86 (s, 12H). The carbon NMR data are: 13 C NMR (126 MHz, CDCl3) d (ppm): 158.40,152.32, 149.30, 146.55, 146.18, 144.15, 143.05, 142.42, 140.30, 139.30,138.35, 137.45, 136.62, 136.10, 135.55, 134.90, 134.30, 133.95, 130.05,129.78, 129.45, 129.25, 128.90, 128.55, 128.30, 128.22, 128.15, 128.05,125.55, 125.05, 122.40, 121.85, 119.55, 116.65, 116.00, 112.05, 106.35, 103.55, 103.05, 99.60, 18.05, 17.75. Mass spectrometry data are MS (MALDI-TOF): m / z 1756.65 [M + ].

[0095] Example 16 This embodiment provides a luminescent material (i.e., compound S16, whose structural formula is: The preparation method of ) is largely the same as that of Example 15, except that: during preparation, Replace with The prepared compound S16 was a pale yellow solid powder with a yield of 78%.

[0096] The test data for compound S16 are as follows: The proton NMR data are 1 H NMR (500 MHz, CDCl3) d (ppm): 10.95 (s, 1H), 9.69 (s, 2H), 7.93 (d, J = 7.6 Hz, 2H), 7.62 (d, J = 8.0 Hz, 2H), 7.53 (t, J = 7.7Hz, 2H), 7.44 – 7.39 (m, 2H), 7.37 (d, J= 6.5 Hz, 4H), 7.33 (t, J = 7.4 Hz, 2H), 7.28 (d, J = 1.8 Hz, 2H), 7.19 (t, J = 7.7 Hz, 2H), 7.07 (d, J = 7.7 Hz, 4H), 6.31 (s, 2H), 6.29 (s, 2H), 5.78 (s, 1H), 2.01 (s, 12H), 1.86 (s, 12H). The carbon NMR data are as follows: 13 C NMR (126 MHz, CDCl3) d (ppm): 158.42, 152.34, 149.32,146.53, 146.20, 143.06, 142.30, 140.32, 139.32, 138.37, 137.47, 136.60,136.02, 135.82, 135.30, 134.75, 134.10, 129.98, 129.50, 129.22, 128.92,128.57, 128.32, 128.25, 127.85, 127.65, 127.45, 125.57, 125.07, 122.42, 121.87, 119.57, 116.67, 116.02, 112.07, 106.37, 103.56, 103.06, 99.62, 18.06, 17.76. Mass spectrometry data are MS (MALDI-TOF): m / z 1793.89 [M + ].

[0097] Example 17 This embodiment describes a luminescent material (i.e., compound S17, whose structural formula is...). The preparation method of ) is largely the same as that of Example 15, except that: during preparation, Replace with The prepared compound S17 was a pale yellow solid powder, with a yield of 74%.

[0098] Test data for compound S17: The proton NMR data are 1 H NMR (500 MHz, CDCl3) d (ppm): 10.88 (s, 1H), 9.61 (s, 2H), 7.88 (d, J= 7.6 Hz, 2H), 7.56 (d, J = 8.1 Hz, 2H), 7.50 (d, J = 6.5Hz, 18H), 7.48 – 7.42 (m, 8H), 7.41 – 7.27 (m, 26H), 7.15 (t, J = 7.7 Hz, 2H), 7.03 (d, J = 7.6 Hz, 4H), 6.27 (s, 2H), 6.26 (s, 2H), 5.73 (s, 1H), 1.97 (s, 12H), 1.83 (s, 12H). The carbon NMR data are as follows: 13 C NMR (126 MHz, CDCl3) d (ppm): 157.98,151.95, 148.95, 146.07, 145.73, 143.65, 142.53, 141.89, 139.84, 138.86,137.89, 136.98, 136.38, 135.43, 134.69, 134.07, 129.80, 129.56, 129.20,129.08, 128.71, 128.32, 128.11, 128.04, 127.98, 127.92, 125.10, 124.60,122.06, 121.47, 119.15, 116.27, 115.62, 111.79, 106.03, 103.23, 102.74, 99.27, 17.75, 17.45. Mass spectrometry data are MS (MALDI-TOF): m / z 1724.70 [M + ].

[0099] Example 18 This embodiment provides a luminescent material (i.e., compound S18, whose structural formula is...). The preparation method of ) is largely the same as that of Example 17, except that: during preparation, Replace with The prepared compound S18 was a pale yellow solid powder, with a yield of 74%.

[0100] The test data for compound S18 are as follows: The proton NMR data are 1 H NMR (500 MHz, CDCl3) d(ppm): 10.88 (s, 1H), 9.61 (s, 2H), 7.88 (d, J = 7.6 Hz, 2H), 7.56 (d, J = 8.1 Hz, 2H), 7.50 (t, J = 7.7Hz, 2H), 7.41 – 7.36 (m, 2H), 7.34 (d, J = 6.5 Hz, 4H), 7.30 (t, J = 7.4 Hz, 2H), 7.25 (d, J = 1.8 Hz, 2H), 7.15 (t, J = 7.6 Hz, 2H), 7.03 (d, J = 7.7 Hz, 4H), 6.27 (s, 2H), 6.26 (s, 2H), 5.73 (s, 1H), 1.97 (s, 12H), 1.83 (s, 12H). The carbon NMR data are: 13 C NMR (126 MHz, CDCl3) d (ppm): 158.01, 151.98, 148.98,146.05, 145.76, 142.56, 141.75, 139.87, 138.88, 137.91, 137.00, 136.12,135.94, 135.75, 135.02, 134.52, 133.86, 129.83, 129.23, 129.06, 128.74,128.34, 128.14, 128.08, 127.61, 127.42, 127.23, 125.12, 124.62, 122.09, 121.49, 119.18, 116.29, 115.65, 111.81, 106.06, 103.25, 102.76, 99.30, 17.77, 17.48. Mass spectrometry data are MS (MALDI-TOF): m / z 1762.94 [M + ].

[0101] Example 19 Synthetic route of compound S19:

[0102] Following the above synthetic route, this embodiment provides a method for preparing a luminescent material (i.e., compound S19), comprising the following steps: Under an inert atmosphere, (16.10 mmol) 17.71 mmol of DMF and 28.98 mmol of Cs₂CO₃ were dissolved in ultradry DMF (40 mL) and stirred at 150 °C for 24 hours. After cooling to room temperature, the mixture was extracted with dichloromethane, and the organic phases were combined. The organic solvent was removed by vacuum distillation, and the mixture was purified by silica gel column chromatography (eluent: petroleum ether / dichloromethane = 5 / 1, v / v) to give compound S19-1 (yield: 94%).

[0103] Under an inert atmosphere, compound S19-1 (14.64 mmol) was... (6.10 mmol), Pd2(dba)3 (0.12 mmol), t Bu3PHBF4 (0.49 mmol) and t BuONa (24.4 mmol) was added to the reaction flask. Then, ultra-dry xylene (25 mL) was injected. The reaction system was heated and stirred at 110 °C for 12 hours. After cooling to room temperature, the reaction mixture was extracted with dichloromethane and water. The organic phase was collected and dried under vacuum, and then purified by silica gel column chromatography (eluent: petroleum ether / dichloromethane = 4 / 1, v / v) to give compound S19-2 (yield: 66%).

[0104] Under inert gas protection, compound S19-2 (5.33 mmol) was added to a pressure-resistant tube and dissolved in ultra-dry o-dichlorobenzene (30 mL). Excess boron tribromide (74.62 mmol) was added, and the mixture was heated to 220 °C for 36 hours. After the reaction was complete, the mixture was cooled to room temperature and quenched by slow addition of methanol in an ice-water bath, resulting in the precipitation of a large amount of solid. The solid was then filtered under reduced pressure, and the residue was collected and purified by silica gel column chromatography (eluent: petroleum ether / dichloromethane = 3 / 1, v / v) to give compound S19-3 (yield: 70%).

[0105] Under inert gas protection, compound S19-3 (1.93 mmol) was... 2.31 mmol of Pd(PPh3)4 (0.10 mmol) and 3.88 mmol of K2CO3 were mixed in a mixed solvent of toluene, ethanol, and water (toluene:ethanol:water = 2:1:1, volume ratio), and heated to 100 °C for 12 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with dichloromethane and water. The filtrate was then evaporated to dryness. The solution was then purified by silica gel column chromatography (eluent: petroleum ether / dichloromethane = 5 / 2, volume ratio) to give compound S19 (yield: 83%, pale yellow solid powder).

[0106] The test data for compound S19 are as follows: The proton NMR data are 1 H NMR (500 MHz, CDCl3) d (ppm): 10.90 (s, 1H), 9.62 (s, 2H), 7.98 (d, J = 7.7 Hz, 2H), 7.86 (d, J = 7.9 Hz, 2H), 7.82–7.74 (m, 8H), 7.72–7.60 (m, 10H), 7.55–7.47 (m, 18H), 7.46–7.28 (m, 26H), 7.20 (t, J = 6.8Hz, 2H), 7.05 (d, J = 7.7 Hz, 4H), 6.28 (s, 2H), 6.26 (s, 2H), 5.74 (s, 1H), 2.02 (s, 12H). The carbon NMR data are as follows: 13 C NMR (126 MHz, CDCl3) d (ppm): 158.05,152.00, 149.00, 146.20, 145.90, 144.10, 143.10, 142.50, 142.00, 140.10,139.90, 139.10, 138.90, 138.10, 137.90, 137.30, 136.95, 136.40, 135.90,135.50, 134.90, 134.40, 134.00, 133.60, 133.10, 130.00, 129.80, 129.55,129.20, 129.10, 128.75, 128.35, 128.15, 128.05, 127.98, 127.92, 125.20, 124.80, 124.30, 123.90, 122.10, 121.55, 119.20, 116.30, 115.70, 111.85, 106.10, 103.30, 102.80, 99.30, 65.2, 18.0. Mass spectrometry data are MS (MALDI-TOF): m / z 1812.71 [M + ].

[0107] Example 20 This embodiment provides a luminescent material (i.e., compound S20, whose structural formula is...). The preparation method of ) is largely the same as that of Example 19, except that: during preparation, Replace with The prepared compound S20 was a pale yellow solid powder with a yield of 70%.

[0108] The test data for compound S20 are as follows: The proton NMR data are 1 H NMR (500 MHz, CDCl3) d (ppm): 10.88 (s, 1H), 9.64 (s, 2H), 7.97 (d, J = 7.5 Hz, 2H), 7.88 (d, J = 7.9 Hz, 2H), 7.80–7.72 (m, 8H), 7.70–7.60 (m, 10H), 7.55–7.47 (m, 18H), 7.44–7.28 (m, 18H), 7.18 (t, J = 7.3Hz, 2H), 7.03 (d, J = 6.7 Hz, 4H), 6.29 (s, 2H), 6.23 (s, 2H), 5.73 (s, 1H), 2.00 (s, 12H). The carbon NMR data are: 13 C NMR (126 MHz, CDCl3) d(ppm): 158.08,152.02, 149.05, 146.25, 145.92, 144.15, 143.12, 142.55, 142.05, 140.15,139.95, 139.18, 138.98, 138.20, 137.98, 137.35, 137.00, 136.48, 136.00,135.55, 134.95, 134.45, 134.05, 133.65, 133.15, 130.05, 129.85, 129.60,129.25, 129.12, 128.80, 128.40, 128.20, 128.08, 128.00, 127.95, 125.25, 124.85, 124.35, 123.95, 122.15, 121.58, 119.25, 116.35, 115.75, 111.90, 106.12, 103.32, 102.82, 99.32, 65.2, 18.0. Mass spectrometry data are MS (MALDI-TOF): m / z 1732.65 [M + ].

[0109] Example 21 This embodiment provides a luminescent material (i.e., compound S21, whose structural formula is...). The preparation method of ) is largely the same as that of Example 20, except that: during preparation, Replace with The prepared compound S21 was a pale yellow solid powder with a yield of 74%.

[0110] The test data for compound S21 are as follows: The proton NMR data are 1 H NMR (500 MHz, CDCl3) d (ppm): 10.88 (s, 1H), 9.64(s, 2H), 7.97 (d, J = 7.5 Hz, 2H), 7.88 (d, J = 8.2 Hz, 2H), 7.80–7.72 (m,4H), 7.70–7.60 (m, 4H), 7.55–7.47 (m, 4H), 7.44–7.28 (m, 4H), 7.18 (t, J = 7.2Hz, 2H), 7.03 (d, J= 6.5 Hz, 4H), 6.29 (s, 2H), 6.23 (s, 2H), 5.73 (s, 1H), 2.00 (s, 12H). The carbon NMR data are: 13 C NMR (126 MHz, CDCl3) d (ppm): 158.08,152.02, 149.05, 146.25, 145.92, 144.15, 143.12, 142.55, 142.05, 140.15,139.95, 139.18, 138.98, 138.20, 137.98, 137.35, 137.00, 136.48, 136.00,135.55, 134.95, 134.45, 134.05, 133.65, 133.15, 130.05, 129.85, 129.60,129.25, 129.12, 128.80, 128.40, 128.20, 128.08, 128.00, 127.95, 125.25, 124.85, 124.35, 123.95, 122.15, 121.58, 119.25, 116.35, 115.75, 111.90, 106.12, 103.32, 102.82, 99.32, 65.2, 18.2. Mass spectrometry data are MS (MALDI-TOF): m / z 1770.88 [M + ].

[0111] Example 22 This embodiment provides a luminescent material (i.e., compound S22, whose structural formula is...). The preparation method of ) is largely the same as that of Example 19, except that: during preparation, the selected ) Replace with The prepared compound S22 was a pale yellow solid powder with a yield of 70%.

[0112] The test data for compound S22 are as follows: The proton NMR data are 1 H NMR (500 MHz, CDCl3) d (ppm):10.92 (s, 1H), 9.68 (s, 2H), 7.97 (d, J = 7.5 Hz, 2H), 7.64 (d, J = 8.1 Hz, 2H), 7.63 (d, J= 8.4Hz, 8H), 7.30 (d, J = 8.4 Hz, 8H), 7.55–7.47 (m, 18H), 7.46–7.38 (m, 12H), 7.44 (d, J = 8.3 Hz, 4H), 7.36 (d, J = 8.3 Hz, 4H), 7.44–7.29 (m, 10H), 7.18(t, J = 7.6 Hz, 2H), 7.06 (d, J = 7.6 Hz, 4H), 6.33 (s, 2H), 6.28 (s, 2H), 5.76 (s, 1H), 2.01 (s, 12H), 1.33 (s, 36H). The carbon NMR data are as follows: 13 C NMR (126 MHz, CDCl3) d (ppm): 158.30, 152.15, 149.25, 146.50, 146.10, 144.05, 143.00,142.35, 141.60, 140.20, 139.25, 138.40, 137.50, 136.70, 136.15, 135.70,135.10, 134.60, 134.15, 130.10, 129.85, 129.55, 129.30, 129.05, 128.85,128.60, 128.40, 128.28, 128.18, 128.08, 127.98, 125.60, 125.10, 122.35, 121.80, 119.55, 116.70, 116.05, 112.10, 106.40, 103.55, 103.05, 99.60, 34.8, 31.5, 18.05, 17.75. Mass spectrometry data are MS (MALDI-TOF): m / z 2011.96 [M + ].

[0113] Example 23 This embodiment provides a luminescent material (i.e., compound S23, whose structural formula is...). The preparation method of ) is largely the same as that of Example 22, except that: during preparation, Replace with The prepared compound S23 was a pale yellow solid powder, with a yield of 68%.

[0114] The test data for compound S23 are as follows: The proton NMR data are 1 H NMR (500 MHz, CDCl3) d (ppm): 1 H NMR (500 MHz, CDCl3) d (ppm):10.92 (s, 1H), 9.68 (s, 2H), 7.97 (d, J = 7.5 Hz, 2H), 7.64 (d, J = 8.1 Hz, 2H), 7.63 (d, J = 8.4 Hz, 8H), 7.30 (d, J = 8.4 Hz, 8H), 7.55–7.48 (m,4H), 7.18 (t, J = 7.6 Hz, 2H), 7.06 (d, J = 7.6 Hz, 4H), 6.33 (s, 2H), 6.28 (s, 2H), 5.76 (s, 1H), 2.01 (s, 12H), 1.33 (s, 36H). The carbon NMR data are as follows: 13 C NMR (126MHz, CDCl3) d (ppm): 158.30, 152.15, 149.25, 146.50, 146.10, 144.05, 143.00,142.35, 141.60, 140.20, 139.25, 138.40, 137.50, 136.70, 136.15, 135.70,135.10, 134.60, 134.15, 130.10, 129.85, 129.55, 129.30, 129.05, 128.85,128.60, 128.40, 128.28, 128.18, 128.08, 127.98, 125.60, 125.10, 122.35, 121.80, 119.55, 116.70, 116.05, 112.10, 106.40, 103.55, 103.05, 99.60, 34.8, 31.5, 18.05, 17.75. Mass spectrometry data are MS (MALDI-TOF): m / z 2051.20 [M + ].

[0115] Example 24 This embodiment provides a luminescent material (i.e., compound S24, whose structural formula is...). The preparation method of ) is largely the same as that of Example 19, except that: during preparation, the selected ) Replace with The prepared compound S24 was a pale yellow solid powder with a yield of 66%.

[0116] The test data for compound S24 are as follows: The proton NMR data are 1 H NMR (500 MHz, CDCl3) d (ppm): 10.86 (s, 1H), 9.63 (s, 2H), 8.04 (d, J = 7.6 Hz, 2H), 7.92 (d, J = 8.2 Hz, 2H), 7.86–7.78 (m, 8H), 7.74–7.63 (m, 10H), 7.56–7.48 (m, 18H), 7.45–7.28 (m, 26H), 7.18 (t, J = 7.1Hz, 2H), 7.05 (d, J = 6.5 Hz, 4H), 6.32 (s, 2H), 6.20 (s, 2H), 5.72 (s, 1H), 2.03 (s, 12H). The carbon NMR data are as follows: 13 C NMR (126 MHz, CDCl3) d(ppm): 158.10,152.05, 149.10, 146.30, 145.95, 144.20, 143.18, 142.60, 142.10, 140.20,140.00, 139.25, 139.05, 138.28, 138.05, 137.42, 137.05, 136.55, 136.05,135.60, 135.02, 134.50, 134.10, 133.70, 133.20, 130.10, 129.90, 129.65,129.30, 129.15, 128.85, 128.45, 128.25, 128.10, 128.02, 127.98, 125.30, 124.90, 124.40, 124.00, 122.20, 121.60, 119.30, 116.40, 115.80, 111.95, 106.15, 103.35, 102.85, 99.35, 65.1, 18.0. Mass spectrometry data are MS (MALDI-TOF): m / z 1876.65 [M + ].

[0117] Example 25 This embodiment provides a luminescent material (i.e., compound S25, whose structural formula is...). The preparation method of ) is largely the same as that of Example 24, except that: during preparation, Replace with The prepared compound S25 was a pale yellow solid powder, with a yield of 68%.

[0118] The test data for compound S25 are as follows: The proton NMR data are 1 H NMR (500 MHz, CDCl3) d (ppm): 10.86 (s, 1H), 9.63 (s, 2H), 8.03 (d, J = 7.8 Hz, 2H), 7.93 (d, J = 8.3 Hz, 2H), 7.86–7.78 (m, 4H),7.74–7.63 (m, 8H), 7.56–7.48 (m, 6H), 7.45–7.28 (m, 6H),7.18 (t, J = 7.1 Hz, 2H), 7.03 (d, J= 5.5 Hz, 4H), 6.30 (s, 2H), 6.22 (s, 2H), 5.72 (s, 1H), 2.00 (s, 12H). The carbon NMR data are: 13 C NMR (126 MHz, CDCl3) d (ppm): 158.10, 152.05,149.10, 146.30, 145.95, 144.20, 143.18, 142.60, 142.10, 140.20, 140.00,139.25, 139.05, 138.28, 138.05, 137.42, 137.05, 136.55, 136.05, 135.60,135.02, 134.50, 134.10, 133.70, 133.20, 130.10, 129.90, 129.65, 129.30,129.15, 128.85, 128.45, 128.25, 128.10, 128.02, 127.98, 125.30, 124.90, 124.40, 124.00, 122.20, 121.60, 119.30, 116.40, 115.80, 111.95, 106.15, 103.35, 102.85, 99.35, 65.1, 18.0. Mass spectrometry data are MS (MALDI-TOF): m / z 2051.20 [M + ].

[0119] Example 26 This embodiment provides a luminescent material (i.e., compound S26, whose structural formula is...). The preparation method of ) is largely the same as that of Example 24, except that: during preparation, Replace with Compound S26 is a pale yellow solid powder with a yield of 78%.

[0120] The test data for compound S26 are as follows: The proton NMR data are 1 H NMR (500 MHz, CDCl3) d (ppm): 10.85 (s, 1H), 9.62 (s, 2H), 8.03 (d, J = 7.6 Hz, 2H), 7.91 (d, J= 8.2 Hz, 2H), 7.86–7.78 (m, 8H), 7.74–7.63 (m, 10H), 7.56–7.48 (m, 18H), 7.42 (d, J = 8.4 Hz, 4H), 7.29 (d, J =8.4 Hz, 4H), 7.44–7.30 (m, 18H), 7.16 (t, J = 7.1 Hz, 2H), 7.04 (d, J = 6.5 Hz, 4H), 6.33 (s, 2H), 6.19 (s, 2H), 5.71 (s, 1H), 2.02 (s, 12H). The carbon NMR data are as follows: 13 C NMR (126 MHz, CDCl3) d (ppm): 158.12, 152.07, 149.12, 146.32, 145.98,144.22, 143.22, 142.62, 142.12, 140.25, 140.05, 139.30, 139.10, 138.32,138.08, 137.48, 137.10, 136.60, 136.10, 135.65, 135.08, 134.55, 134.15,133.75, 133.25, 130.15, 129.95, 129.70, 129.35, 129.18, 128.90, 128.50, 128.28, 128.12, 128.05, 128.00, 127.98, 125.35, 124.95, 124.45, 124.05, 122.25, 121.62, 119.35, 116.45, 115.85, 112.00, 106.18, 103.38, 102.88, 99.38, 65.0, 18.1. Mass spectrometry data are MS (MALDI-TOF): m / z 1876.65 [M + ].

[0121] Example 27 This embodiment provides a luminescent material (i.e., compound S27, whose structural formula is...). The preparation method of ) is largely the same as that of Example 15, except that: during preparation, Replace with The prepared compound S27 was a pale yellow solid powder, with a yield of 78%.

[0122] The test data for compound S27 are as follows: The proton NMR data are 1 H NMR (500 MHz, CDCl3) d (ppm): 10.96 (s, 1H), 9.70 (s, 2H), 7.96 (d, J = 7.5 Hz, 2H), 7.66 (d, J = 8.1 Hz, 2H), 7.86 (d, J = 8.3Hz, 2H), 7.78 (d, J = 7.8 Hz, 2H), 7.53 (d, J = 6.6 Hz, 18H), 7.51–7.45 (m,8H), 7.44–7.30 (m, 16H), 7.18 (t, J = 7.7 Hz, 2H), 7.06 (d, J = 7.5 Hz, 4H), 6.33 (s, 2H), 6.28 (s, 2H), 5.79 (s, 1H), 2.02 (s, 12H), 1.88 (s, 12H). The carbon NMR data are: 13 C NMR (126 MHz, CDCl3) d (ppm): 158.38, 152.30, 149.28, 146.60,146.22, 144.25, 143.10, 142.55, 140.35, 139.35, 138.45, 137.55, 136.70,136.18, 135.65, 134.98, 134.38, 134.05, 130.10, 129.85, 129.50, 129.30,128.95, 128.60, 128.35, 128.25, 128.18, 128.08, 125.58, 125.08, 122.45, 121.90, 119.60, 116.70, 116.05, 112.10, 106.38, 103.58, 103.08, 99.65, 18.10, 17.80. Mass spectrometry data are MS (MALDI-TOF): m / z 1876.65 [M + ].

[0123] Example 28 This embodiment provides a luminescent material (i.e., compound S28, whose structural formula is...). The preparation method of ) is largely the same as that of Example 27, except that: during preparation, Replace with The prepared compound S28 was a pale yellow solid powder with a yield of 69%.

[0124] The test data for compound S28 are as follows: The proton NMR data are 1 H NMR (500 MHz, CDCl3) d (ppm): 10.96 (s, 1H), 9.70 (s, 2H), 7.96 (d, J = 7.5 Hz, 2H), 7.66 (d, J = 8.1 Hz, 2H), 7.54 (t, J = 7.7Hz, 2H), 7.37 (d, J = 6.6 Hz, 2H), 7.33 (t, J = 7.4 Hz, 2H), 7.28 (d, J = 1.8Hz, 2H), 7.18 (t, J = 7.7 Hz, 2H), 7.06 (d, J = 7.5 Hz, 4H), 6.33 (s, 2H), 6.28 (s, 2H), 5.79 (s, 1H), 2.02 (s, 12H), 1.88 (s, 12H). The carbon NMR data are: 13 C NMR (126 MHz, CDCl3) d(ppm): 158.38, 152.30, 149.28, 146.60, 146.22, 144.25,143.10, 142.55, 140.35, 139.35, 138.45, 137.55, 136.70, 136.18, 135.65,134.98, 134.38, 134.05, 130.10, 129.85, 129.50, 129.30, 128.95, 128.60,128.35, 128.25, 128.18, 128.08, 125.58, 125.08, 122.45, 121.90, 119.60, 116.70, 116.05, 112.10, 106.38, 103.58, 103.08, 99.65, 18.10, 17.78. Mass spectrometry data are MS (MALDI-TOF): m / z 1693.86 [M + ].

[0125] Example 29 This embodiment provides a luminescent material (i.e., compound S29, whose structural formula is...). The preparation method of ) is largely the same as that of Example 22, except that one of them is used in the preparation. Replace with The prepared compound S29 was a pale yellow solid powder, with a yield of 71%.

[0126] The test data for compound S29 are as follows: The proton NMR data are 1 H NMR (500 MHz, CDCl3) d (ppm): 10.93 (s, 1H), 9.68 (s, 2H), 8.12 (d, J = 8.4 Hz, 2H), 7.98 (d, J = 7.7 Hz, 2H), 7.94 (d, J = 7.6 Hz, 2H), 7.66 (d, J = 8.1 Hz, 2H), 7.62–7.56 (m, 6H), 7.55–7.47 (m, 18H), 7.46–7.28 (m, 34H), 7.18 (t, J = 7.6 Hz, 2H), 7.06 (d, J= 7.6 Hz, 4H), 6.33 (s, 2H), 6.28 (s, 2H), 5.76 (s, 1H), 1.98 (s, 12H), 1.33 (s, 18H). The carbon NMR data are as follows: 13 C NMR (126 MHz, CDCl3) d (ppm): 158.30, 152.15, 149.25, 146.55, 146.10,144.10, 143.05, 142.40, 141.55, 140.25, 139.30, 138.45, 137.55, 136.75,136.20, 135.70, 135.15, 134.65, 134.20, 130.15, 129.90, 129.60, 129.35,129.10, 128.85, 128.60, 128.40, 128.28, 128.18, 128.10, 127.98, 125.65, 125.10, 122.40, 121.85, 119.60, 116.75, 116.05, 112.15, 106.45, 103.60, 103.10, 99.65, 34.8, 31.5, 17.9. Mass spectrometry data are MS (MALDI-TOF): m / z 1872.80 [M + ].

[0127] Example 30 This embodiment provides a luminescent material (i.e., compound S30, whose structural formula is...). The preparation method of ) is largely the same as that of Example 29, except that: during preparation, Replace with The prepared compound S30 was a pale yellow solid powder with a yield of 69%.

[0128] The test data for compound S30 are as follows: The proton NMR data are 1 H NMR (500 MHz, CDCl3) d (ppm): 10.93 (s, 1H), 9.68 (s, 2H), 8.12 (d, J = 8.4 Hz, 2H), 7.98 (d, J = 7.8 Hz, 2H), 7.94 (d, J = 7.6Hz, 2H), 7.66 (d, J= 8.1 Hz, 2H), 7.62–7.56 (m, 4H), 7.46–7.34 (m, 6H), 7.18(t, J = 7.6 Hz, 2H), 7.06 (d, J = 7.6 Hz, 4H), 6.33 (s, 2H), 6.28 (s, 2H), 5.76 (s, 1H), 1.98 (s, 12H), 1.33 (s, 18H). The carbon NMR data are as follows: 13 C NMR (126 MHz, CDCl3) d (ppm):158.30, 152.15, 149.25, 146.55, 146.10, 144.10, 143.05, 142.40,141.55, 140.25, 139.30, 138.45, 137.55, 136.75, 136.20, 135.70, 135.15,134.65, 134.20, 130.15, 129.90, 129.60, 129.35, 129.10, 128.85, 128.60,128.40, 128.28, 128.18, 128.10, 127.98, 125.65, 125.10, 122.40, 121.85, 119.60, 116.75, 116.05, 112.15, 106.45, 103.60, 103.10, 99.65, 34.8, 31.5, 17.9. Mass spectrometry data are MS (MALDI-TOF): m / z 1910.04 [M + ].

[0129] Example 31 This embodiment provides a luminescent material (i.e., compound S31, whose general structural formula is...). The preparation method of ) is largely the same as that of Example 22, except that one of them is selected during preparation. Replace with The prepared compound S31 was a pale yellow solid powder with a yield of 73%.

[0130] The test data for compound S31 are as follows: The proton NMR data are 1 H NMR (500 MHz, CDCl3) d(ppm): 10.94 (s, 1H), 9.69 (s, 2H), 8.20 (d, J = 8.3 Hz, 2H), 8.05 (d, J = 7.8 Hz, 2H), 7.98 (d, J = 7.6Hz, 2H), 7.72 (d, J = 8.2 Hz, 2H), 7.66–7.58 (m, 8H), 7.55–7.47 (m, 18H), 7.46–7.28 (m, 39H), 7.18 (t, J = 7.6 Hz, 2H), 7.06 (d, J = 7.6 Hz, 4H), 6.34(s, 2H), 6.28 (s, 2H), 5.76 (s, 1H), 1.99 (s, 12H), 1.33 (s, 18H). The carbon NMR data are as follows: 13 C NMR (126 MHz, CDCl3) d (ppm): 158.32, 152.18, 149.28, 146.60,146.15, 144.12, 143.08, 142.45, 141.70, 140.30, 139.35, 138.50, 137.62,136.82, 136.25, 135.75, 135.20, 134.70, 134.25, 130.18, 129.92, 129.65,129.38, 129.12, 128.90, 128.62, 128.42, 128.30, 128.18, 128.10, 127.98, 125.68, 125.12, 122.45, 121.88, 119.62, 116.78, 116.08, 112.18, 106.48, 103.62, 103.12, 99.68, 34.8, 31.5, 17.93. Mass spectrometry data are MS (MALDI-TOF): m / z 1912.83 [M + ].

[0131] Example 32 This embodiment provides a luminescent material (i.e., compound S32, whose structural formula is...). The preparation method of ) is largely the same as that of Example 31, except that: during preparation, Replace with .

[0132] The prepared compound S32 was a pale yellow solid powder with a yield of 75%.

[0133] The test data for compound S32 are as follows: The proton NMR data are 1 H NMR (500 MHz, CDCl3) d (ppm): 10.94 (s, 1H), 9.69 (s, 2H), 8.20 (d, J = 8.3 Hz, 2H), 8.05 (d, J = 7.8 Hz, 2H), 7.98 (d, J = 7.6Hz, 2H), 7.72 (d, J = 8.2 Hz, 2H), 7.66–7.58 (m, 6H), 7.46–7.34 (m, 4H), 7.18(t, J = 7.6 Hz, 2H), 7.06 (d, J = 7.6 Hz, 4H), 6.34 (s, 2H), 6.28 (s, 2H), 5.76 (s, 1H), 1.99 (s, 12H), 1.33 (s, 18H). The carbon NMR data are as follows: 13 C NMR (126 MHz, CDCl3) d (ppm): 158.32, 152.18, 149.28, 146.60, 146.15, 144.12, 143.08,142.45, 141.70, 140.30, 139.35, 138.50, 137.62, 136.82, 136.25, 135.75,135.20, 134.70, 134.25, 130.18, 129.92, 129.65, 129.38, 129.12, 128.90,128.62, 128.42, 128.30, 128.18, 128.10, 127.98, 125.68, 125.12, 122.45, 121.88, 119.62, 116.78, 116.08, 112.18, 106.48, 103.62, 103.12, 99.68, 34.8, 31.5, 17.9. Mass spectrometry data are MS (MALDI-TOF): m / z 1952.07 [M + ].

[0134] Example 33 This embodiment provides a luminescent material (i.e., compound S33, whose structural formula is...). The preparation method of ) is largely the same as that of Example 19, except that: during preparation, Replace with The prepared compound S33 was a pale yellow solid powder with a yield of 69%.

[0135] The test data for compound S33 are as follows: The proton NMR data are 1 H NMR (500 MHz, CDCl3) d (ppm): 10.93 (s, 1H), 9.69 (s, 2H), 8.33 (d, J = 8.4 Hz, 2H), 8.18 (d, J = 7.9 Hz, 2H), 8.07–7.98 (m, 8H), 7.89 (d, J = 8.2 Hz, 2H), 7.78 (d, J = 7.6 Hz, 2H), 7.72–7.62 (m, 10H), 7.56–7.48 (m, 18H), 7.45–7.28 (m, 26H), 7.18 (t, J = 7.3 Hz, 2H), 7.05 (d, J = 6.8 Hz, 4H), 6.33 (s, 2H), 6.21 (s, 2H), 5.74 (s, 1H), 2.03 (s, 12H). The carbon NMR data are: 13 C NMR (126 MHz, CDCl3) d(ppm): 182.1, 181.6, 158.18, 152.12, 149.18,146.38, 146.05, 144.30, 143.30, 142.70, 142.20, 140.35, 140.10, 139.35,139.15, 138.40, 138.18, 137.55, 137.15, 136.70, 136.20, 135.75, 135.20,134.65, 134.20, 133.82, 133.30, 130.20, 130.00, 129.75, 129.40, 129.20, 128.95, 128.55, 128.32, 128.18, 128.08, 128.02, 127.98, 125.45, 125.05, 124.55, 124.10, 122.35, 121.72, 119.45, 116.55, 115.92, 112.10, 106.28, 103.45, 102.95, 99.45, 65.1, 18.1. Mass spectrometry data are MS (MALDI-TOF): m / z 1868.70 [M + ].

[0136] Example 34 This embodiment provides a luminescent material (i.e., compound S34, whose structural formula is...). The preparation method of ) is largely the same as that of Example 33, except that: during preparation, Replace with The prepared compound S34 was a pale yellow solid powder, with a yield of 74%.

[0137] The test data for compound S34 are as follows: The proton NMR data are 1 H NMR (500 MHz, CDCl3) d(ppm): 10.92 (s, 1H), 9.68 (s, 2H), 8.33 (d, J = 8.4 Hz, 2H), 8.18 (d, J = 7.9 Hz, 2H), 7.89 (d, J = 8.2Hz, 2H), 7.78 (d, J = 7.6 Hz, 2H), 7.72–7.62 (m, 6H), 7.56–7.48 (m, 4H), 7.45–7.28 (m, 4H), 7.18 (t, J = 7.3 Hz, 2H), 7.05 (d, J = 6.8 Hz, 4H), 6.33(s, 2H), 6.21 (s, 2H), 5.74 (s, 1H), 2.03 (s, 12H). The carbon NMR data are as follows: 13 C NMR (126 MHz, CDCl3) d (ppm):182.2, 181.6, 158.18, 152.12, 149.18, 146.38, 146.05,144.30, 143.31, 142.70, 142.21, 140.36, 140.10, 139.35, 139.15, 138.40,138.18, 137.55, 137.15, 136.70, 136.20, 135.75, 135.20, 134.66, 134.21,133.83, 133.33, 130.21, 130.01, 129.75, 129.40, 129.20, 128.95, 128.57, 128.32, 128.18, 128.08, 128.02, 127.98, 125.45, 125.05, 124.55, 124.10, 122.35, 121.72, 119.45, 116.55, 115.93, 112.12, 106.27, 103.45, 102.95, 99.45, 65.1, 18.1. Mass spectrometry data are MS (MALDI-TOF): m / z 1906.94 [M + ].

[0138] Example 35 This embodiment provides a luminescent material (i.e., compound S35, whose structural formula is...). The preparation method of ) is largely the same as that of Example 5, except that: during preparation, Replace with The prepared compound S35 was an orange-yellow solid powder with a yield of 70%.

[0139] The test data for compound S35 are as follows: The proton NMR data are 1 H NMR (500 MHz, CDCl3) d (ppm): 8.95 (td, J = 9.8, 5.6 Hz, 3H), 8.77 (d, J = 1.9 Hz, 1H), 8.55 (s, 1H), 8.53–8.49 (m, 1H), 8.43(s, 1H), 8.39 (d, J = 1.8 Hz, 1H), 8.26–8.17 (m, 3H), 7.97 (d, J = 7.9 Hz, 1H), 7.77–7.69 (m, 11H), 7.66–7.59 (m, 2H), 7.58–7.44 (m, 15H), 1.55 (s, 9H), 1.49 (s, 9H). The carbon NMR data are: 13 C NMR (126 MHz, CDCl3) δ (ppm): 145.42, 144.92,144.20, 142.45, 141.58, 141.14, 139.28, 138.28, 138.12, 137.95, 136.56,136.33, 135.62, 135.32, 134.18, 130.18, 129.85, 129.32, 129.22, 128.74,128.12, 127.98, 127.56, 127.03, 126.78, 126.64, 125.76, 124.44, 124.40, 123.66, 123.52, 122.36, 121.62, 121.33, 120.60, 120.35, 119.54, 117.10, 116.85, 114.15, 114.06, 109.82, 107.80, 107.06, 35.00, 34.78, 32.22, 31.88. Mass spectrometry data are MS (MALDI-TOF): m / z 1028.47 [M + ].

[0140] Example 36 This embodiment provides a luminescent material (i.e., compound S36, whose structural formula is...). The preparation method of ) is largely the same as that of Example 35, except that: during preparation, Replace with The prepared compound S36 was an orange-yellow solid powder with a yield of 67%.

[0141] The proton NMR data are 1 H NMR (500 MHz, CDCl3) d (ppm): 8.94 (td, J = 9.8, 5.6 Hz, 3H), 8.76 (d, J = 1.9 Hz, 1H), 8.54 (s, 1H), 8.52–8.48 (m, 1H), 8.42(s, 1H), 8.38 (d, J = 1.8 Hz, 1H), 8.25–8.16 (m, 3H), 7.96 (d, J = 7.8 Hz, 1H), 7.78–7.71 (m, 5H), 7.66–7.60 (m, 1H), 7.57–7.48 (m, 3H), 1.54 (s, 9H), 1.48 (s, 9H). The carbon NMR data are: 13 C NMR (126 MHz, CDCl3) δ (ppm): 145.40, 144.90,144.18, 142.42, 141.55, 141.12, 139.24, 138.24, 138.10, 137.92, 136.52,136.29, 135.58, 135.28, 134.14, 130.14, 129.81, 129.28, 129.19, 128.70,128.09, 127.95, 127.53, 126.99, 126.74, 126.61, 125.73, 124.41, 124.37, 123.63, 123.48, 122.32, 121.58, 121.29, 120.56, 120.31, 119.50, 117.06, 116.81, 114.11, 114.03, 109.78, 107.76, 107.02, 34.98, 34.76, 32.20, 31.86. Mass spectrometry data are MS (MALDI-TOF): m / z 1047.58 [M + ].

[0142] Application Example 1 This application example provides a method for fabricating an organic electroluminescent device, comprising the following steps: IZO glass substrate (i.e., IZO coated glass, specifications: thickness of 75 nm, thin film resistivity of 10 Ω m) -2 The IZO glass substrates (30 mm × 30 mm in size) were sequentially cleaned using a cleaning machine, with each cleaning cycle lasting 60 minutes, to thoroughly remove stains and dust from the surface. They were then baked on a 230°C hot plate for 30 minutes. Afterward, they were dried in an electric hot air drying oven for 24 hours. Subsequently, the dried IZO glass substrates were subjected to UV exposure and O2 plasma treatment for 15 minutes to adjust the surface work function.

[0143] The treated IZO glass substrate was used as the device anode. Then, ink containing dissolved hole injection material (concentration of 12 mg / mL) was filled into the inkjet printer cartridge in a nitrogen glove box. Nine picoliters of ink were injected into each pixel on the IZO glass substrate, followed by vacuum degassing for 5 min (vacuum degree of 1×10⁻⁶). -4 The material was annealed at 230°C for 30 minutes (MPa) to form a 30 nm thick hole injection layer (HI layer).

[0144] Then, the hole transport layer material (concentration of 30 mg / mL) dissolved in a mixed solution of xylene and cyclohexylbenzene was filtered and poured into the inkjet printer cartridge. 25 picoliters of ink were injected into each pixel on the HI layer, and a vacuum degassing process was performed for 5 minutes (vacuum degree 1×10⁻⁶). -4 The material was annealed at 230°C for 30 minutes to form a 25 nm thick hole transport layer (HT layer).

[0145] The luminescent layer material (concentration 20 mg / mL) was then dissolved in a mixed solution of xylene and cyclohexylbenzene to prepare ink, which was then filled into the inkjet printer cartridge. 40 picoliters of ink were then applied to each pixel of the HT layer, followed by vacuum degassing for 5 minutes (vacuum degree 1 × 10⁻⁶). -4 The solution was annealed at 140°C for 20 min to form a 45 nm thick light-emitting layer (EML layer).

[0146] The product obtained in the above steps is then transferred into a vacuum evaporation chamber (vacuum degree 1×10⁻⁶). -6Vacuum evaporation is performed on the EML layer to deposit electron transport material using a mask, forming a 30 nm thick electron transport layer (ET layer). Then, 1 nm of Yb is deposited on the ET layer to form an electron injection layer. Next, 20 nm thick Ag is deposited on the Yb to form a cathode. Then, a 60 nm thick refracting layer (CPL) is deposited. Finally, the organic electroluminescent device is prepared by UV curing and encapsulation followed by heating and baking for 20 min.

[0147] The device structure is: IZO / HI (30 nm) / HT (25 nm) / EML (45 nm) / ET (30 nm) / Yb (1 nm) / Ag (20 nm) / CPL (60 nm).

[0148] HAT-CN (2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzophenanthrene) was selected as the hole injection material, CBP (4,4'-bis(9-carbazole)biphenyl) was selected as the hole transport material, and Liq (lithium 8-hydroxyphosphate) and TPBi (1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene) in a mass ratio of 2:8 (Liq:TPBi=2:8) were selected as the electron transport materials. The light-emitting layer material is selected. It consists of a host material, an exciton-sensitizing material, and a guest material, with a mass ratio of 89:10:1. The host material is a dual-host material. (The mass ratio of the two is 1:1), the exciton sensitizing material is Ir(mPPy)3 (tris(2-p-tolylpyridine)iridium), and the guest material is compound S1.

[0149] Application Example 2-36 In Application Example 1, the guest materials were selected from compounds S2 to S36, and the other conditions remained unchanged to prepare the corresponding organic electroluminescent devices.

[0150] The electroluminescence performance of the organic electroluminescent devices fabricated according to examples 1-36 was tested. EQE (external quantum efficiency)-luminescence curves and electroluminescence spectra were acquired using a Keithley 2400 and an absolute external quantum efficiency measurement system (C9920-12, Hamamatsu Photonics, Japan). The device lifetime (LT) was evaluated by measuring the luminescence over time at a constant current density. 80 LT 80 This refers to the time it takes for the brightness to decay to 80% of its initial brightness, where the initial brightness is 5000 cd / m². -2 The performance test results are shown in Table 1 and... Figure 2As shown.

[0151] Table 1. Test Results

[0152] The results in Table 1 show that the luminescent materials provided by this invention all possess narrow-band emission characteristics, are pure green luminescent materials, and have narrower emission spectra compared to most multiple resonance thermally activated delayed fluorescence materials. Furthermore, the aforementioned devices not only have high EQE, but their narrow-band emission characteristics also make it easier to achieve high color purity output. In addition, under appropriate doping ratios, the color coordinates of the green light device can reach CIE. y The color purity is approximately 0.79, meeting the BT.2020 green gamut requirements, thus effectively solving the problem that the color purity of some existing MR-TADF green light systems is difficult to meet the BT.2020 standard. Furthermore, the luminescent material provided by this invention achieves high color purity and high efficiency while also exhibiting excellent device stability, providing support for its practical application in the field of ultra-high-definition displays.

[0153] In summary, this invention provides a luminescent material, an organic electroluminescent device, and a preparation method. The luminescent material provided is a boron-based narrow-band pure green luminescent material. By introducing triphenylsilane and its derivatives, this luminescent material can improve morphological and thermal stability, and significantly reduce intermolecular packing, suppressing harmful intermolecular aggregation and non-radiative transition channels, thus improving device stability and external quantum efficiency in electroluminescent devices. The luminescent material provided by this invention combines narrow-band emission, high external quantum efficiency, and significantly extended device lifetime.

[0154] It should be understood that the application of the present invention is not limited to the examples above. Those skilled in the art can make improvements or modifications based on the above description, and all such improvements and modifications should fall within the protection scope of the appended claims.

Claims

1. A luminescent material, characterized in that, The general structural formula of the luminescent material is shown in formula (1) or formula (2): Among them, Ar1, Ar2, and Ar5 are each independently substituted C6-C. 60 Aryl, unsubstituted C6-C 60 Aryl, substituted C4-C 60 heteroaryl or unsubstituted C4-C 60 Mixed aromatics; Ar3 is a group containing 18-160 carbon atoms in a triphenylsilane group; Ar4 is selected from one of the following structures: , , , , and ; X1, X2, X3, X4, and X5 are each independently selected from single bonds, O, S, Se, and CR. a R b SiR a R b NR c One of them; and when X1, X2, or X3 is a single bond, it can fuse with Ar1, Ar2, or Ar5 to form a five-membered ring, six-membered ring, or seven-membered ring structure; R a R b R c Each group is independently selected from H, D, F, Cl, Br, I, benzyl, ester, amide, carbonyl, aldehyde, nitro, and unsubstituted C1-C groups. 30 Alkyl, substituted C1-C 30 Alkyl, unsubstituted C1-C 10 Alkoxy, substituted C1-C 10 Alkoxy, unsubstituted C3-C 30 cycloalkyl, substituted C3-C 30 cycloalkyl, unsubstituted C1-C 30 Alkylthio, substituted C1-C 30 Alkylthio, unsubstituted C6-C 30 Aryl, substituted C6-C 30 Aryl, unsubstituted C4-C 30 heteroaryl, substituted C4-C 30 One of the heteroaryl groups; Indicates the connection site.

2. The luminescent material according to claim 1, characterized in that, Ar3 is selected from one of the following structures: , , , , and ; Wherein, R2 to R8 are located at any connectable position on their respective benzene rings, and R2 to R8 are monosubstituted or polysubstituted, each independently selected from at least one of the following groups: H, D, , , , , and ; in, Indicating the connection sites, R9 and R10 are located at any connectable position on their respective benzene rings. R9 and R10 are each independently selected from H, D, F, Cl, Br, I, benzyl, ester, amide, carbonyl, aldehyde, nitro, and unsubstituted C1-C groups. 30 Alkyl, substituted C1-C 30 Alkyl, unsubstituted C1-C 10 Alkoxy, substituted C1-C 10 Alkoxy, unsubstituted C1-C 10 Alkylamino, substituted C1-C 10 Alkylamino, unsubstituted C3-C 10 cycloalkyl, substituted C3-C 10 cycloalkyl, unsubstituted C1-C 30 Alkylthio, substituted C1-C 30 Alkylthio, unsubstituted C6-C 30 Aryl, substituted C6-C 30 Aryl, unsubstituted C4-C 30 heteroaryl, substituted C4-C 30 One of the heteroaryl groups.

3. The luminescent material according to claim 1, characterized in that, The substituted C6-C 60 Aryl, substituted C4-C 60 The substituents in the heteroaryl group are each independently selected from H, D, F, Cl, Br, I, nitrile, acyl, or unsubstituted C1-C. 30 Alkyl, substituted C1-C 30 Alkyl, unsubstituted C1-C 10 Alkoxy, substituted C1-C 10 Alkoxy, unsubstituted C3-C 30 cycloalkyl, substituted C3-C 30 cycloalkyl, unsubstituted C1-C 30 Alkylthio, substituted C1-C 30 Alkylthio, unsubstituted C6-C 30 Aryl, substituted C6-C 30 Aryl, unsubstituted C4-C 30 heteroaryl, substituted C4-C 30 One of the heteroaryl groups.

4. The luminescent material according to claim 1, characterized in that, Ar1, Ar2, and Ar5 are each independently selected from one of the following structures: ； in, Indicates the linking site. R11 is located at any connectable position on its benzene ring. In different structural formulas, R11 is independently selected from H, D, F, Cl, Br, I, cyano, benzyl, ester, amide, carbonyl, aldehyde, nitro, substituted amino, unsubstituted amino, substituted borane, unsubstituted borane, and substituted C1-C. 30 Alkyl, unsubstituted C1-C 30 Alkyl, substituted C1-C 10 Alkoxy, unsubstituted C1-C 10 Alkoxy, substituted C1-C 10 Alkylamino, unsubstituted C1-C 10 Alkylamino, substituted C3-C 30 cycloalkyl, unsubstituted C3-C 30 cycloalkyl, substituted C1-C 30 Alkylthio, unsubstituted C1-C 30 Alkylthio, substituted C6-C 30 Aryl, unsubstituted C6-C 30 Aryl, substituted C4-C 30 heteroaryl, unsubstituted C4-C 30 One of the heteroaryl groups.

5. The luminescent material according to claim 1, characterized in that, The luminescent material is selected from one of the following structures: .

6. A method for preparing the luminescent material according to any one of claims 1-5, characterized in that, Includes the following steps: Will and or After the reaction, we get That is, the luminescent material; or, Will and or After the reaction, we get That is, the luminescent material; Where X is a halogen.

7. An organic electroluminescent device, characterized in that, It includes a first electrode, a light-emitting layer, and a second electrode stacked sequentially; the light-emitting layer includes the light-emitting material according to any one of claims 1-5.

8. The organic electroluminescent device according to claim 7, characterized in that, The organic electroluminescent device includes a refractive layer, a first electrode, an electron injection layer, an electron transport layer, a light-emitting layer, a hole transport layer, a hole injection layer, and a second electrode, which are stacked sequentially. The luminescent layer comprises a host material, an exciton-sensitizing material, and a guest material. The host material comprises a thermally activated delayed fluorescence material, the exciton-sensitizing material comprises a complex containing a metal element, and the guest material comprises the luminescent material. The mass ratio of the host material, exciton sensitizing material and guest material is (60~94.5):(5~30):(0.5~5).

9. A method for fabricating an organic electroluminescent device according to any one of claims 7-8, characterized in that, Includes the following steps: Provide a second electrode; An emitting layer and a first electrode are sequentially formed on the second electrode to obtain the organic electroluminescent device.

10. The preparation method according to claim 9, characterized in that, The preparation method specifically includes the following steps: Provide a second electrode; A hole injection layer, a hole transport layer, and a light-emitting layer are sequentially formed on the second electrode using inkjet printing; an electron transport layer, an electron injection layer, a first electrode, and a refractive layer are sequentially formed on the light-emitting layer using vacuum evaporation.

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