A narrow-band emitting pyrene-based blue light material, and a preparation method and application thereof

Abstract

The application belongs to the field of synthesis of organic semiconductors, and discloses a narrow-band emission pyrene-based blue light material and a preparation method and application thereof.The narrow-band emission pyrene-based blue light material has a structure as shown in formula (1).The pyrene-based organic functional light-emitting material prepared by taking the pyrene intermediate of the application as a precursor is prepared by introducing a biphenyl and triphenylamine or tetraphenylethylene at positions 1 and 3 of the pyrene;in the case of triphenylamine as a strong electron-donating group, the biphenyl units substituted at different positions are used to build the molecular conformation through space conjugation, and the tetraphenylethylene unit plays an important role in realizing the AIE characteristics.The preparation method is simple, the reaction condition is mild, the yield is high, the prepared material has good thermal stability, (deep) blue light emission, the solid quantum yield is greater than 0.7, the highest can be up to 0.9, and the maximum half-peak width is between 20-50 nm.The application is suitable for application scenarios such as high-definition display light-emitting devices.

Description

Technical Field

[0001] This invention belongs to the field of synthesis of organic semiconductor optoelectronic materials, and specifically relates to a narrowband pyrene-based blue light material, its preparation method, and its application. Background Technology

[0002] Organic light-emitting diodes (OLEDs) are electroluminescent devices capable of generating light within an organic emitting layer under an external voltage. OLEDs are now widely used in mobile phones, smartwatches, cameras, and other fields. OLED displays offer a range of advantages, including self-illumination, low-voltage DC drive, all-solid-state operation, wide viewing angles, light weight, and simple composition and manufacturing processes. Compared to liquid crystal displays (LCDs), OLEDs do not require a backlight, have a wider viewing angle, lower power consumption, and a response speed up to 1000 times faster than LCDs, while maintaining lower manufacturing costs than LCDs of equivalent resolution. Therefore, OLEDs have a promising future in the market.

[0003] The performance of organic light-emitting materials determines the performance and lifespan of OLED devices and is a core technology for achieving high-performance OLED devices. The molecular structure, stacking mode of light-emitting molecules, and morphology of aggregated states of organic semiconductor light-emitting materials significantly affect the material's luminescence behavior. Many organic light emitters exhibit drastically different luminescence behaviors from the molecular level to the aggregated state. In some cases, luminescence can be weakened or quenched at high concentrations, a phenomenon known as "aggregation-induced quenching (ACQ)." In contrast to ACQ, aggregation-induced emission (AIE) is a phenomenon where light-emitting materials exhibit enhanced emission in the aggregated state. This is mainly because intramolecular rotational confinement prevents non-radiative transitions, and excited excitons can only release energy through radiation, increasing the luminescence intensity of AIE materials in the solid state. Due to the unique properties of AIE molecules, they can be used in both doped and undoped OLED devices, exhibiting high efficiency, high brightness, and low efficiency roll-off. According to the BT 2020 wide color gamut standard, the emission spectra of the three primary color materials (red (R), green (G), and blue (B)) require small full width at half maximum (FWHM), which is crucial for improving high-definition displays. Therefore, from a materials perspective, developing organic light-emitting materials with narrow-band emission is crucial for the color purity of optoelectronic devices. However, the strong vibrational coupling between the ground and excited states of traditional organic light-emitting materials results in a wide full width at half maximum (FWHM) of the emission spectrum. Therefore, designing and synthesizing organic light-emitting materials with narrow-band emission is of great significance for realizing high-definition OLED devices. Summary of the Invention

[0004] To address the shortcomings and deficiencies of the existing technologies, this invention uses pyrene as the core and, through chemical synthesis, designs a type of pyrene-based blue light-emitting material with narrowband emission. This luminescent material exhibits good thermal stability, a maximum emission peak less than 470 nm, a solid-state quantum yield greater than 0.7 (up to 0.9), a maximum half-width at half-maximum (WWHM) less than 50 nm, and a minimum WWHM of 33 nm. It also possesses high color purity, which helps to achieve narrowband blue light emission.

[0005] Another object of the present invention is to provide a method for preparing the above-mentioned narrowband pyrene-based blue light material.

[0006] Another object of the present invention is to provide the application of the above-mentioned narrowband emitting pyrene-based blue light material.

[0007] The objective of this invention is achieved through the following technical solution:

[0008] A narrowband pyrene-based blue light-emitting material, wherein the narrowband pyrene-based blue light-emitting material has the structure shown in formula (1):

[0009]

[0010] When R1 is When R2 is

[0011] When R1 is When R2 is

[0012] When R1 is When R2 is

[0013] The specific structural formula of the aforementioned narrowband pyrene-based blue light-emitting material is as follows:

[0014]

[0015] The above-mentioned method for preparing a narrowband pyrene-based blue light-emitting material includes the following steps:

[0016] (1) Under an inert atmosphere, the 7-tert-butyl-1-bromopyrene intermediate was added to a mixed solution of arylboronic acid and its derivatives, an inorganic base, a solvent, and a palladium catalyst. The mixture was stirred at 90℃~100℃ for 24~48h to carry out a metal-catalyzed coupling reaction. Functional substitution was performed at the 1-site of pyrene to prepare the precursor 7-tert-butyl-1-R1 group pyrene. The precursor 7-tert-butyl-1-R1 group pyrene has the structure shown in formula (2) below:

[0017]

[0018] Where R1 is

[0019] (2) Under an inert atmosphere, the precursor 7-tert-butyl-1-R1 pyrene obtained in step (1) is added to a mixed solution of brominating agent and solvent, and the mixture is stirred at 25℃~50℃ for 12~48h to carry out a bromination reaction. A halogenated substitution is performed at the 3-site of pyrene to prepare a 7-tert-butyl-1-R1 group-substituted-3-halogenated pyrene intermediate. The 7-tert-butyl-1-R1 group-substituted-3-halogenated pyrene intermediate has the structure shown in formula (3) below:

[0020]

[0021] R3 is one of fluorine, chlorine, bromine or iodine;

[0022] (3) Under an inert atmosphere, the 3-halogenated pyrene intermediate with 7-tert-butyl-1-R1 group substituted is added to a mixed solution of arylboronic acid and its derivatives, inorganic base, solvent and palladium catalyst, and stirred at 90℃~100℃ for 24~48h to carry out metal-catalyzed coupling reaction, and functionalized substitution is performed at the 3-site of pyrene to prepare narrowband pyrene blue light material.

[0023] The inert atmosphere in step (1) is one or both of nitrogen and argon; the palladium catalyst is one or more of tetra(triphenylphosphine)palladium, palladium acetate, or bis(triphenylphosphine)palladium dichloride; the inorganic base is one or more of potassium carbonate, sodium carbonate, sodium bicarbonate, and potassium bicarbonate; the arylboronic acid and its derivatives are 4-methoxyphenylboronic acid, 4,4'-dimethoxy-4”-boronic acid triphenylamine, 4-boronic acid triphenylamine, 1-(4-phenylboronic acid pinacol ester)-1,2,2-tristyrene, bis-pinacol boronic acid ester, 1-boronic acid ester-2 -Hydroxypyrene, carbazole and its derivatives, phenthiazide and its derivatives, diphenylamine and its derivatives or tetrahydropyrrole, more preferably 2-triphenylamineboronic acid, 3-triphenylamineboronic acid, 4-triphenylamineboronic acid, 1-(4-phenylboronic acid pinacol ester)-1,2,2-triphenylethylene; the molar ratio of the 7-tert-butyl-1-bromopyrene intermediate, arylboronic acid and its derivatives, inorganic base and palladium catalyst is 1:(1-3):(2-10):(1-5); the solvent is a mixture of water, ethanol and toluene in a volume ratio of (1-5):(1-5):1.

[0024] The inert atmosphere in step (3) is one or both of nitrogen and argon; the palladium catalyst is one or more of tetra(triphenylphosphine)palladium, palladium acetate, or bis(triphenylphosphine)palladium dichloride; the inorganic base is one or more of potassium carbonate, sodium carbonate, sodium bicarbonate, and potassium bicarbonate; the arylboronic acid and its derivatives are 4-methoxyphenylboronic acid, 4,4'-dimethoxy-4”-boronic acid triphenylamine, 4-boronic acid triphenylamine, 1-(4-phenylboronic acid pinacol ester)-1,2,2-tristyrene, bis-pinacol boronic acid ester, 1-boronic acid ester-2-hydroxypyrene, and carbazole. The solvent is preferably 2-triphenylamine boric acid, 3-triphenylamine boric acid, 4-triphenylamine boric acid, or 1-(4-phenylboronic acid pinacol ester)-1,2,2-triphenylethylene; the molar ratio of the 7-tert-butyl-1-R1 group-substituted 3-halogenated pyrene intermediate, arylboronic acid and its derivatives, inorganic base, and palladium catalyst is 1:(1-3):(2-10):(1-5); the solvent is a mixture of water, ethanol, and toluene in a volume ratio of (1-5):(1-5):1.

[0025] The inert atmosphere in step (2) is nitrogen or argon; the brominating agent is one or more of bromine water, NBS, BTMABr3, chlorine, fluorine, and iodine; the solvent is one or more of dichloromethane, tetrahydrofuran, water, and ethanol; and the molar ratio of the precursor 7-tert-butyl-1-R1 pyrene to the brominating agent is 1:(1-5).

[0026] Applications of the aforementioned narrowband-emitting pyrene-based blue light-emitting materials in organic optoelectronic devices.

[0027] The organic optoelectronic devices include organic light-emitting diodes, organic field-effect transistors, solar cells, or organic lasers.

[0028] The 1-R1-substituted 7-tert-butylpyrene is 1-([1,1'-biphenyl]-4-yl)-7-tert-butyl)pyrene, 1-([1,1'-biphenyl]-3-yl)-7-tert-butyl)pyrene, and 1-([1,1'-biphenyl]-2-yl)-7-tert-butyl)pyrene, and their molecular structural formulas are shown in 1a, 1b, and 1c:

[0029]

[0030] The 7-tert-butyl-1-R1 group-substituted 3-halogenated pyrene intermediates are 1-([1,1'-biphenyl]-4-yl)-3-bromo-7-(tert-butyl)pyrene, 1-([1,1'-biphenyl]-3-yl)-3-bromo-7-(tert-butyl)pyrene, and 1-([1,1'-biphenyl]-2-yl)-3-bromo-7-(tert-butyl)pyrene, with molecular structures shown in formulas 2a, 2b, and 2c:

[0031]

[0032] The narrowband-emitting pyrene-based blue light material is 4-(3-(1,1'-biphenyl)-4-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline, 4-(3-(1,1'-biphenyl)-3-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline, 4-(3-(1,1'-biphenyl)-2-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline, 1-([1,1'-biphenyl]-2-yl)-7-tert-butyl-3-(4-(1,2,2-triphenylvinyl)phenyl)pyrene, 3-(3-(1,1'-biphenyl)-4-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline, 3-(3-( 1,1'-biphenyl)-3-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline, 3-(3-(1,1'-biphenyl)-2-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline, 1-([1,1'-biphenyl]-4-yl)-7-tert-butyl-3-(4-(1,2,2-triphenylvinyl)phenyl)pyrene, 1-([1,1'-biphenyl]-3-yl)-7-tert-butyl-3-(4-(1,2,2-triphenylvinyl)phenyl)pyrene and 1,3-([1,1'-biphenyl]-3-yl)-7-(tert-butyl)pyrene, with structural formulas as shown in 3a, 3b, 3c, 3d, 3e, 3f, 3g, 3h and 3i:

[0033]

[0034] The synthesis steps of the above-mentioned narrowband pyrene-based blue light-emitting material are shown in equation (Ⅰ):

[0035]

[0036]

[0037] The present invention has the following advantages and effects compared with the prior art:

[0038] (1) The pyrene-based organic functional light-emitting material prepared using the pyrene intermediate of the present invention as a precursor is prepared by introducing biphenyl and triphenylamine (TPA) or tetraphenylethylene (TPE) at the 1 and 3 positions of pyrene. In the case of triphenylamine (TPA) as a strong electron-donating group, the biphenyl units substituted at different positions are used to construct molecular conformations through spatial conjugation, and the tetraphenylethylene unit plays an important role in realizing AIE properties.

[0039] (2) The synthesis method of the present invention has the advantages of simple experimental operation, reasonable process design, high yield, mild reaction conditions, low raw material price, and high intermediate yield.

[0040] (3) The pyrene-based organic functional luminescent material of the present invention has improved solubility due to the presence of tert-butyl groups. The introduction of biphenyl, triphenylamine (TPA) or tetraphenylethylene (TPE) achieves narrow-band blue light emission, high fluorescence quantum yield and high thermal stability, which facilitates its application in the OLED field. Attached Figure Description

[0041] Figure 1 1-([1,1'-biphenyl]-4-yl)-7-tert-butyl)pyrene as described in Example 1 1 H NMR spectrum.

[0042] Figure 2 The HRMS plot of 1-([1,1'-biphenyl]-4-yl)-7-tert-butyl)pyrene in Example 1 is shown.

[0043] Figure 3 1-([1,1'-biphenyl]-3-yl)-7-tert-butyl)pyrene as described in Example 2 1 H NMR spectrum.

[0044] Figure 4 The HRMS plot of 1-([1,1'-biphenyl]-3-yl)-7-tert-butyl)pyrene in Example 2 is shown.

[0045] Figure 5 The 1-([1,1'-biphenyl]-2-yl)-7-tert-butyl)pyrene of Example 3 1 H NMR spectrum.

[0046] Figure 6 The HRMS plot of 1-([1,1'-biphenyl]-2-yl)-7-tert-butyl)pyrene in Example 3 is shown.

[0047] Figure 7 The 1-([1,1'-biphenyl]-4-yl)-3-bromo-7-(tert-butyl)pyrene of Example 4 1 H NMR spectrum.

[0048] Figure 8 The HRMS plot of 1-([1,1'-biphenyl]-4-yl)-3-bromo-7-(tert-butyl)pyrene in Example 4 is shown.

[0049] Figure 9 The 1-([1,1'-biphenyl]-3-yl)-3-bromo-7-(tert-butyl)pyrene of Example 5 1 H NMR spectrum.

[0050] Figure 10 The HRMS plot of 1-([1,1'-biphenyl]-3-yl)-3-bromo-7-(tert-butyl)pyrene in Example 5 is shown.

[0051] Figure 11 The 1-([1,1'-biphenyl]-2-yl)-3-bromo-7-(tert-butyl)pyrene of Example 6 1 H NMR spectrum.

[0052] Figure 12 The HRMS plot of 1-([1,1'-biphenyl]-2-yl)-3-bromo-7-(tert-butyl)pyrene in Example 6 is shown.

[0053] Figure 13 The 4-(3-(1,1'-biphenyl)-4-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline of Example 7 1 H NMR spectrum.

[0054] Figure 14 The HRMS plot of 4-(3-(1,1'-biphenyl)-4-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline of Example 7 is shown.

[0055] Figure 15 The 4-(3-(1,1'-biphenyl)-3-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline of Example 8 1 H NMR spectrum.

[0056] Figure 16 The HRMS plot of 4-(3-(1,1'-biphenyl)-3-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline of Example 8 is shown.

[0057] Figure 17 The 4-(3-(1,1'-biphenyl)-2-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline of Example 9 1 H NMR spectrum.

[0058] Figure 18 The HRMS plot of 4-(3-(1,1'-biphenyl)-2-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline of Example 9 is shown.

[0059] Figure 19 The 1-([1,1'-biphenyl]-2-yl)-7-tert-butyl-3-(4-(1,2,2-triphenylvinyl)phenyl)pyrene of Example 10 1 H NMR spectrum.

[0060] Figure 20 The HRMS plot of 1-([1,1'-biphenyl]-2-yl)-7-tert-butyl-3-(4-(1,2,2-triphenylvinyl)phenyl)pyrene in Example 10 is shown.

[0061] Figure 21 The 3-(3-(1,1'-biphenyl)-4-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline of Example 11 1 H NMR spectrum.

[0062] Figure 22 The HRMS plot of 3-(3-(1,1'-biphenyl)-4-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline from Example 11 is shown.

[0063] Figure 23 The 3-(3-(1,1'-biphenyl)-3-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline of Example 12 1 H NMR spectrum.

[0064] Figure 24 The HRMS plot of 3-(3-(1,1'-biphenyl)-3-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline of Example 12 is shown.

[0065] Figure 25 The 3-(3-(1,1'-biphenyl)-2-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline of Example 13 1 H NMR spectrum.

[0066] Figure 26 The HRMS plot of 3-(3-(1,1'-biphenyl)-2-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline of Example 13 is shown.

[0067] Figure 27 The 1-([1,1'-biphenyl]-3-yl)-7-tert-butyl-3-(4-(1,2,2-triphenylvinyl)phenyl)pyrene of Example 14 1 H NMR spectrum.

[0068] Figure 28 HRMS plot of 1-([1,1'-biphenyl]-3-yl)-7-tert-butyl-3-(4-(1,2,2-triphenylvinyl)phenyl)pyrene in Example 14.

[0069] Figure 29 The 1,3-([1,1'-biphenyl]-3-yl)-7-(tert-butyl)pyrene of Example 15 1 H NMR spectrum.

[0070] Figure 30 The HRMS plot of 1,3-([1,1'-biphenyl]-3-yl)-7-(tert-butyl)pyrene in Example 15 is shown.

[0071] Figure 31 The fluorescence spectra of the pyrene-based organic functional luminescent materials 3a-d obtained in Examples 7-10 are shown in the solid state.

[0072] Figure 32 The fluorescence spectra of the 3e-i pyrene-based organic functional luminescent materials obtained in Examples 11-15 are shown in the solid state. Detailed Implementation

[0073] The following specific embodiments further illustrate the content of the present invention, but should not be construed as limiting the present invention.

[0074] Example 1: Preparation of 1-([1,1'-biphenyl]-4-yl)-7-tert-butyl)pyrene

[0075] In a double-necked round-bottom flask, 7-tert-butyl-1-bromopyrene (1.0 eq), 4-biphenylboronic acid (1.1 eq), and K₂CO₃ (2.9 eq) were dissolved in a mixture of toluene, ethanol, and H₂O under a N₂ atmosphere and stirred at room temperature for 5 minutes. Tetra(triphenylphosphine)palladium(O) was then added to the mixture, and the mixture was vigorously stirred at 90 °C for 36 h. After cooling to room temperature, the mixture was quenched with water, extracted three times with dichloromethane, and the combined organic phases were washed with water and saturated brine, dried over anhydrous magnesium sulfate (MgSO₄), and the organic phase was evaporated. The residue was treated with n-hexane / dichloromethane (V₂O₃ / V₂O₃) solution. hexane V CH2Cl2 Using a 3:1 ratio as the eluent, the product 1-([1,1'-biphenyl]-4-yl)-7-(tert-butyl) was further purified by column chromatography with a yield of 77.8%. The synthetic route is shown in the following formula.

[0076]

[0077] Figure 1 The 1-([1,1'-biphenyl]-4-yl)-7-tert-butyl)pyrene obtained in this embodiment 1 H NMR spectrum, Figure 2 The HRMS plot of 1-([1,1'-biphenyl]-4-yl)-7-tert-butyl)pyrene obtained in this embodiment is shown below. Figure 1-2 It can be seen that 1-([1,1'-biphenyl]-4-yl)-7-tert-butyl)pyrene was successfully prepared.

[0078] Example 2: Preparation of 1-([1,1'-biphenyl]-3-yl)-7-tert-butyl)pyrene

[0079] In a double-necked round-bottom flask, 7-tert-butyl-1-bromopyrene (1.0 eq), 3-biphenylboronic acid (1.1 eq), and K₂CO₃ (2.9 eq) were dissolved in a mixture of toluene, ethanol, and H₂O under a N₂ atmosphere and stirred at room temperature for 5 minutes. Tetra(triphenylphosphine)palladium(O) was then added to the mixture, and the mixture was stirred vigorously at 90 °C for 36 h. After cooling to room temperature, the mixture was quenched with water, extracted three times with dichloromethane, and the combined organic phases were washed with water and saturated brine, dried over anhydrous magnesium sulfate (MgSO₄), and the organic phase was evaporated. The residue was treated with n-hexane / dichloromethane (V₂O₃ / V₂O₃) solution. hexane V CH2Cl2 Using a 3:1 ratio as the eluent, the product 1-([1,1'-biphenyl]-3-yl)-7-(tert-butyl) was further purified by column chromatography with a yield of 76.5%. The synthetic route is shown below.

[0080]

[0081] Figure 3 The 1-([1,1'-biphenyl]-3-yl)-7-tert-butyl)pyrene obtained in this embodiment 1 H NMR spectrum, Figure 4 The HRMS plot of 1-([1,1'-biphenyl]-3-yl)-7-tert-butyl)pyrene obtained in this embodiment is shown below. Figure 3-4 It can be seen that 1-([1,1'-biphenyl]-3-yl)-7-tert-butyl)pyrene was successfully prepared.

[0082] Example 3: Preparation of 1-([1,1'-biphenyl]-2-yl)-7-tert-butyl)pyrene

[0083] In a double-necked round-bottom flask, 7-tert-butyl-1-bromopyrene (1.0 eq), 2-biphenylboronic acid (1.1 eq), and K₂CO₃ (2.9 eq) were dissolved in a mixture of toluene, ethanol, and H₂O under a N₂ atmosphere and stirred at room temperature for 5 minutes. Tetra(triphenylphosphine)palladium (0) was then added to the mixture, and the mixture was stirred vigorously at 90 °C for 36 h. After cooling to room temperature, the mixture was quenched with water, extracted three times with dichloromethane, and the combined organic phases were washed with water and saturated brine, dried over anhydrous magnesium sulfate (MgSO₄), and the organic phase was evaporated. The residue was treated with n-hexane / dichloromethane (V₂H₂O) solution. hexane V CH2Cl2 Using a 3:1 ratio as the eluent, the product 1-([1,1'-biphenyl]-2-yl)-7-(tert-butyl) was further purified by column chromatography with a yield of 79.0%. The synthetic route is shown below.

[0084]

[0085] Figure 5The 1-([1,1'-biphenyl]-2-yl)-7-tert-butyl)pyrene obtained in this embodiment 1 H NMR spectrum, Figure 6 The HRMS plot of 1-([1,1'-biphenyl]-2-yl)-7-tert-butyl)pyrene obtained in this embodiment is shown below. Figure 5-6 It can be seen that 1-([1,1'-biphenyl]-2-yl)-7-tert-butyl)pyrene was successfully prepared.

[0086] Example 4: Preparation of 1-([1,1'-biphenyl]-4-yl)-3-bromo-7-(tert-butyl)pyrene

[0087] In a double-necked round-bottom flask, 1-([1,1'-biphenyl]-4-yl)-7-(tert-butyl)pyrene (1.0 eq) and benzyltrimethylammonium tribromide (1.2 eq) were dissolved in an ultra-dry dichloromethane mixture under a N2 atmosphere and stirred vigorously at 40 °C for 36 h. After cooling to room temperature, the mixture was quenched with water, extracted three times with dichloromethane, and the combined organic phases were washed with water and saturated brine, dried over anhydrous magnesium sulfate (MgSO4), and the organic phase was evaporated. The residue was treated with n-hexane / dichloromethane (V... hexane V CH2Cl2 Using a 3:1 ratio as the eluent, the product 1-([1,1'-biphenyl]-4-yl)-3-bromo-7-(tert-butyl)pyrene was further purified by column chromatography with a yield of 78.8%. The synthetic route is shown in the following formula.

[0088]

[0089] Figure 7 The 1-([1,1'-biphenyl]-4-yl)-3-bromo-7-(tert-butyl)pyrene obtained in this embodiment 1 H NMR spectrum, Figure 8 The HRMS plot of 1-([1,1'-biphenyl]-4-yl)-3-bromo-7-(tert-butyl)pyrene obtained in this embodiment is shown below. Figure 7-8 It can be seen that 1-([1,1'-biphenyl]-4-yl)-3-bromo-7-(tert-butyl)pyrene was successfully prepared.

[0090] Example 5: Preparation of 1-([1,1'-biphenyl]-3-yl)-3-bromo-7-(tert-butyl)pyrene

[0091] In a double-necked round-bottom flask, 1-([1,1'-biphenyl]-3-yl)-7-(tert-butyl)pyrene (1.0 eq) and benzyltrimethylammonium tribromide (1.2 eq) were dissolved in an ultra-dry dichloromethane mixture under a nitrogen atmosphere and stirred vigorously at 40 °C for 36 h. After cooling to room temperature, the mixture was quenched with water, extracted three times with dichloromethane, and the combined organic phases were washed with water and saturated brine, dried over anhydrous magnesium sulfate (MgSO4), and the organic phase was evaporated. The residue was treated with n-hexane / dichloromethane (V... hexane V CH2Cl2 Using a 3:1 ratio as the eluent, the target product 1-([1,1'-biphenyl]-3-yl)-3-bromo-7-(tert-butyl)pyrene was further purified by column chromatography with a yield of 79.9%. The synthetic route is shown below.

[0092]

[0093] Figure 9 The 1-([1,1'-biphenyl]-3-yl)-3-bromo-7-(tert-butyl)pyrene obtained in this embodiment 1 H NMR spectrum, Figure 10 The HRMS plot of 1-([1,1'-biphenyl]-3-yl)-3-bromo-7-(tert-butyl)pyrene obtained in this embodiment is shown below. Figure 9-10 It can be seen that 1-([1,1'-biphenyl]-3-yl)-3-bromo-7-(tert-butyl)pyrene was successfully prepared.

[0094] Example 6: Preparation of 1-([1,1'-biphenyl]-2-yl)-3-bromo-7-(tert-butyl)pyrene

[0095] In a double-necked round-bottom flask, 1-([1,1'-biphenyl]-2-yl)-7-(tert-butyl)pyrene (1.0 eq) and benzyltrimethylammonium tribromide (1.2 eq) were dissolved in an ultra-dry dichloromethane mixture under a nitrogen atmosphere and stirred vigorously at 40 °C for 36 h. After cooling to room temperature, the mixture was quenched with water, extracted three times with dichloromethane, and the combined organic phases were washed with water and saturated brine, dried over anhydrous magnesium sulfate (MgSO4), and the organic phase was evaporated. The residue was treated with n-hexane / dichloromethane (V... hexane V CH2Cl2 Using a 3:1 ratio as the eluent, the product 1-([1,1'-biphenyl]-2-yl)-3-bromo-7-(tert-butyl)pyrene was further purified by column chromatography with a yield of 80.9%. The synthetic route is shown below.

[0096]

[0097] Figure 11The 1-([1,1'-biphenyl]-2-yl)-3-bromo-7-(tert-butyl)pyrene obtained in this embodiment 1 H NMR spectrum, Figure 12 The HRMS plot of 1-([1,1'-biphenyl]-2-yl)-3-bromo-7-(tert-butyl)pyrene obtained in this embodiment is shown below. Figure 11-12 It can be seen that 1-([1,1'-biphenyl]-2-yl)-3-bromo-7-(tert-butyl)pyrene was successfully prepared.

[0098] Example 7: Preparation of 4-(3-(1,1'-biphenyl)-4-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline (3a)

[0099] In a double-necked round-bottom flask, 1-([1,1'-biphenyl]-4-yl)-3-bromo-7-(tert-butyl)pyrene (1.0 eq), triphenylamine 4-borate (1.3 eq), and K₂CO₃ (7.07 eq) were dissolved in a mixture of toluene, ethanol, and water under a nitrogen atmosphere and stirred at room temperature for 5 minutes. Tetra(triphenylphosphine)palladium(O)(Pd(PPh₃)₄ was then added to the mixture, and the mixture was vigorously stirred at 90 °C for 36 h. After cooling to room temperature, the mixture was quenched with water, extracted three times with dichloromethane, and the combined organic phases were washed with water and saturated brine, dried over anhydrous magnesium sulfate (MgSO₄), and the organic phase was evaporated. The residue was treated with n-hexane / dichloromethane (V₂H₂O) solution. hexane V CH2Cl2 Using a 5:1 ratio as the eluent, the product 4-(3-(1,1'-biphenyl)-4-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline was further purified by column chromatography with a yield of 78.6%. The synthetic route is shown in the following formula.

[0100]

[0101] Figure 13 The 4-(3-(1,1'-biphenyl)-4-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline obtained in this embodiment 1 H NMR spectrum, Figure 14 The HRMS plot of 4-(3-(1,1'-biphenyl)-4-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline obtained in this embodiment is shown below. Figure 13-14 It can be seen that 4-(3-(1,1'-biphenyl)-4-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline was successfully prepared.

[0102] Example 8: Preparation of 4-(3-(1,1'-biphenyl)-3-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline (3b)

[0103] In a double-necked round-bottom flask, 1-([1,1'-biphenyl]-3-yl)-3-bromo-7-(tert-butyl)pyrene (1.0 eq), triphenylamine 4-borate (1.3 eq), and K₂CO₃ (7.07 eq) were dissolved in a mixture of toluene, ethanol, and water under a nitrogen atmosphere and stirred at room temperature for 5 minutes. Tetra(triphenylphosphine)palladium(O)(Pd(PPh₃)₄ was then added to the mixture, and the mixture was vigorously stirred at 90 °C for 36 h. After cooling to room temperature, the mixture was quenched with water, extracted three times with dichloromethane, and the combined organic phases were washed with water and saturated brine, dried over anhydrous magnesium sulfate (MgSO₄), and the organic phase was evaporated. The residue was treated with n-hexane / dichloromethane (V₂H₂O) solution. hexane V CH2Cl2 The product 4-(3-(1,1'-biphenyl)-3-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline was obtained by column chromatography with a yield of 77.6% using a 5:1 ratio as the eluent. The synthetic route is shown in the following formula.

[0104]

[0105] Figure 15 The 4-(3-(1,1'-biphenyl)-3-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline obtained in this embodiment 1 H NMR spectrum, Figure 16 The HRMS plot of 4-(3-(1,1'-biphenyl)-3-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline obtained in this embodiment is shown below. Figure 15-16 It can be seen that 4-(3-(1,1'-biphenyl)-3-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline was successfully prepared.

[0106] Example 9: Preparation of 4-(3-(1,1'-biphenyl)-2-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline (3c)

[0107] In a double-necked round-bottom flask, 1-([1,1'-biphenyl]-2-yl)-3-bromo-7-(tert-butyl)pyrene (1.0 eq), triphenylamine 4-borate (1.3 eq), and K₂CO₃ (7.07 eq) were dissolved in a mixture of toluene, ethanol, and water under a nitrogen atmosphere and stirred at room temperature for 5 minutes. Tetra(triphenylphosphine)palladium(O)(Pd(PPh₃)₄ was then added to the mixture, and the mixture was vigorously stirred at 90 °C for 36 h. After cooling to room temperature, the mixture was quenched with water, extracted three times with dichloromethane, and the combined organic phases were washed with water and saturated brine, dried over anhydrous magnesium sulfate (MgSO₄), and the organic phase was evaporated. The residue was treated with n-hexane / dichloromethane (V₂H₂O) solution. hexane VCH2Cl2 The product 4-(3-(1,1'-biphenyl)-2-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline was obtained by column chromatography with a yield of 79.8% using a 5:1 ratio as the eluent. The synthetic route is shown in the following formula.

[0108]

[0109] Figure 17 The 4-(3-(1,1'-biphenyl)-2-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline obtained in this embodiment 1 H NMR spectrum, Figure 18 The HRMS plot of 4-(3-(1,1'-biphenyl)-2-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline obtained in this embodiment is shown below. Figure 17-18 It can be seen that 4-(3-(1,1'-biphenyl)-2-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline was successfully prepared.

[0110] Example 10: Preparation of 1-(1,1'-biphenyl)-2-yl)-7-tert-butyl-3-(4-(1,2,2-triphenylvinyl)phenyl)pyrene (3d)

[0111] In a double-necked round-bottom flask, 1-([1,1'-biphenyl]-2-yl)-3-bromo-7-(tert-butyl)pyrene (1.0 eq), 1-(4-phenylboronic acid pinacol ester)-1,2,2-triphenylethylene (1.3 eq), and K₂CO₃ (7.07 eq) were dissolved in a mixture of toluene, ethanol, and water under a nitrogen atmosphere and stirred at room temperature for 5 minutes. Tetra(triphenylphosphine)palladium(O)(Pd(PPh₃)₄ was then added to the mixture, and the mixture was vigorously stirred at 90 °C for 36 h. After cooling to room temperature, the mixture was quenched with water, extracted three times with dichloromethane, and the combined organic phases were washed with water and saturated brine, dried over anhydrous magnesium sulfate (MgSO₄), and the organic phase was evaporated. The residue was treated with n-hexane / dichloromethane (V₂O₃ / V₂O₃) solution. hexane V CH2Cl2 Using a 5:1 ratio as the eluent, the product 1-(1,1'-biphenyl)-2-yl)-7-tert-butyl-3-(4-(1,2,2-triphenylvinyl)phenyl)pyrene was further purified by column chromatography with a yield of 80.0%. The synthetic route is shown in the following formula.

[0112]

[0113] Figure 19 The 1-([1,1'-biphenyl]-2-yl)-7-tert-butyl-3-(4-(1,2,2-triphenylvinyl)phenyl)pyrene obtained in this embodiment 1H NMR spectrum, Figure 20 The HRMS plot of 1-([1,1'-biphenyl]-2-yl)-7-tert-butyl-3-(4-(1,2,2-triphenylvinyl)phenyl)pyrene obtained in this embodiment is shown below. Figures 19-20 It can be seen that 1-([1,1'-biphenyl]-2-yl)-7-tert-butyl-3-(4-(1,2,2-triphenylvinyl)phenyl)pyrene was successfully prepared.

[0114] Example 11: Preparation of 3-(3-(1,1'-biphenyl)-4-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline (3e)

[0115] In a double-necked round-bottom flask, 1-([1,1'-biphenyl]-4-yl)-3-bromo-7-(tert-butyl)pyrene (1.0 eq), pinacol triphenylamine-3-boronate (1.3 eq), and K₂CO₃ (7.07 eq) were dissolved in a mixture of toluene, ethanol, and water under a nitrogen atmosphere and stirred at room temperature for 5 minutes. Tetra(triphenylphosphine)palladium(O)(Pd(PPh₃)₄ was then added to the mixture, and the mixture was stirred vigorously at 90 °C for 36 h. After cooling to room temperature, the mixture was quenched with water, extracted three times with dichloromethane, and the combined organic phases were washed with water and saturated brine, dried over anhydrous magnesium sulfate (MgSO₄), and the organic phase was evaporated. The residue was treated with n-hexane / dichloromethane (V₂H₂O) solution. hexane V CH2Cl2 The product 3-(3-(1,1'-biphenyl)-4-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline was obtained by column chromatography with a yield of 78.9% using a 5:1 ratio as the eluent. The synthetic route is shown in the following formula.

[0116]

[0117] Figure 21 The 3-(3-(1,1'-biphenyl)-4-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline obtained in this embodiment 1 H NMR spectrum, Figure 22 The HRMS plot of 3-(3-(1,1'-biphenyl)-4-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline obtained in this embodiment is shown below. Figure 21-22 It can be seen that 3-(3-(1,1'-biphenyl)-4-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline was successfully prepared.

[0118] Example 12: Preparation of 3-(3-(1,1'-biphenyl)-3-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline (3f)

[0119] In a double-necked round-bottom flask, 1-([1,1'-biphenyl]-3-yl)-3-bromo-7-(tert-butyl)pyrene (1.0 eq), pinacol triphenylamine-3-boronate (1.3 eq), and K₂CO₃ (7.07 eq) were dissolved in a mixture of toluene, ethanol, and water under a nitrogen atmosphere and stirred at room temperature for 5 minutes. Tetra(triphenylphosphine)palladium(O)(Pd(PPh₃)₄ was then added to the mixture, and the mixture was vigorously stirred at 90 °C for 36 h. After cooling to room temperature, the mixture was quenched with water, extracted three times with dichloromethane, and the combined organic phases were washed with water and saturated brine, dried over anhydrous magnesium sulfate (MgSO₄), and the organic phase was evaporated. The residue was treated with n-hexane / dichloromethane (V₂H₂O) solution. hexane V CH2Cl2 The product 3-(3-(1,1'-biphenyl)-3-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline was obtained by column chromatography with a yield of 81.3% using a 5:1 ratio as the eluent. The synthetic route is shown in the following formula.

[0120]

[0121] Figure 23 The 3-(3-(1,1'-biphenyl)-3-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline obtained in this embodiment 1 H NMR spectrum, Figure 23-24 The HRMS plot of 3-(3-(1,1'-biphenyl)-3-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline obtained in this embodiment is shown below. Figure 23-24 It can be seen that 3-(3-(1,1'-biphenyl)-3-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline was successfully prepared.

[0122] Example 13: Preparation of 3-(3-(1,1'-biphenyl)-2-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline (3g)

[0123] In a double-necked round-bottom flask, 1-([1,1'-biphenyl]-2-yl)-3-bromo-7-(tert-butyl)pyrene (1.0 eq), pinacol triphenylamine-3-boronate (1.3 eq), and K₂CO₃ (7.07 eq) were dissolved in a mixture of toluene, ethanol, and water under a nitrogen atmosphere and stirred at room temperature for 5 minutes. Tetra(triphenylphosphine)palladium(O)(Pd(PPh₃)₄ was then added to the mixture, and the mixture was vigorously stirred at 90 °C for 36 h. After cooling to room temperature, the mixture was quenched with water, extracted three times with dichloromethane, and the combined organic phases were washed with water and saturated brine, dried over anhydrous magnesium sulfate (MgSO₄), and the organic phase was evaporated. The residue was treated with n-hexane / dichloromethane (V₂H₂O) solution. hexane VCH2Cl2 The product 3-(3-(1,1'-biphenyl)-2-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline was obtained by column chromatography with a yield of 79.3% using a 5:1 ratio as the eluent. The synthetic route is shown in the following formula.

[0124]

[0125] Figure 25 The 3-(3-(1,1'-biphenyl)-2-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline obtained in this embodiment 1 H NMR spectrum, Figure 26 The HRMS plot of 3-(3-(1,1'-biphenyl)-2-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline obtained in this embodiment is shown below. Figure 25-26 It can be seen that 3-(3-(1,1'-biphenyl)-2-yl)-7-tert-butylpyrene-1-yl)-N,N-diphenylaniline was successfully prepared.

[0126] Example 14: Preparation of 1-(1,1'-biphenyl)-3-yl)-7-tert-butyl-3-(4-(1,2,2-triphenylvinyl)phenyl)pyrene (3h)

[0127] In a double-necked round-bottom flask, 1-([1,1'-biphenyl]-3-yl)-3-bromo-7-(tert-butyl)pyrene (1.0 eq), 1-(4-phenylboronic acid pinacol ester)-1,2,2-triphenylethylene (1.3 eq), and K2CO3 (7.07 eq) were dissolved in a mixture of toluene, ethanol, and water under a nitrogen atmosphere and stirred at room temperature for 5 minutes. Tetra(triphenylphosphine)palladium(0)(Pd(PPh3)4)4 was then added to the mixture, and the mixture was vigorously stirred at 90 °C for 36 h. After cooling to room temperature, the mixture was quenched with water, extracted three times with dichloromethane, and the combined organic phases were washed with water and saturated brine, dried over anhydrous magnesium sulfate (MgSO4), and the organic phase was evaporated. The residue was treated with n-hexane / dichloromethane (V... hexane V CH2Cl2 Using a 5:1 ratio as the eluent, the product 1-(1,1'-biphenyl)-3-yl)-7-tert-butyl-3-(4-(1,2,2-triphenylvinyl)phenyl)pyrene was further purified by column chromatography with a yield of 78.6%. The synthetic route is shown in the following formula.

[0128]

[0129] Figure 27 The 1-([1,1'-biphenyl]-3-yl)-7-tert-butyl-3-(4-(1,2,2-triphenylvinyl)phenyl)pyrene obtained in this embodiment 1H NMR spectrum, Figure 28 The HRMS plot of 1-([1,1'-biphenyl]-3-yl)-7-tert-butyl-3-(4-(1,2,2-triphenylvinyl)phenyl)pyrene obtained in this embodiment is shown below. Figure 27-28 It can be seen that 1-([1,1'-biphenyl]-3-yl)-7-tert-butyl-3-(4-(1,2,2-triphenylvinyl)phenyl)pyrene was successfully prepared.

[0130] Example 15: Preparation of 1,3-([1,1'-biphenyl]-3-yl)-7-(tert-butyl)pyrene (3i)

[0131] In a double-necked round-bottom flask, 1-([1,1'-biphenyl]-3-yl)-3-bromo-7-(tert-butyl)pyrene (1.0 eq), 3-biphenylboronic acid (1.3 eq), and K₂CO₃ (7.07 eq) were dissolved in a mixture of toluene, ethanol, and water under a nitrogen atmosphere and stirred at room temperature for 5 minutes. Tetra(triphenylphosphine)palladium(O)(Pd(PPh₃)₄ was then added to the mixture, and the mixture was vigorously stirred at 90 °C for 36 h. After cooling to room temperature, the mixture was quenched with water, extracted three times with dichloromethane, and the combined organic phases were washed with water and saturated brine, dried over anhydrous magnesium sulfate (MgSO₄), and the organic phase was evaporated. The residue was treated with n-hexane / dichloromethane (V₂H₂O) solution. hexane V CH2Cl2 Using a 5:1 ratio as the eluent, the product 1,3-([1,1'-biphenyl]-3-yl)-7-(tert-butyl)pyrene was further purified by column chromatography with a yield of 77.9%. The synthetic route is shown below.

[0132]

[0133] Figure 29 The 1,3-([1,1'-biphenyl]-3-yl)-7-(tert-butyl)pyrene obtained in this embodiment 1 H NMR spectrum, Figure 30 The HRMS plot of 1,3-([1,1'-biphenyl]-3-yl)-7-(tert-butyl)pyrene obtained in this embodiment is shown below. Figures 29-30 It can be seen that 1,3-([1,1'-biphenyl]-3-yl)-7-(tert-butyl)pyrene was successfully prepared.

[0134] The above embodiments are preferred embodiments of the present invention, but the embodiments of the present invention are not limited to the above embodiments. Any changes, modifications, substitutions, combinations, or simplifications made without departing from the spirit and principle of the present invention shall be considered equivalent substitutions and shall be included within the protection scope of the present invention.

Claims

1. A narrowband pyrene-based blue light-emitting material, characterized in that: The narrowband-emitting pyrene-based blue light material has the structure shown in formula (1): When R1 is When R2 is When R1 is When R2 is When R1 is When R2 is 2. The method for preparing a narrowband pyrene-based blue light-emitting material according to claim 1, characterized in that... The following steps are included: (1) Under an inert atmosphere, the 7-tert-butyl-1-bromopyrene intermediate was added to a mixed solution of arylboronic acid and its derivatives, an inorganic base, a solvent, and a palladium catalyst. The mixture was stirred at 90℃~100℃ for 24~48h to carry out a metal-catalyzed coupling reaction. Functional substitution was performed at the 1-site of pyrene to prepare the precursor 7-tert-butyl-1-R1 group pyrene. The precursor 7-tert-butyl-1-R1 group pyrene has the structure shown in formula (2) below: Wherein, R1 is (2) Under an inert atmosphere, the precursor 7-tert-butyl-1-R1 pyrene obtained in step (1) is added to a mixed solution of brominating agent and solvent, and the mixture is stirred at 25℃~50℃ for 12~48h to carry out a bromination reaction. A halogenated substitution is performed at the 3-site of pyrene to prepare a 7-tert-butyl-1-R1 group-substituted-3-halogenated pyrene intermediate. The 7-tert-butyl-1-R1 group-substituted-3-halogenated pyrene intermediate has the structure shown in formula (3) below: R3 is one of fluorine, chlorine, bromine or iodine; (3) Under an inert atmosphere, the 3-halogenated pyrene intermediate with 7-tert-butyl-1-R1 group substituted is added to a mixed solution of arylboronic acid and its derivatives, inorganic base, solvent and palladium catalyst, and stirred at 90℃~100℃ for 24~48h to carry out metal-catalyzed coupling reaction, and functionalized substitution is performed at the 3-site of pyrene to prepare narrowband pyrene blue light material.

3. The preparation method according to claim 2, characterized in that: The inert atmosphere in step (1) is one or both of nitrogen and argon; the palladium catalyst is one or more of tetra(triphenylphosphine)palladium, palladium acetate, or bis(triphenylphosphine)palladium dichloride; the inorganic base is one or more of potassium carbonate, sodium carbonate, sodium bicarbonate, and potassium bicarbonate; the arylboronic acid and its derivatives are 2-biphenylboronic acid, 3-biphenylboronic acid, or 4-biphenylboronic acid; the molar ratio of the 7-tert-butyl-1-bromopyrene intermediate, arylboronic acid and its derivatives, inorganic base, and palladium catalyst is 1:(1-3):(2-10):(1-5); the solvent is a mixture of water, ethanol, and toluene in a volume ratio of (1-5):(1-5):

1.

4. The preparation method according to claim 2, characterized in that: The inert atmosphere in step (3) is one or both of nitrogen and argon; the palladium catalyst is one or more of tetra(triphenylphosphine)palladium, palladium acetate, or bis(triphenylphosphine)palladium dichloride; the inorganic base is one or more of potassium carbonate, sodium carbonate, sodium bicarbonate, and potassium bicarbonate; the arylboronic acid and its derivatives are triphenylamine-3-boronic acid pinacol ester, 4-boronic acid triphenylamine, 1-(4-phenylboronic acid pinacol ester)-1,2,2-triphenylethylene, or 3-biphenylboronic acid; the molar ratio of the 7-tert-butyl-1-R1 group-substituted 3-halogenated pyrene intermediate, arylboronic acid and its derivatives, inorganic base, and palladium catalyst is 1:(1-3):(2-10):(1-5); the solvent is a mixture of water, ethanol, and toluene in a volume ratio of (1-5):(1-5):

1.

5. The preparation method according to claim 2, characterized in that: The inert atmosphere in step (2) is nitrogen or argon; the brominating agent is one or more of bromine water, NBS, BTMABr3, chlorine, fluorine, and iodine; the solvent is one or more of dichloromethane, tetrahydrofuran, water, and ethanol; and the molar ratio of the precursor 7-tert-butyl-1-R1 pyrene to the brominating agent is 1:(1-5).

6. The application of the narrowband pyrene-based blue light-emitting material according to claim 1 in organic optoelectronic devices.

7. The application according to claim 6, characterized in that: The organic optoelectronic devices include organic light-emitting diodes, organic field-effect transistors, solar cells, or organic lasers.

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