Photo-controllable delayed fluorescence dye and method for preparing the same

Abstract

The application discloses a light-controlled delayed fluorescence dye, and relates to the technical field of photo-functional materials. The light-controlled delayed fluorescence dye has a structural formula as shown in formula I. The application can excite a light reaction through visible light, and improves light response speed and fluorescence quantum yield.

Description

Technical Field

[0001] This application relates to the field of optical functional materials technology, specifically to a light-controlled delayed fluorescence dye and its preparation method. Background Technology

[0002] Photochromic dyes are a class of functional dyes that undergo reversible isomerization reactions when excited by two or more different wavelengths of light. During photoisomerization, the dye's optical properties, such as color, fluorescence, and phosphorescence, change. Currently, the changes in fluorescence signals before and after photochromism are widely used in fields such as information encryption and bioimaging. However, existing light-controlled fluorescent dyes still have the following drawbacks:

[0003] It requires ultraviolet light to excite the photoreaction, which can easily damage materials and organisms, and has limited penetration depth. At the same time, the photoresponse speed is slow and the fluorescence quantum yield is low. Summary of the Invention

[0004] To address the shortcomings of existing technologies, the technical problem solved by this application is: how to improve the photoresponse speed and fluorescence quantum yield without using ultraviolet light to excite the photoreaction.

[0005] To achieve the above objectives, in a first aspect, embodiments of this application provide a light-controlled delayed fluorescence dye, the structural formula of which is shown in Formula I:

[0006]

[0007] Formula I

[0008] In the formula, R1, R2, R3, and R4 represent hydrogen, Cl-C, and C, respectively. 10 Alkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of heterocyclic aryl, halogen, silyl, o-benzylphenyl or cyano;

[0009] R5, R6, R8, and R9 are each one of hydrogen, cyano, trifluoromethyl, or phenyl.

[0010] R7 is hydrogen, cyano, trifluoromethyl, phenyl, and One of them, in which This refers to the connection of the corresponding functional group to other fragments or functional groups in the compound through this site;

[0011] R 10 It is cyano, halogen and C1-C 10 One of the alkyl groups;

[0012] R 11 C6-C, whether substituted or not 30 aryl, substituted or unsubstituted C3-C30 Mixed aromatics;

[0013] R 12 C6-C, whether substituted or not 30 aryl, substituted or unsubstituted C3-C 30 Mixed aromatics;

[0014] X1 is one of S, O, NH and SO2;

[0015] X2 is CR 10-1 Or N; where R 10-1 Halogen, cyano, C1-C6 alkyl, C6-C 10 The aryl group may be surrounded by one, two, or three R groups. 10 -1-1 Replacement C6-C 10 One of the aryl groups, and R 10-1-1 It is one of halogen, cyano, or C1-C6 alkyl;

[0016] X3 is CR 10-2 Or N; where R 10-2 It is hydrogen, halogen, cyano, C1-C6 alkyl, C6-C 10 The aryl group may be surrounded by one, two, or three R groups. 10-2-1 Replacement C6-C 10 One of the aryl groups, and R 10-2-1 It is one of halogen, cyano, or C1-C6 alkyl.

[0017] In conjunction with the first aspect, in one embodiment, the C1-C 10 The alkyl group is at least one selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, and n-decyl.

[0018] The substituted or unsubstituted C6-C 30 The aryl group is at least one selected from the following: substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted indene, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted 9,9'-dialkylfluorenyl, substituted or unsubstituted 9,9'-spirodifluorenyl, substituted or unsubstituted indenefluorenyl, substituted or unsubstituted fluoranyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted peryl, substituted or unsubstituted azulel, and substituted or unsubstituted tetraphenyl; wherein the substituent is at least one selected from tert-butyl and phenyl.

[0019] The substituted or unsubstituted C3-C 30The heterocyclic aryl group is at least one of the following: substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzoselenophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted carbazolyl, substituted or unsubstituted azacarbazolyl, and substituted or unsubstituted benzocarbazolyl; wherein the substituent is at least one of methyl and tert-butyl.

[0020] In conjunction with the first aspect, in one embodiment, the halogen is at least one selected from fluorine, chlorine, bromine, and iodine.

[0021] In conjunction with the first aspect, in one embodiment, the C6-C 10 The aryl group is at least one of phenyl and naphthyl.

[0022] Secondly, embodiments of this application provide a method for preparing a light-controlled delayed fluorescent dye, wherein compound I-1 is mixed with... The compound shown in Formula I was obtained by nucleophilic substitution reaction; the structural formula of compound I-1 is shown in Formula I-1:

[0023]

[0024] Formula I-1

[0025] Its synthetic route is as follows:

[0026] ;

[0027] In the formula, R1, R2, R3, and R4 represent hydrogen, Cl-C, and C, respectively. 10 Alkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of heterocyclic aryl, halogen, silyl, o-benzylphenyl or cyano;

[0028] R5, R6, R8, and R9 are each one of hydrogen, cyano, trifluoromethyl, or phenyl.

[0029] R7 is hydrogen, cyano, trifluoromethyl, phenyl, and One of them;

[0030] R 10 It is cyano, halogen and C1-C 10 One of the alkyl groups;

[0031] R 11 C6-C, whether substituted or not 30 aryl, substituted or unsubstituted C3-C 30 Mixed aromatics;

[0032] R 12 C6-C, whether substituted or not 30aryl, substituted or unsubstituted C3-C 30 Mixed aromatics;

[0033] X1 is one of S, O, NH and SO2;

[0034] X2 is CR 10-1 Or N; where R 10-1 Halogen, cyano, C1-C6 alkyl, C6-C 10 The aryl group may be surrounded by one, two, or three R groups. 10 -1-1 Replacement C6-C 10 One of the aryl groups, and R 10-1-1 It is one of halogen, cyano, or C1-C6 alkyl;

[0035] X3 is CR 10-2 Or N; where R 10-2 It is hydrogen, halogen, cyano, C1-C6 alkyl, C6-C 10 The aryl group may be surrounded by one, two, or three R groups. 10-2-1 Replacement C6-C 10 One of the aryl groups, and R 10-2-1 It is one of halogen, cyano, or C1-C6 alkyl.

[0036] Compared with the prior art, the advantages of this application are:

[0037] I. Using indole as the core structure of the photochromic diarylethylene bridge, and indole acting as an electron donor, different electron-withdrawing groups are attached to the indole nitrogen as electron acceptors to form a photocontrollable thermally activated delayed fluorescent dye. This dye not only has a very narrow singlet-triple band gap, but also absorbs in a longer wavelength region, even in the visible light region. It can act as a triplet sensitizer, achieving visible light excitation photochromism of diarylethylene through triplet-triple energy transfer. At the same time, the closed ring of diarylethylene absorbs in the visible light region, which can overlap with the fluorescence emission wavelength region of the thermally activated delayed fluorescent dye, thereby achieving the regulation of the fluorescence of the thermally activated delayed fluorescent dye by the photochromic reaction. In addition, by adjusting the electron-withdrawing ability of the electron acceptor and the different connection positions of the groups in the thermally activated delayed fluorescent dye, long-wavelength excitation photochromic performance and high-efficiency luminescence performance can be obtained.

[0038] Second, it has efficient delayed fluorescence performance, long delayed fluorescence lifetime, significantly improved fluorescence quantum yield, good fatigue resistance, and strong and easy-to-detect fluorescence signal; at the same time, the fluorescence emission peak can be regulated by adjusting the unit structure of the thermally activated delayed fluorescent dye, which solves the problem of wide emission peak of traditional dyes and improves the accuracy of optical signal. Attached Figure Description

[0039] To more clearly illustrate the technical solutions in the embodiments of this application, the accompanying drawings used in the description of the embodiments will be briefly introduced below. Obviously, the accompanying drawings described below are only some embodiments of this application. For those skilled in the art, other drawings can be obtained based on these drawings without creative effort.

[0040] Figure 1 The above is the 1H NMR spectrum of compound 3 in the embodiments of this application;

[0041] Figure 2 The fluorescence spectrum and delayed fluorescence lifetime test table of compound 3 in the embodiments of this application are shown.

[0042] Figure 3 This is a fatigue resistance test of the photochromic properties of compound 3 in the embodiments of this application. Detailed Implementation

[0043] To make the objectives, technical solutions, and advantages of the embodiments of this application clearer, the technical solutions of the embodiments of this application will be clearly and completely described below with reference to the accompanying drawings. Obviously, the described embodiments are only some embodiments of this application, not all embodiments. Based on the embodiments of this application, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of this application.

[0044] The flowchart shown in the attached diagram is for illustrative purposes only and does not necessarily include all content and operations / steps, nor does it necessarily have to be performed in the order described. For example, some operations / steps can be broken down, combined, or partially merged, so the actual execution order may change depending on the actual situation.

[0045] To make the objectives, technical solutions, and advantages of this application clearer, the embodiments of this application will be described in further detail below with reference to the accompanying drawings.

[0046] In a first aspect, embodiments of this application provide a light-controlled delayed fluorescent dye, the structural formula of which is shown in Formula I:

[0047]

[0048] Formula I

[0049] In the formula, R1, R2, R3, and R4 represent hydrogen, Cl-C, and C, respectively. 10 Alkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of heterocyclic aryl, halogen, silyl, o-benzylphenyl or cyano;

[0050] R5, R6, R8, and R9 are each one of hydrogen, cyano, trifluoromethyl, or phenyl.

[0051] R7 is hydrogen, cyano, trifluoromethyl, phenyl, and One of them;

[0052] R 10 It is cyano, halogen and C1-C 10 One of the alkyl groups;

[0053] R 11 C6-C, whether substituted or not 30 aryl, substituted or unsubstituted C3-C 30 Mixed aromatics;

[0054] R 12 C6-C, whether substituted or not 30 aryl, substituted or unsubstituted C3-C 30 Mixed aromatics;

[0055] X1 is one of S, O, NH and SO2;

[0056] X2 is CR 10-1 Or N; where R 10-1 Halogen, cyano, C1-C6 alkyl, C6-C 10 The aryl group may be surrounded by one, two, or three R groups. 10 -1-1 Replacement C6-C 10 One of the aryl groups, and R 10-1-1 It is one of halogen, cyano, or C1-C6 alkyl;

[0057] X3 is CR 10-2 Or N; where R 10-2 It is hydrogen, halogen, cyano, C1-C6 alkyl, C6-C 10 The aryl group may be surrounded by one, two, or three R groups. 10-2-1 Replacement C6-C 10 One of the aryl groups, and R 10-2-1 It is one of halogen, cyano, or C1-C6 alkyl.

[0058] Therefore, indole is used as the core structure of the photochromic diarylethylene bridge. Indole also acts as an electron donor, and different electron-withdrawing groups are attached to the indole nitrogen as electron acceptors to form a photocontrollable thermally activated delayed fluorescent dye. This dye not only has a very narrow singlet-triple band gap, but also absorbs in a longer wavelength region and even in the visible light region. It can act as a triplet sensitizer, realizing visible light excitation photochromism of diarylethylene through triplet-triple energy transfer. At the same time, the closed ring of diarylethylene absorbs in the visible light region, which can overlap with the fluorescence emission wavelength region of the thermally activated delayed fluorescent dye, thereby realizing the regulation of the fluorescence of the thermally activated delayed fluorescent dye by the photochromic reaction. In addition, by adjusting the electron-withdrawing ability of the electron acceptor in the thermally activated delayed fluorescent dye unit and the different connection positions of the groups, long-wavelength excitation photochromic performance and high-efficiency luminescence performance can be obtained.

[0059] In one embodiment, the above C1-C 10 The alkyl group is at least one selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, and n-decyl.

[0060] The substituted or unsubstituted C6-C 30 The aryl group is at least one selected from the following: substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted indene, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted 9,9'-dialkylfluorenyl, substituted or unsubstituted 9,9'-spirodifluorenyl, substituted or unsubstituted indenefluorenyl, substituted or unsubstituted fluoranyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted peryl, substituted or unsubstituted azulel, and substituted or unsubstituted tetraphenyl; wherein the substituent is at least one selected from tert-butyl and phenyl.

[0061] The substituted or unsubstituted C3-C 30 The heterocyclic aryl group is at least one of the following: substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzoselenophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted carbazolyl, substituted or unsubstituted azacarbazolyl, and substituted or unsubstituted benzocarbazolyl; wherein the substituent is at least one of methyl and tert-butyl.

[0062] In one embodiment, the halogen is at least one of fluorine, chlorine, bromine and iodine.

[0063] In one embodiment, the above-mentioned C6-C 10 The aryl group is at least one of phenyl and naphthyl.

[0064] Based on this, embodiments of this application provide a light-controlled delayed fluorescence dye with the following structural formulas: compound 3, compound 4, compound 5, compound 6, compound 7, compound 8, compound 9, compound 10, compound 11, compound 12, compound 13, and compound 14, respectively.

[0065] .

[0066] Secondly, embodiments of this application provide a method for preparing a light-controlled delayed fluorescent dye, used to achieve the preparation of the light-controlled delayed fluorescent dye provided in the first aspect. The steps of this method for preparing the light-controlled delayed fluorescent dye include:

[0067] Compound I-1 and The compound shown in Formula I was obtained by nucleophilic substitution reaction; the structural formula of compound I-1 is shown in Formula I-1:

[0068]

[0069] Formula I-1

[0070] Its synthetic route is as follows:

[0071] .

[0072] Based on this, taking compound 3 as an example, a light-controlled delayed fluorescent dye was prepared. The preparation process includes:

[0073] In a 250 mL two-necked round-bottom flask, add compound 1 (2.66 g, 12.15 mmol), o-iodoaniline (2 g, 8.1 mmol), palladium acetate (0.092 g, 0.405 mmol), tricyclohexylphosphine (0.45 g, 1.62 mmol) and potassium carbonate (2.8 g, 20.25 mmol), respectively.

[0074] An N-methylpyrrolidone solution (81 mL) was added under N2 environment, and the mixture was heated and stirred under reflux at 130 °C for 12 h. The N-methylpyrrolidone was then removed by decompression distillation, and the crude product was separated by silica gel column chromatography.

[0075] After dissolving the crude product in dichloromethane, it was washed with n-hexane to obtain a white solid compound 2 (2.27 g, 83%).

[0076] In a 50 mL round-bottom flask, compound 2 (337 mg, 1 mmol), 2-(4-fluorophenyl)-4,6-diphenyl-1,3,5-triazine (309.37 mg, 1 mmol), cesium carbonate (651 mg, 2 mmol), and dimethyl sulfoxide solvent (8 mL) were added. After reacting at 180 °C for 5 h, the crude product (n-hexane: dichloromethane = 10:1) was separated by silica gel column chromatography. After the solvent was evaporated to dryness, the product was washed with diethyl ether, and the solid was collected. After washing several times, a white solid compound 3 (400 mg, 67%) was obtained.

[0077] To further explain, the synthetic route for compound 3 is as follows:

[0078] .

[0079] The performance of compound 3 was then tested to verify the performance of the light-controlled delayed fluorescent dye provided in this application. The performance testing methods included:

[0080] exist 1 The compound was subjected to proton NMR spectroscopy under the conditions of 1H NMR (400 MHz, CDCl3), and its proton NMR spectrum is as follows. Figure 1 As shown.

[0081] 0.01 mol of compound 3 was dissolved in 10 mL of dichloromethane solution to obtain a pre-prepared solution with a concentration of 1 μM;

[0082] Take 10 μL of the pre-prepared solution and place it in a quartz cuvette, and add 1 ml of n-hexane solution to obtain a test solution with a concentration of 0.01 μM.

[0083] The test solution underwent ultraviolet absorption testing (UV-2600, SHIMADZU), including:

[0084] The test solution was irradiated with a 410nm LED, and the absorption spectrum and changes in the appearance of the test solution were monitored during the process. The results showed that during irradiation, the absorption peak at 375nm gradually increased and underwent a blue shift, while new absorption peaks appeared in the 405-650nm range. The maximum absorption wavelength of these new peaks was located at 550nm. The color of the compound solution gradually changed from initially colorless to pale purple, indicating that a photo-cyclization reaction occurred at 410nm. After 10 seconds of continuous irradiation, the absorption spectrum remained unchanged, reaching a steady-state, demonstrating a fast photoresponse.

[0085] The test solution was then irradiated with an LED with a wavelength greater than 500 nm. The results showed that the absorption spectrum gradually returned to its initial state, and the color of the test solution also returned from pale purple to its initial state.

[0086] During the process, a fluorescence spectrum was drawn ( Figure 2 Figure a) and the delayed fluorescence lifetime test table ( Figure 2 (Figure b in the middle)

[0087] Finally, the test solution was used alternately with LED irradiation at 410 nm and with LED irradiation at >500 nm. The results are as follows: Figure 3 As shown, after 7 cycles, compound 3 still exhibits relatively good fatigue resistance.

[0088] The above are merely specific embodiments of this application, but the protection scope of this application is not limited thereto. Any person skilled in the art can easily conceive of various equivalent modifications or substitutions within the technical scope disclosed in this application, and these modifications or substitutions should all be covered within the protection scope of this application. Therefore, the protection scope of this application should be determined by the scope of the claims.

Claims

1. A light-controlled delayed fluorescent dye, characterized in that, Its structural formula is shown in Formula I: 2.Formula I In the formula, R1, R2, R3, and R4 represent hydrogen, Cl-C, and C, respectively. 10 Alkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of heterocyclic aryl, halogen, silyl, o-benzylphenyl or cyano; R5, R6, R8, and R9 are each one of hydrogen, cyano, trifluoromethyl, or phenyl. R7 is hydrogen, cyano, trifluoromethyl, phenyl, and One of them; R 10 It is cyano, halogen and C1-C 10 One of the alkyl groups; R 11 C6-C, whether substituted or not 30 aryl, substituted or unsubstituted C3-C 30 Mixed aromatics; R 12 C6-C, whether substituted or not 30 aryl, substituted or unsubstituted C3-C 30 Mixed aromatics; X1 is one of S, O, NH and SO2; X2 is CR 10-1 Or N; where R 10-1 Halogen, cyano, C1-C6 alkyl, C6-C 10 The aryl group may be surrounded by one, two, or three R groups. 10-1-1 Replacement C6-C 10 One of the aryl groups, and R 10-1-1 It is one of halogen, cyano, or C1-C6 alkyl; X3 is CR 10-2 Or N; where R 10-2 It is hydrogen, halogen, cyano, C1-C6 alkyl, C6-C 10 The aryl group may be surrounded by one, two, or three R groups. 10 -2-1 Replacement C6-C 10 One of the aryl groups, and R 10-2-1 It is one of halogen, cyano, or C1-C6 alkyl.

3. The light-controlled delayed fluorescent dye according to claim 1, characterized in that, The C1-C 10 The alkyl group is at least one selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, and n-decyl. The substituted or unsubstituted C6-C 30 The aryl group is at least one selected from the following: substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted indene, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted 9,9'-dialkylfluorenyl, substituted or unsubstituted 9,9'-spirodifluorenyl, substituted or unsubstituted indenefluorenyl, substituted or unsubstituted fluoranyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted peryl, substituted or unsubstituted azulel, and substituted or unsubstituted tetraphenyl; wherein the substituent is at least one selected from tert-butyl and phenyl. The substituted or unsubstituted C3-C 30 The heterocyclic aryl group is at least one of the following: substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzoselenophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted carbazolyl, substituted or unsubstituted azacarbazolyl, and substituted or unsubstituted benzocarbazolyl; wherein the substituent is at least one of methyl and tert-butyl.

4. The light-controlled delayed fluorescent dye according to claim 1, characterized in that, The halogen is at least one of fluorine, chlorine, bromine and iodine.

5. The light-controlled delayed fluorescent dye according to claim 1, characterized in that, The C6-C 10 The aryl group is at least one of phenyl and naphthyl.

6. A method for preparing a light-controlled delayed fluorescent dye, applied to the light-controlled delayed fluorescent dye described in claim 1, characterized in that, Compound I-1 and The compound shown in Formula I was obtained by nucleophilic substitution reaction; the structural formula of compound I-1 is shown in Formula I-1: 7.Formula I-1 Its synthetic route is as follows: ； In the formula, R1, R2, R3, and R4 represent hydrogen, Cl-C, and C, respectively. 10 Alkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 One of heterocyclic aryl, halogen, silyl, o-benzylphenyl or cyano; R5, R6, R8, and R9 are each one of hydrogen, cyano, trifluoromethyl, or phenyl. R7 is hydrogen, cyano, trifluoromethyl, phenyl, and One of them; R 10 It is cyano, halogen and C1-C 10 One of the alkyl groups; R 11 C6-C, whether substituted or not 30 aryl, substituted or unsubstituted C3-C 30 Mixed aromatics; R 12 C6-C, whether substituted or not 30 aryl, substituted or unsubstituted C3-C 30 Mixed aromatics; X1 is one of S, O, NH and SO2; X2 is CR 10-1 Or N; where R 10-1 Halogen, cyano, C1-C6 alkyl, C6-C 10 The aryl group may be surrounded by one, two, or three R groups. 10-1-1 Replacement C6-C 10 One of the aryl groups, and R 10-1-1 It is one of halogen, cyano, or C1-C6 alkyl; X3 is CR 10-2 Or N; where R 10-2 It is hydrogen, halogen, cyano, C1-C6 alkyl, C6-C 10 The aryl group may be surrounded by one, two, or three R groups. 10 -2-1 Replacement C6-C 10 One of the aryl groups, and R 10-2-1 It is one of halogen, cyano, or C1-C6 alkyl.

8. The method for preparing a light-controlled delayed fluorescent dye according to claim 5, characterized in that, The C1-C 10 The alkyl group is at least one selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, and n-decyl. The substituted or unsubstituted C6-C 30 The aryl group is at least one selected from the following: substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted indene, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted 9,9'-dialkylfluorenyl, substituted or unsubstituted 9,9'-spirodifluorenyl, substituted or unsubstituted indenefluorenyl, substituted or unsubstituted fluoranyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted peryl, substituted or unsubstituted azulel, and substituted or unsubstituted tetraphenyl; wherein the substituent is at least one selected from tert-butyl and phenyl. The substituted or unsubstituted C3-C 30 The heterocyclic aryl group is at least one of the following: substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzoselenophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted carbazolyl, substituted or unsubstituted azacarbazolyl, and substituted or unsubstituted benzocarbazolyl; wherein the substituent is at least one of methyl and tert-butyl.

9. The method for preparing a light-controlled delayed fluorescent dye according to claim 5, characterized in that, The halogen is at least one of fluorine, chlorine, bromine and iodine.

10. The light-controlled delayed fluorescent dye and its preparation method according to claim 5, characterized in that, The C6-C 10 The aryl group is at least one of phenyl and naphthyl.

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