Chiral flipping ultra-long room temperature phosphorescent polymer with light activation characteristic and application thereof

Abstract

The invention discloses a chiral upset super-long room temperature phosphorescent polymer with light activation characteristic and application thereof, and belongs to the technical field of organic photoelectric functional materials, the chiral upset super-long room temperature phosphorescent polymer with light activation characteristic provided by the invention is simple in synthesis step and low in preparation cost, and the specific synthesis method is as follows: in a nitrogen environment, the chiral upset super-long room temperature phosphorescent polymer with light activation characteristic is prepared by a one-step synthesis method of the chiral upset super-long room temperature phosphorescent polymer with light activation characteristic. The method comprises the following steps: dissolving R-configuration or S-configuration binaphthalene-diphenylphosphine in N-N dimethylformamide, adding 1-bromopropane, heating and stirring at 120 DEG C for 72 hours, then carrying out reduced pressure distillation and spin drying, and then carrying out chromatographic column purification to obtain a compound R-1 or a compound S-1. According to the time response type multiple information encryption method provided by the invention, the time response type information encryption materials with different matrixes are prepared by utilizing the compound R / S-1, and different information is encrypted by adopting the time response type information encryption materials with different matrixes, so that multiple information encryption is realized.

Description

Technical Field

[0001] The invention belongs to the technical field of organic optoelectronic functional materials, and in particular relates to a chiral inversion ultra-long room temperature phosphorescent polymer with light-activated properties and applications thereof. Background Art

[0002] Circularly polarized organic ultra-long room temperature phosphorescent materials have shown great application potential in 3D display, information storage, bio-imaging and other fields due to their unique photophysical properties. Compared with crystalline circularly polarized organic room temperature phosphorescent materials, circularly polarized organic ultra-long room temperature phosphorescent polymer materials have the advantages of easy processing, high transparency, and high stretchability. Generally speaking, a circularly polarized organic ultra-long room temperature phosphorescent material with a certain molecular structure has the same fluorescence / phosphorescence chirality signal. However, how to achieve ultra-long room temperature phosphorescent materials with opposite fluorescence / phosphorescence chirality is a huge challenge. In addition, circularly polarized organic ultra-long room temperature phosphorescent materials with photoactivation characteristics can greatly improve their security in the field of information encryption. Summary of the invention

[0003] In order to enrich and improve the performance of organic ultra-long room temperature phosphorescent materials, the present invention provides a chiral flip ultra-long room temperature phosphorescent polymer with light-activated properties and application thereof.

[0004] The present invention discloses a chiral flip ultra-long room temperature phosphorescent polymer with light-activated properties. The chiral flip ultra-long room temperature phosphorescent polymer has the following general structural formula:

[0005]

[0006] Wherein, R is any one of H, Cl, and Br, and X is any one of Cl, Br, and I.

[0007] One of the above general structural formulas is preferred, and the chiral inversion ultra-long room temperature phosphorescent polymer is compound R / S-1, and its structural formula is as follows:

[0008]

[0009] The present invention discloses a method for synthesizing compound R / S-1, which is specifically as follows:

[0010] Under nitrogen environment, binaphthyl-diphenylphosphine (R / S, R configuration or S configuration) is dissolved in N-N dimethylformamide (DMF), 1-bromopropane is added, heated and stirred at 120°C for 72 hours, then vacuum distilled and dried, and then purified by chromatographic column to obtain compound R / S-1 (compound R-1 or compound S-1). The molar amount of binaphthyl-diphenylphosphine and 1-bromopropane and the volume ratio of N-N dimethylformamide are 1 mol:10 mol:5 mL.

[0011] The present invention discloses an application of a chiral flip ultra-long room temperature phosphorescent polymer with light-activated properties, specifically a time-responsive multiple information encryption method based on the chiral flip ultra-long room temperature phosphorescent polymer, the method uses compound R / S-1 to prepare encryption materials of different matrices, and uses encryption materials of different matrices to encrypt different information, thereby realizing multiple information encryption, and the specific steps are as follows:

[0012] Step 1: Prepare R / S-1@PVA film based on compound R / S-1 doped with PVA. The specific method is as follows:

[0013] At 95°C, 100 mg of PVA (polyvinyl alcohol) was dissolved in 1 mL of deionized water to prepare a 100 mg / mL PVA aqueous solution mother solution, and (0.1-5) mg of R / S-1 was dissolved in the PVA aqueous solution mother solution to obtain PVA aqueous solutions with different R / S-1 contents; then, 0.5 mL of different PVA aqueous solutions were dripped on quartz slices and dried naturally for 12 hours. Finally, a series of transparent and highly flexible R / S-1@PVA films were prepared by drying at 65°C for 10 hours. In the PVA aqueous solution, the mass ratio of R / S-1 to PVA is (0.1-5):100.

[0014] Step 2: Prepare R / S-1@PVA film based on compound R / S-1 doped with PMMA. The specific method is as follows:

[0015] At room temperature, 100 mg of PMMA (polymethyl methacrylate) was dissolved in 1 mL of dichloromethane to prepare a 100 mg / mL PMMA mother solution, and (0.1-5) mg of R / S-1 was dissolved in the PMMA mother solution to obtain PMMA solutions with different R / S-1 contents; then, 0.5 mL of PMMA solutions with different R / S-1 contents were dripped on quartz sheets and dried naturally for 2 hours. Finally, a series of transparent R / S-1@PMMA films were prepared. The mass ratio of R / S-1 to PMMA was (0.1-5):100.

[0016] Step 3: using the prepared R / S-1@PVA film to prepare encrypted information A, and using the prepared R / S-1@PMMA film to prepare encrypted information B;

[0017] Step 4. Use a 365nm violet lamp to illuminate the encrypted information A. After one second of illumination, it will emit blue light. After turning off the light, it will emit a yellow-green afterglow for up to 6 seconds. Use a 365nm violet lamp to illuminate the encrypted information B. After illuminating for 1 second, there is no long afterglow visible to the naked eye. When the illumination time is more than 20 seconds, the film is gradually activated and brightened, producing bright orange-yellow emission. After turning off the light, it produces a long afterglow of up to 2 seconds.

[0018] Beneficial effects:

[0019] 1. The chiral flip ultra-long room temperature phosphorescent polymer with light-activated properties provided by the present invention has simple synthesis steps and low preparation cost.

[0020] 2. The film prepared by the present invention using the chiral flip ultra-long room temperature phosphorescent polymer R / S-1 with light-activated properties and PVA and PMMA can produce similar afterglow colors, different afterglow lifespans and afterglow generation conditions.

[0021] 3. The various thin film manufacturing processes and encrypted information patterns prepared by the present invention are simple to manufacture. With different afterglow lifetimes and afterglow generation conditions, a variety of encryption combinations can be flexibly adopted to achieve multiple encryption anti-counterfeiting effects. BRIEF DESCRIPTION OF THE DRAWINGS

[0022] Figure 1 are normalized phosphorescence spectra and lifetime decay curves of R / S-1@PVA films with different mass ratios of compounds in Example 2 of the present invention;

[0023] Figure 2 is the CPL spectrum of the compound R / S-1@PVA film in Example 2 of the present invention and its corresponding g value curve and DC spectrum;

[0024] Figure 3 The phosphorescence spectrum and life decay curve of the compound R / S-1@PMMA film in Example 2 of the present invention as a function of illumination time;

[0025] Figure 4 It is a schematic diagram of multiple information encryption of the compound in Example 3 of the present invention. DETAILED DESCRIPTION

[0026] The technical solution of the present invention is described in detail below through embodiments, but the protection scope of the present invention is not limited to the embodiments.

[0027] Suppliers of binaphthyl-diphenylphosphine (R / S), 1-bromopropane, polymethyl methacrylate and NN dimethylformamide (DMF): Sane Chemical Technology (Shanghai) Co., Ltd.; supplier of polyvinyl alcohol: Sigma-Aldrich; supplier of dichloromethane: Sinopharm Chemical Reagent Co., Ltd.; supplier of deionized water: Hangzhou Wahaha Group Co., Ltd.

[0028] Example 1: Preparation method of R / S-1

[0029] This embodiment discloses a method for synthesizing a chiral flip ultra-long room temperature phosphorescent polymer R / S-1 with light-activated properties. The synthesis route is as follows:

[0030]

[0031] Specific synthesis method: Under a nitrogen environment, 1 mol of binaphthyl-diphenylphosphine (R configuration or S configuration) is dissolved in 5 mL of N-N dimethylformamide (DMF), 10 mol of 1-bromopropane is added, and the mixture is heated and stirred at 120°C for 72 hours, and then distilled under reduced pressure and dried, and then purified by a chromatographic column to obtain compound R / S-1 (R / S-1 represents R-1 or S-1, R-1 represents the product obtained by the reaction of R-configuration binaphthyl-diphenylphosphine and 1-bromopropane, and S-1 represents the product obtained by the reaction of S-configuration binaphthyl-diphenylphosphine and 1-bromopropane).

[0032] Compound R-1 or S-1 (5-10 mg) was dissolved in 0.5 mL of deuterated reagent and characterized using a 400 Hz NMR spectrometer. The structure of R / S-1 was determined by H NMR as follows:

[0033] R-1 Nuclear Magnetic Resonance Proton Spectrum Determination Data: 1 H NMR (400MHz, DMSO) δ8.36–8.30(m,2H),8.16(d,J=8.2Hz,2H),7.97–7.83(m, 4H),7.74–7.60(m,8H),7.51(dd,J=12.7,7.8Hz,4H),7.34(td,J=7.8,3.5Hz ,4H),7.10–6.96(m,6H),6.73(d,J=8.6Hz,2H),3.05(dd,J=22.1,11.5Hz,2H ),2.25–2.08(m,2H),1.25(d,J=12.4Hz,4H),0.91(dd,J=18.3,11.3Hz,6H).

[0034] S-1 H NMR spectrum determination data: 1 HNMR (400MHz, DMSO) δ8.34(d,J=8.6Hz,2H),8.16(d,J=8.2Hz,2H),7.98–7.83(m,4H),7.75–7.61(m,8H),7.51(dd,J=12.3,8.0Hz,4H),7. 35(s,4H),7.03(dd,J=13.3,7.3Hz,6H),6.74(d,J=8.5Hz,2H),3.04(d,J=11.4Hz,2H),2.16(d,J=12.0Hz,2H),1.24(s,4H),0.93(s,6H).

[0035] Example 2: Photophysical properties test of thin films prepared based on compound R / S-1

[0036] (1) The films prepared with the mass ratio of R / S-1 to PVA being (0.1, 0.2, 0.5, 1, 2, 5):100 were tested.

[0037] At 95°C, 100 mg of PVA (polyvinyl alcohol) was dissolved in 1 mL of deionized water to prepare a 100 mg / mL PVA aqueous solution mother solution. 0.1, 0.2, 0.5, 1, 2, and 5 mg of R / S-1 were dissolved in the PVA aqueous solution mother solution to obtain PVA aqueous solutions with different R / S-1 contents. Then, 0.5 mL of different PVA aqueous solutions were dripped on quartz slices and dried naturally for 12 hours. Finally, a series of transparent and highly flexible R / S-1@PVA films were prepared by drying at 65°C for 10 hours. R / S-1@PVA films represent R-1@PVA films or S-1@PVA films. In the PVA aqueous solution, the mass ratio of R / S-1 to PVA is (0.1, 0.2, 0.5, 1, 2, 5): 100.

[0038] The phosphorescence spectra of the films prepared with different mass ratios were tested using a Hitachi F-4700 fluorescence spectrometer, and the obtained data were imported into the Origin software for normalization and mapping. Figure 1 a and b in the figure, where a is the normalized phosphorescence spectrum of the R-1@PVA film and b is the normalized phosphorescence spectrum of the S-1@PVA film. The prepared film was tested for luminescence lifetime using an Edinburgh FLS980 steady-state-transient fluorescence spectrometer, and the data were imported into Origin software for mapping. Figure 1 c and d in , where c is the lifetime decay curve of R-1@PVA film, and d is the lifetime decay curve of S-1@PVA film.

[0039] The afterglow colors of R / S-1@PVA films prepared with different mass ratios are all similar yellow-green, and as the mass ratio of R / S-1 to PVA gradually increases, the film luminescence lifetime gradually decreases. Figure 1 As shown in a and b, the best phosphorescence emission peaks of the R / S-1@PVA films prepared with the above 6 different mass ratios are all around 528nm, and all have similar yellow-green luminescence. Figure 1 As shown in c and d, the luminescence lifetime of the R / S-1@PVA films prepared with the above 6 different mass ratios at the optimal phosphorescence emission peak of 528nm indicates that as the mass ratio of R / S-1 to PVA gradually increases, the luminescence lifetime of the film gradually decreases, indicating that the luminescence lifetime is adjustable.

[0040] (2) Two films prepared with a mass ratio of R / S-1 to PVA of 1:100 were tested.

[0041] At 95°C, 100 mg of PVA (polyvinyl alcohol) was dissolved in 1 mL of deionized water to prepare a 100 mg / mL PVA aqueous solution mother solution, and 1 mg of R / S-1 was dissolved in the PVA aqueous solution mother solution to obtain a PVA aqueous solution containing 1 mg of R / S-1; then, 0.5 mL of different PVA aqueous solutions were dripped on a quartz sheet and dried naturally for 12 hours. Finally, the transparent and highly flexible R / S-1@PVA film was prepared by drying at 65°C for 10 hours. In the PVA aqueous solution, the mass ratio of R / S-1 to PVA is 1:100.

[0042] The two films prepared at a mass ratio of 1:100 were tested using a JASCO CPL-300 spectrometer to test their circularly polarized luminescence spectra, luminescence asymmetry factors, and the voltage values ​​corresponding to each wavelength during the test. The obtained data were imported into the Origin software for mapping. Figure 2 . Among them, a is the CPL spectrum (circularly polarized luminescence spectrum) of the compound R / S-1@PVA film. The difference in absorbance of left-handed circularly polarized light and right-handed circularly polarized light between the R-1@PVA film and the S-1@PVA film at different wavelengths shows an obvious positive and negative mirror relationship, indicating that they have obvious circularly polarized luminescence characteristics. b is the g value curve of the R / S-1@PVA film. The ordinate is the circularly polarized luminescence asymmetry factor of the two films, called the glum value or g value, and the abscissa is the wavelength, which reflects the degree to which the material produces obvious circularly polarized luminescence. c is the DC spectrum of the compound R / S-1@PVA film. It explains the luminescence intensity of the material at each wavelength when testing the circularly polarized luminescence spectrum, that is, the optimal emission position of the material is obtained.

[0043] Figure 2 It shows that the R / S-1@PVA film has obvious circularly polarized light emission characteristics, and the chiral signal undergoes positive and negative signal deflection in the fluorescence emission band and phosphorescence emission band. Figure 2 As shown in a and b, the circularly polarized luminescence properties of the two films, R / S-1@PVA film, indicate that they both have circularly polarized luminescence properties. Both the R-1@PVA film and the S-1@PVA film produce obvious positive or negative signals at their respective wavelengths of 350nm-475nm (fluorescence luminescence region of the material) and 475nm-650nm (phosphorescence luminescence region of the material), and the values ​​of the same configuration material in these two bands appear alternately positive and negative, that is, the circularly polarized luminescence conditions (positive and negative signal values) of the films with the same configuration in their own fluorescence luminescence region and phosphorescence luminescence region are opposite, while the circularly polarized luminescence conditions (positive and negative signal values) of the film with the other configuration are exactly the opposite of the mirror image, which means that both films with two configurations have the phenomenon of fluorescence and phosphorescence chiral signal reversal.

[0044] (3) Two films prepared with a mass ratio of R / S-1 to PMMA of 1:100 were tested.

[0045] At room temperature, 100 mg of PMMA was dissolved in 1 mL of dichloromethane to prepare a 100 mg / mL PMMA mother solution, and 1 mg of R / S-1 was dissolved in the PMMA mother solution to obtain a PMMA solution containing R / S-1. Then, 0.5 mL of the PMMA solution containing R / S-1 was dripped on a quartz plate and dried naturally for 2 hours. Finally, a transparent R / S-1@PMMA film was prepared. The mass ratio of R / S-1 to PMMA was 1:100.

[0046] The luminescence lifetime decay curve of the test compound R / S-1@PMMA film shows that after irradiating the film with 365nm violet light for 3 minutes, gradually bright orange-yellow emission can be observed, and its luminescence lifetime also increases with the increase of irradiation time, proving that the irradiation time can regulate their luminescence lifetime. At the same time, this activation process is reversible, which is attributed to the fact that oxygen in the air will re-enter the film, resulting in the quenching of triplet excitons. The other doping mass ratio compound films show the same phenomenon.

[0047] The film was tested for in-situ continuous phosphorescence spectrum by using Hitachi F-4700 fluorescence spectrometer, that is, without changing the excited position of the film, the instrument was used to continuously excite the film and collect its phosphorescence spectrum. The obtained data was imported into Origin software for mapping. Figure 3 a and b in the figure. a is the phosphorescence spectrum of R-1@PMMA film along with the illumination time, and b is the phosphorescence spectrum of S-1@PMMA film along with the illumination time.

[0048] The film was tested for luminescence lifetime using the Edinburgh FLS980 steady-state-transient fluorescence spectrometer. The specific operation method was as follows: a 25W ultraviolet flashlight was used to irradiate the film for 1, 5, 10, 15, and 20 seconds respectively, and the luminescence lifetime was tested. The obtained data was imported into the Origin software for mapping. Figure 3 c and d in the figure. Where c is the lifetime decay curve of R-1@PMMA film, and d is the lifetime decay curve of S-1@PMMA film.

[0049] like Figure 3 As shown in the figure, the luminescence intensity and luminescence lifetime of the R / S-1@PMMA film increase with the extension of UV light excitation time. Figure 3 Figures a and b show that as the excitation time increases, the luminescence intensity of the film gradually increases and finally reaches a maximum value and stops increasing. Using a 25W UV flashlight to continuously illuminate the film for 20 seconds is enough to observe the phenomenon consistent with the spectrum with the naked eye. Figure 3Figures c and d show that the luminescence lifetime of the film gradually increases from hundreds of microseconds to hundreds of milliseconds after being irradiated with a 25W UV flashlight for 1, 5, 10, 15, and 20 seconds, respectively.

[0050] Example 3: Application of chiral flip ultra-long room temperature phosphorescent polymer R / S-1

[0051] Different light responses of the films: R / S-1@PVA film can immediately produce a long afterglow of up to 6 seconds under ultraviolet light; R / S-1@PMMA film will not immediately produce a long afterglow visible to the naked eye under ultraviolet light, but as the ultraviolet light excitation time increases, it will produce a gradually increasing orange-yellow light emission visible to the naked eye, and after turning off the excitation of the ultraviolet light source, the film can produce a long afterglow visible to the naked eye.

[0052] Based on the different light response behaviors of the above-mentioned doped films, this embodiment develops a time-responsive multiple information encryption method based on a chiral flip ultra-long room temperature phosphorescent polymer with light-activated characteristics. Taking compound R / S-1 as an example, compound R / S-1 is doped with PVA at a mass ratio of 2% (the mass ratio of R / S-1 to PVA is 2:100) to prepare a film, and encrypted digital patterns "1" and "3" are prepared respectively. Compound S-1 is doped with PMMA at a mass ratio of 2% (the mass ratio of R / S-1 to PMMA is 2:100) to prepare a film, and an encrypted digital pattern "4" is prepared. A film is made of pure PVA aqueous solution to prepare an encrypted digital pattern "2".

[0053] 1) Compound R / S-1 was doped with PVA at a mass ratio of 2% to prepare a film, and encrypted digital patterns "1" and "3" were prepared respectively. The film and encrypted digital preparation methods were as follows:

[0054] At 95°C, 100 mg of PVA (polyvinyl alcohol) was dissolved in 1 mL of deionized water to prepare a 100 mg / mL PVA aqueous solution mother liquor, and 2 mg of R / S-1 was dissolved in the PVA aqueous solution mother liquor to obtain a PVA aqueous solution containing R / S-1; then, 0.5 mL of different PVA aqueous solutions were applied dropwise on a quartz wafer and allowed to dry naturally for 12 hours. Finally, the film was dried at 65°C for 10 hours to prepare a transparent, highly flexible R / S-1@PVA film. In the PVA aqueous solution, the mass ratio of R / S-1 to PVA is 2:100. Then, the R-1@PVA film was cut with a blade to obtain Figure 4 The encrypted number "1" shown in the figure is cut into two pieces. At the same time, the S-1@PVA film is cut with a blade to obtain Figure 4 The encrypted number "3" is shown.

[0055] 2) Compound S-1 was doped with PMMA at a mass ratio of 2% to prepare a film, and an encrypted digital pattern "4" was prepared. The film and encrypted digital preparation methods are as follows:

[0056] At room temperature, 100 mg of PMMA was dissolved in 1 mL of dichloromethane to prepare a 100 mg / mL PMMA mother solution, and 2 mg of S-1 was dissolved in the PMMA mother solution to obtain a PMMA solution containing S-1; then, 0.5 mL of the PMMA solution containing S-1 was dripped on a quartz plate and naturally dried for 2 hours. Finally, a transparent S-1@PMMA film was prepared. The mass ratio of S-1 to PMMA is 2:100. Then, the obtained film was cut with a blade to obtain Figure 4 The encrypted number "4" pattern shown.

[0057] 3) A film is made from pure PVA aqueous solution to prepare an encrypted digital pattern "2". Preparation method of the film and the encrypted digital pattern:

[0058] At 95°C, 100 mg of PVA (polyvinyl alcohol) was dissolved in 1 mL of deionized water to prepare a 100 mg / mL PVA aqueous solution mother solution. Then, 0.5 mL of PVA water droplets were applied to a quartz plate and dried naturally for 12 hours. Finally, it was dried at 65°C for 10 hours to prepare a transparent, highly flexible PVA film. Then, the PVA film was cut with a blade to obtain Figure 4 The encrypted number "2" pattern shown.

[0059] like Figure 4 The left column of diagrams shows that under natural light conditions ( Figure 4 The numbers "1234" are shown in the transparent film, indicating that the film does not produce any fluorescence or phosphorescence light response behavior under sunlight; after irradiation with a 365nm violet lamp, the number "13" appears blue, and the irradiation is immediately turned off, and the number "13" can be observed to have a yellow-green afterglow for up to 6 seconds. Figure 4 In the diagram on the right side of the middle column, when the 365nm ultraviolet light is continuously irradiated for more than 20 seconds, the number "4" is gradually activated and brightened, producing bright orange-yellow emission. After the irradiation is turned off, the number "13" still shows a yellow-green afterglow for up to 6 seconds, while the number "4" shows a yellow-green afterglow for about 2 seconds. Therefore, by using different illumination times, specific information can be read, thereby achieving information encryption.

[0060] In encryption and anti-counterfeiting applications, the information to be encrypted is hidden in a film based on PVA or PMMA. Under sunlight, it is impossible to tell with the naked eye whether it contains artificially processed information. However, after using specific ultraviolet light as the excitation light source, the artificially processed information contained in it can be found. The information encryption effect is achieved based on the phenomenon that these artificially processed information respond differently to specific ultraviolet light.

[0061] Time-responsive multiple information encryption is performed by controlling the illumination time of the film prepared based on compound R / S-1. The specific method is as follows:

[0062] 1) The film made of compound R / S-1 doped with PVA was prepared into encrypted information. After irradiation for one second, the encrypted information showed blue light emission, and after turning off the light, it showed yellow-green afterglow emission for up to 6 seconds;

[0063] 2) The film made of PMMA doped with compound R / S-1 was prepared into encrypted information. When illuminated for more than 20 seconds, the encrypted information appeared bright orange-yellow. After the light was turned off, a yellow-green afterglow glow was shown for 2 seconds.

[0064] As described above, although the present invention has been shown and described with reference to specific preferred embodiments, it should not be construed as limiting the present invention itself. Various changes in form and details may be made without departing from the spirit and scope of the present invention.

Claims

1. A chiral flip ultra-long room temperature phosphorescent polymer with light-activated properties, characterized in that: The general structural formula of the chiral flip ultralong room temperature phosphorescent polymer is as follows: Wherein, R is any one of H, Cl, and Br, and X is any one of Cl, Br, and I.

2. The chiral inversion ultra-long room temperature phosphorescent polymer according to claim 1, characterized in that: The chiral flip ultra-long room temperature phosphorescent polymer is compound R / S-1, and its structural formula is as follows:

3. The chiral inversion ultralong room temperature phosphorescent polymer according to claim 2, characterized in that: The synthesis method of compound R / S-1 is as follows: Under nitrogen environment, R-configuration or S-configuration binaphthyl-diphenylphosphine is dissolved in N-N-dimethylformamide, 1-bromopropane is added, heated and stirred at 120° C. for 72 hours, then vacuum distilled and dried, and then purified by chromatographic column to obtain compound R-1 or compound S-1.

4. A time-responsive multiple information encryption method based on the chiral flip ultra-long room temperature phosphorescent polymer of claim 2, characterized in that: Compound R / S-1 is used to prepare time-responsive information encryption materials of different matrices, and time-responsive information encryption materials of different matrices are used to encrypt different information, thereby realizing multiple information encryption.

5. The time-responsive multiple information encryption method according to claim 4, characterized in that: The specific steps are as follows: Step 1: Prepare R / S-1@PVA film based on compound R / S-1 doped with PVA; Step 2: Prepare R / S-1@PMMA film based on compound R / S-1 doped with PMMA; Step 3: using the prepared R / S-1@PVA film to prepare encrypted information A, and using the prepared R / S-1@PMMA film to prepare encrypted information B; Step 4. Use a 365nm ultraviolet lamp to illuminate the encrypted information A. After one second of illumination, it will emit blue light. After turning off the light, it will emit a yellow-green afterglow for 6 seconds. Use a 365nm ultraviolet lamp to illuminate the encrypted information B. After illuminating for 1 second, there will be no long afterglow visible to the naked eye. When the illumination time is more than 20 seconds, the film will be gradually activated and brightened, producing bright orange-yellow emission. After turning off the light, a long afterglow of 2 seconds will be produced.

6. The time-responsive multiple information encryption method according to claim 5, characterized in that: The preparation method of the R / S-1@PVA film is as follows: PVA is dissolved in deionized water to prepare a PVA aqueous solution mother solution; R / S-1 is dissolved in the PVA aqueous solution mother solution to obtain a PVA aqueous solution containing R / S-1; then, the PVA aqueous solution containing R / S-1 is absorbed and dripped on a quartz sheet, and after being naturally dried, it is dried at 65°C to obtain a transparent and flexible R / S-1@PVA film; The mass ratio of the R / S-1 to PVA is (0.1-5):

100.

7. The time-responsive multiple information encryption method according to claim 5, characterized in that: The preparation method of the R / S-1@PMMA film is as follows: PMMA is dissolved in dichloromethane to prepare a PMMA mother solution, and R / S-1 is dissolved in the PMMA mother solution to obtain a PMMA solution containing R / S-1; then, the PMMA solution containing R / S-1 is absorbed and drop-coated on a quartz plate, and after natural drying, a transparent R / S-1@PMMA film is obtained; The mass ratio of the R / S-1 to PMMA is (0.1-5):100.

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