A triphenylamine derivative, a preparation method thereof, a photochromic thin film material, a preparation method thereof, and applications thereof

Trianiline derivatives are synthesized through Suzuki reaction and doped in PMMA to prepare thin film materials with photochromicity and good reversibility, which solves the problem of insufficient reversibility of existing materials and realizes application requirements in the fields of information storage, anti-counterfeiting and optoelectronic equipment.

CN116102494BActive Publication Date: 2025-06-03GUANGDONG UNIV OF TECH
View PDF 4 Cites 0 Cited by

Patent Information

Application Number
CN202210910234.4
Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Filing Date
2022-07-29
Publication Date
2025-06-03
Estimated Expiration
2042-07-29

AI Technical Summary

Technical Problem

The existing organic small molecule luminescent materials have insufficient reversibility and are difficult to meet the application needs in the fields of information storage, anti-counterfeiting and optoelectronic equipment.

Method used

Trianiline derivatives were synthesized by Suzuki reaction and doped in polymethyl methacrylate (PMMA) to prepare a thin film material with photochromic phenomenon. The material shows different luminous colors under ultraviolet lamp irradiation and returns to its original state under oxygenated conditions, with good reversibility.

Benefits of technology

Photochromic film materials that realize room temperature phosphorescence have good reversibility and fast response characteristics, and are suitable for information encryption and decryption, anti-counterfeiting and solar protective glasses.

✦ Generated by Eureka AI based on patent content.

Smart Images

  • Figure CN116102494B_ABST
    Figure CN116102494B_ABST
Patent Text Reader

Abstract

This patent application discloses a triphenylamine derivative, its preparation method, a photochromic thin film material, its preparation method and its applications. In this patent application, the triphenylamine group is used as the donor structure, and different receptor groups R are connected. The guest material is synthesized through the Suzuki reaction, and the host material is polymethyl methacrylate (PMMA). By the method of host-guest doping, a light-stimulated response thin film material with photochromic phenomenon can be obtained, which shows different emission colors before and after being irradiated by a 365 nm ultraviolet lamp. Such a thin film material that can emit light and change color under light can be applied to displays, information encryption, anti-counterfeiting, etc. This preparation method is simple and easy to operate, providing a new design idea for the preparation of photochromic luminescent materials.
Need to check novelty before this filing date? Find Prior Art

Description

Technical Field

[0001] This patent application relates to the field of light-stimulated response materials, and specifically relates to a triphenylamine derivative, a preparation method thereof, a photochromic thin film material, a preparation method thereof, and an application thereof. Background Art

[0002] In recent years, due to the fact that stimulus-responsive luminescent materials can undergo physical or chemical changes through stimuli such as mechanical force, light, heat, and electricity, they have many potential applications in the fields of information storage, anti-counterfeiting, and optoelectronic devices. Therefore, people are becoming increasingly interested in this type of material. The photochromic phenomenon refers to a compound that, after being irradiated with light of a specific wavelength, causes a change in its structure, and thus its absorption spectrum changes significantly. Under the irradiation of light of another wavelength or the action of heat, it returns to its original state. This change in color can be observed with the naked eye, so this type of material is widely used in the fields of information storage, data encryption and decryption, display devices, anti-counterfeiting, etc.

[0003] There is a wide variety of organic small molecule luminescent materials, which mostly carry conjugated heterocycles and various chromophores. Their structures are easy to adjust. By introducing unsaturated groups such as double bonds and benzene rings and various chromophores, the conjugated length can be changed, thereby changing the optoelectronic properties of the compound. For example, porphyrin compounds, carbazole, pyrazine, thiazole derivatives, perylene derivatives, etc. However, the reversibility of existing organic small molecule luminescent materials still needs to be further improved.

[0004] Content of the Patent Application

[0005] To overcome the problems existing in the above-mentioned prior art, the primary objective of this patent application is to provide a triphenylamine derivative, which is a photochromic thin film material with room temperature phosphorescence, and this luminescent material has good reversibility. The triphenylamine derivative in this patent application uses the triphenylamine group as the donor group and the receptor group as R, and synthesizes a class of guest compounds through the Suzuki reaction. The guest compounds are doped in the host polymethyl methacrylate (PMMA) to obtain a thin film material with photochromic properties. After being irradiated with a 365 nm ultraviolet lamp, this type of thin film material shows different luminescent colors, and after standing for a period of time under oxygen-filled conditions, it returns to its original state, having good reversibility.

[0006] Another objective of this patent application is to provide a preparation method for the above-mentioned triphenylamine derivative.

[0007] Another objective of this patent application is to provide a photochromic thin film material.

[0008] Another objective of this patent application is to provide a preparation method for the above-mentioned photochromic thin film material.

[0009] Another object of the present patent application is to provide the application of the above photochromic thin film material in anti-counterfeiting, information encryption and decryption, and solar protection glasses.

[0010] The above object of the present patent application is achieved by the following technical solutions:

[0011] A triphenylamine derivative has a structural formula shown in formula (I):

[0012]

[0013] Wherein, R is an electron acceptor group and is selected from any one of the following groups:

[0014]

[0015]

[0016] Preferably, the molecular structure of the triphenylamine derivative in the present patent application is one of the following structural formulas:

[0017]

[0018]

[0019]

[0020] The present patent application also provides a preparation method of the above triphenylamine derivative, including the following steps:

[0021] Under nitrogen protection, dissolve 4-borotriphenylamine, R-Br, tetrakis(triphenylphosphine)palladium, and potassium carbonate in a tetrahydrofuran solvent, add water, and react at 70 °C for 8 h to obtain a product with the structure shown in formula (I).

[0022] The present patent application also provides a photochromic thin film material, which includes a host material and a guest material doped with each other. Among them, the host material is polymethyl methacrylate (PMMA), and the guest material is the above triphenylamine derivative.

[0023] Preferably, the doping mass fraction of the guest material in the host material is 2%.

[0024] The present patent application also provides a preparation method of the above photochromic thin film material, including the following steps:

[0025] S1. Weigh the host material PMMA and put it into a clean and dry container, add the host solvent until it is completely dissolved to prepare a host solution;

[0026] S2. Weigh the guest materials separately and put them into a clean and dry container to prepare a guest sample;

[0027] S3. Take the host PMMA solution in step S1 and the guest sample in step 2 in a proportion where the doping mass fraction of the guest material in the host material is 2%. Dissolve the guest sample in the host solution until it is completely dissolved, and then evenly coat it on a glass slide. After the solvent has completely evaporated, a photochromic thin film material is obtained.

[0028] Preferably, the host solvent in step S1 is tetrahydrofuran.

[0029] Preferably, in step S3, when dissolving the guest sample in the host solution, use ultrasonic waves to completely dissolve the sample.

[0030] Application of the photochromic thin film material in this patent application in the field of information encryption and decryption.

[0031] This patent application also provides the application of the above-mentioned photochromic thin film material in solar protection glasses and the field of anti-counterfeiting.

[0032] Compared with the prior art, the beneficial effects of this patent application are:

[0033] This patent application uses the triphenylamine group as the donor group, connects different electron acceptor groups R, and synthesizes triphenylamine derivatives through the Suzuki reaction. The triphenylamine derivatives have unique luminescent properties, and this property causes the phenomenon of photochromism. The synthesis steps of the triphenylamine derivatives are simple and the yield is relatively high. The host material PMMA is an easily available and inexpensive industrial polymer, with advantages such as high mechanical strength, strong tensile resistance, and strong impact resistance.

[0034] The photochromic thin film material prepared in this patent application shows different luminescent colors and strong phosphorescence emission before and after being irradiated by an ultraviolet lamp. Moreover, after being placed in an oxygen-filled environment for a period of time, it can return to its original state, with good reversibility, which is a fast response process. Therefore, using this feature, it can be applied in the fields of information encryption and decryption, anti-counterfeiting, and solar protection glasses.

[0035] The triphenylamine derivative photochromic thin film material prepared in this patent application, based on the thin film of small molecule doped polymer, is rare for this kind of light-stimulated response thin film material due to the characteristics of photoluminescence color change behavior. Description of the Drawings

[0036] Figure 1 1H NMR spectrum of triphenylamine derivative A1 prepared in Example 1 1 1H NMR spectrum;

[0037] Figure 2 Mass spectrum of triphenylamine derivative A1 prepared in Example 1;

[0038] Figure 3 1H NMR spectrum of triphenylamine derivative A4 prepared in Example 2 1 ;

[0039] Figure 4 Mass spectrum of triphenylamine derivative A4 prepared in Example 2;

[0040] Figure 5 Emission spectrum of the photochromic thin film material M prepared in Example 4 over a period of time;

[0041] Figure 6 Emission spectrum of the photochromic thin film material M prepared in Example 4 after being placed in pure oxygen for a longer period of time;

[0042] Figure 7 Emission spectrum of the photochromic thin film material N prepared in Example 5 over a period of time;

[0043] Figure 8 Emission spectrum of the photochromic thin film material N prepared in Example 5 after being placed in pure oxygen for a longer period of time. Detailed implementation manners

[0044] The implementation schemes of this patent application will be described in detail below in combination with examples. However, those skilled in the art will understand that the following examples are only used to illustrate this patent application and should not be regarded as limiting the scope of this patent application. For those not specified in the examples, the operations are carried out under conventional conditions or conditions recommended by the manufacturer. Reagents or instruments not specified by the manufacturer can be obtained as conventional products available on the market.

[0045] It should be noted that:

[0046] In this patent application, unless otherwise specified, all the implementation manners and preferred implementation methods mentioned in this article can be combined with each other to form a new technical solution.

[0047] In this patent application, unless otherwise specified, percentages (%) or parts refer to weight percentages or weight parts relative to the composition.

[0048] In this patent application, unless otherwise specified, the various components involved or their preferred components can be combined with each other to form a new technical solution.

[0049] In this patent application, unless otherwise stated, the numerical range "a to b" represents an abbreviated representation of any real number combination between a and b, where both a and b are real numbers.

[0050] The "range" disclosed in this patent application can be in the form of one or more lower limits and one or more upper limits, respectively.

[0051] In this patent application, unless otherwise specified, each reaction or operation step can be carried out sequentially or in order. Preferably, the reaction methods herein are carried out sequentially.

[0052] Unless otherwise specified, the technical and scientific terms used herein have the same meaning as those familiar to those skilled in the art. In addition, any methods or materials similar or equivalent to the described content can also be applied to this patent application.

[0053] This patent application provides a triphenylamine derivative having a structural formula shown in formula (I):

[0054]

[0055] Wherein, R is an electron acceptor group, and R is selected from any one of the following groups:

[0056]

[0057]

[0058] In some preferred embodiments, the molecular structure of the triphenylamine derivative of this patent application is one of the following structural formulas:

[0059]

[0060]

[0061] This patent application also provides a preparation method of the above triphenylamine derivative, including the following steps:

[0062] Under nitrogen protection, 4-borotriphenylamine, R-Br, tetrakis(triphenylphosphine)palladium, and potassium carbonate are dissolved in a tetrahydrofuran solvent, water is added, and the reaction is carried out at 70 °C for 8 h to obtain a product having the structure shown in formula (I).

[0063] This patent application also provides a photochromic thin film material, which includes a host material and a guest material doped with each other. Among them, the host material is polymethyl methacrylate PMMA, and the guest material is the above triphenylamine derivative.

[0064] Preferably, the doping mass fraction of the guest material in the host material is 2%.

[0065] This patent application also provides a preparation method of the above photochromic thin film material, including the following steps:

[0066] S1. Weigh the host material PMMA and put it into a clean and dry container, add the host solvent until it is completely dissolved to prepare a host solution;

[0067] S2. Weigh the guest materials separately and put them into clean and dry containers to prepare the guest samples.

[0068] S3. According to the proportion that the doping mass fraction of the guest material in the host material is 2%, measure the host PMMA solution in step S1 and the guest sample in step 2. Dissolve the guest sample in the host solution until it is completely dissolved, and then evenly coat it on the glass slide. After the solvent has completely volatilized, a photochromic thin film material is obtained.

[0069] Preferably, the host solvent in step S1 is tetrahydrofuran.

[0070] Preferably, in step S3, when dissolving the guest sample in the host solution, use ultrasonic waves to completely dissolve the sample.

[0071] The application of the photochromic thin film material in this patent application in the field of information encryption and decryption.

[0072] This patent application also provides the application of the above photochromic thin film material in solar protection glasses and the field of anti-counterfeiting.

[0073] Under the irradiation of ultraviolet light in this patent application, PMMA encapsulates small molecules (i.e., triphenylamine derivatives), inhibits molecular movement, inhibits the non-radiative pathway of triplet excitons, avoids the contact of small molecules with oxygen, and enhances phosphorescence emission. In addition, triphenylamine derivatives are considered to be highly efficient electroactive and photoactive materials and are widely used in optoelectronic applications.

[0074] The photo-stimulated response behavior in this patent application is due to the host-guest doping of the host material (PMMA) and the compound of formula (I) as the guest material, and then a doped thin film is formed by spin coating. After being irradiated with a 365 nm ultraviolet lamp, the doped thin film M formed by doping triphenylamine derivative A1 and PMMA can show blue-violet luminescence. Then, under continuous ultraviolet lamp irradiation, it changes from blue-violet to orange-yellow luminescence; while for the thin film material N obtained by host-guest doping of compound A4 and PMMA, after being irradiated with ultraviolet light, it shows a photochromic luminescence process of changing from the original blue-violet to yellow-green. Therefore, triphenylamine derivatives A1 and A4 as guest materials have good reversibility when used as photochromic thin film materials.

[0075] In the preparation method of the triphenylamine derivative described in this patent application, the product with the structure shown in formula (I) obtained by synthesis in the steps is the crude product of the target compound, and existing conventional purification methods can be used to purify it to improve the purity of the compound shown in formula (I). Specifically, recrystallization or silica gel column chromatography can be used for purification. When recrystallization is used for purification, a combination of a good solvent and a poor solvent is selected as the solvent for recrystallization, preferably a combination of dichloromethane and n-hexane. When column chromatography is used for purification, specifically, the target compound obtained in the steps is subjected to silica gel column chromatography, and is eluted with an eluent composed of petroleum ether and dichloromethane with a volume ratio of (1-10):1 (preferably eluted with an eluent composed of petroleum ether and dichloromethane with a volume ratio of 8:1), and the solvent is evaporated to obtain the purified target compound.

[0076] Hereinafter, taking compound A1 as a representative example, the preparation method of the triphenylamine derivative compound of formula (I) will be described in detail.

[0077] Example 1

[0078] This example provides a triphenylamine derivative with a structural formula as shown in A1:

[0079]

[0080] The reaction equation and preparation method of this compound are as follows:

[0081]

[0082] Weigh 4-borotriphenylamine (1.2 g, 4.15 mmol), 5-bromoquinoline (0.86 g, 4.13 mmol), tetrakis(triphenylphosphine)palladium (0.084 g, 0.07 mmol), and potassium carbonate (2.07 g, 15 mmol) into a 250 ml two-necked flask. After evacuating and filling with nitrogen, add 60 ml of tetrahydrofuran solvent and 8 ml of water. Under nitrogen protection and at a reaction temperature of 70 °C, stir and react for 8 h. After the reaction is completed, wait for it to cool to room temperature, extract with dichloromethane, and then separate by silica gel column chromatography (the eluent is petroleum ether:dichloromethane = 8:1). Finally, 0.6 g of the product is obtained with a yield of 75%.

[0083] Example 2

[0084] This example provides a triphenylamine derivative with a structural formula as shown in A4:

[0085]

[0086] The preparation method of this compound is as follows:

[0087]

[0088] Weigh 4-triphenylamine boronic acid (434 mg, 1.5 mmol), 6-bromoquinoline (353 mg, 1.7 mmol), tetrakis(triphenylphosphine)palladium(0) (70 mg, 0.07 mmol), and potassium carbonate (1.38 mg, 10 mmol) into a 250 ml two-necked flask. After evacuating and filling with nitrogen, add 50 ml of tetrahydrofuran solvent and 5 ml of water. Under nitrogen protection, react at a temperature of 70 °C with stirring for 8 h. After the reaction is completed, wait for it to cool to room temperature, extract with dichloromethane, and then separate by silica gel column chromatography (the eluent is petroleum ether:dichloromethane = 8:1). Finally, 0.23 g of the product is obtained, with a yield of 76.66%.

[0089] Example 3

[0090] Preparation of the solution of the host molecule polymethyl methacrylate (PMMA):

[0091] S1. Weigh 10 g of PMMA and place it in a dry and clean 250 mL round-bottom flask. Add 100 mL of tetrahydrofuran solvent, block the mouth of the flask with a condenser, and stir at room temperature. After the sample is completely dissolved, a colorless and transparent solution with a concentration of 100 mg / mL is obtained.

[0092] Example 4

[0093] The preparation method of the photochromic thin film material M with triphenylamine derivative A1 as the guest material is as follows:

[0094] S2. Weigh a total of 2 mg of the guest molecule A1 into a centrifuge tube.

[0095] S3. Measure 1 ml of the host solution in Example 3, with a mass fraction of 2%. Put this solution into the centrifuge tube in step S2. After ultrasonic mixing evenly, uniformly drop this mixture onto a quartz wafer. After the solvent has completely evaporated, the photochromic thin film material M is obtained.

[0096] Example 5

[0097] The preparation method of the photochromic thin film material N with triphenylamine derivative A4 as the guest material is as follows:

[0098] S2. Weigh a total of 2 mg of the guest molecule A4 into a centrifuge tube.

[0099] S3. Measure 1 ml of the host solution in Example 3, with a mass fraction of 2%. Put this solution into the centrifuge tube in step S2. After ultrasonic mixing evenly, uniformly drop this mixture onto a quartz wafer. After the solvent has completely evaporated, the photochromic thin film material N is obtained.

[0100] Characterization and performance testing

[0101] The compounds or materials prepared in Examples 1, 2, 4, and 5 were characterized and / or subjected to performance tests, and the results are as Figures 1 to 6 shown.

[0102] Using a Bruker 400 MHz superconducting nuclear magnetic resonance spectrometer with deuterated chloroform as the solvent, the structural formula of the product obtained in Example 1 was determined. The hydrogen spectrum obtained is as Figure 1 shown, and the characteristic wave numbers (ppm) are 1 HNMR(400 MHz, Chloroform-d) δ8.94(dd, J = 4.3, 1.7 Hz, 1H), 8.43(d, J = 8.3 Hz, 1H), 8.18(d, J = 8.5 Hz, 1H), 7.78(dd, J = 8.5, 7.1 Hz, 1H), 7.55(dd, J = 7.2, 1.2 Hz, 1H), 7.43(dd, J = 8.6, 4.3 Hz, 1H), 7.35–7.27(m, 6H), 7.22–7.16(m, 6H), 7.10–7.04(m, 2H). It can be seen that the peaks in the molecular hydrogen spectrum can correspond one by one to the target product, and the quantity is reasonable. This indicates that the compound shown in triphenylamine derivative A1 was prepared in Example 1, and this compound has a single structure and high purity;

[0103] Mass spectrometry detection: The compound obtained in Example 1 was dissolved in dichloromethane to prepare a solution with a concentration of 1 mg / mL, and a high-resolution quadrupole combined with an electrostatic field orbitrap liquid chromatography-mass spectrometry instrument was used for mass spectrometry testing. The test results are as Figure 2 shown. It can be obtained from the figure that the relative molecular mass of triphenylamine derivative A1 is 373.17. If one H is subtracted, it is the same as the relative molecular mass of the synthesized compound A1, further proving that the compound prepared in Example 1 is the compound shown in triphenylamine derivative A1, and this compound has a single structure and high purity.

[0104] Using a Bruker 400 MHz superconducting nuclear magnetic resonance spectrometer with deuterated chloroform as the solvent, the structural formula of the product obtained in Example 2 was determined. The characteristic wave numbers (ppm) of the nuclear magnetic resonance hydrogen spectrum obtained are (see Figure 3 ) 1 HNMR(400 MHz, Chloroform-d) δ9.25(s, 1H), 8.51(s, 1H), 7.99(d, J = 15.9 Hz, 2H), 7.87(s, 1H), 7.64(d, J = 39.1 Hz, 3H), 7.29(s, 4H), 7.17(s, 6H), 7.07(s, 2H). It can be seen that the peaks in the molecular hydrogen spectrum can correspond one by one to the target product, and the quantity is reasonable. This indicates that the compound shown in triphenylamine derivative A4 was prepared in Example 2, and this compound has a single structure and high purity.

[0105] Mass spectrometry detection: The compound obtained in Example 2 was dissolved in dichloromethane to prepare a solution with a concentration of 1 mg / mL. An ultra-high resolution quadrupole combined with an electrostatic field orbitrap liquid chromatography-mass spectrometry instrument was used for mass spectrometry testing. The test results are as follows Figure 4 shown. It can be concluded from the figure that the relative molecular mass of triphenylamine derivative A4 is 373.17. If one H is subtracted, it is the same as the relative molecular mass of the synthesized compound A4, further proving that the compound prepared in Example 2 is the compound shown by triphenylamine derivative A4, and the structure of this compound is single and the purity is high.

[0106] Figure 5 The figure shows the emission spectra of the photochromic thin film material M prepared in Example 4 over a period of time. From Figure 5 the figure, it can be seen that after irradiation with a 365 nm ultraviolet lamp, the photochromic thin film material M formed by doping triphenylamine derivative A1 and PMMA can show blue-violet luminescence. Then, as the irradiation time of the ultraviolet lamp increases from 2 s to 4 s, 6 s, 8 s, 10 s, 12 s, and finally to 14 s, the emission light of the photochromic thin film material M changes from blue-violet to orange-yellow luminescence. Referring to Figure 6 shown, after being placed for a longer period of time (i.e., restored for a certain time) under pure oxygen conditions, for example, when the restoration time increases from 3 min to 6 min, 9 min, 12 min, and finally to 15 min, the emission light of the photochromic thin film material M changes from orange-yellow luminescence to blue-violet luminescence, that is, it returns to the original luminescence color and state. Therefore, the photochromic thin film material M prepared in Example 4 has good reversibility.

[0107] Figure 7 The figure shows the emission spectra of the photochromic thin film material N prepared in Example 5 over a period of time. From Figure 7 the figure, it can be seen that after irradiation with a 365 nm ultraviolet lamp, the photochromic thin film material N formed by doping triphenylamine derivative A4 and PMMA can show blue-violet luminescence. Then, as the irradiation time of the ultraviolet lamp increases from 2 s to 4 s, 6 s, 8 s, 10 s, 12 s, and finally to 14 s, we can see the photochromic luminescence process in which the emission light of the photochromic thin film material M changes from the original blue-violet to yellow-green. Referring to Figure 8 shown, after being placed for a longer period of time (i.e., restored for a certain time) under pure oxygen conditions, for example, when the restoration time increases from 3 min to 6 min, 9 min, 12 min, and finally to 15 min, the emission light of the photochromic thin film material M changes from orange-yellow luminescence to blue-violet luminescence, that is, it returns to the original luminescence color and state. Therefore, the photochromic thin film material N prepared in Example 5 has good reversibility.

[0108] This patent application uses a triphenylamine group as a donor group, connects different electron acceptor groups R, and synthesizes triphenylamine derivatives through the Suzuki reaction. The triphenylamine derivatives have unique luminescent properties, which cause the phenomenon of photochromism. The synthesis steps of the triphenylamine derivatives are simple and the yield is relatively high. The host material PMMA is an easily available and inexpensive industrial polymer, with advantages such as high mechanical strength, strong tensile and impact resistance.

[0109] The photo-stimulus responsive thin film material prepared in this patent application shows different luminescent colors and strong phosphorescence emission before and after being irradiated by an ultraviolet lamp. Moreover, after being placed for a period of time in an oxygen-filled environment, it can return to its original state. Therefore, it has good stability. At the same time, the above changes are also a process of rapid response. Therefore, using this feature, it can be applied in fields such as information encryption and decryption, anti-counterfeiting, and solar protection glasses.

[0110] The triphenylamine derivative photochromic thin film material of this patent application, based on a thin film of a small molecule doped polymer, is rare for this kind of photo-stimulus responsive thin film material due to the characteristics of the photoluminescence color change behavior.

[0111] In the description of this specification, the description with reference to terms such as "one embodiment", "some embodiments", "schematic embodiments", "examples", "specific examples", or "some examples" means that the specific features, structures, materials, or characteristics described in connection with the embodiments or examples are included in at least one embodiment or example of this patent application. In this specification, the schematic expressions of the above terms do not necessarily refer to the same embodiment or example. Moreover, the specific features, structures, materials, or characteristics described can be combined in a suitable manner in any one or more embodiments or examples.

[0112] Although several embodiments of this patent application have been shown and described, those of ordinary skill in the art can understand that various changes, modifications, substitutions, and variations can be made to these embodiments without departing from the principles and purposes of this patent application. The scope of this patent application is defined by the claims and their equivalents.

Claims

1. A triphenylamine derivative, characterized in that, the molecular structure of the triphenylamine derivative is as shown in A1 below:

2. The preparation method of the triphenylamine derivative according to Claim 1, characterized in that, it comprises the following steps: Under nitrogen protection, dissolve 4-borotriphenylamine, 5-bromoquinoline, tetrakis(triphenylphosphine)palladium, and potassium carbonate in a tetrahydrofuran solvent, add water, and react at 70 °C for 8 h to obtain a product having the structure shown in triphenylamine derivative A1.

3. A photochromic thin film material, characterized in that, it comprises a host material and a guest material doped with each other, wherein the host material is polymethyl methacrylate PMMA, and the guest material is the triphenylamine derivative according to Claim 1.

4. The photochromic thin film material according to Claim 3, characterized in that, the doping mass fraction of the guest material in the host material is 2%.

5. The preparation method of the photochromic thin film material according to Claim 4, characterized in that, it comprises the following steps: S1. Weigh the host material PMMA and put it into a clean and dry container, add a host solvent until it is completely dissolved to prepare a host solution; S2. Weigh the guest material separately and put it into a clean and dry container to prepare a guest sample; S3. Measure the host solution in step S1 and the guest sample in step S2 in a ratio such that the doping mass fraction of the guest material in the host material is 2%, dissolve the guest sample in the host solution to completely dissolve the sample, and then evenly coat it on a glass slide. After the solvent has completely evaporated, the photochromic thin film material is obtained.

6. The preparation method of the photochromic thin film material according to Claim 5, characterized in that, the host solvent in step S1 is tetrahydrofuran.

7. The preparation method of the photochromic thin film material according to Claim 5, characterized in that, in step S3, when dissolving the guest sample in the host solution, ultrasonic waves are used to completely dissolve the sample.

8. The application of the photochromic thin film material according to Claim 3 in the field of information encryption and decryption.

9. The application of the photochromic thin film material according to Claim 3 in solar protection glasses and the field of anti-counterfeiting.

Citation Information

Patent Citations

  • Method for preparing 4-(diphenylamino)biaryl compound in water phase

    CN101948366A

  • Film material for realizing photostimulation response through pi-conjugation regulation and control as well as preparation method and application

    CN113637467A

  • Compound Containing Quinoline Derivatives And Organic Electronic Element Using The Same, Terminal Thereof

    KR101251455B1

  • Photochromic method involving an aromatic amine

    US4205988A