Azobenzene polymer material and application thereof in nanoimprint lithography
By using azobenzene polymer material to prepare nanoimprinted photoresist, the problem of performance changes in nanoimprinted photoresist under high temperature or light irradiation conditions in the prior art is solved, and a high-precision and stability nanoimprinting effect is achieved.
Patent Information
- Application Number
- CN202510127163.4
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2025-01-31
- Publication Date
- 2025-05-06
- Estimated Expiration
- 2045-01-31
AI Technical Summary
Existing nanoimprinted photoresist is prone to polymerization, degradation or performance changes under high temperature or light irradiation, resulting in pattern distortion or unstable quality during imprinting.
Azobenzene polymer material is used as nanoimprinted photoresist and prepared by ring-opening metathesis polymerization, which has excellent thermal stability and photostability.
A nanoimprinted photoresist that maintains excellent performance under high temperature and light irradiation conditions is achieved, ensuring high accuracy and quality stability of the pattern.
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Figure CN119930995A_ABST
Abstract
Description
Technical Field
[0001] The invention belongs to the technical field of photoresponsive polymer materials and nanoimprint lithography, and in particular relates to an azobenzene polymer material and application thereof in nanoimprint lithography. Background Art
[0002] With the rapid development of nanotechnology, nanoimprint lithography (NIL) technology has gradually become one of the important technologies in the field of micro-nano processing due to its high resolution, low cost and high efficiency, and is widely used in semiconductor manufacturing, optoelectronics, sensors, nanomaterials and other fields. Nanoimprint lithography transfers fine patterns from molds to nanoimprint photoresists by mechanical imprinting. Therefore, the performance of nanoimprint photoresists directly affects the transfer quality, accuracy and reliability of the final product. In the NIL process, nanoimprint photoresists not only need to have good pattern replication capabilities, but also must maintain excellent performance stability under complex environments such as high temperature and sunlight.
[0003] However, although existing nanoimprint photoresists (such as thermosetting resins and photocurable resins) can meet basic pattern transfer requirements under certain conditions, their stability is obviously insufficient, which has become a bottleneck restricting the development of technology. First, traditional nanoimprint photoresists are prone to thermal degradation or cross-linking in high temperature environments, which affects the performance of nanoimprint photoresists and thus affects the quality and accuracy of patterns during nanoimprinting. In addition, nanoimprint photoresists are highly sensitive to light. When exposed to ultraviolet light or sunlight for a long time, they are prone to photodegradation and performance degradation, resulting in blurred or distorted details of patterns during nanoimprinting. Furthermore, many existing photoresists are easily affected by environmental factors (such as humidity, oxygen in the air, etc.) during storage and transportation, resulting in polymerization or decomposition reactions, causing changes in the chemical properties of the photoresists and affecting the quality and consistency of the finished products. These stability issues not only limit the application of existing photoresists in high-precision and high-reliability manufacturing, but also greatly increase the complexity and cost of production.
[0004] Therefore, developing a nanoimprint photoresist with excellent stability and high precision has become the key to improving the quality of NIL process, reducing production costs and promoting the development of high-end manufacturing technology. Summary of the invention
[0005] The present invention provides an azobenzene polymer material and its application in nanoimprint lithography, so as to solve the problem that the existing nanoimprint photoresist may undergo polymerization, degradation or performance change under high temperature or light irradiation conditions, resulting in pattern distortion or unstable quality during imprinting, and achieve compatibility with a variety of micro-nano processing technologies, and economically and efficiently realize high-precision patterns with key dimensions less than 25 nanometers.
[0006] The method for preparing the azobenzene polymer material of the present invention comprises the following steps:
[0007] Step 1: The aromatic amine compound represented by formula Ⅰ-a is subjected to coupling reaction to obtain the compound represented by formula Ⅰ-b;
[0008] Step 2: The compound represented by formula Ⅰ-b reacts with the halohydrin represented by formula Ⅰ-c to obtain the compound represented by formula Ⅰ-d;
[0009] Step 3: The compound represented by formula Ⅰ-e reacts with Ⅰ-f to obtain the compound represented by formula Ⅰ-g;
[0010] Step 4: The compound represented by formula Ⅰ-g is subjected to esterification reaction with Ⅰ-d to obtain the compound represented by formula Ⅰ-h;
[0011] Step 5: The compound represented by Formula Ⅰ-h is subjected to a ring-opening metathesis polymerization reaction to obtain a photoinduced solid-liquid transition azobenzene polymer, the general structural formula of which is shown in Formula Ⅰ below.
[0012]
[0013] Where n represents the degree of polymerization, and the value range is 5 to 500. The molecular weight is preferably about 20,000.
[0014] Specifically, the reaction process of each step includes the following:
[0015] Step 1: In an ice-water bath, compound Ⅰ-a is dissolved in concentrated hydrochloric acid, tetrahydrofuran and ice water, and then sodium nitrite solution is slowly added dropwise, and stirred at -5 to 0°C for 30 min to generate diazonium salt. In another beaker, phenol is dissolved in sodium hydroxide, sodium bicarbonate and ice water, and diazonium salt is slowly added dropwise. The reaction mixture is stirred for 2 h and slowly warmed to room temperature, neutralized with hydrochloric acid to pH = 6, filtered and washed with water. After the crude product is dried, it is dissolved in a small amount of toluene, and a large amount of n-hexane is slowly added for recrystallization to obtain the compound shown in formula Ⅰ-b.
[0016] Step 2: Add potassium carbonate, compound I-b, potassium iodide, compound I-c and magnetron into a flask, dissolve in N,N-dimethylformamide solvent, and vigorously stir the reaction at 110°C for 12 h. The obtained mixture is cooled to room temperature, extracted with dichloromethane, and the organic phase is collected. The solvent is removed by rotary evaporator to obtain a crude product. The crude product is dissolved in dichloromethane, and a large amount of toluene is slowly added for recrystallization and purification to obtain the compound shown in formula I-d.
[0017] Step 3: Add compound Ⅰ-e, compound Ⅰ-f, triethylamine and toluene into a round-bottom flask equipped with a magnet and a reflux condenser. Stir the mixture at 110°C for 19 h, cool to room temperature, and remove the solvent using a rotary evaporator. Dissolve the remaining solid in dichloromethane, wash with distilled water 3 times, then wash with saturated sodium chloride solution 3 times, and dry with anhydrous sodium sulfate. After filtration, use a rotary evaporator to remove the solvent to obtain the compound shown in formula Ⅰ-g.
[0018] Step 4: Add compound Ⅰ-d, compound Ⅰ-g, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, N,N-diisopropylethylamine, 4-dimethylaminopyridine, dichloromethane and a magnet into a round-bottom flask and stir at room temperature for 24 hours. The reaction solution was washed 3 times with distilled water, 3 times with saturated sodium chloride solution, and dried over anhydrous sodium sulfate. After filtration, the solvent was removed by rotary evaporation to obtain a yellow solid crude product. The solid was dissolved in tetrahydrofuran, and a large amount of methanol was slowly added for recrystallization. After filtration, the compound shown in formula Ⅰ-h was obtained.
[0019] Step 5: Add compound Ⅰ-h to the reaction tube, replace nitrogen in the glove box transition chamber three times, and then put it into the glove box, add Grubbs third catalyst, anhydrous dichloromethane and magnet, stir at room temperature for 5 minutes, add vinyl ethyl ether to the reaction solution to terminate the reaction, continue stirring for 15 minutes, then take it out of the glove box, dilute the reaction solution with tetrahydrofuran, pass through an alkaline alumina chromatography column, and remove the residual Grubbs third catalyst. After removing the solvent using a rotary evaporator, dissolve the polymer in a small amount of tetrahydrofuran and slowly add it dropwise to rapidly stirred methanol to precipitate the polymer. Pour off the supernatant after centrifugation. Repeat the above dissolution-precipitation steps twice, and obtain the polymer shown in formula Ⅰ after drying.
[0020] Application of the azobenzene polymer material of the invention in nanoimprint lithography.
[0021] Specifically, the azobenzene polymer material is used as an imprint photoresist to perform nanoimprinting, including the following steps:
[0022] The azobenzene polymer material is dissolved in cyclopentanone to form a solution, and the solution is spin-coated on a square glass sheet. The solvent is evaporated to obtain a nanoimprint film; the nanoimprint film is irradiated with ultraviolet LED light to liquefy the polymer film, and a certain pressure is applied to the nanoimprint mold with a microstructure so that the liquefied polymer fills the microstructure of the imprint mold. The nanoimprint mold and the sample that are fully in contact are placed in a vacuum oven for a period of time, and the residual air in the imprint structure is removed at room temperature. The polymer film is then cured using visible light LED light, and the corresponding nanostructure can be obtained after the imprint mold is removed.
[0023] The azobenzene polymer material is dissolved in cyclopentanone to form a solution, and the concentration of the polymer in the cyclopentanone is 20 mg / mL.
[0024] The wavelength of the ultraviolet LED is 365 nm, and the wavelength of the visible light LED is 530 nm.
[0025] The nano-pattern obtained by the nano-imprinting has a multi-scale structure. The obtained nano-structure is subjected to surface gold spraying treatment, and its nano-pattern is observed using a scanning electron microscope.
[0026] The present invention also provides a method for using the azobenzene polymer for nanoimprinting, and studies the stability and imprinting accuracy of the azobenzene polymer as nanoimprinting photoresist.
[0027] The azobenzene polymer nanoimprint photoresist of the present invention has excellent stability and high precision. The azobenzene polymer is subjected to different heat and sunlight irradiation treatments (no treatment, 50°C treatment for 1 h, 100°C treatment for 1 h, 150°C treatment for 1 h and sunlight irradiation for 48 h), and its performance as a nanoimprint photoresist is tested by nanoimprinting. After the azobenzene polymer is subjected to different treatments, its performance as a nanoimprint photoresist remains unchanged.
[0028] In summary, the azobenzene polymer provided by the present invention can be used as a nanoimprint photoresist to simply and quickly develop a nanoimprint photoresist with excellent stability. At the same time, the nanoimprint photoresist has a high imprint accuracy.
[0029] Compared with the existing nanoimprint photoresist, the advantages of the present invention are specifically embodied in:
[0030] 1. The present invention uses ring-opening metathesis polymerization to prepare azobenzene polymer as nanoimprint photoresist, and the preparation method is simple; the selected azobenzene polymer has a simple structure, and the raw materials are easily available, which is suitable for large-scale production.
[0031] 2. The azobenzene polymer of the present invention has excellent thermal stability and light stability when used as nanoimprint photoresist, and can meet the needs of daily transportation, storage and use of daily nanoimprint photoresist.
[0032] 3. The azobenzene polymer in the present invention has high imprinting accuracy when used as nanoimprint photoresist, making it crucial in many high-tech fields, especially semiconductors, optoelectronics, medical equipment, display technology, optical devices and quantum computing. BRIEF DESCRIPTION OF THE DRAWINGS
[0033] The accompanying drawings are part of this application and are used to provide a further understanding of the present invention. The illustrative embodiments of the present invention and their descriptions are used to explain the present invention, but do not constitute an improper limitation of the present invention. Obviously, the drawings described below are only some embodiments. For ordinary technicians in this field, other drawings can be obtained based on these drawings without creative work. In the drawings:
[0034] Figure 1 UV-visible absorption spectrum of the prepared azobenzene polymer film.
[0035] Figure 2 This is a comparison chart of gel permeation chromatography of the prepared azobenzene polymer and the azobenzene polymer after different treatments.
[0036] Figure 3 This is a comparison chart of the hydrogen nuclear magnetic resonance spectra of the prepared azobenzene polymer and the azobenzene polymer after different treatments.
[0037] Figure 4 This is a comparison chart of the total reflection infrared spectra of the prepared azobenzene polymer and the azobenzene polymer after different treatments.
[0038] Figure 5 Scanning electron micrograph of the prepared azobenzene polymer with high precision patterning prepared by nanoimprinting.
[0039] Figure 6 Scanning electron micrograph of the prepared azobenzene polymer without nanoimprinting.
[0040] Figure 7 This is a scanning electron microscopy image of nanoimprinting of the prepared azobenzene polymer after treatment at 50°C for 1h.
[0041] Figure 8 This is a scanning electron microscopy image of the nanoimprint of the prepared azobenzene polymer after treatment at 100°C for 1h.
[0042] Fig. 9 This is a scanning electron microscopy image of the nanoimprint of the prepared azobenzene polymer after treatment at 150°C for 1h.
[0043] Fig.10 This is a scanning electron microscope image of the nanoimprint of the prepared azobenzene polymer after being treated with solar light for 48 hours.
[0044] It should be noted that these drawings and textual descriptions are not intended to limit the conceptual scope of the present invention in any way, but are intended to illustrate the concept of the present invention for those skilled in the art by referring to specific embodiments. DETAILED DESCRIPTION
[0045] In order to make the purpose, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments will be clearly and completely described below in conjunction with the drawings in the embodiments of the present invention. The following embodiments are used to illustrate the present invention but are not used to limit the scope of the present invention.
[0046] Example 1: Preparation of Compound I-b
[0047] In a 500 mL beaker, add 4-decylaniline (9 g, 38.55 mmol), 9 mL of concentrated hydrochloric acid (36%), ice (10 g), water (20 mL), magnetron and tetrahydrofuran (20 mL), stir vigorously to dissolve and place in an ice-salt bath. In another 100 mL beaker, add water (10 mL), ice (5 g) and sodium nitrite (2.88 g, 41.73 mmol) and stir thoroughly to dissolve, slowly drip it into the aniline solution, and stir at -5 ~ 0℃ for 30 min to generate diazonium salt. In another 500 mL beaker, add phenol (3.96 g, 42.09 mmol), sodium hydroxide (1.8 g, 45.0 mmol), sodium bicarbonate (5.4 g, 9.06 mmol), ice (10 g) and water (20 mL), and slowly drip the diazonium salt into it. The reaction mixture was stirred for 2 h and slowly warmed to room temperature, neutralized with hydrochloric acid to pH = 6, and filtered and washed with water. The crude product was dried, dissolved in a small amount of toluene (10 mL), and a large amount of n-hexane (200 mL) was slowly added for recrystallization. Compound Ⅰ-b was obtained as a reddish brown solid. The yield was 80.1%.
[0048] Example 2: Preparation of Compound I-d
[0049] Potassium carbonate (6.12 g, 44.28 mmol), compound Ⅰ-b (12.5 g, 36.9 mmol), potassium iodide (306 mg, 1.845 mmol) and 6-chloro-1-hexanol (6.03 g, 44.4 mol) and a magnet were added to a 250 mL flask, and N,N-dimethylformamide (60 mL) solvent was added, and the reaction was stirred vigorously at 110 ° C for 12 h. The obtained mixture was cooled to room temperature, extracted with dichloromethane (150 mL), and the organic phase was collected. The crude product was obtained after removing the solvent with a rotary evaporator. The crude product was dissolved in dichloromethane (10 mL), and toluene (200 mL) was slowly added for recrystallization and purification. Compound Ⅰ-d was obtained as a reddish brown solid. The yield was 83.1%.
[0050] Example 3: Preparation of Compound I-g
[0051] Add cis-5-norbornene-exo-2,3-dicarboxylic anhydride (8.2 g, 50.0 mmol), 6-aminocaproic acid (6.55 g, 50 mmol), triethylamine (0.7 mL, 5.0 mmol) and toluene (100 mL) into a round-bottom flask equipped with a magnetic bar and a reflux condenser. Stir the mixture at 110 °C for 19 h, cool to room temperature, and remove the solvent using a rotary evaporator. Dissolve the remaining solid in dichloromethane (200 mL), wash 3 times with distilled water (200 mL), then wash 3 times with saturated sodium chloride solution (200 mL), and dry over anhydrous sodium sulfate. After filtration, use a rotary evaporator to remove the solvent to obtain compound Ⅰ-g as a white solid. The yield is 90.5%.
[0052] Example 4: Preparation of Compound I-h
[0053] Compound Ⅰ-g (9.15 g, 33.0 mmol), compound 3-7 (10.65 g, 30.0 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (6.9 g, 36.0 mmol), N,N-diisopropylethylamine (5.94 mL, 36.0 mmol), 4-dimethylaminopyridine (0.33 g, 3.0 mmol), dichloromethane (150 mL) and a magnetic bar were added to a 500 mL round-bottom flask. Stir and react at room temperature for 24 h. The reaction solution was washed 3 times with distilled water (200 mL), 3 times with saturated sodium chloride solution (200 mL), and dried over anhydrous sodium sulfate. After filtration, the solvent was removed by rotary evaporation to obtain a yellow solid crude product. The solid was dissolved in tetrahydrofuran (30 mL), and methanol (500 mL) was slowly added for recrystallization. After filtration, compound Ⅰ-h was dried to obtain a reddish brown solid with a yield of 81%.
[0054] Example 5: Preparation of azobenzene polymer Ⅰ (n=30)
[0055] Compound I-h (1000 mg) and a magnet were added to the reaction tube. After three nitrogen changes in the transition chamber, the tube was placed in a glove box and 4.0 mL of anhydrous dichloromethane was added to dissolve the monomer. Grubbs third catalyst (53.2 mg) and dichloromethane (600 μL) were added to another vial in the glove box. 400 μL of Grubbs third catalyst solution was quickly added to the reaction tube. After reacting for 5 min, 5 drops of vinyl ethyl ether were added to terminate the reaction. After stirring for 15 min, the tube was taken out of the glove box, the reaction solution was diluted with tetrahydrofuran, and passed through a basic alumina chromatography column to remove the residual Grubbs third catalyst. After removing the solvent using a rotary evaporator, the polymer was dissolved in 4 mL of tetrahydrofuran and slowly added to 80 mL of rapidly stirred methanol to precipitate the polymer. Centrifuge at 10,000 rpm for 5 min and then discard the supernatant. Repeat the above dissolution-precipitation steps twice and dry the solid in a 45°C oven under vacuum for 12 h. Polymer I was obtained as a yellow solid with a yield of 92%.
[0056] Embodiment 6:
[0057] The azobenzene polymer is treated differently, and the specific steps are as follows:
[0058] The azobenzene polymer solid obtained in Example 5 was taken, and then the azobenzene polymer solid was divided into five parts according to mass. The first part of the azobenzene polymer was stored at room temperature away from light, the second part of the azobenzene polymer was placed in an oven at 50°C for 1 hour, the third part of the azobenzene polymer was placed in an oven at 100°C for 1 hour, the fourth part of the azobenzene polymer was placed in an oven at 150°C for 1 hour, and the fifth part of the azobenzene polymer was placed under a sun lamp for 48 hours and then placed in an oven at 40°C for 8 hours.
[0059] Embodiment 7:
[0060] Gel permeation chromatograms of the azobenzene polymer in Test Example 5 initially and after different treatments.
[0061] Figure 2 is the gel permeation chromatogram of the azobenzene polymer prepared in Example 5 after different treatments. Figure 2 It can be seen that the number average molecular weight of the first azobenzene polymer is 27880, and the polymerization distribution index is 1.13. The number average molecular weight of the second azobenzene polymer is 28610, and the polymerization distribution index is 1.13. The number average molecular weight of the third azobenzene polymer is 28442, and the polymerization distribution index is 1.15. The number average molecular weight of the fourth azobenzene polymer is 28296, and the polymerization distribution index is 1.18. The number average molecular weight of the fifth azobenzene polymer is 28103, and the polymerization distribution index is 1.14. From Figure 2 It can be seen that the molecular weight and molecular weight distribution of azobenzene polymer remain basically unchanged after different treatments.
[0062] Embodiment 8:
[0063] The hydrogen nuclear magnetic resonance spectra of the azobenzene polymer in Test Example 5 at the initial stage and after different treatments.
[0064] Figure 3 The following are hydrogen nuclear magnetic resonance spectra of the azobenzene polymers prepared in Example 5 after different treatments. Figure 3 It can be seen that the polymer structure of azobenzene polymer remains unchanged after different treatments.
[0065] Embodiment 9:
[0066] Total reflection infrared spectra of the azobenzene polymer in Test Example 5 initially and after different treatments.
[0067] Figure 4 The total reflection infrared spectra of the azobenzene polymers prepared in Example 5 after different treatments are shown in FIG. Figure 4 It can be seen that the polymer structure of azobenzene polymer remains unchanged after different treatments.
[0068] Embodiment 10:
[0069] Preparation of nanoimprintable azobenzene polymer film. The specific steps are as follows:
[0070] Take five parts of azobenzene polymer in Example 6, then weigh 20 mg of each of the five parts of azobenzene polymer solids and dissolve them in 1 mL of cyclopentanone to form a solution. Finally, spin coat the solution on a square glass slide and place it in a vacuum oven overnight to evaporate the solvent, thereby obtaining an azobenzene polymer film that can be nano-imprinted.
[0071] Embodiment 11:
[0072] The ultraviolet-visible absorption spectrum of the nano-imprintable azobenzene polymer film prepared in Example 10 was tested under different external light conditions.
[0073] Figure 1 FIG. 1 is a UV-visible absorption spectrum of the untreated azobenzene polymer film prepared in Example 10 in the range of 250 nm to 800 nm. Figure 1 It can be seen that under the irradiation of 365 nm UV LED light, the π-π* absorption peak of the azobenzene polymer film decreases while the n-π* absorption peak increases, indicating the transformation of azobenzene from trans to cis structure. Then, under the irradiation of 530 nm visible light LED light, the π-π* absorption peak increases while the n-π* absorption peak decreases, indicating that the cis structure of azobenzene returns to trans.
[0074] Example 12: Nanoimprinting experiment
[0075] Take the untreated azobenzene polymer film obtained in Example 10, and irradiate the film with ultraviolet LED light (365nm) for 5 min to liquefy the polymer film; use a grating type PDMS mold (period is 125 nm, stripe width is 25nm) to imprint it, and after sufficient contact, place it in a vacuum oven at room temperature for 15 min to remove the air remaining in the imprinted structure, and irradiate visible light LED (530 nm) through the PDMS mold for 5 min to solidify the polymer film, and after removing the PDMS mold, the corresponding nanostructure can be obtained.
[0076] Take the five types of azobenzene polymer films obtained in Example 10, and irradiate the films with ultraviolet LED light (365 nm) for 5 min to liquefy the polymer film; use a grating-type PDMS mold (period of 500 nm, stripe width of 200 nm) to imprint it, and after full contact, place it in a vacuum oven and evacuate it at room temperature for 15 min to remove the air remaining in the imprinted structure, and irradiate visible light LED (530 nm) through the PDMS mold for 5 min to solidify the polymer film, and after removing the PDMS mold, the corresponding nanostructure can be obtained.
[0077] Embodiment 13:
[0078] Scanning electron microscope image of the nanostructure obtained by nanoimprinting of the azobenzene polymer film in Test Example 12.
[0079] Figure 5 This is a scanning electron microscope image of a high-precision pattern obtained by nanoimprinting of the untreated azobenzene polymer film prepared in Example 12. The results show that the azobenzene polymer can be used as a nanoimprint photoresist to obtain a high-precision pattern.
[0080] Figure 6-Figure 10 The scanning electron microscope images of the structures of the five types of azobenzene polymer films prepared in Example 12 obtained by nanoimprinting show that the azobenzene polymer has excellent stability when used as a nanoimprint photoresist.
[0081] The above is only a preferred embodiment of the present invention, and does not limit the present invention in any form. Although the present invention has been disclosed as a preferred embodiment, it is not used to limit the present invention. Any technician familiar with this patent can make some changes or modify the technical contents suggested above into equivalent embodiments without departing from the scope of the technical solution of the present invention. However, any simple modification, equivalent change and modification made to the above embodiments according to the technical essence of the present invention without departing from the content of the technical solution of the present invention still fall within the scope of the solution of the present invention.
Claims
1. An azobenzene polymer material, characterized in that Its general structural formula is shown in the following formula I: ; Where n represents the degree of polymerization, which ranges from 5 to 500.
2. The method for preparing the azobenzene polymer material according to claim 1, characterized in that The steps include: Step 1: The aromatic amine compound represented by formula Ⅰ-a is subjected to coupling reaction to obtain the compound represented by formula Ⅰ-b; Step 2: The compound represented by formula Ⅰ-b reacts with the halohydrin represented by formula Ⅰ-c to obtain the compound represented by formula Ⅰ-d; Step 3: The compound represented by formula Ⅰ-e reacts with Ⅰ-f to obtain the compound represented by formula Ⅰ-g; Step 4: The compound represented by formula Ⅰ-g is subjected to esterification reaction with Ⅰ-d to obtain the compound represented by formula Ⅰ-h; Step 5: The compound represented by Formula Ⅰ-h is subjected to a ring-opening metathesis polymerization reaction to obtain a photoinduced solid-liquid transition azobenzene polymer having a structure represented by Formula Ⅰ; 。 3. Use of the azobenzene polymer material according to claim 1 in nanoimprint lithography.
4. The use according to claim 3, characterized in that: The azobenzene polymer material is used as an imprint photoresist for nanoimprinting.
5. The use according to claim 4, characterized in that The steps include: The azobenzene polymer material is dissolved in cyclopentanone to form a solution, and the solution is spin-coated on a carrier, and the solvent is evaporated to obtain a nanoimprint film; the nanoimprint film is irradiated with ultraviolet LED light to liquefy the polymer film, and a certain pressure is applied to the nanoimprint mold with a microstructure so that the liquefied polymer fills the microstructure of the imprint mold, and the air remaining in the imprint structure is removed at room temperature, and then the polymer film is solidified by irradiation with visible light LED light, and the corresponding nanostructure can be obtained after the imprint mold is removed.
6. The use according to claim 5, characterized in that: The azobenzene polymer material is dissolved in cyclopentanone to form a solution, and the concentration of the polymer in the cyclopentanone is 20 mg / mL.
7. The use according to claim 5, characterized in that: The wavelength of the ultraviolet LED is 365 nm.
8. The use according to claim 5, characterized in that: The wavelength of the visible light LED is 530 nm.
Citation Information
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