Optical monomer, preparation method of optical monomer, composition, nanoimprint adhesive, application of nanoimprint adhesive and preparation method of grating

Abstract

The invention discloses an optical monomer and a preparation method thereof, a composition, a nanoimprint adhesive and application thereof, and a preparation method of a grating. The optical monomer provided by the invention mainly comprises a hydroquinone group, a benzotriazole group and a benzosulfide ring structure, so that the prepared nanoimprint adhesive has high refractive index, good ultraviolet resistance and high temperature resistance, does not contain nanoparticles, and does not have the risk of nanoparticle aggregation, thereby prolonging the storage period. Wherein the benzotriazole group has a very good anti-ultraviolet effect. In addition, the optical monomer contains a benzosulfide ring structure, so that the material can be endowed with good high temperature resistance. Moreover, hydroxyl in the optical monomer can form a hydrogen bond with a base material, the adhesive force is improved, the optical monomer is rich in sulfur elements and benzene ring structures, and due to the high molar refractive index of the optical monomer, the optical monomer has a very high refractive index.

Description

Technical Field

[0001] The present application relates to the technical field of optical materials, and in particular to an optical monomer and a preparation method and composition thereof, a nanoimprint glue and an application thereof, and a preparation method of a grating. Background Art

[0002] Currently in the AR / VR field, nanoimprint adhesive can be used to prepare various optical components, such as gratings.

[0003] However, the existing nanoimprint glue mainly increases the refractive index by hybridizing nanoparticles, and the storage period of the glue is almost short (nanoparticles have the risk of agglomeration). In addition, the existing nanoimprint glue has the disadvantages of weak UV resistance and poor adhesion.

[0004] Therefore, how to improve the overall performance of nanoimprint adhesive has become an urgent problem to be solved. Summary of the invention

[0005] In view of this, the present application proposes an optical monomer and a preparation method thereof, a composition, a nanoimprint glue and an application thereof, and a preparation method of a grating.

[0006] The first aspect of the present application provides an optical monomer, comprising: a hydroquinone group; two benzotriazole groups located at the ortho or meta position of the hydroquinone group, a benzothio ring structure connected to the benzotriazole group, and a first substituent group located on the benzothio ring structure;

[0007] Wherein, the structural formula of the benzothiocyclic ring structure is:

[0008] The second aspect of the present application provides a method for preparing an optical monomer, comprising the following steps:

[0009] generating a third compound using the first compound and the second compound;

[0010] The structural formula of the first compound is:

[0011] The structural formula of the second compound is: The structural formula of the third compound is: generating a fifth compound using the third compound and the fourth compound;

[0012] The structural formula of the fourth compound is: The structural formula of the fifth compound is: generating a seventh compound using the fifth compound and the sixth compound;

[0013] The structural formula of the sixth compound is: The structural formula of the seventh compound is: generating a ninth compound using the seventh compound and the eighth compound;

[0014] The structural formula of the eighth compound is: The structural formula of the ninth compound is: generating the optical monomer using the ninth compound;

[0015] The structural formula of the optical monomer is:

[0016]

[0017] The third aspect of the present application provides a method for preparing an optical monomer, comprising the following steps:

[0018] generating a third compound using the first compound and the second compound;

[0019] The structural formula of the first compound is: The structural formula of the second compound is: The structural formula of the third compound is: generating a fifth compound using the third compound and the fourth compound;

[0020] The structural formula of the fourth compound is: The structural formula of the fifth compound is: generating a seventh compound using the fifth compound and the sixth compound;

[0021] The structural formula of the sixth compound is: The structural formula of the seventh compound is: generating a ninth compound using the seventh compound and the eighth compound;

[0022] The structural formula of the eighth compound is: The structural formula of the ninth compound is: generating the optical monomer using the ninth compound;

[0023] The structural formula of the optical monomer is: The fourth aspect of the present application provides a method for preparing an optical monomer, comprising the following steps:

[0024] generating a third compound using the first compound and the second compound;

[0025] The structural formula of the first compound is: The structural formula of the second compound is: The structural formula of the third compound is: generating a fifth compound using the third compound and the fourth compound;

[0026] The structural formula of the fourth compound is: The structural formula of the fifth compound is: generating a seventh compound using the fifth compound and the sixth compound;

[0027] The structural formula of the sixth compound is: The structural formula of the seventh compound is: generating a ninth compound using the seventh compound and the eighth compound;

[0028] The structural formula of the eighth compound is: The structural formula of the ninth compound is: generating the optical monomer using the ninth compound;

[0029] The structural formula of the optical monomer is: The fifth aspect of the present application provides a method for preparing an optical monomer, comprising the following steps:

[0030] generating a third compound using the first compound and the second compound;

[0031] The structural formula of the first compound is: The structural formula of the second compound is: The structural formula of the third compound is: generating a fifth compound using the third compound and the fourth compound;

[0032] The structural formula of the fourth compound is: The structural formula of the fifth compound is: generating a seventh compound using the fifth compound and the sixth compound;

[0033] The structural formula of the sixth compound is: The structural formula of the seventh compound is:

[0034] generating a ninth compound using the seventh compound and the eighth compound;

[0035] The structural formula of the eighth compound is:

[0036] The structural formula of the ninth compound is:

[0037] generating the optical monomer using the ninth compound;

[0038] The structural formula of the optical monomer is:

[0039] The sixth aspect of the present application provides a composition comprising a solvent, a photoinitiator, a leveling agent, a silane coupling agent, a diluent and the above-mentioned optical monomer.

[0040] The seventh aspect of the present application provides a nanoimprint adhesive, which is prepared from the above-mentioned composition.

[0041] The eighth aspect of the present application proposes a method for preparing a grating, comprising the following steps: providing the above-mentioned composition; forming a nanoimprint glue after mixing and filtering; coating the nanoimprint glue on a substrate; and performing grating imprinting on the nanoimprint glue coated on the substrate to form the grating.

[0042] A ninth aspect of the present application provides an application of the nanoimprint adhesive as described above in optical waveguide technology, wherein the nanoimprint adhesive is used to manufacture an optical waveguide device.

[0043] It can be seen from the above technical scheme that the optical monomer proposed in this application mainly contains a hydroquinone group, a benzotriazole group and a benzothio ring structure, so that the prepared nanoimprint glue has a high refractive index, good UV resistance and high temperature resistance, and does not contain nanoparticles, and there is no risk of nanoparticle agglomeration, thereby being able to extend the storage period. Among them, the benzotriazole group has a good anti-ultraviolet effect, and its principle is that the nitrogen and hydroxyl groups in the molecule can form intrinsic hydrogen bonds to form a chelate ring. After absorbing ultraviolet light, the molecule undergoes thermal vibration, the internal hydrogen bonds break, the chelate ring opens, and the ultraviolet energy is converted into heat energy and released, thereby improving the ultraviolet resistance. In addition, the optical monomer contains a benzothio ring structure, which can give the material good high temperature resistance. Moreover, the hydroxyl group in the optical monomer can form a hydrogen bond with the substrate to improve adhesion. The optical monomer is rich in sulfur elements and benzene ring structures, and because of its own high molar refractive index, the optical monomer has a high refractive index. BRIEF DESCRIPTION OF THE DRAWINGS

[0044] In order to more clearly illustrate the technical solutions of the embodiments of the present application, the drawings required for use in the description of the embodiments will be briefly introduced below. Obviously, the drawings described below are some embodiments of the present application. For ordinary technicians in this field, other drawings can be obtained like these drawings without paying any creative work.

[0045] Figure 1 is one of the general structural formulas of the optical monomer proposed in this application;

[0046] Figure 2 is another general structural formula of the optical monomer proposed in this application;

[0047] Figure 3is the structural formula of the first optical monomer proposed in this application;

[0048] Figure 4 is the structural formula of the second optical monomer proposed in this application;

[0049] Figure 5 is the structural formula of the third optical monomer proposed in this application;

[0050] Figure 6 is the structural formula of the fourth optical monomer proposed in this application;

[0051] Figure 7 It is a schematic diagram of the reaction principle of preparing a third compound by using a first compound and a second compound proposed in the present application;

[0052] Figure 8 is a schematic diagram of the reaction principle of preparing the fifth compound by using the third compound and the fourth compound proposed in the present application;

[0053] Fig. 9 is a schematic diagram of the reaction principle of preparing the seventh compound by using the fifth compound and the sixth compound proposed in the present application;

[0054] Fig.10 is a schematic diagram of the reaction principle of preparing the ninth compound by using the seventh compound and the eighth compound proposed in the present application;

[0055] Fig.11 is a schematic diagram of the reaction principle for preparing the sixth compound proposed in the present application;

[0056] Fig.12 It is a schematic diagram of the process of preparing the optical monomer proposed in this application;

[0057] Fig.13 is a schematic diagram of the reaction principle of preparing an optical monomer using the ninth compound proposed in the present application;

[0058] Fig.14 It is a schematic diagram of the process of preparing the grating proposed in this application. DETAILED DESCRIPTION

[0059] The following will be combined with the drawings in the embodiments of the present application to clearly and completely describe the technical solutions in the embodiments of the present application. Obviously, the described embodiments are part of the embodiments of the present application, not all of the embodiments. Based on the embodiments in the present application, all other embodiments obtained by ordinary technicians in this field without creative work are within the scope of protection of this application.

[0060] It should also be understood that the terms used in this application specification are only for the purpose of describing specific embodiments and are not intended to limit the application. As used in this application specification and the appended claims, unless the context clearly indicates otherwise, the singular forms "a", "an" and "the" are intended to include plural forms.

[0061] It should be further understood that the term “and / or” used in the specification and appended claims refers to any combination and all possible combinations of one or more of the associated listed items, and includes these combinations.

[0062] See also Figure 1 and Figure 2 The embodiment of the present application provides an optical monomer, comprising: a hydroquinone group; two benzotriazole groups located at the ortho or meta position of the hydroquinone group, a benzothio ring structure connected to the benzotriazole group, and a first substituent group located on the benzothio ring structure; wherein the structural formula of the benzothio ring structure is:

[0063] It can be understood that the hydroquinone group of the embodiment of the present application has two active groups - hydroxyl groups in the para position, wherein the ortho position of one hydroxyl group is the meta position of the other hydroxyl group, and the meta position of one hydroxyl group is the ortho position of the other hydroxyl group, that is, the benzotriazole group is in the ortho position relative to one of the hydroxyl groups of the hydroquinone group, and in the meta position relative to the other hydroxyl group, so that the two benzotriazole groups are adjacent to one of the hydroxyl groups respectively, and the distance is relatively close, which is easy to form a reaction.

[0064] The optical monomer proposed in the embodiment of the present application mainly comprises a hydroquinone group, a benzotriazole group and a benzosulfide ring structure, so that the prepared nanoimprint glue has a high refractive index, good UV resistance and high temperature resistance, and does not contain nanoparticles, and there is no risk of nanoparticle agglomeration, thereby being able to extend the storage period. Among them, the benzotriazole group and the hydroquinone group can cooperate to achieve effective anti-ultraviolet effect. The principle is that the nitrogen in the molecule of the benzotriazole group is close to the hydroxyl group on the hydroquinone group, and it is easy to form an intrinsic hydrogen bond to form a chelate ring. After absorbing ultraviolet light, the molecule undergoes thermal vibration, the internal hydrogen bond breaks, the chelate ring opens, and the ultraviolet energy is converted into heat energy and released, thereby improving the ultraviolet resistance.

[0065] In addition, the optical monomer contains a benzothiocyclic structure, which can give the material good high temperature resistance. In addition, the hydroxyl group in the optical monomer can form a hydrogen bond with the substrate to improve adhesion. The optical monomer is rich in sulfur elements and benzene ring structures, and due to its own high molar refractive index, the optical monomer has a high refractive index.

[0066] Among them, the benzothiocyclic structure has good high temperature resistance for the following reasons:

[0067] 1. Conjugated knot effect. The benzene ring itself has a strong conjugated system. The electrons are delocalized on the entire benzene ring, making the electronic structure stable. When the benzene ring combines with the sulfur ring to form a benzosulfide ring structure, the sulfur atom and the lone pair of electrons can also interact with the conjugated system of the benzene ring to a certain extent, further enhancing the conjugated effect of the entire molecule. This enhanced conjugated effect makes the electron distribution in the molecule more uniform, and it is not easy to break or rearrange chemical bonds at high temperatures, thus showing better high temperature resistance.

[0068] 2. Steric hindrance effect: the benzothiophene ring has a certain spatial stereostructure. This steric hindrance can reduce the mutual collision between molecules and reduce the decomposition of molecules due to interaction at high temperatures.

[0069] 3. Chemical bond characteristics: In the benzothiophene ring structure, the carbon-sulfur bond has a high bond energy and is not easily destroyed by thermal motion. At the same time, the electronegativity of the sulfur atom is relatively low. After forming a chemical bond with the carbon atom, the electron cloud is more inclined to the carbon atom. This characteristic of electron distribution makes the carbon-sulfur bond have a certain polarity, so that the benzothiophene ring structure can maintain good chemical stability at high temperatures.

[0070] In some embodiments, two benzotriazole groups are symmetrically arranged at the ortho or meta position of the hydroquinone group, and at least one benzothio ring structure is connected to the ortho or meta position of each benzotriazole group, and the types of the first substituent groups on each benzothio ring structure are the same. Thus, the optical monomer of the embodiment of the present application forms a roughly symmetrical structure centered on the hydroquinone group, and the two benzotriazole groups are symmetrically arranged at the ortho or meta position of the hydroquinone group, so that the content of benzotriazole in the whole molecule is increased, thereby forming a larger number of chelate rings in the molecule, and can absorb more ultraviolet light energy during the photocuring process, so that the chelate ring is opened, thereby improving the anti-ultraviolet effect. At the same time, the content of the benzothio ring structure connected to the benzotriazole group is also increased, and more first substituent groups can be set, so that more functional groups can be grafted, increasing the curing rate and the anti-stress effect of the molecule. The overall structure of the molecule is relatively symmetrical, and the performance on both sides of the molecule is relatively uniform, which increases the stress bearing performance in different directions.

[0071] For example, Figure 1 , Figure 3 and Figure 4 As shown, at least one benzothio ring structure is connected to the meta position of the benzene ring of each benzotriazole group, thereby making the symmetry of the entire optical monomer stronger.

[0072] For example, Figure 2 , Figure 5 and Figure 6As shown, at least one benzothio ring structure is connected to the ortho position of the benzene ring of each benzotriazole group, so that the entire optical monomer has extremely high symmetry.

[0073] In some embodiments, the first substituent group includes a substituted or unsubstituted acrylate group. For example, the acrylate group is connected to the sulfur atom of the benzothio ring structure at the end. The acrylate group here can connect the surrounding small molecules to form a large network structure, thereby increasing the mixing speed of the optical monomer and other small molecules.

[0074] See also Figure 1 and Figure 2 In some embodiments, the optical monomer has the following general formula:

[0075] or,

[0076]

[0077] wherein R1, R2, R3, R4, R5 and R6 are each independently selected from substituted or unsubstituted hydrogen, C 1-20 Alkylene, substituted or unsubstituted C 1-30 Alkylene ether group, substituted or unsubstituted C 6-30 Arylene and substituted or unsubstituted C 7-30 One of the aralkylene groups, wherein R1, R2, R3, R4, R5, and R6 may have the same structure or different structures.

[0078] R7 and R8 are each independently selected from hydrogen or methyl, wherein R7 and R8 may have the same structure or different structures.

[0079] R9 and R10 are each independently selected from substituted or unsubstituted hydrogen, C 1-20 Alkyl, substituted or unsubstituted C 1-30 Alkyl ether group, substituted or unsubstituted C 6-30 Aryl, substituted or unsubstituted C 7-30 One of an aralkyl group and a fluoroalkyl group, wherein R9 and R10 may have the same structure or different structures.

[0080] n is a positive integer, 1≤n≤50.

[0081] 43, 44, 45, 46, 47, 48, 49, or 50.

[0082] The optical monomer proposed in the embodiment of the present application mainly comprises a hydroquinone group, a benzotriazole group and a benzosulfide ring structure, so that the prepared nanoimprint glue has a high refractive index, good UV resistance and high temperature resistance, and does not contain nanoparticles, and there is no risk of nanoparticle agglomeration, thereby being able to extend the storage period. Among them, the benzotriazole group and the hydroquinone group can cooperate to achieve effective anti-ultraviolet effect. The principle is that the nitrogen in the molecule of the benzotriazole group is close to the hydroxyl group on the hydroquinone group, and it is easy to form an intrinsic hydrogen bond to form a chelate ring. After absorbing ultraviolet light, the molecule undergoes thermal vibration, the internal hydrogen bond breaks, the chelate ring opens, and the ultraviolet energy is converted into heat energy and released, thereby improving the ultraviolet resistance.

[0083] Among them, the optical monomer of the embodiment of the present application is formed as a whole to form a roughly symmetrical structure centered on the hydroquinone group, and two benzotriazole groups are symmetrically arranged at the ortho or meta position of the hydroquinone group, so that the content of benzotriazole in the whole molecule is increased, thereby forming a larger number of chelate rings in the molecule, and can absorb more ultraviolet light energy during the photocuring process, so that the chelate ring is opened, thereby improving the anti-ultraviolet effect. At the same time, the content of the benzosulfide ring structure connected to the benzotriazole group is also increased, and more first substituent groups can be set, so that more functional groups can be grafted, increasing the curing rate and the anti-stress effect of the molecule. The overall structure of the molecule is relatively symmetrical, and the performance on both sides of the molecule is relatively uniform, which increases the stress bearing performance in different directions.

[0084] In addition, the optical monomer contains a benzothiocyclic structure, which can give the material good high temperature resistance. In addition, the hydroxyl group in the optical monomer can form a hydrogen bond with the substrate to improve adhesion. The optical monomer is rich in sulfur elements and benzene ring structures, and due to its own high molar refractive index, the optical monomer has a high refractive index.

[0085] As an implementation mode, n may be 1, which can facilitate synthesis and reduce production costs while maintaining a high refractive index and good high temperature resistance and UV resistance.

[0086] In an optional embodiment, the optical monomer may include a first optical monomer (eg Figure 3 As shown), the second optical monomer (as Figure 4 As shown), the third optical monomer (as Figure 5 As shown) and the fourth optical monomer (as Figure 6 Of course, in other embodiments, the optical monomer may also be other structures, mainly including a hydroquinone group, a benzotriazole group and a benzothiocyclic structure, within the scope of the above general formula.

[0087] As an implementation manner, the structural formula of the first optical monomer may be:

[0088]

[0089] Among them, the first optical monomer contains a hydroquinone group, a benzotriazole group and a benzosulfide ring structure, so that the prepared nanoimprint glue has a high refractive index, as well as good UV resistance and high temperature resistance. In the field of AR glasses display, the refractive index of the nanoimprint glue prepared by the first optical monomer is greater than 1.7. The grating made by the high refractive index nanoimprint glue can more effectively guide light to the user's eyes and reduce light loss and scattering. It can significantly improve the light efficiency of AR glasses, making virtual images brighter and clearer.

[0090] As an implementation mode, the structural formula of the second optical monomer may be:

[0091]

[0092] Among them, the second optical monomer contains a hydroquinone group, a benzotriazole group and a benzosulfide ring structure, so that the prepared nanoimprint glue has a high refractive index, as well as good UV resistance and high temperature resistance. In the field of AR glasses display, the refractive index of the nanoimprint glue made by the second optical monomer is greater than 1.7. The grating made by the high refractive index nanoimprint glue can more effectively guide light to the user's eyes and reduce light loss and scattering. It can significantly improve the light efficiency of AR glasses, making virtual images brighter and clearer.

[0093] As an implementation manner, the structural formula of the third optical monomer may be:

[0094]

[0095] Among them, the third optical monomer contains a hydroquinone group, a benzotriazole group and a benzosulfide ring structure, so that the prepared nanoimprint glue has a high refractive index, as well as good UV resistance and high temperature resistance. In the field of AR glasses display, the refractive index of the nanoimprint glue made by the third optical monomer is greater than 1.7. The grating made by the high refractive index nanoimprint glue can more effectively guide light to the user's eyes and reduce light loss and scattering. It can significantly improve the light efficiency of AR glasses, making virtual images brighter and clearer.

[0096] As an implementation manner, the structural formula of the fourth optical monomer may be:

[0097]

[0098] Among them, the fourth optical monomer contains a hydroquinone group, a benzotriazole group and a benzosulfide ring structure, so that the prepared nanoimprint glue has a high refractive index, as well as good UV resistance and high temperature resistance. In the field of AR glasses display, the refractive index of the nanoimprint glue made by the fourth optical monomer is greater than 1.7. The grating made by the high refractive index nanoimprint glue can more effectively guide light to the user's eyes and reduce light loss and scattering. It can significantly improve the light efficiency of AR glasses, making virtual images brighter and clearer.

[0099] In some embodiments, the absorption wavelength of the optical monomer is 300nm-400nm. Since the light energy with a wavelength less than 400nm is large, it will destroy the chemical bonds and affect the stability of the compound. The absorption wavelength of the optical monomer in the embodiment of the present application is 300nm-400nm, which can avoid destroying the chemical bonds after absorbing ultraviolet light and improve the stability of the optical monomer. In addition, the nanoimprint glue prepared by the optical monomer of the present application will not be colored, so it is not easy to turn yellow.

[0100] In the prior art, after the organic matter absorbs the blue light in the wavelength range of 450nm-490nm and the violet light in the wavelength range of 400nm-450nm, the remaining light is mixed and appears yellow, that is, yellowing. The optical monomer of the embodiment of the present application has an absorption wavelength of 300nm-400nm, and will not absorb violet light greater than 400nm, nor will it absorb blue light with a wavelength of 450-490nm, and will not absorb natural light with a longer wavelength. Therefore, the prepared nanoimprint glue will not be colored, so it is not easy to turn yellow.

[0101] See also Figures 7 to 12 The present application also provides a method for preparing an optical monomer, comprising the following steps:

[0102] S1, generating a third compound using the first compound and the second compound;

[0103] The structural formula of the first compound is:

[0104] The structural formula of the second compound is:

[0105] The structural formula of the third compound is:

[0106] Illustratively, in step S1, the first compound (33.6 g, 200 mmol) is added to 800 ml of acetic acid solvent and stirred at room temperature for 10 min. Then, the second compound (40.2 g, 200 mmol) is added. After stirring for 60 minutes, a slurry appears. Stirring is continued overnight. Stirring is stopped, and brine is added. The mixture is extracted with ether and purified by column chromatography to obtain an orange-yellow solid. The solid is recrystallized with ethanol to obtain a third compound (64.26 g, 140 mmol, 70% yield).

[0107] S2, generating a fifth compound using the third compound and the fourth compound;

[0108] The structural formula of the fourth compound is:

[0109] The structural formula of the fifth compound is:

[0110] Illustratively, in step S2, the third compound (64.26 g, 140 mmol), ethanol (1000 ml) and sodium hydroxide solution (4N, 1000 ml) are added to the reaction container and heated to 80°C, and then the fourth compound (66.5 g, 4.4 eq) is added and stirred for 15 min to obtain a colorless solid suspension, and the fourth compound (33.3 g, 2.2 eq) is continued to be added to obtain a light yellow liquid, the reaction is stopped, brine is added, ether is extracted, and column chromatography is used for purification to obtain the fifth compound (52.36 g, 85% yield).

[0111] S3, generating a seventh compound using the fifth compound and the sixth compound;

[0112] The structural formula of the sixth compound is:

[0113] The structural formula of the seventh compound is:

[0114] For example, in step S3, at 0°C, in a nitrogen atmosphere, the sixth compound (35.03 g, 143 mmol), triethylamine (30.3 g, 300 mmol) and anhydrous THF 1000 ml (i.e., anhydrous tetrahydrofuran, Tetrahydrofuran) were added, stirred for 1 h, the fifth compound (76.6 g, 238 mmol) was added at 0°C, stirred for 1 h, then returned to room temperature and continued to stir for 36 h, after the reaction was completed, extracted with dichloromethane, and the organic layer was dried with magnesium sulfate. The solvent was removed under reduced pressure, and purified by column chromatography to obtain the seventh compound (65.07 g, 45% yield).

[0115] S4, generating a ninth compound using the seventh compound and the eighth compound;

[0116] The structural formula of the eighth compound is:

[0117] The structural formula of the ninth compound is:

[0118] Illustratively, in step S4, the seventh compound (65.07 g, 64.35 mmol) and the eighth compound (12.6 g, 140 mmol) are reacted in dichloromethane solvent under the action of triethylamine for 21 h to obtain the ninth compound (67.25 g, 85% yield).

[0119] S5, generating an optical monomer using the ninth compound;

[0120] The structural formula of the optical monomer is:

[0121] Illustratively, in step S5, the ninth compound (67.25 g, 54.67 mmol), 475 ml of hydrobromic acid and 493 ml of acetic acid were added to the reaction bottle, and the mixture was boiled and refluxed for 28 h to obtain the first optical monomer (34.62 g, 58% yield).

[0122] See also Fig.13 In some embodiments, the preparation method of the sixth compound comprises the following steps:

[0123] Using the first reactant f1 to generate a first intermediate f2;

[0124] Exemplarily, the first reactant f1 (143 g, 312 mmol) is added to a toluene solution (800 mL), and then an aqueous sodium hydrosulfide solution (16 g of sodium hydrosulfide is dissolved in 100 g of water) is added, and then 0.8 g of tetrabutylammonium bromide is added, and the mixture is stirred and refluxed at 60° C. for 4 h to obtain the first intermediate f2 (48.47 g, 55% yield).

[0125] The structural formula of the first reactant f1 is:

[0126] The structural formula of the first intermediate f2 is:

[0127] Using the first intermediate f2 and the second reactant f3 to generate the second intermediate f4;

[0128] The structural formula of the second reactant f3 is:

[0129] The structural formula of the second intermediate f4 is:

[0130] For example, under anhydrous and oxygen-free conditions, 1000 ml of anhydrous ethanol, the first intermediate f2 (48.47 g, 172 mmol) and the second reactant f3 (65 g, 350 mmol) were added to the reaction device, stirred at room temperature for 30 min, 24 g of sodium ethoxide was dissolved in 400 ml of anhydrous ethanol, and slowly added dropwise to the reaction device, and refluxed at room temperature for 36 h. After the reaction was completed, saturated brine was added, the organic layer was extracted with ether, the solvent was removed under reduced pressure, and the second intermediate f4 (26.91 g, 48% yield) was obtained by column chromatography.

[0131] The second intermediate f4 is used to generate the sixth compound f.

[0132] Illustratively, the second intermediate f4 (26.91 g, 82.56 mmol) is added to a toluene solution (200 mL), and then an aqueous sodium hydrosulfide solution (4 g of sodium hydrosulfide is dissolved in 25 g of water) is added, and then 0.2 g of tetrabutylammonium bromide is added, and the mixture is stirred and refluxed at 100° C. for 8 h to obtain the sixth compound f (15.95 g, 60% yield).

[0133] The present invention also provides a method for preparing an optical monomer, comprising the following steps:

[0134] S1, generating a third compound using the first compound and the second compound;

[0135] generating a third compound using the first compound and the second compound;

[0136] The structural formula of the first compound is:

[0137] The structural formula of the second compound is:

[0138] The structural formula of the third compound is:

[0139] Illustratively, in step S1, the first compound (33.6 g, 200 mmol) is added to 800 ml of acetic acid solvent and stirred at room temperature for 10 min. Then, the second compound (40.2 g, 200 mmol) is added. After stirring for 60 minutes, a slurry appears. Stirring is continued overnight. Stirring is stopped, and brine is added. The mixture is extracted with ether and purified by column chromatography to obtain an orange-yellow solid. The solid is recrystallized with ethanol to obtain a third compound (64.26 g, 140 mmol, 70% yield).

[0140] S2, generating a fifth compound using the third compound and the fourth compound;

[0141] The structural formula of the fourth compound is:

[0142] The structural formula of the fifth compound is:

[0143] Illustratively, in step S2, the third compound (64.26 g, 140 mmol), ethanol (1000 ml) and sodium hydroxide solution (4N, 1000 ml) are added to the reaction container and heated to 80°C, and then the fourth compound (66.5 g, 4.4 eq) is added and stirred for 15 min to obtain a colorless solid suspension, and the fourth compound (33.3 g, 2.2 eq) is continued to be added to obtain a light yellow liquid, the reaction is stopped, brine is added, ether is extracted, and column chromatography is used for purification to obtain the fifth compound (52.36 g, 85% yield).

[0144] S3, generating a seventh compound using the fifth compound and the sixth compound;

[0145] The structural formula of the sixth compound is: The preparation method of the sixth compound can refer to the above embodiment and will not be described in detail here.

[0146] The structural formula of the seventh compound is:

[0147] For example, in step S3, at 0°C, in a nitrogen atmosphere, the sixth compound (35.03 g, 143 mmol), triethylamine (30.3 g, 300 mmol) and anhydrous THF 1000 ml (i.e., anhydrous tetrahydrofuran, Tetrahydrofuran) were added, stirred for 1 h, the fifth compound (76.6 g, 238 mmol) was added at 0°C, stirred for 1 h, then returned to room temperature and continued to stir for 36 h, after the reaction was completed, extracted with dichloromethane, and the organic layer was dried with magnesium sulfate. The solvent was removed under reduced pressure, and purified by column chromatography to obtain the seventh compound (65.07 g, 45% yield).

[0148] S4, generating a ninth compound using the seventh compound and the eighth compound;

[0149] The structural formula of the eighth compound is:

[0150] The structural formula of the ninth compound is:

[0151] Illustratively, in step S4, the seventh compound (65.07 g, 64.35 mmol) and the eighth compound (12.6 g, 140 mmol) are reacted in dichloromethane solvent under the action of triethylamine for 21 h to obtain the ninth compound (67.25 g, 85% yield).

[0152] S5, generating an optical monomer using the ninth compound;

[0153] The structural formula of the optical monomer is:

[0154] Illustratively, in step S5, the ninth compound (67.25 g, 54.67 mmol), 475 ml of hydrobromic acid and 493 ml of acetic acid were added to the reaction bottle, and the mixture was boiled and refluxed for 28 h to obtain the first optical monomer (34.62 g, 58% yield).

[0155] The present invention also provides a method for preparing an optical monomer, comprising the following steps:

[0156] S1, generating a third compound using the first compound and the second compound;

[0157] The structural formula of the first compound is:

[0158] The structural formula of the second compound is:

[0159] The structural formula of the third compound is:

[0160] Illustratively, in step S1, the first compound (33.6 g, 200 mmol) is added to 800 ml of acetic acid solvent and stirred at room temperature for 10 min. Then, the second compound (40.2 g, 200 mmol) is added. After stirring for 60 minutes, a slurry appears. Stirring is continued overnight. Stirring is stopped, and brine is added. The mixture is extracted with ether and purified by column chromatography to obtain an orange-yellow solid. The solid is recrystallized with ethanol to obtain a third compound (64.26 g, 140 mmol, 70% yield).

[0161] S2, generating a fifth compound using the third compound and the fourth compound;

[0162] The structural formula of the fourth compound is:

[0163] The structural formula of the fifth compound is:

[0164] Illustratively, in step S2, the third compound (64.26 g, 140 mmol), ethanol (1000 ml) and sodium hydroxide solution (4N, 1000 ml) are added to the reaction container and heated to 80°C, and then the fourth compound (66.5 g, 4.4 eq) is added and stirred for 15 min to obtain a colorless solid suspension, and the fourth compound (33.3 g, 2.2 eq) is continued to be added to obtain a light yellow liquid, the reaction is stopped, brine is added, ether is extracted, and column chromatography is used for purification to obtain the fifth compound (52.36 g, 85% yield).

[0165] S3, generating a seventh compound using the fifth compound and the sixth compound;

[0166] The structural formula of the sixth compound is: The preparation method of the sixth compound can refer to the above-mentioned embodiment and will not be described in detail here.

[0167] The structural formula of the seventh compound is:

[0168] For example, in step S3, at 0°C, in a nitrogen atmosphere, the sixth compound (35.03 g, 143 mmol), triethylamine (30.3 g, 300 mmol) and anhydrous THF 1000 ml (i.e., anhydrous tetrahydrofuran, Tetrahydrofuran) were added, stirred for 1 h, the fifth compound (76.6 g, 238 mmol) was added at 0°C, stirred for 1 h, then returned to room temperature and continued to stir for 36 h, after the reaction was completed, extracted with dichloromethane, and the organic layer was dried with magnesium sulfate. The solvent was removed under reduced pressure, and purified by column chromatography to obtain the seventh compound (65.07 g, 45% yield).

[0169] S4, generating a ninth compound using the seventh compound and the eighth compound;

[0170] The structural formula of the eighth compound is:

[0171] The structural formula of the ninth compound is:

[0172] Illustratively, in step S4, the seventh compound (65.07 g, 64.35 mmol) and the eighth compound (12.6 g, 140 mmol) are reacted in dichloromethane solvent under the action of triethylamine for 21 h to obtain the ninth compound (67.25 g, 85% yield).

[0173] S5, generating an optical monomer using the ninth compound;

[0174] The structural formula of the optical monomer is:

[0175] Illustratively, in step S5, the ninth compound (67.25 g, 54.67 mmol), 475 ml of hydrobromic acid and 493 ml of acetic acid were added to the reaction bottle, and the mixture was boiled and refluxed for 28 h to obtain the first optical monomer (34.62 g, 58% yield).

[0176] The present invention also provides a method for preparing an optical monomer, comprising the following steps:

[0177] S1, generating a third compound using the first compound and the second compound;

[0178] The structural formula of the first compound is:

[0179] The structural formula of the second compound is:

[0180] The structural formula of the third compound is:

[0181] Illustratively, in step S1, the first compound (33.6 g, 200 mmol) is added to 800 ml of acetic acid solvent and stirred at room temperature for 10 min. Then, the second compound (40.2 g, 200 mmol) is added. After stirring for 60 minutes, a slurry appears. Stirring is continued overnight. Stirring is stopped, and brine is added. The mixture is extracted with ether and purified by column chromatography to obtain an orange-yellow solid. The solid is recrystallized with ethanol to obtain a third compound (64.26 g, 140 mmol, 70% yield).

[0182] S2, generating a fifth compound using the third compound and the fourth compound;

[0183] The structural formula of the fourth compound is:

[0184] The structural formula of the fifth compound is:

[0185] Illustratively, in step S2, the third compound (64.26 g, 140 mmol), ethanol (1000 ml) and sodium hydroxide solution (4N, 1000 ml) are added to the reaction container and heated to 80°C, and then the fourth compound (66.5 g, 4.4 eq) is added and stirred for 15 min to obtain a colorless solid suspension, and the fourth compound (33.3 g, 2.2 eq) is continued to be added to obtain a light yellow liquid, the reaction is stopped, brine is added, ether is extracted, and column chromatography is used for purification to obtain the fifth compound (52.36 g, 85% yield).

[0186] S3, generating a seventh compound using the fifth compound and the sixth compound;

[0187] The structural formula of the sixth compound is: The preparation method of the sixth compound can refer to the above embodiment and will not be described in detail here.

[0188] The structural formula of the seventh compound is:

[0189] For example, in step S3, at 0°C, in a nitrogen atmosphere, the sixth compound (35.03 g, 143 mmol), triethylamine (30.3 g, 300 mmol) and anhydrous THF 1000 ml (i.e., anhydrous tetrahydrofuran, Tetrahydrofuran) were added, stirred for 1 h, the fifth compound (76.6 g, 238 mmol) was added at 0°C, stirred for 1 h, then returned to room temperature and continued to stir for 36 h, after the reaction was completed, extracted with dichloromethane, and the organic layer was dried with magnesium sulfate. The solvent was removed under reduced pressure, and purified by column chromatography to obtain the seventh compound (65.07 g, 45% yield).

[0190] S4, generating a ninth compound using the seventh compound and the eighth compound;

[0191] The structural formula of the eighth compound is:

[0192] The structural formula of the ninth compound is:

[0193] Illustratively, in step S4, the seventh compound (65.07 g, 64.35 mmol) and the eighth compound (12.6 g, 140 mmol) are reacted in dichloromethane solvent under the action of triethylamine for 21 h to obtain the ninth compound (67.25 g, 85% yield).

[0194] S5, generating an optical monomer using the ninth compound;

[0195] The structural formula of the optical monomer is:

[0196] Illustratively, in step S5, the ninth compound (67.25 g, 54.67 mmol), 475 ml of hydrobromic acid and 493 ml of acetic acid were added to the reaction bottle, and the mixture was boiled and refluxed for 28 h to obtain the first optical monomer (34.62 g, 58% yield).

[0197] The present application also provides a composition, which includes a solvent, a photoinitiator, a leveling agent, a silane coupling agent, a diluent and the above optical monomer. Thus, a nanoimprint adhesive with a high refractive index and good UV resistance and high temperature resistance can be prepared by using the composition with the above optical monomer. The diluent is added to the component, so that the prepared film layer can be uniform and the imprint effect can be improved.

[0198] In an optional embodiment, the composition may include the following components in weight percentage: solvent 10%-70%; photoinitiator 0.1%-10%; leveling agent 0.1%-5%; silane coupling agent 0.1%-5%; diluent 10%-50%; optical monomer 10%-70%.

[0199] In an optional embodiment, the composition may include the following components in weight percentage: 10% solvent; 5% photoinitiator; 3% leveling agent; 2% silane coupling agent; 10% diluent; and 70% optical monomer.

[0200] In an optional embodiment, the composition may include the following components in weight percentage: 70% solvent; 5% photoinitiator; 3% leveling agent; 2% silane coupling agent; 10% diluent; and 10% optical monomer.

[0201] In an optional embodiment, the composition may include the following components in weight percentage: 30% solvent; 5% photoinitiator; 3% leveling agent; 2% silane coupling agent; 50% diluent; and 10% optical monomer.

[0202] In an optional embodiment, the composition may include the following components in weight percentage: 50% solvent; 0.1% photoinitiator; 0.5% leveling agent; 0.4% silane coupling agent; 10% diluent; and 39% optical monomer.

[0203] In an optional embodiment, the composition may include the following components in weight percentage: 50% solvent; 0.5% photoinitiator; 0.1% leveling agent; 0.4% silane coupling agent; 10% diluent; and 39% optical monomer.

[0204] In an optional embodiment, the composition may include the following components in weight percentage: 50% solvent; 0.5% photoinitiator; 0.4% leveling agent; 0.1% silane coupling agent; 10% diluent; and 39% optical monomer.

[0205] In an optional embodiment, the composition may include the following components in weight percentage: 40% solvent; 10% photoinitiator; 5% leveling agent; 5% silane coupling agent; 10% diluent; and 30% optical monomer.

[0206] In an optional embodiment, the composition may include the following components by weight: 10 g of solvent; 10 g of optical monomer; 2 g of diluent; 0.3 g of photoinitiator; 0.03 g of leveling agent; and 0.05 g of silane coupling agent.

[0207] In an optional embodiment, the solvent is at least one of propylene glycol methyl ether acetate, ethyl acetate, dichloromethane, ethanol, isopropanol, butyl acetate, butyl acetate, tetrahydrofuran, dimethyl sulfoxide, N,N-dimethylformamide, tetramethylethylenediamine, and carbon tetrachloride.

[0208] In an optional embodiment, the absorption wavelength of the photoinitiator is 368nm-420nm, so that the photoinitiator can initiate the polymerization reaction under light conditions without affecting the overall light transmittance of the nanoimprint glue.

[0209] In an optional embodiment, the photoinitiator is thioxanthone, thioxanthone derivatives, 7,7-dimethyl-2,3-dioxobicyclo[2.2.1]heptane-1-carboxylic acid chloride, 7,7-dimethyl-2,3-dioxobicyclo[2.2.1]heptane-1-carboxy-2-methyl ester, diethoxyacetophenone, 4-tert-butyltrichloroacetophenone, 2,4,6-trimethylbenzoyl-diphenylphosphine oxide, 2-dimethylaminoethyl benzoate, 4,6-trimethylbenzoyldimethoxyphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide, benzoyldiphenylphosphine oxide, 2,4,6-trimethylbenzoyldiethoxyphenylphosphine oxide, benzoyldiethoxyphosphine oxide, benzophenone, benzophenone derivatives, benzil, benzil derivatives, anthraquinone, anthraquinone derivatives, benzoin, benzoin methyl The invention further comprises at least one of benzoyl ether, benzoin ethyl ether, benzoin propyl ether, benzoin isobutyl ether, benzyl dimethyl ketal, p-dimethylaminoethyl benzoate, diphenyl disulfide, camphorquinone, 7,7-dimethyl-2,3-dioxobicyclo[2.2.1]heptane-1-carboxylic acid, 7,7-dimethyl-2,3-dioxobicyclo[2.2.1]heptane-1-carboxylic acid-2-bromoethyl ester, 2-methyl-1-[4-(methylthio)phenyl-13-yl]-2-morpholinopropane-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-1-butanone, α-aminoalkylphenone derivatives, phenyl-glyoxylic acid-methyl ester or oxy-phenyl-acetic acid 2-[2-oxy-2-phenyl-ethoxy-ethoxy]-ethyl ester and oxy-phenyl-acetic acid 2-[2-hydroxy-ethoxy]-ethyl ester.

[0210] In an optional embodiment, the leveling agent is one of BYK331, BYK370, BYK3505 and BYK348. Specifically, BYK331, BYK370, BYK3505 and BYK348 are leveling agents produced by BYK of Germany. BYK series leveling agents have excellent leveling performance.

[0211] In an optional embodiment, the silane coupling agent is one of KH570, KH550 and KH560. Specifically, KH570, KH550 and KH560 are silane coupling agents produced by the Chinese Academy of Sciences.

[0212] Among them, KH570 is also known as γ-methacryloxypropyltrimethoxysilane, which is an organic functional silane coupling agent. KH570 is used to improve the mechanical and electrical properties of nanoimprint glue.

[0213] Among them, KH550, also known as γ-aminopropyltriethoxysilane, can enhance the adhesion of nanoimprint adhesive and improve the mechanical, water-resistant and anti-aging properties of the product.

[0214] Among them, KH560, also known as γ-glycidyloxypropyltrimethoxysilane, can improve the strength performance of nanoimprint glue.

[0215] In an optional embodiment, the diluent is at least one of OPPEA, 2206, and 9,9-bis[4-(2-acryloyloxyethoxy)phenyl]fluorene. Among them, OPPEA is a diluent monomer o-phenylphenoxyethyl acrylate purchased from Sartomer. 2206 is a diluent monomer ETERMER 2206 (bifunctional acrylate) purchased from Changxing Chemical, and 9,9-bis[4-(2-acryloyloxyethoxy)phenyl]fluorene is purchased from Tokyo Chemical Industry Co., Ltd. (i.e., Tokyo Chemical Industry, abbreviated as TCI).

[0216] The embodiment of the present application also provides a nano-imprint adhesive, which is prepared according to the above composition. Exemplarily, a solvent, a photoinitiator, a leveling agent, a silane coupling agent, a diluent and an optical monomer are placed in a reaction container and mixed and filtered to form a nano-imprint adhesive. Since the nano-imprint adhesive is prepared from the above composition, the composition includes the above optical monomer, and therefore, the nano-imprint adhesive proposed in the embodiment of the present application has a high refractive index, as well as good UV resistance and high temperature resistance.

[0217] See also Fig.14 The present application also provides a method for preparing a grating, comprising the following steps:

[0218] S10, providing the above composition, that is, placing the solvent, photoinitiator, leveling agent, silane coupling agent, diluent and optical monomer in a reaction container.

[0219] S20, forming a nanoimprinting glue after mixing and filtering;

[0220] S30, coating the nanoimprint glue on the substrate.

[0221] S40, performing grating imprinting on the nanoimprint glue coated on the substrate to form a grating.

[0222] In the preparation method of the grating of the embodiment of the present application, the selection of the solvent, the photoinitiator, the leveling agent, the silane coupling agent and the diluent can refer to the above embodiment and will not be repeated here. The optical monomer can select any one of the first optical monomer, the second optical monomer, the third optical monomer and the fourth optical monomer.

[0223] Among them, the optical monomer mainly contains hydroquinone group, benzotriazole group and benzosulfide ring structure, so that the prepared nanoimprint glue and grating have high refractive index, good UV resistance and high temperature resistance. Photoinitiator is used to start the polymerization reaction under light conditions, and leveling agent can help the nanoimprint glue to spread evenly on the substrate, reducing bubbles and surface defects. Silane coupling agent can enhance the adhesion between materials to improve the overall performance of the prepared nanoimprint glue.

[0224] In an optional embodiment, in step S30, coating the nanoimprint glue on the substrate includes: coating the nanoimprint glue on the wafer for coating, the coating speed is 1000rpm-10000rpm, and the coating time is 10s-300s. Exemplarily, the coating speed can be 1000rpm, 2000rpm, 3000rpm, 4000rpm, 5000rpm, 6000rpm, 7000rpm, 8000rpm, 9000rpm or 10000rpm, etc., and the coating time can be 10s, 20s, 30s, 40s, 50s, 60s, 70s, 80s, 90s, 100s, 2000s or 300s, etc.

[0225] In an optional embodiment, in step S20, the nanoimprint glue can be obtained by vigorously mixing for 2 hours under light-proof conditions and then filtering with a 0.45 um syringe filter.

[0226] In an optional embodiment, in step S30, the nanoimprint glue can be coated on a 4-inch wafer, with a coating speed of 3000 rpm and a coating time of 60 s. Since the coating speed and coating time will affect the thickness and uniformity of the formed film, the embodiment of the present application sets the coating speed to 3000 rpm and the coating time to 60 s to coat the nanoimprint glue on the wafer to obtain a better film thickness and uniformity.

[0227] The embodiment of the present application also provides an application of nanoimprint adhesive in optical waveguide technology, and the nanoimprint adhesive is used to make optical waveguide devices. For example, in the field of AR glasses display, the nanoimprint adhesive can produce a high-precision grating structure through nanoimprint technology to improve the performance and efficiency of optical waveguide devices. In the field of AR glasses display, the grating made by the high-refractive index nanoimprint adhesive can more effectively guide light to the user's eyes, reducing light loss and scattering. The light efficiency of AR glasses can be significantly improved, making the virtual image brighter and clearer.

[0228] The optical monomer and nanoimprint adhesive of the present application are further described below in combination with specific embodiments and test data.

[0229] Example 1

[0230] Propylene glycol methyl ether acetate (10 g), the first optical monomer (10 g), 9,9-bis[4-(2-acryloyloxyethoxy)phenyl]fluorene (2 g), 2,4,6-trimethylbenzoyl-diphenylphosphine oxide (0.3 g), BYK370 (0.03 g), and KH570 (0.05 g) were added to a 50 mL volumetric flask, mixed vigorously for 2 h under light-proof conditions, and then filtered with a 0.45 um syringe filter to obtain a nanoimprint glue. The nanoimprint glue was subjected to a sizing treatment (rotation speed 3500, time 60 s) on a 4-inch glass wafer, and then grating imprinted to form a grating. The refractive index, transmittance, yellowness, fog, UV aging, xenon lamp aging, and grating structure SEM test were measured.

[0231] Example 2

[0232] Propylene glycol methyl ether acetate (10 g), the second optical monomer (10 g), 9,9-bis[4-(2-acryloyloxyethoxy)phenyl]fluorene (2 g), 2,4,6-trimethylbenzoyl-diphenylphosphine oxide (0.3 g), BYK370 (0.03 g), and KH570 (0.05 g) were added to a 50 mL volumetric flask, mixed vigorously for 2 h under light-proof conditions, and then filtered with a 0.45 um syringe filter to obtain a nanoimprint glue. The nanoimprint glue was homogenized on a 4-inch glass wafer (speed 3500, time 60 s), and then grating imprinted to form a grating. The refractive index, transmittance, yellowness, fog, UV aging, xenon lamp aging, and grating structure SEM test were measured.

[0233] Example 3

[0234] Propylene glycol methyl ether acetate (10 g), the third optical monomer (10 g), 9,9-bis[4-(2-acryloyloxyethoxy)phenyl]fluorene (2 g), 2,4,6-trimethylbenzoyl-diphenylphosphine oxide (0.3 g), BYK370 (0.03 g), and KH570 (0.05 g) were added to a 50 mL volumetric flask, mixed vigorously for 2 h under light-proof conditions, and then filtered with a 0.45 um syringe filter to obtain a nanoimprint glue. The nanoimprint glue was homogenized on a 4-inch glass wafer (speed 3500, time 60 s), and then grating imprinted to form a grating. The refractive index, transmittance, yellowness, fog, UV aging, xenon lamp aging, and grating structure SEM test were measured.

[0235] Example 4

[0236] Propylene glycol methyl ether acetate (10 g), the fourth optical monomer (10 g), 9,9-bis[4-(2-acryloyloxyethoxy)phenyl]fluorene (2 g), 2,4,6-trimethylbenzoyl-diphenylphosphine oxide (0.3 g), BYK370 (0.03 g), and KH570 (0.05 g) were added to a 50 mL volumetric flask, mixed vigorously for 2 h under light-proof conditions, and then filtered with a 0.45 um syringe filter to obtain a nanoimprint glue. The nanoimprint glue was homogenized on a 4-inch glass wafer (speed 3500, time 60 s), and then grating imprinted to form a grating. The refractive index, transmittance, yellowness, fog, UV aging, xenon lamp aging, and grating structure SEM test were measured.

[0237] Comparative Example 1

[0238] The commercially available imprinting glue HZ-1 was spread on a 4-inch glass wafer (rotation speed 3500, time 60s), and then grating imprinting was performed to form a grating. The refractive index, transmittance, yellowness, fog, UV aging, xenon lamp aging, and grating structure SEM test were measured.

[0239] Comparative Example 2

[0240] The commercially available embossing glue HZ-2 was spread on a 4-inch glass wafer (rotation speed 3500, time 60s), and then grating embossing was performed to form a grating. The refractive index, transmittance, yellowness, fog, UV aging, xenon lamp aging, and grating structure SEM test were measured.

[0241] Comparative Example 3

[0242] Add propylene glycol methyl ether acetate (10g), 9,9-bis[4-(2-acryloyloxyethoxy)phenyl]fluorene (2g), 2,4,6-trimethylbenzoyl-diphenylphosphine oxide (0.3g), BYK370 (0.03g), KH570 (0.05g) to a 50mL volumetric flask, mix vigorously for 2h under light-proof conditions, and then filter with a 0.45um syringe filter to obtain a nanoimprint glue. The nanoimprint glue is homogenized on a 4-inch glass wafer (speed 3500, time 60s), and then grating imprinted to form a grating. Measure the refractive index, transmittance, yellowness, fog, UV aging, xenon lamp aging, and grating structure SEM test.

[0243] The gratings prepared in the above-mentioned Examples 1 to 4 and Comparative Examples 1 to 3 were subjected to performance tests, and the test results are shown in Table 1.

[0244] Among them, the performance test methods and standards are as follows:

[0245] (1) Refractive index: tested using an ellipsometer (ME-L Mueller Matrix Spectroscopic Ellipsometer, Yiguang Technology);

[0246] (2) Light transmittance: high-precision haze meter (HM-150, Murakami Color MCRL);

[0247] (3) Yellowness: high-precision haze meter (HM-150, Murakami Color MCRL);

[0248] (4) Haze: high-precision haze meter (HM-150, Murakami Color MCRL);

[0249] (5) Adhesion: 100-grid test;

[0250] (6) UV aging: UV aging test box (light source power 650mw, irradiation 4h, stop 4h as one cycle, a total of 24 cycles);

[0251] (7) Xenon lamp aging: Xenon lamp aging test chamber (Q-SUN Xe-1, Q-LAB);

[0252] (8) Structural shape preservation: SEM (SU5000 Hitachi) was used to observe the micro-nanostructure;

[0253] Table 1

[0254]

[0255] From Examples 1-4 and Comparative Examples 1-3 in Table 1, it can be seen that the refractive index of the gratings prepared in Examples 1 to 4 of the present application is comparable to that of the gratings prepared by the currently commercially available nanoimprint glue (containing nanoparticles). However, the light transmittance, UV resistance and high temperature resistance are all higher than those of the gratings prepared by the commercially available nanoimprint glue (containing nanoparticles).

[0256] Among them, after aging with ultraviolet xenon lamp, the yellowness change of the gratings prepared in Examples 1 to 4 of the present application is much lower than the yellowness change of the gratings made of commercially available nanoimprint glue. This is because the benzotriazole group in the molecules of the optical monomers in Examples 1 to 4 of the present application has a good anti-ultraviolet effect. The principle is that nitrogen and hydroxyl groups in the molecule can form intrinsic hydrogen bonds to form chelate rings. After absorbing ultraviolet light, the molecule undergoes thermal vibration, the internal hydrogen bonds break, the chelate ring opens, and the ultraviolet energy is converted into heat energy and released.

[0257] In addition, Comparative Example 3 is a multi-benzene ring structure, which has cracks after imprinting. This is because the rigid groups in its molecular chain make it easy for the material to accumulate internal stress during the nanoimprint cross-linking and curing process, and the internal stress develops into cracks during demolding.

[0258] The gratings prepared in Examples 1 to 4 of the present application not only have normal structural shape retention and high adhesion, but also have low yellowness change after UV aging and low yellowness change after xenon lamp aging. They not only have a high refractive index, but also have good UV resistance and high temperature resistance. They do not contain nanoparticles and there is no risk of nanoparticle agglomeration, thereby extending the storage period.

[0259] Those skilled in the art may combine and associate different embodiments or examples and features of different embodiments or examples described in this specification without mutual contradiction.

[0260] The above is only a specific implementation of the present application, but the protection scope of the present application is not limited thereto. Any technician familiar with the technical field can easily think of various equivalent modifications or replacements within the technical scope disclosed in the present application, and these modifications or replacements should be included in the protection scope of the present application. Therefore, the protection scope of the present application shall be based on the protection scope of the claims.

Claims

1. An optical monomer, characterized in that: include: A hydroquinone group; two benzotriazole groups located at the ortho position or the meta position of the hydroquinone group, a benzothio ring structure connected to the benzotriazole group, and a first substituent group located on the benzothio ring structure; Wherein, the structural formula of the benzothiocyclic ring structure is:

2. The optical monomer according to claim 1, wherein: The two benzotriazole groups are symmetrically arranged at the ortho or meta position of the hydroquinone group, and at least one benzothio ring structure is connected to the ortho or meta position of each benzotriazole group, and the first substituent group on each benzothio ring structure is of the same type.

3. The optical monomer according to claim 2, characterized in that: The first substituent group includes a substituted or unsubstituted acrylate group.

4. The optical monomer according to claim 1, characterized in that: The optical monomer has the following general formula: or, wherein R1, R2, R3, R4, R5 and R6 are each independently selected from substituted or unsubstituted hydrogen, C 1-20 Alkylene, substituted or unsubstituted C 1-30 Alkylene ether group, substituted or unsubstituted C 6-30 Arylene and substituted or unsubstituted C 7-30 One of the arylalkylene groups; R7 and R8 are each independently selected from hydrogen or methyl; R9 and R10 are each independently selected from substituted or unsubstituted hydrogen, C 1-20 Alkyl, substituted or unsubstituted C 1-30 Alkyl ether group, substituted or unsubstituted C 6-30 Aryl, substituted or unsubstituted C 7-30 One of an aralkyl group and a fluoroalkyl group; n is a positive integer, 1≤n≤50.

5. The optical monomer according to claim 4, characterized in that: The structural formula of the optical monomer is as follows: or, or, or, 6. The optical monomer according to claim 4 or 5, characterized in that: The absorption wavelength of the optical monomer is 300nm-400nm.

7. A method for preparing an optical monomer, characterized in that: The steps include: generating a third compound using the first compound and the second compound; The structural formula of the first compound is: The structural formula of the second compound is: The structural formula of the third compound is: generating a fifth compound using the third compound and the fourth compound; The structural formula of the fourth compound is: The structural formula of the fifth compound is: generating a seventh compound using the fifth compound and the sixth compound; The structural formula of the sixth compound is: The structural formula of the seventh compound is: generating a ninth compound using the seventh compound and the eighth compound; The structural formula of the eighth compound is: The structural formula of the ninth compound is: generating the optical monomer using the ninth compound; The structural formula of the optical monomer is:

8. The preparation method according to claim 7, characterized in that: The preparation method of the sixth compound comprises the following steps: Using the first reactant f1 to generate a first intermediate f2; The structural formula of the first reactant f1 is: The structural formula of the first intermediate f2 is: Using the first intermediate f2 and the second reactant f3 to generate the second intermediate f4; The structural formula of the second reactant f3 is: The structural formula of the second intermediate f4 is: The sixth compound is generated by utilizing the second intermediate f4.

9. A method for preparing an optical monomer, characterized in that: The steps include: generating a third compound using the first compound and the second compound; The structural formula of the first compound is: The structural formula of the second compound is: The structural formula of the third compound is: generating a fifth compound using the third compound and the fourth compound; The structural formula of the fourth compound is: The structural formula of the fifth compound is: generating a seventh compound using the fifth compound and the sixth compound; The structural formula of the sixth compound is: The structural formula of the seventh compound is: generating a ninth compound using the seventh compound and the eighth compound; The structural formula of the eighth compound is: The structural formula of the ninth compound is: generating the optical monomer using the ninth compound; The structural formula of the optical monomer is:

10. A method for preparing an optical monomer, characterized in that: The steps include: generating a third compound using the first compound and the second compound; The structural formula of the first compound is: The structural formula of the second compound is: The structural formula of the third compound is: generating a fifth compound using the third compound and the fourth compound; The structural formula of the fourth compound is: The structural formula of the fifth compound is: generating a seventh compound using the fifth compound and the sixth compound; The structural formula of the sixth compound is: The structural formula of the seventh compound is: generating a ninth compound using the seventh compound and the eighth compound; The structural formula of the eighth compound is: The structural formula of the ninth compound is: generating the optical monomer using the ninth compound; The structural formula of the optical monomer is:

11. A method for preparing an optical monomer, characterized in that: The steps include: generating a third compound using the first compound and the second compound; The structural formula of the first compound is: The structural formula of the second compound is: The structural formula of the third compound is: generating a fifth compound using the third compound and the fourth compound; The structural formula of the fourth compound is: The structural formula of the fifth compound is: generating a seventh compound using the fifth compound and the sixth compound; The structural formula of the sixth compound is: The structural formula of the seventh compound is: generating a ninth compound using the seventh compound and the eighth compound; The structural formula of the eighth compound is: The structural formula of the ninth compound is: generating the optical monomer using the ninth compound; The structural formula of the optical monomer is:

12. A composition, characterized in that The composition comprises a solvent, a photoinitiator, a leveling agent, a silane coupling agent, a diluent and the optical monomer according to any one of claims 1 to 6.

13. The composition according to claim 12, characterized in that The composition includes the following components in weight percentage: Solvent 10%-70%; Photoinitiator 0.1%-10%; Leveling agent 0.1%-5%; Silane coupling agent 0.1%-5%; Diluent 10%-50%; 10%-70% of the optical monomer according to any one of claims 1 to 6.

14. The composition according to claim 12, characterized in that The solvent is at least one of propylene glycol methyl ether acetate, ethyl acetate, dichloromethane, ethanol, isopropanol, butyl acetate, butyl acetate, tetrahydrofuran, dimethyl sulfoxide, N,N-dimethylformamide, tetramethylethylenediamine, and carbon tetrachloride; and / or, The absorption wavelength of the photoinitiator is 368nm-420nm; and / or, The photoinitiator is thioxanthone, thioxanthone derivatives, 7,7-dimethyl-2,3-dioxobicyclo[2.2.1]heptane-1-carboxylic acid chloride, 7,7-dimethyl-2,3-dioxobicyclo[2.2.1]heptane-1-carboxyl-2-methyl ester, diethoxyacetophenone, 4-tert-butyltrichloroacetophenone, 2,4,6-trimethylbenzoyl-diphenylphosphine oxide, 2-dimethylaminoethyl benzoate, 4,6-trimethylbenzoyldimethoxyphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide, benzoyldiphenylphosphine oxide, 2,4,6-trimethylbenzoyldiethoxyphenylphosphine oxide, benzoyldiethoxyphosphine oxide, benzophenone, benzophenone derivatives, benzil, benzil derivatives, anthraquinone, anthraquinone derivatives, benzoin, benzoin methyl ether, benzoin at least one of benzoin ethyl ether, benzoin propyl ether, benzoin isobutyl ether, benzyl dimethyl ketal, p-dimethylaminoethyl benzoate, diphenyl disulfide, camphorquinone, 7,7-dimethyl-2,3-dioxobicyclo[2.2.1]heptane-1-carboxylic acid, 7,7-dimethyl-2,3-dioxobicyclo[2.2.1]heptane-1-carboxy-2-bromoethyl ester, 2-methyl-1-[4-(methylthio)phenyl-13-yl]-2-morpholinopropane-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-1-butanone, α-aminoalkylphenone derivatives, phenyl-glyoxylic acid-methyl ester or oxy-phenyl-acetic acid 2-[2-oxy-2-phenyl-ethoxy-ethoxy]-ethyl ester and oxy-phenyl-acetic acid 2-[2-hydroxy-ethoxy]-ethyl ester; and / or, The leveling agent is one of BYK331, BYK370, BYK3505 and BYK348; and / or, The silane coupling agent is one of KH570, KH550 and KH560.

15. A nanoimprint adhesive, characterized in that: The nanoimprint glue is prepared according to the composition according to any one of claims 12 to 14.

16. A method for preparing a grating, characterized in that: The steps include: Providing a composition as claimed in any one of claims 12 to 14; After mixing and filtering, a nanoimprinting glue is formed; coating the nanoimprint glue on a substrate; The nanoimprint glue coated on the substrate is subjected to grating imprinting to form the grating.

17. The preparation method according to claim 16, characterized in that: The step of coating the nanoimprint glue on the substrate comprises: coating the nanoimprint glue on the wafer for coating, the coating speed is 1000rpm-10000rpm, and the coating time is 10s-300s.

18. An application of the nanoimprint adhesive as claimed in claim 15 in optical waveguide technology, characterized in that: The nanoimprint glue is used for making optical waveguide devices.

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