Optical monomer and preparation method thereof, composition, resin material and preparation method and application thereof

Abstract

The invention discloses an optical monomer and a preparation method thereof, a composition, a resin material and a preparation method and application thereof. The optical monomer provided by the invention mainly comprises a hydroquinone group, a benzotriazole group and a phenyl sulfide group, so that the prepared resin material has high refractive index and good ultraviolet resistance and heat resistance. Wherein the benzotriazole group has a very good anti-ultraviolet effect. In addition, the optical monomer contains a phenyl sulfide group, 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 resin material and a preparation method and application thereof. Background Art

[0002] The application of optical resin is indispensable in the optical waveguide technology of AR / VR glasses. The current application scenarios of AR / VR glasses require not only optical resins with high refractive index, but also other properties such as UV resistance and heat resistance. However, existing optical resins are difficult to meet the above requirements.

[0003] Therefore, how to improve the overall performance of optical resins has become an urgent problem to be solved. Summary of the invention

[0004] In view of this, the present application proposes an optical monomer and a preparation method thereof, a composition, a resin material and a preparation method and application thereof.

[0005] 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 phenylene sulfide group connected to the benzotriazole group, and a first substituent group located on the phenylene sulfide group.

[0006] The second aspect of the present application provides a method for preparing an optical monomer, comprising the following steps:

[0007] generating a third compound using the first compound and the second compound;

[0008] The structural formula of the first compound is:

[0009] The structural formula of the second compound is:

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

[0011] 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:

[0014]

[0015] generating a ninth compound using the seventh compound and the eighth compound;

[0016] The structural formula of the eighth compound is: The structural formula of the ninth compound is:

[0017]

[0018] generating the optical monomer using the ninth compound;

[0019] The structural formula of the optical monomer is:

[0020]

[0021] The third aspect of the present application provides a method for preparing an optical monomer, comprising the following steps:

[0022] generating a third compound using the first compound and the second compound;

[0023] 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;

[0024] 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;

[0025] The structural formula of the sixth compound is: The structural formula of the seventh compound is:

[0026]

[0027] 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:

[0029]

[0030] generating the optical monomer using the ninth compound;

[0031] The structural formula of the optical monomer is:

[0032]

[0033] A fourth aspect of the present application provides a method for preparing an optical monomer, comprising the following steps: generating a third compound using a first compound and a second compound;

[0034] 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;

[0035] 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;

[0036] 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;

[0037] The structural formula of the eighth compound is: The structural formula of the ninth compound is: generating the optical monomer using the ninth compound;

[0038] The structural formula of the optical monomer is: A fifth aspect of the present application provides a method for preparing an optical monomer, comprising the following steps: generating a third compound using a first compound and a second compound;

[0039] 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;

[0040] 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;

[0041] The structural formula of the sixth compound is:

[0042] The structural formula of the seventh compound is:

[0043] generating a ninth compound using the seventh compound and the eighth compound;

[0044] The structural formula of the eighth compound is:

[0045] The structural formula of the ninth compound is:

[0046] generating the optical monomer using the ninth compound;

[0047] The structural formula of the optical monomer is:

[0048] The sixth aspect of the present application provides a composition comprising a solvent, a photoinitiator, a leveling agent, a silane coupling agent and the above-mentioned optical monomer.

[0049] A seventh aspect of the present application provides a resin material, which is obtained by curing the above-mentioned composition.

[0050] The eighth aspect of the present application proposes a method for preparing a resin material, comprising the following steps: providing the above-mentioned composition; forming a mixed liquid after mixing and filtering; coating the mixed liquid on a substrate; and curing the mixed liquid coated on the substrate to obtain the resin material.

[0051] The ninth aspect of the present application proposes an application of the resin material as described above in optical waveguide technology, wherein the resin material is used for an adhesive, a filter, a display material or an anti-ultraviolet film layer.

[0052] As can be seen from the above technical scheme, the optical monomer proposed in this application mainly comprises a hydroquinone group, a benzotriazole group and a phenylene sulfide group, so that the obtained resin material has a high refractive index, as well as good ultraviolet resistance and heat resistance. Among them, the benzotriazole group cooperates with the hydroquinone group 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 ultraviolet resistance. In addition, the optical monomer contains a phenylene sulfide group, which can give the material good high temperature resistance. 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, because of its own high molar refractive index, so that the optical monomer has a high refractive index. BRIEF DESCRIPTION OF THE DRAWINGS

[0053] 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.

[0054] Figure 1 is one of the general structural formulas of the optical monomer proposed in this application;

[0055] Figure 2 is another general structural formula of the optical monomer proposed in this application;

[0056] Figure 3 is the structural formula of the first optical monomer proposed in this application;

[0057] Figure 4 is the structural formula of the second optical monomer proposed in this application;

[0058] Figure 5 is the structural formula of the third optical monomer proposed in this application;

[0059] Figure 6 is the structural formula of the fourth optical monomer proposed in this application;

[0060] 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;

[0061] 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;

[0062] 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;

[0063] 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;

[0064] Fig.11 is a schematic diagram of the reaction principle of preparing an optical monomer using the ninth compound proposed in the present application;

[0065] Fig.12 It is a schematic diagram of the process of preparing the optical monomer proposed in this application;

[0066] Fig.13 It is a schematic diagram of the process of preparing the resin material proposed in this application. DETAILED DESCRIPTION

[0067] 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.

[0068] 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.

[0069] 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.

[0070] See also Figure 1 and Figure 2 , the embodiment of the present application provides an optical monomer, including: a hydroquinone group; two benzotriazole groups located at the ortho position or meta position of the hydroquinone group, a phenylene sulfide group connected to the benzotriazole group, and a first substituent group located on the phenylene sulfide group. 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 is 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.

[0071] The optical monomer proposed in the embodiment of the present application mainly comprises a hydroquinone group, a benzotriazole group and a phenylene sulfide group, so that the obtained resin material has a high refractive index, as well as good UV resistance and heat resistance. Among them, the benzotriazole group cooperates with the hydroquinone group 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.

[0072] In addition, the optical monomer contains phenyl sulfide groups, which can give the material good high temperature resistance. The hydroxyl group in the optical monomer can form hydrogen bonds with the substrate to improve adhesion. The optical monomer is rich in sulfur elements and benzene ring structures. Due to its own high molar refractive index, the optical monomer has a high refractive index.

[0073] In some embodiments, two benzotriazole groups are symmetrically arranged at the ortho or meta position of the hydroquinone group, and the ortho or meta position of each benzotriazole group is connected with at least one phenyl sulfide group, and the type of the first substituent group on each phenyl sulfide group is the same. Thus, the optical monomer of the embodiment of the present application is formed as a whole, with the hydroquinone group as the center and a roughly symmetrical structure, 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, so as to form more chelate rings in the molecule, and more ultraviolet light energy can be absorbed 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 phenyl sulfide group connected to the benzotriazole group is also increased, which is conducive to improving the refractive index, and more first substituent groups can be set, so that more functional groups can be grafted, and the curing rate and the stress resistance effect of the molecule are increased. The overall structure of the molecule is relatively symmetrical, and the performance of both sides of the molecule is relatively uniform, which increases the stress bearing performance in different directions.

[0074] For example, Figure 1 , Figure 3 and Figure 4 As shown, at least one phenylene sulfide group is connected to the meta position of the benzene ring of each benzotriazole group, thereby making the symmetry of the entire optical monomer stronger.

[0075] For example, Figure 2 , Figure 5 and Figure 6 As shown, at least one phenylene sulfide group is connected to the ortho position of the benzene ring of each benzotriazole group, so that the entire optical monomer has extremely high symmetry.

[0076] 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 terminal phenyl sulfide group. 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.

[0077] See also Figure 1 and Figure 2 In some embodiments, the optical monomer has the following general formula:

[0078] or,

[0079]

[0080] 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.

[0081] R7 and R8 are each independently selected from hydrogen or methyl, wherein R7 and R8 may have the same structure or different structures.

[0082] 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.

[0083] n is a positive integer, 1≤n≤50.

[0084] 43, 44, 45, 46, 47, 48, 49, or 50.

[0085] The optical monomer proposed in the embodiment of the present application mainly comprises a hydroquinone group, a benzotriazole group and a phenylene sulfide group, so that the obtained resin material has a high refractive index, as well as good UV resistance and heat resistance. Among them, the benzotriazole group cooperates with the hydroquinone group 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.

[0086] Among them, the optical monomer of the embodiment of the present application is formed as a whole, with the hydroquinone group as the center and a roughly symmetrical structure, 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 phenyl sulfide group connected to the benzotriazole group is also increased, which is conducive to improving the refractive index, 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.

[0087] In addition, the optical monomer contains phenyl sulfide groups, which can give the material good high temperature resistance. In addition, the hydroxyl groups in the optical monomer can form hydrogen bonds 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.

[0088] As an implementation mode, n may be 1, which can be more convenient in synthesis and reduce production costs while maintaining a high refractive index and good heat resistance and UV resistance.

[0089] 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 comprising a hydroquinone group, a benzotriazole group and a phenylene sulfide group, within the scope of the above general formula.

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

[0091]

[0092] The first optical monomer contains a hydroquinone group, a benzotriazole group and a phenylene sulfide group, so that the obtained resin material has a high refractive index, as well as good UV resistance and heat resistance. In the field of AR glasses display, the refractive index of the resin material obtained by the first optical monomer is greater than 1.7. The high refractive index can effectively improve the light efficiency, reduce the thickness of the lens, reduce the cost and obtain a good wearing experience.

[0093] As an embodiment, the structural formula of the second optical monomer may be:

[0094]

[0095] The second optical monomer contains a hydroquinone group, a benzotriazole group and a phenylene sulfide group, so that the obtained resin material has a high refractive index, as well as good UV resistance and heat resistance. In the field of AR glasses display, the refractive index of the resin material made from the second optical monomer is greater than 1.7. The higher refractive index can effectively improve the light efficiency, reduce the thickness of the lens, reduce the cost and obtain a good wearing experience.

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

[0097]

[0098] Among them, the third optical monomer contains a hydroquinone group, a benzotriazole group and a phenylene sulfide group, so that the obtained resin material has a high refractive index, as well as good UV resistance and heat resistance. In the field of AR glasses display, the refractive index of the resin material made by the third optical monomer is greater than 1.7. The higher refractive index can effectively improve the light efficiency, reduce the thickness of the lens, reduce the cost and obtain a good wearing experience.

[0099] As an implementation manner, the structural formula of the fourth optical monomer may be:

[0100]

[0101] Among them, the fourth optical monomer contains a hydroquinone group, a benzotriazole group and a phenylene sulfide group, so that the obtained resin material has a high refractive index, as well as good UV resistance and heat resistance. In the field of AR glasses display, the refractive index of the resin material made by the fourth optical monomer is greater than 1.7. The high refractive index can effectively improve the light efficiency, reduce the thickness of the lens, reduce the cost and obtain a good wearing experience.

[0102] 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 resin material made by the optical monomer of the present application will not be colored, so it is not easy to yellow.

[0103] In the prior art, after organic matter absorbs blue light in the wavelength range of 450nm-490nm and violet light in the wavelength range of 400nm-450nm, the remaining light appears yellow after mixing, 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 obtained resin material will not be colored and is not easy to yellow.

[0104] See also Figures 7 to 12 The present application also provides a method for preparing an optical monomer, comprising the following steps:

[0105] S1, generating a third compound using the first compound and the second compound;

[0106] The structural formula of the first compound is:

[0107] The structural formula of the second compound is:

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

[0109] 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).

[0110] S2, generating a fifth compound using the third compound and the fourth compound;

[0111] The structural formula of the fourth compound is:

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

[0113] 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).

[0114] S3, generating a seventh compound using the fifth compound and the sixth compound;

[0115] The structural formula of the sixth compound is:

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

[0117]

[0118] For example, in step S3, at 0°C, in a nitrogen atmosphere, the sixth compound (35.03g, 143mmol), sodium hydride (3.77g, 157mmol) and anhydrous THF 1000ml (i.e., anhydrous tetrahydrofuran, Tetrahydrofuran) were added, stirred for 1h, the fifth compound (52.36g, 119mmol) was added at 0°C, stirred for 1h, then returned to room temperature and continued to stir for 18h, after the reaction was completed, saturated salt water was added to the system at 0°C to quench the unreacted sodium hydride, 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 (65.07g, 63% yield).

[0119] S4, generating a ninth compound using the seventh compound and the eighth compound;

[0120] The structural formula of the eighth compound is:

[0121] The structural formula of the ninth compound is:

[0122]

[0123] Illustratively, in step S4, the seventh compound (65.07 g, 75 mmol) and the eighth compound (16.2 g, 180 mmol) are reacted in dichloromethane solvent under the action of triethylamine for 13 h to obtain the ninth compound (62.95 g, 86%).

[0124] S5, generating an optical monomer using the ninth compound;

[0125] The structural formula of the optical monomer is:

[0126]

[0127] Illustratively, in step S5, the ninth compound (62.95 g, 64.5 mmol), 540 ml of hydrobromic acid and 420 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 (38.52 g, 63% yield).

[0128] The present application also provides a method for preparing an optical monomer, comprising the following steps:

[0129] S1, generating a third compound using the first compound and the second compound;

[0130] The structural formula of the first compound is:

[0131] The structural formula of the second compound is:

[0132] The structural formula of the third compound is:

[0133] 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).

[0134] S2, generating a fifth compound using the third compound and the fourth compound;

[0135] The structural formula of the fourth compound is:

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

[0137] 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).

[0138] S3, generating a seventh compound using the fifth compound and the sixth compound;

[0139] The structural formula of the sixth compound is:

[0140] The structural formula of the seventh compound is:

[0141]

[0142] For example, in step S3, at 0°C, in a nitrogen atmosphere, the sixth compound (35.03g, 143mmol), sodium hydride (3.77g, 157mmol) and anhydrous THF 1000ml (i.e., anhydrous tetrahydrofuran, Tetrahydrofuran) were added, stirred for 1h, the fifth compound (52.36g, 119mmol) was added at 0°C, stirred for 1h, then returned to room temperature and continued to stir for 18h, after the reaction was completed, saturated salt water was added to the system at 0°C to quench the unreacted sodium hydride, 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 (65.07g, 63% yield).

[0143] S4, generating a ninth compound using the seventh compound and the eighth compound;

[0144] The structural formula of the eighth compound is:

[0145] The structural formula of the ninth compound is:

[0146]

[0147] Illustratively, in step S4, the seventh compound (65.07 g, 75 mmol) and the eighth compound (16.2 g, 180 mmol) are reacted in dichloromethane solvent under the action of triethylamine for 13 h to obtain the ninth compound (62.95 g, 86%).

[0148] S5, generating an optical monomer using the ninth compound;

[0149] The structural formula of the optical monomer is:

[0150]

[0151] Illustratively, in step S5, the ninth compound (62.95 g, 64.5 mmol), 540 ml of hydrobromic acid and 420 ml of acetic acid were added to the reaction bottle, and the mixture was boiled and refluxed for 28 h to obtain the second optical monomer (38.52 g, 63% yield).

[0152] The present application also provides a method for preparing an optical monomer, comprising the following steps:

[0153] S1, generating a third compound using the first compound and the second compound;

[0154] The structural formula of the first compound is:

[0155] The structural formula of the second compound is:

[0156] The structural formula of the third compound is:

[0157] 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).

[0158] S2, generating a fifth compound using the third compound and the fourth compound;

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

[0160] The structural formula of the fifth compound is:

[0161] 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).

[0162] S3, generating a seventh compound using the fifth compound and the sixth compound;

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

[0164] The structural formula of the seventh compound is:

[0165] For example, in step S3, at 0°C, in a nitrogen atmosphere, the sixth compound (35.03g, 143mmol), sodium hydride (3.77g, 157mmol) and anhydrous THF 1000ml (i.e., anhydrous tetrahydrofuran, Tetrahydrofuran) were added, stirred for 1h, the fifth compound (52.36g, 119mmol) was added at 0°C, stirred for 1h, then returned to room temperature and continued to stir for 18h, after the reaction was completed, saturated salt water was added to the system at 0°C to quench the unreacted sodium hydride, 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 (65.07g, 63% yield).

[0166] S4, generating a ninth compound using the seventh compound and the eighth compound;

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

[0168] The structural formula of the ninth compound is:

[0169] Illustratively, in step S4, the seventh compound (65.07 g, 75 mmol) and the eighth compound (16.2 g, 180 mmol) are reacted in dichloromethane solvent under the action of triethylamine for 13 h to obtain the ninth compound (62.95 g, 86%).

[0170] S5, generating an optical monomer using the ninth compound;

[0171] The structural formula of the optical monomer is:

[0172] Illustratively, in step S5, the ninth compound (62.95 g, 64.5 mmol), 540 ml of hydrobromic acid and 420 ml of acetic acid were added to the reaction bottle, and the mixture was boiled and refluxed for 28 h to obtain the third optical monomer (38.52 g, 63% yield).

[0173] The present application also provides a method for preparing an optical monomer, comprising the following steps:

[0174] S1, generating a third compound using the first compound and the second compound;

[0175] The structural formula of the first compound is:

[0176] The structural formula of the second compound is:

[0177] The structural formula of the third compound is:

[0178] 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).

[0179] S2, generating a fifth compound using the third compound and the fourth compound;

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

[0181] The structural formula of the fifth compound is:

[0182] 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).

[0183] S3, generating a seventh compound using the fifth compound and the sixth compound;

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

[0185] The structural formula of the seventh compound is:

[0186] For example, in step S3, at 0°C, in a nitrogen atmosphere, the sixth compound (35.03g, 143mmol), sodium hydride (3.77g, 157mmol) and anhydrous THF 1000ml (i.e., anhydrous tetrahydrofuran, Tetrahydrofuran) were added, stirred for 1h, the fifth compound (52.36g, 119mmol) was added at 0°C, stirred for 1h, then returned to room temperature and continued to stir for 18h, after the reaction was completed, saturated salt water was added to the system at 0°C to quench the unreacted sodium hydride, 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 (65.07g, 63% yield).

[0187] S4, generating a ninth compound using the seventh compound and the eighth compound;

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

[0189] The structural formula of the ninth compound is:

[0190] Illustratively, in step S4, the seventh compound (65.07 g, 75 mmol) and the eighth compound (16.2 g, 180 mmol) are reacted in dichloromethane solvent under the action of triethylamine for 13 h to obtain the ninth compound (62.95 g, 86% yield).

[0191] S5, generating an optical monomer using the ninth compound;

[0192] The structural formula of the optical monomer is:

[0193] Illustratively, in step S5, the ninth compound (62.95 g, 64.5 mmol), 540 ml of hydrobromic acid and 420 ml of acetic acid were added to the reaction bottle, and the mixture was boiled and refluxed for 28 h to obtain the fourth optical monomer (38.52 g, 63% yield).

[0194] The present application also provides a composition, which includes a solvent, a photoinitiator, a leveling agent, a silane coupling agent and the above optical monomer. Thus, a resin material with a high refractive index and good UV resistance and heat resistance can be prepared by using the composition with the above optical monomer.

[0195] In an optional embodiment, the composition may include the following components in weight percentage: solvent 10%-80%; photoinitiator 0.1%-10%; leveling agent 0.1%-5%; silane coupling agent 0.1%-5%; optical monomer 10%-80%.

[0196] 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; and 80% optical monomer.

[0197] In an optional embodiment, the composition may include the following components in weight percentage: 80% solvent; 5% photoinitiator; 3% leveling agent; 2% silane coupling agent; and 10% optical monomer.

[0198] 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; and 49% optical monomer.

[0199] 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; and 49% optical monomer.

[0200] 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; and 49% optical monomer.

[0201] In an optional embodiment, the composition may include the following components in weight percentage: 50% solvent; 0.3% photoinitiator; 0.3% leveling agent; 0.4% silane coupling agent; and 49% optical monomer.

[0202] 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; and 40% optical monomer.

[0203] In an optional embodiment, the composition may include the following components by weight: 10 g of solvent; 10 g of optical monomer; 0.3 g of photoinitiator; 0.03 g of leveling agent; and 0.05 g of silane coupling agent.

[0204] 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.

[0205] In an optional embodiment, the absorption wavelength of the photoinitiator is 368nm-420nm, so that the photoinitiator can start the polymerization reaction under light conditions without affecting the overall light transmittance of the resin material.

[0206] 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.

[0207] 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.

[0208] 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.

[0209] 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 resin materials.

[0210] Among them, KH550, also known as γ-aminopropyltriethoxysilane, can enhance the adhesion of resin materials and improve the mechanical, water-resistant and anti-aging properties of products.

[0211] Among them, KH560, also known as γ-glycidyloxypropyltrimethoxysilane, can improve the strength properties of resin materials.

[0212] The present application also provides a resin material, which is obtained by curing the above composition. Since the resin material is made from the above composition, and the composition includes the above optical monomer, the resin material provided in the present application has a high refractive index, and good UV resistance and heat resistance.

[0213] See also Fig.13 The present application also provides a method for preparing a resin material, comprising the following steps:

[0214] S10, providing the above composition, that is, placing the solvent, the photoinitiator, the leveling agent, the silane coupling agent and the optical monomer in a reaction container.

[0215] S20, forming a mixed solution after mixing and filtering.

[0216] S30, coating the mixed solution on the substrate.

[0217] S40, curing the mixed liquid coated on the substrate to obtain a resin material.

[0218] In the preparation method of the resin material of the embodiment of the present application, the selection of the solvent, the photoinitiator, the leveling agent and the silane coupling agent 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.

[0219] Among them, the optical monomer mainly contains hydroquinone group, benzotriazole group and phenylene sulfide group, so that the obtained resin material has a high refractive index, as well as good UV resistance and heat resistance. The photoinitiator is used to start the polymerization reaction under light conditions, and the leveling agent can help the mixed liquid to spread evenly on the substrate, reducing bubbles and surface defects. The silane coupling agent can enhance the adhesion between materials to improve the overall performance of the obtained resin material.

[0220] In an optional embodiment, in step S30, coating the mixed solution on the substrate includes: coating the mixed solution 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.

[0221] In an optional embodiment, in step S20, the mixture may be vigorously mixed for 2 hours under light-proof conditions, and then filtered using a 0.45 um syringe filter to obtain a mixed solution.

[0222] In an optional embodiment, in step S30, the mixed solution can be coated on a 4-inch wafer, with a coating speed of 3000 rpm and a coating time of 60 seconds. 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 seconds to coat the mixed solution on the wafer to obtain a better film thickness and uniformity.

[0223] In an optional embodiment, in step S40, ultraviolet light curing (365 nm) may be performed under oxygen-free conditions to obtain a resin film with a high refractive index.

[0224] The embodiments of the present application also provide an application of a resin material in optical waveguide technology, wherein the resin material is used for an adhesive, a filter, a display material or an anti-ultraviolet film layer. For example, when the resin material is used for an adhesive, after coating, the light curing has a strong adhesiveness and adhesion, thereby producing a good adhesion with the substrate. When the resin material is used as a filter, it can absorb a certain amount of ultraviolet light after curing to prevent ultraviolet light from passing through. When the resin material is used as a display material, it has a large light transmittance and can be attached to a display screen without affecting the transmission of light. When the resin material is used for an anti-ultraviolet film layer, it can achieve a greater absorption of ultraviolet light, effectively prevent ultraviolet light from passing through, and is not easy to yellow.

[0225] For example, when resin materials are used in the field of AR glasses display, the optical waveguide technology based on the diffraction principle uses resin materials as a substrate, and realizes the coupling, total reflection propagation and coupling out of light through a grating with a specific structure, thereby transmitting the light signal emitted by the image source to the human eye to form a virtual image. In the field of AR glasses display, resin materials with a high refractive index can effectively improve light efficiency, reduce lens thickness, reduce costs and obtain a good wearing experience.

[0226] The optical monomer and resin material of the present application are further described below in combination with specific embodiments and test data.

[0227] Example 1

[0228] Propylene glycol methyl ether acetate (10 g), the first optical monomer (10 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, and the mixture was mixed vigorously for 2 h under light-proof conditions, and then filtered using a 0.45 um syringe filter to obtain a high-refractive resin mixed solution. The mixed solution was subjected to a coating treatment on a 4-inch glass wafer (rotation speed 3500, time 60 s), and UV curing (365 nm) was performed under anaerobic conditions to obtain a high-refractive resin film.

[0229] Example 2

[0230] Propylene glycol methyl ether acetate (10 g), the second optical monomer (10 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 in a dark environment, and then filtered with a 0.45 um syringe filter to obtain a high-refractive resin mixture. The mixture was coated on a 4-inch glass wafer (rotation speed 3500, time 60 s), and UV-cured (365 nm) under anaerobic conditions to obtain a high-refractive resin film.

[0231] Example 3

[0232] Propylene glycol methyl ether acetate (10 g), the third optical monomer (10 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, and mixed vigorously for 2 h under light-proof conditions, and then filtered using a 0.45 um syringe filter to obtain a high-refractive resin mixed solution. The mixed solution was subjected to a coating treatment on a 4-inch glass wafer (rotation speed 3500, time 60 s), and UV curing (365 nm) was performed under anaerobic conditions to obtain a high-refractive resin film.

[0233] Example 4

[0234] Propylene glycol methyl ether acetate (10 g), the fourth optical monomer (10 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, and mixed vigorously for 2 h under light-proof conditions, and then filtered using a 0.45 um syringe filter to obtain a high-refractive resin mixed solution. The mixed solution was subjected to a 4-inch glass wafer for a uniform coating (rotation speed 3500, time 60 s), and UV curing (365 nm) was performed under anaerobic conditions to obtain a high-refractive resin film.

[0235] Comparative Example 1

[0236] The diluent monomer o-phenylphenoxyethyl acrylate (OPPEA) purchased from Sartomer was used to replace the optical monomer, and the other preparation processes remained unchanged.

[0237] Propylene glycol methyl ether acetate (10 g), OPPEA (10 g), 2,4,6-trimethylbenzoyl-diphenylphosphine oxide (0.3 g), BYK370 (0.03 g), KH570 (0.05 g) were added to a 50 mL volumetric flask, mixed vigorously for 2 h in a dark environment, and then filtered with a 0.45 um syringe filter to obtain a high-refractive resin mixture. The mixture was coated on a 4-inch glass wafer (rotation speed 3500, time 60 s), and UV-cured (365 nm) under anaerobic conditions to obtain a high-refractive resin film.

[0238] Comparative Example 2

[0239] The optical monomer was replaced by the diluent monomer ETERMER 2206 (bifunctional acrylate) purchased from Changxing Chemical, and the other preparation processes remained unchanged.

[0240] Propylene glycol methyl ether acetate (10 g), ETERMER 2206 (10 g), 2,4,6-trimethylbenzoyl-diphenylphosphine oxide (0.3 g), BYK370 (0.03 g), KH570 (0.05 g) were added to a 50 mL volumetric flask, mixed vigorously for 2 h in a dark environment, and then filtered with a 0.45 um syringe filter to obtain a high-refractive resin mixture. The mixture was coated on a 4-inch glass wafer (rotation speed 3500, time 60 s), and UV-cured (365 nm) under anaerobic conditions to obtain a high-refractive resin film.

[0241] Comparative Example 3

[0242] The diluent monomer 9,9-bis[4-(2-acryloyloxyethoxy)phenyl]fluorene purchased from Tokyo Chemical Industry Co., Ltd. (TCI for short) was used to replace the optical monomer, and the other preparation processes remained unchanged.

[0243] Propylene glycol methyl ether acetate (10 g), 9,9-bis[4-(2-acryloyloxyethoxy)phenyl]fluorene (10 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 in a dark environment, and then filtered with a 0.45 um syringe filter to obtain a high-refractive resin mixture. The mixture was coated on a 4-inch glass wafer (rotation speed 3500, time 60 s), and UV-cured (365 nm) under anaerobic conditions to obtain a high-refractive resin film.

[0244] The high-fold resin films 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.

[0245] Among them, the performance test methods and standards are as follows:

[0246] (1) Refractive index: tested using an ellipsometer (ME-L Mueller Matrix Spectroscopic Ellipsometer, Yiguang Technology);

[0247] (2) Light transmittance: high-precision haze meter (HM-150, Murakami Color MCRL);

[0248] (3) Yellowness: high-precision haze meter (HM-150, Murakami Color MCRL);

[0249] (4) Haze: high-precision haze meter (HM-150, Murakami Color MCRL);

[0250] (5) Adhesion: 100-grid test;

[0251] (6) UV aging: UV aging test box (light source power 650mw, irradiation 4h, stop 4h as one cycle, a total of 24 cycles);

[0252] (7) Xenon lamp aging: Xenon lamp aging test chamber (Q-SUN Xe-1, Q-LAB);

[0253] (8) Thermal stability (Tg): measured using a differential scanning calorimeter (DSC3 Mettler) at a heating rate of 5°C / min.

[0254] Table 1

[0255]

[0256] It can be seen from Examples 1-4 and Comparative Examples 1-3 in Table 1 that the high-refractive index resin films prepared in Examples 1 to 4 of the present application have a significantly higher refractive index than the high-refractive index resin films prepared in Comparative Examples 1 to 3. This is because the molecules of the optical monomers in Examples 1 to 4 of the present application contain benzene rings and long-chain sulfanes, and these two groups have very high molar refractive indices, so their molecular refractive indices are high.

[0257] The high-refractive resin films prepared in Examples 1 to 4 of the present application have significantly higher UV resistance than the high-refractive resin films prepared in Comparative Examples 1 to 3. This is because the benzotriazole groups in the molecules of the optical monomers in Examples 1 to 4 of the present application have good UV resistance, and the principle is that nitrogen and hydroxyl groups in the molecules can form intrinsic hydrogen bonds to form chelate rings. After absorbing ultraviolet light, the molecules undergo thermal vibrations, the internal hydrogen bonds break, the chelate rings open, and the ultraviolet energy is converted into heat energy and released.

[0258] The high-refractive resin films prepared in Examples 1 to 4 of the present application have significantly higher adhesion than the high-refractive resin films prepared in Comparative Examples 1 to 3. This is because the molecules of the optical monomers in Examples 1 to 4 of the present application contain hydroxyl structures, which can form hydrogen bonds with the substrate, thereby achieving chemical riveting.

[0259] The high-refractive resin films prepared in Examples 1 to 4 of the present application have significantly higher heat resistance than the high-refractive resin films prepared in Comparative Examples 1 to 3. This is because there are a large number of benzene ring structures in the molecules of the optical monomers in Examples 1 to 4 of the present application, and their unique P-π large conjugated structures give the molecules high heat resistance.

[0260] Therefore, the optical monomer of the embodiment of the present application, through the hydroquinone group, benzotriazole group and phenylene sulfide group in its molecule, makes the prepared resin material have a high refractive index and good ultraviolet resistance and heat resistance.

[0261] 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.

[0262] The above description is only a specific implementation mode 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 substitutions within the technical scope disclosed in the present application, and these modifications or substitutions should be included in the protection scope of the present application.

[0263] 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: hydroquinone group; Two benzotriazole groups located at the ortho position or the meta position of the hydroquinone group, a phenylene sulfide group connected to the benzotriazole group, and a first substituent group located on the phenylene sulfide group.

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 phenylene sulfide group is connected to the ortho or meta position of each benzotriazole group, and the first substituent group on each phenylene sulfide group 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 one of hydrogen, substituted or unsubstituted C1-20 alkylene, substituted or unsubstituted C1-30 alkylene ether, substituted or unsubstituted C6-30 arylene, and substituted or unsubstituted C7-30 aralkylene; R7 and R8 are each independently selected from hydrogen or methyl; R9 and R10 are each independently selected from one of hydrogen, substituted or unsubstituted C1-20 alkyl, substituted or unsubstituted C1-30 alkyl ether, substituted or unsubstituted C6-30 aryl, substituted or unsubstituted C7-30 aralkyl and fluoroalkyl; 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. 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:

9. A method for preparing an optical monomer, characterized in that: The method comprises the following steps: generating a third compound by using a first compound and a 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 composition, characterized in that The composition comprises a solvent, a photoinitiator, a leveling agent, a silane coupling agent and the optical monomer according to any one of claims 1 to 6.

12. The composition according to claim 11, characterized in that The composition includes the following components in weight percentage: Solvent 10%-80%; Photoinitiator 0.1%-10%; Leveling agent 0.1%-5%; Silane coupling agent 0.1%-5%; 10%-80% of the optical monomer according to any one of claims 1 to 6.

13. The composition according to claim 11, 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.

14. A resin material, characterized in that: The resin material is obtained by curing the composition according to any one of claims 11 to 13.

15. A method for preparing a resin material, characterized in that: The steps include: Providing a composition as claimed in any one of claims 11 to 13; After mixing and filtering, a mixed liquid is formed; coating the mixed solution on a substrate; The mixed liquid coated on the substrate is cured to obtain the resin material.

16. The preparation method according to claim 15, characterized in that: The step of coating the mixed solution on the substrate includes: coating the mixed solution on the wafer for coating, the coating speed is 1000rpm-10000rpm, and the coating time is 10s-300s.

17. An application of the resin material according to claim 14 in optical waveguide technology, characterized in that: The resin material is used for adhesive, filter, display material or anti-ultraviolet film layer.

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