High-refractive-index thioester compounds, optical resins, their preparation methods and applications

Abstract

This application discloses a high-refractive-index thioester compound, an optical resin, its preparation method, and its applications. The general chemical structure of the thioester compound is shown in formula (Ⅰ): where n is zero or a positive integer; R is at least one of H atoms, substituted or unsubstituted alkyl groups, and substituted or unsubstituted aryl groups. The thioester compound provided in this application introduces sulfur atoms with an adjustable atomic number, which can improve the refractive index of the optical resin. Furthermore, the synthesis method of the optical resin is simple, easy to implement, and inexpensive.

Description

Technical Field

[0001] This application relates to the field of optical materials technology, and in particular to a high-refractive-index thioester compound, an optical resin, a method for preparing the same, and its applications. Background Technology

[0002] Organic resins, as an important component of optical resins, possess characteristics such as light weight, impact resistance, ease of molding and processing, and excellent optical properties. Therefore, they are gradually replacing traditional optical materials and are widely used in materials such as optical fibers, building materials, resin lenses, precision lenses, and anti-reflective coatings. Traditional optical resins, such as polymethyl methacrylate (PMMA), have a refractive index n... D =1.492; Polycarbonate (PC), refractive index n D =1.584; Polystyrene (PS), refractive index n D =1.592, etc., although applicable to most optical fields, are increasingly unable to meet people's requirements for high precision and high performance of optical components.

[0003] However, current optical resins still suffer from drawbacks such as expensive raw materials and complex manufacturing methods. Therefore, researching and developing new optical resins, especially those with high refractive indices, is currently a major research direction in the field of optical materials. Summary of the Invention

[0004] In view of this, in order to solve at least one of the above problems, this application provides a high refractive index sulfide compound, which is simple to prepare and uses inexpensive raw materials.

[0005] Furthermore, this application also provides an optical resin, a method for preparing the same, and applications of the optical resin. The aforementioned thioester compound can be directly cured to prepare an optical resin with a high refractive index; the preparation method is simple and low-cost.

[0006] This application provides a high-refractive-index thioester compound, the general chemical structure of which is shown in formula (Ⅰ):

[0007]

[0008] Where n is zero or a positive integer;

[0009] R is at least one of H atom, substituted or unsubstituted alkyl group, and substituted or unsubstituted aryl group.

[0010] In some possible embodiments, R in formula (Ⅰ) is a methyl group.

[0011] In some possible embodiments, the thioester compound is any one of the following compounds D-1, D-2, D-3, and D-4:

[0012]

[0013] as well as

[0014] This application also provides an optical resin, which is obtained by cross-linking and curing a high-refractive-index thioester compound as described above. The curing is photocuring.

[0015] This application also provides a method for preparing an optical resin, comprising:

[0016] A thiol compound is subjected to an acrylation reaction to obtain a thioester compound; wherein the general chemical structure of the thioester compound is shown in formula (I):

[0017] Wherein, n is zero or a positive integer; R is at least one of H atom, substituted or unsubstituted alkyl group, and substituted or unsubstituted aryl group;

[0018] The general chemical structural formula of the thiol compound is shown in formula (II):

[0019] Where n is zero or a positive integer; and

[0020] The thioester compound is mixed with a crosslinking agent and an initiator, and then crosslinked and cured to obtain the optical resin.

[0021] In some possible embodiments, the method for preparing the thiol compound includes:

[0022] Step 1: Protect mercaptoethanol with triphenylmethanol to obtain the first intermediate;

[0023] Step 2: The first intermediate is oxidized with pyridine chlorochromate to obtain the second intermediate;

[0024] Step 3: Protect the aldehyde group of the second intermediate with ethylenedithiol to obtain the third intermediate;

[0025] Step 4: Triethylsilane is used to remove the triphenylmethyl group under acidic conditions to obtain a fourth intermediate, wherein the fourth intermediate is the thiol compound in formula (II) when n=0;

[0026] Step 5: Replace bromoethanol with the fourth intermediate to obtain the fifth intermediate;

[0027] Step 6: The fifth intermediate is synthesized into a thiourea salt using hydrobromic acid and thiourea, and then hydrolyzed under alkaline conditions to obtain the sixth intermediate, which is the thiol compound when n=1 in formula (II);

[0028] Repeating steps 5 and 6 will yield the thiol compound when n ≥ 2 in formula (II).

[0029] In some possible embodiments, the crosslinking agent includes at least one of bis(4-methacryloylthiophenyl) sulfide, ethylene glycol dimethacrylate, dicyclopentenyl acrylate, and ethoxylated bisphenol A dimethacrylate;

[0030] The initiator is a photoinitiator, and the curing is ultraviolet light curing.

[0031] In some possible embodiments, the preparation of the thioester compound includes:

[0032] Add the thiol compound, tetrahydrofuran, and triethylamine shown to a three-necked flask equipped with a constant-pressure dropping funnel, and then introduce nitrogen gas and stir to obtain a mixture.

[0033] The mixture was cooled to zero degrees Celsius, acryloyl chloride or methacryloyl chloride was added and mixed, and the mixture was stirred overnight at room temperature to obtain a reaction mixture; and

[0034] The reaction mixture was subjected to vacuum distillation to remove volatiles, and then purified by column chromatography to obtain the thioester compound.

[0035] In some possible embodiments, zirconium oxide nanoparticles are also added during the step of mixing the thioester compound with the crosslinking agent and the initiator.

[0036] In some possible embodiments, the present application also provides the use of the optical resin as described above or the optical resin prepared by the method described above.

[0037] Compared to existing technologies, the thioester compounds provided in this application introduce sulfur atoms into the polymer chain. Since sulfur atoms possess both a high molar refractive index and low dispersion, exhibit good environmental stability, are non-toxic, and have a wide adjustable refractive index range, they can improve the refractive index of the optical resin formed by curing the thioester compound. Furthermore, the higher the sulfur content in the polymer chain of the optical resin, the higher the refractive index. The amount of sulfur atoms in the thioester compound can be controlled according to actual needs. The preparation of the optical resin, starting from thiol compounds and introducing sulfur into the molecular chain of the thioester compound, is a simple and easy-to-implement synthesis method with inexpensive raw materials, which helps reduce costs. Moreover, the synthesized thioester compound can be further cross-linked and cured to form an optical resin. Detailed Implementation

[0038] The present application is further illustrated below with reference to embodiments. These embodiments are for illustrative purposes only and are not intended to limit the scope of the application. Experimental methods in the following embodiments that do not specify specific conditions are generally performed under conventional conditions in the art or as recommended by the manufacturer; the raw materials and reagents used, unless otherwise specified, are all commercially available from the conventional market. Any non-substantial changes and substitutions made by those skilled in the art based on this application are within the scope of protection claimed in this application.

[0039] This application provides a thiol compound with the general chemical structure shown in formula (II):

[0040] Where n is zero or a positive integer.

[0041] In this application, sulfur is introduced into the polymer chain primarily using thiol compounds as raw materials. Furthermore, the higher the sulfur content in the final polymer chain, the higher the refractive index. The thiol compounds provided in this application possess a unique dithiopentane ring and long-chain structure, with a high sulfur content. Using these thiol compounds, thioester compounds (i.e., thioacrylate monomers) with high refractive indices can be prepared. The preparation method is simple, and the raw materials are inexpensive, which helps reduce costs. Additionally, by using this thioester compound as a monomer, along with a crosslinking agent and a photoinitiator, and curing it under ultraviolet light, optical resins with high refractive indices can be prepared.

[0042] This application also provides a method for preparing the above-mentioned thiol compound, comprising the following steps:

[0043] Step 1: Protect mercaptoethanol with triphenylmethanol (TrtOH) to obtain the first intermediate M1.

[0044] Step 2: Oxidize the first intermediate M1 with pyridinium chlorochromate (PCC) to obtain the second intermediate M2.

[0045] Step 3: Protect the aldehyde group of the second intermediate M2 with ethylenedithiol to obtain the third intermediate M3.

[0046] Step 4: Remove the triphenylmethyl group of the second intermediate M2 using triethylsilane (Et3SiH) and trifluoroacetic acid (TFA) under acidic conditions to obtain the fourth intermediate M4 (i.e., the thiol compound obtained when n is 0 in formula (II)).

[0047] Step 5: Replace bromoethanol with the fourth intermediate M4 to obtain the fifth intermediate M5.

[0048] Step 6: The fifth intermediate M5 is synthesized into a thiourea salt using hydrobromic acid and thiourea, and then hydrolyzed under alkaline conditions to obtain the sixth intermediate M6 (i.e., the thiol compound obtained when n is 1 in formula (II)).

[0049] Repeating steps five and six will yield thiols with n ≥ 2 in formula (II).

[0050] The specific reaction process is as follows:

[0051]

[0052] An embodiment of this application also provides a thioacrylate monomer, the general chemical formula of which is shown in formula (I):

[0053] Wherein, n is zero or a positive integer; R is at least one of H atom, substituted or unsubstituted alkyl group, and substituted or unsubstituted aryl group.

[0054] Specifically, the thioacrylate monomer can be one of the following D-1, D-2, D-3, and D-4 compounds:

[0055]

[0056] An embodiment of this application also provides a method for preparing the above-mentioned thioacrylate monomer (i.e., thioacrylate compound), comprising the following steps:

[0057] Step 1: Add tetrahydrofuran, triethylamine and thiol compound as shown in formula (I) to a 500mL three-necked flask equipped with a constant pressure dropping funnel, and stir with nitrogen gas for 10 minutes.

[0058] Step 2: Cool the clarified liquid to 0°C, add acryloyl chloride or methacryloyl chloride and mix, stirring overnight at room temperature.

[0059] Step 3: The mixture after the reaction was then removed by vacuum distillation to remove volatiles, and purified by column chromatography to obtain the thioacrylate monomer.

[0060] This application also provides a method for preparing an optical resin, comprising the following steps:

[0061] The thioacrylate monomer is mixed with a crosslinking agent and a photoinitiator, and cured under ultraviolet light to obtain the optical resin. For example, the optical resin may have the following crosslinking structure:

[0062]

[0063] The crosslinking agent can be at least one of bis(4-methacryloylthiophenyl) sulfide, ethylene glycol dimethacrylate, dicyclopentenyl acrylate, and ethoxylated bisphenol A dimethacrylate.

[0064] This application also provides the application of the optical resin prepared by the aforementioned method, which can be widely used in scenarios requiring high refractive index, such as photoresist, holographic storage, and electronic packaging materials.

[0065] The thioester compounds provided in this application introduce sulfur atoms into the polymer chain. Since sulfur atoms possess both a high molar refractive index and low dispersion, exhibit good environmental stability, are non-toxic, and have a wide adjustable refractive index range, they can improve the refractive index of the optical resin formed by curing the thioester compounds. Furthermore, the higher the sulfur content in the polymer chain of the optical resin, the higher the refractive index. The amount of sulfur atoms in the thioester compounds can be controlled according to actual needs. The preparation of the optical resin starts with thiol compounds, introducing sulfur into the molecular chain of the thioester compounds. The synthesis method is simple, easy to implement, and the raw materials are readily available and inexpensive, which helps reduce the cost of the optical resin. Moreover, the synthesized thioester compounds can be further cross-linked and cured to form optical resins. This optical fiber resin has a high refractive index (greater than or equal to 1.651) and a high Abbe number (greater than or equal to 34).

[0066] The following specific embodiments illustrate the preparation method and performance of the optical resin provided in this application. Those skilled in the art will understand that the following examples are for illustrative purposes only and should not be construed as limiting the invention. Unless otherwise stated, reagents, software, and instruments mentioned below are all conventional commercially available products or open-source materials.

[0067] Example 1

[0068] This embodiment provides a method for preparing thioacrylate monomer D-1, the chemical structural formula of which is as follows:

[0069]

[0070] The preparation method specifically includes the following steps:

[0071] Step 1: In a 3L two-necked flask equipped with a constant-pressure dropping funnel, add 100g of 2-mercaptoethanol, 1L of dichloromethane, and 350.0g of triphenylmethanol. Cool to 0°C, and add 98.0mL of trifluoroacetic acid dropwise. After the addition is complete, allow the mixture to rise to room temperature and react overnight. Quench the reaction with water, and wash successively with deionized water, saturated sodium bicarbonate, and saturated brine. Dry the organic phase with anhydrous sodium sulfate, filter, and remove the solvent by rotary evaporation of the filtrate to obtain the crude product. Recrystallize the crude product from n-hexane to obtain 384.1g of pure intermediate M1.

[0072] Step 2: Take a 5L flask, add 350g of the first intermediate M1, add 2L of dichloromethane, cool to 0℃, add 350g of PCC, and react at room temperature for 1 hour. Add silica gel and stir until the system becomes a paste, filter, wash with dichloromethane, evaporate the filtrate to dryness, and obtain 245g of pure second intermediate M2 by column chromatography.

[0073] Step 3: Take a 3L flask, add 210g of the second intermediate M2, 1.5L of anhydrous dichloromethane and 61.8g of ethylenedithiol, cool to 0℃, and slowly add 144g of boron trifluoride diethyl ether dropwise. After the addition is complete, raise to room temperature and stir for 1 hour. Thin-layer chromatography (TLC) is used to determine if the reaction of the starting material is complete. Quench the reaction with water, separate the liquids, wash the organic phase with saturated brine, dry with anhydrous sodium sulfate, filter, and evaporate the filtrate to dryness to obtain the crude product. Purify by column chromatography to obtain 47.2g of pure third intermediate M32.

[0074] Step 4: Take a 3L flask, add 240g of the third intermediate M3, 1.5L of dichloromethane and 212g of triethylsilane, cool to 0℃, add 552g of trifluoroacetic acid, and react at room temperature for 2 hours. TLC detection showed the reaction was complete. The reaction was quenched with deionized water, separated, and the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was evaporated to dryness to obtain the crude product. Vacuum distillation under reduced pressure yielded 70.4g of the pure fourth intermediate M4. The fourth intermediate M4 is the thiol compound at n=0.

[0075] Step 5: Take a 500mL flask, add 10.0g of the fourth intermediate M4, add 200mL of anhydrous dichloromethane, add 10.0g of triethylamine, cool to 0℃, and slowly add 7.5g of methacryloyl chloride dropwise. After the addition is complete, raise the temperature to room temperature and react for 1h. Add deionized water to quench the reaction, separate the liquid and liquid phases, wash the organic phase with saturated brine, dry it with anhydrous sodium sulfate, filter, and evaporate the filtrate to dryness to obtain the crude product. Distill under reduced pressure to obtain 8.8g of pure thioacrylate monomer D-1.

[0076] Example 2

[0077] This embodiment provides a method for preparing the thioacrylate monomer D-2, the chemical structural formula of which is as follows:

[0078]

[0079] The preparation method specifically includes the following steps:

[0080] Step 1: Take a 500mL flask, add 20g of the fourth intermediate M4, dissolve it in 200mL of 1,4-dioxane, then add 17.0g of bromoethanol and 27g of potassium carbonate, and react at 60℃ for 12h. The reaction was monitored by TLC until complete, and the reaction was quenched with distilled water. Extract three times with ethyl acetate (100mL x 3), combine the organic phases, wash with distilled water, wash with saturated brine, dry with anhydrous sodium sulfate, filter, and evaporate the filtrate to dryness to obtain the crude product. The crude product was purified by column chromatography to obtain 16.5g of pure fifth intermediate M5.

[0081] Step 2: Take a 100mL flask, add 6.2g of thiourea and 13.8g of 48% hydrobromic acid, heat to 60℃ and stir. Slowly add 16g of the fifth intermediate M5 dropwise. After the addition is complete, heat to 80℃ and stir for 4 hours. Cool to 50℃, add 23.0g of 25% ammonia water, and react for 2 hours. TLC detection shows that the reaction is complete. Cool to room temperature, add dichloromethane for extraction, wash the organic phase with water and saturated brine, dry with anhydrous sodium sulfate, filter, and evaporate the filtrate to dryness to obtain the crude product. The crude product is purified by column chromatography to obtain 15.6g of pure sixth intermediate M6. The sixth intermediate M6 is the thiol compound when n=1.

[0082] Step 3: Take a 250mL flask, add 5.0g of the sixth intermediate M6, add 60mL of anhydrous dichloromethane, add 3.6g of triethylamine, cool to 0℃, and slowly add 2.7g of methacryloyl chloride dropwise. After the addition is complete, raise the temperature to room temperature and react for 1h. Add deionized water to quench the reaction, separate the liquid and liquid phases, wash the organic phase with saturated brine, dry it with anhydrous sodium sulfate, filter, and evaporate the filtrate to dryness to obtain the crude product. Distill under reduced pressure to obtain 4.2g of pure thioacrylate monomer D-2.

[0083] Example 3

[0084] This embodiment provides a method for preparing the thioacrylate monomer D-3, the chemical structural formula of which is as follows:

[0085]

[0086] The preparation method specifically includes the following steps:

[0087] Step 1: Take a 500mL flask, add 20g of the sixth intermediate M6, dissolve it in 200mL of 1,4-dioxane, then add 17.0g of bromoethanol and 27g of potassium carbonate, and react at 60℃ for 12h. The reaction was monitored by TLC until complete, and the reaction was quenched with distilled water. The mixture was extracted three times with ethyl acetate (100mL x 3), the organic phases were combined, washed with distilled water and saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was evaporated to dryness to obtain the crude product. The crude product was purified by column chromatography to obtain 16.5g of pure seventh intermediate M7.

[0088] Step 2: Take a 100mL flask, add 6.2g of thiourea and 13.8g of 48% hydrobromic acid, and heat to 60℃ with stirring. Slowly add 16g of the seventh intermediate M7 dropwise. After the addition is complete, heat to 80℃ and stir for 4 hours. Cool to 50℃, add 23.0g of 25% ammonia water, and react for 2 hours. TLC detection shows that the reaction is complete. Cool to room temperature, add dichloromethane for extraction, wash the organic phase with water, wash with saturated brine, dry with anhydrous sodium sulfate, filter, and evaporate the filtrate to dryness to obtain the crude product. The crude product is purified by column chromatography to obtain 15.6g of pure eighth intermediate M8.

[0089] Step 3: Take a 100mL flask, add 5.0g of intermediate M8 (step 8), 50mL of anhydrous dichloromethane, and 3.6g of triethylamine. Cool to 0℃, and slowly add 2.7g of methacryloyl chloride dropwise. After the addition is complete, raise the temperature to room temperature and react for 1 hour. Quench the reaction with deionized water, separate the liquids, wash the organic phase with saturated brine, dry it with anhydrous sodium sulfate, filter, and evaporate the filtrate to dryness to obtain the crude product. Distill under reduced pressure to obtain 4.1g of pure thioacrylate monomer D-3.

[0090] Example 4

[0091] This embodiment provides a method for preparing the thioacrylate monomer D-4, the chemical structural formula of which is as follows:

[0092]

[0093] The preparation method specifically includes the following steps:

[0094] Step 1: Take a 500mL flask, add 10g of intermediate M8 (the eighth step), dissolve it in 150mL of 1,4-dioxane, then add 6.2g of bromoethanol and 9.8g of potassium carbonate, and heat to 60℃ for 12h. The reaction was monitored by TLC until complete, and the reaction was quenched with distilled water. Extract three times with ethyl acetate (100mL x 3), combine the organic phases, wash with distilled water, wash with saturated brine, dry over anhydrous sodium sulfate, filter, and evaporate the filtrate to dryness to obtain the crude product. The crude product was purified by column chromatography to obtain 11.1g of pure product M9.

[0095] Step 2: Take a 100mL flask, add 3.0g of thiourea and 6.6g of 48% hydrobromic acid, and heat to 60℃ with stirring. Slowly add 10.0g of the ninth intermediate M9 dropwise. After the addition is complete, heat to 80℃ and stir for 4 hours. Cool to 50℃, add 10.9g of 25% ammonia water, and react for 2 hours. TLC detection shows that the reaction is complete. Cool to room temperature, add dichloromethane for extraction, wash the organic phase with water, wash with saturated brine, dry with anhydrous sodium sulfate, filter, and evaporate the filtrate to dryness to obtain the crude product. The crude product is purified by column chromatography to obtain 7.1g of pure tenth intermediate M10.

[0096] Step 3: Take a 100mL flask, add 5.0g of the tenth intermediate M10, add 50mL of anhydrous dichloromethane, add 2.8g of triethylamine, cool to 0℃, and slowly add 2.1g of methacryloyl chloride dropwise. After the addition is complete, raise the temperature to room temperature and react for 1h. Add deionized water to quench the reaction, separate the liquids, wash the organic phase with saturated brine, dry with anhydrous sodium sulfate, filter, and evaporate the filtrate to dryness to obtain the crude product. Distill under reduced pressure to obtain 3.5g of pure thioacrylate monomer D-4.

[0097] Take 3.0 g each of the thioacrylate monomers D-1, D-2, D-3, and D-4 prepared in Examples 1-4, and add 90 mg of photoinitiator (diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide, abbreviated as TPO), and stir until completely dissolved. Pour each into a 2*1*0.5 cm square acrylic mold, and cure under UV light for 2 minutes at room temperature and a light intensity of 80 W / cm to obtain optical resins. The refractive index of the above thioacrylate monomers before curing and the refractive index and Abbe number of the corresponding optical resins obtained after photocuring are shown in Table 1.

[0098] The properties of the thioacrylate monomers and optical resins in Examples 1-4 are shown in Table 1.

[0099] Table 1

[0100]

[0101] As shown in Table 1, the thioacrylate monomers prepared in Examples 1 to 4 of this application are cured by ultraviolet light to form optical resin blocks. After curing, the refractive index is significantly improved, and the refractive index of the optical resin block is greater than or equal to 1.65, with an Abbe number as high as 37, thus enabling it to have a wide range of applications.

[0102] Finally, it should be noted that the above embodiments are only used to illustrate the technical solutions of this application and are not intended to limit it. Although this application has been described in detail with reference to preferred embodiments, those skilled in the art should understand that modifications or equivalent substitutions can be made to the technical solutions of this application without departing from the spirit and scope of the technical solutions of this application.

Claims

1. A high-refractive-index thioester compound, characterized in that, The thioester compound is any one of the following compounds: D-2, D-3, and D-4: ， as well as .

2. An optical resin, characterized in that, The optical resin is obtained by cross-linking and curing the high refractive index thioester compound as described in claim 1.

3. A method for preparing an optical resin, characterized in that, include: A thiol compound is subjected to an acrylation reaction to yield a thioester compound; wherein the thioester compound has the chemical composition of any one of the following compounds D-2, D-3, and D-4: , as well as ; The general chemical structural formula of the thiol compound is shown in formula (II): (II), where n is a positive integer; and The thioester compound is mixed with a crosslinking agent and an initiator, and then crosslinked and cured to obtain the optical resin.

4. The method for preparing the optical resin as described in claim 3, characterized in that, The method for preparing the thiol compound includes: Step 1: Protect mercaptoethanol with triphenylmethanol to obtain the first intermediate; Step 2: The first intermediate is oxidized with pyridine chlorochromate to obtain the second intermediate; Step 3: Protect the aldehyde group of the second intermediate with ethylenedithiol to obtain the third intermediate; Step 4: Triethylsilane is used to remove the triphenylmethyl group under acidic conditions to obtain a fourth intermediate, wherein the fourth intermediate is the thiol compound in formula (II) when n=0; Step 5: Replace bromoethanol with the fourth intermediate to obtain the fifth intermediate; Step 6: The fifth intermediate is synthesized into a thiourea salt using hydrobromic acid and thiourea, and then hydrolyzed under alkaline conditions to obtain the sixth intermediate, which is the thiol compound when n=1 in formula (II); Repeating steps 5 and 6 will yield the thiol compound when n in formula (II) is a positive integer ≥ 2.

5. The method for preparing the optical resin as described in claim 3, characterized in that, The crosslinking agent includes at least one of bis(4-methacryloylthiophenyl) sulfide, ethylene glycol dimethacrylate, dicyclopentenyl acrylate, and ethoxylated bisphenol A dimethacrylate. The initiator is a photoinitiator, and the curing is ultraviolet light curing.

6. The method for preparing the optical resin according to claim 3, characterized in that, The preparation of the thioester compound includes: The thiol compound, tetrahydrofuran, and triethylamine were added to a three-necked flask equipped with a constant-pressure dropping funnel, and nitrogen gas was introduced and stirred to obtain a mixture. The mixture was cooled to zero degrees Celsius, methacryloyl chloride was added and mixed, and the mixture was stirred overnight at room temperature to obtain a reaction mixture; and The reaction mixture was subjected to vacuum distillation to remove volatiles, and then purified by column chromatography to obtain the thioester compound.

7. The method for preparing the optical resin according to claim 3, characterized in that, In the step of mixing the thioester compound with the crosslinking agent and the initiator, zirconium oxide nanoparticles are also added.

8. The application of an optical resin prepared by a method for preparing an optical resin as described in claim 2 or an optical resin as described in any one of claims 3 to 7 in photoresists, holographic storage and electronic packaging materials.

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