(Methyl) acrylate monomer as well as preparation method and application thereof

Abstract

The invention relates to a (methyl) acrylate monomer as well as a preparation method and application thereof, the structural general formula of the (methyl) acrylate monomer is shown as G1, G2 and G3: # imgabs0 #, r2 and R3 are selected from hydrogen, Br, phenyl, methyl or # imgabs 1 #, wherein A1 in the # imgabs 2 # is phenyl or methyl. According to the (methyl) acrylate monomer provided by the invention, the molecular size of the whole monomer is relatively small, agglomeration is not easy to occur, and the (methyl) acrylate monomer has a high refractive index.

Description

Technical Field

[0001] The invention relates to the technical field of holographic materials, in particular to (meth)acrylate monomers and a preparation method and application thereof. Background Art

[0002] The various components used to make holographic recording media, such as photosensitive dyes, initiators, chain transfer agents, writing monomers, film-forming resins, plasticizers, etc., work together to determine whether the performance of the holographic recording media is good or not.

[0003] Among them, the migration rate and polymerization rate of the writing monomer jointly determine the speed of grating formation. The migration rate of the writing monomer is faster than the polymerization rate to obtain a grating with a stable refractive index modulation. After the writing monomer located in the coherent bright area is polymerized, the unreacted writing monomer located in the coherent dark area quickly migrates to the coherent bright area, and squeezes the film-forming resin in the bright area into the coherent dark area, so that the refractive index of the bright area is close to the refractive index of the writing monomer, and the refractive index of the dark area is close to the refractive index of the film-forming resin. At the same time, the writing monomer and the film-forming resin have a refractive index difference to form a refractive index modulated volume holographic grating. The greater the refractive index difference between the writing monomer and the film-forming resin, the faster the holographic recording medium can form a refractive index modulated volume holographic grating. In the existing refractive index modulated phase-type volume holographic grating prepared by photopolymer, the refractive index difference between the writing monomer and the film-forming resin is not significant enough, so that the refractive index modulated volume holographic grating cannot be quickly constructed, affecting the performance of the holographic recording medium. Summary of the invention

[0004] In view of this, the present invention proposes a (meth)acrylate monomer and a preparation method and application thereof, aiming to achieve a (meth)acrylate monomer with a higher refractive index so as to improve the holographic optical performance of a photopolymer holographic recording medium containing the (meth)acrylate monomer.

[0005] The (meth)acrylate monomers proposed in the first aspect of the present invention have general structural formulas as shown in Formulas G1, G2 and G3:

[0006]

[0007] Wherein, R1 is methyl or hydrogen; R2 and R3 are selected from hydrogen, Br, phenyl, methyl or in A1 in which is phenyl or methyl.

[0008] It can be seen from the above technical scheme that the (meth)acrylate monomer proposed in the first aspect of the present invention has a (meth)acrylate group, which has high refractive index and low volume shrinkage properties; and also contains groups such as aromatic rings with high molar refractive index and low molar volume, and some sulfur atoms that have high refractive index themselves, so that the molecules of the entire monomer present an extremely high refractive index as a whole. When the monomer has halogen and aromatic ring structures, since the monomer also has some alkyl chains, the viscosity of the entire monomer can be controlled within a reasonable range; the molecular size of the entire monomer is relatively small and not easy to agglomerate; the monomer of the above structure of the present invention is easy to synthesize and easy to obtain.

[0009] The second aspect of the present invention provides a method for preparing the (meth)acrylate monomer in each of the above examples, wherein compound P1 and compound P2 are sequentially added to a solvent at a molar ratio of 1:1, stirred evenly, and then a catalyst is added to react for 0.5h to 10h. After the reaction is completed, excess solvent is removed by rotary evaporation, and a high refractive index (meth)acrylate monomer is obtained by column chromatography separation;

[0010] Wherein, the structural formula of compound P1 is as follows: R2, R3 are selected from hydrogen, Br, phenyl, methyl or A1 is phenyl or methyl; the structural formula of compound P2 is Wherein R1 is methyl or hydrogen.

[0011] The preparation method of (meth)acrylate monomers proposed in the second aspect of the present invention has small molecular weight of each reaction monomer, few preparation steps, simple reaction conditions, easy synthesis, and monomers are not easy to agglomerate during the synthesis process.

[0012] The photopolymer holographic recording medium containing (meth)acrylate monomers provided in the third aspect of the present invention comprises a writing monomer, wherein the writing monomer comprises the (meth)acrylate monomer and a polymerizable monomer.

[0013] The third aspect of the present invention proposes a photopolymer holographic recording medium containing (meth)acrylate monomers. By adding (meth)acrylate monomers and polymerizable monomers, a writing monomer component with a higher refractive index can be formed, so that the writing monomer and the film-forming resin can have a larger refractive index difference, providing the photopolymer holographic recording medium with the necessary material basis for forming a phase-type volume holographic grating with refractive index modulation.

[0014] A fourth aspect of the present invention provides a holographic optical element, wherein the material of the holographic optical element includes the photopolymer holographic recording medium of the aforementioned examples.

[0015] The holographic optical element proposed in the fourth aspect of the present invention has excellent holographic performance, high diffraction efficiency, high sensitivity, and small exposure amount required.

[0016] A fifth aspect of the present invention provides an optical device, comprising the holographic optical element as described above.

[0017] The optical device proposed in the fifth aspect of the present invention, such as a head-up display device, an augmented reality device, a virtual reality device, a photopolymer holographic storage optical disc, etc., has excellent holographic performance.

[0018] It should be understood that the above general description and the following detailed description are exemplary and explanatory only and are not restrictive of the disclosure of the embodiments of the present invention. BRIEF DESCRIPTION OF THE DRAWINGS

[0019] In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the accompanying drawings required for use in the description of the embodiments will be briefly introduced below. Obviously, the accompanying drawings described below are some embodiments of the present invention. For ordinary technicians in this field, other accompanying drawings can be obtained like these accompanying drawings without paying any creative work.

[0020] Figure 1 is a schematic diagram of a chemical reaction equation for a preparation method of a (meth)acrylate monomer having a structural formula of G1-a according to some embodiments of the present invention;

[0021] Figure 2 is a schematic diagram of a chemical reaction equation for a preparation method of a (meth)acrylate monomer having a structural formula of G1-b according to some embodiments of the present invention;

[0022] Figure 3 is a schematic diagram of a chemical reaction equation for a preparation method of a (meth)acrylate monomer having a structural formula of G1-c proposed in some embodiments of the present invention;

[0023] Figure 4 is a schematic diagram of a chemical reaction equation for a preparation method of a (meth)acrylate monomer having a structural formula of G1-d proposed in some embodiments of the present invention;

[0024] Figure 5 is a schematic diagram of a chemical reaction equation for a preparation method of a (meth)acrylate monomer having a structural formula of G1-e proposed in some embodiments of the present invention;

[0025] Figure 6 is a schematic diagram of a chemical reaction equation for a preparation method of a (meth)acrylate monomer having a structural formula of G1-f according to some embodiments of the present invention;

[0026] Figure 7Schematic diagram of a chemical reaction equation for a preparation method of a (meth)acrylate monomer having a structural formula of G1-g according to some embodiments of the present invention;

[0027] Figure 8 is a schematic diagram of a chemical reaction equation for a preparation method of a (meth)acrylate monomer having a structural formula of G1-h proposed in some embodiments of the present invention;

[0028] Fig. 9 is a schematic diagram of a chemical reaction equation for a preparation method of a (meth)acrylate monomer having a structural formula of G1-i proposed in some embodiments of the present invention;

[0029] Fig.10 is a schematic diagram of a chemical reaction equation for a preparation method of a (meth)acrylate monomer having a structural formula of G1-j according to some embodiments of the present invention;

[0030] Fig.11 is a schematic diagram of a chemical reaction equation for a preparation method of a (meth)acrylate monomer having a structural formula of G1-k according to some embodiments of the present invention;

[0031] Fig.12 is a schematic diagram of a chemical reaction equation for a preparation method of a (meth)acrylate monomer having a structural formula of G1-1 proposed in some embodiments of the present invention;

[0032] Fig.13 is a schematic diagram of a chemical reaction equation for a preparation method of a (meth)acrylate monomer having a structural formula of G1-m proposed in some embodiments of the present invention;

[0033] Fig.14 is a schematic diagram of a chemical reaction equation for a preparation method of a (meth)acrylate monomer having a structural formula of G2-a according to some embodiments of the present invention;

[0034] Fig.15 is a schematic diagram of a chemical reaction equation for a preparation method of a (meth)acrylate monomer having a structural formula of G3-a according to some embodiments of the present invention;

[0035] Fig.16 is a graph showing holographic exposure characteristics of the photopolymer hologram recording medium 1-1 in Example 16, the photopolymer hologram recording medium 2-1 in Example 17, and the photopolymer hologram recording medium 3-1 in Example 18;

[0036] Fig.17 It is a comparative holographic exposure characteristic curve. DETAILED DESCRIPTION

[0037] The following will be combined with the drawings in the embodiments of the present invention to clearly and completely describe the technical solutions in the embodiments of the present invention. Obviously, the described embodiments are part of the embodiments of the present invention, not all of the embodiments. Based on the embodiments of the present invention, other embodiments obtained by ordinary technicians in this field without creative work are all within the scope of protection of the present invention.

[0038] The photopolymer material used for holographic recording realizes holographic recording by polymerizing the writing monomers under light and then forming a phase-type holographic grating with refractive index modulation with the film-forming resin. The monomers in the coherent bright area are consumed and the concentration is reduced, while the monomers in the coherent dark area hardly react. The difference in monomer concentration between the bright and dark areas causes the monomers in the dark area to begin to migrate to the bright area, and the film-forming resin in the bright area is squeezed into the dark area. Finally, the refractive index of the bright area is close to that of the polymer, and the refractive index of the dark area is close to that of the film-forming resin, thereby forming a phase-type volume holographic grating with refractive index modulation.

[0039] The present invention provides a high refractive index, low viscosity (meth)acrylate monomer as a component of the writing monomer, which is combined with an isocyanate-alcohol with a lower refractive index as a film-forming resin to form a refractive index-modulated volume holographic grating with a larger refractive index difference, thereby improving the holographic performance of the photopolymer holographic recording medium.

[0040] In the absence of conflict, the following embodiments and features of the embodiments may be combined with each other.

[0041] The (meth)acrylate monomer of the present invention is described below.

[0042] According to the present invention, a (meth)acrylate monomer has a general structural formula as shown in Formulas G1, G2 and G3:

[0043]

[0044] Wherein, R1 is methyl or hydrogen; R2 and R3 are selected from hydrogen, Br, phenyl, methyl or in A1 in which is phenyl or methyl.

[0045] As can be seen from the above technical solution, the (meth) acrylate monomer proposed in the present invention has a (meth) acrylate group, has high refractive index and low volume shrinkage properties; and also contains groups such as aromatic rings with high molar refractive index and low molar volume, and some atoms such as sulfur atoms that have high refractive index themselves, so that the entire monomer molecule presents an extremely high refractive index as a whole. When the monomer has halogen and aromatic ring structures, since the monomer also has some alkyl chains, the viscosity of the entire monomer can be controlled within a reasonable range; the molecular size of the entire monomer is relatively small and not easy to agglomerate; the monomer of the above structure of the present invention is easy to synthesize and easy to obtain.

[0046] In some examples, the (meth)acrylate monomer is selected from monomers having the following structural formula:

[0047]

[0048] Wherein R1 is methyl or hydrogen. Then, the (meth)acrylate monomers of each structure in the above examples all have the significant advantages of high refractive index, small molecular structure, short chain length, easy migration, low self-agglomeration and low viscosity.

[0049] In some examples, the refractive index of the (meth)acrylate monomer is 1.54 to 1.62, and the kinematic viscosity is 5 to 20 mm 2 / s.

[0050] The following is a description of the preparation method of the (meth)acrylate monomer of the present invention.

[0051] According to the preparation method of the (meth)acrylate monomer in each of the above examples proposed by the present invention, compound P1 and compound P2 are sequentially added to a solvent at a molar ratio of 1:1, stirred evenly, and then a catalyst is added to react for 0.5h to 10h. After the reaction is completed, excess solvent is removed by rotary evaporation, and (meth)acrylate monomers are separated by column chromatography;

[0052] Wherein, the structural formula of compound P1 is as follows: R2, R3 are selected from hydrogen, Br, phenyl, methyl or A1 is phenyl or methyl; the structural formula of compound P2 is Wherein R1 is methyl or hydrogen.

[0053] As can be seen from the above, the preparation method of (meth)acrylate monomers proposed in the present invention has small molecular weight of each reaction monomer, few preparation steps, simple reaction conditions, easy synthesis and operation, and monomers are not easy to agglomerate during the synthesis process.

[0054] In some examples, compound P1 is selected from compounds having the following structural formula:

[0055]

[0056] That is to say, after the compounds P1 and P2 of these structural formulas are synthesized, the (meth)acrylate monomers of the structural formulas listed above can be synthesized accordingly. In compound P2, in which R1 is methyl or hydrogen, the C=N double bond will open, and the H of -SH in compound P1 will transfer, thereby forming a polymerization of two monomers.

[0057] In some examples, the solvent is selected from one or more of ethanol, petroleum ether, dichloromethane, chloroform, ethyl acetate, tetrahydrofuran, toluene, acetonitrile, N,N-dimethylformamide or dimethyl sulfoxide. By adding these solvents, both compound P1 and compound P2 can be dissolved in the solvent, the solvent has good compatibility with both, and it is also convenient to control the concentration of the two compounds, so that the reaction system is more uniform; after the reaction is completed, these solvents have good volatility, so it is convenient to remove the above solvents to obtain the desired reacted substances, which is convenient for further processing.

[0058] In some examples, the catalyst is a tertiary amine catalyst or an organometallic catalyst. For example, the catalyst is selected from triethylenediamine, bis(dimethylaminoethyl) ether, dimethylethanolamine, 2-(2-dimethylamino-ethoxy)ethanol, trimethylhydroxyethylpropylenediamine, N,N-bis(dimethylaminopropyl)isopropanolamine, dibutyltin dilaurate, stannous octoate, potassium carboxylate catalysts and one or more of bismuth carboxylate catalysts. The catalyst is not limited to the above-listed types, as long as it can achieve the polymerization reaction of the aforementioned compound P1 and compound P2, and those skilled in the art should understand that these all fall within the scope of protection of the present invention.

[0059] The photopolymer type holographic recording medium containing a (meth)acrylate monomer of the present invention is described below.

[0060] The photopolymer holographic recording medium according to the present invention, which contains the (meth)acrylate monomers in the above examples, comprises a writing monomer, wherein the writing monomer comprises a (meth)acrylate monomer and a polymerizable monomer.

[0061] The third aspect of the present invention proposes a photopolymer holographic recording medium containing (meth)acrylate monomers. By adding (meth)acrylate monomers and polymerizable monomers, a writing monomer component with a higher refractive index can be formed, so that the writing monomer and the film-forming resin can have a larger refractive index difference, providing the photopolymer holographic recording medium with the necessary material basis for forming a phase-type volume holographic grating with refractive index modulation.

[0062] In some embodiments of the invention, the photopolymer holographic recording medium containing (meth)acrylate monomers comprises the following components in parts by weight:

[0063] First component: 20 to 50 parts of a compound having multiple isocyanate-reactive functional groups, for example, 20 parts, 30 parts, 40 parts, 50 parts, etc.

[0064] Second component: 10 to 40 parts of polyisocyanate compound, for example, 10 parts, 15 parts, 20 parts, 25 parts, 30 parts, 35 parts, 40 parts, etc.

[0065] The third component: 3 to 30 parts of (meth)acrylate monomers, for example, 3 parts, 4 parts, 5 parts, 10 parts, 15 parts, 20 parts, 25 parts, 30 parts, etc.

[0066] The fourth component: 0.1 to 47 parts of polymerizable monomers, for example, 0.1, 0.3, 1, 2, 5, 10, 15, 20, 25, 30, 40, 47, etc.

[0067] The fifth component: 0.1 to 4 parts of the photosensitive initiator composition, for example, 0.1, 0.2, 0.3, 0.5, 1, 1.5, 2.0, 2.5, 3.0, 3.5, 4, etc.

[0068] Sixth component: 0.1 to 3 parts of chain transfer agent, for example, 0.1, 0.2, 0.3, 0.4, 0.6, 0.8, 1.0, 1.5, 2.0, 2.2, 2.5, 2.8, 3, etc.

[0069] Seventh component: 0.1 to 3 parts of catalyst, for example, 0.1, 0.2, 0.3, 0.4, 0.6, 0.8, 1.0, 1.5, 2.0, 2.2, 2.5, 2.8, 3, etc.

[0070] The eighth component: 0.1 to 7 parts of additives, for example, 0.1, 0.2, 0.3, 0.5, 1, 1.5, 2.0, 2.5, 3.0, 3.5, 4, 5, 6, 6.5, 7, etc.

[0071] As can be seen from the above, the photopolymer holographic recording medium containing (meth)acrylate monomers proposed in the present invention can achieve full synergistic effect of each component by reasonably controlling the addition amount of each component, and the holographic performance of the final photopolymer holographic recording medium will not be deteriorated due to excessive or insufficient amount of a certain component, thereby ensuring that the comprehensive holographic performance of the final photopolymer holographic recording medium is better.

[0072] For example, by controlling the compound having multiple isocyanate reactive functional groups to 20 to 50 parts and the polyisocyanate compound to 10 to 40 parts, the first component and the second component can jointly form a film-forming resin with a lower refractive index, thereby providing support for the other components.

[0073] By controlling the (meth)acrylate monomers to 3 to 30 parts, and the polymerizable monomers to 0.1 to 47 parts, the third component and the fourth component are a writing monomer system, and the intermolecular bonding refractive index will be higher after polymerization, then the interaction of the above four components can realize a photopolymer holographic recording medium having a high refractive index component and a low refractive index component with a large refractive index difference, and form a high refractive index difference between the film-forming resin and the writing monomer. Therefore, under the action of light, the monomers in the bright area (such as the third component and the fourth component) are polymerized and consumed and the concentration is reduced, and the monomers in the dark area hardly react. The difference in monomer concentration between the bright and dark areas causes the high-concentration monomers in the dark area to begin to migrate to the bright area, and the components of the film-forming resin in the bright area (such as the first component and the second component) are squeezed into the dark area, so that the refractive index of the bright area is close to the refractive index of the third component and the fourth component, and the refractive index of the dark area is close to the refractive index of the first component and the second component, forming a phase-type volume holographic grating with refractive index modulation.

[0074] For example, by controlling the photosensitive initiator composition to 0.1 to 4 parts, it can absorb an appropriate number of photons during exposure and control the polymerization reaction at a certain speed, so that the grating can be formed quickly and obtain a higher diffraction efficiency; in addition, it can also ensure that the final holographic recording medium has the required light transmittance and that the grating has a certain diffraction efficiency.

[0075] For example, by controlling the chain transfer agent to 0.1 to 3 parts, the polymer chain length can be controlled within a certain reasonable range and the degree of polymerization can be effectively prevented, thereby ensuring that the final holographic recording medium has the required optical properties and diffraction efficiency.

[0076] For example, controlling the catalyst at 0.1 to 3 parts can effectively increase the reaction rate of related components and the consumption rate of related components after exposure, thereby quickly forming a concentration difference between the monomers in the bright and dark areas and realizing a refractive index modulated phase-type volume holographic grating.

[0077] For example, controlling the additive to 0.1 to 7 parts, taking the additive as a leveling agent as an example, can effectively improve the uniformity of the mixed liquid, improve fluidity, and reasonably control costs.

[0078] In some optional examples, the photopolymer holographic recording medium containing (meth)acrylate monomers includes the following components in parts by weight: a first component - 23 parts of a compound having multiple isocyanate-reactive functional groups, a second component - 23 parts of a polyisocyanate compound, a third component - 30 parts of a (meth)acrylate monomer, a fourth component - 18 parts of a polymerizable monomer, a fifth component - 2 parts of a photosensitive initiator combination agent, a sixth component - 2 parts of a chain transfer agent, a seventh component - 0.7 parts of a catalyst, and an eighth component - 1.3 parts of an additive.

[0079] In some optional examples, the photopolymer holographic recording medium containing (meth)acrylate monomers includes the following components in parts by weight: a first component - 20 parts of a compound having multiple isocyanate-reactive functional groups, a second component - 40 parts of a polyisocyanate compound, a third component - 3 parts of a (meth)acrylate monomer, a fourth component - 20 parts of a polymerizable monomer, a fifth component - 4 parts of a photosensitive initiator combination agent, a sixth component - 3 parts of a chain transfer agent, a seventh component - 3 parts of a catalyst, and an eighth component - 7 parts of an additive.

[0080] In some optional examples, the photopolymer holographic recording medium containing (meth)acrylate monomers includes the following components in parts by weight: a first component - 50 parts of a compound having multiple isocyanate-reactive functional groups, a second component - 10 parts of a polyisocyanate compound, a third component - 10 parts of a (meth)acrylate monomer, a fourth component - 20 parts of a polymerizable monomer, a fifth component - 2 parts of a photosensitive initiator combination agent, a sixth component - 1 part of a chain transfer agent, a seventh component - 2 parts of a catalyst, and an eighth component - 5 parts of an additive.

[0081] In some optional examples, the photopolymer holographic recording medium containing (meth)acrylate monomers includes the following components in parts by weight: a first component - 30 parts of a compound having multiple isocyanate-reactive functional groups, a second component - 10 parts of a polyisocyanate compound, a third component - 3 parts of a (meth)acrylate monomer, a fourth component - 47 parts of a polymerizable monomer, a fifth component - 4 parts of a photosensitive initiator combination agent, a sixth component - 1 part of a chain transfer agent, a seventh component - 3 parts of a catalyst, and an eighth component - 2 parts of an additive.

[0082] In some optional examples, the photopolymer holographic recording medium containing (meth)acrylate monomers includes the following components in parts by weight: a first component - 40 parts of a compound having multiple isocyanate-reactive functional groups, a second component - 10 parts of a polyisocyanate compound, a third component - 30 parts of a (meth)acrylate monomer, a fourth component - 8.8 parts of a polymerizable monomer, a fifth component - 4 parts of a photosensitive initiator combination agent, a sixth component - 0.1 parts of a chain transfer agent, a seventh component - 0.1 parts of a catalyst, and an eighth component - 7 parts of an additive.

[0083] In some optional examples, the photopolymer holographic recording medium containing (meth)acrylate monomers includes the following components in parts by weight: a first component - 30 parts of a compound having multiple isocyanate-reactive functional groups, a second component - 20 parts of a polyisocyanate compound, a third component - 30 parts of a (meth)acrylate monomer, a fourth component - 10 parts of a polymerizable monomer, a fifth component - 4 parts of a photosensitive initiator combination agent, a sixth component - 3 parts of a chain transfer agent, a seventh component - 0.5 parts of a catalyst, and an eighth component - 2.5 parts of an additive.

[0084] In some optional examples, the photopolymer holographic recording medium containing (meth)acrylate monomers includes the following components in parts by weight: a first component - 30 parts of a compound having multiple isocyanate-reactive functional groups, a second component - 30 parts of a polyisocyanate compound, a third component - 20 parts of a (meth)acrylate monomer, a fourth component - 10 parts of a polymerizable monomer, a fifth component - 0.1 parts of a photosensitive initiator combination agent, a sixth component - 0.8 parts of a chain transfer agent, a seventh component - 2 parts of a catalyst, and an eighth component - 7 parts of an additive.

[0085] In some optional examples, the photopolymer holographic recording medium containing (meth)acrylate monomers includes the following components in parts by weight: a first component - 30 parts of a compound having multiple isocyanate-reactive functional groups, a second component - 20 parts of a polyisocyanate compound, a third component - 20 parts of a (meth)acrylate monomer, a fourth component - 29.6 parts of a polymerizable monomer, a fifth component - 0.1 parts of a photosensitive initiator combination agent, a sixth component - 0.1 parts of a chain transfer agent, a seventh component - 0.1 parts of a catalyst, and an eighth component - 0.1 parts of an additive.

[0086] In some examples of the present invention, in the compound having multiple isocyanate reactive functional groups, the isocyanate reactive functional groups are hydroxyl groups. Hydroxyl groups are polar groups, among which alcoholic hydroxyl groups are easily oxidized and have high reactivity.

[0087] More specifically, the compound having multiple isocyanate reactive functional groups is selected from at least one of tetraethylene glycol, trimethylolethane, glycerol, triethanolamine, polyester polyols with a molecular weight of 200 to 2000, polycarbonate polyols, and polyether polyols. In some examples, the refractive index of the compound having multiple isocyanate reactive functional groups is less than 1.5.

[0088] In some examples of the present invention, the polyisocyanate compound is a compound having two or more isocyanate groups.

[0089] In a specific example, the polyisocyanate compound is selected from at least one of hexamethylene diisocyanate, trimethyl hexamethylene diisocyanate, (2,4,6-trioxotriazine-1,3,5(2H,4H,6H)-triyl) tris(hexamethylene) isocyanate, butane-1,4-diisocyanate, isophorone diisocyanate, and dicyclohexylmethane diisocyanate. In some examples, the refractive index of the polyisocyanate compound is less than 1.5.

[0090] In some examples of the present invention, the polymerizable monomer is selected from at least one of alkenyl naphthalene compounds, alkenyl anthracene compounds, alkenyl benzene compounds, acrylic compounds, methacrylic compounds, acrylate compounds, methacrylate compounds, N-vinyl pyrrole, N-vinyl carbazole, N-vinylimidazole, N-vinyl indole, N-vinyl pyrrolidone, and trans-N-3-ynyl butenyl carbazole.

[0091] In a specific example, the alkenyl naphthalene compound is selected from at least one of 1-vinyl naphthalene and 2-vinyl naphthalene.

[0092] In a specific example, the alkenyl anthracene compound is selected from at least one of 2-vinyl anthracene and 9-vinyl anthracene.

[0093] In a specific example, the alkenylbenzene compound is selected from at least one of styrene, 2-chlorostyrene, 2-bromostyrene, 3-chlorostyrene, 3-bromostyrene, 4-chlorostyrene, 4-bromostyrene, p-(chloromethyl)styrene, and p-(bromomethyl)styrene.

[0094] In a specific example, the methacrylic compound includes at least one of methacrylic acid and derivatives thereof.

[0095] In a specific example, the acrylate compound is selected from at least one of pentabromophenyl acrylate, pentachlorophenyl acrylate, phenoxyethyl acrylate, pentabromobenzyl acrylate, 2-naphthyl acrylate, 1,4-di(2-thionaphthyl)2-butyl acrylate, phenoxyethoxyethyl acrylate, bisphenol A diacrylate, tetrabromobisphenol A diacrylate, 2-phenoxyethyl acrylate, benzyl acrylate, p-chlorophenyl acrylate, 2,4,6-trichlorophenyl acrylate, p-bromophenyl acrylate, 2,4,6-tribromophenyl acrylate, propane-2,2-diylbis[(2,6-dibromo-4,1-phenylene)oxy(2-{[3,3,3-tri(4-chlorophenyl)propionyl]oxy}propane-3,1-diyl)oxyethane-2,1-diyl]diacrylate.

[0096] In a specific example, the methacrylate compound is selected from at least one of 2-phenoxyethyl methacrylate, benzyl methacrylate, p-bromophenyl methacrylate, p-chlorophenyl methacrylate, 2,4,6-trichlorophenyl methacrylate, pentabromophenyl methacrylate, pentachlorophenyl methacrylate, phenoxyethyl methacrylate, phenoxyethoxyethyl methacrylate, 1,4-di(2-thionaphthyl) 2-butyl methacrylate, pentabromobenzyl methacrylate, 2-naphthyl methacrylate, bisphenol A dimethacrylate, and tetrabromobisphenol A dimethacrylate.

[0097] In some examples of the present invention, the photosensitive initiator combination includes a photosensitizer and a photoinitiator. The photosensitizer can be matched with a photoinitiator to realize a visible light initiation system and adapt to lasers of different wavelengths. Under the irradiation of light in a specific wavelength range, the photosensitizer in the photoinitiator system is activated by the corresponding light, absorbs light energy, and transfers the light energy to the photoinitiator, so that the photoinitiator can be activated under more frequency light radiation to generate free radicals with initiation function. The photoinitiator free radicals can initiate monomer polymerization to realize the construction of holographic gratings, improve the photosensitivity of photopolymer holographic recording media, and broaden the range of optional radiation sources for light radiation.

[0098] It can be understood that, in other examples, when the present invention uses a wavelength-adapted photoinitiator, no photosensitizer may be added.

[0099] When the photosensitive initiator combination contains both a photosensitizer and a photoinitiator, further, the mass ratio of the photosensitizer to the photoinitiator is (0.001-1):(0.1-3). By controlling the mass ratio of the photosensitizer to the photoinitiator within the above range, the concentration of the photosensitizer can be effectively controlled, so that during the holographic exposure process, the number of absorbed photons is controlled within a suitable range, the speed of the polymerization reaction is controlled within a reasonable range, and the speed of grating formation is controlled within a certain range, thereby ensuring the light transmittance of the photopolymer holographic recording medium and obtaining excellent diffraction efficiency. In a more specific example, the mass of the photosensitizer is 1 / 10 to 1 / 3 of the mass of the photoinitiator, such as 1 / 10, 1 / 9, 1 / 8, 1 / 7, 1 / 6, 1 / 5, 1 / 4 or 1 / 3, etc.

[0100] In the present invention, different broadband responses can be achieved by regulating the type of photosensitizer. For example, the photosensitizer is a dye with high electron transfer efficiency under light.

[0101] In a specific example, the photosensitizer is selected from at least one of cyanine dyes, fluorescein dyes, coumarin ketone dyes, nitrogen-containing aromatic heterocyclic compounds, aromatic amine compounds, and benzylcycloalkane ketone compounds.

[0102] More specifically, the photosensitizer is selected from one or more of new methylene blue, thionine, basic yellow, pinacol cyanol chloride, rhodamine 6G, gallocyanine, ethyl violet, Victoria blue R, lapis lazuli blue, methylene blue, basic orange, daro red, pyrrole red Y, basic red 29, quinaldine red, crystal violet, ethyl violet, brilliant green, azure A, crystal violet white nitrile, and malachite green white nitrile.

[0103] In a specific example, the photoinitiator is selected from at least one of aromatic ketone compounds, benzoin and its derivatives, benzyl ketal, acylphosphine oxide, aryl ammonium borate, chromium salt, aryl diazonium salt, onium salt, and organic metal compound. It can also be other photoinitiators with similar functions, which are not limited in the present invention.

[0104] More specifically, the photoinitiator is selected from one or more of benzophenone, alkylbenzophenone, 4,4'-bis(dimethylamino)benzophenone, anthrone and halogenated benzophenone, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bisacylphosphine oxide, phenyl dihydroxyacetate, camphorquinone, α-aminoalkylphenone, α,α-dialkoxyacetophenone, α-hydroxyalkylphenone, triphenylhexyl borate tetrabutylammonium, tri-(3-fluorophenyl)hexyl borate tetrabutylammonium, tri-(3-chloro-4-methylphenyl)hexyl borate tetrabutylammonium, ferrocenyl compounds, iodonium salts, sulfonium salts, hexaarylbisimidazoles, etc. When these photoinitiators are irradiated with light within the corresponding wavelength range, they can be quickly activated and generate active free radicals, thereby initiating polymerization reactions between the components of the photopolymer holographic recording medium to achieve a difference in monomer concentration between the bright area and the dark area.

[0105] In some examples of the present invention, the chain transfer agent is a thiol compound.

[0106] In a specific example, the chain transfer agent includes one or more of dodecyl mercaptan, mercaptoethanol, hexanethiol, phenylethyl mercaptan, 5-(4-pyridyl)-1,3,4-oxadiazole-2-thiol, 4-methyl-4H-1,2,4-triazole-3-thiol, and the like.

[0107] In some examples of the present invention, the catalyst is a tertiary amine catalyst or an organic metal catalyst.

[0108] In a specific example, the catalyst is selected from at least one of triethylenediamine, bis(dimethylaminoethyl) ether, dimethylethanolamine, 2-(2-dimethylamino-ethoxy)ethanol, trimethylhydroxyethylpropylenediamine, N,N-bis(dimethylaminopropyl)isopropanolamine, dibutyltin dilaurate, stannous octoate, potassium carboxylate catalysts and bismuth carboxylate catalysts.

[0109] In some examples of the present invention, the additive includes one or more of a defoamer, a leveling agent, and a plasticizer.

[0110] In a specific example, the defoamer is an organosilicon defoamer and / or a polymer defoamer without organosilicon, and the weight of the defoamer in the photopolymer holographic recording medium is less than or equal to 3%. The defoamer can reduce the surface tension of the liquid and remove bubbles, thereby improving the fluidity of the mixture of the components.

[0111] More specifically, for example, BYK-011, BYK-012, BYK-014, BYK-023, BYK-051N, BYK-085, BYK-1610, BYK-1707, BYK-1740, BYK-1760 produced by BYK, DC65, AFE-7820 produced by Dow Corning, or any mixture of these defoamers in any proportion. BYK series defoamers have excellent defoaming performance, good compatibility with other components, and good dispersibility; among them, BYK-011, BYK-012, BYK-014 and BYK-051N are polymer defoamers that do not contain silicone. DC65 is a water-based ink that dries quickly, has good printing effects, and is not easy to fall off. AFE-7820 has high efficiency in defoaming performance.

[0112] In a specific example, the leveling agent is an organic silicon surface additive, and the weight of the leveling agent in the photopolymer holographic recording medium is less than or equal to 3%. For example, BYK-302, BYK-306, BYK-307, BYK-327, BYK-329, BYK-333, BYK-356, BYK-358, BYK-378, BYK-3455, BYK-3566 produced by BYK or any mixture of these surface additives. BYK series leveling agents have excellent leveling properties.

[0113] In a specific example, the plasticizer is selected from at least one of toluene, xylene, dimethylformamide, dimethylacetamide, glycerol, and phthalate, and the weight percentage of the plasticizer in the photopolymer holographic recording medium is less than or equal to 3%. The plasticizer is inserted between polymer molecular chains to weaken the stress between molecules, increase the mobility of molecular chains, and reduce crystallinity, thereby increasing the plasticity of the polymer.

[0114] In other examples of the present invention, the additive includes a dehydrating agent, and the weight of the dehydrating agent in the photopolymer holographic recording medium is less than or equal to 3%. The dehydrating agent can remove excess water during the reaction, so that the components are mixed better without stratification.

[0115] In a specific example, the dehydrating agent is selected from toluenesulfonyl isocyanate, triethyl orthoformate, CUWR-WB20 dehydrating agent of Guangzhou Yourun Synthetic Materials Co., Ltd., ALT-201 dehydrating agent of Anxiang Elite Chemical Co., Ltd., PCCI dehydrating agent of Shanghai Ruhr Chemical Trading Co., Ltd., etc.

[0116] Next, the application of the aforementioned photopolymer type holographic recording medium of the present invention will be described.

[0117] The holographic optical element proposed by the present invention is made of materials including the photopolymer holographic recording media in the above-mentioned examples. The holographic optical element includes but is not limited to a volume holographic grating.

[0118] From the above, it can be seen that the holographic optical element proposed in the present invention, because it contains the photopolymer holographic recording medium mentioned above in the present invention, also has the advantages of the photopolymer holographic recording medium of the present invention, has excellent holographic performance, high diffraction efficiency, high sensitivity, and small exposure required.

[0119] The optical device proposed by the present invention includes the holographic optical element as described above. The optical device includes but is not limited to a head-up display device (HUD), an augmented reality device (AR device, Augmented Reality), a virtual reality device (VR device, Virtual Reality), a photopolymer holographic storage disc, etc. The photopolymer holographic storage disc can be erasable and rewritable and record in real time, is suitable for storing a large amount of data, and has a very fast data transmission speed.

[0120] It can be seen from the above that the optical device proposed by the present invention, because it includes the holographic optical element mentioned above, also has the advantages of the holographic optical element of the present invention. The optical device has excellent holographic performance, clear images, and can store a large amount of data.

[0121] The (meth)acrylate monomer, the preparation method of the (meth)acrylate monomer, and the photopolymer holographic recording medium containing the (meth)acrylate monomer of the present invention are described below with reference to specific embodiments.

[0122] Example 1

[0123] The structural formula of the (meth)acrylate monomer in this embodiment is G1-a:

[0124] In this example, it is a (meth)acrylate monomer with a general structural formula of G1, and R1, R2 and R3 are all hydrogen.

[0125] Please refer to Figure 1 As shown, the preparation method of the (meth)acrylate monomer of the structural formula G1-a is as follows: The compound P1 and the structural formula are Compound P2 is added to a solvent such as ethanol in a molar ratio of 1:1, stirred evenly, and then a catalyst such as triethylenediamine is added to react for 5 hours. After the reaction is completed, the excess solvent is removed by rotary evaporation, and column chromatography is used to separate to obtain a (meth) acrylate monomer with a structural formula of G1-a, whose refractive index is 1.57 and characterization data are as follows:

[0126] 1 H NMR (400MHz, CDCl3) δ8.18(s,1H),7.28-7.38(m,5H),6.41(dd,1H),6.12(dd,1H),5.83(dd,1H),4.58(t,2H),3.13(t,2H).

[0127] 13 C NMR (101MHz, CDCl3) δ167.3,166.5,135.1,131.3,129.4,129.0,128.2,125.5,67.2,41.4.

[0128] The solvent and catalyst in this embodiment are only used for schematic description, and the solvent can be one or more of ethanol, petroleum ether, dichloromethane, chloroform, ethyl acetate, tetrahydrofuran, toluene, acetonitrile, N,N-dimethylformamide or dimethyl sulfoxide. The catalyst can be one or more of triethylenediamine, bis(dimethylaminoethyl) ether, dimethylethanolamine, 2-(2-dimethylamino-ethoxy)ethanol, trimethylhydroxyethylpropylenediamine, N,N-bis(dimethylaminopropyl)isopropanolamine, dibutyltin dilaurate, stannous octoate, potassium carboxylate catalysts and bismuth carboxylate catalysts, all of which should be within the scope of protection of the present invention.

[0129] Example 2

[0130] The structural formula of the (meth)acrylate monomer in this embodiment is G1-b:

[0131] In this example, the (meth)acrylate monomer has a general structural formula of G1, R2 is -S-CH3, and R1 and R3 are hydrogen.

[0132] Please refer to Figure 2 As shown, the preparation method of the (meth)acrylate monomer of the structural formula G1-b is as follows: The compound P1 and the structural formula are Compound P2 is added to a solvent such as petroleum ether in a molar ratio of 1:1, stirred evenly, and then a catalyst such as bis(dimethylaminoethyl) ether is added to react for 3 hours. After the reaction is completed, excess solvent is removed by rotary evaporation, and column chromatography is used to separate to obtain a (meth) acrylate monomer with a structural formula of G1-b, whose refractive index is 1.60, and the characterization data are as follows:

[0133] 1H NMR (400MHz, CDCl3) δ8.18(s,1H),7.26(d,2H),7.20(d,2H),6.41(dd,1H),6.12(dd,1H),5.83(dd,1H),4.58(t,2H),3.15(t,2H),2.38(s,3H).

[0134] 13 C NMR (101MHz, CDCl3) δ167.3,166.5,135.1,136.2,131.5,129.6,128.2,125.5,67.2,41.4,14.8.

[0135] The solvent and catalyst in this embodiment are only used for schematic description, and the solvent can be one or more of ethanol, petroleum ether, dichloromethane, chloroform, ethyl acetate, tetrahydrofuran, toluene, acetonitrile, N,N-dimethylformamide or dimethyl sulfoxide. The catalyst can be one or more of triethylenediamine, bis(dimethylaminoethyl) ether, dimethylethanolamine, 2-(2-dimethylamino-ethoxy)ethanol, trimethylhydroxyethylpropylenediamine, N,N-bis(dimethylaminopropyl)isopropanolamine, dibutyltin dilaurate, stannous octoate, potassium carboxylate catalysts and bismuth carboxylate catalysts, all of which should be within the scope of protection of the present invention.

[0136] Example 3

[0137] The structural formula of the (meth)acrylate monomer in this embodiment is G1-c:

[0138] In this example, it is a (meth)acrylate monomer with a general structural formula of G1, and R2 is A1 is phenyl, and R1 and R3 are hydrogen.

[0139] Please refer to Figure 3 As shown, the preparation method of the (meth)acrylate monomer of the structural formula G1-c is as follows: The compound P1 and the structural formula are Compound P2 is added to a solvent such as dichloromethane in a molar ratio of 1:1, stirred evenly, and then a catalyst such as dimethylethanolamine is added to react for 6 hours. After the reaction is completed, the excess solvent is removed by rotary evaporation, and column chromatography is used to separate to obtain a (meth) acrylate monomer with a structural formula of G1-c, whose refractive index is 1.63, and the characterization data are as follows:

[0140] 1H NMR (400MHz, CDCl3) δ8.18(s,1H),7.40-44(m,5H),7.22(d,2H),7.16(d,2H),6.41(dd,1H),6.12(dd,1H),5.83(dd,1H),4.58(t,2H),3.15(t,2H). 13 C NMR (101MHz, CDCl3) δ167.3,166.5,135.7,133.6,132.5,131.5,131.2,129.3,128.2,127.2,67.2,41.4.

[0141] The solvent and catalyst in this embodiment are only used for schematic description, and the solvent can be one or more of ethanol, petroleum ether, dichloromethane, chloroform, ethyl acetate, tetrahydrofuran, toluene, acetonitrile, N,N-dimethylformamide or dimethyl sulfoxide. The catalyst can be one or more of triethylenediamine, bis(dimethylaminoethyl) ether, dimethylethanolamine, 2-(2-dimethylamino-ethoxy)ethanol, trimethylhydroxyethylpropylenediamine, N,N-bis(dimethylaminopropyl)isopropanolamine, dibutyltin dilaurate, stannous octoate, potassium carboxylate catalysts and bismuth carboxylate catalysts, all of which should be within the scope of protection of the present invention.

[0142] Example 4

[0143] The structural formula of the (meth)acrylate monomer in this embodiment is G1-d:

[0144] In this example, it is a (meth)acrylate monomer with a general structural formula of G1, R1 is hydrogen, R2 is hydrogen, and R3 is a methyl group located at the meta position of S.

[0145] Please refer to Figure 4 As shown, the preparation method of the (meth)acrylate monomer of the structural formula G1-d is as follows: The compound P1 and the structural formula are Compound P2 is added to a solvent such as chloroform in a molar ratio of 1:1, stirred evenly, and then a catalyst such as 2-(2-dimethylamino-ethoxy)ethanol is added to react for 2 hours. After the reaction is completed, the excess solvent is removed by rotary evaporation, and column chromatography is used to separate to obtain a (meth) acrylate monomer with a structural formula of G1-d, whose refractive index is 1.57, and the characterization data are as follows:

[0146] 1H NMR(400MHz, CDCl3)δ8.18(s,1H),7.28(m,1H),7.11-7.14(m,2H),6.86(d,1H),6 .41(dd,1H),6.12(dd,1H),5.83(dd,1H),4.58(t,2H),3.15(t,2H),2.36(s,3H).

[0147] 13 C NMR (101MHz, CDCl3) δ167.3,166.5,140.7,135.0,136.1,131.3,128.9,128.2,126.4,125.8,67.2,41.4,21.3.

[0148] The solvent and catalyst in this embodiment are only used for schematic description, and the solvent can be one or more of ethanol, petroleum ether, dichloromethane, chloroform, ethyl acetate, tetrahydrofuran, toluene, acetonitrile, N,N-dimethylformamide or dimethyl sulfoxide. The catalyst can be one or more of triethylenediamine, bis(dimethylaminoethyl) ether, dimethylethanolamine, 2-(2-dimethylamino-ethoxy)ethanol, trimethylhydroxyethylpropylenediamine, N,N-bis(dimethylaminopropyl)isopropanolamine, dibutyltin dilaurate, stannous octoate, potassium carboxylate catalysts and bismuth carboxylate catalysts, all of which should be within the scope of protection of the present invention.

[0149] Example 5

[0150] The structural formula of the (meth)acrylate monomer in this embodiment is G1-e:

[0151] In this example, the (meth)acrylate monomer has a general structural formula of G1, R1 and R2 are hydrogen atoms, and R3 is a methyl group located in the para position to S.

[0152] Please refer to Figure 5 As shown, the preparation method of the (meth)acrylate monomer of the structural formula G1-e is as follows: The compound P1 and the structural formula are Compound P2 is added to a solvent such as ethyl acetate in a molar ratio of 1:1, stirred evenly, and then a catalyst such as trimethylolhydroxyethylpropylenediamine is added to react for 1 hour. After the reaction is completed, the excess solvent is removed by rotary evaporation, and column chromatography is used to separate to obtain a (meth) acrylate monomer with a structural formula of G1-e, whose refractive index is 1.57 and characterization data are as follows:

[0153] 1H NMR (400MHz, CDCl3) δ8.18(s,1H),6.80(d,2H),6.71(d,2H),6.41(dd,1H),6.12(dd,1H),5.83(dd,1H),4.58(t,2H),3.15(t,2H),2.32(s,3H).

[0154] 13 C NMR (101MHz, CDCl3) δ167.3,166.5,137.9,132.1,131.3,129.3,128.2,67.2,41.4,21.3.

[0155] The solvent and catalyst in this embodiment are only used for schematic description, and the solvent can be one or more of ethanol, petroleum ether, dichloromethane, chloroform, ethyl acetate, tetrahydrofuran, toluene, acetonitrile, N,N-dimethylformamide or dimethyl sulfoxide. The catalyst can be one or more of triethylenediamine, bis(dimethylaminoethyl) ether, dimethylethanolamine, 2-(2-dimethylamino-ethoxy)ethanol, trimethylhydroxyethylpropylenediamine, N,N-bis(dimethylaminopropyl)isopropanolamine, dibutyltin dilaurate, stannous octoate, potassium carboxylate catalysts and bismuth carboxylate catalysts, all of which should be within the scope of protection of the present invention.

[0156] Example 6

[0157] The structural formula of the (meth)acrylate monomer in this embodiment is G1-f:

[0158] In this example, the (meth)acrylate monomer has a general structural formula of G1, R1 and R2 are hydrogen, and R3 is bromine and is located at the meta position of S.

[0159] Please refer to Figure 6 As shown, the preparation method of the (meth)acrylate monomer of the structural formula G1-f is as follows: The compound P1 and the structural formula are Compound P2 is added to a solvent such as dichloromethane in a molar ratio of 1:1, stirred evenly, and then a catalyst such as dibutyltin dilaurate is added to react for 2 hours. After the reaction is completed, the excess solvent is removed by rotary evaporation, and column chromatography is used to separate to obtain a (meth) acrylate monomer with a structural formula of G1-f, whose refractive index is 1.58 and characterization data are as follows:

[0160] 1H NMR (400MHz, CDCl3) δ8.18(s,1H),7.32-7.35(m,3H),7.08(t,1H),6.41(dd,1H),6.12(dd,1H),5.83(dd,1H),4.58(t,2H),3.15(t,2H).

[0161] 13 C NMR (101MHz, CDCl3) δ169.1,166.5,137.3,133.0,131.3,129.9,128.4,128.2,127.5,67.2,14.2.

[0162] The solvent and catalyst in this embodiment are only used for schematic description, and the solvent can be one or more of ethanol, petroleum ether, dichloromethane, chloroform, ethyl acetate, tetrahydrofuran, toluene, acetonitrile, N,N-dimethylformamide or dimethyl sulfoxide. The catalyst can be one or more of triethylenediamine, bis(dimethylaminoethyl) ether, dimethylethanolamine, 2-(2-dimethylamino-ethoxy)ethanol, trimethylhydroxyethylpropylenediamine, N,N-bis(dimethylaminopropyl)isopropanolamine, dibutyltin dilaurate, stannous octoate, potassium carboxylate catalysts and bismuth carboxylate catalysts, all of which should be within the scope of protection of the present invention.

[0163] Example 7

[0164] The structural formula of the (meth)acrylate monomer in this embodiment is G1-g:

[0165] In this example, it is a (meth)acrylate monomer with a general structural formula of G1, R1 and R2 are hydrogen, and R3 is a methyl group located at the ortho position of sulfur.

[0166] Please refer to Figure 7 As shown, the preparation method of the (meth)acrylate monomer of the structural formula G1-g is as follows: The compound P1 and the structural formula are Compound P2 is added to a solvent such as toluene in a molar ratio of 1:1, stirred evenly, and then a catalyst such as dibutyltin dilaurate is added to react for 0.5h. After the reaction is completed, excess solvent is removed by rotary evaporation, and column chromatography is used to separate to obtain a (meth) acrylate monomer with a structural formula of G1-g, whose refractive index is 1.57 and characterization data are as follows:

[0167] 1H NMR(400MHz, CDCl3)δ8.18(s,1H),7.49(d,2H),7.31(d,1H),7.31(m,1H),6.4 1(dd,1H),6.12(dd,1H),5.83(dd,1H),4.58(t,2H),3.15(t,2H),2.34(s,3H).

[0168] 13 C NMR (101MHz, CDCl3) δ167.3,166.5,142.0,133.6,131.3,131.1,128.2,127.0,126.0,125.4,67.2,41.1,21.7.

[0169] The solvent and catalyst in this embodiment are only used for schematic description, and the solvent can be one or more of ethanol, petroleum ether, dichloromethane, chloroform, ethyl acetate, tetrahydrofuran, toluene, acetonitrile, N,N-dimethylformamide or dimethyl sulfoxide. The catalyst can be one or more of triethylenediamine, bis(dimethylaminoethyl) ether, dimethylethanolamine, 2-(2-dimethylamino-ethoxy)ethanol, trimethylhydroxyethylpropylenediamine, N,N-bis(dimethylaminopropyl)isopropanolamine, dibutyltin dilaurate, stannous octoate, potassium carboxylate catalysts and bismuth carboxylate catalysts, all of which should be within the scope of protection of the present invention.

[0170] Example 8

[0171] The structural formula of the (meth)acrylate monomer in this embodiment is G1-h:

[0172] In this example, it is a (meth)acrylate monomer with a general structural formula of G1, R1 is hydrogen, R2 is methyl, and R3 is methyl, and both are located at two adjacent positions of sulfur.

[0173] Please refer to Figure 8 As shown, the preparation method of the (meth)acrylate monomer of the structural formula G1-h is as follows: The compound P1 and the structural formula are Compound P2 is added to a solvent such as acetonitrile in a molar ratio of 1:1, stirred evenly, and then a catalyst such as stannous octoate is added to react for 10 hours. After the reaction is completed, the excess solvent is removed by rotary evaporation, and column chromatography is used to separate to obtain a (meth) acrylate monomer with a structural formula of G1-h, whose refractive index is 1.57, and the characterization data are as follows:

[0174] 1H NMR (400MHz, CDCl3) δ8.18(s,1H),7.39(d,2H),7.21(d,1H),6.41(dd,1H),6.12(dd,1H),5.83(dd,1H),4.58(t,2H),3.15(t,2H),2.34(s,6H).

[0175] 13 C NMR (101MHz, CDCl3) δ167.3,166.5,141.9,133.9,131.3,128.2,128.1,125.3,67.2,41.1,22.0.

[0176] The solvent and catalyst in this embodiment are only used for schematic description, and the solvent can be one or more of ethanol, petroleum ether, dichloromethane, chloroform, ethyl acetate, tetrahydrofuran, toluene, acetonitrile, N,N-dimethylformamide or dimethyl sulfoxide. The catalyst can be one or more of triethylenediamine, bis(dimethylaminoethyl) ether, dimethylethanolamine, 2-(2-dimethylamino-ethoxy)ethanol, trimethylhydroxyethylpropylenediamine, N,N-bis(dimethylaminopropyl)isopropanolamine, dibutyltin dilaurate, stannous octoate, potassium carboxylate catalysts and bismuth carboxylate catalysts, all of which should be within the scope of protection of the present invention.

[0177] Example 9

[0178] The structural formula of the (meth)acrylate monomer in this embodiment is G1-i:

[0179] In this example, the (meth)acrylate monomer has a general structural formula of G1, R1 is a methyl group, R2 is a phenyl group located at the para position of S, and R3 is hydrogen.

[0180] Please refer to Fig. 9 As shown, the preparation method of the (meth)acrylate monomer of the structural formula G1-i is as follows: The compound P1 and the structural formula are Compound P2 is added to a solvent such as N,N-dimethylformamide in a molar ratio of 1:1, and a catalyst such as a potassium carboxylate catalyst is added after stirring for 9 hours. After the reaction is completed, the excess solvent is removed by rotary evaporation, and column chromatography is used to separate to obtain a (meth) acrylate monomer with a structural formula of G1-i, whose refractive index is 1.59 and the characterization data are as follows:

[0181] 1H NMR (400MHz, CDCl3) δ8.18(s,1H),7.75(d,2H),7.41-7.61(m,7H),6.48(d,1H),6.40(d,1H),4.58(t,2H),3.15(t,2H),2.01(s,3H).

[0182] 13 C NMR (101MHz, CDCl3) δ167.3,167.2,140.9,137.6,136.0,134.0,129.9,129.2,128.2,127.9,127.6,125.2,67.6,41.1,17.9.

[0183] The solvent and catalyst in this embodiment are only used for schematic description, and the solvent can be one or more of ethanol, petroleum ether, dichloromethane, chloroform, ethyl acetate, tetrahydrofuran, toluene, acetonitrile, N,N-dimethylformamide or dimethyl sulfoxide. The catalyst can be one or more of triethylenediamine, bis(dimethylaminoethyl) ether, dimethylethanolamine, 2-(2-dimethylamino-ethoxy)ethanol, trimethylhydroxyethylpropylenediamine, N,N-bis(dimethylaminopropyl)isopropanolamine, dibutyltin dilaurate, stannous octoate, potassium carboxylate catalysts and bismuth carboxylate catalysts, all of which should be within the scope of protection of the present invention.

[0184] Example 10

[0185] The structural formula of the (meth)acrylate monomer in this embodiment is G1-j:

[0186] In this example, the (meth)acrylate monomer has a general structural formula of G1, R1 is a methyl group, R2 is a methyl group located at the para position to S, and R3 is a methyl group located at the ortho position to S.

[0187] Please refer to Fig.10 As shown, the preparation method of the (meth)acrylate monomer of the structural formula G1-j is as follows: The compound P1 and the structural formula are Compound P2 is added to a solvent such as dimethyl sulfoxide in a molar ratio of 1:1, and a catalyst such as a bismuth carboxylate catalyst is added after stirring evenly to react for 6 hours. After the reaction is completed, the excess solvent is removed by rotary evaporation, and column chromatography is used to separate to obtain a (meth) acrylate monomer with a structural formula of G1-j, whose refractive index is 1.57 and characterization data are as follows:

[0188] 1H NMR(400MHz, CDCl3)δ8.18(s,1H),7.26(d,1H),6.93(d,1H),6.91(s,1H),6.48(d, 1H),6.40(d,1H),4.58(t,2H),3.15(t,2H),2.31(s,3H),2.34(s,3H),2.01(s,3H).

[0189] 13 C NMR (101MHz, CDCl3) δ167.3,167.2,141.9,135.1,136.0,131.2,130.6,129.2,126.3,125.2,67.6,41.1,22.0,21.6,17.9.

[0190] The solvent and catalyst in this embodiment are only used for schematic description, and the solvent can be one or more of ethanol, petroleum ether, dichloromethane, chloroform, ethyl acetate, tetrahydrofuran, toluene, acetonitrile, N,N-dimethylformamide or dimethyl sulfoxide. The catalyst can be one or more of triethylenediamine, bis(dimethylaminoethyl) ether, dimethylethanolamine, 2-(2-dimethylamino-ethoxy)ethanol, trimethylhydroxyethylpropylenediamine, N,N-bis(dimethylaminopropyl)isopropanolamine, dibutyltin dilaurate, stannous octoate, potassium carboxylate catalysts and bismuth carboxylate catalysts, all of which should be within the scope of protection of the present invention.

[0191] Embodiment 11

[0192] The structural formula of the (meth)acrylate monomer in this embodiment is G1-k:

[0193] In this example, the (meth)acrylate monomer has a general structural formula of G1, R1 is a methyl group, and R2 and R3 are methyl groups located at two meta positions of S, respectively.

[0194] Please refer to Fig.11 As shown, the preparation method of the (meth)acrylate monomer of the structural formula G1-k is as follows: The compound P1 and the structural formula are Compound P2 is added to a solvent such as ethanol and acetonitrile in a molar ratio of 1:1, stirred evenly, and then a catalyst such as 2-(2-dimethylamino-ethoxy)ethanol is added to react for 4 hours. After the reaction is completed, the excess solvent is removed by rotary evaporation, and column chromatography is used to separate to obtain a (meth) acrylate monomer with a structural formula of G1-k, whose refractive index is 1.57, and the characterization data are as follows:

[0195] 1H NMR (400MHz, CDCl3) δ8.18(s,1H),7.01(s,3H),6.48(d,1H),6.40(d,1H),4.58(t,2H),3.15(t,2H),2.35(s,6H),2.01(s,3H).

[0196] 13 C NMR (101MHz, CDCl3) δ167.3,167.2,136.0,134.9,133.1,125.2,123.8,67.6,41.1,21.6,17.9.

[0197] The solvent and catalyst in this embodiment are only used for schematic description, and the solvent can be one or more of ethanol, petroleum ether, dichloromethane, chloroform, ethyl acetate, tetrahydrofuran, toluene, acetonitrile, N,N-dimethylformamide or dimethyl sulfoxide. The catalyst can be one or more of triethylenediamine, bis(dimethylaminoethyl) ether, dimethylethanolamine, 2-(2-dimethylamino-ethoxy)ethanol, trimethylhydroxyethylpropylenediamine, N,N-bis(dimethylaminopropyl)isopropanolamine, dibutyltin dilaurate, stannous octoate, potassium carboxylate catalysts and bismuth carboxylate catalysts, all of which should be within the scope of protection of the present invention.

[0198] Example 12

[0199] The structural formula of the (meth)acrylate monomer in this embodiment is G1-1:

[0200] In this example, the (meth)acrylate monomer has a general structural formula of G1, R1 is a methyl group, R2 is a hydrogen group, and R3 is a bromine group located in the para position to S.

[0201] Please refer to Fig.12 As shown, the preparation method of the (meth) acrylic acid ester monomer of the structural formula G1-1 is as follows: The compound P1 and the structural formula are Compound P2 is added to a solvent such as ethanol and toluene in a molar ratio of 1:1, stirred evenly, and then a catalyst such as 2-(2-dimethylamino-ethoxy)ethanol is added to react for 5 hours. After the reaction is completed, the excess solvent is removed by rotary evaporation, and column chromatography is used to separate to obtain a (meth) acrylate monomer with a structural formula of G1-1, whose refractive index is 1.59 and the characterization data are as follows:

[0202] 1H NMR (400MHz, CDCl3) δ8.18(s,1H),7.75(d,2H),7.25(d,2H),6.48(d,1H),6.40(d,1H),4.58(t,2H),3.15(t,2H),2.01(s,3H).

[0203] 13 C NMR (101MHz, CDCl3) δ167.3,167.2,136.0,134.1,131.9,131.6,125.2,119.9,67.5,41.1,17.9.

[0204] The solvent and catalyst in this embodiment are only used for schematic description, and the solvent can be one or more of ethanol, petroleum ether, dichloromethane, chloroform, ethyl acetate, tetrahydrofuran, toluene, acetonitrile, N,N-dimethylformamide or dimethyl sulfoxide. The catalyst can be one or more of triethylenediamine, bis(dimethylaminoethyl) ether, dimethylethanolamine, 2-(2-dimethylamino-ethoxy)ethanol, trimethylhydroxyethylpropylenediamine, N,N-bis(dimethylaminopropyl)isopropanolamine, dibutyltin dilaurate, stannous octoate, potassium carboxylate catalysts and bismuth carboxylate catalysts, all of which should be within the scope of protection of the present invention.

[0205] Embodiment 13

[0206] The structural formula of the (meth)acrylate monomer in this embodiment is G1-m:

[0207] In this example, it is a (meth)acrylate monomer with a general structural formula of G1, R1 is a methyl group, R2 is a hydrogen group, and R3 is a bromine group located at an ortho position to S.

[0208] Please refer to Fig.13 As shown, the preparation method of the (meth)acrylate monomer of the structural formula G1-m is as follows: The compound P1 and the structural formula are Compound P2 is added to a solvent such as ethanol and dimethyl sulfoxide in a molar ratio of 1:1, and then a catalyst such as dimethylethanolamine is added after stirring for 7 hours. After the reaction is completed, the excess solvent is removed by rotary evaporation, and column chromatography is used to separate to obtain a (meth) acrylate monomer with a structural formula of G1-m, whose refractive index is 1.58, and the characterization data are as follows:

[0209] 1H NMR (400MHz, CDCl3) δ8.18(s,1H),7.38(d,1H),7.20-7.25(m,3H),6.48(d,1H),6.40(d,1H),4.58(t,2H),3.15(t,2H),2.01(s,3H).

[0210] 13 C NMR (101MHz, CDCl3) δ167.3,167.2,136.0,135.8,131.9,131.6,128.0,127.7,125.2,121.2,67.5,41.1,17.9.

[0211] The solvent and catalyst in this embodiment are only used for schematic description, and the solvent can be one or more of ethanol, petroleum ether, dichloromethane, chloroform, ethyl acetate, tetrahydrofuran, toluene, acetonitrile, N,N-dimethylformamide or dimethyl sulfoxide. The catalyst can be one or more of triethylenediamine, bis(dimethylaminoethyl) ether, dimethylethanolamine, 2-(2-dimethylamino-ethoxy)ethanol, trimethylhydroxyethylpropylenediamine, N,N-bis(dimethylaminopropyl)isopropanolamine, dibutyltin dilaurate, stannous octoate, potassium carboxylate catalysts and bismuth carboxylate catalysts, all of which should be within the scope of protection of the present invention.

[0212] Embodiment 14

[0213] The structural formula of the (meth)acrylate monomer in this embodiment is G2-a:

[0214] In this example, it is a (meth)acrylate monomer with a general structural formula of G2, wherein R1 is a methyl group.

[0215] Please refer to Fig.14 As shown, the preparation method of the (meth)acrylate monomer of the structural formula G2-a is as follows: The compound P1 and the structural formula are Compound P2 is added to a solvent such as tetrahydrofuran in a molar ratio of 1:1, stirred evenly, and then a catalyst such as N,N-bis(dimethylaminopropyl)isopropanolamine is added to react for 9 hours. After the reaction is completed, excess solvent is removed by rotary evaporation, and column chromatography is used to separate to obtain a (meth)acrylate monomer with a structural formula of G2-a, whose refractive index is 1.60 and characterization data are as follows:

[0216] 1H NMR(400MHz, CDCl3)δ8.18(s,1H),7.96(dd,1H),7.79-7.84(m,2H),7.70(d,1H),7 .48-7.50(m,3H),6.48(d,1H),6.40(d,1H),4.58(t,2H),3.15(t,2H),2.01(s,3H).

[0217] 13 C NMR (101MHz, CDCl3) δ167.3,167.2,136.0,134.1,131.1,130.6,129.9,128.4,128.1,126.6,126.2,125.2,67.5,41.1,17.9.

[0218] The solvent and catalyst in this embodiment are only used for schematic description, and the solvent can be one or more of ethanol, petroleum ether, dichloromethane, chloroform, ethyl acetate, tetrahydrofuran, toluene, acetonitrile, N,N-dimethylformamide or dimethyl sulfoxide. The catalyst can be one or more of triethylenediamine, bis(dimethylaminoethyl) ether, dimethylethanolamine, 2-(2-dimethylamino-ethoxy)ethanol, trimethylhydroxyethylpropylenediamine, N,N-bis(dimethylaminopropyl)isopropanolamine, dibutyltin dilaurate, stannous octoate, potassium carboxylate catalysts and bismuth carboxylate catalysts, all of which should be within the scope of protection of the present invention.

[0219] Embodiment 15

[0220] The structural formula of the (meth)acrylate monomer in this embodiment is G3-a:

[0221] In this example, it is a (meth)acrylate monomer with a general structural formula of G3, wherein R1 is a methyl group.

[0222] Please refer to Fig.15 As shown, the preparation method of the (meth)acrylate monomer of the structural formula G3-a is as follows: The compound P1 and the structural formula are Compound P2 is added to a solvent such as toluene in a molar ratio of 1:1, stirred evenly, and then a catalyst such as dimethylethanolamine is added to react for 6 hours. After the reaction is completed, the excess solvent is removed by rotary evaporation, and column chromatography is used to separate to obtain a (meth) acrylate monomer with a structural formula of G3-a, whose refractive index is 1.60, and the characterization data are as follows:

[0223] 1H NMR (400MHz, CDCl3) δ8.12-8.18(m,3H),7.93(d,1H),7.40-7.59(m,4H),6.48(d,1H),6.40(d,1H),4.58(t,2H),3.15(t,2H),2.01(s,3H).

[0224] 13 C NMR (101MHz, CDCl3) δ167.3,167.2,136.0,134.1,132.0,129.8,128.7,128.3,126.6,126.2,125.2,125.1,67.5,41.1,17.9.

[0225] The solvent and catalyst in this embodiment are only used for schematic description, and the solvent can be one or more of ethanol, petroleum ether, dichloromethane, chloroform, ethyl acetate, tetrahydrofuran, toluene, acetonitrile, N,N-dimethylformamide or dimethyl sulfoxide. The catalyst can be one or more of triethylenediamine, bis(dimethylaminoethyl) ether, dimethylethanolamine, 2-(2-dimethylamino-ethoxy)ethanol, trimethylhydroxyethylpropylenediamine, N,N-bis(dimethylaminopropyl)isopropanolamine, dibutyltin dilaurate, stannous octoate, potassium carboxylate catalysts and bismuth carboxylate catalysts, all of which should be within the scope of protection of the present invention.

[0226] Example 16

[0227] Photopolymer holographic recording media 1-1 to 1-13 containing the (meth)acrylate monomers in Examples 1-13 were used: the specific components of the photopolymer holographic recording media 1-1 to 1-13 are shown in Table 1 below.

[0228] Table 1 Compositions of the photopolymer holographic recording media in Example 16

[0229]

[0230]

[0231]

[0232] In this embodiment, the components selected may also be other components listed above, and these embodiments should not be construed as limiting the scope of protection of the present invention.

[0233] Embodiment 17

[0234] The components of the photopolymer holographic recording medium 1-1 are substantially the same as those of Example 16, except that 0.3 parts of basic yellow is used as the photosensitizer, and the (meth)acrylate monomer of structural formula G1-a in Example 16 is replaced with the (meth)acrylate monomer of structural formula G2-a in Example 14, thereby forming a photopolymer holographic recording medium 2-1 containing the (meth)acrylate monomer of Example 14.

[0235] Embodiment 18

[0236] The components of the photopolymer holographic recording medium 1-1 are substantially the same as those of Example 16, except that 0.3 parts of eosin is used as the photosensitizer, and the (meth)acrylate monomer with the structural formula G1-a of Example 16 is replaced with the (meth)acrylate monomer with the structural formula G3-a of Example 15, thereby forming a photopolymer holographic recording medium 3-1 containing the (meth)acrylate monomer of Example 15.

[0237] Comparative Example

[0238] The composition of the photopolymer holographic recording medium is substantially the same as that of Example 16, except that the (meth)acrylate monomer of Example 16 is removed so that the proportion of the (meth)acrylate monomer becomes 0, while the polymerizable monomer is increased to 55, thereby obtaining an ordinary photopolymer holographic recording medium.

[0239] Test example

[0240] The performance of the holographic recording media of Examples 16-18 and the comparative example was tested. During the test, according to the different photosensitive systems, different wavelengths of lasers were selected for exposure in Examples 16, 17 and 18. The exposure light intensity was 3 mW / cm 2 The exposure wavelength of the photopolymer holographic recording medium 1-1 is 633 nm, the exposure wavelength of the embodiment photoholographic recording medium 2-1 is 457 nm, and the exposure wavelength of the photopolymer holographic recording medium 3-1 is 532 nm.

[0241] The test method includes the following steps:

[0242] Solid-state lasers with wavelengths of 633nm, 457nm, and 532nm were used as light sources. After passing through a beam expander, beam splitter, and half-wave plate, two beams with the same light intensity and a diameter of 8mm were obtained. The two beams intersected in the prepared holographic recording medium for exposure, and the light intensity was 3mW / cm 2The detection light source is a 785nm wavelength solid laser that does not react with the recording medium. The detection light is incident on the exposure area from the Bragg angle. The transmitted light and diffracted light are monitored in real time by the photodetector. The single grating diffraction efficiency (η) of the photopolymer holographic recording medium and the photosensitivity (S) of the photopolymer holographic recording medium are calculated by formulas (1) to (3).

[0243]

[0244] Where η is the diffraction efficiency, η max is the highest diffraction efficiency, I d is the diffracted light, I t is the transmitted light, S is the photosensitivity, E is the exposure energy, and ΔE is the exposure energy when the highest diffraction efficiency is achieved.

[0245] The holographic performance tests of the photopolymer holographic recording media 1-1 to 1-13 in Example 16, the photopolymer holographic recording medium 2-1 in Example 17, the photopolymer holographic recording medium 3-1 in Example 18, and the ordinary photopolymer holographic recording medium of the comparison example are shown in Table 2 below.

[0246] Table 2 Holographic performance test table of each photopolymer holographic recording medium in Example 16-Example 18 and Comparative Example

[0247]

[0248] The photopolymer holographic recording media 1-1 to 1-13 containing (meth)acrylate monomers in Example 16, the photopolymer holographic recording medium 2-1 in Example 17, the photopolymer holographic recording medium 3-1 in Example 18 and the ordinary photopolymer holographic recording medium in the comparative example were selected for holographic performance testing.

[0249] The holographic performance graphs drawn using the photopolymer holographic recording medium 1-1 in Example 16, the photopolymer holographic recording medium 2-1 in Example 17, and the photopolymer holographic recording medium 3-1 in Example 18 are shown in FIG. Fig.16 As shown in the figure, it is finally measured that the diffraction efficiency of the photopolymer holographic recording medium of the present invention is greater than 95%, and the exposure amount is less than 20mJ / cm 2 , sensitivity greater than 100cm 2 / mJ.

[0250] And as Fig.17 As shown, the conventional photopolymer holographic recording medium of the comparative example was exposed at an exposure wavelength of 633 nm and an exposure light intensity of 3 mW / cm 2The diffraction efficiency of the ordinary photopolymer holographic recording medium in the comparative example is less than 50%, and the required exposure is greater than 100 mJ / cm 2 , the sensitivity is lower.

[0251] In summary, reference Fig.16 , Fig.17 As shown in Table 2, the diffraction efficiency of the photopolymer holographic recording medium in the embodiment of the present invention is much higher than that in the comparative example, the sensitivity is much greater than that in the comparative example, and the required exposure amount is small.

[0252] The above is only a specific embodiment of the present invention, but the protection scope of the present invention is not limited thereto. Any technician familiar with the technical field can easily think of various equivalent modifications or replacements within the technical scope disclosed by the present invention, and these modifications or replacements should be included in the protection scope of the present invention. Therefore, the protection scope of the present invention shall be based on the protection scope of the claims.

Claims

1. A (meth)acrylate monomer, characterized in that: The general structural formulas are shown in formulas G1, G2 and G3: Wherein, R1 is methyl or hydrogen; R2 and R3 are selected from hydrogen, Br, phenyl, methyl or in A1 in which is phenyl or methyl.

2. The (meth)acrylate monomer according to claim 1, characterized in that The (meth)acrylate monomer is selected from monomers having the following structural formula: Wherein R1 is methyl or hydrogen.

3. The (meth)acrylate monomer according to claim 1, characterized in that The (meth)acrylate monomer has a refractive index of 1.54 to 1.62 and a kinematic viscosity of 5 to 20 mm 2 / s.

4. A method for preparing a (meth)acrylate monomer as claimed in any one of claims 1 to 3, characterized in that: Compound P1 and compound P2 are sequentially added to a solvent at a molar ratio of 1:1, and after being stirred evenly, a catalyst is added to react for 0.5 h to 10 h. After the reaction is completed, excess solvent is removed by rotary evaporation, and (meth)acrylate monomers are separated by column chromatography; Wherein, the structural formula of compound P1 is as follows: R2, R3 are selected from hydrogen, Br, phenyl, methyl or A1 is phenyl or methyl; the structural formula of compound P2 is Wherein R1 is methyl or hydrogen.

5. The method for preparing a (meth)acrylate monomer according to claim 4, characterized in that: The compound P1 is selected from compounds having the following structural formula:

6. The method for preparing a (meth)acrylate monomer according to claim 4, characterized in that: The solvent is selected from one or more of ethanol, petroleum ether, dichloromethane, chloroform, ethyl acetate, tetrahydrofuran, toluene, acetonitrile, N,N-dimethylformamide or dimethyl sulfoxide; and / or, The catalyst is a tertiary amine catalyst or an organic metal catalyst.

7. The method for preparing a (meth)acrylate monomer according to claim 6, wherein: The catalyst is selected from one or more of triethylenediamine, bis(dimethylaminoethyl) ether, dimethylethanolamine, 2-(2-dimethylamino-ethoxy)ethanol, trimethylhydroxyethylpropylenediamine, N,N-bis(dimethylaminopropyl)isopropanolamine, dibutyltin dilaurate, stannous octoate, potassium carboxylate catalysts and bismuth carboxylate catalysts.

8. A photopolymer holographic recording medium containing the (meth)acrylate monomer according to any one of claims 1 to 3, characterized in that: The invention comprises a writing monomer, wherein the writing monomer comprises the (meth)acrylic acid ester monomer and a polymerizable monomer.

9. The photopolymer holographic recording medium according to claim 8, wherein: The composition comprises the following components in parts by weight: First component: 20 to 50 parts of a compound having multiple isocyanate-reactive functional groups; The second component: 10 to 40 parts of polyisocyanate compound; The third component: 3 to 30 parts of (meth)acrylate monomer; The fourth component: 0.1 to 47 parts of polymerizable monomer; The fifth component: 0.1 to 4 parts of photosensitive initiator combination agent; The sixth component: 0.1 to 3 parts of chain transfer agent; The seventh component: 0.1 to 3 parts of catalyst; The eighth component: 0.1 to 7 parts of additives.

10. The photopolymer holographic recording medium according to claim 8, wherein: In the compound having a plurality of isocyanate-reactive functional groups, the isocyanate-reactive functional groups are hydroxyl groups; and / or, The polyisocyanate compound is a compound having two or more isocyanate groups; and / or, The polymerizable monomer is selected from at least one of alkenyl naphthalene compounds, alkenyl anthracene compounds, alkenyl benzene compounds, acrylic compounds, methacrylic compounds, acrylate compounds, methacrylate compounds, N-vinyl pyrrole, N-vinyl carbazole, N-vinylimidazole, N-vinyl indole, N-vinyl pyrrolidone, and trans-N-3-ynyl butenyl carbazole; and / or, The photosensitive initiator combination comprises a photosensitizer and a photoinitiator; the mass ratio of the photosensitizer to the photoinitiator is (0.001-1):(0.1-3); and / or, The chain transfer agent is a thiol compound; and / or, The catalyst is a tertiary amine catalyst or an organic metal catalyst; and / or, The additives include one or more of a defoamer, a leveling agent and a plasticizer.

11. A holographic optical element, characterized in that: The raw material of the holographic optical element comprises the photopolymer holographic recording medium as claimed in any one of claims 8 to 10.

12. An optical device, characterized in that: Comprising the holographic optical element as claimed in claim 11.

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