Four-functionality oxetanyl silicon-containing monomer as well as preparation method and application thereof

Abstract

The invention relates to compounds of formula (I), wherein the variables are as defined in the description. The invention also relates to a preparation method of the compound shown in the formula (I), a photocurable composition containing the compound shown in the formula (I), a photocurable material prepared from the photocurable composition and application of the compound shown in the formula (I) in the field of photocurable materials. The invention has the following beneficial effects: (1) the compound of formula (I) has good photopolymerization activity, and can be rapidly cured under the action of ultraviolet light; and (2) the surface hydrophobicity, heat resistance and tensile property of the cured film can be improved by adding the compound in the formula (I). # imgabs0 #

Description

Technical Field

[0001] The present invention relates to the field of photocurable materials, and more particularly to a tetrafunctional oxetane-based silicon-containing monomer. The present invention also relates to a method for preparing the monomer, a photocurable composition containing the monomer, a photocurable material obtained from the photocurable composition, and application of the monomer in the field of photocurable materials. Background Art

[0002] Photopolymerization technology is a process in which chemically active liquid monomers and oligomers are cross-linked by ultraviolet or visible light to quickly transform into solid polymers. It is a green, sustainable and environmentally friendly technology that has gradually developed since the 1960s. Compared with traditional thermal polymerization technology, photopolymerization has many advantages of its own, such as green environmental protection, no solvent consumption and volatilization, high efficiency, fast speed and low cost. Photopolymerization technology has been widely used in many fields, such as photocurable coatings, photocurable inks and photocurable adhesives. Moreover, with the continuous development and progress of photocurable technology, photopolymerization technology is now developing more rapidly in cutting-edge fields such as photoresists, laser three-dimensional imaging and three-dimensional modeling. Compared with free radical photopolymerization, although the cationic photopolymerization system has a slower polymerization speed, it has the advantages of anti-oxidation inhibition, small volume shrinkage, good adhesion and high surface hardness. Oxetane has the advantages of low viscosity, low toxicity, low volatility and low volume shrinkage. As a cationic photopolymerization monomer, it has been widely used. In addition, organosiloxane has the advantages of excellent heat resistance, water repellency, flexibility, electrical insulation and physiological inertness. Although monomers containing organosiloxane and oxygen heterocyclic structures already exist, most of the existing oxacyclobutane-based silicon-containing monomers are monofunctional monomers, and their self-polymerization rate is too slow to meet application requirements. There is still a demand for monomers containing organosiloxane and oxygen heterocyclic structures that have a fast self-polymerization rate and can give materials better properties such as surface hydrophobicity, heat resistance and tensile properties. Summary of the invention

[0003] The purpose of the present invention is to provide a tetrafunctional oxetane-based silicon-containing monomer. The inventors have found through research that the tetrafunctional oxetane-based silicon-containing monomer has a good polymerization rate and conversion rate and can promote the polymerization of other cationic monomers, while giving the material excellent tensile properties, heat resistance, surface hydrophobicity, etc.

[0004] Another object of the present invention is to provide a method for preparing the tetrafunctional oxetane-based silicon-containing monomer of the present invention. The preparation method is simple and easy to operate, has mild conditions, readily available raw materials, and low cost.

[0005] Specifically, the present invention relates to the following aspects:

[0006] 1. Compound of formula (I):

[0007]

[0008] Wherein R1, R2, R3, and R4 are the same or different and are independently an organic group having 1 to 12 carbon atoms; R5, R6, R7, and R8 are the same or different and are independently H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 hydroxyalkyl, C1-C6 alkoxy, or C1-C6 haloalkoxy; and L1, L2, L3, and L4 are the same or different and are independently a connecting group having 2 to 30 carbon atoms.

[0009] 2. The compound of formula (I) according to item 1, wherein R1, R2, R3, R4 are the same or different and are independently C6-C 10 Aryl, C1-C 12 Alkyl, C1-C 12 Alkoxy, one or more independently selected from NR a C2-C 12 Alkyl or one or more independently selected from NR a C2-C 12 Alkoxy, where R a It is H or C1-C4 alkyl.

[0010] 3. A compound of formula (I) according to item 1, wherein

[0011] R1, R2, R3, R4 are the same or different and are independently C6-C 10 Aryl, C1-C6 alkyl, C1-C6 alkoxy or one or more independently selected from NR a , O, S non-adjacent heteroatom interval C2-C6 alkyl, wherein R a Preferably, R1, R2, R3, R4 are the same or different and are independently phenyl, C1-C4 alkyl, C1-C4 alkoxy or one or more independently selected from NR a , O, S non-adjacent heteroatom interval C2-C4 alkyl, wherein R a is H or C1-C4 alkyl; and / or

[0012] R5, R6, R7, R8 are the same or different and independently represent H, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 hydroxyalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy; and / or

[0013] L1, L2, L3, L4 are the same or different and are independently C2-C 10 Alkylene or C3-C10 Cycloalkylene.

[0014] 4. A compound of formula (I) according to item 1, wherein R1, R2, R3, R4 are the same or different and are independently phenyl, C1-C4 alkyl, C1-C4 alkoxy or are independently selected from NR a , O, S non-adjacent heteroatom interval C2-C4 alkyl, wherein R a is H or C1-C4 alkyl; R5, R6, R7, R8 are the same or different and independently are H, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 hydroxyalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy; and L1, L2, L3, L4 are the same or different and independently are C2-C6 alkylene or C4-C8 cycloalkylene;

[0015] Preferably, R1, R2, R3, and R4 are the same or different and are independently C1-C4 alkyl; R5, R6, R7, and R8 are the same or different and are independently H or C1-C4 alkyl; and L1, L2, L3, and L4 are the same or different and are independently C2-C4 alkylene or C5-C6 cycloalkylene.

[0016] 5. The compound of formula (I) according to item 1, which is a compound of formula (I-1):

[0017]

[0018] 6. A method for preparing a compound of formula (I) according to any one of items 1 to 5, comprising reacting a compound of formula (II) with a compound of formula (III) to obtain a compound of formula (I):

[0019]

[0020] Where R a R5, R6, R7, R8 are independently as defined in any one of items 1 and 3-5, L is an alkenyl or cycloalkenyl group having 2 to 30 carbon atoms,

[0021]

[0022] wherein R1, R2, R3 and R4 are as defined in any one of items 1-5.

[0023] 7. The method according to item 6, wherein

[0024] The reaction of the compound of formula (II) with the compound of formula (III) is carried out in the presence of a Karstedt catalyst or a Speier catalyst, preferably, the amount of the catalyst is 2-500 ppm, preferably 80-200 ppm, based on the weight of the compound of formula (III); and / or

[0025] The molar ratio of the compound of formula (II) to the compound of formula (III) is 4:1-6:1, preferably 4:1-4.5:1; and / or

[0026] The reaction between the compound of formula (II) and the compound of formula (III) is carried out at 80-110°C, preferably 85-100°C; and / or

[0027] The reaction between the compound of formula (II) and the compound of formula (III) is carried out for 6 to 20 hours, preferably 10 to 16 hours.

[0028] 8. A photocurable composition comprising the compound of formula (I) according to any one of items 1 to 5 as a polymerizable monomer.

[0029] 9. A photocurable material obtained from the photocurable composition according to item 8.

[0030] 10. Use of the compound of formula (I) according to any one of items 1 to 5 in photocurable coatings, adhesives, inks and photoresists. BRIEF DESCRIPTION OF THE DRAWINGS

[0031] Figure 1 3 is a graph showing the change in alicyclic epoxy conversion rate with irradiation time in a system containing compound (I-1) prepared in Example 1.

[0032] Figure 2 It is a curve diagram showing the change of the conversion rate of compound (I-1) in the system containing compound (I-1) prepared in Example 1 as a function of irradiation time.

[0033] Figure 3 Graphs showing water contact angles of a blank E4221 / VOH cured film and a cured film of a system containing compound (I-1) prepared in Example 1.

[0034] Figure 4 : is the thermogravimetric curve of the blank E4221 / VOH cured film and the cured film of the system containing the compound (I-1) prepared in Example 1.

[0035] Figure 5 It is a graph showing the mechanical properties of a blank E4221 / VOH cured film and a cured film of a system containing compound (I-1) prepared in Example 1. DETAILED DESCRIPTION OF THE INVENTION

[0037] In the following description of the present invention, unless otherwise explicitly stated, the numerical values ​​in the present application can be regarded as modified by the word "about". However, the inventors have reported the numerical values ​​in the examples as accurately as possible, although these numerical values ​​inevitably include certain errors.

[0038] In the present application, unless explicitly excluded, the specific or preferred embodiments of the present invention can be combined. In addition, each element of the embodiment of the present application is a specific preferred selection of the corresponding higher-level technical features. If the higher-level technical features can be combined with other higher-level features, the elements of the embodiment, i.e. the specific preferred selection, can also be combined with the other higher-level features. These combinations should be regarded as a part of the original recorded content of the present application. DETAILED DESCRIPTION

[0039] According to one aspect of the present invention, there is provided a compound of the following formula (I):

[0040]

[0041] Wherein R1, R2, R3, and R4 are the same or different and are independently an organic group having 1 to 12 carbon atoms; R5, R6, R7, and R8 are the same or different and are independently H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 hydroxyalkyl, C1-C6 alkoxy, or C1-C6 haloalkoxy; and L1, L2, L3, and L4 are the same or different and are independently a connecting group having 2 to 30 carbon atoms.

[0042] In one embodiment of the present invention, the organic group having 1 to 12 carbon atoms is C6-C 10 Aryl, C1-C 12 Alkyl, C1-C 12 Alkoxy, one or more independently selected from NR a C2-C 12 Alkyl or one or more independently selected from NR a C2-C 12 Alkoxy, where R a It is H or C1-C4 alkyl.

[0043] In the present invention, the prefix "C n -C m " in each case means that the number of carbon atoms contained in the group is nm.

[0044] "Halogen" refers to fluorine, chlorine, bromine and iodine. In the present invention, preferably, the halogen includes fluorine, chlorine or a combination thereof.

[0045] The term "C n -C m The term "alkyl" refers to a branched or unbranched saturated hydrocarbon radical having, for example, 1 to 12, preferably 1 to 6 and particularly preferably 1 to 4, carbon atoms, for example methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl and isomers thereof, in particular methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylpropyl Methylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, etc. C1-C6 alkyl can be methyl, ethyl, propyl, butyl, pentyl, hexyl and isomers thereof, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, etc. C1-C4 alkyl can be methyl, ethyl, propyl, butyl and isomers thereof, in particular methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl.

[0046] The term "C n -C mThe term "alkenyl" refers to a branched or unbranched hydrocarbon radical having, for example, 2 to 12, preferably 2 to 6, particularly preferably 2 to 4, carbon atoms and a C=C double bond, for example vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl and isomers thereof, in particular vinyl, n-propenyl, 1-methylvinyl, n-butenyl, 1-methylpropenyl, 2-methylpropenyl, 1- ,1-dimethylvinyl, n-pentenyl, 1-methylbutenyl, 2-methylbutenyl, 3-methylbutenyl, 2,2-dimethylpropenyl, 1-ethylpropenyl, 1,1-dimethylpropenyl, 1,2-dimethylpropenyl, n-hexenyl, 1-methylpentenyl, 2-methylpentenyl, 3-methylpentenyl, 4-methylpentenyl, 1,1-dimethylbutenyl, 1,2-dimethylbutenyl, 1,3-dimethylbutenyl, 2,2 C2-C6 alkenyl may be ethyl butenyl, 2,3-dimethyl butenyl, 3,3-dimethyl butenyl, 1-ethyl butenyl, 2-ethyl butenyl, 1,1,2-trimethyl propenyl, 1,2,2-trimethyl propenyl, 1-ethyl-1-methyl propenyl, 1-ethyl-2-methyl propenyl, n-heptenyl, n-octenyl, 2-ethyl hexenyl, n-nonenyl, n-decenyl, n-undecenyl, n-dodecenyl, etc. C2-C4-alkenyl may be vinyl, propenyl, butenyl and isomers thereof, in particular vinyl, n-propenyl, isopropenyl, n-butenyl, 2-butenyl, tert-butenyl, n-pentenyl, isopentenyl, n-hexenyl, etc. C2-C4-alkenyl may be vinyl, propenyl, butenyl and isomers thereof, in particular vinyl, n-propenyl, 1-methylvinyl, n-butenyl, 1-methylpropenyl, 2-methylpropenyl or 1,1-dimethylvinyl.

[0047] The term "C6-C m "Aryl" refers to a monocyclic, bicyclic or higher ring aromatic hydrocarbon group containing 6-m carbon atoms, for example 6-10 carbon atoms. m As examples of the aryl group, there may be mentioned phenyl, tolyl, ethylphenyl, propylphenyl, butylphenyl, xylyl, methylethylphenyl, diethylphenyl, methylpropylphenyl and naphthyl, etc.; preferably phenyl or naphthyl, especially phenyl.

[0048] The term "C n -C m "Alkoxy" refers to n -C m Alkyl corresponding to the open chain C n -C m Any carbon atom of an alkane is bonded with an oxygen atom as a linker. n -C m Alkyl, such as C1-C12 Alkoxy, more preferably C1-C6 alkoxy, especially preferably C1-C4 alkoxy. C1-C6 alkoxy can be methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy and isomers thereof, in particular methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, 2-butoxy, tert-butoxy, n-pentoxy, isopentoxy, n-hexoxy, etc. C1-C4 alkoxy can be methoxy, ethoxy, propoxy, butoxy and isomers thereof, in particular methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy or tert-butoxy.

[0049] The term "C n -C m "Haloalkyl" refers to a C n -C m Alkyl, such as C1-C 12 Halogenated alkyl, preferably C1-C6 haloalkyl, particularly preferably C1-C4 haloalkyl. n -C m As examples of haloalkyl, there may be mentioned monochloromethyl, monochloroethyl, dichloroethyl, trichloroethyl, monochloropropyl, dichloromethylethyl, monochlorobutyl, dichloromethylpropyl, trichloromethylpropyl, monochloropentyl, dichloromethylbutyl, monochlorohexyl and isomers thereof, in particular 1-chloromethylethyl, 1,1-dichloromethylethyl, 1-chloromethylpropyl, 2-chloromethylpropyl, 1,1-dichloromethylpropyl, 1,2-dichloromethylpropyl, 2,2-dichloromethylpropyl, 1,1,2-trichloromethylpropyl, 1,2,2-trichloromethylpropyl. Methylpropyl, 1-chloromethylbutyl, 2-chloromethylbutyl, 3-chloromethylbutyl, 1-chloroethylpropyl, 1,1-dichloromethylbutyl, 1,2-dichloromethylbutyl, 1,3-dichloromethylbutyl, 2,2-dichloromethylbutyl, 2,3-dichloromethylbutyl, 3,3-dichloromethylbutyl, 1-chloromethylpentyl, 2-chloromethylpentyl, 3-chloromethylpentyl, 4-chloromethylpentyl, 1-chloroethylbutyl, 2-chloroethylbutyl, 1-chloroethyl-1-methylpropyl, 1-ethyl-2-chloromethylpropyl, etc.

[0050] The term "C n -C m "Haloalkoxy" refers to a C n -C m Alkoxy, such as C1-C 12 As C n -C mAs examples of haloalkoxy, there may be mentioned chloromethoxy, 2-chloroethoxy, 3-chloropropoxy, 4-chlorobutoxy, 5-chloropentyloxy, 6-chlorohexyloxy and isomers thereof, in particular chloromethoxy, 2-chloroethoxy, 3-chloro-n-propoxy, 2-chloro-isopropoxy, 4-chloro-n-butoxy, 3-chloro-sec-butoxy, 2-chloro-tert-butoxy, 5-chloro-n-pentyloxy, 4-chloro-isopentyloxy, 6-chloro-n-hexyloxy and the like.

[0051] The term "C n -C m "Hydroxyalkyl" refers to n -C m Alkyl corresponding to the open chain C n -C m Any carbon atom of an alkane has a hydroxyl group bonded to it. n -C m Alkyl, for example C1-C6 hydroxyalkyl, particularly preferably C1-C4 hydroxyalkyl, such as hydroxymethyl, hydroxyethyl, hydroxypropyl, hydroxybutyl, hydroxypentyl, hydroxyhexyl and isomers thereof, in particular hydroxymethyl, hydroxyethyl, hydroxy-n-propyl, hydroxyisopropyl, hydroxy-n-butyl, hydroxy-sec-butyl, hydroxy-tert-butyl, hydroxy-n-pentyl, hydroxy-n-hexyl and the like.

[0052] The term "C n -C m "Alkylene" means a branched or unbranched saturated hydrocarbylene radical having n, for example 1 to 10, preferably 1 to 6 and particularly preferably 1 to 4 carbon atoms, for example methylene, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene and isomers thereof, in particular methylene, ethylene, n-propylene, methylethylene, n-butylene, 1-methylpropylene, 2-methylpropylene, 1,1-dimethylethylene, n-pentylene, 1-methylbutylene, 1,1-dimethylpropylene, 1-ethylpropylene, 1,1-dimethylpropylene, 1,2-dimethylpropylene, n-hexylene, 1-methylpentylene, 1,1-dimethylbutylene. The C1-C6 alkylene group may be methylene, ethylene, propylene, butylene, pentylene, hexylene and isomers thereof, in particular methylene, ethylene, n-propylene, isopropylene, n-butylene, tert-butylene, n-pentylene, isopentylene, n-hexylene and the like. The C1-C4 alkylene group may be methylene, ethylene, propylene, butylene and isomers thereof, in particular methylene, ethylene, n-propylene, isopropylene, n-butylene, tert-butylene, n-pentylene, isopentylene, n-hexylene and the like.

[0053] The term "C n-C m The term "cycloalkylene" refers to a cycloalkylene radical having nm, for example 3 to 10, preferably 4 to 8, particularly preferably 5 to 6, carbon atoms, for example cyclopropylene, cyclobutylene, cyclopentylene, cyclohexylene, cycloheptylene, cyclooctylene, cyclononylene, cyclodecylene and isomers thereof, in particular 1,2-cyclopropylene, 1,2-cyclobutylene, 1,3-cyclobutylene, 1,2-cyclopentylene, 1,3-cyclopentylene. 1,2-cyclohexylene, 1,3-cyclohexylene, 1,4-cyclohexylene, 1-methyl-2,4-cyclohexylene, 1-methyl-2,6-cyclohexylene, 1,3-cycloheptylene, 1,4-cycloheptylene, 1,3-cyclooctylene, 1,4-cyclooctylene, 1,5-cyclooctylene, 1,3-cyclononylene, 1,4-cyclononylene, 1,5-cyclononylene, 1,3-cyclodecylene, The C4-C8 cycloalkylene group may be cyclobutylene, cyclopentylene, cyclohexylene, cycloheptylene, cyclooctylene and isomers thereof, in particular 1,2-cyclobutylene, 1,3-cyclobutylene, 1,2-cyclopentylene, 1,3-cyclopentylene, 1,2-cyclohexylene, 1,3-cyclohexylene, 1,4-cyclohexylene, 1-methyl-2,4 ...hexylene, 1,4-cyclohexylene, 1-methyl-2,4-cyclobutylene, 1,2-cyclopentylene, 1,3-cyclopentylene, 1,4-cyclohexylene, 1-methyl-2,4-cyclohexylene, 1,2-cyclopentylene, 1,3-cyclohexylene, 1,4-cyclohexylene, 1-methyl-2,4-cyclohexylene, 1,2-cyclopentylene, 1,3-cyclohexylene, 1,4-cyclohexylene, 1-methyl-2,4-cyclohexylene, 1,2-cyclopentylene, 1,3-cyclohexylene, 1,4-cyclohexylene, 1-methyl-2,4-cyclohexylene, 1,2-cyclopentylene, 1,2-cyclopentylene, 1,3-cyclohexylene, 1,4-cyclohexylene, 1-methyl-2,4-cyclohexylene, 1,2-cyclopentylene, 1,2-cyclopentylene, The C5-C6 cycloalkylene group may be cyclopentylene, cyclohexylene and isomers thereof, in particular 1,2-cyclopentylene, 1,3-cyclopentylene, 1,2-cyclohexylene, 1,3-cyclohexylene or 1,4-cyclohexylene.

[0054] The term "C n -C m "Cycloalkenyl" refers to a cycloalkenyl group having nm, for example 3-10, preferably 4-8, particularly preferably 5-6 carbon atoms and a C=C double bond, such as cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, cyclononenyl, cyclodecenyl and isomers thereof. C4-C8 cycloalkenyl may be cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl and isomers thereof. C5-C6 cycloalkenyl may be cyclopentenyl, cyclohexenyl and isomers thereof.

[0055] In the compounds of formula (I) of the present invention, R1, R2, R3, and R4 are the same or different and are usually independently C6-C 10 Aryl, C1-C 12 Alkyl, C1-C 12 Alkoxy, one or more independently selected from NR a C2-C 12 Alkyl or one or more independently selected from NRa C2-C 12 Alkoxy, where R a is H or C1-C4 alkyl, such as C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkylamino-C1-C6 alkyl, C1-C6 alkylthio-C1-C6 alkyl, C1-C6 alkoxy-C1-C6 alkoxy, C1-C6 alkylamino-C1-C6 alkylamino or C1-C6 alkylthio-C1-C6 alkylthio. Preferably, R1, R2, R3, and R4 are the same or different and independently C6-C 10 Aryl, C1-C6 alkyl, C1-C6 alkoxy or one or more independently selected from NR a , O, S non-adjacent heteroatom interval C2-C6 alkyl, wherein R a It is H or C1-C4 alkyl, such as C1-C3 alkoxy-C1-C3 alkyl, C1-C3 alkylamino-C1-C3 alkyl or C1-C3 alkylthio-C1-C3 alkyl. It is particularly preferred that R1, R2, R3, R4 are the same or different and independently phenyl, C1-C4 alkyl, C1-C4 alkoxy or one or more independently selected from NR a , O, S non-adjacent heteroatom interval C2-C4 alkyl, wherein R a is H or C1-C4-alkyl, for example C1-C2-alkoxy-C1-C2-alkyl, C1-C2-alkylamino-C1-C2-alkyl or C1-C2-alkylthio-C1-C2-alkyl. In particular, R1, R2, R3, R4 are identical or different and independently C1-C4-alkyl. For example, R1, R2, R3, R4 are identical or different and independently phenyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy or tert-butoxy.

[0056] In the compounds of the present invention, R5, R6, R7, R8 are the same or different and are usually independently H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 hydroxyalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy. Preferably, R5, R6, R7, R8 are the same or different and are independently H, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 hydroxyalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy. Particularly preferably, R5, R6, R7, R8 are the same or different and are independently H or C1-C4 alkyl. For example, R5, R6, R7, R8 are the same or different and are independently H, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, hydroxymethyl, hydroxyethyl, hydroxy-n-propyl, hydroxy-isopropyl, hydroxy-n-butyl, hydroxy-sec-butyl or hydroxy-tert-butyl.

[0057] In the compounds of the present invention, L1, L2, L3, and L4 are the same or different and are independently C2-C 10 Alkylene or C3-C 10 Preferably, L1, L2, L3, L4 are the same or different and are independently C2-C6 alkylene or C4-C8 cycloalkylene. Particularly preferably, L1, L2, L3, L4 are the same or different and are independently C2-C4 alkylene or C5-C6 cycloalkylene.

[0058] In some preferred embodiments of the present invention,

[0059] R1, R2, R3, R4 are the same or different and are independently C6-C 10 Aryl, C1-C6 alkyl, C1-C6 alkoxy or one or more independently selected from NR a , O, S non-adjacent heteroatom interval C2-C6 alkyl, wherein R a is H or C1-C4 alkyl; preferably, R2, R3, R4 are the same or different and independently phenyl, C1-C4 alkyl, C1-C4 alkoxy or one or more independently selected from NR a , O, S non-adjacent heteroatom interval C2-C4 alkyl, wherein R a is H or C1-C4 alkyl;

[0060] R5, R6, R7, R8 are the same or different and independently represent H, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 hydroxyalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy; and

[0061] L1, L2, L3, L4 are the same or different and are independently C2-C10 Alkylene or C3-C 10 Cycloalkylene.

[0062] In some preferred embodiments of the present invention,

[0063] R1, R2, R3, R4 are the same or different and are independently phenyl, C1-C4 alkyl, C1-C4 alkoxy or one or more independently selected from NR a , O, S non-adjacent heteroatom interval C2-C4 alkyl, wherein R a is H or C1-C4 alkyl; R5, R6, R7, R8 are the same or different and independently are H, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 hydroxyalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy; and L1, L2, L3, L4 are the same or different and independently are C2-C6 alkylene or C4-C8 cycloalkylene.

[0064] Preferably, R1, R2, R3, R4 are the same or different and are independently C1-C4 alkyl; R5, R6, R7, R8 are the same or different and are independently H or C1-C4 alkyl; and L1, L2, L3, L4 are the same or different and are independently C2-C4 alkylene or C5-C6 cycloalkylene.

[0065] In another embodiment of the present invention, the compound of formula (I) is a compound of formula (I-1):

[0066]

[0067] According to a second aspect of the present invention, there is provided a method for preparing a compound of formula (I) of the present invention, comprising reacting a compound of formula (II) with a compound of formula (III) to obtain a compound of formula (I):

[0068]

[0069] Where R a R5, R6, R7, R8 are independently as defined in any one of items 1 and 3-5, L is an alkenyl or cycloalkenyl group having 2 to 30 carbon atoms,

[0070]

[0071] wherein R1, R2, R3 and R4 are as defined for the compound of formula (I).

[0072] The silicon atom of the compound of formula (III) contains a hydrogen atom, and therefore, the compound of formula (III) can be referred to as a hydrogen-containing silicone oil. The compound of formula (III) can be synthesized according to conventional methods or can be obtained from commercial sources. The addition reaction of the hydrogen atom bonded to the silicon atom of the compound of formula (III) with the unsaturated carbon-carbon double bond in the compound of formula (II) belongs to a reaction type known in the art.

[0073] Generally speaking, the reaction is carried out in the presence of a catalyst. As a catalyst suitable for the reaction, a Karstedt catalyst or a Speier catalyst is generally used. The amount of the catalyst is also conventional. Generally speaking, based on the weight of the compound of formula (III), the amount of the catalyst is 2-500ppm, preferably 80-200ppm.

[0074] The reaction of the compound of formula (II) and the compound of formula (III) is usually carried out in a solvent. As the type of solvent, there is no particular restriction, as long as the compound of formula (III), the compound of formula (II) and the catalyst can be dissolved and do not participate in the reaction between the compound of formula (II) and the compound of formula (III), preferably the solvent is also conducive to the product, that is, the compound of formula (I) is precipitated. As the solvent, an organic solvent is usually used, preferably petroleum ether, dichloromethane, toluene or any mixture thereof. The amount of solvent is also conventional, and generally speaking, the amount of solvent is 2-20 times, preferably 8-15 times, of the total weight of the compound of formula (III) and the compound of formula (II).

[0075] Advantageously, the molar ratio of the compound of formula (II) to the compound of formula (III) is 4:1-6:1, preferably 4:1-4.5:1.

[0076] In order to achieve the above reaction, the compound of formula (III) and the catalyst are usually dissolved in a solvent and aged for a period of time, then contacted with the compound of formula (II), and then heated to the reaction temperature and maintained for a period of time to obtain the compound of formula (I).

[0077] Aging is usually carried out at an elevated temperature, usually at 40-70° C., preferably 45-60° C. The aging time is usually 20-60 minutes, preferably 30-50 minutes.

[0078] The reaction temperature between the compound of formula (II) and the compound of formula (III) is generally 80-110°C, preferably 85-100°C.

[0079] The reaction between the compound of formula (II) and the compound of formula (III) is usually maintained at the reaction temperature for 6 to 20 hours, preferably 10 to 16 hours.

[0080] Of course, the reaction can be advantageously carried out under stirring. After the reaction is complete, the compound of formula (I) is obtained by conventional post-treatment. The post-treatment generally includes filtering or centrifuging to remove solid impurities, rotary evaporation to remove the solvent, and reduced pressure distillation to further remove the solvent.

[0081] The compound of formula (I) of the present invention has good photopolymerization activity and can be quickly cured under the action of ultraviolet light; its addition can improve the surface hydrophobicity, heat resistance and tensile properties of the cured film.

[0082] According to the third aspect of the present invention, a photocurable composition is provided, which comprises the compound of formula (I) of the present invention as a polymerizable monomer. In addition to the compound of formula (I) of the present invention, the photocurable composition may also comprise a cationic photoinitiator for ring-opening polymerization (a photoinitiator capable of initiating cationic polymerization) and optionally other monomers or oligomers containing cationic photocurable groups such as vinyl ether double bonds, alicyclic epoxy groups or oxacycloalkyl groups, such as 3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexylcarboxylate (E4221) or 4-vinyl epoxycyclohexane (VOH). The photocurable composition of the present invention may be a photocurable coating composition, an adhesive composition, a photocurable ink composition or a photoresist composition. After the composition is cured, the obtained cured product has good tensile properties, excellent hydrophobic properties and good heat resistance.

[0083] As photoinitiators for ring-opening polymerization, iodonium salts and sulfonium salts are commonly used. Advantageously, the iodonium salt photoinitiator and sulfonium salt photoinitiator have the following general formulas (A) and (B), respectively:

[0084]

[0085] in

[0086] R a , R b , R c , R d and R e Each independently is an unsubstituted C6-C 10 Aryl, or is selected from halogen, nitro, carbonyl, C1-C 12 Alkyl, C1-C 12 C6-C substituted with alkoxy, phenylthio, phenyl and substituted phenyl 10 Aryl, preferably phenyl or naphthyl, or phenyl or naphthyl substituted by substituents selected from halogen, nitro, C1-C6 alkyl and substituted phenyl, wherein the substituted phenyl comprises one or more substituents selected from halogen, nitro, C1-C6 alkyl and C1-C6 alkoxy; and

[0087] Y and Z are non-nucleophilic anions such as triflate, toluenesulfonate, C1-C6 carboxylate, BF4 - 、ClO4 - PF6 - 、AsF6 - or SbF6 - .

[0088] For example, as the photoinitiator, one or more selected from the group consisting of 4-(phenylthio)phenyl·diphenylsulfonium hexafluorophosphate, 4-(phenylthio)phenyl·diphenylsulfonium hexafluoroantimonate, bis(4-(diphenylsulfonium)phenyl)sulfide bishexafluorophosphate, bis(4-(diphenylsulfonium)phenyl)sulfide bishexafluoroantimonate, 10-(4-biphenyl)-2-isopropylthioxanthone-10-sulfonium hexafluorophosphate, 10-(4-biphenyl)-2-isopropylthioxanthone-10-sulfonium hexafluorophosphate, 10-(4-biphenyl)-2-isopropylthioxanthone-10-sulfonium Hexafluoroantimonate, diphenyliodonium hexafluorophosphate (810), 4-octyloxydiphenyliodonium hexafluorophosphate, 4-octyloxydiphenyliodonium hexafluoroantimonate, 4-isobutylphenyl·4'-methylphenyliodonium hexafluorophosphate, 4-isobutylphenyl·4'-methylphenyliodonium hexafluoroantimonate, bis(4-dodecylbenzene)iodonium hexafluoroantimonate, bis(4-dodecylbenzene)iodonium hexafluorophosphate, bis(4-tert-butylbenzene)iodonium hexafluorophosphate or bis(4-tert-butylbenzene)iodonium hexafluoroantimonate.

[0089] For the purposes of the present invention, the amount of photoinitiator used is conventional. Based on the total amount of photopolymerizable monomers, the content of photoinitiator is usually 0.1-5 mol%, preferably 0.5-2 mol%.

[0090] The photocurable composition of the present invention may further contain a sensitizer. As a sensitizer, for example, benzophenone and its derivatives such as 4-(4-methylphenylthio)benzophenone or 4,4'-di(diethylamino)benzophenone, thioxanthone and its derivatives such as 2-isopropylthioxanthone, anthraquinone and its derivatives such as 2-ethylanthraquinone, coumarin derivatives such as 5,7-dimethoxy-3-(4-dodecylbenzoyl)coumarin, camphorquinone, phenothiazine and its derivatives, 3-(aroylmethylene)thiazoline, rhodanine and its derivatives, eosin, rhodamine, acridine, anthocyanin, merocyanine dyes may be mentioned; preferably benzophenone and its derivatives, thioxanthone and its derivatives, anthraquinone and its derivatives, coumarin and its derivatives, and particularly preferably 2-isopropylthioxanthone.

[0091] For the purpose of the present invention, the amount of sensitizer used is conventional. The content of sensitizer is usually 0.1-5 mol%, preferably 0.3-1 mol%, based on the total amount of photopolymerizable monomers.

[0092] According to a fourth aspect of the present invention, there is provided a photocurable material obtained by photocuring the photocurable composition of the present invention. The photocuring conditions are not particularly limited as long as the photocurable composition of the present invention can be photocured. The photocurable material has the advantages of good tensile properties, excellent hydrophobic properties and good heat resistance due to the monomer units derived from the compound of formula (I) of the present invention.

[0093] According to the last aspect of the present invention, there is provided the use of the compound of formula (I) as a photocurable monomer in the field of photocurable materials.

[0094] The present invention is further described in detail below in conjunction with specific embodiments. In this application specification, unless otherwise clearly stated, all parts and percentages are based on weight.

[0095] Example

[0096] Unless otherwise specified, the experimental methods used in the following examples are conventional methods.

[0097] Unless otherwise specified, the materials and reagents used in the following examples can be obtained from commercial sources.

[0098] Toluene: CR Beijing Chemical Plant

[0099] Tetramethylcyclotetrasiloxane (D4H): AR Bid Pharmaceutical

[0100] 4-Vinylcyclohexene oxide (VOH): AR Anaiji Chemical

[0101] 1,3-Divinyl-1,1,3,3-tetramethyldisiloxane platinum (0) (Karstedt Catalyst): AR Bid Pharmaceuticals Diphenyliodonium hexafluorophosphate (810): AR Shanghai Aladdin Biochemical Technology Co., Ltd. 2-Isopropylthioxanthone (ITX): AR Shanghai Aladdin Biochemical Technology Co., Ltd.

[0102] 3,4-Epoxycyclohexylmethyl 3,4-epoxycyclohexylcarboxylate (E4221): AR Bid Pharmaceuticals

[0103] Example 1

[0104] In a three-necked flask equipped with a temperature probe and a reflux condenser, 5 mmol of hydrogenated silicone oil (tetramethylcyclotetrasiloxane, corresponding to the compound of formula (III), wherein R1, R2, R3, and R4 are methyl groups) and 0.317 g of 100 ppm Karstedt catalyst were dissolved in 100 ml of anhydrous toluene, and then the temperature was raised to 60°C and maintained for 40 min. Then 22 mmol of compound (II) (where R aThe mixture was heated to 90°C and kept under stirring for 12 hours. The solid impurities were removed by centrifugation, and the solution was evaporated at 45°C and 0.1 MPa by rotary evaporation. The obtained solution was then distilled under reduced pressure at 300 Pa and 40°C to obtain the product. The product was identified as compound (I-1) by nuclear magnetic hydrogen spectrum characterization with a yield of 72%, hereinafter referred to as QOX-Si.

[0105]

[0106] QOX-Si: 1 H NMR (400 MHz, chloroform-d) δ 3.87 (dd, J = 175.8, 12.5 Hz, 16H),

[0107] 3.51(d,J=12.5Hz,4H),3.45–3.24(m,12H),1.83–1.51(m,16H),0.84(dt,J=13.7,7.4Hz,20H),-0.04(s,12H).

[0108] Example 2

[0109] The purpose of this example is to illustrate the photopolymerization performance of the compound of the present invention. The preparation process of the photocurable composition is as follows:

[0110] Weigh X1 mol of the above compound (I-1), X2 mol of E4221 (3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexylcarboxylate), X3 mol of VOH (4-vinyl epoxycyclohexane), X4 mol of photoinitiator diphenyliodonium hexafluorophosphate (810) and X5 mol of sensitizer 2-isopropylthioxanthone (ITX) into a brown bottle and stir evenly, and store in the dark. Taking the photocurable composition QOX-Si-3.0% as an example, the molar ratio of each component is: compound (I-1) (X1): E4221 (X2): VOH (X3): 810 (X4): ITX (X5) = 3: 50: 50: 1: 0.5 (all molar ratios). The molar percentage X1 of the compound (I-1) of the present invention (ie, QOX-Si) in each photopolymerization system is shown in Table 1 below. As mentioned above, X2+X3 is fixed to 100 and X2:X3=1:1, and X4 and X5 remain unchanged.

[0111] A mixture of diphenyliodonium hexafluorophosphate (810) and 2-isopropylthioxanthone (ITX, sensitizer) in a molar ratio of 2:1 was used as the photoinitiator system. The photopolymerization kinetics in the presence of compound (I-1) were tested by real-time infrared (RT-IR) method (real-time infrared spectrometer: Nicolet 5700, Thermo Electron, USA), and the effects of each on the photopolymerization performance of the E4221 / VOH system at different contents were investigated. The vibration absorption peak of the COC of the three-membered oxygen heterocycle of the monomer E4221 and VOH used is located at 750cm -1 The vibration absorption peak of the COC of the four-membered oxygen heterocycle of the compound (I-1) as a polymerization monomer is 980 cm -1 The photocurable liquid composed of monomers and photoinitiators is evenly applied on the potassium bromide salt sheet (a little photocurable liquid is dipped into a thin tube, dotted on the potassium bromide salt sheet, and then spread evenly), and the liquid sample is irradiated for 900s with a high-pressure mercury lamp, where the main emission wavelength of the mercury lamp is 365nm and it is equipped with an optical fiber with a diameter of 5mm. Either end of the optical fiber is 10cm away from the test sample, and the irradiation intensity is 20mW cm -2 . By measuring at 750cm -1 and 980cm -1 The change in the COC bond peak area at the bottom characterizes the real-time conversion rate and polymerization rate of different epoxy groups, namely monomers.

[0112] The results of the photocurable compositions containing compound (I-1) (i.e., QOX-Si) are as follows: Figure 1-2 As shown in Table 1 (in the figure and the following table, QOX-Si-3.0% is taken as an example, which means that X1 in the formula is 3.0 mol%). The results show that the addition of compound (I-1) can significantly improve the conversion rate and conversion rate of the monomers in the E4221 / VOH system. In addition, only a small amount of compound (I-1) (1.5-9 mol%) can significantly increase the conversion rate of alicyclic epoxy, and its maximum conversion rate is even as high as 69%. In addition, by Figure 2 It can be seen that the conversion rate of compound (I-1) itself is significantly increased. Therefore, the compound of the present invention can improve the photopolymerization performance of the monomer of the E4221 / VOH system and the compound of the present invention itself has excellent photopolymerization activity.

[0113] Table 1: Monomer conversion rate at 900 s of the photocurable composition using compound (I-1) (QOX-Si)

[0114]

[0115]

[0116] Example 3

[0117] The purpose of this example is to illustrate that the compound of the present invention can improve the surface hydrophobicity of the photocured film.

[0118] Weigh X1 mol of the above compound (I-1) (i.e., QOX-Si), X2 mol of E4221, X3 mol of VOH, X4 mol of the photoinitiator diphenyliodonium hexafluorophosphate (810) and X5 mol of the sensitizer 2-isopropylthioxanthone (ITX) into a brown bottle and stir evenly. Keep away from light. The molar ratio of each component in the formula is: monomer (X1): E4221 (X2): VOH (X3): 810 (X4): ITX (X5) = 9 (X1): 50: 50: 1: 0.5. Add the stirred photosensitive liquid into a 6mm×8mm×70mm polytetrafluoroethylene mold, and then place the mold under a mercury lamp for irradiation (wavelength 365nm, light intensity 60mW cm -2 ), and after irradiation for 900 s, the cured film was taken out and the water contact angle test was performed.

[0119] The surface hydrophobicity of the photocured film was characterized by using a DSA25 water contact angle tester at a test temperature of 25°C. At the same time, a blank E4221 / VOH cured film was prepared using the same method as a reference. The results of the reference and the presence of compound (I-1) are shown in Figure 3 .

[0120] Depend on Figure 3 It can be seen that when the E4221 / VOH polymerization system does not add the compound of the present invention, the water contact angle of the cured film is 54.3°, and after the additional addition of compound (I-1), the water contact angle of the cured film is significantly improved. Therefore, the compound of the present invention can significantly improve the surface hydrophobicity of the cured film.

[0121] Example 4

[0122] The cured films were prepared in the presence of compound (I-1) in exactly the same manner as described in Example 3. The heat resistance of each photocured film was then determined using a thermogravimetric analyzer (DTG-60AH, Shimadzu Enterprise Management (China) Co., Ltd.). The test conditions were: under nitrogen protection, temperature range 25-600°C, heating rate 10°C / min. At the same time, a blank E4221 / VOH cured film was prepared using the same method as a reference. The results are shown in Tables 2 and Figure 4 .

[0123] From Table 2 and Figure 4 It can be seen that after adding compound (I-1), the initial decomposition temperature (T 5％ ) and maximum thermal weight loss temperature (T max) is significantly improved, so the heat resistance is significantly improved.

[0124] Table 2: Thermogravimetric data of photocured films using compound (I-1) (i.e., QOX-Si)

[0125] system <![CDATA[T 5％ (℃)]]> <![CDATA[T max (℃)]]> E4221 / VOH 197 385 QOX-Si-1.5% 238 404 QOX-Si-3% 254 408 QOX-Si-4.5% 278 411 QOX-Si-6% 296 413 QOX-Si-7.5% 304 418 QOX-Si-9% 302 420

[0126] Example 5

[0127] The purpose of this example is to illustrate that the compounds of the present invention can improve the tensile properties of photocured films.

[0128] The respective cured films in the presence of compound (I-1) were prepared in exactly the same manner as described in Example 3. Then, the tensile properties of the photocured films were tested using an electronic universal testing machine (E44.304, MTS Industrial Systems (China) Co., Ltd.) in accordance with the international standard ISO 1184-1983 "Determination of tensile properties of plastic films". The test temperature was 25°C, the humidity was 60%, and the test speed was 1 mm / min. At the same time, a blank E4221 / VOH cured film was prepared using the same method as a reference. The results are shown in Tables 3 and Figure 5 .

[0129] From Table 3 and Figure 5 It can be seen that the tensile strength of the pure E4221 / VOH photocured film is 0.96 MPa and the elongation at break is 6.21%. After the additional addition of compound (I-1), the tensile strength of the photocured film is significantly improved. Therefore, the compound of the present invention can significantly improve the tensile properties of the cured film.

[0130] Table 3: Tensile performance data of photocured films using compound (I-1) (i.e., QOX-Si)

[0131] system Tensile strength(MPa) Elongation at break (%) E4221 / VOH 0.96 6.21 QOX-Si-1.5% 3.98 5.32 QOX-Si-3% 4.88 4.36 QOX-Si-4.5% 5.32 3.96 QOX-Si-6% 5.98 3.14 QOX-Si-7.5% 6.12 2.56 QOX-Si-9% 6.06 2.23

Claims

1. Compound of formula (I): Where R 1 , R 2 , R 3 , R 4 are the same or different and are independently an organic group having 1 to 12 carbon atoms; 5 , R 6 , R 7 , R 8 are the same or different and are independently H, halogen, C 1 -C 6 Alkyl, C 1 -C 6 Haloalkyl, C 1 -C 6 Hydroxyalkyl, C 1 -C 6 Alkoxy or C 1 -C 6 Haloalkoxy; and L 1 , L 2 , L 3 , L 4 The same or different and independently are linking groups having 2 to 30 carbon atoms.

2. The compound of formula (I) according to claim 1, wherein R 1 , R 2 , R 3 , R 4 The same or different and independently C 6 -C 10 Aryl, C 1 -C 12 Alkyl, C 1 -C 12 Alkoxy, one or more independently selected from NR a C, O, S separated by non-adjacent heteroatoms 2 -C 12 Alkyl or one or more independently selected from NR a C, O, S separated by non-adjacent heteroatoms 2 -C 12 Alkoxy, where R a H or C 1 -C 4 alkyl.

3. The compound of formula (I) according to claim 1, wherein R 1 , R 2 , R 3 , R 4 The same or different and independently C 6 -C 10 Aryl, C 1 -C 6 Alkyl, C 1 -C 6 Alkoxy or one or more independently selected from NR a C, O, S separated by non-adjacent heteroatoms 2 -C 6 Alkyl, where R a H or C 1 -C 4 Alkyl; preferably, R 1 , R 2 , R 3 , R 4 The same or different and independently phenyl, C 1 -C 4 Alkyl, C 1 -C 4 Alkoxy or one or more independently selected from NR a C, O, S separated by non-adjacent heteroatoms 2 -C 4 Alkyl, where R a H or C 1 -C 4 Alkyl; and / or R 5 , R 6 , R 7 , R 8 are the same or different and are independently H, halogen, C 1 -C 4 Alkyl, C 1 -C 4 Haloalkyl, C 1 -C 4 Hydroxyalkyl, C 1 -C 4 Alkoxy or C 1 -C 4 haloalkoxy; and / or L 1 , L 2 , L 3 , L 4 The same or different and independently C 2 -C 10 Alkylene or C 3 -C 10 Cycloalkylene.

4. The compound of formula (I) according to claim 1, wherein R 1 , R 2 , R 3 , R 4 The same or different and independently phenyl, C 1 -C 4 Alkyl, C 1 -C 4 Alkoxy or one or more independently selected from NR a C, O, S separated by non-adjacent heteroatoms 2 -C 4 Alkyl, where R a H or C 1 -C 4 Alkyl; R 5 , R 6 , R 7 , R 8 are the same or different and are independently H, halogen, C 1 -C 4 Alkyl, C 1 -C 4 Haloalkyl, C 1 -C 4 Hydroxyalkyl, C 1 -C 4 Alkoxy or C 1 -C 4 Haloalkoxy; and L 1 , L 2 , L 3 , L 4 The same or different and independently C 2 -C 6 Alkylene or C 4 -C 8 Cycloalkylene; Preferably, R 1 , R 2 , R 3 , R 4 The same or different and independently C 1 -C 4 Alkyl; R 5 , R 6 , R 7 , R 8 are the same or different and are independently H or C 1 -C 4 Alkyl; L 1 , L 2 , L 3 , L 4 The same or different and independently C 2 -C 4 Alkylene or C 5 -C 6 Cycloalkylene.

5. The compound of formula (I) according to claim 1, which is a compound of formula (I-1):

6. A method for preparing a compound of formula (I) according to any one of claims 1 to 5, comprising reacting a compound of formula (II) with a compound of formula (III) to obtain a compound of formula (I): Where R a For R 5 , R 6 , R 7 , R 8 and independently as defined in any one of claims 1 and 3 to 5, L is an alkenyl or cycloalkenyl group having 2 to 30 carbon atoms, Where R 1 , R 2 , R 3 and R 4 As defined in any one of claims 1 to 5.

7. The method according to claim 6, wherein The reaction of the compound of formula (II) with the compound of formula (III) is carried out in the presence of a Karstedt catalyst or a Speier catalyst, preferably, the amount of the catalyst is 2-500 ppm, preferably 80-200 ppm, based on the weight of the compound of formula (III); and / or The molar ratio of the compound of formula (II) to the compound of formula (III) is 4:1-6:1, preferably 4:1-4.5:1; and / or The reaction between the compound of formula (II) and the compound of formula (III) is carried out at 80-110°C, preferably 85-100°C; and / or The reaction between the compound of formula (II) and the compound of formula (III) is carried out for 6 to 20 hours, preferably 10 to 16 hours.

8. A photocurable composition comprising the compound of formula (I) according to any one of claims 1 to 5 as a polymerizable monomer.

9. A photocurable material obtained from the photocurable composition according to claim 8.

10. Use of the compound of formula (I) according to any one of claims 1 to 5 in photocurable coatings, adhesives, inks and photoresists.

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