Photoinitiator, and preparation method therefor and use thereof

Abstract

Provided in the present application are a photoinitiator, and a preparation method therefor and the use thereof. The photoinitiator has a structure as represented by formula (I). When being applied to a photocuring system, the photoinitiator of the present application has good compatibility and a high initiation activity, does not migrate, has a high atom utilization rate, and can be applied to a hybrid system.

Description

A photoinitiator and a preparation method and application thereof TECHNICAL FIELD

[0001] The present application belongs to the field of organic chemistry, and particularly relates to a photoinitiator and a preparation method and application thereof. BACKGROUND

[0002] The benzoate and its derivatives have the characteristics of intramolecular ring-closing self-hydrogenation, and can initiate polymerization without adding amine hydrogen donors. The benzoate and its derivatives have been widely reported as photoinitiators (such as CN1649905A, CN101523289A, US4229274A). With the development of photoinitiator systems, double-substituted benzoate initiators with different parent groups have been developed (such as CN101175773A, CN109790137A, CN102640055A, etc.), which to some extent improve the initiation efficiency of the products, reduce the migration, and meet the application requirements.

[0003] However, the improvement of the initiation efficiency of the photoinitiator is always the goal pursued, and in addition, how to improve the solubility and migration after curing of the initiator product without affecting the initiation efficiency is also a direction that needs to be further broken through. SUMMARY

[0004] The following is a summary of the subject matter of the detailed description herein. This summary is not intended to limit the scope of the claims.

[0005] In view of the deficiencies of the prior art, the purpose of the present application is to provide a photoinitiator and a preparation method and application thereof. Compared with the traditional benzoate initiator, the initiator of the present application has good compatibility when applied to the photocuring system, high initiation activity, no migration, high atomic utilization rate, and can be applied to hybrid systems.

[0006] To achieve this purpose, the present application adopts the following technical solutions:

[0007] In one aspect, the present application provides a photoinitiator, which has a structure as shown in formula (I):

[0008] wherein,

[0009] X is O, S or a direct bond;

[0010] Y is O, S or CR9R 10 ;

[0011] R1, R2, R3, R4, R5, R6, R7 and R8 are independently hydrogen, halogen, hydroxyl, C1-C 18 alkyl, C5-C 10 cycloalkyl, C2-C 18alkyl, C2-C4alkenyl, C5-C7cycloalkyl, phenyl, C1-C4alkoxy, C5-C7cycloalkoxy, phenoxy, C1-C4alkylthio, C5-C7cycloalkylthio, phenylthio, di(C1-C4alkyl)amino, di(C5-C7cycloalkyl)amino, N-morpholino, N-piperidinyl, n is 1 or 2, q is 0 or 1, m is an integer from 1 to 4, R is H, methyl or ethyl, A is a direct bond or C1-C6straight or branched alkyl, X is C1-C 10 straight or branched alkyl, or a group in which at least one CH2of a C1-C 10 straight or branched alkyl is replaced in a discontinuous manner by oxygen or carbonyl, R' is H, C1-C6straight or branched alkyl, phenyl or C1-C6straight or branched alkyl substituted by phenyl, and at least one of R1, R2, R3, R4, R5, R6, R7and R8is a group in which n is 1 and q is 1;

[0012] R9and R 10 are independently hydrogen, C1-C 18 alkyl, C2-C 12 alkenyl, C5-C 10 cycloalkyl, phenyl, C1-C4alkylphenyl, R9and R 10 are independently present or form together with the C atom to which they are attached a 5-, 6- or 7-membered ring.

[0013] In one embodiment, the CR9R 10 is selected from -CH2-, wherein the wavy line represents the point of attachment of the group.

[0014] In one embodiment, the CR9R is selected from

[0015] In one embodiment, R1, R2, R3, R4, R5, R6, R7and R8are, with the exception of the group selected from independently selected from hydrogen, F, Cl, hydroxyl, methyl, ethyl, n-propyl, i-propyl, CH3-S-, methoxy, or the group.

[0016] Without limitation, formula (I) can optionally have the following structure:

[0017] ​​On the other hand, this application provides a method for preparing the photoinitiator as described above, the method comprising the following steps:

[0018] (1) The arylformyl ester shown in Formula III undergoes a hydrolysis reaction to give the arylformyl carboxylic acid shown in Formula II, as shown in the following reaction formula:

[0019] (2) The arylformoylformic acid shown in Formula II reacts with the epoxy compound shown in Formula IV to obtain the photoinitiator shown in Formula I, as shown in the following reaction formula:

[0020] Among them, at least one of R1”, R2”, R3”, R4”, R5”, R6”, R7” and R8” is selected from Other groups are independently hydrogen, halogen, hydroxyl, C1-C 18 Alkyl, C5-C 10 cycloalkyl, C2-C 18 Alkenyl, phenyl, C1-C4 alkoxy, C5-C7 cycloalkoxy, phenoxy, C1-C4 alkylthio, C5-C7 cycloalkylthio, phenylthio, di(C1-C4 alkyl)amino, di(C5-C7 cycloalkyl)amino, N-morpholinyl, N-piperidinyl n is 1 or 2, q is 0 or 1, m is an integer from 1 to 4, R is H, methyl or ethyl, and X is C1-C6. 10 Straight-chain or branched alkyl groups, or C1-C 10 The group consisting of at least one CH2 group in a straight-chain or branched alkyl group, wherein the CH2 group is discontinuously replaced by an oxygen or carbonyl group, and R' is a C1-C6 straight-chain or branched alkyl group substituted with H, C1-C6 straight-chain or branched alkyl group, phenyl group, or cycloalkyl group; at least one of R1', R2', R3', R4', R5', R6', R7', and R8' is selected from... Other groups are independently hydrogen, halogen, hydroxyl, C1-C 18 Alkyl, C5-C 10 cycloalkyl, C2-C 18 Alkenyl, phenyl, C1-C4 alkoxy, C5-C7 cycloalkoxy, phenoxy, C1-C4 alkylthio, C5-C7 cycloalkylthio, phenylthio, di(C1-C4 alkyl)amino, di(C5-C7 cycloalkyl)amino, N-morpholinyl, N-piperidinyl n is 1 or 2, q is 0 or 1, m is an integer from 1 to 4, R is H, methyl or ethyl, and X is C1-C6. 10 Straight-chain or branched alkyl groups, or C1-C 10a group in which at least one CH2in a straight-chain or branched alkyl group is replaced by -O- or -CO- in a discontinuous manner, R' is H, C1-C6 straight-chain or branched alkyl, phenyl or cycloalkyl-substituted C1-C6 straight-chain or branched alkyl.

[0021] That is, in the present application, different aryl formyl formate is hydrolyzed to obtain aryl formyl formic acid, and the aryl formyl formic acid and the epoxide compound further undergo esterification reaction to obtain the target product.

[0022] In one embodiment, the hydrolysis reaction of step (1) is carried out in the presence of an acidic catalyst.

[0023] In one embodiment, the acidic catalyst is selected from any one or a combination of at least two of concentrated sulfuric acid, polyphosphoric acid, hydrochloric acid, hydrobromic acid, phosphorus oxychloride, phosphorus pentachloride, dodecylbenzenesulfonic acid, p-toluenesulfonic acid or strong acid resin.

[0024] In one embodiment, the amount of the acidic catalyst added is 5%-15% of the weight of the aryl formyl formate of formula III, for example 5%, 7%, 9%, 10%, 12%, 14% or 15%.

[0025] In one embodiment, the solvent for the hydrolysis reaction of step (1) is water.

[0026] In one embodiment, the temperature for the hydrolysis reaction of step (1) is 90-100°C, for example 90°C, 93°C, 95°C, 98°C or 100°C, and the reaction time is 10-24h, for example 10h, 12h, 15h, 18h, 20h, 22h or 24h.

[0027] In one embodiment, the molar ratio of the aryl formyl formic acid of formula II to the epoxide compound of formula IV in step (2) is 1.0:2.5.

[0028] In the present application, the reaction of step (2) can or can not be carried out with a solvent, and the type of solvent used is not particularly limited as long as it can dissolve the reaction raw materials and has no adverse effect on the reaction. In one embodiment, the solvent for the reaction of step (2) is selected from any one or a combination of at least two of benzene, toluene, xylene or N,N-dimethylformamide.

[0029] In one embodiment, the temperature for the reaction of step (2) is 60-150°C, for example 60°C, 80°C, 90°C, 100°C, 110°C, 120°C, 130°C, 140°C or 150°C, and the reaction time is 2-8h, for example 2h, 3h, 4h, 5h, 6h, 7h or 8h.

[0030] In another aspect, the present application provides a photosensitive resin composition comprising the photoinitiator as described above.

[0031] Compared with the prior art, the present application has the following beneficial effects:

[0032] The photoinitiator of the present application has excellent solubility, can be applied not only to a free radical system but also to a hybrid system, has photosensitive effect, and has no migration after application.

[0033] Other aspects can be apparent after reading and understanding the detailed description. DETAILED DESCRIPTION

[0034] The technical solutions of the present application will be further described below through specific embodiments. Those skilled in the art should understand that the embodiments are only to help understand the present application and should not be regarded as specific limitations of the present application.

[0035] Preparation Example

[0036] Example 1

[0037] The present example provides a preparation method of compound (I), and the reaction flow thereof is shown as follows:

[0038] The specific steps include:

[0039] In a 2L four-necked flask, 53.6g of raw material 1(a) was dissolved in 600g of distilled water and heated in a water bath to keep above 95℃, then 3g of macroporous strong acid resin catalyst was added under stirring and continuously reacted for 10h, the reaction system was cooled in an ice water bath, and the crystalline product 1(b) 43.5g was obtained by filtration, with a yield of 87%.

[0040] In a 2L four-necked flask, 53.6g of raw material 1(a) was dissolved in 600g of distilled water and heated in a water bath to keep above 95℃, then 3g of macroporous strong acid resin catalyst was added under stirring and continuously reacted for 10h, the reaction system was cooled in an ice water bath, and the crystalline product 1(b) 43.5g was obtained by filtration, with a yield of 87%.

[0041] Characterization data:

[0042] 1H NMR (500 MHz, deuterated chloroform) δ 7.61 (dd, J = 7.5, 1.5 Hz, 1H), 7.52 (d, J = 1.5 Hz, 1H), 7.27 (td, J = 7.5, 1.5 Hz, 1H), 7.26 - 7.18 (m, 2H), 6.93 (td, J = 7.5, 1.6 Hz, 1H), 6.57 (dd, J = 7.5, 1.6 Hz, 1H), 4.20 - 4.11 (m, 6H), 4.00 (d, J = 12.3 Hz, 2H), 1.66 (q, J = 8.0 Hz, 2H), 0.85 (t, J = 8.0 Hz, 3H).

[0043] Example 2

[0044] This example provides a method for preparing compound (II), and the reaction flow for the preparation is shown as follows:

[0045] The specific steps include:

[0046] In a 2L four-necked flask, 74g of raw material 2(a) was dissolved in 800g of distilled water and heated in a water bath to maintain a temperature above 95°C, then 5g of macroporous strong acid resin catalyst was added under stirring, and the reaction was continuously carried out for 10h, then the reaction system was cooled in an ice water bath, and the crystal product 2(b) was obtained by filtration, with a yield of 89%.

[0047] In a 2L four-necked flask, 43g of 2(b) was added, 800ml of toluene was added, 3.4g of macroporous strong acid resin catalyst was added, and the temperature was raised to 60°C, then 51g of 2(c) was added dropwise, the reaction was carried out for 3.5h, and the reaction liquid was obtained, then the temperature was continuously raised to reflux, toluene was distilled off, the reaction liquid was added to 200ml of pure water, and solid was precipitated, then the mixture was stirred at 60°C for 30min, and the wet filter cake was obtained by filtration, then the wet filter cake was dried at 150mbar and 60°C to obtain light yellow solid (II) 78g, with a purity of 99.5% measured by HPLC, and a yield of 87%.

[0048] Characterization data:

[0049] 1H NMR (500 MHz, deuterated chloroform) δ 7.99 (dd, J = 4.6, 3.2 Hz, 4H), 7.83 (dd, J = 7.5, 1.4 Hz, 2H), 5.62 (dddd, J = 7.0, 5.9, 2.2, 1.2 Hz, 1H), 5.01 (p, J = 7.0 Hz, 1H), 4.35 (dd, J = 12.4, 6.8 Hz, 1H), 4.29 - 4.21 (m, 1H), 4.04 (d, J = 12.5 Hz, 4H), 3.75 - 3.64 (m, 8H), 3.66 - 3.59 (m, 2H), 3.63 - 3.56 (m, 2H), 3.50 (d, J = 12.5 Hz, 2H), 3.30 - 3.21 (m, 1H), 2.02 - 1.82 (m, 2H), 1.74 (dq, J = 12.3, 8.0 Hz, 2H), 1.57 (dq, J = 12.5, 8.0 Hz, 2H), 1.00 (td, J = 8.0, 1.5 Hz, 3H), 0.86 (t, J = 8.0 Hz, 6H).

[0050] Example 3

[0051] The present example provides a method for preparing compound (III), the reaction flow of which is shown as follows:

[0052] In a 2L four-necked flask, 73.2g of raw material 3(a) was dissolved in 800g of distilled water and heated in a water bath to maintain 95°C, then 5.12g of macroporous strong acid resin catalyst was added under stirring and continuously reacted for 10h. The reaction system was cooled in an ice water bath and filtered to obtain crystalline intermediate product 3(b) 60.84g with a yield of 90%.

[0053] In a 2L four-necked flask, 60g of 3(b) above, 800ml of toluene and 4.3g of macroporous strong acid resin catalyst were added and heated to 60°C, then 18.5g of 3(c) was added dropwise, and the reaction was completed after 3.5h to obtain a reaction liquid. The toluene was distilled out under reflux to obtain intermediate product 3(e) 65.5g with a yield of 83%.

[0054] In a 2L four-necked flask, 60g of 3(e) above, 600ml of toluene and 3g of macroporous strong acid resin catalyst were added and heated to 60°C, then 55g of 3(f) was added dropwise, and the reaction was completed after 3.5h to obtain a reaction liquid. The toluene was distilled out under reflux, and the reaction liquid was added to 200ml of pure water to precipitate solids. The mixture was stirred at 60°C for 30min, filtered to obtain a wet filter cake which was dried at 150mbar and 60°C to obtain light yellow solid (III) with a purity of 99.3% measured by HPLC and a yield of 85%.

[0055] Characterization data:

[0056] 1 H NMR (500 MHz, Chloroform-d) 7.99 (dd, J = 4.6, 3.2 Hz, 4H), 7.83 (dd, J = 7.5, 1.4 Hz, 2H), 5.62 (dddd, J = 7.0, 5.9, 2.2, 1.2 Hz, 1H), 5.01 (p, J = 7.0 Hz, 1H), 4.35 (dd, J = 12.4, 6.8 Hz, 1H), 4.29 - 4.21 (m, 1H), 4.04 (d, J = 12.5 Hz, 4H), 3.75 - 3.64 (m, 8H), 3.66 - 3.59 (m, 2H), 3.63 - 3.56 (m, 2H), 3.50 (d, J = 12.5 Hz, 2H), 3.30 - 3.21 (m, 1H), 2.02 - 1.82 (m, 2H), 1.74 (dq, J = 12.3, 8.0 Hz, 2H), 1.57 (dq, J = 12.5, 8.0 Hz, 2H), 1.00 (td, J = 8.0, 1.5 Hz, 3H), 0.86 (t, J = 8.0 Hz, 6H).

[0057] Examples 4-9

[0058] Referring to the method of Examples 1-3, the products 4-9 having the structures shown in Table 1 below were synthesized.

[0059] Table 1

[0060] Performance Evaluation

[0061] The application performance of the initiators of the present application was evaluated by formulating exemplary photocuring compositions (i.e., photosensitive resin compositions, mass parts).

[0062] Table 2-1 Radical system photocuring composition

[0063] Table 2-2 Radical system photocuring composition

[0064] Table 3-1 Hybrid system photocuring composition

[0065] Table 3-2 Hybrid system photocuring composition

[0066] E201: Bisphenol A epoxy acrylate (Changzhou Qiangli Electronic New Material Co., Ltd.)

[0067] ACMO: Acryloyl morpholine (Runao Chemical Industry)

[0068] TMPTA: Trimethylolpropane triacrylate

[0069] PEGDA: Polyethylene glycol diacrylate

[0070] BYK307: Flowing agent (BYK, Germany)

[0071] PAG30201: Bis(4-tert-butylphenyl) iodonium hexafluorophosphate (Changzhou Qiangli Electronic New Material Co., Ltd.)

[0072] PSS306: Sensitizer (Changzhou Qiangli Electronic New Material Co., Ltd.).

[0073] 2. Performance evaluation method

[0074] (1) Solubility evaluation

[0075] The solubility of initiator A: [4-(4-methoxyoxalyl-phenyl sulfanyl)-phenyl]-oxo-acetic acid methyl ester (IGM), initiator B: 2-(9,9-dimethoxyxanthene-2-yl)-2-oxo-acetic acid ethyl ester (IGM) and the photoinitiators (I)-(X) provided by Examples 1-11 in propylene glycol methyl ether acetate was tested respectively, and the results are shown in Table 1 below.

[0076] The test method for solubility is as follows: under the condition of room temperature 20±0.5℃, add an appropriate amount of 6110: TMPTA = 1:1 (mass ratio) photocuring monomer as solvent in a 250 mL glass beaker, take 0.5 g of the test sample and add it into the solvent, stir and mix for 20 min, and observe with the naked eye whether there is undissolved sample. If the solution is clear, continue to add 0.5 g of the sample to be tested, stir and mix for 20 min, and stop adding the sample until undissolved substances exist. Record the data and calculate the solubility of the sample according to the following formula:

[0077] Table 2

[0078] (2) Sensitivity evaluation

[0079] The photocuring composition was stirred and mixed under a yellow light lamp, and the material was taken and roll-coated on a PET template to form a coating film with a thickness of about 50 μm. The film was irradiated with a mercury lamp (100%, 1 m / min, 1140 mJ / cm 2 ), LED 385 nm (100%, 3 m / min, 2568 mJ / cm 2), LED 405 nm (100%, 3 m / min, 2568 mJ / cm 2 The curing of the compositions was observed after exposure, and evaluated according to the following criteria:

[0080] 1. Oil, no cure

[0081] 2. Surface oil, bottom layer cured

[0082] 3. Surface tack, heavy fingerprints after hand touch

[0083] 4. Essentially dry, slightly tacky after hand touch, light fingerprints

[0084] 5. Fully cured, smooth surface, no fingerprints after hand touch

[0085] The test results are shown in Tables 4 and 5:

[0086] Table 4 Test results of free radical system

[0087] Table 5 Test results of hybrid system

[0088] (3) Migration test

[0089] The initiators (I)-(X), initiator (1), and initiator (2) were respectively prepared into a 1 x 10 -5 mol / L solution with ethanol as the solvent. The maximum absorption wavelength and absorbance Al were determined by a UV 3010 ultraviolet spectrophotometer, and the molar extinction coefficient was calculated by formula (1): c = A / ε x b (1) R = 100 x c / c1 (2)

[0090] The formulations of Table 3-1 and Table 3-2 were evaluated for Example and Comparative Example 1, and 0.05 g of the cured film of the above light-cured composition was weighed and fully cured under a high-pressure mercury lamp, and was respectively immersed in 30 g of ethanol. After being placed at room temperature for 24 h, the same volume of the immersion liquid was taken and the absorbance A2 at the maximum absorption wavelength was measured by a UV spectrophotometer. The concentration of the light initiator migrated from the three cured films was calculated by formula (1), and the concentration value of the light initiator (1) was taken as a reference standard, and the relative migration rate of various light initiators was calculated by formula (2).

[0091] In the above formula, c is the relative concentration (mol / L), c1 is the relative concentration of the light initiator (1), A is the absorbance, ε is the molar absorption coefficient (L / mol-cm); b is the thickness of the sample cell (cm); R is the relative migration rate. The test results are shown in Table 6.

[0092] Table 6

[0093] Experiments show that the initiator of the present application can not only be applied to a free radical system, but also to a hybrid system, and has a long wavelength initiator effect and a low migration characteristic.

[0094] The applicant declares that the photoinitiator of the present application, the preparation method and the application thereof are illustrated by the above examples, but the present application is not limited to the above examples, i.e. it does not mean that the present application must rely on the above examples to be implemented. It should be understood by those skilled in the art that any improvement of the present application, equivalent replacement of each raw material of the product of the present application, addition of auxiliary ingredients, selection of specific modes, etc. fall within the protection scope and disclosure scope of the present application.

Claims

1. A photoinitiator having the structure of formula (I): ###0001### (I) wherein, X is O, S or a direct bond; Y is O, S or CR9R 10 ; R1, R2, R3, R4, R5, R6, R7, and R8 are independently hydrogen, halogen, hydroxyl, or C1-C. 18 Alkyl, C5-C 10 cycloalkyl, C2-C 18 Alkenyl, phenyl, C1-C4 alkoxy, C5-C7 cycloalkoxy, phenoxy, C1-C4 alkylthio, C5-C7 cycloalkylthio, phenylthio, di(C1-C4 alkyl)amino, di(C5-C7 cycloalkyl)amino, N-morpholinyl, N-piperidinyl n is 1 or 2, q is 0 or 1, m is an integer from 1 to 4, R is H, methyl or ethyl, A is a direct bond or a C1-C6 straight chain or branched alkyl group, X is a C1-C 10 straight chain or branched alkyl group, or a group in which at least one CH2in a C1-C 10 straight chain or branched alkyl group is replaced in a discontinuous manner by oxygen or carbonyl, R' is H, C1-C6 straight chain or branched alkyl, phenyl or cycloalkyl substituted C1-C6 straight chain or branched alkyl, and at least one of R1, R2, R3, R4, R5, R6, R7and R8is a group in which n is 1 and q is 1 group; R9and R 10 independently hydrogen, C1-C 18 alkyl, C2-C 12 alkenyl, C5-C 10 cycloalkyl, phenyl, C1-C4alkylphenyl, R9and R 10 are present independently or form together with the C atom to which they are attached a 5-, 6- or 7-membered ring.

2. The photoinitiator according to claim 1, wherein, said CR9R 10 selected from -CH2-, wherein the wavy line represents the point of attachment of the group.

3. The photoinitiator according to claim 1 or 2, wherein the selected from 4. The photoinitiator according to any one of claims 1 to 3, wherein, R1, R2, R3, R4, R5, R6, R7and R8are, with the exception of the group selected from independently from hydrogen, F, Cl, hydroxyl, methyl, ethyl, n-propyl, i-propyl, CH3-S-, methoxy, or the group .

5. The photoinitiator according to any one of claims 1 to 4, wherein, The photoinitiator is any one of the following compounds:

6. A method for preparing the photoinitiator according to any one of claims 1-5, comprising the following steps: (1) hydrolysis of an aryl formyl formate of Formula III to obtain an aryl formyl formate of Formula II, as shown in the following reaction formula: (2) reacting an aryl formyl carboxylic acid of formula II with an epoxide of formula IV to obtain a photoinitiator of formula I, as shown in the following reaction scheme: wherein at least one of R1", R2", R3", R4", R5", R6", R7", and R8" is selected from Other groups are independently hydrogen, halogen, hydroxyl, C1-C 18 Alkyl, C5-C 10 cycloalkyl, C2-C 18 Alkenyl, phenyl, C1-C4 alkoxy, C5-C7 cycloalkoxy, phenoxy, C1-C4 alkylthio, C5-C7 cycloalkylthio, phenylthio, di(C1-C4 alkyl)amino, di(C5-C7 cycloalkyl)amino, N-morpholinyl, N-piperidinyl n is 1 or 2, q is 0 or 1, m is an integer from 1 to 4, R is H, methyl or ethyl, A is a direct bond or a C1-C6 straight chain or branched alkyl group, X is a C1-C 10 straight chain or branched alkyl group, or a group in which at least one CH2in a C1-C 10 straight chain or branched alkyl group is replaced in a discontinuous manner by oxygen or carbonyl, R' is H, C1-C6 straight chain or branched alkyl, phenyl or C1-C6 straight chain or branched alkyl substituted by phenyl; at least one of R1', R2', R3', R4', R5', R6', R7' and R8' is selected from Other groups are independently hydrogen, halogen, hydroxyl, C1-C 18 Alkyl, C5-C 10 cycloalkyl, C2-C 18 Alkenyl, phenyl, C1-C4 alkoxy, C5-C7 cycloalkoxy, phenoxy, C1-C4 alkylthio, C5-C7 cycloalkylthio, phenylthio, di(C1-C4 alkyl)amino, di(C5-C7 cycloalkyl)amino, N-morpholinyl, N-piperidinyl n is 1 or 2, q is 0 or 1, m is an integer from 1 to 4, R is H, methyl or ethyl, A is a direct bond or a C1-C6 straight chain or branched alkyl group, X is a C1-C 10 straight chain or branched alkyl group, or a group in which at least one CH2in a C1-C 10 straight chain or branched alkyl group is replaced in a discontinuous manner by oxygen or carbonyl, R' is H, C1-C6 straight chain or branched alkyl, phenyl or cycloalkyl substituted C1-C6 straight chain or branched alkyl.

7. The production method according to claim 6, wherein The hydrolysis reaction in step (1) is carried out in the presence of an acidic catalyst; Optionally, the acidic catalyst is selected from any one or a combination of at least two of concentrated sulfuric acid, polyphosphoric acid, hydrochloric acid, hydrobromic acid, phosphorus oxychloride, phosphorus pentachloride, dodecylbenzenesulfonic acid, p-toluenesulfonic acid or a strong acid resin; Optionally, the acidic catalyst is added in an amount of 5-15% by weight of the aryl formyl formate of formula III; Optionally, the solvent for the hydrolysis reaction in step (1) is water; Optionally, the temperature for the hydrolysis reaction in step (1) is 90-100°C and the reaction time is 10-24h.

8. The production method according to claim 6 or 7, wherein The molar ratio of the aryl formyl formate of formula II to the epoxide compound of formula IV in step (2) is 1.0:2.0-2.

8.

9. The production process according to any one of claims 6 to 8, wherein, The solvent for the reaction in step (2) is selected from any one or a combination of at least two of benzene, toluene, xylene or N,N-dimethylformamide; Optionally, the temperature for the reaction in step (2) is 60-150°C and the reaction time is 2-8h.

10. A photosensitive resin composition comprising the photoinitiator according to any one of claims 1-5.

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