CN110105315A - Oxime ester compound and its preparation method and application containing aryl thioethers furans or aryl thioethers thiophene - Google Patents

Abstract

The present invention provides an oxime ester compound containing aryl sulfide furan or aryl sulfide thiophene and a preparation method and application thereof. In the oxime ester compound, R ₁ , R ₂ , R ₃ , R ₄ and R ₅ , R ₆ and R ₇ are independently selected from hydrogen, halogen atom, R, OR, SR, SOR, SO ₂ R, NRR', CH ₂ OH, CH ₂ OR, CH ₂ OCOR, CH ₂ SR, CH ₂ SCOR and CH ₂ NRR', R ₈ and R ₉ are respectively selected from C ₁ -C ₂₀ straight-chain alkyl or C ₁ -C ₂₀ branched-chain alkyl, C ₃ -C ₁₂ cycloalkyl, cycloalkylalkyl, cycloheteroalkyl Alkylalkyl, C ₆ -C ₁₂ aryl, alkylaryl; the present invention introduces heterocycles, including furan rings and thiophene rings, into the molecular structure, and the introduction of heteroatoms further provides lone pairs of electrons, making such The absorption spectrum of the molecule is further red-shifted compared with the benzene ring, which is more matched with the emission wavelength of the currently commercialized LED light source.

Description

Oxime ester compounds containing aryl sulfide furan or aryl sulfide thiophene and their preparation methods and applications

technical field

The invention belongs to the technical field of organic chemicals of new materials, in particular to a compound containing an oxime ester structure of an aryl sulfide heterocycle, more specifically an oxime ester containing an aryl sulfide furan or an aryl sulfide thiophene Compounds and methods for their preparation and use.

Background technique

Photoinitiator compounds are an important class of fine organic chemical materials. In the technical field of radiation curing using a mercury lamp or LED (ie Light-Emitting Diode) emitting ultraviolet light or visible light as a light source, the photoinitiator compound that can generate free radical active species under light irradiation conditions is a kind of photoinitiator compound that induces ethylenically unsaturated The system is the key species for efficient photopolymerization, so it is one of the important radiation curing formulation components. Light curing has many advantages such as energy saving, environmental protection, high efficiency and speed, and time-space controllability. It has been widely used in traditional fields such as coatings, inks, adhesives, and high-tech products such as 3D printing. Photosensitive resin formulations for photocuring usually contain photoinitiators, reactive diluents, oligomers and various auxiliaries. Among them, photoinitiators are the key components of photocuring formulations, and their activity directly affects the photocuring rate and degree of curing. and end product performance.

Compared with traditional UV light curing, LED light curing using light emitting diodes (LEDs) as light sources has significant advantages such as high energy utilization, small thermal effect, and no ozone generation. Traditional photoinitiators are mainly used for short-wavelength UV curing, which is difficult to match with LED light sources. Therefore, through reasonable molecular design and systematic structure-activity relationship research, a series of efficient LED photoinitiators have been developed. application prospects.

Aryl oxime esters or aryl ketone oxime esters are a class of photoinitiators with a wide range of uses. The famous oxime ester initiators OXE-01 and OXE-02 are the best representative commercial molecules. The molecular structure is shown below:

In view of the above technical challenges, it is still very necessary to invent a photoinitiator that is sensitive to LED light sources, has high sensitivity, high stability, and is easy to prepare in the field of photocuring. In addition, the synthesis step of such an initiator should be The method has the advantages of simplicity, low cost, environmental protection in the synthesis process, less three wastes and the like. With the continuous improvement of people's requirements for environmental protection, production safety awareness and labor insurance, as well as the continuous development of photopolymerization technology, LED, LDI and other low energy consumption, high safety and environmentally friendly exposure light sources have become the technical application and a trend of development.

SUMMARY OF THE INVENTION

In view of the deficiencies in the prior art, the primary purpose of the present invention is to provide an oxime ester compound containing aryl sulfide furan or an oxime ester compound containing aryl sulfide thiophene.

The second object of the present invention is to provide a preparation method of the above-mentioned oxime ester compound.

The third object of the present invention is to provide the use of the above-mentioned oxime ester compound.

In order to achieve the above object, the solution of the present invention is:

A kind of oxime ester compound containing aryl sulfide furan or aryl sulfide thiophene, its general formula is as follows:

Wherein, R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ and R ₇ are respectively selected from hydrogen, halogen atom, R, OR, SR, SOR, SO ₂ R, NRR', CH ₂ OH, CH _One or more of 2OR, _CH2OCOR , _CH2SR , _CH2SCOR and _CH2NRR '.

R and R' are respectively selected from one or more of C ₁ -C ₂₄ straight chain alkyl, C ₁ -C ₂₄ branched chain alkyl and -C ₆ -C ₂₄ aryl group, R and R' may be the same or may different.

Specifically, fluorine atoms can be used to replace hydrogen atoms in the R and R' structures to form a fluorocarbon chain structure; the R and R' structures can contain 1-6 discontinuous S, O, N elements, that is, the R and R' structures It not only contains carbon chains, but also heteroatoms can be introduced into the carbon chains to form such as C-C-O-C-C, C-C-S-C-C, etc., that is, no longer only pure carbon chains can be used as substituents, carbon chains containing heteroatoms can also be used as substituents.

When R and R' in NRR' coexist, they can form a 3-6 membered ring structure, such as cyclobutylamino, cyclopentylamino, cyclohexylamino, etc.

R ₈ and R ₉ are respectively selected from C ₁ -C ₂₀ straight chain alkyl, C ₁ -C ₂₀ branched chain alkyl, C ₃ -C ₁₂ cycloalkyl, cycloalkylalkyl, cycloheteroalkylalkyl, One or more of C ₆ -C ₁₂ aryl groups and alkylaryl groups; R ₈ and R ₉ can also be connected to form C ₆ -C ₂₄ cycloalkyl groups.

Further, cycloalkylalkyl is selected from Wherein, x=1-5, y=1-6.

Further, cycloheteroalkylalkyl is selected from Wherein, x=1-5, y=1-6, and z is selected from one or more of S, O, and N.

A kind of above-mentioned preparation method of the oxime ester compound containing aryl sulfide furan or aryl sulfide thiophene, it comprises the steps:

(1), the aryl thiophenol substituted with R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , and brominated furanone or brominated thiophenone are reacted under alkaline conditions to obtain aryl sulfide substituted Furanone (Ia) or aryl sulfide substituted thiophenone (Ia):

(2), aryl sulfide substituted furanone (I-a) or aryl sulfide substituted thiophenone (I-a) reacts with hydroxylamine hydrochloride under basic (preferably KOH) conditions to obtain oxime product (I-b):

(3), the oxime product (I-b) reacts with acid chloride or acid anhydride under alkaline action to obtain the oxime ester compound containing aryl sulfide furan or aryl sulfide thiophene:

Further, R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ and R ₇ are respectively selected from hydrogen, halogen atom, R, OR, SR, SOR, SO ₂ R, NRR′, CH ₂ OH, One or more of CH ₂ OR, CH ₂ OCOR, CH ₂ SR, CH ₂ SCOR and CH ₂ NRR'.

Wherein, R and R' are respectively selected from one or more of C ₁ -C ₂₄ straight-chain alkyl groups, C ₁ -C ₂₄ branched-chain alkyl groups and -C ₆ -C ₂₄ aryl groups.

R ₈ and R ₉ are respectively selected from C ₁ -C ₂₀ straight chain alkyl, C ₁ -C ₂₀ branched chain alkyl, C ₃ -C ₁₂ cycloalkyl, cycloalkylalkyl, cycloheteroalkylalkyl, One or more of C ₆ -C ₁₂ aryl groups and alkylaryl groups; R ₈ and R ₉ can also be connected to form C ₆ -C ₂₄ cycloalkyl groups.

Further, cycloalkylalkyl is selected from Wherein, x=1-5, y=1-6.

Further, cycloheteroalkylalkyl is selected from Wherein, x=1-5, y=1-6, and z is selected from one or more of S, O, and N.

Use of the above-mentioned oxime ester compound containing aryl sulfide furan or aryl sulfide thiophene as a radiation curing photoinitiator. Specifically, its use as a photoinitiator or other functional additive component, and as an intermediate or raw material or reagent in chemical synthesis.

Further, the light source for radiation curing the photoinitiator is selected from one or more of ultraviolet light and visible light.

Further, the light source of the radiation curing photoinitiator is selected from one or more of mercury lamps that can emit ultraviolet light and visible light, LED light sources, and LDI light sources.

Further, the radiation curing photoinitiator includes 0.01-30 parts by weight of an oxime ester compound containing aryl sulfide furan or aryl sulfide thiophene and 100 parts by weight of an ethylenic bond-containing (C═C) unsaturated compound.

Further, the radiation curing photoinitiator includes 0.5-10 parts by weight of an oxime ester compound containing aryl sulfide furan or aryl sulfide thiophene and 100 parts by weight of an ethylenic bond-containing (C═C) unsaturated compound.

In fact, in addition to oxime ester compounds containing aryl thioether furan or aryl thioether thiophene and ethylenically (C=C) unsaturated compounds, the radiation curing photoinitiator can also contain inorganic compounds according to actual needs. Any components such as fillers, organic fillers, colorants, other additives and solvents.

Among them, the colorant is selected from pigments or dyes.

Other additives include UV absorbers, light stabilizers, flame retardants, leveling agents or defoamers.

The specific steps are as follows: (1) Proportion raw materials according to the mass ratio of monomer and resin: photoinitiator: auxiliary agent 100: 0.5-1: 0-4.5; (2) stir to fully dissolve; (3) use different wavelengths Or the light source of different light intensity irradiates the polymerization system; (4) can use the method of online infrared to study the polymerization conversion rate through the change of its characteristic peak; Wherein: the light source in step (3) can be mercury lamp (high pressure, medium pressure and low pressure); ), and LEDs with emission wavelengths of 365-425nm, LDI light sources.

Further, the ethylenically unsaturated compound refers to a compound or mixture in which ethylenic bonds are cross-linked by radical polymerization.

Further, the ethylenically unsaturated compound is selected from monomers, oligomers or prepolymers, or a mixture or copolymer of the three, or an aqueous dispersion of the three.

Suitable free radical polymerizable monomers such as ethylenically containing polymerizable monomers include, but are not limited to (meth)acrylates, acrolein, olefins, conjugated dienes, styrene, maleic anhydride, fumaric anhydride, acetic acid Vinyl esters, vinylpyrrolidone, vinylimidazole, (meth)acrylic acid, (meth)acrylic acid derivatives such as (meth)acrylamides, vinyl halides and vinylidene halides, and the like.

Suitable olefinic prepolymers and oligomers include, but are not limited to, (meth)acryloyl-functional (meth)acrylic copolymers, urethane (meth)acrylates, polyesters (meth) Acrylates, unsaturated polyesters, polyether (meth)acrylates, silicone (meth)acrylates, epoxy (meth)acrylates, etc., and water-soluble or water-dispersible analogs of the above .

The above-mentioned olefin-containing monomers, oligomers, prepolymers, or copolymers are well known to those skilled in the art and are not particularly limited.

Exemplary compounds conforming to the structure of general formula (I) are listed below:

Owing to adopting the above-mentioned scheme, the beneficial effects of the present invention are:

The oxime ester compound containing aryl sulfide furan or the oxime ester compound containing aryl sulfide thiophene of the present invention is used as a radiation curing photoinitiator and is used in radiation curing formulation products, especially in UV-Vis-LED Excitable photo-curable coatings or inks and other applications. Oxime ester compounds represented by OXE-01 and OXE-02 have very good photo-initiating properties as a class of excellent free-radical photoinitiators. The present invention introduces heterocycles into the molecular structure, including furan rings and thiophenes. The introduction of ring, heteroatom further provides lone pair electrons, making the absorption spectrum of this type of molecule further red-shifted compared with the benzene ring, and more matching the emission wavelength of the current commercial LED light source. In addition, such molecules are simple in synthesis, green and environmentally friendly, and have low three wastes, making them a very promising class of photoinitiators.

Description of drawings

Fig. 1 is the general structural formula of the oxime ester compound containing aryl sulfide furan or aryl sulfide thiophene of the present invention.

Detailed ways

As shown in FIG. 1 , the present invention provides an oxime ester compound containing aryl sulfide furan or aryl sulfide thiophene, and a preparation method and application thereof.

The present invention will be further described below in conjunction with the examples.

Example 1:

Intermediate: Preparation of aryl sulfide substituted furanone or aryl sulfide substituted thiophenone:

Among them, under the protection of _N2 , brominated furanone or brominated thiophenone (10mmol), cuprous oxide (5mmol) and potassium hydroxide (10mmol) were dispersed in dimethylformamide (DMF, 0.2mol/ L), slowly add various substituted aryl thiophenols (10mmol), heat to 100-150°C, react for 3-10h, cool to room temperature, neutralize with 6N (equivalent) hydrochloric acid, extract with dichloromethane, anhydrous Dry with sodium sulfate, evaporate the solvent to dryness, recrystallize with ethanol, or purify by silica gel column chromatography. obtain the target product. The yield is 50-85% depending on the raw material.

Embodiment 2: the preparation process of the oxime ester compound (I)-1 containing aryl sulfide furan of this embodiment:

Thiophenol (10 mmol) was slowly added to 1-acetyl-4-bromofuran (10 mmol), cuprous oxide (5 mmol), potassium hydroxide (10 mmol), dispersed in 50 mL of DMF, heated to 130 ° C under nitrogen atmosphere , stirred for 3h, cooled to room temperature, added to 50mL of water, adjusted to neutrality with 6N (equivalent) hydrochloric acid, extracted with dichloromethane, recrystallized with ethanol, and the yield was 84%.

The ketone prepared in the previous step was dissolved in absolute ethanol (0.2 mol/L), 1.5 equivalents of hydroxylamine hydrochloride and 2 equivalents of sodium hydroxide were added, heated to reflux for 5 h, concentrated, poured into deionized water, and the precipitated solid was the product by suction filtration, Do not need to purify, directly carry out the next step reaction after drying _; in the dark room, under the protection of N gas, put (5mmol) oxime and 50mL anhydrous dichloromethane into the three-necked flask in turn, stir at room temperature for 5min and add 10mmol of triethyl ether amine, 5mmol of acetic anhydride was added dropwise, the dropwise addition was completed in about 30min, and the stirring was continued for 2h. The reaction system was added with 50 mL of deionized water, extracted with dichloromethane, washed with 2 mol/L HCl and 5% NaHCO ₃ aqueous solution, and adjusted to neutral pH; dried over anhydrous NaSO ₄ , and the solvent was distilled off under reduced pressure; Purified by column chromatography, the polarity of the eluent was selected as PE/EA=2:1, and finally a pale yellow solid compound was obtained with a total yield of 88%. HR-MS (C ₁₄ H ₁₃ NO ₃ S): m/e: 275.0616; experimental result: 276.1693 (M+H ⁺ ).

Embodiment 3: The preparation process of the oxime ester compound containing aryl sulfide furan or aryl sulfide thiophene of this embodiment:

(1) The obtained aryl sulfide substituted furanone or aryl sulfide substituted thiophenone was dissolved in an appropriate amount of absolute ethanol, a small amount of water, hydroxylamine hydrochloride (1.5 mol equiv.) and solid NaOH (2 mol equiv.) were added, heated to reflux for 5 h, poured into Into deionized water, the precipitate separated out by suction filtration to obtain the intermediate oxime product;

( ₂ ) Synthesis of target product: in a dark room, under the protection of N , in a three-necked flask, drop into (5mmol) oxime product, 50mL of anhydrous dichloromethane successively, add 10mmol of triethylamine after stirring at room temperature for 5min, and then dropwise 5mmol of acid anhydride or acid chloride was added, the dropwise addition was completed in about 30min, and the stirring was continued for 2h. The reaction system was added with 50 mL of deionized water, extracted with dichloromethane, washed with 2 mol/L HCl and 5% NaHCO ₃ aqueous solution, and adjusted to neutral pH; dried over anhydrous NaSO ₄ , and the solvent was distilled off under reduced pressure; After purification by column chromatography, the polarity of the eluent was selected as PE/EA=2:1, and finally a solid product was obtained with a total yield of 70-90%.

Characterization of the series:

(I)-2, overall yield 80%, HR-MS (C ₁₅ H ₁₅ NO ₃ S): m/e: 289.0773; experimental result: 290.0860 (M+H ⁺ ).

(I)-3, overall yield 83%, HR-MS (C ₁₆ H ₁₆ NO ₃ S): m/e: 302.0851; experimental result: 303.1939 (M+H ⁺ ).

(I)-4, overall yield 81%, HR-MS (C ₁₇ H ₁₉ NO ₃ S): m/e: 317.1086; experimental result: 318.1164 (M+H ⁺ ).

(I)-5, overall yield 77%, HR-MS (C ₁₈ H ₂₁ NO ₃ S): m/e: 331.1242; experimental result: 332.1320 (M+H ⁺ ).

(I)-6, overall yield 75%, HR-MS (C ₁₉ H ₂₂ NO ₃ S): m/e: 344.1320; experimental result: 345.1407 (M+H ⁺ ).

(I)-7, overall yield 82%, HR-MS (C ₁₉ H ₂₁ NO ₃ S): m/e: 343.1242; experimental result: 344.1330 (M+H ⁺ ).

(I)-8, overall yield 74%, HR-MS (C ₁₉ H ₁₅ NO ₃ S): m/e: 337.0773; experimental result: 338.0860 (M+H ⁺ ).

(I)-9, overall yield 83%, HR-MS (C ₂₀ H ₂₄ NO ₃ S): m/e: 358.1477; experimental result: 359.1564 (M+H ⁺ ).

(I)-10, overall yield 75%, HR-MS (C ₂₂ H ₂₈ NO ₃ S): m/e: 386.1790; experimental result: 387.1866 (M+H ⁺ ).

(I)-11, overall yield 82%, HR-MS (C ₂₃ H ₃₀ NO ₃ S): m/e: 400.1946; experimental result: 401.2023 (M+H ⁺ ).

(I)-12, overall yield 81%, HR-MS (C ₂₅ H ₂₆ NO ₃ S): m/e: 420.1633; experimental result: 421.1710 (M+H ⁺ ).

(I)-13, overall yield 80%, HR-MS (C ₂₅ H ₂₈ NO ₃ S): m/e: 422.1790; experimental result: 423.1877 (M+H ⁺ ).

(I)-14, overall yield 76%, HR-MS (C ₂₅ H ₂₆ NO ₃ S): m/e: 420.1633; experimental result: 421.1711 (M+H ⁺ ).

(I)-15, overall yield 80%, HR-MS (C ₂₅ H ₂₆ NO ₃ S): m/e: 420.1633; experimental result: 421.1710 (M+H ⁺ ).

(I)-16, overall yield 74%, HR-MS (C ₂₆ H ₂₈ NO ₃ S): m/e: 434.1790; experimental result: 435.166 (M+H ⁺ ).

(I)-17, overall yield 75%, HR-MS (C ₁₈ H ₂₁ NO ₂ S ₂ ): m/e: 347.1014; experimental result: 348.1092 (M+H ⁺ ).

(I)-18, overall yield 77%, HR-MS (C ₁₉ H ₂₂ NO ₂ S ₂ ): m/e: 360.1092; experimental result: 361.1168 (M+H ⁺ ).

(I)-19, overall yield 80%, HR-MS (C ₁₉ H ₂₁ NO ₂ S ₂ ): m/e: 359.1014; experimental result: 360.1091 (M+H ⁺ ).

(I)-20, overall yield 81%, HR-MS (C ₁₉ H ₁₅ NO ₂ S ₂ ): m/e: 353.0544; experimental result: 354.0622 (M+H ⁺ ).

(I)-21, overall yield 84%, HR-MS (C ₂₀ H ₂₄ NO ₂ S ₂ ): m/e: 374.1248; experimental result: 375.1335 (M+H ⁺ ).

(I)-22, overall yield 78%, HR-MS (C ₂₂ H ₂₈ NO ₂ S ₂ ): m/e: 402.1561; experimental result: 403.1638 (M+H ⁺ ).

(I)-23, overall yield 81%, HR-MS (C ₂₃ H ₃₀ NO ₂ S ₂ ): m/e: 416.1718; experimental result: 417.1796 (M+H ⁺ ).

(I)-24, overall yield 76%, HR-MS (C ₂₅ H ₂₆ NO ₂ S ₂ ): m/e: 436.1405; experimental result: 437.1482 (M+H ⁺ ).

(I)-25, overall yield 79%, HR-MS (C ₂₄ H ₂₄ NO ₂ S ₂ ): m/e: 422.1248; experimental result: 423.1335 (M+H ⁺ ).

(I)-26, overall yield 77%, HR-MS (C ₂₅ H ₂₆ NO ₂ S ₂ ): m/e: 436.1405; experimental result: 437.1482 (M+H ⁺ ).

(I)-27, overall yield 81%, HR-MS (C ₂₅ H ₂₆ NO ₂ S ₂ ): m/e: 436.1405; experimental result: 437.1483 (M+H ⁺ ).

(I)-28, overall yield 75%, HR-MS (C ₂₆ H ₂₈ NO ₂ S ₂ ): m/e: 450.1561; experimental result: 451.1639 (M+H ⁺ ).

<Experiment>

The following experiments were carried out with the products of the above embodiments.

<Experiment 1>

Film Polymerization:

The light-curing test samples were prepared according to the following weight percentages: epoxy acrylate: 28 parts; polyester acrylate: 32 parts; hexanediol diacrylate: 6 parts; pentaerythritol triacrylate: 24 parts; titanium dioxide dye: 16 parts parts; photoinitiator of selected examples: 4 parts.

A part of the above mixture was thoroughly ground and then coated on a white ABS substrate to form a layer of about 20 μm in the air. The samples were irradiated with a 365nm and 385nm LED curing tester (Waguang Tongsheng, Guangzhou) at a distance of 2 cm from the sample, and the conveyor speed was 20 m/min. Scratch the hair with finger pressure to determine the complete curing of the coating. In the compounds of the above examples, the photoinitiator initiates the complete curing of the film layer, especially when the volume of R ₈ is larger, it shows better initiation performance.

<Experiment 2>

Thick Film Polymerization:

The formula is the same as in experiment 1.

A part of the above mixture was thoroughly ground and coated on a white ABS substrate to form a layer of about 200 μm in the air. The samples were irradiated with a 365nm and 385nm LED curing tester (Waguang Tongsheng, Guangzhou) at a distance of 2 cm from the sample, and the conveyor speed was 10 m/min. Press and scratch the hair to determine the complete curing of the coating. The molecular structure in the above-mentioned example (2), especially the photoinitiator with a larger R ₈ substituent, all induced the complete curing of the film layer, showing good photoinitiator performance.

The foregoing description of the embodiments is provided to facilitate understanding and use of the present invention by those of ordinary skill in the art. It will be apparent to those skilled in the art that various modifications to these embodiments can be readily made, and the general principles described herein can be applied to other embodiments without inventive effort. Therefore, the present invention is not limited to the above-described embodiments. Improvements and modifications made by those skilled in the art according to the principles of the present invention without departing from the scope of the present invention should all fall within the protection scope of the present invention.

Claims (9)

1. an oxime ester compound containing aryl sulfide furan or aryl sulfide thiophene, is characterized in that: its general formula is as follows: Wherein, R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ and R ₇ are respectively selected from hydrogen, halogen atom, R, OR, SR, SOR, SO ₂ R, NRR', CH ₂ OH, CH More than one of ₂ OR, CH ₂ OCOR, CH ₂ SR, CH ₂ SCOR and CH ₂ NRR'; R and R' are respectively selected from one or more of C ₁ -C ₂₄ straight-chain alkyl, C ₁ -C ₂₄ branched-chain alkyl and -C ₆ -C ₂₄ aryl; R ₈ and R ₉ are respectively selected from C ₁ -C ₂₀ straight chain alkyl, C ₁ -C ₂₀ branched chain alkyl, C ₃ -C ₁₂ cycloalkyl, cycloalkylalkyl, cycloheteroalkylalkyl, One or more of C ₆ -C ₁₂ aryl groups and alkylaryl groups. 2. The oxime ester compound containing aryl sulfide furan or aryl sulfide thiophene according to claim 1, wherein the cycloalkyl alkyl group is selected from Among them, x=1-5, y=1-6; Preferably, the cycloheteroalkylalkyl is selected from Wherein, x=1-5, y=1-6, and z is selected from one or more of S, O, and N. 3. a preparation method of the oxime ester compound containing aryl sulfide furan or aryl sulfide thiophene according to claim 1, is characterized in that: it comprises the steps: (1), the aryl thiophenol substituted with R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , and brominated furanone or brominated thiophenone are reacted under alkaline conditions to obtain aryl sulfide substituted Furanone (Ia) or aryl sulfide substituted thiophenone (Ia): (2), the aryl sulfide substituted furanone (I-a) or the aryl sulfide substituted thiophenone (I-a) is reacted with hydroxylamine hydrochloride under basic conditions to obtain the oxime product (I-b): (3), the oxime product (I-b) is reacted with acid chloride or acid anhydride under alkaline action to obtain the oxime ester compound containing aryl sulfide furan or aryl sulfide thiophene: 4. preparation method according to claim 3 is characterized in that: R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ and R ₇ are respectively selected from hydrogen, halogen atom, R, OR, SR, more than one of SOR, SO ₂ R, NRR', CH ₂ OH, CH ₂ OR, CH ₂ OCOR, CH ₂ SR, CH ₂ SCOR and CH ₂ NRR'; Wherein, R and R' are respectively selected from one or more of C ₁ -C ₂₄ straight-chain alkyl, C ₁ -C ₂₄ branched-chain alkyl and -C ₆ -C ₂₄ aryl; R ₈ and R ₉ are respectively selected from C ₁ -C ₂₀ straight chain alkyl, C ₁ -C ₂₀ branched chain alkyl, C ₃ -C ₁₂ cycloalkyl, cycloalkylalkyl, cycloheteroalkylalkyl, One or more of C ₆ -C ₁₂ aryl groups and alkylaryl groups. 5. preparation method according to claim 4 is characterized in that: described cycloalkyl alkyl is selected from Among them, x=1-5, y=1-6; Preferably, the cycloheteroalkylalkyl is selected from Wherein, x=1-5, y=1-6, and z is selected from one or more of S, O, and N. 6. Use of the oxime ester compound containing aryl sulfide furan or aryl sulfide thiophene as claimed in claim 1 as a radiation curing photoinitiator. 7 . The use according to claim 6 , wherein the light source of the radiation-curing photoinitiator is selected from one or more of ultraviolet light and visible light. 8 . 8. The use according to claim 6, wherein the radiation curing photoinitiator comprises 0.01-30 parts by weight of an oxime ester compound containing aryl sulfide furan or aryl sulfide thiophene and 100 parts by weight of an oxime ester compound containing ethylenically unsaturated compounds; Preferably, the radiation curing photoinitiator comprises 0.5-10 parts by weight of an oxime ester compound containing aryl sulfide furan or aryl sulfide thiophene and 100 parts by weight of an ethylenically unsaturated compound. 9. The use according to claim 8, characterized in that: the ethylenically unsaturated compound is a compound or mixture whose ethylenic bond is cross-linked by radical polymerization; Preferably, the ethylenically unsaturated compound is selected from monomers, oligomers or prepolymers, or mixtures or copolymers of the three, or aqueous dispersions of the three.