Anthracene (ketone) oxime ester compound, product containing same and application of anthracene (ketone) oxime ester compound

Abstract

The invention belongs to the technical field of photocuring, and relates to an anthracene (ketone) oxime ester compound, a product containing the same and application of the anthracene (ketone) oxime ester compound. Specifically, the structure of the compound is shown as a formula (A), and the compound has a wide UV-Vis absorption spectrum at 350-460 nm, is excellent in photosensitive activity and can be matched with various visible light sources. Meanwhile, compared with an existing commercial photoinitiator, the compound disclosed by the invention has an anthracene rigid skeleton structure, vibration in molecules can be reduced, and energy transfer is fast, so that the initiation polymerization speed is accelerated. Moreover, the compound disclosed by the invention is simple in synthesis process, green, environment-friendly and suitable for industrial production. # imgabs0 #

Description

Technical Field

[0001] The present invention belongs to the technical field of photocuring, and relates to anthracene (ketone) oxime ester compounds, products containing the same, and their applications in the field of photocuring. Background Art

[0002] Photocuring technology refers to the process in which liquid oligomers form solid products through cross-linking polymerization under the action of light, and has the characteristics of "5E" (high efficiency, wide adaptability, economy, energy saving and environmental friendliness). Photoinitiators are a class of compounds that can absorb energy of a certain wavelength in the ultraviolet region (250 - 420 nm) or visible region (400 - 800 nm), generate active groups such as free radicals, cations, anions, etc., and thus initiate the polymerization and cross-linking curing of monomers. As an important part of the curing system, photoinitiators determine the speed of the photocuring reaction and affect the properties of photocuring materials. The absorption bands of traditional photoinitiators are generally in the ultraviolet region and are mainly used in ultraviolet curing systems, and the development of ultraviolet curing technology has been relatively mature. With the development of LED technology and the increasing demand for material materials by people, visible light photoinitiators have become a research hotspot. However, free radical type visible light photoinitiators are easily inhibited by oxygen during the initiation process, and the volume shrinkage after curing is relatively large; while the curing speed of cationic photoinitiators is slow, there are fewer available monomers and oligomers and they are more expensive, etc., which all limit the application scope of visible light curing technology. The currently reported photoinitiating systems usually involve introducing groups into ultraviolet photoinitiators to extend their absorption wavelengths to the visible region, with complex synthesis processes and low photoinitiating activities. In recent years, with the application and development of laser technology, a series of high-tech technologies such as laser holographic storage, three-dimensional modeling, laser plate-making, and laser printing have been developed. To meet this development need, the development of photoinitiators in the visible light and even near-infrared regions has received great attention. Therefore, the design and development of photoinitiators that match the emission wavelength of LEDs or are suitable for long wavelengths, have simple processes, and high initiating activities have gradually become a research hotspot. Summary of the Invention

[0003] Problems to be Solved by the Invention

[0004] In view of the above problems existing in the prior art, the present invention provides a series of anthracene (ketone) oxime ester compounds with novel structures, products containing the same, and their applications in the field of photocuring, in order to solve the above problems.

[0005] Solutions for Solving the Problems

[0006] In a first aspect, the present invention provides a compound of formula (A),

[0007]

[0008] Wherein,

[0009] A is absent or represents a carbonyl group;

[0010] R 1 is selected from C 1-20 alkyl, C 3-20 cycloalkyl and C 6-20 aryl, and the alkyl, cycloalkyl or aryl is unsubstituted or substituted by one or more R a groups;

[0011] R 2 is selected from C 1-20 alkyl and C 3-20 cycloalkyl, and the alkyl or cycloalkyl is unsubstituted or substituted by one or more R a groups;

[0012] R 3 and R 4 are each independently selected from C 1-20 alkyl, -(C=O)-C 1-20 alkyl, C 3-20 cycloalkyl, C 6-20 aryl, -(C=O)-C 6-20 aryl and a 4- to 20-membered heterocyclic group, and the alkyl, cycloalkyl, aryl or heterocyclic group is unsubstituted or substituted by one or more R b groups;

[0013] R 5 is selected from hydrogen, halogen, cyano, nitro, C 1-20 alkyl, -(C=O)-C 1-20 alkyl, C 3-20 cycloalkyl, C 6-20 aryl, -(C=O)-C 6-20 aryl and a 4- to 20-membered heterocyclic group, and the alkyl, cycloalkyl, aryl or heterocyclic group is unsubstituted or substituted by one or more R a groups;

[0014] Each R a is independently selected from C 1-20 alkyl, -O-C 1-20 alkyl, halo-C 1-20 alkyl, halogen and cyano;

[0015] Each R b is independently selected from halogen, nitro, cyano, C 1-20 alkyl, C 3-20 cycloalkyl, C 6-20 aryl, -O-C 1-20 alkyl and halo-C 1-20 alkyl.

[0016] Second aspect, the present invention provides a polymerizable composition comprising the compound in the first part.

[0017] Preferably, the polymerizable composition further comprises at least one of the following components:

[0018] a) Acrylic resin prepolymer;

[0019] b) Solvent.

[0020] More preferably, the polymerizable composition comprises the following components in parts by weight: 2 - 6 parts of the compound in the first part; 94 - 98 parts of acrylic resin prepolymer; and 100 parts of solvent.

[0021] Third aspect, the present invention provides a photosensitive composition comprising the compound in the first part.

[0022] Preferably, the photosensitive composition further comprises at least one of the following components:

[0023] a) Alkali-soluble resin;

[0024] b) Photopolymerizable compound;

[0025] c) Solvent.

[0026] More preferably, the photosensitive composition comprises the following components in parts by weight: 1 - 5 parts of the compound in the first part; 10 - 20 parts of alkali-soluble resin; 5 - 10 parts of photopolymerizable compound; and 80 - 100 parts of solvent.

[0027] Fourth aspect, the present invention provides a photoresist comprising the following components:

[0028] i) The compound in the first part;

[0029] ii) Alkali-soluble resin;

[0030] iii) Photopolymerizable compound;

[0031] iv) Auxiliary agent.

[0032] Preferably, the auxiliary agent is selected from solvents, colorants, fillers, dispersants, antioxidants, ultraviolet absorbers, curing accelerators, and thermal polymerization inhibitors.

[0033] Fifth aspect, the present invention provides the application of the compound in the first part, the polymerizable composition in the second part, the photosensitive composition in the third part, or the photoresist in the fourth part in the field of photocuring.

[0034] Effects of the Invention

[0035] 1. The anthracene (ketone) oxime ester compound of the present invention has a wide UV-Vis absorption spectrum in the range of 350 nm - 460 nm, excellent photosensitive activity, and can match a variety of visible light sources.

[0036] 2. Compared with the existing commercial photoinitiators, the compound of the present invention has an anthracene rigid skeleton structure, which can reduce the vibration inside the molecule, and the energy transfer is fast, thus accelerating the polymerization initiation rate.

[0037] 3. The compound of the present invention has strong modifiability, and the introduced alkyl chain further increases the solubility and improves the homogeneity of the photopolymerization system.

[0038] 4. The synthesis process of the compound of the present invention is simple, green and environmentally friendly, and is suitable for industrial production. BRIEF DESCRIPTION OF THE DRAWINGS

[0039] Figure 1 1H NMR spectrum of Compound 1 prepared in Example 1 1

[0040] Figure 2 Ultraviolet-visible absorption spectrum of Compound 1 prepared in Example 1 DETAILED DESCRIPTION OF THE INVENTION

[0041] The following will detail various exemplary embodiments, features and aspects of the present invention. The term "exemplary" used herein means "serving as an example, embodiment or illustration". Any embodiment described as "exemplary" herein need not be construed as superior or better than other embodiments.

[0042] In addition, in order to better illustrate the present invention, numerous specific details are given in the following detailed description. Those skilled in the art should understand that the present invention can be implemented without some specific details. In other instances, methods, means, equipment and steps well known to those skilled in the art are not described in detail so as to highlight the gist of the present invention.

[0043] Unless otherwise stated, the units used in this specification are all international standard units, and the numerical values and numerical ranges appearing in the present invention should be understood to include the systematic errors inevitable in industrial production.

[0044] In this specification, the meaning expressed by "can" includes both the meaning of performing a certain process and the meaning of not performing a certain process.

[0045] ​In this specification, the "some specific / preferred embodiments", "other specific / preferred embodiments", "embodiments", etc. mentioned refer to the specific elements (such as features, structures, properties, and / or characteristics) related to the embodiment, which are included in at least one of the embodiments described herein, and may or may not exist in other embodiments. Additionally, it should be understood that the elements can be combined in various embodiments in any suitable manner.

[0046] In this specification, the numerical range expressed as "numerical value A to numerical value B" refers to the range including the endpoint numerical values A and B.

[0047] The abbreviations used herein have the following meanings:

[0048] Abbreviation Meaning Abbreviation Meaning TLC Thin Layer Chromatography NMR Nuclear Magnetic Resonance <![CDATA[AlCl 3 > Aluminum Trichloride TBAB Tetrabutylammonium Bromide DBA 9,10-Dibutoxyanthracene NaOH Sodium Hydroxide PGMEA Propylene Glycol Methyl Ether Acetate

[0049] Term Definition

[0050] The term "substituted" and its other variant forms herein refer to one or more (such as 1, 2, 3, or 4) atoms or atomic groups (such as hydrogen atoms) on the specified atom being replaced by other equivalents, provided that the normal valence of the specified atom or atomic group in the current situation is not exceeded and a stable compound can be formed. If an atom or atomic group is described as "optionally substituted by...", it can either be substituted or unsubstituted. Unless otherwise specified, the attachment site of the substituent can be from any suitable position of the substituent. When the connecting bond in the substituent is shown as a chemical bond passing between two interconnected atoms in a ring system, it means that the substituent can be attached to any ring-forming atom in the ring system.

[0051] The term "independently" means that at least two groups (or ring systems) with the same or similar value ranges existing in a structure can have the same or different meanings in a specific situation. For example, if the substituents X and Y are independently hydrogen, halogen, hydroxyl, cyano, alkyl, or aryl, then when the substituent X is hydrogen, the substituent Y can be either hydrogen or halogen, hydroxyl, cyano, alkyl, or aryl; similarly, when the substituent Y is hydrogen, the substituent X can be either hydrogen or halogen, hydroxyl, cyano, alkyl, or aryl.

[0052] The term "halogen" refers to fluorine (F), chlorine (Cl), bromine (Br), and iodine (I).

[0053] The term "alkyl" refers to a saturated aliphatic hydrocarbon group, including straight-chain or branched-chain saturated hydrocarbon groups having the indicated number of carbon atoms. Such as the term "C" 1-6"Alkyl" refers to a straight-chain or branched-chain saturated hydrocarbon group containing 1 to 6 carbon atoms, either alone or in combination, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, 2-pentyl, 3-pentyl, n-hexyl, 2-hexyl, 3-hexyl, etc. The alkyl group can be optionally substituted or unsubstituted.

[0054] The term "cycloalkyl" refers to a saturated or partially saturated, monocyclic or polycyclic (such as bicyclic, e.g., fused, bridged or spirocyclic) non-aromatic hydrocarbon group. For example, the term "C 3-8 cycloalkyl" refers to a cycloalkyl group having 3 to 8 carbon atoms. Examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. The cycloalkyl group can be optionally substituted or unsubstituted.

[0055] The term "heterocyclic group" refers to a saturated or partially saturated, monocyclic or polycyclic (such as bicyclic, e.g., fused, bridged or spirocyclic) non-aromatic group, the ring atoms of which consist of carbon atoms and at least one heteroatom selected from N, O, and S. If the valence bond requirements are met, the heterocyclic group can be linked to the rest of the molecule through any one of the ring atoms.

[0056] The term "aryl" refers to a monocyclic or fused polycyclic aromatic hydrocarbon group having a conjugated π-electron system. For example, the term "C 6-10 aryl" refers to an aryl group having 6 to 10 carbon atoms. Common aryl groups include (but are not limited to) phenyl, naphthyl, anthryl, phenanthryl, acenaphthylenyl, azulenyl, fluorenyl, indenyl, pyrenyl, etc. The aryl group can be optionally substituted or unsubstituted.

[0057] Anthracene (Ketone) Oxime Ester Compound

[0058] The present invention provides an anthracene (ketone) oxime ester compound, the structure of which can be shown as formula (A):

[0059]

[0060] Wherein,

[0061] A is absent or represents a carbonyl group;

[0062] R 1 is selected from C 1-20 alkyl, C 3-20 cycloalkyl and C 6-20 aryl, and the alkyl, cycloalkyl or aryl is unsubstituted or substituted by one or more R a substituents;

[0063] R 2 is selected from C 1-20 alkyl and C 3-20 cycloalkyl, and the alkyl or cycloalkyl is unsubstituted or substituted by one or more Ra Substitute;

[0064] R 3 and R 4 are each independently selected from C 1-20 alkyl, -(C=O)-C 1-20 alkyl, C 3-20 cycloalkyl, C 6-20 aryl, -(C=O)-C 6-20 aryl and a 4-20 membered heterocyclic group, and the alkyl, cycloalkyl, aryl or heterocyclic group is unsubstituted or substituted by one or more R b Substitute;

[0065] R 5 is selected from hydrogen, halogen, cyano, nitro, C 1-20 alkyl, -(C=O)-C 1-20 alkyl, C 3-20 cycloalkyl, C 6-20 aryl, -(C=O)-C 6-20 aryl and a 4-20 membered heterocyclic group, and the alkyl, cycloalkyl, aryl or heterocyclic group is unsubstituted or substituted by one or more R a Substitute;

[0066] Each R a is each independently selected from C 1-20 alkyl, -O-C 1-20 alkyl, halo C 1-20 alkyl, halogen and cyano;

[0067] Each R b is each independently selected from halogen, nitro, cyano, C 1-20 alkyl, C 3-20 cycloalkyl, C 6-20 aryl, -O-C 1-20 alkyl and halo C 1-20 alkyl.

[0068] In one embodiment of the present invention, the structure of the anthracene (ketone) oxime ester compound can be as shown in formula (I) or formula (II):

[0069]

[0070] wherein, R 1 , R 2 , R 3 , R 4 and R 5 are as defined in formula (A).

[0071] In one embodiment of the present invention, in formula (A), formula (I) and formula (II), R 1 is selected from C1-10 alkyl, C 3-10 cycloalkyl and C 6-10 aryl, wherein the alkyl, cycloalkyl or aryl is unsubstituted or substituted by one or more R a substituents; each R a is independently selected from C 1-10 alkyl, -O-C 1-10 alkyl, halo-C 1-10 alkyl, halogen and cyano.

[0072] In one embodiment of the present invention, in formula (A), formula (I) and formula (II), R 1 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, n-octyl, isononyl, phenyl, ethylphenyl, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

[0073] In one embodiment of the present invention, in formula (A), formula (I) and formula (II), R 1 is selected from methyl and phenyl.

[0074] In one embodiment of the present invention, in formula (A), formula (I) and formula (II), R 2 is selected from C 1-10 alkyl and C 3-10 cycloalkyl, wherein the alkyl or cycloalkyl is unsubstituted or substituted by one or more R a substituents; each R a is independently selected from C 1-10 alkyl, -O-C 1-10 alkyl, halo-C 1-10 alkyl, halogen and cyano.

[0075] In one embodiment of the present invention, in formula (A), formula (I) and formula (II), R 2 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, n-octyl, isononyl, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

[0076] In one embodiment of the present invention, in formula (A), formula (I) and formula (II), R 2 is selected from methyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, cyclopentyl and cyclohexyl.

[0077] In one embodiment of the present invention, in formula (A), formula (I) and formula (II), R 3 and R 4 are independently selected from C 1-10alkyl, -(C=O)-C 1-10 alkyl, C 3-10 cycloalkyl, C 6-10 aryl, -(C=O)-C 6-10 aryl and 4- to 10-membered heterocyclic group, wherein the alkyl, cycloalkyl, aryl or heterocyclic group is unsubstituted or substituted by one or more R b each R b is independently selected from halogen, nitro, cyano, C 1-10 alkyl, C 3-10 cycloalkyl, C 6-10 aryl, -O-C 1-10 alkyl and halo C 1-10 alkyl.

[0078] In one embodiment of the present invention, in formula (A), formula (I) and formula (II), R 3 and R 4 are each independently selected from C 1-10 alkyl, -(C=O)-C 1-10 alkyl, C 3-10 cycloalkyl, C 6-10 aryl and -(C=O)-C 6-10 aryl, wherein the alkyl, cycloalkyl or aryl is unsubstituted or substituted by one or more R b each R b is independently selected from halogen, nitro, cyano, C 1-10 alkyl, C 3-10 cycloalkyl, C 6-10 aryl, -O-C 1-10 alkyl and halo C 1-10 alkyl.

[0079] In one embodiment of the present invention, in formula (A), formula (I) and formula (II), R 3 and R 4 are each independently selected from C 1-8 alkyl, -(C=O)-C 1-8 alkyl, C 3-8 cycloalkyl, phenyl and -(C=O)-phenyl, wherein the alkyl, cycloalkyl and phenyl are unsubstituted or substituted by one or more R b each R b is independently selected from halogen, nitro, cyano, C 1-8 alkyl, C 3-8 cycloalkyl, C 6-8 aryl, -O-C 1-8 alkyl and halo C 1-8 alkyl.

[0080] In one embodiment of the present invention, in formula (A), formula (I) and formula (II), R 3 and R 4 are each independently selected from methyl, ethyl, n-propyl, n-butyl, n-pentyl, 4-methylpentyl, 5-methylhexyl, n-heptyl, phenyl, benzyl, benzoyl, cyclopentyl, cyclopentylmethyl and 1-butyryl.

[0081] In one embodiment of the present invention, in formula (A), formula (I) and formula (II), R 5 is selected from hydrogen, halogen, cyano, nitro, C 1-20 alkyl, -(C=O)-C 1-20 alkyl, C 3-20 cycloalkyl, C 6-20 aryl, -(C=O)-C 6-20 aryl and 4- to 20-membered heterocyclic group.

[0082] In one embodiment of the present invention, in formula (A), formula (I) and formula (II), R 5 is selected from hydrogen, halogen, cyano, nitro, C 1-10 alkyl, C 3-10 cycloalkyl, C 6-10 aryl and 4- to 10-membered heterocyclic group.

[0083] In one embodiment of the present invention, in formula (A), formula (I) and formula (II), R 5 is selected from hydrogen, nitro and C 1-10 alkyl.

[0084] In one embodiment of the present invention, in formula (A), formula (I) and formula (II), R 5 is selected from hydrogen, nitro and methyl.

[0085] In one embodiment of the present invention, the anthracene (ketone) oxime ester compound may be selected from the following compounds:

[0086]

[0087]

[0088]

[0089]

[0090]

[0091] Product Containing Anthracene (Ketone) Oxime Ester Compound Photoinitiator

[0092] The above-mentioned anthracene (ketone) oxime ester compound of the present invention can be used as a photoinitiator (or photoinitiator) in the field of photocuring, for example, as a photoinitiator component in a photosensitive composition or a photoresist.

[0093] For this reason, the present invention provides a photosensitive composition, which may contain the above-mentioned anthracene (ketone) oxime ester compound of the present invention as a photoinitiator.

[0094] In an embodiment of the present invention, the photosensitive composition may further contain at least one of the following components:

[0095] a) An alkali-soluble resin;

[0096] b) A photopolymerizable compound;

[0097] c) A solvent.

[0098] In an embodiment of the present invention, the alkali-soluble resin may be an acrylic copolymer, for example, a copolymer of (meth)acrylic acid and one or more of its esters, and may also be a copolymer of two or more (meth)acrylate esters.

[0099] In an embodiment of the present invention, the alkali-soluble resin may be a copolymer of methacrylic acid, alkyl methacrylate, and hydroxyalkyl methacrylate, for example, a copolymer of methacrylic acid, methyl methacrylate, n-butyl methacrylate, and 2-hydroxyethyl methacrylate, especially a copolymer with a weight ratio of 4:2:11:3 in sequence.

[0100] In an embodiment of the present invention, the photopolymerizable compound may be a photopolymerizable compound having an ethylenically unsaturated structure, for example, a (meth)acrylic acid polyol ester.

[0101] In an embodiment of the present invention, the photopolymerizable compound may be trimethylolpropane triacrylate.

[0102] In an embodiment of the present invention, the solvent may be a diol monoether, for example, a diol monoalkyl ether.

[0103] In an embodiment of the present invention, the solvent may be ethyl cellosolve (i.e., ethylene glycol monoethyl ether).

[0104] In an embodiment of the present invention, the photosensitive composition may contain the following components by weight:

[0105] 1-5 parts of the above-mentioned anthracene (ketone) oxime ester compound of the present invention as a photoinitiator;

[0106] 10-20 parts of an alkali-soluble resin;

[0107] 5 - 10 parts of a photopolymerizable compound;

[0108] 80 - 100 parts of a solvent.

[0109] In one embodiment of the present invention, the photosensitive composition may comprise the following components in parts by weight:

[0110] 2 - 4 parts of the above - mentioned anthracene (ketone) oxime ester compound of the present invention as a photoinitiator;

[0111] 12 - 18 parts of an alkali - soluble resin;

[0112] 6 - 8 parts of a photopolymerizable compound;

[0113] 80 - 90 parts of a solvent.

[0114] In one embodiment of the present invention, the photosensitive composition may comprise the following components in parts by weight:

[0115] 3.0 parts of the above - mentioned anthracene (ketone) oxime ester compound of the present invention as a photoinitiator;

[0116] 15.5 parts of an alkali - soluble resin;

[0117] 6.4 parts of a photopolymerizable compound;

[0118] 87.7 parts of a solvent.

[0119] In one embodiment of the present invention, the photosensitive composition may be composed of the above - mentioned anthracene (ketone) oxime ester compound of the present invention as a photoinitiator, an alkali - soluble resin, a photopolymerizable compound, and a solvent.

[0120] The present invention also provides a photoresist, which may comprise the following components:

[0121] i) The above - mentioned anthracene (ketone) oxime ester compound of the present invention as a photoinitiator;

[0122] ii) An alkali - soluble resin;

[0123] iii) A photopolymerizable compound;

[0124] iv) An auxiliary agent.

[0125] In one embodiment of the present invention, the auxiliary agent in the photoresist may be selected from solvents, colorants, fillers, dispersants, antioxidants, ultraviolet absorbers, curing accelerators, and thermal polymerization inhibitors.

[0126] In one embodiment of the present invention, the photoresist may comprise the following components:

[0127] i-1) The above-mentioned anthracene (ketone) oxime ester compound of the present invention as a photoinitiator;

[0128] ii-1) An alkali-soluble resin;

[0129] iii-1) A photopolymerizable compound;

[0130] iv-1) A solvent and an optional colorant.

[0131] Application of the Product in the Field of Photocuring

[0132] The present invention provides the application of the above-mentioned anthracene (ketone) oxime ester compound, photosensitive composition or photoresist in the field of photocuring.

[0133] Examples

[0134] The embodiments of the present invention will be described in detail below in conjunction with examples. However, those skilled in the art will understand that the following examples are only used to illustrate the present invention and should not be regarded as limiting the scope of the present invention. For those not specified in the examples, they are carried out under conventional conditions or conditions recommended by the manufacturer. For reagents or instruments not specified for the manufacturer, they are all conventional products that can be obtained through commercial purchase.

[0135] Synthesis of Compound of Formula (I):

[0136]

[0137] Note: When R 3 is the same as R 4 , compound C (i.e., R 3 -X 1 or R 4 -X 2 , where X 1 =X 2 ) is used in S3; when R 3 is different from R 4 , compound C1 (R 4 -X 2 ) is first used in S3, and then compound C2 (R 3 -X 1 ) is used.

[0138] Example 1: Synthesis of Compound 1

[0139]

[0140] S1: Add phthalic anhydride (16.5 g, 111.40 mmol, 1 eq) and ethylbenzene (12.06 g, 113.53 mmol, 1.02 eq) into a 250 mL round-bottom flask, add 200 mL of carbon tetrachloride, dissolve in an oil bath at 50 °C, and then add anhydrous AlCl 3 (37.13 g, 278.50 mmol, 2.5 eq) in batches, and react for 4 - 5 h. After the reaction is completed, rotary evaporate the carbon tetrachloride, slowly add 10% dilute sulfuric acid solution dropwise to the reaction flask under the condition of a cold well, cool, filter by suction and wash with a large amount of water to obtain the filter cake, and dry it. Prepare an aqueous NaOH solution, dissolve the obtained dry solid, filter by suction to remove the insoluble substances, extract the filtrate three times with ethyl acetate, and discard the ethyl acetate layer. Slowly add 10% dilute sulfuric acid solution dropwise to the aqueous NaOH layer, precipitate a white solid, filter by suction and dry it, then add it to a 250 mL round-bottom flask, use concentrated sulfuric acid as the solvent, and react in an oil bath at 100 °C for 2 - 3 h. After the reaction is completed, slowly add the reaction solution dropwise to cold water, a large amount of pale yellow solid precipitates, cool and filter by suction, and perform solid silica gel column chromatography (eluent: EA:PE = 1:5) to obtain compound 1-1 (20 g), yield: 75.99%, EI-MS: m / z 236.27 [M+H] + .

[0141] S2: Add compound 1-1 (20.0 g, 84.65 mmol, 1 eq) into a three-necked flask, dissolve it after adding 2-methyltetrahydrofuran (150 mL), dissolve iodine (2.15 g, 8.46 mmol, 0.1 eq) after adding, heat up to reflux, slowly dropwise add tert-butyl hydroperoxide (9.92 g, 111.04 mmol, 1.3 eq), continue reflux reaction after dropping, monitor the reaction to be complete by TLC plate spotting, add an aqueous solution of sodium bisulfite for washing with water, extract three times with ethyl acetate, combine the organic phases, concentrate to dryness and recrystallize with ethanol to obtain a yellow-green solid compound 1-2 (16 g), yield 75.53%, EI-MS: m / z 250.25 [M+H] + .

[0142] S3: Add compound 1-2 (15.0 g, 59.94 mmol, 1 eq) into a three-necked flask. After dissolving it in 100 mL of chlorobenzene, add TBAB (0.15 g), and slowly add sodium dithionite (31.31 g, 179.82 mmol, 3 eq). After addition and stabilization, displace the air with nitrogen three times, then heat up to 100 °C. After stabilization, dropwise add n-butyl bromide (24.64 g, 179.82 mmol, 3 eq). After the addition is complete, heat up to reflux for reaction. After monitoring the reaction to completion by TLC plate spotting, add 200 mL of water to quench the reaction. Separate the layers, extract the aqueous phase with ethyl acetate, combine the organic phases, concentrate to dryness, and purify by solid silica gel column chromatography (eluent: EA:PE = 1:15) to obtain the brownish liquid compound 1-3 (18 g), with a yield of 82.39%, EI-MS: m / z 364.49 [M+H] + 。

[0143] S4: Add compound 1-3 (18.0 g, 49.38 mmol, 1 eq) into a three-necked flask. After stirring and dissolving it in 100 mL of dichloroethane, successively add sodium acetate (12.15 g, 148.15 mmol, 3 eq) and hydroxylamine hydrochloride (6.86 g, 98.77 mmol, 2 eq). After displacing the air with nitrogen, heat up to reflux. After monitoring the reaction to completion by TLC plate spotting, add 200 mL of water to quench the reaction. Separate the layers, extract the aqueous phase with ethyl acetate, combine the organic phases, concentrate to dryness, and purify by solid silica gel column chromatography (eluent: EA:PE = 1:5) to obtain the brownish liquid compound 1-4 (16 g), with a yield of 85.37%, EI-MS: m / z 379.50 [M+H] + 。

[0144] S5: Add compound 1-4 (16.0 g, 42.16 mmol, 1 eq) into a three-necked flask. After stirring and dissolving it in 100 mL of dichloroethane, add triethylamine (6.4 g, 63.24 mmol, 1.5 eq). Under an ice-water bath, dropwise add acetyl chloride (3.97 g, 50.59 mmol, 1.2 eq). After the addition is complete, restore to room temperature for reaction. After monitoring the reaction to completion by TLC plate spotting, add 200 mL of water to quench the reaction. Separate the layers, extract the aqueous phase with ethyl acetate, combine the organic phases, concentrate to dryness, and purify by solid silica gel column chromatography (eluent: EA:PE = 1:5) to obtain the light yellow solid compound 1 (15 g), with a yield of 84.40%, EI-MS: m / z 421.54 [M+H] + 。

[0145] The NMR spectrum of compound 1 is as Figure 1 shown.

[0146] Example 2-4

[0147] Refer to the synthetic route in Reference Example 1, and select the corresponding Compound A, Compound B, Compound C, and Compound D to prepare a series of specific compounds of the present invention (see Table 1).

[0148] Table 1

[0149]

[0150] Synthesis of Compound of Formula (II):

[0151]

[0152] Note: When R 3 is the same as R 4 , Compound C is used in S3 (i.e., R 3 -X 1 or R 4 -X 2 , where X 1 =X 2 ); when R 3 is different from R 4 , Compound C1 (R 4 -X 2 ) is used first in S3, and then Compound C2 (R 3 -X 1 ) is used.

[0153] Example 5: Synthesis of Compound 112

[0154]

[0155] S1: Add phthalic anhydride (15.2 g, 102.62 mmol, 1 eq) and pentylbenzene (15.97 g, 107.75 mmol, 1.05 eq) to a 250 mL round-bottom flask, add 200 mL of carbon tetrachloride as the solvent, dissolve in an oil bath at 50 °C, and then add anhydrous AlCl 3(34.21 g, 256.55 mmol, 2.5 eq), react for 4 - 5 h. After the reaction is completed, rotary evaporate the carbon tetrachloride. Slowly add 10% dilute sulfuric acid solution dropwise to the reaction flask under cold well conditions. Let it cool, filter by suction and wash with a large amount of water to obtain the filter cake, and then dry it. Prepare an aqueous NaOH solution, dissolve the obtained dried solid, filter by suction to remove the insoluble matter, and extract the filtrate with ethyl acetate three times, discarding the ethyl acetate layer. Slowly add 10% dilute sulfuric acid solution dropwise to the aqueous NaOH layer to precipitate a white solid. After filtering by suction and drying, add it to a 250 mL round-bottom flask, use concentrated sulfuric acid as the solvent, and react in an oil bath at 100 °C for 2 - 3 h. After the reaction is completed, slowly add the reaction solution dropwise to cold water, and a large amount of pale yellow solid will precipitate. Let it cool and filter by suction. The solid is purified by column chromatography to obtain compound 112-1 (20 g), yield: 70.02%, EI-MS: m / z 278.35 [M+H] + 。

[0156] S2: Add compound 112-1 (20.0 g, 71.85 mmol, 1 eq) to a three-necked flask. After dissolving it with 2-methyltetrahydrofuran (100 mL), add iodine (1.82 g, 7.19 mmol, 0.1 eq) and dissolve it. Then heat up to reflux, and slowly dropwise add tert-butyl hydroperoxide (8.42 g, 93.41 mmol, 1.3 eq). After the addition is completed, continue the reflux reaction. After monitoring the reaction to be complete by TLC spotting, add an aqueous sodium bisulfite solution for washing with water, extract with ethyl acetate three times, and then combine the organic phases. After concentrating to dryness, recrystallize with ethanol to obtain a yellow-green solid compound 112-2 (15 g), yield 71.41%, EI-MS: m / z 292.33 [M+H] + 。

[0157] S3: Add compound 112-2 (15.0 g, 51.31 mmol, 1 eq) to a three-necked flask. After dissolving it with 100 mL of chlorobenzene, add TBAB (0.15 g), and slowly add sodium dithionite (26.80 g, 153.93 mmol, 3 eq). After adding and stabilizing, displace with nitrogen three times, then heat up to 100 °C. After stabilizing, dropwise add n-butyl bromide (21.09 g, 153.93 mmol, 3 eq). After the addition is completed, heat up to reflux for reaction. After monitoring the reaction to be complete by TLC spotting, add 200 mL of water to quench the reaction, separate the layers, extract the aqueous phase with ethyl acetate, combine the organic phases, and after concentrating to dryness, purify by column chromatography with solid silica gel (eluent: EA:PE = 1:10) to obtain a brownish liquid compound 112-3 (17 g), yield 81.49%, EI-MS: m / z 406.57 [M+H] + 。

[0158] S4: Add compound 112-3 (17.0 g, 41.81 mmol, 1 eq) into a three-necked flask. After adding 100 mL of tetrahydrofuran and stirring until dissolved, cool the solution to -5 - 0 °C. Then, add concentrated hydrochloric acid (1.72 g, 47.25 mmol, 1.13 eq) and isoamyl nitrite (5.39 g, 45.99 mmol, 1.1 eq) successively. After the addition, keep the reaction at a constant temperature. Monitor the reaction by TLC plate until it is complete. Then, add 200 mL of water to quench the reaction. Separate the layers. Extract the aqueous phase with ethyl acetate. Combine the organic phases, concentrate to dryness, and perform column chromatography on silica gel (eluent: EA:PE = 1:3) to obtain a brownish liquid compound 112-4 (15 g) with a yield of 82.36%. EI-MS: m / z 435.56 [M+H] + 。

[0159] S5: Add compound 112-4 (16.0 g, 34.44 mmol, 1 eq) into a three-necked flask. After adding 100 mL of dichloroethane and stirring until dissolved, add triethylamine (5.23 g, 51.66 mmol, 1.5 eq). Dropwise add acetyl chloride (3.24 g, 41.33 mmol, 1.2 eq) under an ice-water bath. After the addition, restore the temperature to room temperature and continue the reaction. Monitor the reaction by TLC plate until it is complete. Then, add 200 mL of water to quench the reaction. Separate the layers. Extract the aqueous phase with ethyl acetate. Combine the organic phases, concentrate to dryness, and perform column chromatography on silica gel (eluent: EA:PE = 1:5) to obtain a light yellow solid compound 112 (15 g) with a yield of 91.20%. EI-MS: m / z 477.60 [M+H] + 。

[0160] Examples 6 - 8

[0161] Refer to the synthetic route in Reference Example 5, and select the corresponding Compound A, Compound B, Compound C, and Compound D to prepare a series of specific compounds of the present invention (see Table 2).

[0162] Table 2

[0163]

[0164] Example 9: Synthesis of Compound 156

[0165]

[0166] S1 and S2 are the same as S1 and S2 in the preparation method of Compound 1, and will not be elaborated here.

[0167] S3: Add compound 156-2 (15.0 g, 59.94 mmol, 1 eq) into a three-necked flask. After dissolving it in 100 mL of chlorobenzene, add TBAB (0.15 g), and slowly add sodium dithionite (31.31 g, 179.82 mmol, 3 eq). After addition and stabilization, displace the air with nitrogen three times, then heat up to 100 °C. After stabilization, add n-butyl bromide (12.32 g, 59.94 mmol, 1 eq) dropwise. After the addition is complete, heat up to reflux and react for 1 h, then cool down to 100 °C. After stabilization, add bromobenzene (18.8 g, 119.98 mmol, 2 eq) dropwise. After the addition is complete, heat up to reflux and react. After monitoring the reaction to completion by TLC plate spotting, add 200 mL of water to quench the reaction, separate the layers, extract the aqueous phase with ethyl acetate, combine the organic phases, concentrate to dryness, and purify by column chromatography on silica gel (eluent: EA:PE = 1:15) to obtain a brownish liquid compound 156-3 (12.9 g), with a yield of 42%, EI-MS: m / z 385.17 [M+H] + 。

[0168] S4: Add compound 156-3 (12.9 g, 33.58 mmol, 1 eq) into a three-necked flask. After stirring and dissolving it in 100 mL of dichloroethane, add sodium acetate (8.26 g, 100.74 mmol, 3 eq) and hydroxylamine hydrochloride (4.67 g, 67.16 mmol, 2 eq) in sequence. After displacing the air with nitrogen, heat up to reflux. After monitoring the reaction to completion by TLC plate spotting, add 200 mL of water to quench the reaction, separate the layers, extract the aqueous phase with ethyl acetate, combine the organic phases, concentrate to dryness, and purify by column chromatography on silica gel (eluent: EA:PE = 1:5) to obtain a brownish liquid compound 156-4 (11.01 g), with a yield of 82.17%, EI-MS: m / z 400.19 [M+H] + 。

[0169] S5: Add compound 156-4 (11.01 g, 27.59 mmol, 1 eq) into a three-necked flask. After stirring and dissolving it in 100 mL of dichloroethane, add triethylamine (4.19 g, 41.38 mmol, 1.5 eq), and add acetyl chloride (2.60 g, 33.11 mmol, 1.2 eq) dropwise under an ice-water bath. After the addition is complete, restore to room temperature and react. After monitoring the reaction to completion by TLC plate spotting, add 200 mL of water to quench the reaction, separate the layers, extract the aqueous phase with ethyl acetate, combine the organic phases, concentrate to dryness, and purify by column chromatography on silica gel (eluent: EA:PE = 1:5) to obtain a light yellow solid compound 156 (9.62 g), with a yield of 79%, EI-MS: m / z 442.54 [M+H] + 。

[0170] Example 10: Preparation of photosensitive composition 1

[0171] In an acrylic copolymer (15.5 g), trimethylolpropane triacrylate (6.4 g), Compound 1 (3 g), and ethyl cellosolve (87.7 g) were added, and the mixture was stirred well to obtain Photosensitive Composition 1.

[0172] The above acrylic copolymer was obtained by the following method: 20 parts by mass of methacrylic acid, 15 parts by mass of 2-hydroxyethyl methacrylate, 10 parts by mass of methyl methacrylate, and 55 parts by mass of butyl methacrylate were dissolved in 300 parts by mass of ethyl cellosolve. After adding 0.75 part by mass of azobisisobutyronitrile under a nitrogen atmosphere, the reaction was carried out at 70 °C for 5 h to obtain the acrylic copolymer.

[0173] Examples 11 - 18: Preparation of Photosensitive Compositions 2 - 9

[0174] Except for replacing Compound 1 with each of the compounds in Table 3, referring to the method in Example 10, the photosensitive compositions in Examples 11 - 18 and Comparative Examples 1 - 3 were obtained.

[0175] Table 3

[0176]

[0177] Among them, as control compounds, the structures of the compounds used as photoinitiators in Comparative Examples 1 - 3 are shown below.

[0178]

[0179] <Hardness Test>

[0180] Using a #3 bar coater, the photosensitive compositions in Examples 10 - 18 and Comparative Examples 1 - 3 were coated on a polyethylene terephthalate film with a thickness of 50 μm. Using a light irradiation device with a belt conveyor, a 405 nm LED light source and a 455 nm LED light source with a line power of 80 W / cm 2 were irradiated. The distance from the lamp to the belt conveyor was set to 10 cm, and the linear speed of the belt conveyor was set to 8 cm / min. After curing, it was left at room temperature for 24 h, and then using a pencil hardness tester, the pencil hardness at a load of 1 kg was measured. The test results are shown in Table 4.

[0181] Table 4

[0182]

[0183] As can be seen from Table 4, under the irradiation of 405 nm and 455 nm LED light sources, the curing hardness of the photosensitive compositions based on the compounds of the present invention in Examples 10-18 is significantly higher than that of the photosensitive compositions based on OXE02, DBA, and OXE01 in Comparative Examples 1-3, indicating that the compounds of the present invention are suitable for application in the field of photocuring.

[0184] Example 19: Preparation of Polymerizable Composition (Photosensitive Resin) 1

[0185] Add the acrylic resin prepolymer (96 g), Compound 1 (4 g), and tetrahydrofuran (100 g) to a reaction vessel at 35 °C, react for 6 h, and stir evenly to obtain Polymerizable Composition 1.

[0186] The above acrylic resin prepolymer is prepared by the following method: Dissolve 10 parts by mass of methacrylic acid, 10 parts by mass of methyl methacrylate, and 10 parts by mass of isobornyl methacrylate in 50 parts by mass of propylene glycol monomethyl ether acetate. Under the catalysis of 0.5 part by mass of azobisisobutyronitrile (AIBN), the reaction system is kept at 70-80 °C for 2 h to obtain the acrylic resin prepolymer.

[0187] Examples 20-27: Preparation of Polymerizable Compositions 2-9

[0188] Except for replacing Compound 1 with the respective compounds in Table 5, refer to the method in Example 19 to obtain the polymerizable compositions in Examples 20-27 and Comparative Examples 4-6.

[0189] Table 5

[0190] Examples Acrylic Resin Prepolymer Photoinitiator Compound Tetrahydrofuran Example 19 96g 1(4g) 100g Example 20 96g 8(4g) 100g Example 21 96g 83(4g) 100g Example 22 96g 23(4g) 100g Example 23 96g 112(4g) 100g Example 24 96g 113(4g) 100g Example 25 96g 147(4g) 100g Example 26 96g 148(4g) 100g Example 27 96g 156(4g) 100g Comparative Example 4 96g OXE02 (4g) 100g Comparative Example 5 96g DBA (4g) 100g Comparative Example 6 96g OXE01 (4g) 100g

[0191] According to the following method, evaluate the photosensitive activity of the polymerizable compositions in Examples 19-27 and Comparative Examples 4-6 above.

[0192] <Evaluation of Photosensitive Activity under 405 nm LED Light Source and 455 nm LED Irradiation>

[0193] Using a spin coater, coat the polymerizable compositions of Examples 19-27 and Comparative Examples 4-6 on a glass substrate. Using a spin coater, heat to 100 °C and hold for 2 min at a rotation speed of 1500 rpm, and then cool to room temperature to form a coating film on the surface of the glass substrate. Then, under the irradiation of a 405 nm LED light source and a 455 nm LED light source respectively, cure the polymerizable compositions of Examples 19-27 and Comparative Examples 4-6. Table 6 shows the exposure amount required for complete curing. The smaller this value, the better the photosensitive activity.

[0194] Table 6

[0195]

[0196] As can be seen from Table 6, under the irradiation of a 405 nm LED light source, the energy required for curing the polymerizable composition added with the compound of the present invention is significantly less than that required for curing the polymerizable composition added with control compounds (OXE02, DBA, and OXE01). Under the irradiation of a 455 nm LED light source, the energy required for curing the polymerizable composition added with the compound of the present invention is significantly less than that required for curing the polymerizable composition added with control compounds (DBA and OXE01), while the polymerizable composition in Comparative Example 4 cannot be cured. Compared with the compounds (OXE02, DBA, and OXE01) used in Comparative Examples 4 - 6, the compound of the present invention can well match the 405 nm and 455 nm LED light sources, has more excellent photosensitive activity, and is useful as a photoinitiator for optical applications.

[0197] <Solubility test>

[0198] Weigh 100 g of PGMEA, add 100 g of Compound 1 under the condition of 25 °C, stir and dissolve for 2 h, then perform suction filtration. The filter cake is rinsed with n - hexane and weighed after vacuum drying. The solubility in 100 g of PGMEA is obtained by subtracting the mass of the filter cake from 100 g; according to the same method, the solubility of other photoinitiator compounds in PGMEA is measured, and the results are listed in Table 7.

[0199] Table 7

[0200] Examples Photoinitiator Compound Solubility (g) / 100g PGMEA @ 25°C Example 28 Compound 1 >100 Example 29 Compound 8 96 Example 30 Compound 83 >100 Example 31 Compound 23 >100 Example 32 Compound 112 >100 Example 33 Compound 113 85 Example 34 Compound 147 >100 Example 35 Compound 148 92 Example 36 Compound 156 81 Comparative Example 7 OXE02 9 Comparative Example 8 DBA >100 Comparative Example 9 OXE01 90

[0201] Note: The result of >100 g indicates that after adding 100 g of the compound in this method, the solution is clear and no precipitation occurs.

[0202] As can be seen from Table 7, the solubility of the photoinitiator compounds of the present invention in Examples 28 - 36 is excellent, which can ensure the uniformity of the formulation.

[0203] <UV - Vis absorption experiment>

[0204] UV - Vis spectral experiments were carried out in acetonitrile solutions with the concentrations of Compound 1 being 1×10 -3 g / ml, 1×10 -4 g / ml, and 1×10 -5 g / ml respectively, and the UV - Vis absorption spectra of the compound at these three concentrations were obtained. As can be seen from Figure 2 it, the compound of the present invention has a relatively wide UV - Vis absorption spectrum in the range of 350 nm - 460 nm, and can match the existing long - wavelength light sources.

[0205] The specific operation steps are as follows: Prepare acetonitrile solutions of Compound 1 at different concentrations, which are 1×10 -3 g / ml, 1×10 -4 g / ml, and 1×10 -5 g / ml respectively. Analyze them by ultraviolet-visible spectrophotometry, perform wavelength scanning in the range of 190 - 700 nm, and obtain their absorption spectra and maximum absorption wavelengths.

[0206] In summary, the anthracene (ketone) oxime ester compounds designed by the present invention exhibit good solubility, excellent application performance, wide adaptability to UV-LED light sources, greatly improve the performance of photocurable products, and play a very good role in promoting the popularization and application of UV-LED light sources in the field of photocuring.

[0207] It should be noted that although the technical solutions of the present invention are introduced with specific examples, those skilled in the art can understand that the present invention should not be limited thereto.

[0208] The embodiments of the present invention have been described above. The above description is exemplary and not exhaustive, and is not limited to the disclosed embodiments. Many modifications and variations are obvious to those of ordinary skill in the art in the technical field without departing from the scope and spirit of the described embodiments. The choice of terms used herein is intended to best explain the principles of the embodiments, practical applications, or improvements to the technology in the market, or to enable other ordinary skilled persons in the technical field to understand the embodiments disclosed herein.

Claims

1. A compound of formula (A), in, A does not exist or represents a carbonyl group; R1 is selected from C 1-20 Alkyl, C 3-20 Cycloalkyl and C 6-20 Aryl, the alkyl, cycloalkyl or aryl is unsubstituted or substituted by one or more R a replace; R2 is selected from C 1-20 Alkyl and C 3-20 Cycloalkyl, the alkyl or cycloalkyl is unsubstituted or substituted with one or more R a replace; R3 and R4 are each independently selected from C 1-20 Alkyl, -(C=O)-C 1-20 Alkyl, C 3-20 Cycloalkyl, C 6-20 Aryl, -(C=O)-C 6-20 Aryl and 4-20 membered heterocyclic groups, wherein the alkyl, cycloalkyl, aryl or heterocyclic group is unsubstituted or substituted by one or more R b replace; R5 is selected from hydrogen, halogen, cyano, nitro, C 1-20 Alkyl, -(C=O)-C 1-20 Alkyl, C 3-20 Cycloalkyl, C 6-20 Aryl, -(C=O)-C 6-20 Aryl and 4-20 membered heterocyclic groups, wherein the alkyl, cycloalkyl, aryl or heterocyclic group is unsubstituted or substituted by one or more R a replace; Every R a Each independently selected from C 1-20 Alkyl, -OC 1-20 Alkyl, halogenated C 1-20 Alkyl, halogen and cyano; Every R b are independently selected from halogen, nitro, cyano, C 1-20 Alkyl, C 3-20 Cycloalkyl, C 6-20 Aryl, -OC 1-20 Alkyl and halogenated C 1-20 alkyl.

2. The compound according to claim 1, characterized in that The compound is as shown in formula (I) or formula (II): in, R1, R2, R3, R4 and R5 are as defined in claim 1.

3. The compound according to claim 1 or 2, characterized in that R1 is selected from C 1-10 Alkyl, C 3-10 Cycloalkyl and C 6-10 Aryl, the alkyl, cycloalkyl or aryl is unsubstituted or substituted by one or more R a Replace; each R a Each independently selected from C 1-10 Alkyl, -OC 1-10 Alkyl, halogenated C 1-10 Alkyl, halogen and cyano; Preferably, R1 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, n-octyl, isononyl, phenyl, ethylphenyl, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl; More preferably, R1 is selected from methyl and phenyl.

4. The compound according to any one of claims 1 to 3, characterized in that R2 is selected from C 1-10 Alkyl and C 3-10 Cycloalkyl, the alkyl or cycloalkyl is unsubstituted or substituted with one or more R a Replace; each R a Each independently selected from C 1-10 Alkyl, -OC 1-10 Alkyl, halogenated C 1-10 Alkyl, halogen and cyano; Preferably, R2 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, n-octyl, isononyl, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl; More preferably, R2 is selected from methyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, cyclopentyl and cyclohexyl.

5. The compound according to any one of claims 1 to 4, characterized in that R3 and R4 are each independently selected from C 1-10 Alkyl, -(C=O)-C 1-10 Alkyl, C 3-10 Cycloalkyl, C 6-10 Aryl, -(C=O)-C 6-10 Aryl and 4-10 membered heterocyclic groups, wherein the alkyl, cycloalkyl, aryl or heterocyclic group is unsubstituted or substituted by one or more R b Replace; each R b are independently selected from halogen, nitro, cyano, C 1-10 Alkyl, C 3-10 Cycloalkyl, C 6-10 Aryl, -OC 1-10 Alkyl and halogenated C 1-10 alkyl; Preferably, R3 and R4 are each independently selected from C 1-10 Alkyl, -(C=O)-C 1-10 Alkyl, C 3-10 Cycloalkyl, C 6-10 Aryl and -(C=O)-C 6-10 Aryl, the alkyl, cycloalkyl or aryl is unsubstituted or substituted by one or more R b Replace; each R b are independently selected from halogen, nitro, cyano, C 1-10 Alkyl, C 3-10 Cycloalkyl, C 6-10 Aryl, -OC 1-10 Alkyl and halogenated C 1-10 alkyl; More preferably, R3 and R4 are each independently selected from C 1-8 Alkyl, -(C=O)-C 1-8 Alkyl, C 3-8 Cycloalkyl, phenyl and -(C=O)-phenyl, wherein the alkyl, cycloalkyl and phenyl are unsubstituted or substituted with one or more R b Replace; each R b are independently selected from halogen, nitro, cyano, C 1-8 Alkyl, C 3-8 Cycloalkyl, C 6-8 Aryl, -OC 1-8 Alkyl and halogenated C 1-8 alkyl; Further preferably, R3 and R4 are each independently selected from methyl, ethyl, n-propyl, n-butyl, n-pentyl, 4-methylpentyl, 5-methylhexyl, n-heptyl, phenyl, benzyl, benzoyl, cyclopentyl, cyclopentylmethyl and 1-butyryl.

6. The compound according to any one of claims 1 to 5, characterized in that R5 is selected from hydrogen, halogen, cyano, nitro, C 1-20 Alkyl, -(C=O)-C 1-20 Alkyl, C 3-20 Cycloalkyl, C 6-20 Aryl, -(C=O)-C 6-20 Aryl and 4-20 membered heterocyclic group; Preferably, R5 is selected from hydrogen, halogen, cyano, nitro, C 1-10 Alkyl, C 3-10 Cycloalkyl, C 6-10 Aryl and 4- to 10-membered heterocyclic groups; More preferably, R5 is selected from hydrogen, nitro and C 1-10 alkyl; Further preferably, R5 is selected from hydrogen, nitro and methyl.

7. A compound selected from the following compounds:

8. A polymerizable composition comprising the compound according to any one of claims 1 to 7; Preferably, the polymerizable composition further comprises at least one of the following components: a) acrylic resin prepolymer; b) solvent; More preferably, the polymerizable composition comprises the following components in parts by weight: 2-6 parts of the compound according to any one of claims 1 to 7; 94-98 parts of acrylic resin prepolymer; and 100 parts of solvent.

9. A photosensitive composition comprising the compound according to any one of claims 1 to 7; Preferably, the photosensitive composition further comprises at least one of the following components: a) alkali soluble resin; b) photopolymerizable compounds; c) solvent; More preferably, the photosensitive composition comprises the following components in parts by weight: 1-5 parts of the compound according to any one of claims 1-7; 10-20 parts of an alkali-soluble resin; 5-10 parts of a photopolymerizable compound; and 80-100 parts of solvent.

10. A photoresist comprising the following components: i) a compound according to any one of claims 1 to 7; ii) alkali soluble resin; iii) photopolymerizable compounds; iv) auxiliary agents; Preferably, the auxiliary agent is selected from solvents, colorants, fillers, dispersants, antioxidants, ultraviolet absorbers, curing accelerators and thermal polymerization inhibitors.

11. Use of the compound according to any one of claims 1 to 7, the polymerizable composition according to claim 8, the photosensitive composition according to claim 9 or the photoresist according to claim 10 in the field of photocuring.

Images