Anti-reflective coating composition, preparation method and application

Abstract

The present invention belongs to the field of photolithography technology and discloses an anti-reflective coating composition, a preparation method, and an application. The anti-reflective coating composition provided by the present invention contains an aromatic thioepoxy resin, an acid generator, a crosslinking agent, a solvent, and an optional surfactant; the aromatic thioepoxy resin includes structural units derived from aromatic thiodiepoxides and structural units derived from hydroxyalkyl isocyanurates. The key to the present invention is to obtain an aromatic thioepoxy resin by an addition reaction of an aromatic thiodiepoxide with a specific structure and a hydroxyalkyl isocyanurate. When the aromatic thioepoxy resin is used in the field of photolithography as a film-forming resin for an anti-reflective coating composition, it can significantly improve the stability of the refractive index, absorbance, and film thickness. The refractive index, absorbance, and film thickness do not change significantly with prolonged standing time, and the present invention has great application prospects.

Description

Technical Field

[0001] The present invention belongs to the field of photolithography technology, and in particular relates to an anti-reflective coating composition, a preparation method and an application thereof. Background Art

[0002] A photoresist is a photosensitive film used to transfer an image onto a substrate. First, a photoresist coating is formed on the substrate, then exposed to an activating radiation source through a photomask. The photomask has regions that are transparent to the activating radiation and other regions that are opaque to it. The activating radiation causes the exposed photoresist coating to undergo photoinduced or chemical changes, thereby transferring the photomask pattern to the substrate coated with the photoresist. After exposure, the photoresist is developed to produce a patterned image that can be used to selectively process the substrate.

[0003] In microlithography, photoresists are primarily used in the manufacture of semiconductors and integrated circuits. The goal is to transform highly polished semiconductor wafers, such as silicon or gallium arsenide, into a composite matrix with conductive paths for circuit functionality. A suitable photolithography process is crucial to achieving this goal. The entire photolithography process involves multiple steps that interact with each other, but exposure is undoubtedly considered to play a key role in forming high-resolution photoresist images. During 248nm and 193nm photolithography processes, the effect of radiation reflection from the substrate and interference with incident light becomes increasingly pronounced, leading to a more pronounced standing wave effect within the photoresist. This results in uneven photoresist exposure, wavy, jagged edges on the pattern sidewalls, and non-uniform photoresist line widths that cannot be controlled to meet design dimensional requirements. These issues ultimately lead to short circuits and open circuits, ultimately impacting the yield of the photolithography process.

[0004] Providing a bottom anti-reflective coating (BARC) between the photoresist layer and the substrate is the best option for solving the above problems. A bottom anti-reflective coating (BARC) refers to a bottom anti-reflective material added between the photoresist and the substrate that can effectively eliminate the interference standing waves formed by light reflection. This BARC can increase the exposure energy range and focal length, reduce the impact of substrate geometric structure differences on critical dimension uniformity, and simultaneously reduce the circular notches caused by the scattering of reflected light, alleviating the swing curve effect and concave notch effect caused by the different photoresist thicknesses caused by the substrate configuration. Currently, semiconductor and integrated circuit manufacturers are still striving to improve the resolution of photoresist patterns, and therefore have higher requirements for the performance of anti-reflective coating compositions. Currently, isocyanurate compounds are commonly used in anti-reflective coating compositions, but due to their poor stability, their refractive index, absorbance, and film thickness will change significantly with the extension of static time, greatly limiting their application in the field of photoresists. Summary of the Invention

[0005] One of the objectives of the present invention is to overcome the problem of poor self-stability of existing anti-reflective films containing isocyanurate resins and to provide a new anti-reflective coating composition. The anti-reflective coating formed from the composition has good stability in refractive index, absorbance and film thickness.

[0006] Specifically, the anti-reflective coating composition provided by the present invention contains an aromatic thioepoxy resin, an acid generator, a crosslinking agent, a solvent, and an optional surfactant; the aromatic thioepoxy resin includes a structural unit derived from an aromatic thiodiepoxide represented by formula (1) and a structural unit derived from a hydroxyalkyl isocyanurate represented by formula (2);

[0007]

[0008] In formula (1), Ar is an aromatic group, and R1 is selected from H, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a nitro group, a nitroso group, or a halogen group;

[0009] In formula (2), R2 and R3 are each independently selected from C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkylhydroxy, C1-C6 alkylene or C6-C6 alkylene. 20 wherein n is 1 to 10.

[0010] In some specific embodiments, based on the total weight of the anti-reflective film composition, the content of the aromatic thioepoxy resin is 1 to 10 wt %, the content of the acid generator is 0.01 to 2 wt %, the content of the cross-linking agent is 0.01 to 5 wt %, the content of the solvent is 80 to 95 wt %, and the content of the surfactant is 0 to 3 wt %.

[0011] In some specific embodiments, the aromatic thiodiepoxide is prepared according to the following method: S1, condensing the aromatic aldehyde compound represented by formula (3) with 2-mercaptoethanol to obtain an intermediate product; S2, subjecting the intermediate product to a substitution reaction with epichlorohydrin to obtain the aromatic thiodiepoxide;

[0012]

[0013] In formula (3), Ar is an aromatic group, and R1 is selected from H, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a nitro group, a nitroso group, or a halogen group.

[0014] In some specific embodiments, in step S1, the condensation reaction is carried out in the presence of a first catalyst.

[0015] In some specific embodiments, in step S1, the first catalyst is nickel chloride and / or zirconium chloride.

[0016] In some specific embodiments, in step S1, the amount of the first catalyst added is 0.5-2.0% of the total mass of the aromatic aldehyde compound and 2-mercaptoethanol.

[0017] In some specific embodiments, in step S1, the molar ratio of the aromatic aldehyde compound to 2-mercaptoethanol is 1:(2-2.5).

[0018] In some specific embodiments, in step S1, the condensation reaction temperature is 20-35° C., and the time is 1-2 hours.

[0019] In some specific embodiments, in step S1, the structure of the intermediate product is as shown in formula (4):

[0020]

[0021] In formula (4), Ar is an aromatic group, and R1 is selected from H, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a nitro group, a nitroso group, or a halogen group.

[0022] In some specific embodiments, in step S2, the substitution reaction is carried out in the presence of a second catalyst.

[0023] In some specific embodiments, in step S2, the second catalyst is tetrabutylammonium chloride and / or tetrabutylammonium bromide.

[0024] In some specific embodiments, in step S2, the amount of the second catalyst added is 0.1 to 3.0% of the total mass of the intermediate product and epichlorohydrin.

[0025] In some specific embodiments, in step S2, the input mass ratio of the intermediate product to epichlorohydrin is 1:(2.0-3.0).

[0026] In some specific embodiments, in step S2, the substitution reaction is carried out at a temperature of 25 to 45° C. and for a time of 4 to 12 hours.

[0027] In some specific embodiments, the hydroxyalkyl isocyanurate is selected from at least one of 1,3,5-tris(2-hydroxyethyl)isocyanurate, 1-allyl-3,5-bis(2-hydroxyethyl)isocyanurate, 1-(2-hydroxyethyl)-3,5-diethylisocyanurate, 1-(2-cyclohexylethyl)-3,5-bis(2-hydroxyethyl)isocyanurate and 1,3,5-tris(2-hydroxyethyl)isocyanurate.

[0028] In some specific embodiments, the molar ratio of the structural units derived from the aromatic thiodiepoxide represented by formula (1) to the structural units derived from the hydroxyalkyl isocyanurate represented by formula (2) in the aromatic thioepoxy resin is 1:(1-3).

[0029] In some specific embodiments, the aromatic thioepoxy resin has a weight average molecular weight of 2000 to 15000 Da and a polydispersity index (PDI) of 1.2 to 3.2.

[0030] In some specific embodiments, the aromatic thioepoxy resin is prepared by performing an addition reaction between an aromatic thiodiepoxide and an aromatic thiodiepoxide.

[0031] In some specific embodiments, the molar ratio of the aromatic thiodiepoxide to the aromatic thiodiepoxide is 1:(1-3).

[0032] In some specific embodiments, the temperature of the addition reaction is 80-130° C., and the time is 2-48 hours.

[0033] In some specific embodiments, the acid generator is selected from at least one of a sulfonium salt compound, an iodonium salt organic compound, and an organic sulfonic acid compound.

[0034] In some specific embodiments, the cross-linking agent is selected from at least one of tetramethoxymethyl glycoluril, hexamethoxymethyl melamine, tetramethoxymethyl benzoguanamine, 1,3,4,6-tetrakis(butoxymethyl) glycoluril, 1,3,4,6-tetrakis(hydroxymethyl) glycoluril, 1,3-bis(hydroxymethyl)urea, N-hydroxymethyl acrylamide, N-methoxymethyl methacrylamide and N-ethoxymethyl acrylamide.

[0035] In some specific embodiments, the surfactant is selected from fluorinated surfactants and / or non-fluorinated surfactants.

[0036] In some specific embodiments, the solvent is selected from at least one of methyl 2-hydroxyisobutyrate, cyclohexanone, cyclopentanone, butyrolactone, dimethylacetamide, dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, tetrahydrofurfuryl alcohol, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate and ethyl lactate.

[0037] A second object of the present invention is to provide a method for preparing the above-mentioned anti-reflective coating composition, which comprises uniformly mixing an aromatic thioepoxy resin, an acid generator, a crosslinking agent, a solvent, and an optional surfactant.

[0038] A third object of the present invention is to provide an application of the anti-reflective coating composition in the field of photolithography.

[0039] The key to the present invention lies in the use of an aromatic thiodiepoxide with a specific structure and a hydroxyalkyl isocyanurate to form an aromatic thioepoxy resin through an addition reaction. Specifically, the aromatic thioepoxy resin comprises structural units derived from the aromatic thiodiepoxide and structural units derived from the hydroxyalkyl isocyanurate. When the aromatic thioepoxy resin is used as a film-forming resin in an anti-reflective coating composition, it can significantly improve the stability of the refractive index, absorbance, and film thickness. The refractive index, absorbance, and film thickness do not change significantly with prolonged standing time, thus showing great application prospects. DETAILED DESCRIPTION

[0040] Existing isocyanurate resins are commonly used as the primary material for anti-reflection coatings in photolithography due to their unique structure, effectively reducing reflections while increasing exposure energy range and focal length. However, isocyanurate resins also have poor inherent stability, significantly limiting their application in photoresists.

[0041] To address the problems existing in prior art isocyanurate resins, the inventors of the present invention, through in-depth and extensive research and numerous experiments, have discovered that an aromatic thioepoxy resin obtained by reacting a uniquely structured aromatic thiodiepoxide with a hydroxyalkyl isocyanurate for addition reaction exhibits excellent stability compared to existing isocyanurate resins in that, when used as a film-forming resin for an anti-reflective coating, the resulting anti-reflective coating exhibits minimal changes in refractive index, absorbance, and film thickness with prolonged standing time.

[0042] The anti-reflective coating composition provided by the present invention contains an aromatic thioepoxy resin, an acid generator, a crosslinking agent, a solvent, and an optional surfactant. Based on the total weight of the anti-reflective film composition, the content of the aromatic thioepoxy resin is preferably 1 to 10 wt%, such as 1 wt%, 2 wt%, 4 wt%, 6 wt%, 8 wt%, 10 wt%, or any value therebetween; the content of the acid generator is preferably 0.01 to 2 wt%, such as 0.01 wt%, 0.05 wt%, 0.1 wt%, 0.5 wt%, 1 wt%, 1.5 wt%, 2 wt%, or any value therebetween; the content of the crosslinking agent is preferably 0.01 to 5 wt%, such as 0.01 wt%, 0.05 wt%, 0.1 wt%, or any value therebetween. %, 0.5wt%, 1wt%, 1.5wt%, 2wt%, 2.5wt%, 3wt%, 3.5wt%, 4wt%, 4.5wt%, 5wt% or any value therebetween; the content of the solvent is preferably 80-95wt%, such as 80wt%, 82wt%, 85wt%, 87wt%, 90wt%, 92wt%, 95wt% or any value therebetween; the content of the surfactant is preferably 0-3wt%, such as 0, 0.5wt%, 1wt%, 1.5wt%, 2wt%, 2.5wt%, 3wt% or any value therebetween.

[0043] In the present invention, the aromatic thioepoxy resin comprises structural units derived from an aromatic thiodiepoxide and structural units derived from a hydroxyalkyl isocyanurate, wherein the molar ratio of the structural units derived from the aromatic thiodiepoxide to the structural units derived from the hydroxyalkyl isocyanurate is 1:(1-3), such as 1:1, 1:1.5, 1:2, 1:2.5, 1:3, or any value therebetween.

[0044] In the present invention, the aromatic thiodiepoxide has a structure shown in formula (1):

[0045]

[0046] In formula (1), Ar is an arylene group, and R1 is selected from H, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a nitro group, a nitroso group, or a halogen. Specific examples of arylene groups include, but are not limited to, a phenylene ring or a naphthalene ring. Specific examples of C1-C6 alkyl groups include, but are not limited to, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a tert-pentyl group, or a neopentyl group. Specific examples of C1-C6 haloalkyl groups include, but are not limited to, bromomethyl, bromoethyl, bromo-n-propyl, bromo-i-propyl, bromo-n-butyl, bromo-sec-butyl, bromo-i-butyl, bromo-t-butyl, bromo-n-pentyl, bromo-i-pentyl, bromo-t-pentyl, bromo-neopentyl, chloromethyl, chloroethyl, chloro-n-propyl, chloro-i-propyl, chloro-n-butyl, chloro-sec-butyl, chloro-i-butyl, chloro-t-butyl, chloro-n-pentyl, chloro-i-pentyl, chloro-t-pentyl, chloro-neopentyl, fluoromethyl, fluoroethyl, fluoro-n-propyl, fluoro-i-propyl, fluoro-n-butyl, fluoro-sec-butyl, fluoro-i-butyl, fluoro-t-butyl, fluoro-n-pentyl, fluoro-i-pentyl, fluoro-t-pentyl, or fluoro-neopentyl. Specific examples of C1-C6 alkoxy include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, n-pentoxy, isopentoxy, tert-pentoxy, or neopentoxy. Specific examples of halogen include, but are not limited to, fluorine, chlorine, bromine, or iodine.

[0047] In some specific embodiments, the aromatic thiodiepoxide has at least one of the compounds represented by formulas (1-1) to (1-6):

[0048]

[0049] In the present invention, the aromatic thiodiepoxide can be directly purchased from the market, synthesized by a chemical synthesis company, or synthesized by itself, and the acquisition method does not limit the present invention.

[0050] In the present invention, a method for preparing an aromatic thiodiepoxide is exemplarily provided, the method comprising: S1, subjecting an aromatic aldehyde compound represented by formula (3) to a condensation reaction with 2-mercaptoethanol to obtain an intermediate product; S2, subjecting the intermediate product to a substitution reaction with epichlorohydrin to obtain an aromatic thiodiepoxide;

[0051]

[0052] In formula (3), Ar is an aromatic group, and R1 is selected from H, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a nitro group, a nitroso group, or a halogen group.

[0053] In the preparation process of the aromatic thiodiepoxide, the structure of the aromatic aldehyde compound is adaptively selected according to the desired aromatic thiodiepoxide, and specifically can be, but is not limited to, at least one of the compounds represented by formulas (3-1) to (3-6):

[0054]

[0055] In the above-mentioned preparation process of the aromatic thiodiepoxide, in step S1, the aromatic aldehyde compound and 2-mercaptoethanol are added to the reaction system in a certain molar ratio for reaction, and the specific molar ratio between the two is limited to enable the corresponding condensation reaction to occur. In some specific embodiments, in order to reduce the formation of reaction by-products and increase the yield of the intermediate product, the molar ratio of the aromatic aldehyde compound to 2-mercaptoethanol is preferably 1:(2.0-2.5), and can specifically be 1:2.0, 1:2.1, 1:2.2, 1:2.3, 1:2.4, 1:2.5 or any value therebetween.

[0056] In the preparation process of the above-mentioned aromatic thiodiepoxide, in step S1, the aromatic aldehyde compound and 2-mercaptoethanol undergo a condensation reaction in the presence of a first catalyst. The first catalyst is a compound that can catalyze the reaction of sulfhydryl and carbonyl groups, and can be, but not limited to, nickel chloride or its hydrate, zirconium chloride or its hydrate, or a mixture of two or more of the above substances. In addition, the amount of the first catalyst added is limited to being able to catalyze the corresponding condensation reaction. In some specific embodiments, in order to improve the efficiency of the condensation reaction, the amount of the first catalyst added is preferably 0.5 to 2.0% of the total mass of the aromatic aldehyde compound and 2-mercaptoethanol, and can be, but not limited to, 0.5%, 0.6%, 0.7%, 0.9%, 1.0%, 1.3%, 1.5%, 1.8%, 2.0% or any value therebetween.

[0057] In the preparation process of the above-mentioned aromatic thiodiepoxide, in step S1, the reaction temperature of the aromatic aldehyde compound and 2-mercaptoethanol is limited to the corresponding condensation reaction, and the reaction time is limited to the reaction of the reactants at least partially or completely. In some specific embodiments, in order to reduce the formation of reaction by-products and improve the yield of intermediates, the temperature of the condensation reaction is preferably controlled to be 20 to 35 ° C, specifically but not limited to 20 ° C, 23 ° C, 25 ° C, 27 ° C, 30 ° C, 31 ° C, 32 ° C, 35 ° C or any value therebetween; the time of the condensation reaction is adaptively adjusted as the temperature changes, preferably controlled to be 1 to 2 h, specifically but not limited to 1 h, 1.2 h, 1.4 h, 1.6 h, 1.8 h, 2 h or any value therebetween.

[0058] In the preparation process of the aromatic thiodiepoxide, in step S1, the aromatic aldehyde compound and 2-mercaptoethanol undergo polycondensation to obtain an intermediate product having a structure as shown in formula (4) or mainly containing a compound having a structure as shown in formula (4);

[0059]

[0060] In formula (4), Ar is an aromatic group, and R1 is selected from H, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a nitro group, a nitroso group, or a halogen group.

[0061] In some specific embodiments, different intermediate products can be obtained according to the different aromatic aldehyde compounds added. The intermediate product can be more specifically, but not limited to, at least one of the compounds represented by formulas (4-1) to (4-6):

[0062]

[0063] In the preparation process of aromatic thiodiepoxide, in step S2, the intermediate product and epichlorohydrin are added to the reaction system in a certain molar ratio for reaction. The specific molar ratio of the two is limited to enable the corresponding substitution reaction to occur. In some specific embodiments, in order to reduce the formation of reaction by-products and increase the yield of aromatic thiodiepoxide, the molar ratio of the intermediate product to epichlorohydrin is preferably 1:(2.0-3.0), specifically 1:2.0, 1:2.1, 1:2.2, 1:2.3, 1:2.4, 1:2.5, 1:3.0 or any value therebetween.

[0064] In the preparation process of aromatic thiodiepoxide, in step S2, the intermediate product and epichlorohydrin undergo a substitution reaction in the presence of a second catalyst. The second catalyst is a compound that can catalyze the substitution reaction between a hydroxyl group and a halogenated hydrocarbon, and can specifically be tetrabutylammonium chloride, tetrabutylammonium bromide, or a mixture of the two. In addition, the amount of the second catalyst added is limited to being able to catalyze the corresponding substitution reaction. In some specific embodiments, in order to improve the efficiency of the substitution reaction, the amount of the second catalyst added is preferably 0.1% to 3.0%, specifically but not limited to 0.1%, 0.5%, 0.8%, 1.0%, 1.5%, 2.0%, 2.5%, 3.0% or any value therebetween.

[0065] In the preparation process of aromatic thiodiepoxide, in step S2, the reaction temperature of the intermediate product and epichlorohydrin is limited to the temperature at which the corresponding substitution reaction can occur, and the reaction time is limited to the temperature at which the reactants can at least partially or completely react. In some specific embodiments, in order to reduce the formation of reaction by-products and increase the yield of aromatic thiodiepoxide, the temperature of the substitution reaction is preferably controlled to be 25 to 45°C, specifically but not limited to 25°C, 27°C, 30°C, 37°C, 35°C, 40°C, 32°C, 45°C or any value therebetween; the time of the substitution reaction is adaptively adjusted as the temperature changes, preferably controlled to be 4 to 12h, specifically but not limited to 4h, 6h, 8h, 10h, 12h or any value therebetween.

[0066] In the present invention, the hydroxyalkyl isocyanurate has a structure shown in formula (2):

[0067]

[0068] In formula (2), R2 and R3 are each independently selected from C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkylhydroxy, C1-C6 alkylene or C6-C6 alkylene. 20 wherein n is 1 to 10. Specific examples of C1 to C6 alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, tert-pentyl, or neopentyl. Specific examples of C1-C6 haloalkyl groups include, but are not limited to, bromomethyl, bromoethyl, bromo-n-propyl, bromo-i-propyl, bromo-n-butyl, bromo-sec-butyl, bromo-i-butyl, bromo-t-butyl, bromo-n-pentyl, bromo-i-pentyl, bromo-t-pentyl, bromo-neopentyl, chloromethyl, chloroethyl, chloro-n-propyl, chloro-i-propyl, chloro-n-butyl, chloro-sec-butyl, chloro-i-butyl, chloro-t-butyl, chloro-n-pentyl, chloro-i-pentyl, chloro-t-pentyl, chloro-neopentyl, fluoromethyl, fluoroethyl, fluoro-n-propyl, fluoro-i-propyl, fluoro-n-butyl, fluoro-sec-butyl, fluoro-i-butyl, fluoro-t-butyl, fluoro-n-pentyl, fluoro-i-pentyl, fluoro-t-pentyl, or fluoro-neopentyl. Specific examples of C1-C6 alkoxy groups include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, n-pentoxy, isopentoxy, tert-pentoxy, or neopentoxy. Specific examples of C1-C6 alkenyl groups include, but are not limited to, ethenyl, propenyl, propenyl, 1-butenyl, or 2-butenyl. 20 Specific examples of the aryl group include, but are not limited to, phenyl, benzyl, phenethyl, tolyl, ethylphenyl, xylyl, or diethylphenyl.

[0069] In the present invention, the hydroxyalkyl isocyanurate may specifically be but is not limited to at least one of 1,3,5-tris(2-hydroxyethyl)isocyanurate, 1-allyl-3,5-bis(2-hydroxyethyl)isocyanurate, 1-(2-hydroxyethyl)-3,5-diethylisocyanurate, 1-(2-cyclohexylethyl)-3,5-bis(2-hydroxyethyl)isocyanurate and 1,3,5-tris(2-hydroxyethyl)isocyanurate.

[0070] In the present invention, the weight-average molecular weight of the aromatic thioepoxy resin is preferably 2000 to 15000 Da, and specifically can be 2000 Da, 2500 Da, 5000 Da, 7500 Da, 10000 Da, 12000 Da, 15000 Da, or any value therebetween. In some preferred embodiments, the weight-average molecular weight of the aromatic thioepoxy resin is 3000 to 12000 Da. When the aromatic thioepoxy resin is used as the primary film-forming substance in an anti-reflective coating composition, it can exhibit better stability, refractive index, and etch rate.

[0071] In the present invention, the polydispersity PDI of the aromatic thioepoxy resin is preferably 1.2 to 3.2, and specifically can be but not limited to 1.2, 1.5, 1.8, 2.0, 2.5, 2.9, 3.0, 3.2 or any value therebetween.

[0072] In the present invention, the aromatic thioepoxy resin is prepared by reacting an aromatic thiodiepoxide with a hydroxyalkyl isocyanurate through an addition reaction. The specific types of the aromatic thiodiepoxide and the hydroxyalkyl isocyanurate and their methods of obtaining have been described above and will not be repeated here.

[0073] During the preparation of the aromatic thioepoxy resin, the aromatic thiodiepoxide and hydroxyalkyl isocyanurate are added to the reaction system in a specific molar ratio to react. The specific molar ratio is limited to the amount that allows the corresponding addition reaction to occur. In some specific embodiments, in order to reduce the formation of reaction by-products and increase the yield of the aromatic thioepoxy resin, the molar ratio of the aromatic thiodiepoxide to hydroxyalkyl isocyanurate is preferably 1:(1-3), and can be, but is not limited to, 1:1.0, 1:1.1, 1:2.2, 1:2.3, 1:2.5, 1:3.0, or any value therebetween.

[0074] In the preparation process of the aromatic thioepoxy resin, the reaction temperature of the aromatic thiodiepoxide and the hydroxyalkyl isocyanurate is limited to the temperature at which the corresponding addition reaction can occur, and the reaction time is limited to the temperature at which the reactants can at least partially or completely react. In some specific embodiments, in order to reduce the formation of reaction by-products and increase the yield of intermediate products, the temperature of the addition reaction is preferably controlled at 80 to 130°C, specifically but not limited to 80°C, 85°C, 90°C, 100°C, 105°C, 120°C, 125°C, 130°C or any value therebetween; the time of the addition reaction is adaptively adjusted as the temperature changes, and is preferably controlled at 2 to 48 hours, such as 2 hours, 5 hours, 10 hours, 15 hours, 20 hours, 25 hours, 30 hours, 35 hours, 40 hours, 45 hours, 48 hours or any value therebetween.

[0075] In some specific embodiments, the acid generator may be selected from, but not limited to, at least one of a sulfonium salt compound, an iodonium salt organic compound, and an organic sulfonic acid compound.

[0076] In some specific embodiments, the cross-linking agent can be, but is not limited to, at least one of tetramethoxymethyl glycoluril, hexamethoxymethyl melamine, tetramethoxymethyl benzoguanamine, 1,3,4,6-tetrakis(butoxymethyl) glycoluril, 1,3,4,6-tetrakis(hydroxymethyl) glycoluril, 1,3-bis(hydroxymethyl)urea, N-hydroxymethyl acrylamide, N-methoxymethyl methacrylamide and N-ethoxymethyl acrylamide.

[0077] In some specific embodiments, the surfactant can be, but is not limited to, a fluorinated surfactant, a non-fluorinated surfactant, or a mixture thereof.

[0078] In some specific embodiments, the solvent can be, but is not limited to, at least one of 2-hydroxyisobutyric acid methyl ester, cyclohexanone, cyclopentanone, butyrolactone, dimethylacetamide, dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, tetrahydrofurfuryl alcohol, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate and ethyl lactate.

[0079] The method for preparing the anti-reflective coating composition provided by the present invention comprises uniformly mixing an aromatic thioepoxy resin, an acid generator, a crosslinking agent, a solvent, and an optional surfactant. The specific types and amounts of the aromatic thioepoxy resin, the acid generator, the crosslinking agent, the solvent, and the surfactant have been described above and are not further elaborated here.

[0080] The present invention also provides application of the above anti-reflective coating composition in the field of photolithography.

[0081] In the present invention, when the aromatic thioepoxy resin is actually used in pattern forming in the field of photolithography, the specific pattern forming process includes: applying the anti-reflective coating composition containing at least the aromatic thioepoxy resin to a substrate and performing a heat treatment to form a bottom anti-reflective coating on the substrate; forming a photoresist layer on the bottom anti-reflective coating, and exposing and developing the photoresist layer to form a photoresist pattern.

[0082] The embodiments of the present invention are described in detail below. The examples of the embodiments are intended to explain the present invention and are not to be construed as limiting the present invention. Where specific techniques or conditions are not specified in the embodiments, they are performed according to the techniques or conditions described in the literature in this area or according to the product specifications. Reagents or instruments used that do not specify the manufacturer are all conventional products that can be obtained commercially.

[0083] Synthesis example

[0084] This synthesis example is used to illustrate the synthesis of aromatic thiodiepoxides, which specifically includes the following steps:

[0085] S1. Benzaldehyde (0.2 mol, 21.22 g) and 2-mercaptoethanol (0.4 mol, 31.25 g) were mixed uniformly, and then the catalyst NiCl2·6H2O (0.001 mol, 0.24 g) was added and continued to mix uniformly. The resulting solution was stirred and reacted at 20°C for 2 h; then 100 mL of dichloromethane was added, and the catalyst was filtered to remove the catalyst to obtain a liquid product, which was concentrated by vacuum distillation and purified by silica gel (200-300 mesh) column chromatography to obtain intermediate 1, which was a white solid.

[0086] S2. The intermediate product 1 (48.9 g, 0.2 mol), epichlorohydrin (46.7 mL, 0.6 mol), NaOH (24 g, 0.6 mol), tetrabutylammonium chloride (3.2 g, 0.01 mol) and pure water (10 mL, 0.56 mol) were mixed at room temperature, and the mixture was stirred at 35°C for 8 h. The solid residue was removed by filtration, and the filtrate was washed with dichloromethane solvent; the filtrate obtained by combining the washings was concentrated by reduced pressure distillation, and purified by silica gel (200-300 mesh) column chromatography to obtain aromatic thiodiepoxide (monomer 1).

[0087] The reactions occurring in the above steps S1 and S2 are specifically as follows:

[0088]

[0089] The monomer 1 was subjected to nuclear magnetic resonance and mass spectrometry detection, and the results were as follows:

[0090] MRI test results: 1H-NMR(400MHz, CDCl3)δ(ppm)7.48-7.12(m,4H,PhH),5.12(s,1H,-SCHS-),3.78-3.32(m,8H,-CH2OCH2-),3.16-3.12(m,2H,ring CH),2.85-2.78(m,4H,-SCH2),2.75-2.60(m,4H,ring CH2). 13 C-NMR (100MHz, CDCl3) δ (ppm) 140.22, 128.54, 127.98, 127.72, 71.53, 70.96, 70.94, 53.85, 50.73, 44.16, 31.73.

[0091] Mass spectrometry detection results: HRMS (ESI): m / z calcd.For C 17 H 24 O4S2(M+)356.11; found=379.10([M+Na] + ,100).

[0092] This indicates that the aromatic thiodiepoxide obtained in this synthesis example is indeed the monomer 1 having the structure represented by formula (1).

[0093] Comparative Synthesis Example

[0094] S1. Heptanal (0.2 mol, 22.838 g) and 2-mercaptoethanol (0.4 mol, 31.25 g) were mixed uniformly, and then the catalyst NiCl2·6H2O (0.001 mol, 0.24 g) was added and continued to mix uniformly. The resulting solution was stirred and reacted at 20°C for 2 h; then 100 mL of dichloromethane was added, and the catalyst was filtered to remove the catalyst to obtain a liquid product, which was concentrated by vacuum distillation and purified by silica gel (200-300 mesh) column chromatography to obtain intermediate 2.

[0095] S2. All the intermediate products 2, epichlorohydrin (46.7 mL, 0.6 mol), NaOH (24 g, 0.6 mol), tetrabutylammonium chloride (3.2 g, 0.01 mol) and pure water (10 mL, 0.56 mol) were mixed at room temperature, and the mixture was stirred at 35°C for 8 h. The solid residue was removed by filtration, and the filtrate was washed with dichloromethane solvent; the filtrate obtained by combining the washings was concentrated by reduced pressure distillation, and purified by silica gel (200-300 mesh) column chromatography to obtain thiodiepoxide.

[0096] Preparation Example 1

[0097] This preparation example is used to illustrate the preparation of aromatic thioepoxy resin, which specifically includes the following steps:

[0098] (1) At room temperature, 46.3 g of aromatic thiodiepoxide (prepared by the synthesis example), 101.9 g of 1,3,5-tris(2-hydroxyethyl)isocyanurate, 5.9 g of 25 wt% tetramethylammonium hydroxide aqueous solution and 315 g of propylene glycol monomethyl ether acetate (PGMEA) were added to a 500 mL three-necked flask equipped with a thermometer, a mechanical stirrer, a reflux condenser and a water separator; under nitrogen protection, the temperature was raised to 100° C., and after the reactants were completely dissolved, the reaction system began to reflux and the reaction timer was set, and the reaction was reacted for 12 h; the reaction system was cooled to room temperature to obtain a reaction solution containing aromatic thioepoxy resin.

[0099] (2) PGMEA was added to the reaction solution for dilution, and the diluted reaction solution was slowly added to a methanol / water mixed solvent (volume ratio of 1:1, the same below) and stirred for 30 minutes to precipitate the precipitate, filtered, and the above operation was repeated twice; then, PGMEA in an amount twice as much as the reaction input was added to dissolve the precipitate and shaken evenly, and the water was removed by vacuum distillation to obtain an aromatic thioepoxy resin.

[0100] After testing, the weight average molecular weight M of the aromatic thioepoxy resin obtained in this preparation example is w The molecular weight distribution PDI is 1.88.

[0101] Preparation Example 2

[0102] This preparation example is used to illustrate the preparation of aromatic thioepoxy resin, which specifically includes the following steps:

[0103] (1) At room temperature, 42.8 g of aromatic thiodiepoxide (prepared by the synthesis example), 92.6 g of 1-allyl-3,5-bis(2-hydroxyethyl)isocyanurate, 5.4 g of a 25 wt% aqueous solution of tetramethylammonium hydroxide, and 288 g of propylene glycol monomethyl ether acetate (PGMEA) were added to a 500 mL three-necked flask equipped with a thermometer, a mechanical stirrer, a reflux condenser, and a water separator; under nitrogen protection, the temperature was raised to 100° C., and after the reactants were completely dissolved, the reaction system began to reflux and the reaction timer was set, and the reaction was continued for 12 h; the reaction system was cooled to room temperature to obtain a reaction solution containing aromatic thioepoxy resin.

[0104] (2) PGMEA was added to the reaction solution for dilution, and the diluted reaction solution was slowly added to a methanol / water mixed solvent and stirred for 30 minutes to precipitate a precipitate, which was filtered and repeated twice; then, PGMEA in an amount twice as large as the reaction input amount was added to dissolve the precipitate and shaken evenly, and water was removed by vacuum distillation to obtain an aromatic thioepoxy resin.

[0105] After testing, the weight average molecular weight M of the aromatic thioepoxy resin obtained in this preparation example is w The molecular weight distribution PDI is 1.81.

[0106] Preparation Example 3

[0107] This preparation example is used to illustrate the preparation of aromatic thioepoxy resin, which specifically includes the following steps:

[0108] (1) At room temperature, 44.5 g of aromatic thiodiepoxide (prepared by the synthesis example), 96.5 g of 1-(2-hydroxyethyl)-3,5-diethylisocyanurate, 5.6 g of a 25 wt % aqueous solution of tetramethylammonium hydroxide, and 300 g of propylene glycol monomethyl ether acetate (PGMEA) were added to a 500 mL three-necked flask equipped with a thermometer, a mechanical stirrer, a reflux condenser, and a water separator; under nitrogen protection, the temperature was raised to 100° C., and after the reactants were completely dissolved, the reaction system began to reflux and the reaction timer was set, and the reaction was continued for 12 h; the reaction system was cooled to room temperature to obtain a reaction solution containing aromatic thioepoxy resin.

[0109] (2) PGMEA was added to the reaction solution for dilution, and the diluted reaction solution was slowly added to a methanol / water mixed solvent and stirred for 30 minutes to precipitate a precipitate, which was filtered and repeated twice; then, PGMEA in an amount twice as large as the reaction input amount was added to dissolve the precipitate and shaken evenly, and water was removed by vacuum distillation to obtain an aromatic thioepoxy resin.

[0110] After testing, the weight average molecular weight M of the aromatic thioepoxy resin obtained in this preparation example is w The molecular weight distribution PDI is 1.93.

[0111] Preparation Example 4

[0112] This preparation example is used to illustrate the preparation of aromatic thioepoxy resin, which specifically includes the following steps:

[0113] (1) At room temperature, 39.2 g of aromatic thiodiepoxide (prepared by the synthesis example), 108.0 g of 1-(2-cyclohexylethyl)-3,5-bis(2-hydroxyethyl)isocyanurate, 5.9 g of a 25 wt% aqueous solution of tetramethylammonium hydroxide, and 313 g of propylene glycol monomethyl ether acetate (PGMEA) were added to a 500 mL three-necked flask equipped with a thermometer, a mechanical stirrer, a reflux condenser, and a water separator; under nitrogen protection, the temperature was raised to 100° C., and after the reactants were completely dissolved, the reaction system began to reflux and the reaction timer was set, and the reaction was continued for 12 h; the reaction system was cooled to room temperature to obtain a reaction solution containing aromatic thioepoxy resin.

[0114] (2) PGMEA was added to the reaction solution for dilution, and the diluted reaction solution was slowly added to a methanol / water mixed solvent and stirred for 30 minutes to precipitate a precipitate, which was filtered and repeated twice; then, PGMEA in an amount twice as large as the reaction input amount was added to dissolve the precipitate and shaken evenly, and water was removed by vacuum distillation to obtain an aromatic thioepoxy resin.

[0115] After testing, the weight average molecular weight M of the aromatic thioepoxy resin obtained in this preparation example is w The molecular weight distribution PDI is 1.84.

[0116] Preparation Example 5

[0117] This preparation example is used to illustrate the preparation of aromatic thioepoxy resin, which specifically includes the following steps:

[0118] (1) At room temperature, 28.5 g of aromatic thiodiepoxide (prepared by the synthesis example), 16.0 g of dimethyl 1,4-cyclohexanedicarboxylate, 104.5 g of 1,3,5-tris(2-hydroxyethyl)isocyanurate, 6.0 g of a 25 wt % aqueous solution of tetramethylammonium hydroxide, and 317 g of propylene glycol monomethyl ether acetate (PGMEA) were added to a 500 mL three-necked flask equipped with a thermometer, a mechanical stirrer, a reflux condenser, and a water separator; under nitrogen protection, the temperature was raised to 100° C., and after the reactants were completely dissolved, the reaction system began to reflux and the reaction timer was set, and the reaction was continued for 12 h; the reaction system was cooled to room temperature to obtain a reaction solution containing aromatic thioepoxy resin.

[0119] (2) PGMEA was added to the reaction solution for dilution, and the diluted reaction solution was slowly added to a methanol / water mixed solvent and stirred for 30 minutes to precipitate a precipitate, which was filtered and repeated twice; then, PGMEA in an amount twice as large as the reaction input amount was added to dissolve the precipitate and shaken evenly, and water was removed by vacuum distillation to obtain an aromatic thioepoxy resin.

[0120] After testing, the weight average molecular weight M of the aromatic thioepoxy resin obtained in this preparation example is w The molecular weight distribution PDI is 1.96.

[0121] Comparative Preparation Example 1

[0122] This comparative preparation example prepared an aromatic thioepoxy resin according to the method provided in Preparation Example 1, except that in step (1), an equimolar mass of thiodiepoxide (prepared in the comparative synthesis example) was used instead of the aromatic thiodiepoxide, and other conditions were the same to obtain a reference thioepoxy resin. The weight average molecular weight M of the reference thioepoxy resin was determined to be w The molecular weight distribution PDI is 5663 and 2.01.

[0123] Comparative Preparation Example 2

[0124] This comparative preparation example prepared an aromatic thioepoxy resin according to the method provided in Preparation Example 1, except that in step (1), an equimolar mass of 4-phenyl-1,7-heptadioxirane was used instead of aromatic thiodiepoxide, and other conditions were the same to obtain a reference aromatic thioepoxy resin. After testing, the weight average molecular weight M of the reference aromatic thioepoxy resin was w The molecular weight distribution PDI is 1.92.

[0125] Comparative Preparation Example 3

[0126] This comparative preparation example prepared an aromatic thioepoxy resin according to the method provided in Preparation Example 3, except that in step (1), an equimolar mass of 4-phenyl-1,7-heptadioxirane was used instead of an aromatic thiodiepoxide, and other conditions were the same to obtain a reference thioepoxy resin. After testing, the weight average molecular weight M of the reference thioepoxy resin was w The molecular weight distribution PDI is 1.95.

[0127] Comparative Preparation Example 4

[0128] This comparative preparation example prepared an aromatic thioepoxy resin according to the method provided in Preparation Example 5, except that in step (1), an equimolar mass of 4-phenyl-1,7-heptadioxirane was used instead of an aromatic thiodiepoxide, and other conditions were the same to obtain a reference aromatic thioepoxy resin. After testing, the weight average molecular weight M of the reference aromatic thioepoxy resin was w The molecular weight distribution PDI is 5608 and 2.00.

[0129] Examples and Comparative Examples 1 to 4

[0130] The aromatic thioepoxy resins of Preparation Examples 1 to 5 and the aromatic epoxy resins of Comparative Preparation Examples 1 to 4 were added to a clean bottle with a solvent, an acid generator, and an additive according to the ratios in Table 1. The mixture was shaken until all components were completely dissolved. Then, each sample was filtered through a 0.2 μm PTFE membrane filter and placed in a new clean bottle to obtain an anti-reflective coating composition.

[0131] Table 1. Composition of anti-reflective coating compositions (wt%)

[0132]

[0133] The acid generator is p-toluenesulfonic acid, the cross-linking agent is tetramethoxymethyl glycoluril, and the solvent is propylene glycol monomethyl ether acetate (PGMEA).

[0134] Test Case

[0135] The anti-reflective coating compositions of the above examples and comparative examples were spin-coated onto the etching layer of the silicon wafer and baked at 200° C. for 60 seconds to form a film with a thickness of Anti-reflective coating.

[0136] (1) Film thickness: The initial (immediately after preparation) film thickness of the anti-reflective coating and the film thickness after 6 months at room temperature were measured using a film thickness meter (purchased from KLA). The test results are shown in Table 1.

[0137] (2) Refractive index n: The initial refractive index of the antireflective coating and the refractive index after 6 months at room temperature were measured using an ellipsometer (purchased from Woollman). The test results are shown in Table 1.

[0138] (3) Absorbance k: The initial absorbance of the antireflection coating and the absorbance after 6 months at room temperature were tested using an etching device TE-8500P (purchased from TEL). The test results are shown in Table 1.

[0139] Table 1

[0140]

[0141] From the results in Table 1, it can be seen that the bottom anti-reflection composition provided by the present invention has almost no change in film thickness, refractive index k and absorbance n after being placed at room temperature for 6 months, and has better self-stability than the comparative example.

[0142] Although the embodiments of the present invention have been shown and described above, it will be understood that the above embodiments are illustrative and are not to be construed as limitations on the present invention. A person skilled in the art may change, modify, replace and modify the above embodiments within the scope of the present invention without departing from the principles and purpose of the present invention.

Claims

1. An anti-reflective coating composition, characterized in that The anti-reflective coating composition contains an aromatic thioepoxy resin, an acid generator, a crosslinking agent, a solvent, and an optional surfactant; the aromatic thioepoxy resin includes a structural unit derived from an aromatic thiodiepoxide represented by formula (1) and a structural unit derived from a hydroxyalkyl isocyanurate represented by formula (2); In formula (1), Ar is an aromatic group, and R1 is selected from H, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a nitro group, a nitroso group, or a halogen group; In formula (2), R2 and R3 are each independently selected from C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkylhydroxy, C1-C6 alkylene or C6-C6 alkylene. 20 wherein n is 1 to 10.

2. The anti-reflective coating composition according to claim 1, wherein Based on the total weight of the anti-reflective coating composition, the content of the aromatic thioepoxy resin is 1 to 10 wt %, the content of the acid generator is 0.01 to 2 wt %, the content of the cross-linking agent is 0.01 to 5 wt %, the content of the solvent is 80 to 95 wt %, and the content of the surfactant is 0 to 3 wt %.

3. The anti-reflective coating composition according to claim 1, wherein The aromatic thiodiepoxide is prepared according to the following method: S1, condensing the aromatic aldehyde compound represented by formula (3) with 2-mercaptoethanol to obtain an intermediate product; S2. subjecting the intermediate product to a substitution reaction with epichlorohydrin to obtain an aromatic thiodiepoxide; In formula (3), Ar is an aromatic group, and R1 is selected from H, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a nitro group, a nitroso group, or a halogen group; Optionally, in step S1, the condensation reaction is carried out in the presence of a first catalyst; Optionally, in step S1, the first catalyst is nickel chloride and / or zirconium chloride; Optionally, in step S1, the amount of the first catalyst added is 0.5 to 2.0% of the total mass of the aromatic aldehyde compound and 2-mercaptoethanol; Optionally, in step S1, the molar ratio of the aromatic aldehyde compound to 2-mercaptoethanol is 1:(2-2.5); Optionally, in step S1, the condensation reaction temperature is 20-35°C and the time is 1-2h; Optionally, in step S1, the structure of the intermediate product is as shown in formula (4): In formula (4), Ar is an aromatic group, and R1 is selected from H, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, nitro, nitroso or halogen; Optionally, in step S2, the substitution reaction is carried out in the presence of a second catalyst; Optionally, in step S2, the second catalyst is tetrabutylammonium chloride and / or tetrabutylammonium bromide; Optionally, in step S2, the amount of the second catalyst added is 0.1 to 3.0% of the total mass of the intermediate product and epichlorohydrin; Optionally, in step S2, the input mass ratio of the intermediate product to epichlorohydrin is 1:(2.0-3.0); Optionally, in step S2, the substitution reaction is carried out at a temperature of 25 to 45° C. and for a time of 4 to 12 hours.

4. The anti-reflective coating composition according to claim 1, wherein The hydroxyalkyl isocyanurate is selected from at least one of 1-allyl-3,5-bis(2-hydroxyethyl)isocyanurate, 1-(2-hydroxyethyl)-3,5-diethylisocyanurate, 1-(2-cyclohexylethyl)-3,5-bis(2-hydroxyethyl)isocyanurate and 1,3,5-tris(2-hydroxyethyl)isocyanurate.

5. The anti-reflective coating composition according to any one of claims 1 to 4, characterized in that The molar ratio of the structural unit derived from the aromatic thiodiepoxide represented by formula (1) to the structural unit derived from the hydroxyalkyl isocyanurate represented by formula (2) in the aromatic thioepoxy resin is 1:(1-3).

6. The anti-reflective coating composition according to any one of claims 1 to 4, characterized in that The aromatic thioepoxy resin has a weight average molecular weight of 2000 to 15000 Da and a polydispersity index (PDI) of 1.2 to 3.

2.

7. The antireflective coating composition according to any one of claims 1 to 4, characterized in that The aromatic thioepoxy resin is prepared by reacting aromatic thiodiepoxide with hydroxyalkyl isocyanurate; Optionally, the molar ratio of the aromatic thiodiepoxide to the hydroxyalkyl isocyanurate is 1:(1-3); Optionally, the temperature of the addition reaction is 80 to 130° C., and the time is 2 to 48 hours.

8. The anti-reflective coating composition according to any one of claims 1 to 4, characterized in that The acid generator is selected from at least one of a sulfonium salt compound, an iodine salt organic compound and an organic sulfonic acid compound; Optionally, the crosslinking agent is selected from at least one of tetramethoxymethyl glycoluril, hexamethoxymethyl melamine, tetramethoxymethyl benzoguanamine, 1,3,4,6-tetrakis(butoxymethyl) glycoluril, 1,3,4,6-tetrakis(hydroxymethyl) glycoluril, 1,3-bis(hydroxymethyl)urea, N-hydroxymethyl acrylamide, N-methoxymethyl methacrylamide and N-ethoxymethyl acrylamide; Optionally, the surfactant is selected from fluorinated surfactants and / or non-fluorinated surfactants; Optionally, the solvent is selected from at least one of methyl 2-hydroxyisobutyrate, cyclohexanone, cyclopentanone, butyrolactone, dimethylacetamide, dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, tetrahydrofurfuryl alcohol, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate and ethyl lactate.

9. The method for preparing the anti-reflective coating composition according to any one of claims 1 to 8, characterized in that: The method comprises uniformly mixing an aromatic thioepoxy resin, an acid generator, a crosslinking agent, a solvent and an optional surfactant.

10. Use of the anti-reflective coating composition according to any one of claims 1 to 8 in the field of photolithography.

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