Method for forming photoresist pattern

By using a bottom anti-reflective composition with a specific composition, the patterning problem caused by light reflection in the photolithography process was solved, achieving high-resolution and efficient photoresist patterning, simplifying the process flow and improving production efficiency.

CN120909073APending Publication Date: 2025-11-07SHANGHAI SINYANG SEMICONDUCTOR MATERIALS CO LTD
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Patent Information

Application Number
CN202410557297.5
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2024-05-07
Publication Date
2025-11-07

AI Technical Summary

Technical Problem

In photolithography, as the wavelength of the exposure light source becomes shorter, the optical interference effect caused by reflected light increases, resulting in poorer pattern contours and reduced dimensional uniformity. Existing alkali-soluble anti-reflective coatings have problems such as baking conditions, dissolution rate, and development residues, so there is an urgent need to develop superior alkali-soluble bottom anti-reflective coating materials.

Method used

A bottom anti-reflective composition containing specific weight proportions, including vinyl ether compounds, aromatic anthracene compounds, onium salt compounds, and solvents, is used to form a photoresist pattern through coating, calcination, exposure, and development, effectively reducing light reflection and avoiding etching processes.

Benefits of technology

It effectively reduces light reflection, eliminates standing wave effects, improves pattern resolution, reduces etching damage to the substrate, simplifies the operation process, and improves production efficiency.

✦ Generated by Eureka AI based on patent content.

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Patent Text Reader

Abstract

The invention discloses a method for forming a photoresist pattern. The method for forming the photoresist pattern comprises the following steps: S1, casting a bottom anti-reflection composition on a semiconductor substrate, and roasting to obtain a bottom anti-reflection coating; s2, coating a photoresist on the bottom anti-reflection coating layer; s3, soft roasting; s4, performing exposure; s5, roasting; and S6, developing. The coating prepared from the bottom anti-reflection composition can effectively reduce the light reflection effect, and the etching process of the anti-reflection coating is avoided.
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Description

TECHNICAL FIELD

[0001] The present application relates to the field of photoresist technology, in particular to a method for forming a photoresist pattern. BACKGROUND

[0002] In recent years, due to the continuous high integration of large scale integrated circuits (LSI), in order to miniaturize the photolithography process, especially to carry out the ultra-fine pattern process below 30 nm node, the resolution of the photoresist used in the photolithography process has become a decisive important factor. Therefore, in the commonly used g-line or i-line region, the wavelength of the exposure light is also further shortened, and therefore the research on photolithography using deep ultraviolet, KrF excimer laser, ArF excimer laser has attracted much attention.

[0003] However, when the wavelength of the exposure light source is shortened, the light interference effect caused by the reflected light reflected on the layer to be etched of the semiconductor substrate is increased, and due to undercutting, notching, etc., the problems of poor pattern profile or reduced size uniformity occur. In order to prevent the above problems, a bottom anti-reflective coating (BARC) for absorbing exposure light (reflected light) is usually formed between the layer to be etched and the photoresist film.

[0004] There are two kinds of etching processes commonly used for anti-reflective coatings at present: etching type and alkali-soluble type. Both processes are to coat an anti-reflective coating on the substrate, then spin a layer of photoresist on it, and then perform processes such as pre-baking, exposure, post-baking, etc. for development. For photoresist development patterning, there is no difference between the two processes, and the biggest difference between them is the removal process of the coating. The etching type anti-reflective coating is mainly removed by plasma, while the alkali-soluble anti-reflective coating is removed by a mechanism similar to photoresist development and reaction with the developer. Both processes have their advantages and disadvantages, the etching type process has been widely used in industrial production and has certain controllability and maturity. While the alkali-soluble anti-reflective coating can avoid etching process, reduce the damage of plasma to the substrate, reduce the operation process and improve the production efficiency, but it needs to consider the baking conditions, dissolution rate, post-development residue (PDR) and other problems, therefore, it is urgent to develop excellent alkali-soluble bottom anti-reflective coating (BARC) materials in the industry. SUMMARY

[0005] To overcome the problem of the prior art that there are few methods for forming a photoresist pattern, a method for forming a photoresist pattern is provided. The coating prepared from the bottom anti-reflective composition of the present application can effectively reduce the reflection of light and avoid the etching process of the anti-reflective coating.

[0006] The present application provides a method for forming a photoresist pattern, which comprises the following steps:

[0007] S1: casting a bottom anti-reflective composition on a semiconductor substrate, baking to obtain a bottom anti-reflective coating;

[0008] S2: applying a photoresist on the bottom anti-reflective coating;

[0009] S3: soft baking;

[0010] S4: exposure;

[0011] S5: baking;

[0012] S6: development;

[0013] The bottom anti-reflective composition comprises the following components by weight: 50-200 parts of a compound represented by formula I, 1-100 parts of a crosslinking agent, 0.01-50 parts of a light absorber, 0.01-50 parts of a photoacid generator, and a solvent;

[0014]

[0015] In the bottom anti-reflective composition, the crosslinking agent is a vinyl ether compound; preferably CH2=CH-O-R-CH=CH2, each R is independently selected from C 1-10 alkylene or C 1-10 alkyleneoxy; for example, a compound represented by formula II

[0016] In the bottom anti-reflective composition, the light absorber is an anthracene compound containing an aromatic structure, for example

[0017] In the bottom anti-reflective composition, the photoacid generator is one or more of onium salt compounds, sulfone imide derivatives, and disulfonyl diazomethane compounds.

[0018] In the bottom anti-reflective composition, the solvent is one or more of ether solvents, ester solvents, alcohol solvents, aromatic hydrocarbon solvents, ketone solvents, and amide solvents.

[0019] The ether solvent in the bottom anti-reflective composition is preferably one or more of propylene glycol monobutyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, and propylene glycol monomethyl ether; and is further preferably propylene glycol monobutyl ether.

[0020] The ester solvent in the bottom anti-reflective composition is preferably one or more of propylene glycol monobutyl ether acetate, methyl cellosolve acetate, ethyl cellosolve acetate, propylene glycol monomethyl ether acetate, propylene glycol propyl ether acetate, 2-hydroxypropionic acid ethyl ester, 2-hydroxy-2-methyl-propionic acid ethyl ester, ethoxyacetic acid ethyl ester, glycolic acid ethyl ester, 2-hydroxy-3-methylbutyric acid methyl ester, 3-methoxypropionic acid methyl ester, 3-methoxypropionic acid ethyl ester, 3-ethoxypropionic acid ethyl ester, 3-ethoxypropionic acid methyl ester, pyruvic acid methyl ester, pyruvic acid ethyl ester, acetic acid ethyl ester, acetic acid butyl ester, lactic acid ethyl ester, and lactic acid butyl ester.

[0021] The alcohol solvent in the bottom anti-reflective composition is preferably propylene glycol.

[0022] The aromatic hydrocarbon solvent in the bottom anti-reflective composition is preferably toluene and / or xylene.

[0023] The ketone solvent in the bottom anti-reflective composition is preferably one or more of methyl ethyl ketone, cyclopentanone, and cyclohexanone.

[0024] The amide solvent in the bottom anti-reflective composition is preferably one or more of N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0025] The compound of Formula I in the bottom anti-reflective composition is preferably in an amount of 50 to 150 parts by weight, and is further preferably in an amount of 50 to 100 parts by weight, for example, 100 parts by weight.

[0026] The crosslinking agent in the bottom anti-reflective composition is preferably in an amount of 1 to 20 parts by weight, for example, 1, 5, 10, or 20 parts by weight.

[0027] The photoabsorber in the bottom anti-reflective composition is preferably in an amount of 1 to 20 parts by weight, for example, 1, 5, 10, or 20 parts by weight.

[0028] The photoacid generator in the bottom anti-reflective composition is preferably in an amount of 1 to 20 parts by weight, for example, 1, 5, 10, or 20 parts by weight.

[0029] The solvent in the bottom anti-reflective composition is preferably in an amount of 1000 to 2500 parts by weight, preferably in an amount of 1200 to 2000 parts by weight, and more preferably in an amount of 1500 to 1800 parts by weight, for example, 1000 parts by weight.

[0030] The onium salt compound in the bottom anti-reflective composition is preferably an iodonium salt compound, a sulfonium salt compound, or a cross-linkable onium salt compound.

[0031] The iodonium salt compound is preferably one or more of diphenyl iodonium hexafluorophosphate, diphenyl iodonium triflate, diphenyl iodonium nonafluoro-n-butane sulfonate, diphenyl iodonium perfluoro-n-octane sulfonate, diphenyl iodonium camphor sulfonate, bis(4-tert-butylphenyl) iodonium camphor sulfonate, and bis(4-tert-butylphenyl) iodonium triflate.

[0032] The sulfonium salt compound is preferably one or more of triphenyl sulfonium hexafluoroantimonate, triphenyl sulfonium nonafluoro-n-butane sulfonate, triphenyl sulfonium camphor sulfonate, and triphenyl sulfonium triflate, and more preferably triphenyl sulfonium hexafluoroantimonate and / or triphenyl sulfonium triflate.

[0033] The cross-linkable onium salt compound is preferably one or more of bis(4-hydroxyphenyl)(phenyl) sulfonium triflate, bis(4-hydroxyphenyl)(phenyl) sulfonium 1,1,2,2,3,3,4,4,4-nonafluoro-butane-1-sulfonate, phenyl bis(4-(2-(vinyloxy)ethoxy)-phenyl) sulfonium 1,1,2,2,3,3,4,4-octafluoro-butane-1,4-disulfonate, and tri(4-(2-(vinyloxy)ethoxy)-phenyl) sulfonium 1,1,2,2,3,3,4,4-octafluoro-butane-1,4-disulfonate.

[0034] The sulfone imide derivative in the bottom anti-reflective composition is preferably one or more of N-(trifluoromethanesulfonyloxy)succinimide, N-(fluoro-n-butanesulfonyloxy)succinimide, N-(camphor sulfonyloxy)succinimide, and N-(trifluoromethylsulfonyloxy)naphthalene dicarboxylic imide.

[0035] The disulfono diazomethane compound in the bottom anti-reflective composition is preferably one or more of bis(trifluoromethylsulfonyl) diazomethane, bis(cyclohexylsulfonyl) diazomethane, bis(benzenesulfonyl) diazomethane, bis(p-toluenesulfonyl) diazomethane, bis(2,4-dimethylbenzenesulfonyl) diazomethane, and methylsulfonyl-p-toluenesulfonyl diazomethane.

[0036] The bottom anti-reflective composition can further contain other additional components. The additional components include a surfactant or a smoothing agent.

[0037] The amount of the additional components in the bottom anti-reflective composition is not particularly limited and can be appropriately determined according to the target coating.

[0038] The bottom anti-reflective composition is composed of the following components in parts by weight: 50-200 parts of the compound shown as formula I, 1-100 parts of a crosslinking agent, 0.01-50 parts of a light absorbing agent, 0.01-50 parts of a photoacid generator and a solvent;

[0039] The compound shown as formula I, the crosslinking agent, the light absorbing agent, the photoacid generator and the solvent are the same as described above.

[0040] The bottom anti-reflective composition is any one of the following compositions:

[0041] Composition C1-1: 100 parts of the compound shown as formula I, 1 part of the compound shown as formula II, 1 part of the compound shown as formula III, 1 part of triphenylsulfonium hexafluoroantimonate and 1000 parts of propylene glycol monobutyl ether; 1 part of triphenylsulfonium trifluoromethanesulfonate and 1000 parts of propylene glycol monobutyl ether;

[0042] Composition C1-2: 100 parts of the compound shown as formula I, 5 parts of the compound shown as formula II, 5 parts of the compound shown as formula III, 5 parts of triphenylsulfonium hexafluoroantimonate and 1000 parts of propylene glycol monobutyl ether; 5 parts of triphenylsulfonium trifluoromethanesulfonate and 1000 parts of propylene glycol monobutyl ether;

[0043] Composition C1-3: 100 parts of the compound shown as formula I, 10 parts of the compound shown as formula II, 10 parts of the compound shown as formula III, 10 parts of triphenylsulfonium hexafluoroantimonate and 1000 parts of propylene glycol monobutyl ether; 10 parts of triphenylsulfonium trifluoromethanesulfonate and 1000 parts of propylene glycol monobutyl ether;

[0044] Composition C1-4: 100 parts of the compound shown as formula I, 20 parts of the compound shown as formula II, 20 parts of the compound shown as formula III, 20 parts of triphenylsulfonium hexafluoroantimonate and 1000 parts of propylene glycol monobutyl ether; 20 parts of triphenylsulfonium trifluoromethanesulfonate and 1000 parts of propylene glycol monobutyl ether;

[0045] Composition C2-1: 100 parts of the compound shown as formula I, 1 part of the compound shown as formula II, 1 part of the compound shown as formula III, 1 part of triphenylsulfonium trifluoromethanesulfonate and 1000 parts of propylene glycol monobutyl ether; 1 part of triphenylsulfonium trifluoromethanesulfonate and 1000 parts of propylene glycol monobutyl ether;

[0046] Composition C2-2: 100 parts of the compound shown as formula I, 5 parts of the compound shown as formula II, 5 parts of the compound shown as formula III, 5 parts of triphenylsulfonium trifluoromethanesulfonate and 1000 parts of propylene glycol monobutyl ether; 5 parts of triphenylsulfonium trifluoromethanesulfonate and 1000 parts of propylene glycol monobutyl ether;

[0047] Composition C2-3: 100 parts of the compound shown as formula I, 10 parts of the compound shown as formula II, 10 parts of the compound shown as formula III, 10 parts of triphenylsulfonium trifluoromethanesulfonate and 1000 parts of propylene glycol monobutyl ether; 10 parts of triphenylsulfonium trifluoromethanesulfonate and 1000 parts of propylene glycol monobutyl ether;

[0048] Composition C2-4: 100 parts of the compound of Formula I, 20 parts of the compound of Formula II, 20 parts of 20 parts of triphenylsulfonium triflate and 1000 parts of propylene glycol monobutyl ether;

[0049] Composition C3-1 : 100 parts of the compound of Formula I, 1 part of the compound of Formula II, 1 part of 1 part of triphenylsulfonium hexafluoroantimonate and 1000 parts of propylene glycol monobutyl ether;

[0050] Composition C3-2: 100 parts of the compound of Formula I, 5 parts of the compound of Formula II, 5 parts of 5 parts of triphenylsulfonium hexafluoroantimonate and 1000 parts of propylene glycol monobutyl ether;

[0051] Composition C3-3: 100 parts of the compound of Formula I, 10 parts of the compound of Formula II, 10 parts of 10 parts of triphenylsulfonium hexafluoroantimonate and 1000 parts of propylene glycol monobutyl ether;

[0052] Composition C3-4: 100 parts of the compound of Formula I, 20 parts of the compound of Formula II, 20 parts of 20 parts of triphenylsulfonium hexafluoroantimonate and 1000 parts of propylene glycol monobutyl ether;

[0053] Composition C4-1 : 100 parts of the compound of Formula I, 1 part of the compound of Formula II, 1 part of 1 part of triphenylsulfonium triflate and 1000 parts of propylene glycol monobutyl ether;

[0054] Composition C4-2: 100 parts of the compound of Formula I, 5 parts of the compound of Formula II, 5 parts of 5 parts of triphenylsulfonium triflate and 1000 parts of propylene glycol monobutyl ether;

[0055] Composition C4-3: 100 parts of the compound of Formula I, 10 parts of the compound of Formula II, 10 parts of 10 parts of triphenylsulfonium triflate and 1000 parts of propylene glycol monobutyl ether;

[0056] Composition C4-4: 100 parts of the compound of Formula I, 20 parts of the compound of Formula II, 20 parts of 20 parts of triphenylsulfonium triflate and 1000 parts of propylene glycol monobutyl ether.

[0057] The bottom anti-reflective composition is prepared by a preparation method comprising the following steps: mixing the compound (including the kind and the weight fraction) as shown in Formula I, the crosslinking agent (including the kind and the weight fraction), the light absorbing agent (including the kind and the weight fraction), the photo-acid generator (including the kind and the weight fraction) and the solvent (including the kind and the weight fraction) as described above to obtain the bottom anti-reflective composition.

[0058] The mixing temperature is preferably 15-35°C, for example 25°C.

[0059] The mixing mode is preferably stirring, and the stirring time is further preferably 30 minutes.

[0060] After mixing, a filtration step is also preferably included, and the filtration mode is preferably filtration using a filter, and the pore size of the filter is preferably 0.05-0.2 μm, more preferably 0.05 μm.

[0061] In the method for forming a photoresist pattern, the photoresist can be conventional in the art, and is preferably a positive photoresist, a negative photoresist or a negative tone development (NTD) photoresist, and is more preferably a 193 nm positive photoresist (TOK company, tai-6990PH).

[0062] In the method for forming a photoresist pattern, the soft baking temperature is 100-140°C, and is preferably 120°C.

[0063] In the method for forming a photoresist pattern, the soft baking time is 0.5-2 minutes, and is preferably 1 minute.

[0064] In the method for forming a photoresist pattern, the exposure light can be conventional in the art, and is preferably light having a wavelength of 13.5-248 nm, and is more preferably an ArF excimer laser (wavelength: 193 nm).

[0065] In the method for forming a photoresist pattern, the baking temperature is 80-150°C, and is preferably 100-140°C, and is more preferably 130°C.

[0066] In the method for forming a photoresist pattern, the baking time is 0.3-5 minutes, and is preferably 0.5-2 minutes, and is further preferably 1 minute.

[0067] In the method for forming a photoresist pattern, the development is performed using a developing solution which can easily dissolve and remove the bottom anti-reflective coating.

[0068] In the method for forming a photoresist pattern, the developing solution is preferably an alkali developing solution, further preferably an aqueous solution of an alkali metal hydroxide, an aqueous solution of a tertiary amine hydroxide or an aqueous solution of an amine.

[0069] In the method for forming a photoresist pattern, the aqueous solution of an alkali metal hydroxide is preferably an aqueous solution of potassium hydroxide or an aqueous solution of sodium hydroxide.

[0070] In the method for forming a photoresist pattern, the aqueous solution of a tertiary amine hydroxide is preferably an aqueous solution of tetramethylammonium hydroxide (TMAH), an aqueous solution of tetraethylammonium hydroxide or an aqueous solution of choline.

[0071] In the method for forming a photoresist pattern, the aqueous solution of an amine is preferably an aqueous solution of ethanolamine, an aqueous solution of propylamine or an aqueous solution of ethylenediamine.

[0072] In the method for forming a photoresist pattern, the developing solution is more preferably an aqueous solution of 2.38 wt% tetramethylammonium hydroxide.

[0073] In the method for forming a photoresist pattern, the developing solution can further contain a surfactant.

[0074] In the method for forming a photoresist pattern, the developing temperature is preferably 5-50°C, more preferably 25-40°C, for example 30°C.

[0075] In the method for forming a photoresist pattern, the developing time is preferably 10-300 seconds, more preferably 30-60 seconds, for example 40 seconds.

[0076] The present application also provides a method for preparing a bottom anti-reflective composition, comprising the step of mixing the components of the composition as described above.

[0077] The method for preparing a bottom anti-reflective composition is as described above.

[0078] The present application also provides a method for preparing a bottom anti-reflective coating, comprising the steps of casting the composition as described above on a semiconductor substrate, and baking to obtain a bottom anti-reflective coating.

[0079] In the method for preparing a bottom anti-reflective coating, the casting tool is a spin coater or a coater, preferably a spin coater.

[0080] In the method for preparing a bottom anti-reflective coating, the semiconductor substrate is one of a silicon or silicon dioxide coated substrate, a silicon nitride substrate, a silicon wafer substrate, a glass substrate or an ITO substrate, preferably a silicon wafer substrate.

[0081] In the method for preparing the bottom anti-reflective coating, the calcination temperature is 80-250℃, preferably 100-250℃, and more preferably 190℃.

[0082] In the method for preparing the bottom anti-reflective coating, the calcination time is 0.3-5 minutes, preferably 0.5-2 minutes, and more preferably 1 minute.

[0083] Based on common knowledge in the field, the above-mentioned preferred conditions can be combined arbitrarily to obtain various preferred embodiments of the present invention.

[0084] In this invention, the room temperature is 15-35℃, preferably 25℃.

[0085] The reagents and raw materials used in this invention are all commercially available.

[0086] The positive and progressive effects of this invention are: it can effectively reduce light reflection, eliminate standing wave effect, reduce pattern LER and LWE, improve pattern resolution, avoid etching process, reduce plasma damage to the substrate, reduce operation process, and improve production efficiency. Detailed Implementation

[0087] The present invention is further illustrated below by way of embodiments, but the invention is not limited to the scope of the embodiments described herein. Experimental methods in the following embodiments that do not specify specific conditions were performed according to conventional methods and conditions, or as selected according to the product instructions.

[0088] In the description of the embodiments, "parts" and "%" refer to "parts by weight" and "wt%" respectively, unless otherwise stated.

[0089] Example 1: Preparation method of bottom anti-reflective coating

[0090] The compound shown in Formula I, the crosslinking agent shown in Formula II, the light absorber, the photoacid generator, and the solvent were mixed, with the types and amounts shown in Tables 1 and 2. The mixture was stirred at room temperature for 30 minutes, and then filtered through a filter with a pore size of 0.05 μm to prepare a bottom antireflective composition in solution form.

[0091] The prepared bottom antireflective composition was spin-coated onto a silicon wafer substrate and crosslinked by heating at 190°C for 1 minute on a vacuum hot plate to obtain the bottom antireflective coatings of Examples 1-16 below.

[0092]

[0093] Table 1 Categories

[0094]

[0095] Table 2 Amount

[0096]

[0097]

[0098] Example 2 Application and Effect

[0099] 1. Optical property measurement

[0100] Refractive index (n value) and extinction coefficient (k value) at 193 nm of the bottom anti-reflective coating obtained by ellipsometry measurement.

[0101] 2. Development property measurement

[0102] Method for forming a photoresist pattern and development property measurement of the bottom anti-reflective coating when the exposure light wavelength is 193 nm

[0103] A commercially available 193 nm positive photoresist (TOK Corporation, tai-6990PH) was spin-coated on the obtained bottom anti-reflective coating. The formed resist layer was soft-baked on a vacuum hot plate at 120°C for 1 minute, and then imagewise exposed to 193 nm radiation by a photomask. After post-exposure baking at 130°C for 1 minute, the resist layer was developed at 30°C using a 2.38 wt% aqueous TMAH solution for 40 seconds. As a result of this development, the photoresist layer and the underlying bottom anti-reflective coating were removed in the areas defined by the photomask, and the solvent resistance of the anti-reflective coating was observed in the areas exposed to radiation. The pattern cross-sectional shape was observed.

[0104] The results of the performance tests of the bottom anti-reflective coatings 1-16 are shown in Table 3.

[0105] Table 3

[0106]

[0107]

[0108] Note: Regarding the cross-sectional shape of the pattern: A indicates that both the photoresist and the bottom anti-reflective coating exhibit rectangular sides perpendicular to the substrate surface; B indicates that both the photoresist and the bottom anti-reflective coating exhibit sides that are not perpendicular but slightly inclined to the substrate surface, but there is no problem in practice; C indicates that both the photoresist and the bottom anti-reflective coating exhibit sides in a dovetail shape with respect to the substrate surface.

Claims

1. A method of forming a photoresist pattern, characterized by, It comprises the following steps: S1: casting a bottom anti-reflective composition on a semiconductor substrate, baking to obtain a bottom anti-reflective coating; S2: coating a photoresist on the bottom anti-reflective coating; S3: soft baking; S4: exposure; S5: baking; S6: development; The bottom anti-reflective composition comprises the following components by weight: 50-200 parts of the compound shown as formula I, 1-100 parts of a crosslinking agent, 0.01-50 parts of a light absorber, 0.01-50 parts of a photoacid generator, and a solvent; 2. The method of forming a photoresist pattern of claim 1, wherein, The bottom anti-reflective composition meets one or more of the following conditions: (1) the crosslinking agent is a vinyl ether compound; preferably CH2=CH-O-R-CH=CH2, each R being independently selected from C 1-10 alkylene or C 1-10 alkyleneoxy; for example a compound of formula II (2) In the bottom anti-reflective composition, the light absorbing agent is an anthracene compound having an aromatic structure, for example (3) The photoacid generator is one or more of onium salt compounds, sulfone imide derivatives, and disulfone diazomethane compounds; (4) The solvent is one or more of ether solvents, ester solvents, alcohol solvents, aromatic hydrocarbon solvents, ketone solvents, and amide solvents; (5) The compound shown as formula I is 50-150 parts by weight, preferably 50-100 parts, for example 100 parts; (6) The crosslinking agent is 1-20 parts by weight, for example 1, 5, 10, or 20 parts; (7) The light absorber is 1-20 parts by weight, for example 1, 5, 10, or 20 parts; (8) The photoacid generator is 1-20 parts by weight, for example 1, 5, 10, or 20 parts; (9) The solvent is 1000-2500 parts by weight, preferably 1200-2000 parts, more preferably 1500-1800 parts, for example 1000 parts.

3. The method of forming a photoresist pattern according to claim 2, wherein, The bottom anti-reflective composition meets one or more of the following conditions: (1) The ether solvent is one or more of propylene glycol monobutyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, and propylene glycol monomethyl ether; further preferably propylene glycol monobutyl ether; (2) The ester solvent is one or more of propylene glycol monobutyl ether acetate, methyl cellosolve acetate, ethyl cellosolve acetate, propylene glycol monomethyl ether acetate, propylene glycol propyl ether acetate, 2-hydroxypropionic acid ethyl ester, 2-hydroxy-2-methyl-propionic acid ethyl ester, ethoxyacetic acid ethyl ester, hydroxyacetic acid ethyl ester, 2-hydroxy-3-methylbutyric acid methyl ester, 3-methoxypropionic acid methyl ester, 3-methoxypropionic acid ethyl ester, 3-ethoxypropionic acid ethyl ester, 3-ethoxypropionic acid methyl ester, pyruvic acid methyl ester, pyruvic acid ethyl ester, acetic acid ethyl ester, acetic acid butyl ester, lactic acid ethyl ester, and lactic acid butyl ester; (3) The alcohol solvent is propylene glycol; (4) The aromatic hydrocarbon solvent is toluene and / or xylene; (5) The ketone solvent is one or more of methyl ethyl ketone, cyclopentanone, and cyclohexanone; (6) The amide solvent is one or more of N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

4. The method of forming a photoresist pattern of claim 2, wherein, The bottom anti-reflective composition meets one or more of the following conditions: (1) The onium salt compound is an iodonium salt compound, a sulfonium salt compound, or a crosslinkable onium salt compound; The iodonium salt compound is preferably one or more of diphenyl iodonium hexafluorophosphate, diphenyl iodonium trifluoromethanesulfonate, diphenyl iodonium nonafluoro-n-butanesulfonate, diphenyl iodonium perfluoro-n-octanesulfonate, diphenyl iodonium camphorsulfonate, bis(4-tert-butylphenyl) iodonium camphorsulfonate, and bis(4-tert-butylphenyl) iodonium trifluoromethanesulfonate; The sulfonium salt compound is preferably one or more of triphenyl sulfonium hexafluoroantimonate, triphenyl sulfonium nonafluoro-n-butanesulfonate, triphenyl sulfonium camphorsulfonate, and triphenyl sulfonium trifluoromethanesulfonate, and more preferably triphenyl sulfonium hexafluoroantimonate and / or triphenyl sulfonium trifluoromethanesulfonate; The cross-linkable onium salt compound is preferably one or more of bis(4-hydroxyphenyl)(phenyl) sulfonium trifluoromethanesulfonate, bis(4-hydroxyphenyl)(phenyl) sulfonium 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate, phenyl bis(4-(2-(vinlyloxy)ethoxy)-phenyl) sulfonium 1,1,2,2,3,3,4,4-octafluoro-butane-1,4-disulfonate, and tri(4-(2-(vinlyloxy)ethoxy)-phenyl) sulfonium 1,1,2,2,3,3,4,4-octafluoro-butane-1,4-disulfonate; (2) The sulfone imide derivative is one or more of N-(trifluoromethanesulfonyloxy)succinimide, N-(fluoro-n-butanesulfonyloxy)succinimide, N-(camphorsulfonyloxy)succinimide, and N-(trifluoromethylsulfonyloxy)naphthalene dicarboximide; (3) The disulfono diazomethane compound is one or more of bis(trifluoromethylsulfonyl) diazomethane, bis(cyclohexylsulfonyl) diazomethane, bis(benzenesulfonyl) diazomethane, bis(p-toluenesulfonyl) diazomethane, bis(2,4-dimethylbenzenesulfonyl) diazomethane, and methylsulfonyl-p-toluenesulfonyl diazomethane.

5. The method of forming a photoresist pattern according to claim 1, wherein, The bottom anti-reflective composition is composed of the following components by weight parts: 50-200 parts of the compound represented by Formula I, 1-100 parts of the cross-linking agent, 0.01-50 parts of the light absorber, 0.01-50 parts of the photo-acid generator, and a solvent.

6. The method of forming a photoresist pattern of claim 1, wherein, The bottom anti-reflective composition is any one of the following compositions: (1) Composition C1-1: 100 parts of the compound represented by Formula I, 1 part of the compound represented by Formula II, 1 part of 1 part of triphenylsulfonium hexafluoroantimonate and 1000 parts of propylene glycol monobutyl ether; (2) Composition C1-2: 100 parts of the compound shown in Formula I, 5 parts of the compound shown in Formula II, and 5 parts of... 5 parts triphenylsulfonium hexafluoroantimonate and 1000 parts propylene glycol monobutyl ether; (3) Composition C1-3: 100 parts of the compound shown in Formula I, 10 parts of the compound shown in Formula II, and 10 parts of... 10 parts triphenylsulfonium hexafluoroantimonate and 1000 parts propylene glycol monobutyl ether; (4) Composition C1-4: 100 parts of the compound shown in Formula I, 20 parts of the compound shown in Formula II, and 20 parts of... 20 parts triphenylsulfonium hexafluoroantimonate and 1000 parts propylene glycol monobutyl ether; (5) Composition C2-1: 100 parts of the compound represented by Formula I, 1 part of the compound represented by Formula II, 1 part of 1 part of triphenylsulfonium trifluoromethanesulfonate and 1000 parts of propylene glycol monobutyl ether; (6) Composition C2-2: 100 parts of the compound shown in Formula I, 5 parts of the compound shown in Formula II, and 5 parts of... 5 parts triphenylsulfonate trifluoromethane sulfonate and 1000 parts propylene glycol monobutyl ether; (7) Composition C2-3: 100 parts of the compound shown in Formula I, 10 parts of the compound shown in Formula II, and 10 parts of... 10 parts triphenylsulfonate trifluoromethane sulfonate and 1000 parts propylene glycol monobutyl ether; (8) Composition C2-4: 100 parts of the compound shown in Formula I, 20 parts of the compound shown in Formula II, and 20 parts of... 20 parts of triphenylsulfonium trifluoromethane sulfonate and 1000 parts of propylene glycol monobutyl ether; (9) Composition C3-1: 100 parts of the compound represented by Formula I, 1 part of the compound represented by Formula II, 1 part of 1 part of triphenylsulfonium hexafluoroantimonate and 1000 parts of propylene glycol monobutyl ether; (10) Composition C3-2: 100 parts of the compound shown in Formula I, 5 parts of the compound shown in Formula II, and 5 parts of... 5 parts triphenylsulfonium hexafluoroantimonate and 1000 parts propylene glycol monobutyl ether; (11) Composition C3-3: 100 parts of the compound shown in Formula I, 10 parts of the compound shown in Formula II, and 10 parts of... 10 parts triphenylsulfonium hexafluoroantimonate and 1000 parts propylene glycol monobutyl ether; (12) Composition C3-4: 100 parts of the compound represented by Formula I, 20 parts of the compound represented by Formula II, 20 parts of 20 parts of triphenylsulfonium hexafluoroantimonate and 1000 parts of propylene glycol monobutyl ether; (13) Composition C4-1 : 100 parts of the compound represented by Formula I, 1 part of the compound represented by Formula II, 1 part of 1 part of triphenylsulfonium trifluoromethanesulfonate and 1000 parts of propylene glycol monobutyl ether; (14) Composition C4-2: 100 parts of the compound shown in Formula I, 5 parts of the compound shown in Formula II, and 5 parts of... 5 parts triphenylsulfonate trifluoromethane sulfonate and 1000 parts propylene glycol monobutyl ether; (15) Composition C4-3: 100 parts of the compound shown in Formula I, 10 parts of the compound shown in Formula II, and 10 parts of... 10 parts triphenylsulfonate trifluoromethane sulfonate and 1000 parts propylene glycol monobutyl ether; (16) Composition C4-4: 100 parts of the compound represented by Formula I, 20 parts of the compound represented by Formula II, 20 parts of 20 parts of triphenylsulfonium trifluoromethanesulfonate, and 1000 parts of propylene glycol monobutyl ether.

7. The method of forming a photoresist pattern according to any one of claims 1 to 6, wherein The bottom anti-reflective composition is prepared by the following preparation method; the preparation method comprises the following steps: mixing the compound represented by Formula I according to any one of claims 1-6, the cross-linking agent according to any one of claims 1-6, the light absorber according to any one of claims 1-6, the photo-acid generator according to any one of claims 1-6, and the solvent according to any one of claims 1-6 to obtain the bottom anti-reflective composition according to any one of claims 1-6; The mixing temperature is preferably 15-35°C, for example 25°C; The mixing mode is preferably stirring, and the stirring time is further preferably 30 minutes; The mixing is preferably followed by a filtration step, preferably using a filter having a pore size of 0.05 to 0.2 μm, more preferably 0.05 μm.

8. The method of forming a photoresist pattern of claim 1, wherein, one or more of the following conditions are satisfied: (1) the photoresist is a positive photoresist, a negative photoresist or a negative tone development photoresist, preferably a 193 nm positive photoresist; (2) the soft bake temperature is 100 to 140 °C, preferably 120 °C; (3) the soft bake time is 0.5 to 2 minutes, preferably 1 minute; (4) the exposure light is light having a wavelength of 13.5 to 248 nm, more preferably an ArF excimer laser having a wavelength of 193 nm; (5) the bake temperature is 80 to 150 °C, preferably 100 to 140 °C, more preferably 130 °C; (6) the bake time is 0.3 to 5 minutes, preferably 0.5 to 2 minutes, more preferably 1 minute; (7) the developing solution is an alkaline developing solution, preferably an aqueous solution of an alkali metal hydroxide, an aqueous solution of a tertiary ammonium hydroxide or an aqueous solution of an amine; (8) the developing temperature is 5 to 50 °C, preferably 25 to 40 °C, for example 30 °C; (9) the developing time is 10 to 300 seconds, preferably 30 to 60 seconds, for example 40 seconds.

9. The method of forming a photoresist pattern of claim 8, wherein, one or more of the following conditions are satisfied: (1) the aqueous solution of an alkali metal hydroxide is an aqueous solution of potassium hydroxide or an aqueous solution of sodium hydroxide; (2) the aqueous solution of a tertiary ammonium hydroxide is an aqueous solution of tetramethylammonium hydroxide, an aqueous solution of tetraethylammonium hydroxide or an aqueous solution of choline; preferably an aqueous solution of 2.38 wt% tetramethylammonium hydroxide; (3) the aqueous solution of an amine is an aqueous solution of ethanolamine, an aqueous solution of propylamine or an aqueous solution of ethylenediamine.

10. The method of forming a photoresist pattern of claim 1 wherein, one or more of the following conditions are satisfied: (1) the casting tool is a spin coater or a coater, preferably a spin coater; (2) the semiconductor substrate is one of a silicon or silicon dioxide coated substrate, a silicon nitride substrate, a silicon wafer substrate, a glass substrate or an ITO substrate, preferably a silicon wafer substrate; (3) the bake temperature is 80 to 250 °C, preferably 100 to 250 °C, more preferably 190 °C; (4) the bake time is 0.3 to 5 minutes, preferably 0.5 to 2 minutes, more preferably 1 minute.

Citation Information

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