CN114167684A - Photoresist composition, preparation method and application thereof, and method for forming photoresist pattern - Google Patents

Photoresist composition, preparation method and application thereof, and method for forming photoresist pattern Download PDF

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Publication number
CN114167684A
CN114167684A CN202111483647.0A CN202111483647A CN114167684A CN 114167684 A CN114167684 A CN 114167684A CN 202111483647 A CN202111483647 A CN 202111483647A CN 114167684 A CN114167684 A CN 114167684A
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acid
photoresist
poly
photoresist composition
hydroxystyrene
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周元基
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Suntific Materials (weifang) Ltd
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Suntific Materials (weifang) Ltd
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/16—Coating processes; Apparatus therefor
    • G03F7/168—Finishing the coated layer, e.g. drying, baking, soaking
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • G03F7/30—Imagewise removal using liquid means
    • G03F7/32—Liquid compositions therefor, e.g. developers
    • G03F7/322—Aqueous alkaline compositions
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • G03F7/38—Treatment before imagewise removal, e.g. prebaking

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  • General Physics & Mathematics (AREA)
  • Materials For Photolithography (AREA)

Abstract

The invention provides a photoresist composition, a preparation method and application thereof, and a method for forming a photoresist pattern, and particularly relates to the technical field of photoresist. The photoresist composition comprises a poly-p-hydroxystyrene homopolymer and a photoinduced deactivator, and the mass ratio of the poly-p-hydroxystyrene homopolymer to the photoinduced deactivator is 100-600: 2-50. The weight average molecular weight of the poly (p-hydroxystyrene) homopolymer is 1000-20000. The photoresist composition has strong photosensitivity, and after exposure by adopting a light source of 248nm deep ultraviolet lithography, the exposure dose can be reduced to 10mJ/cm under the film thickness of 500nm2The following. The poly-p-hydroxystyrene homopolymer has no protective group and can participate in crosslinking, so the poly-p-hydroxystyrene homopolymer has higher carbon atom content and obviously improves the dry etching resistanceThe etching ratio is improved, the production efficiency of customers is greatly improved, and the production cost is reduced.

Description

Photoresist composition, preparation method and application thereof, and method for forming photoresist pattern
Technical Field
The invention relates to the technical field of photoresist, in particular to a photoresist composition, a preparation method and application thereof, and a method for forming a photoresist pattern.
Background
Deep ultraviolet positive photoresists for exposure to KrF excimer lasers (248nm) have wide and important applications in the market. The photoresist is mainly used for manufacturing chips with critical dimensions of 0.25-0.15 micrometers, and belongs to a neck clamp project.
The existing KrF photoresist system is mainly based on poly-p-hydroxystyrene and derivatives thereof, and the reaction mechanism of the KrF photoresist system is deprotection.Because the resin contains a large number of protecting groups and methacrylate monomers, the existence of the protecting groups reduces the content of carbon atoms in the adhesive film, and the content of the carbon atoms directly influences the dry etching resistance of the adhesive film, so that the dry etching resistance of the existing KrF positive photoresist cannot be continuously improved, and the technical effect is poor. Meanwhile, the protective group in the resin needs to be removed in the reaction, but the deprotection reaction needs more catalysts, so the exposure dose is usually 20-30 mJ/cm2The temperature cannot be continuously reduced, and the production efficiency of a chip factory is reduced.
In view of the above, the present invention is particularly proposed.
Disclosure of Invention
One of the objectives of the present invention is to provide a photoresist composition, which solves the technical problems of high exposure dose and poor dry etching resistance of the photoresist film in the prior art.
The second purpose of the present invention is to provide a method for preparing a photoresist composition, which has simple process, large handling capacity, suitability for mass production and low cost.
The invention also aims to provide the application of the photoresist composition in manufacturing integrated circuits, which improves the production efficiency of the integrated circuits and reduces the production cost.
The fourth objective of the present invention is to provide a method for forming a photoresist pattern, which ensures that the formed pattern meets the actual process requirements and realizes a better photoresist pattern.
In order to solve the technical problems, the invention adopts the following technical scheme:
in a first aspect of the invention, a photoresist composition is provided comprising a poly (p-hydroxystyrene) homopolymer and a photo-deactivator.
Wherein the mass ratio of the poly-p-hydroxystyrene homopolymer to the photoinduced deactivator is 100-600: 2-50.
Alternatively, the poly (p-hydroxystyrene) homopolymer has the structural formula:
Figure BDA0003396526410000021
wherein n is an integer greater than 1.
Preferably, the weight average molecular weight of the poly (p-hydroxystyrene) homopolymer is 1000-20000.
Preferably, the photo-deactivator comprises at least one of acetophenone O-benzoyl oxime, nifedipine, 2-nitrophenylmethyl 4-methacryloxypiperidine-1-carboxylate, 1, 2-diisopropyl-3- [ bis (dimethylamino) methylene ] guanidine 2- (3-benzoylphenyl) propionate, and 1, 2-dicyclohexyl-4, 4,5,5 tetramethylbiguanide n-butyltriphenylborate.
Preferably, the composition comprises the following components in parts by mass: 10-60 parts of poly p-hydroxystyrene homopolymer, 2-20 parts of cross-linking agent, 0.2-5 parts of acid catalyst and 0.2-5 parts of photoinduced deactivator.
Preferably, the paint also comprises 5-90 parts of solvent by mass.
Optionally, the cross-linking agent comprises at least one of glycoluril, glycoluril derivatives, 1, 3-bis-methylol urea, 1, 3-dimethyl-2-imidazolidinone.
Preferably, the acidic catalyst comprises an organic acid and/or an inorganic acid.
Preferably, the organic acid comprises at least one of formic acid, acetic acid, propionic acid, methanesulfonic acid, ethanesulfonic acid, propanesulfonic acid and p-toluenesulfonic acid.
Preferably, the inorganic acid includes at least one of hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, and hydrofluoric acid.
Preferably, the solvent comprises an organic solvent.
Preferably, the organic solvent includes at least one of glycol methyl ether, propylene glycol methyl ether acetate, ethyl acetate, and ethyl lactate.
The second aspect of the present invention provides a method for preparing the photoresist composition, which comprises mixing the poly-p-hydroxystyrene homopolymer, the photo-deactivating agent, optionally the cross-linking agent, optionally the acid catalyst and optionally the solvent.
A third aspect of the invention provides the use of the photoresist composition in the manufacture of integrated circuits.
A fourth aspect of the present invention provides a method of forming a photoresist pattern, the method comprising the steps of:
step A: coating a photoresist composition on the target layer to form a photoresist layer;
and B: pre-baking the photoresist layer and then exposing the photoresist layer with actinic radiation to obtain an exposed photoresist layer;
and C: and (4) baking the exposed photoresist layer, adding a developing solution, and developing to obtain the photoresist pattern.
Optionally, the pre-baking temperature is 90-110 ℃.
Preferably, the pre-baking time is 30-90 s.
Preferably, the temperature of the intermediate drying is 120-.
Preferably, the baking time is 30-90 s.
Optionally, a pre-bake, post-exposure to actinic radiation in step B results in a photoresist layer to be exposed.
Preferably, the film thickness of the photoresist layer to be exposed is 500 nm.
Preferably, the developing solution is added in step C for development.
Preferably, the developer solution comprises a tetramethylammonium hydroxide solution, a potassium hydroxide solution or a sodium hydroxide solution.
Compared with the prior art, the invention has at least the following beneficial effects:
the photoresist composition provided by the invention uses a photoinduced deactivator to react with the poly-p-hydroxystyrene homopolymer, and the photoinduced deactivator generates intermediate substances to prevent the cross-linking reaction of the poly-p-hydroxystyrene homopolymer when being exposed, so that the photoresist composition is dissolved in a developing solution to form a positive image. The photoresist composition has strong photosensitivity, and after exposure by adopting a light source of 248nm deep ultraviolet lithography, the exposure dose can be reduced to 10mJ/cm under the film thickness of 500nm2The following. Upon exposure to light, the photoinactivation agent forms a basic compound that deactivates the acidic catalyst and does not catalyze the poly (p-hydroxystyrene) homopolymerThe silicon dioxide film has the advantages that the silicon dioxide film has a crosslinking reaction with a crosslinking agent, but can be subjected to the crosslinking reaction in a non-exposure area, and has a higher carbon atom content due to no protective group, so that the dry etching resistance is obviously improved, the etching ratio is improved, the production efficiency of customers is greatly improved, and the production cost is reduced.
The preparation method of the photoresist composition provided by the invention has the advantages of simple process, large processing capacity, suitability for mass production and low cost.
The application of the photoresist composition provided by the invention in manufacturing integrated circuits improves the production efficiency of the integrated circuits and reduces the production cost.
The method for forming the photoresist pattern ensures that the formed pattern meets the actual process requirement and realizes a better photoresist pattern.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention. The components of embodiments of the present invention may be arranged and designed in a wide variety of different configurations.
In a first aspect of the invention, a photoresist composition is provided comprising a poly (p-hydroxystyrene) homopolymer and a photo-deactivator.
Wherein the mass ratio of the poly-p-hydroxystyrene homopolymer to the photoinduced deactivator is 100-600: 2-50.
The photoresist composition provided by the invention uses a photoinduced deactivator to react with the poly-p-hydroxystyrene homopolymer, and the photoinduced deactivator generates intermediate substances to prevent the cross-linking reaction of the poly-p-hydroxystyrene homopolymer when being exposed, so that the photoresist composition is dissolved in a developing solution to form a positive image. The photoresist composition has strong photosensitivity, and after exposure by adopting a light source of 248nm deep ultraviolet lithography, the exposure dose can be reduced to 10mJ/cm under the film thickness of 500nm2The following. The poly (p-hydroxystyrene) homopolymer has no protective group, can participate in crosslinking, and has high carbon contentThe atomic content obviously improves the dry etching resistance, improves the etching ratio, greatly improves the production efficiency of customers and reduces the production cost.
When the mass ratio of the poly-p-hydroxystyrene homopolymer to the photoinduced deactivator is lower than 100:50, the photoinduced deactivator cannot be normally dissolved in a solvent due to too high ratio, the uniformity of a photoresist film is reduced, and the dry etching resistance is reduced; when the mass ratio of the poly (p-hydroxystyrene) homopolymer to the photo-deactivator is higher than 600:2, the content of the photo-deactivator is too low to be effectively deactivated.
In some preferred embodiments of the present invention, the mass ratio of the poly (p-hydroxystyrene) homopolymer to the photo-deactivator is typically, but not limited to, 100:2, 100:30, 100:50, 200:2, 200:30, 200:50, 300:2, 300:30, 300:50, 400:2, 400:30, 400:50, 500:2, 500:30, 500:50, 600:2, 600:30, or 600: 50.
Alternatively, the poly (p-hydroxystyrene) homopolymer has the structural formula:
Figure BDA0003396526410000051
wherein n is an integer greater than 1.
Preferably, the weight average molecular weight of the poly (p-hydroxystyrene) homopolymer is 1000-20000.
The poly-p-hydroxystyrene homopolymer used in the original 248nm positive photoresist system is acid-sensitive resin, contains a large amount of protecting groups, also contains a methacrylate monomer, can perform decomposition reaction under the action of acid and heat, and removes ester groups to generate hydrophilic acid groups, so that the material system is changed from oleophylic to hydrophilic, and images can be obtained by developing the material system.
The poly p-hydroxystyrene homopolymer selected by the invention does not contain a protective group after exposure, can participate in a crosslinking reaction, and has alkali solubility and excellent dry etching resistance.
When the weight average molecular weight of the poly (p-hydroxystyrene) homopolymer is less than 1000, the molecular weight is too low to effectively crosslink to form macromolecules insoluble in an alkaline developer; when the weight average molecular weight of the poly (p-hydroxystyrene) homopolymer is higher than 20000, it is difficult to dissolve in a solvent and cannot be used as a photoresist resin.
In some embodiments of the invention, the poly (p-hydroxystyrene) homopolymer has a weight average molecular weight of typically, but not limited to, 1000, 2000, 3000, 4000, 5000, 6000, 7000, 8000, 9000, 10000, 11000, 12000, 13000, 14000, 15000, 16000, 17000, 18000, 19000, or 20000.
Preferably, the photo-deactivator comprises at least one of acetophenone O-benzoyl oxime, nifedipine, 2-nitrophenylmethyl 4-methacryloxypiperidine-1-carboxylate, 1, 2-diisopropyl-3- [ bis (dimethylamino) methylene ] guanidine 2- (3-benzoylphenyl) propionate, and 1, 2-dicyclohexyl-4, 4,5,5 tetramethylbiguanide n-butyltriphenylborate.
Under the irradiation of ultraviolet light, the photoinduced deactivator generates a basic compound to perform a neutralization reaction with the acid catalyst, so that the acid catalyst is deactivated and the cross-linking reaction of the poly-p-hydroxystyrene homopolymer cannot be catalyzed. Therefore, in the ultraviolet light irradiation area, the poly p-hydroxystyrene homopolymer is not crosslinked and cured, and is dissolved in an alkaline developing solution to form a positive image in the non-exposure area, so that the fine pattern processing operation is completed.
In some embodiments of the invention, typical but non-limiting photoinducer deactivators are acetophenone O-benzoyl oxime, nifedipine, 2-nitrophenylmethyl 4-methacryloxypiperidine-1-carboxylate, 1, 2-diisopropyl-3- [ bis (dimethylamino) methylene ] guanidine 2- (3-benzoylphenyl) propionate, or 1, 2-dicyclohexyl-4, 4,5,5 tetramethylbiguanide n-butyltriphenylborate.
Preferably, the composition comprises the following components in parts by mass: 10-60 parts of poly p-hydroxystyrene homopolymer, 2-20 parts of cross-linking agent, 0.2-5 parts of acid catalyst and 0.2-5 parts of photoinduced deactivator.
Preferably, the paint also comprises 5-90 parts of solvent by mass.
In some preferred embodiments of the present invention, the mass fraction of the poly (p-hydroxystyrene) homopolymer is typically, but not limited to, 10 parts, 20 parts, 30 parts, 40 parts, 50 parts, or 60 parts; the mass portion of the crosslinking agent is typically, but not limited to, 2 parts, 5 parts, 10 parts, 15 parts, 18 parts, 19 parts or 20 parts; the mass portion of the acidic catalyst is typically, but not limited to, 0.2 parts, 0.5 parts, 1 part, 2 parts, 3 parts, 4 parts or 5 parts; the mass fraction of photo-deactivator is typically, but not limited to, 0.2 parts, 0.5 parts, 1 part, 2 parts, 3 parts, 4 parts or 5 parts.
Optionally, the cross-linking agent comprises at least one of glycoluril, glycoluril derivatives, 1, 3-bis-methylol urea, 1, 3-dimethyl-2-imidazolidinone.
The structural formula of glycoluril is
Figure BDA0003396526410000071
In some embodiments of the invention, the crosslinking agent is typically, but not limited to, glycoluril derivatives, 1, 3-bis-methylol urea, or 1, 3-dimethyl-2-imidazolidinone.
Preferably, the acidic catalyst comprises an organic acid and/or an inorganic acid.
In some embodiments of the invention, the acidic catalyst is typically, but not limited to, an organic acid.
In some embodiments of the invention, the acidic catalyst is typically, but not limited to, an inorganic acid.
In some embodiments of the invention, acidic catalysts are typically, but not limited to, organic and inorganic acids.
Preferably, the organic acid comprises at least one of formic acid, acetic acid, propionic acid, methanesulfonic acid, ethanesulfonic acid, propanesulfonic acid and p-toluenesulfonic acid.
In some embodiments of the invention, the organic acid is typically, but not limited to, formic acid, acetic acid, propionic acid, methanesulfonic acid, ethanesulfonic acid, propanesulfonic acid, or p-toluenesulfonic acid.
Preferably, the inorganic acid includes at least one of hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, and hydrofluoric acid.
In some embodiments of the invention, the inorganic acid is typically, but not limited to, hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, or hydrofluoric acid.
Preferably, the solvent comprises an organic solvent.
Preferably, the organic solvent includes at least one of glycol methyl ether, propylene glycol methyl ether acetate, ethyl acetate, and ethyl lactate.
In some embodiments of the invention, the organic solvent is typically, but not limited to, glycol methyl ether, propylene glycol methyl ether acetate, ethyl acetate, or ethyl lactate.
The second aspect of the present invention provides a method for preparing the photoresist composition, which comprises mixing the poly-p-hydroxystyrene homopolymer, the photo-deactivating agent, optionally the cross-linking agent, optionally the acid catalyst and optionally the solvent.
The preparation method of the photoresist composition provided by the invention has the advantages of simple process, large processing capacity, suitability for mass production and low cost.
A third aspect of the invention provides the use of the photoresist composition in the manufacture of integrated circuits.
The application of the photoresist composition provided by the invention in manufacturing integrated circuits improves the production efficiency of the integrated circuits and reduces the production cost.
A fourth aspect of the present invention provides a method of forming a photoresist pattern, the method comprising the steps of:
step A: coating the photoresist composition according to any one of claims 1 to 5 or the photoresist composition prepared by the preparation method according to claim 6 on a target layer to form a photoresist layer;
and B: pre-baking the photoresist layer and then exposing the photoresist layer with actinic radiation to obtain an exposed photoresist layer;
and C: and (4) baking the exposed photoresist layer, adding a developing solution, and developing to obtain the photoresist pattern.
The method for forming the photoresist pattern ensures that the formed pattern meets the actual process requirement and realizes a better photoresist pattern.
Optionally, the pre-baking temperature is 90-110 ℃.
In some embodiments of the invention, the temperature of the pre-bake is typically, but not limited to, 90 ℃, 95 ℃, 100 ℃, 105 ℃ or 110 ℃.
Preferably, the pre-baking time is 30-90 s.
In some embodiments of the invention, the time of the pre-baking is 30s, 40s, 50s, 60s, 70s, 80s or 90 s.
Preferably, the temperature of the intermediate drying is 120-.
In some embodiments of the invention, the temperature of the medium baking is typically, but not limited to, 120 ℃, 125 ℃, 130 ℃, 135 ℃ or 140 ℃.
Preferably, the baking time is 30-90 s.
In some embodiments of the invention, the intermediate baking time is 30s, 40s, 50s, 60s, 70s, 80s, or 90 s.
Optionally, a pre-bake, post-exposure to actinic radiation in step B results in a photoresist layer to be exposed.
Preferably, the film thickness of the photoresist layer to be exposed is 500 nm.
Preferably, the developing solution is added in step C for development.
Preferably, the developer solution comprises a tetramethylammonium hydroxide solution.
In some embodiments of the present invention, the developer solution is typically, but not limited to, a tetramethylammonium hydroxide solution, a potassium hydroxide solution, or a sodium hydroxide solution.
The concentration of the tetramethylammonium hydroxide solution was 2.38 wt%.
Embodiments of the present invention will be described in detail below with reference to examples, but those skilled in the art will appreciate that the following examples are only illustrative of the present invention and should not be construed as limiting the scope of the present invention.
The specifications and types of the raw materials used in the examples and comparative examples of the present invention are shown in the following table 1, and those who do not indicate specific conditions are performed according to the conventional conditions or conditions suggested by the manufacturer.
TABLE 1 raw material specification and model table
Components Model/specification Manufacturer of the product
Poly (p-hydroxystyrene) resin PHS-6 Shenzhen Hanya Microelectronics Technology Co.,Ltd.
Glycolurils CAS number 496-46-8 Aladdin reagent
1, 3-bis (hydroxymethyl) urea CAS number 140-95-4 Aladdin reagent
Acetic acid CAS number 64-19-7 Aladdin reagent
Acetophenone O-benzoyl oxime CAS number 26060-56-0 Aladdin reagent
Propylene glycol methyl ether acetate CAS number 108-65-6 Aladdin reagent
Ethanesulfonic acid CAS number 7365-44-8 Aladdin reagent
Sulfuric acid Analytical purity Yantai Far East Fine Chemical Co.,Ltd.
Propylene glycol methyl ether CAS number 107-98-2 Aladdin reagent
Example 1
This example provides a photoresist composition obtained by uniformly mixing 20g of a polyhydroxystyrene resin having a weight average molecular weight of 10000, 2g of glycoluril, 0.18g of acetic acid, 0.44g of acetophenone O-benzoyl oxime, and 100g of propylene glycol methyl ether acetate, and filtering the mixture through a filter having a pore size of 0.05. mu.m.
Example 2
This example provides a photoresist composition, which is prepared by mixing 20g of polyhydroxystyrene resin with a weight average molecular weight of 10000, 2g of 1, 3-dimethylol urea, 0.2g of ethanesulfonic acid, 0.48g of acetophenone oxime-O-benzoyl and 100g of propylene glycol methyl ether acetate, and filtering the mixture with a filter membrane with a pore size of 0.05 μm.
Example 3
This example provides a photoresist composition obtained by uniformly mixing 20g of a polyhydroxystyrene resin having a weight average molecular weight of 10000, 1.2g of glycoluril, 0.2g of sulfuric acid, 0.5g of acetophenone oxime, and 100g of propylene glycol methyl ether, and filtering the mixture through a filter having a pore size of 0.05. mu.m.
Example 4
This example provides a photoresist composition obtained by uniformly mixing 20g of polyhydroxystyrene resin having a weight average molecular weight of 5000, 1.2g of glycoluril, 0.2g of sulfuric acid, 0.5g of acetophenone oxime-benzoyl and 100g of propylene glycol methyl ether, and filtering the mixture through a filter having a pore size of 0.05. mu.m.
Example 5
This example provides a photoresist composition, which is different from example 1 in that the weight average molecular weight of the poly-p-hydroxystyrene resin is 20000, and other raw materials and preparation methods are the same as example 1 and are not repeated herein.
Comparative example 1
The comparative example provides a photoresist composition, which is a deprotected KrF photoresist product, specifically SUN-KrF100, and StartIke as a manufacturer.
Test example 1
The photoresist compositions provided in examples 1 to 5 and comparative example 1 were spin-coated on the treated silicon wafer, respectively, and Prebaked (PAB) using a hot plate at a prebaking temperature of 100 c for a prebaking time of 60s while adjusting the rotation speed so that the film thickness after drying becomes 500 nm. After exposure by a KrF exposure machine (pattern size 200nm), the resultant was baked in a hot Plate (PEB) at a medium baking temperature of 130 ℃ for 60 seconds. Soaking and developing for 40s by using 2.38 wt% of tetramethylammonium hydroxide solution (TMAH), and cleaning by using deionized water to finish the photoetching process to obtain a positive image. The width of the lines in the resulting positive images was measured separately and the exposure dose was recorded when the line width was 200nm, as reported in table 2.
Test example 2
The silicon wafer substrate obtained in test example 1 was etched by inductively coupled plasma, the etching gas was carbon tetrafluoride, the flow rate was 40ml/min, the ICP power was 280W, the radio frequency power was 50W, the etching pressure was 0.4Pa, and etching was performed for 400s, the film thickness loss of the photoresist and the etching depth of the substrate were measured by a step profiler, the etching ratio was calculated from the film thickness loss/the substrate etching depth, and the results are recorded in table 2.
TABLE 2 lithography Performance data sheet
Figure BDA0003396526410000111
Figure BDA0003396526410000121
As can be seen from Table 2, examples 1-5 provided photoresist compositions having a lower exposure dose than the photoresist composition provided in comparative example 1, and had significantly better dry etch resistance than comparative example 1.
Finally, it should be noted that: the above embodiments are only used to illustrate the technical solution of the present invention, and not to limit the same; while the invention has been described in detail and with reference to the foregoing embodiments, it will be understood by those skilled in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some or all of the technical features may be equivalently replaced; and the modifications or the substitutions do not make the essence of the corresponding technical solutions depart from the scope of the technical solutions of the embodiments of the present invention.

Claims (10)

1. A photoresist composition comprising a poly-p-hydroxystyrene homopolymer and a photo-deactivator;
wherein the mass ratio of the poly-p-hydroxystyrene homopolymer to the photoinduced deactivator is 100-600: 2-50.
2. The photoresist composition of claim 1, wherein the poly-p-hydroxystyrene homopolymer has the formula:
Figure FDA0003396526400000011
wherein n is an integer greater than 1;
preferably, the weight average molecular weight of the poly (p-hydroxystyrene) homopolymer is 1000-20000.
3. The photoresist composition of claim 1, wherein the photo-deactivating agent comprises at least one of acetophenone O-benzoyl oxime, nifedipine, 2-nitrophenylmethyl 4-methacryloxypiperidine-1-carboxylate, 1, 2-diisopropyl-3- [ bis (dimethylamino) methylene ] guanidine 2- (3-benzoylphenyl) propionate, and 1, 2-dicyclohexyl-4, 4,5,5 tetramethylbiguanide n-butyltriphenylborate.
4. The photoresist composition according to claim 1, comprising the following components in parts by mass: 10-60 parts of poly-p-hydroxystyrene homopolymer, 2-20 parts of cross-linking agent, 0.2-5 parts of acid catalyst and 0.2-5 parts of photoinduced deactivator;
preferably, the paint also comprises 5-90 parts of solvent by mass.
5. The photoresist composition of claim 4, wherein the cross-linking agent comprises at least one of glycoluril, glycoluril derivatives, 1, 3-bis-methylol urea, and 1, 3-dimethyl-2-imidazolidinone;
preferably, the acidic catalyst comprises an organic acid and/or an inorganic acid;
preferably, the organic acid comprises at least one of formic acid, acetic acid, propionic acid, methanesulfonic acid, ethanesulfonic acid, propanesulfonic acid, and p-toluenesulfonic acid;
preferably, the inorganic acid includes at least one of hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, and hydrofluoric acid;
preferably, the solvent comprises an organic solvent;
preferably, the organic solvent includes at least one of glycol methyl ether, propylene glycol methyl ether acetate, ethyl acetate, and ethyl lactate.
6. The method for preparing a photoresist composition according to any one of claims 1 to 5, wherein the poly-p-hydroxystyrene homopolymer, the photo-deactivating agent, optionally the cross-linking agent, optionally the acid catalyst, and optionally the solvent are mixed uniformly.
7. Use of a photoresist composition according to any one of claims 1 to 5 or prepared by the method of claim 6 in the manufacture of an integrated circuit.
8. A method of forming a photoresist pattern, the method comprising the steps of:
step A: coating the photoresist composition according to any one of claims 1 to 5 or the photoresist composition prepared by the preparation method according to claim 6 on a target layer to form a photoresist layer;
and B: pre-baking the photoresist layer and then exposing the photoresist layer with actinic radiation to obtain an exposed photoresist layer;
and C: and baking the exposed photoresist layer and developing to obtain the photoresist pattern.
9. The method of forming a photoresist pattern according to claim 8, wherein the temperature of the pre-baking is 90-110 ℃;
preferably, the pre-baking time is 30-90 s;
preferably, the temperature of the intermediate drying is 120-140 ℃;
preferably, the baking time is 30-90 s.
10. The method of forming a photoresist pattern according to claim 8, wherein a photoresist layer to be exposed is obtained before the exposure to actinic radiation after the prebaking in step B;
preferably, the film thickness of the photoresist layer to be exposed is 500 nm;
preferably, a developing solution is added in the step C for development;
preferably, the developer solution comprises a tetramethylammonium hydroxide solution, a potassium hydroxide solution or a sodium hydroxide solution.
CN202111483647.0A 2021-12-07 2021-12-07 Photoresist composition, preparation method and application thereof, and method for forming photoresist pattern Pending CN114167684A (en)

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