CN111999983A - Negative high-resolution photoresist - Google Patents

Negative high-resolution photoresist Download PDF

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CN111999983A
CN111999983A CN202011044016.4A CN202011044016A CN111999983A CN 111999983 A CN111999983 A CN 111999983A CN 202011044016 A CN202011044016 A CN 202011044016A CN 111999983 A CN111999983 A CN 111999983A
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reaction
film
negative high
photoresist
forming resin
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邵杰
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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
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F292/00—Macromolecular compounds obtained by polymerising monomers on to inorganic 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
    • G03F7/004—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
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds

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  • Chemical & Material Sciences (AREA)
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  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Materials For Photolithography (AREA)

Abstract

The invention relates to the field of optical materials, in particular to a negative high-resolution photoresist. The commercial alkali-soluble negative high-resolution photoresist is mainly acrylic acid modified epoxy resin, but the resin has high brittleness, line edge roughness is easily caused during development, and the film-forming resin contains a large amount of oily functional groups, so that the adhesion of the film-forming resin on a silicon wafer is low. Based on the problems, S, N, Si heteroatoms and a large amount of hydroxyl are introduced into the photoresist film-forming resin through the modified nano silicon dioxide and the N- (5-norbornene-2-methyl) -methanesulfonamide, so that the resolution and LER of the photoresist are effectively improved, the adhesion of the film-forming resin on a silicon wafer is improved, and the negative high-resolution photoresist has a good application prospect.

Description

Negative high-resolution photoresist
Technical Field
The invention relates to the field of optical materials, in particular to a negative high-resolution photoresist.
Background
The photoresist is photosensitive mixed liquid with the solubility changed in a developing solution by the irradiation or radiation of an ultraviolet exposure light source, is a key material of an integrated circuit industrial chain, and is mainly applied to the fine pattern processing of microelectronic and semiconductor discrete devices.
The photoresist comprises film-forming resin, a photosensitizer, an auxiliary agent, a solvent and the like, wherein the film-forming resin is a key component and can generate photochemical reaction to determine the sensitivity, resolution and solubility of the photoresist.
Commercial alkali-soluble negative high-resolution photoresists are mainly acrylic-modified epoxy resins, but the resins are very brittle and easily cause line edge roughness during development (synthesis and performance research [ D ] of film-forming resins for the photoresists), and the film-forming resins contain a large amount of oily functional groups so that the adhesion of the film-forming resins on silicon wafers is small.
The introduction of heteroatoms such as S, F into a film-forming resin of a photoresist can improve the resolution of the photoresist, but the study on the influence of two or more heteroatoms introduced into a molecular chain of the film-forming resin of the photoresist on the resolution is rarely reported at present.
Disclosure of Invention
Aiming at the problems in the prior art, the technical problems to be solved by the invention are as follows: the commercial alkali-soluble negative high-resolution photoresist is mainly acrylic acid modified epoxy resin, but the resin has high brittleness, line edge roughness is easily caused during development, and the film-forming resin contains a large amount of oily functional groups, so that the adhesion of the film-forming resin on a silicon wafer is low.
The technical scheme adopted by the invention for solving the technical problems is as follows: the invention provides a negative high-resolution photoresist which comprises the following components in parts by weight:
Figure BDA0002707453230000011
Figure BDA0002707453230000021
specifically, the film-forming resin is prepared according to the following method:
(1) uniformly mixing 45mL of tert-butyl acrylate, 5g of modified nano-silica, 30mLN- (5-norbornene-2-methyl) -methanesulfonamide, 15mL of butyl methacrylate, 35mL of methyl methacrylate, 20mL of maleic anhydride, 3mL of azobisisobutyronitrile, 2.5mL of chain transfer agent and 150mL of propylene glycol methyl ether acetate, setting the reaction temperature to 90 ℃, starting a stirrer, fully reacting under the protection of nitrogen, and stopping the reaction after infrared detection of disappearance of double bonds in a reaction system to obtain a copolymer I;
(2) raising the temperature of the reaction system to 115 ℃, adding 0.2g of p-methoxyphenol, 1g of triphenylphosphine and 50mL of propylene glycol monomethyl ether acetate, uniformly mixing, dropwise adding 30mL of 2-hydroxyethyl methacrylate into the reaction system in the continuous stirring process, completing dropwise adding within 10min until the acid value of the reaction system is not changed, finishing the reaction, dissolving the reaction solution by acetone, dropwise adding into petroleum ether for precipitation, performing suction filtration, dissolving by acetone, precipitating, repeating for three times, and finally placing in a vacuum drying box at 30 ℃ for 24h to obtain the film-forming resin.
Specifically, the modified nano-silica is prepared according to the following method:
adding 50g of nano-silica, 50g of gamma- (methacryloyloxy) propyl trimethoxy silane, 1.5g of maleic anhydride and 10mL of water into acetone in sequence, heating to reflux, carrying out heat preservation reaction for 2 hours, washing with toluene after the reaction is finished, and finally drying the washed product to obtain the modified nano-silica, wherein the structural formula of the modified nano-silica is as follows:
Figure BDA0002707453230000022
specifically, the photoinitiator is a compound of a photoinitiator 907 and a photoinitiator ITX, and the weight ratio of the photoinitiator 907 to the photoinitiator ITX is 1: 2.
Specifically, the reactive diluent is tripropylene glycol diacrylate or hydroxyethyl acrylate.
Specifically, the solvent is acetone or N, N dimethylformamide.
The invention has the beneficial effects that:
(1) according to the invention, S, N is introduced into the molecular structure of the film-forming resin of the photoresist through N- (5-norbornene-2-methyl) -methanesulfonamide, Si heteroatom is introduced through modified nano-silica, S, N, Si heteroatom is introduced to greatly improve the polarity and refractive index of the resin, S, N, Si synergistic effect enables the film-forming resin to obtain high refractive index and exposure latitude at the same time, and finally the photoresist obtains higher resolution;
(2) the surface of the modified nano silicon dioxide prepared by the invention contains abundant hydroxyl groups, so that the adhesive force of the photoresist on a silicon wafer is effectively improved, however, excessive modified silicon dioxide cannot be introduced into film-forming resin, and the molecular structure of the modified nano silicon dioxide contains more oxygen elements, so that the anti-etching capability of the photoresist is reduced, the photoresist has higher etching rate, and simultaneously, the LER of the photoresist is also higher;
(3) according to the invention, maleic anhydride is adopted to replace acrylic acid as a component for introducing carboxyl and a double bond into the film-forming resin, and compared with the condition that after acrylic maleic anhydride reacts with 2-hydroxyethyl methacrylate, one carboxyl and one double bond are introduced at the same time, the condition that the carboxyl in the film-forming resin has to be consumed while the double bond is introduced is avoided, the content of the carboxyl in the film-forming resin is effectively ensured, and the alkali solubility of an unexposed area of the film-forming resin is greatly improved.
Detailed Description
The present invention will now be described in further detail with reference to examples.
The film-forming resins used in the following examples and comparative examples of the invention were prepared as follows:
(1) uniformly mixing 45mL of tert-butyl acrylate, 5g of modified nano-silica, 30mLN- (5-norbornene-2-methyl) -methanesulfonamide, 15mL of butyl methacrylate, 35mL of methyl methacrylate, 20mL of maleic anhydride, 3mL of azobisisobutyronitrile, 2.5mL of chain transfer agent and 150mL of propylene glycol methyl ether acetate, setting the reaction temperature to 90 ℃, starting a stirrer, fully reacting under the protection of nitrogen, and stopping the reaction after infrared detection of disappearance of double bonds in a reaction system to obtain a copolymer I;
(2) raising the temperature of the reaction system to 115 ℃, adding 0.2g of p-methoxyphenol, 1g of triphenylphosphine and 50mL of propylene glycol monomethyl ether acetate, uniformly mixing, dropwise adding 30mL of 2-hydroxyethyl methacrylate into the reaction system in the continuous stirring process, completing dropwise adding within 10min until the acid value of the reaction system is not changed, finishing the reaction, dissolving the reaction solution by acetone, dropwise adding into petroleum ether for precipitation, performing suction filtration, dissolving by acetone, precipitating, repeating for three times, and finally placing in a vacuum drying box at 30 ℃ for 24h to obtain the film-forming resin.
The modified nano-silica used in the following examples and comparative examples of the present invention was prepared according to the following method:
adding 50g of nano-silica, 50g of gamma- (methacryloyloxy) propyl trimethoxy silane, 1.5g of maleic anhydride and 10mL of water into acetone in sequence, heating to reflux, carrying out heat preservation reaction for 2 hours, washing with toluene after the reaction is finished, and finally drying the washed product to obtain the modified nano-silica.
The nano-silica used in the following examples and comparative examples of the present invention has an average particle size of 10 to 20 nm.
The photoinitiator used in the following examples and comparative examples of the present invention was a compound of photoinitiator 907 and photoinitiator ITX, and the weight ratio of photoinitiator 907 to photoinitiator ITX was 1: 2.
The reactive diluents used in the following examples and comparative examples of the present invention were tripropylene glycol diacrylate or hydroxyethyl acrylate.
The solvents used in the following examples and comparative examples of the present invention were acetone or N, N dimethylformamide.
Example 1
The negative high-resolution photoresist comprises the following components in parts by weight:
Figure BDA0002707453230000051
example 2
The negative high-resolution photoresist comprises the following components in parts by weight:
Figure BDA0002707453230000052
example 3
The negative high-resolution photoresist comprises the following components in parts by weight:
Figure BDA0002707453230000053
comparative example 1 is the same as example 3 except that the film-forming resin was prepared as follows:
(1) uniformly mixing 45mL of tert-butyl acrylate, 10g of modified nano-silica, 30mLN- (5-norbornene-2-methyl) -methanesulfonamide, 15mL of butyl methacrylate, 35mL of methyl methacrylate, 20mL of maleic anhydride, 3mL of azobisisobutyronitrile, 2.5mL of chain transfer agent and 150mL of propylene glycol methyl ether acetate, setting the reaction temperature to 90 ℃, starting a stirrer, fully reacting under the protection of nitrogen, and stopping the reaction after infrared detection of disappearance of double bonds in a reaction system to obtain a copolymer I;
(2) raising the temperature of the reaction system to 115 ℃, adding 0.2g of p-methoxyphenol, 1g of triphenylphosphine and 50mL of propylene glycol monomethyl ether acetate, uniformly mixing, dropwise adding 30mL of 2-hydroxyethyl methacrylate into the reaction system in the continuous stirring process, completing dropwise adding within 10min until the acid value of the reaction system is not changed, finishing the reaction, dissolving the reaction solution by acetone, dropwise adding into petroleum ether for precipitation, performing suction filtration, dissolving by acetone, precipitating, repeating for three times, and finally placing in a vacuum drying box at 30 ℃ for 24h to obtain the film-forming resin.
Comparative example 2 the same as example 3 except that the film forming resin was prepared as follows:
(1) uniformly mixing 45mL of tert-butyl acrylate, 0.5g of modified nano-silica, 30mLN- (5-norbornene-2-methyl) -methanesulfonamide, 15mL of butyl methacrylate, 35mL of methyl methacrylate, 20mL of maleic anhydride, 3mL of azobisisobutyronitrile, 2.5mL of chain transfer agent and 150mL of propylene glycol methyl ether acetate, setting the reaction temperature to 90 ℃, starting a stirrer, fully reacting under the protection of nitrogen, and stopping the reaction after infrared detection of disappearance of double bonds in the reaction system to obtain a copolymer I;
(2) raising the temperature of the reaction system to 115 ℃, adding 0.2g of p-methoxyphenol, 1g of triphenylphosphine and 50mL of propylene glycol monomethyl ether acetate, uniformly mixing, dropwise adding 30mL of 2-hydroxyethyl methacrylate into the reaction system in the continuous stirring process, completing dropwise adding within 10min until the acid value of the reaction system is not changed, finishing the reaction, dissolving the reaction solution by acetone, dropwise adding into petroleum ether for precipitation, performing suction filtration, dissolving by acetone, precipitating, repeating for three times, and finally placing in a vacuum drying box at 30 ℃ for 24h to obtain the film-forming resin.
Comparative example 3 differs from example 3 in that:
the film-forming resin was prepared as follows:
(1) uniformly mixing 45mL of tert-butyl acrylate, 30mL of LN- (5-norbornene-2-methyl) -methanesulfonamide, 15mL of butyl methacrylate, 35mL of methyl methacrylate, 20mL of maleic anhydride, 3mL of azobisisobutyronitrile, 2.5mL of chain transfer agent and 150mL of propylene glycol monomethyl ether acetate, setting the reaction temperature to 90 ℃, starting a stirrer, fully reacting under the protection of nitrogen, and stopping the reaction after infrared detection of disappearance of double bonds in a reaction system to obtain a copolymer I;
(2) raising the temperature of the reaction system to 115 ℃, adding 0.2g of p-methoxyphenol, 1g of triphenylphosphine and 50mL of propylene glycol monomethyl ether acetate, uniformly mixing, dropwise adding 30mL of 2-hydroxyethyl methacrylate into the reaction system in the continuous stirring process, completing dropwise adding within 10min until the acid value of the reaction system is not changed, finishing the reaction, dissolving the reaction solution by acetone, dropwise adding into petroleum ether for precipitation, performing suction filtration, dissolving by acetone, precipitating, repeating for three times, and finally placing in a vacuum drying box at 30 ℃ for 24h to obtain the film-forming resin.
Comparative example 4 differs from example 3 in that:
(1) uniformly mixing 45mL of tert-butyl acrylate, 5g of modified nano-silica, 15mL of butyl methacrylate, 35mL of methyl methacrylate, 20mL of maleic anhydride, 3mL of azobisisobutyronitrile, 2.5mL of chain transfer agent and 150mL of propylene glycol monomethyl ether acetate, setting the reaction temperature to be 90 ℃, starting a stirrer, fully reacting under the protection of nitrogen, and stopping the reaction after infrared detection of double bonds in a reaction system to obtain a copolymer I;
(2) raising the temperature of the reaction system to 115 ℃, adding 0.2g of p-methoxyphenol, 1g of triphenylphosphine and 50mL of propylene glycol monomethyl ether acetate, uniformly mixing, dropwise adding 30mL of 2-hydroxyethyl methacrylate into the reaction system in the continuous stirring process, completing dropwise adding within 10min until the acid value of the reaction system is not changed, finishing the reaction, dissolving the reaction solution by acetone, dropwise adding into petroleum ether for precipitation, performing suction filtration, dissolving by acetone, precipitating, repeating for three times, and finally placing in a vacuum drying box at 30 ℃ for 24h to obtain the film-forming resin.
Comparative example 5 differs from example 3 in that:
(1) uniformly mixing 45mL of tert-butyl acrylate, 15mL of butyl methacrylate, 35mL of methyl methacrylate, 20mL of maleic anhydride, 3mL of azobisisobutyronitrile, 2.5mL of chain transfer agent and 150mL of propylene glycol methyl ether acetate, setting the reaction temperature to 90 ℃, starting a stirrer, fully reacting under the protection of nitrogen, and stopping the reaction after infrared detection of disappearance of double bonds in the reaction system to obtain a copolymer I;
(2) raising the temperature of the reaction system to 115 ℃, adding 0.2g of p-methoxyphenol, 1g of triphenylphosphine and 50mL of propylene glycol monomethyl ether acetate, uniformly mixing, dropwise adding 30mL of 2-hydroxyethyl methacrylate into the reaction system in the continuous stirring process, completing dropwise adding within 10min until the acid value of the reaction system is not changed, finishing the reaction, dissolving the reaction solution by acetone, dropwise adding into petroleum ether for precipitation, performing suction filtration, dissolving by acetone, precipitating, repeating for three times, and finally placing in a vacuum drying box at 30 ℃ for 24h to obtain the film-forming resin.
The photoresists prepared in examples 1-3 and comparative examples 1-5 were mixed according to the formula amount and placed in a brown bottle, after all the photoresists were dissolved, insoluble impurities of more than 0.22 μm were removed to obtain a prepared photoresist for standby, the prepared photoresist was spin-coated on a substrate to obtain a coating film with a thickness of 1 μm, and the coating film was subjected to the previous stepBaking (90 deg.C) for 30min, and exposing under UV lamp (exposure energy is 35 mJ/cm)2) And then developing the image in a sodium carbonate solution with the mass fraction of 1% for 35s, then placing the image in deionized water for washing, and post-baking (120 ℃) for 30min to obtain a photoetching image.
The adhesion of the photoresist to the silicon wafer was tested according to GB/T9286-1998, shown in Table 1.
And (3) testing the resolution ratio: observing the line width and line type of the photoresist image by using a KH-8700 type expensive digital video microscope, and observing the resolution of the photoresist by using an S-4800 type scanning electron microscope of Hitachi, Japan;
the photoresists prepared in examples 1-3 and comparative examples 1-5 were evaluated for etch resistance under oxide etch conditions (Ar/CF 2).
The resolution, LER, etch rate of developed images of the photoresists prepared in examples 1-3 and comparative examples 1-5 are shown in Table 1:
TABLE 1
Test item Resolution (nm) LER(nm) Adhesion (grade) Etch rate
Example 1 61 8.6 0 652
Example 2 58 8.8 0 655
Example 3 53 8.4 0 647
Comparative example 1 55 8.7 0 832
Comparative example 2 65 9.3 1 640
Comparative example 3 89 17.1 2 642
Comparative example 4 74 12.4 0 731
Comparative example 5 125 25.2 2 921
In light of the foregoing description of the preferred embodiment of the present invention, many modifications and variations will be apparent to those skilled in the art without departing from the spirit and scope of the invention. The technical scope of the present invention is not limited to the content of the specification, and must be determined according to the scope of the claims.

Claims (5)

1. A negative high-resolution photoresist is characterized by comprising the following components in parts by weight:
25-30 parts of film-forming resin
0.3 to 0.5 portion of pigment
3-5 parts of photoinitiator
8-10 parts of reactive diluent
50-55 parts of organic solvent.
The negative high resolution photoresist of claim 1, wherein: the film-forming resin is prepared according to the following method:
(1) uniformly mixing 45mL of tert-butyl acrylate, 5g of modified nano-silica, 30mLN- (5-norbornene-2-methyl) -methanesulfonamide, 15mL of butyl methacrylate, 35mL of methyl methacrylate, 20mL of maleic anhydride, 3mL of azobisisobutyronitrile, 2.5mL of chain transfer agent and 150mL of propylene glycol methyl ether acetate, setting the reaction temperature to 90 ℃, starting a stirrer, fully reacting under the protection of nitrogen, and stopping the reaction after infrared detection of disappearance of double bonds in a reaction system to obtain a copolymer I;
(2) raising the temperature of the reaction system to 115 ℃, adding 0.2g of p-methoxyphenol, 1g of triphenylphosphine and 50mL of propylene glycol monomethyl ether acetate, uniformly mixing, dropwise adding 30mL of 2-hydroxyethyl methacrylate into the reaction system in the continuous stirring process, completing dropwise adding within 10min until the acid value of the reaction system is not changed, finishing the reaction, dissolving the reaction solution by acetone, dropwise adding into petroleum ether for precipitation, performing suction filtration, dissolving by acetone, precipitating, repeating for three times, and finally placing in a vacuum drying box at 30 ℃ for 24h to obtain the film-forming resin.
2. The negative high resolution photoresist of claim 2, wherein: the modified nano silicon dioxide is prepared by the following method:
adding 50g of nano-silica, 50g of gamma- (methacryloyloxy) propyl trimethoxy silane, 1.5g of maleic anhydride and 10mL of water into acetone in sequence, heating to reflux, carrying out heat preservation reaction for 2 hours, washing with toluene after the reaction is finished, and finally drying the washed product to obtain the modified nano-silica.
3. The negative high-resolution photoresist according to claim 1, wherein the photoinitiator is a compound of a photoinitiator 907 and a photoinitiator ITX, and the weight ratio of the photoinitiator 907 to the photoinitiator ITX is 1: 2.
4. The negative high resolution photoresist of claim 1, wherein: the reactive diluent is tripropylene glycol diacrylate or hydroxyethyl acrylate.
5. The negative high resolution photoresist of claim 1, wherein: the solvent is acetone or N, N-dimethylformamide.
CN202011044016.4A 2020-09-28 2020-09-28 Negative high-resolution photoresist Pending CN111999983A (en)

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Application Number Priority Date Filing Date Title
CN202011044016.4A CN111999983A (en) 2020-09-28 2020-09-28 Negative high-resolution photoresist

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Application publication date: 20201127