CN112650023B - High-resolution photoresist composition and application thereof - Google Patents
High-resolution photoresist composition and application thereof Download PDFInfo
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- CN112650023B CN112650023B CN202011536992.1A CN202011536992A CN112650023B CN 112650023 B CN112650023 B CN 112650023B CN 202011536992 A CN202011536992 A CN 202011536992A CN 112650023 B CN112650023 B CN 112650023B
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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
- G03F7/022—Quinonediazides
- G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
- G03F7/0233—Macromolecular quinonediazides; Macromolecular additives, e.g. binders characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides
- G03F7/0236—Condensation products of carbonyl compounds and phenolic compounds, e.g. novolak resins
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/34—Introducing sulfur atoms or sulfur-containing groups
- C08F8/36—Sulfonation; Sulfation
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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
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Abstract
The invention provides a high-resolution photoresist composition and application thereof, wherein the high-resolution photoresist composition comprises the following raw material components in parts by mass: 10-30 parts of phenolic resin, 1-20 parts of photosensitive reinforcing resin, 1-3 parts of photosensitizer and 70-100 parts of organic solvent. The photoresist composition optimizes the photosensitive performance by adding the photosensitive enhancement resin, so that the composition has higher resolution and is suitable for micromachining in multiple fields such as touch screens, flat panel displays, integrated circuits and the like.
Description
Technical Field
The invention relates to the technical field of photoetching, in particular to a high-resolution photoresist composition and application thereof.
Background
Photoresist is a resist film material whose solubility is changed by irradiation or radiation from an exposure source such as ultraviolet light, electron beam, excimer laser beam, X-ray, ion beam, or the like. The method is mainly used for photoetching in the process of transferring patterns from a mask plate to a chip, is a key material in the photoetching process, and is developed along with the development of an integrated circuit and is updated continuously. The photoresist has a positive photoresist and a negative photoresist. After exposure, the part of the positive photoresist which is subjected to illumination becomes easy to dissolve, and after development, the positive photoresist is dissolved, and only the part which is not subjected to illumination is left to form a pattern; the negative photoresist is just opposite, after exposure, the illuminated part becomes insoluble, after development, the negative photoresist which is formed by the pattern on the illuminated part is left to be earliest in application in the photoetching process, the process cost is low, the yield is high, but the resolution (namely the minimum pattern can be formed in the photoetching process) is inferior to that of the positive photoresist due to the expansion of the negative photoresist after absorbing the developing solution, so that the positive photoresist is mainly used as the photoresist for the processing technology of submicron or smaller size.
The positive photoresist used in the prior art is mostly diazonaphthoquinone/phenolic resin type photoresist, wherein linear phenolic resin is used as film forming resin, diazonaphthoquinone sulfonate is used as photosensitizer, the diazonaphthoquinone sulfonate can obviously reduce the solubility of the linear phenolic resin in alkaline developer, and after exposure, the diazonaphthoquinone sulfonate can photolyze and rearrange to generate carboxylic acid, so that the dissolution speed of a system in the developer is improved by tens to nearly thousands times.
For example, in publication CN101561632a, a photoresist composition in which an alkali-soluble resin is a salicylaldehyde phenol resin and a photosensitizer is an o-azido naphthoquinone compound, and a method for manufacturing a display panel using the same are proposed, and a pattern formed using such a photoresist composition exhibits heat resistance up to 140 ℃. Although the photoresist resin of the present invention can achieve pattern uniformity by satisfying heat resistance, photosensitivity and film thickness uniformity, the line width of the formed photolithographic image is 3 μm or more, and resolution cannot satisfy the requirement of high resolution.
With the development of the microelectronics industry in recent years, the integrated circuit integration level is higher and the processing line width is reduced gradually, and higher requirements are also put on the resolution of photoresist, so that the development of photoresist compositions capable of meeting higher resolution is urgently needed.
Disclosure of Invention
Based on the technical problems in the background art, the invention provides a high-resolution photoresist composition, which optimizes the photosensitive performance by adding photosensitive enhancement resin, so that the composition has higher resolution and is suitable for micromachining in various fields such as touch screens, flat panel displays, integrated circuits and the like.
The invention provides a high-resolution photoresist composition, which comprises the following raw material components in parts by mass: 10-30 parts of phenolic resin, 1-20 parts of photosensitive reinforcing resin, 1-3 parts of photosensitizer and 70-100 parts of organic solvent;
wherein the photosensitive reinforced resin has the chemical structure shown as follows:
x, y and z are mole fractions of corresponding monomers, x is more than or equal to 0.1 and less than or equal to 0.5, y is more than or equal to 0.1 and less than or equal to 0.3, and x+y+z=1.
Preferably, the phenolic resin is a novolac resin;
preferably, the phenolic novolac resin is produced by polycondensation of a phenolic compound of m-cresol and p-cresol and an aldehyde compound of formaldehyde.
Preferably, the weight average molecular weight of the phenolic novolac resin is 2000-30000.
Preferably, the photosensitive reinforced resin is formed by esterification reaction of a polymer shown in formula 2 and 2-diazonium-1-naphthoquinone-5-sulfonyl chloride, wherein the polymer shown in formula 2 has the following chemical structure:
x, y and z are mole fractions of corresponding monomers, x is more than or equal to 0.1 and less than or equal to 0.5, y is more than or equal to 0.1 and less than or equal to 0.3, and x+y+z=1.
Preferably, the dosage ratio of the polymer shown in the formula 2 to the 2-diazonium-1-naphthoquinone-5-sulfonyl chloride is 2-6:1.
Preferably, the photosensitizer is an ester of 2,3, 4' -tetrahydroxybenzophenone and 2,1, 5-diazonaphthoquinone sulfonyl chloride or an ester of 2,2', 4' -tetrahydroxybenzophenone and 2,1, 5-diazonaphthoquinone sulfonyl chloride.
Preferably, the organic solvent is at least one of ethyl lactate, ethyl acetate, n-butyl acetate, ethylene glycol monomethyl ether, diethylene glycol dimethyl ether, propylene glycol methyl ether acetate, propylene glycol monomethyl ether or diethylene glycol monomethyl ether.
Preferably, the photosensitive photoresist composition further comprises at least one of a leveling agent, a colorant, a plasticizer, or a surfactant.
The invention also provides application of the photosensitive photoresist composition in a photoetching process.
According to the photosensitive photoresist composition, the photosensitive enhancement resin is introduced into the formula, and the diazonaphthoquinone group is grafted on the polyhydroxystyrene copolymer and can form a hydrogen bond with the hydroxyl group of the phenolic resin, so that the compatibility of the photosensitive enhancement resin and the phenolic resin is enhanced, compared with a common photosensitizer, the solubility of the photosensitive enhancement resin in an alkaline developing solution when the photosensitive enhancement resin is not exposed is very low, and the dissolution inhibition performance of the phenolic resin before exposure is necessarily enhanced when the photosensitive enhancement resin is coupled with the phenolic resin through the hydrogen bond, and meanwhile, the solubility of the photosensitive enhancement resin in the alkaline developing solution after exposure is remarkably improved due to the photosensitive enhancement resin has photosensitive performance, so that the solubility of the phenolic resin after exposure is not influenced. Therefore, the invention improves the dissolution rate contrast of the exposure area and the non-exposure area with respect to the introduction of the photosensitive enhancement resin, and finally effectively improves the resolution.
Detailed Description
The technical scheme of the present invention will be described in detail by means of specific examples, which should be explicitly set forth for illustration, but should not be construed as limiting the scope of the present invention.
Example 1
A high resolution photoresist composition comprising the following raw materials by weight: 15g of phenolic resin, 5g of photosensitive reinforcing resin, 2g of 2,3, 4' -tetrahydroxybenzophenone-1, 2-diazonaphthoquinone-5-sulfonate and 85g of propylene glycol methyl ether acetate;
wherein the phenolic resin is linear phenolic resin, and is synthesized by the following method: adding 30g of m-cresol, 30g of p-phenol and 0.2g of oxalic acid into a reaction kettle, uniformly mixing, adding 10g of formalin solution (36.9 wt%) under the protection of nitrogen, heating to 40 ℃ for reaction for 1h, then continuously heating to 100 ℃ for reaction for 2h, then adding 20g of formalin solution (36.9 wt%) and 0.2g of oxalic acid, continuously reacting for 5h at 100 ℃, and distilling to remove water and unreacted monomers to obtain the linear phenolic resin;
the photosensitive reinforced resin is synthesized by the following method: dissolving 20g of 4-acetoxystyrene, 5g of tert-butyl acrylate and 16g of styrene in 300mL of tetrahydrofuran, adding 0.8g of azodiisobutyronitrile AIBN under the protection of nitrogen, heating to 40 ℃ to react for 0.5h, continuing to heat to reflux for 10h, cooling to room temperature after the reaction is finished, adding a large amount of hexane into the reaction solution to precipitate, washing the obtained precipitate, drying, adding 150mL of methanol, adding 30mL of ammonia water solution (30%), stirring and dissolving completely, adding the obtained solution into 1L of water to precipitate, washing the obtained precipitate, and drying to obtain the polymer shown in the formula 2; dissolving a polymer shown in a formula 2 in dioxane, adding 10g of 2-diazonium-1-naphthoquinone-5-sulfonyl chloride, stirring and dissolving completely, slowly dripping 4g of triethylamine, stirring and reacting for 1h, adding the obtained reaction solution into 1L of water for precipitation, washing the obtained precipitate, and drying to obtain the polymer shown in the formula 1, namely the photosensitive reinforced resin.
Example 2
A high resolution photoresist composition comprising the following raw materials by weight: 10g of phenolic resin, 20g of photosensitive reinforcing resin, 1g of 2,3, 4' -tetrahydroxybenzophenone-1, 2-diazonaphthoquinone-5-sulfonate, 30g of ethyl lactate and 70g of propylene glycol monomethyl ether;
wherein the phenolic resin is linear phenolic resin, and is synthesized by the following method: adding 40g of m-cresol, 20g of p-phenol and 0.2g of oxalic acid into a reaction kettle, uniformly mixing, adding 10g of formalin solution (36.9 wt%) under the protection of nitrogen, heating to 40 ℃ for reaction for 1h, then continuously heating to 100 ℃ for reaction for 2h, then adding 20g of formalin solution (36.9 wt%) and 0.2g of oxalic acid, continuously reacting for 5h at 100 ℃, and distilling to remove water and unreacted monomers to obtain the linear phenolic resin;
the photosensitive reinforced resin is synthesized by the following method: dissolving 20g of 4-acetoxystyrene, 5g of tert-butyl acrylate and 16g of styrene in 300mL of tetrahydrofuran, adding 0.8g of azodiisobutyronitrile AIBN under the protection of nitrogen, heating to 40 ℃ to react for 0.5h, continuing to heat to reflux for 10h, cooling to room temperature after the reaction is finished, adding a large amount of hexane into the reaction solution to precipitate, washing the obtained precipitate, drying, adding 150mL of methanol, adding 30mL of ammonia water solution (30%) to carry out ammonolysis, stirring and dissolving completely, adding the obtained solution into 1L of water to precipitate, washing the obtained precipitate, and drying to obtain the polymer shown in the formula 2; dissolving a polymer shown in a formula 2 in dioxane, adding 7g of 2-diazonium-1-naphthoquinone-5-sulfonyl chloride, stirring and dissolving completely, slowly dripping 3g of triethylamine, stirring and reacting for 1h, adding the obtained reaction solution into 1L of water for precipitation, washing the obtained precipitate, and drying to obtain the polymer shown in the formula 1, namely the photosensitive reinforced resin.
Example 3
A photosensitive photoresist composition comprising the following raw materials by weight: 30g of phenolic resin, 1g of photosensitive reinforcing resin, 3g of 2,3, 4' -tetrahydroxybenzophenone-1, 2-diazonaphthoquinone-5-sulfonate and 70g of propylene glycol methyl ether acetate;
wherein the phenolic resin is linear phenolic resin, and is synthesized by the following method: adding 30g of m-cresol, 30g of p-phenol and 0.2g of oxalic acid into a reaction kettle, uniformly mixing, adding 10g of formalin solution (36.9 wt%) under the protection of nitrogen, heating to 40 ℃ for reaction for 1h, then continuously heating to 100 ℃ for reaction for 2h, then adding 20g of formalin solution (36.9 wt%) and 0.2g of oxalic acid, continuously reacting for 5h at 100 ℃, and distilling to remove water and unreacted monomers to obtain the linear phenolic resin;
the photosensitive reinforced resin is synthesized by the following method: dissolving 20g of 4-acetoxystyrene, 5g of tert-butyl acrylate and 16g of styrene in 300mL of tetrahydrofuran, adding 0.8g of azodiisobutyronitrile AIBN under the protection of nitrogen, heating to 40 ℃ to react for 0.5h, continuing to heat to reflux for 10h, cooling to room temperature after the reaction is finished, adding a large amount of hexane into the reaction solution to precipitate, washing the obtained precipitate, drying, adding 150mL of methanol, adding 30mL of ammonia water solution (30%) to carry out ammonolysis, stirring and dissolving completely, adding the obtained solution into 1L of water to precipitate, washing the obtained precipitate, and drying to obtain the polymer shown in the formula 2; dissolving a polymer shown in a formula 2 in dioxane, adding 20g of 2-diazonium-1-naphthoquinone-5-sulfonyl chloride, stirring and dissolving completely, slowly dripping 5g of triethylamine, stirring and reacting for 1h, adding the obtained reaction solution into 1L of water for precipitation, washing the obtained precipitate, and drying to obtain the polymer shown in the formula 1, namely the photosensitive reinforced resin.
Example 4
A high resolution photoresist composition comprising the following raw materials by weight: 15g of phenolic resin, 5g of photosensitive reinforcing resin, 2g of 2,3, 4' -tetrahydroxybenzophenone-1, 2-diazonaphthoquinone-5-sulfonate and 85g of propylene glycol methyl ether acetate;
wherein the phenolic resin is linear phenolic resin, and is synthesized by the following method: adding 30g of m-cresol, 30g of p-phenol and 0.2g of oxalic acid into a reaction kettle, uniformly mixing, adding 10g of formalin solution (36.9 wt%) under the protection of nitrogen, heating to 40 ℃ for reaction for 1h, then continuously heating to 100 ℃ for reaction for 2h, then adding 20g of formalin solution (36.9 wt%) and 0.2g of oxalic acid, continuously reacting for 5h at 100 ℃, and distilling to remove water and unreacted monomers to obtain the linear phenolic resin;
the photosensitive reinforced resin is synthesized by the following method: 15g of 4-acetoxystyrene, 8g of tert-butyl acrylate and 18g of styrene are dissolved in 300mL of tetrahydrofuran, 0.8g of azodiisobutyronitrile AIBN is added under the protection of nitrogen, the mixture is heated to 40 ℃ to react for 0.5h, then the mixture is continuously heated to reflux for 10h, the mixture is cooled to room temperature after the reaction is finished, a large amount of hexane is added into the reaction solution to precipitate, the obtained precipitate is washed, dried, 150mL of methanol is added, 30mL of ammonia water solution (30%) is added, stirring and dissolving are completed, the obtained solution is added into 1L of water to precipitate, the obtained precipitate is washed, and the polymer shown in a formula 2 is obtained after drying; dissolving a polymer shown in a formula 2 in dioxane, adding 10g of 2-diazonium-1-naphthoquinone-5-sulfonyl chloride, stirring and dissolving completely, slowly dripping 4g of triethylamine, stirring and reacting for 1h, adding the obtained reaction solution into 1L of water for precipitation, washing the obtained precipitate, and drying to obtain the polymer shown in the formula 1, namely the photosensitive reinforced resin.
Comparative example 1
A photoresist composition comprising the following raw material components by weight: 15g of phenolic resin, 2g of 2,3, 4' -tetrahydroxybenzophenone-1, 2-diazonaphthoquinone-5-sulfonate and 85g of propylene glycol methyl ether acetate;
wherein the phenolic resin is linear phenolic resin, and is synthesized by the following method: adding 30g of m-cresol, 30g of p-phenol and 0.2g of oxalic acid into a reaction kettle, uniformly mixing, adding 10g of formalin solution (36.9 wt%) under the protection of nitrogen, heating to 40 ℃ for reaction for 1h, then continuously heating to 100 ℃ for reaction for 2h, then adding 20g of formalin solution (36.9 wt%) and 0.2g of oxalic acid, continuously reacting for 5h at 100 ℃, and distilling to remove water and unreacted monomers, thus obtaining the linear phenolic resin.
Comparative example 2
A photosensitive photoresist composition comprising the following raw materials by weight: 15g of phenolic resin, 5g of polymer shown in formula 2, 2g of 2,3, 4' -tetrahydroxybenzophenone-1, 2-diazonaphthoquinone-5-sulfonate and 85g of propylene glycol methyl ether acetate;
wherein the phenolic resin is linear phenolic resin, and is synthesized by the following method: adding 30g of m-cresol, 30g of p-phenol and 0.2g of oxalic acid into a reaction kettle, uniformly mixing, adding 10g of formalin solution (36.9 wt%) under the protection of nitrogen, heating to 40 ℃ for reaction for 1h, then continuously heating to 100 ℃ for reaction for 2h, then adding 20g of formalin solution (36.9 wt%) and 0.2g of oxalic acid, continuously reacting for 5h at 100 ℃, and distilling to remove water and unreacted monomers to obtain the linear phenolic resin;
the polymer shown in the formula 2 is synthesized by the following method: 20g of 4-acetoxystyrene, 5g of tert-butyl acrylate and 16g of styrene are dissolved in 300mL of tetrahydrofuran, 0.8g of azodiisobutyronitrile AIBN is added under the protection of nitrogen, the mixture is heated to 40 ℃ to react for 0.5h, then the mixture is continuously heated to reflux for 10h, the mixture is cooled to room temperature after the reaction is finished, a large amount of hexane is added into the reaction solution to precipitate, the obtained precipitate is washed, dried, 150mL of methanol is added, 30mL of ammonia water solution (30%) is added to carry out ammonolysis, after stirring and dissolution are completed, the obtained solution is added into 1L of water to precipitate, the obtained precipitate is washed, and the polymer shown in the formula 2 is obtained after drying.
The photoresist compositions of examples 1 to 4 and comparative examples 1 to 2 were uniformly mixed, and coated on a hexamethyldisilazane HMDS-treated silicon wafer by spin coating, respectively, and then the silicon wafer coated with the photoresist composition was dried in vacuum and baked at 100℃for 90 seconds to obtain a photoresist layer having a thickness of about 1.0. Mu.m.
And (3) respectively exposing the obtained photoresist layers by using a standard L/S=1:1 mask plate and using a light source of I line (with the wavelength of 365 nm), and then respectively developing the exposed photoresist layers by using a tetramethyl ammonium hydroxide solution with the mass fraction of 2.38w% as a developing solution for 60S to obtain photoresist patterns. The resolution of the photoresist pattern was checked using SEM cross-section.
TABLE 1 test results of the photoresist compositions obtained for examples 1-4 and comparative examples 1-2
| Exposure energy (mJ/cm) 2 ) | Resolution (mum) | |
| Example 1 | 55 | 0.35 |
| Example 2 | 70 | 0.45 |
| Example 3 | 60 | 0.45 |
| Example 4 | 55 | 0.35 |
| Comparative example 1 | 80 | 0.8 |
| Comparative example 2 | 105 | 1.5 |
The foregoing is only a preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art, who is within the scope of the present invention, should make equivalent substitutions or modifications according to the technical scheme of the present invention and the inventive concept thereof, and should be covered by the scope of the present invention.
Claims (9)
1. The high-resolution photoresist composition is characterized by comprising the following raw material components in parts by mass: 10-30 parts of phenolic resin, 1-20 parts of photosensitive reinforcing resin, 1-3 parts of photosensitizer and 70-100 parts of organic solvent;
wherein the photosensitive reinforced resin has the chemical structure shown as follows:
x, y and z are mole fractions of corresponding monomers, x is more than or equal to 0.1 and less than or equal to 0.5, y is more than or equal to 0.1 and less than or equal to 0.3, and x+y+z=1;
the photosensitizer is an esterified substance of 2,3, 4' -tetrahydroxybenzophenone and 2,1, 5-diazonaphthoquinone sulfonyl chloride or an esterified substance of 2,2', 4' -tetrahydroxybenzophenone and 2,1, 5-diazonaphthoquinone sulfonyl chloride.
2. The high resolution photoresist composition according to claim 1, wherein the phenolic resin is a phenolic novolac resin.
3. The high resolution resist composition according to claim 2, wherein the novolac resin is produced by polycondensation of a phenolic compound of m-cresol and p-cresol and an aldehyde compound of formaldehyde.
4. The high resolution resist composition according to claim 2, wherein the weight average molecular weight of the novolac resin is 2000 to 30000.
5. The high resolution resist composition according to any one of claims 1 to 4, wherein the photosensitive enhancement resin is produced by an esterification reaction of a polymer represented by formula 2 and 2-diazonium-1-naphthoquinone-5-sulfonyl chloride, wherein the polymer represented by formula 2 has the following chemical structure:
x, y and z are mole fractions of corresponding monomers, x is more than or equal to 0.1 and less than or equal to 0.5, y is more than or equal to 0.1 and less than or equal to 0.3, and x+y+z=1.
6. The high resolution resist composition according to claim 5, wherein the mass ratio of the polymer represented by formula 2 to 2-diazonium-1-naphthoquinone-5-sulfonyl chloride is 2 to 6:1.
7. The high resolution resist composition according to any one of claims 1 to 4, wherein the organic solvent is at least one of ethyl lactate, ethyl acetate, n-butyl acetate, ethylene glycol monomethyl ether, diethylene glycol dimethyl ether, propylene glycol methyl ether acetate, propylene glycol monomethyl ether, or diethylene glycol monomethyl ether.
8. The high resolution photoresist composition according to any one of claims 1 to 4, wherein the photosensitive photoresist composition further comprises at least one of a leveling agent, a colorant, a plasticizer, or a surfactant.
9. Use of a high resolution photoresist composition according to any one of claims 1 to 8 in a lithographic process.
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