CN113214429B - ArF photoresist film-forming resin, preparation method thereof and photoresist composition - Google Patents
ArF photoresist film-forming resin, preparation method thereof and photoresist composition Download PDFInfo
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- CN113214429B CN113214429B CN202110466795.5A CN202110466795A CN113214429B CN 113214429 B CN113214429 B CN 113214429B CN 202110466795 A CN202110466795 A CN 202110466795A CN 113214429 B CN113214429 B CN 113214429B
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- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1811—C10or C11-(Meth)acrylate, e.g. isodecyl (meth)acrylate, isobornyl (meth)acrylate or 2-naphthyl (meth)acrylate
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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
Abstract
The invention discloses an ArF photoresist film-forming resin, a preparation method thereof and a photoresist composition, which comprise a random copolymer structure shown as a formula I: wherein n, m, x, y and z are molar ratios of the monomers, n is more than 0 and less than or equal to 0.3, m is more than 0 and less than or equal to 0.5, x is more than 0 and less than or equal to 0.2, y is more than 0 and less than or equal to 0.8, z is more than 0 and less than or equal to 0.1, and n + m + x + y + z is 1; r1、R2、R3、R4And R5Is H, CH3Or CH2CH3. A photoresist composition comprises 5-30% of the film-forming resin and the balance of an organic solvent. The invention introduces the photoacid generator and the acid diffusion inhibitor into the film-forming resin simultaneously, can well control the photoacid generator and the acid diffusion inhibitor to be uniformly distributed, thereby improving the sensitivity (less than or equal to 42 mJ/cm) of the photoresist2) And the resolution (less than or equal to 90 nm). In addition, the film forming ability and adhesion of the photoresist can be improved due to the introduction of each monomer.
Description
Technical Field
The invention belongs to the technical field of semiconductor photoresist microelectronic chemistry, and relates to a resin for a photoresist, a preparation method thereof and a photoresist composition.
Background
Photoresist, also known as photoresist, refers to a resist film material whose solubility changes under the irradiation or radiation of ultraviolet light, electron beam, ion beam, X-ray, etc. Photoresists play a particular role in the integrated circuit chip fabrication process, and the higher the integration level of an integrated circuit, the higher the requirements on the photoresist.
According to the rayleigh equation, the feature size achievable in the lithography process satisfies the relationship CD ═ k λ/NA, where k is a system parameter, depending on the quality of the imaging optics, the projection mode of the mask and the mask pattern itself; lambda is the wavelength of the light source, and the manufacturing process of the photoetching process is fundamentally determined; and NA is the numerical aperture of the lens. For a long time, the development of photolithography processes has mainly relied on the continuous reduction of the wavelength of the light source, from 365nm (I-line) to 248nm (KrF), 193nm (ArF), 13nm (EUV). In order to improve the sensitivity of the photoresist, the current KrF, ArF and EUV photoresists are mainly made of chemically amplified photosensitive resin. At present, commercial photoresist materials independently developed in China mainly comprise phenolic resin, poly-p-hydroxystyrene and the like, and are mainly used for photoetching processes of G-lines (436nm) and I-lines (365 nm). However, the wavelength of a light source used by the current international mainstream photoetching process is 193nm, and the photoresist material has the defects of low photosensitivity, low resolution of the obtained pattern, poor etching resistance, poor contrast of the obtained pattern and the like when being used for the 193nm process.
Therefore, how to design and develop a matching material (film-forming resin) meeting the requirements of a photoresist formula is the key point of the current photoresist product formula development. In addition, the screening and sizing of photoresist formulations is a more worldwide problem. How to make the whole photoresist formulation have good resolution and line roughness is always the direction of important research in the industry.
Disclosure of Invention
In order to overcome the defects in the prior art, the invention provides a film-forming resin for photoresist, a photoresist composition and a preparation method. And then the photoresist suitable for 193nm far ultraviolet exposure wavelength is prepared.
The technical scheme of the invention is as follows:
an ArF photoresist film-forming resin comprising a random copolymer structure as shown below:
wherein n, m, x, y and z are the molar ratio of the monomers, n is more than 0 and less than or equal to 0.3, and 0＜m≤0.5，0＜x≤0.2，0＜y≤0.8，0＜z≤0.1，n+m+x+y+z＝1；R1、R2、R3、R4And R5Is H, CH3Or CH2CH3。
Preferably, the film-forming resin is prepared by copolymerizing a monomer I, a monomer II, a monomer III, a monomer IV and a monomer V, wherein the monomer I, the monomer II, the monomer III, the monomer IV and the monomer V are respectively:
wherein R is1、R2、R3、R4And R5Is H, CH3Or CH2CH3。
Preferably, the copolymerization comprises the steps of:
(1) under inert atmosphere, adding the monomer and the initiator into a solvent, uniformly stirring, and reacting;
(2) after the reaction is finished, settling in methanol or ether, filtering, drying the filter cake, dissolving the filter cake in a solvent, precipitating again in methanol or ether, filtering, and drying the filter cake to obtain the film-forming resin.
Preferably, the weight ratio of the monomers I, II, III, IV and V in the step (1) is as follows: (10-30): (1-20): (1-20): (30-80): (0.001-10); the mass volume ratio of the total monomer amount to the solvent is 100: (20-2000) g/mL.
Preferably, the initiator in the step (1) is benzoyl peroxide, benzoic acid hydrogen peroxide, tert-butoxy hydrogen peroxide, azobisisobutyronitrile, azobisisoheptonitrile; the solvent in the steps (1) and (2) is one or more than two of dichloromethane, chloroform, tetrahydrofuran, toluene, acetone, dioxane, dichloroethane, trichloroethane, xylene and methyl ethyl ketone.
Preferably, the reaction temperature in the step (2) is 40-80 ℃, and the reaction time is 1-12 hours.
Preferably, the reaction temperature in the step (2) is 50-60 ℃, and the reaction time is 2-6 hours.
The photoresist composition comprises the film-forming resin and an organic solvent, wherein the film-forming resin accounts for 5-30% by mass, and the balance is the organic solvent.
Preferably, the organic solvent in the composition is one or more of anisole, propylene glycol monoalkyl ether, toluene, chlorobenzene, benzene, carbon tetrachloride, chloroform, dichloromethane, hexane, butyl acetate, neopentyl acetate, ethyl lactate, propylene glycol alkyl ether acetate, ethyl acetate, butyl acetate, dimethylformamide, cyclopentanone, cyclohexanone, acetone, methyl ethyl ketone, and methyl isobutyl ketone.
Preferably, the film-forming resin and the organic solvent are mixed according to the formula proportion and are vibrated for 12 to 96 hours in the dark to be fully dissolved; the photoresist solution was then filtered through a 0.5 micron filter or less to obtain a photoresist composition.
Compared with the prior art, the invention has the following beneficial effects:
the photoacid generator and the acid diffusion inhibitor are simultaneously introduced into the film-forming resin, so that the photoacid generator and the acid diffusion inhibitor can be well controlled to be uniformly distributed in a film of the film-forming resin, and the photoacid generator and the acid diffusion inhibitor in the film-forming resin can normally play a role, so that the photoacid diffusion range can be well reduced, and the sensitivity (less than or equal to 42 mJ/cm) of the photoresist is improved, thereby2) And the resolution (less than or equal to 90 nm). In addition, the film forming ability and adhesion of the photoresist can be improved due to the introduction of each monomer.
Drawings
FIG. 1 is a photo-lithographic pattern of a photoresist of example 5 of the present invention.
Detailed Description
The present invention will be described in further detail with reference to specific examples, but the embodiments of the present invention are not limited thereto, and may be carried out with reference to conventional techniques for process parameters not particularly noted.
Example 1
Under a nitrogen-filled condition, 10g of cholic acid methacrylate (monomer 1, formula II) and 20g of butyl methacrylate were mixedLactone (monomer 2, formula III), 10g of sulfonium methacrylate (monomer 3, formula IV), 60g of adamantyl methacrylate (monomer 4, formula V), 1g of dimethylethylamine methacrylate (monomer 5, formula VI) and 600mL of dioxane were charged into a 1000mL reaction flask, 0.2g of Azobisisobutyronitrile (AIBN) was added thereto, sufficiently stirred, heated to 60 ℃ and held for 3 hours. Then cooled to room temperature, precipitated in ether, filtered and the filter cake dried. Dissolving the filter cake in tetrahydrofuran, precipitating in methanol, filtering, drying the filter cake, and repeating the process twice to obtain the film-forming resin. The weight average molecular weight M of the film-forming resin was measured by GPCwAt 35000, the molecular weight distribution PDI was 1.45.
Example 2
30g of acrylic cholate (monomer 1, formula II), 10g of acrylic butyrolactone (monomer 2, formula III), 5g of acrylic sulfonium salt ester (monomer 3, formula IV), 55g of adamantyl acrylate (monomer 4, formula V), 5g of dimethylethylaminoacrylate (monomer 5, formula VI) and 600mL of dioxane were charged into a 1000mL reaction flask, followed by addition of 0.2g of Azobisisobutyronitrile (AIBN), sufficiently stirred, heated to 60 ℃ and held for 5 hours under a nitrogen atmosphere. Then cooled to room temperature, precipitated in ether, filtered and the filter cake dried. Dissolving the filter cake in tetrahydrofuran, precipitating in methanol, filtering, drying the filter cake, and repeating the process twice to obtain the film-forming resin. The weight average molecular weight M of the film-forming resin was measured by GPCw38000 and a molecular weight distribution PDI of 1.36.
Example 3
10g of cholate methacrylate (monomer 1, formula II), 10g of butyrolactone acrylate (monomer 2, formula III), 10g of sulfonium methacrylate (monomer 3, formula IV), 70g of adamantyl methacrylate (monomer 4, formula V), 0.5g of dimethylethylaminomethacrylate (monomer 5, formula VI), and 600mL of methylethylketone were charged into a 1000mL reaction flask, followed by addition of 0.3g of Azobisisobutyronitrile (AIBN), stirring thoroughly, heating to 50 ℃ and holding for 8 hours.Then cooled to room temperature, precipitated in ether, filtered and the filter cake dried. Dissolving the filter cake in tetrahydrofuran, precipitating in methanol, filtering, drying the filter cake, and repeating the process twice to obtain the film-forming resin. The weight average molecular weight M of the film-forming resin was measured by GPCwAt 25000, the molecular weight distribution PDI was 1.27.
Example 4
A positive chemical amplification type photoresist comprises the following components in percentage by weight:
the resin was the film-forming resin of example 1; the solvent is propylene glycol monomethyl ether acetate.
The specific formula is prepared as follows:
30g of the film-forming resin and 70g of propylene glycol monomethyl ether acetate were put into a 200mL light-shielding glass bottle. The mixture was fully dissolved by shaking at room temperature for 12 hours. The photoresist solution was filtered through 0.5 micron, 0.2 micron and 0.02 micron filters in sequence. Finally, a photolithography experiment was performed.
Example 5
A positive chemical amplification type photoresist comprises the following components in percentage by weight:
the resin was the film-forming resin of example 2; the solvent is neopentyl acetate.
The specific formula is prepared as follows:
10g of the film-forming resin and 90g of neopentyl acetate were put into a 200mL light-shielding glass bottle. The mixture was fully dissolved by shaking at room temperature for 24 hours. The photoresist solution was filtered through 0.5 micron, 0.22 micron and 0.02 micron filters in sequence. Finally, a photolithography experiment was performed.
Example 6
A positive chemical amplification type photoresist comprises the following components in percentage by weight:
the resin was the film-forming resin of example 3; the solvent is propylene glycol monomethyl ether acetate.
The specific formula is prepared as follows:
20g of the film-forming resin and 80g of propylene glycol monomethyl ether acetate were put into a 200mL light-shielding glass bottle. The mixture was fully dissolved by shaking at room temperature for 12 hours. The photoresist solution was filtered through 0.5 micron, 0.2 micron and 0.02 micron filters in sequence. Finally, a photolithography experiment was performed.
Example 7
The photoresists prepared in examples 4 to 6 were used for the preparation of photolithographic films by the following specific operations: spin-coating the prepared photoresist on a 12-inch silicon plate, and baking at 90 ℃/120s to obtain a photoresist layer with the thickness of 75-80 nm. After obtaining the photoresist layer, using 193nm (ArF) photoetching machine to perform L/S pattern exposure, wherein the exposure energy range is 20-45mJ/cm2. After the completion of exposure, the resist film was exposed on a hot stage at 120 ℃/60s and then baked, and the exposed resist film layer was developed for 30s with an alkaline aqueous developer (2.38 mass% tetramethylammonium hydroxide aqueous solution (TMAH aqueous solution)), and then rinsed with ultrapure water to obtain a resist pattern. As can be seen from FIG. 1, the edges of the individual lines of the photoresist are uniform, and no sticking or glue pouring occurs.
TABLE 1 Effect of the application of the photoresists obtained in examples 4 to 6
| Product(s) | Resolution (nm) | Sensitivity (mJ/cm)2) | Adhesion property | Film forming property |
| Example 4 | 75 | 30 | Good effect | Good effect |
| Example 5 | 90 | 42 | Good effect | In general |
| Example 6 | 86 | 34 | Good effect | Good effect |
Adhesion test: the characterization mode accepted in the industry is to prepare the resin into photoresist, and the prepared pattern is observed by a scanning electron microscope, the phenomena of stripping and glue falling are not seen, and the adhesion is proved to be good, if the phenomena of glue falling, stripping, line deformation and the like occur, the resin is proved to be invalid.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
Claims (10)
1. An ArF photoresist film-forming resin comprising a random copolymer structure as shown below:
wherein n, m, x, y and z are molar ratios of the monomers, n is more than 0 and less than or equal to 0.3, m is more than 0 and less than or equal to 0.5, x is more than 0 and less than or equal to 0.2, y is more than 0 and less than or equal to 0.8, z is more than 0 and less than or equal to 0.1, and n + m + x + y + z is 1; r1、R2、R3、R4And R5Is H, CH3Or CH2CH3。
2. The method for preparing the film-forming resin according to claim 1, wherein the film-forming resin is prepared by copolymerizing a monomer I, a monomer II, a monomer III, a monomer IV and a monomer V, wherein the monomer I, the monomer II, the monomer III, the monomer IV and the monomer V are respectively:
wherein R is1、R2、R3、R4And R5Is H, CH3Or CH2CH3。
3. The method according to claim 2, wherein the copolymerization comprises the steps of:
(1) under inert atmosphere, adding the monomer and the initiator into a solvent, uniformly stirring, and reacting;
(2) after the reaction is finished, settling in methanol or ether, filtering, drying the filter cake, dissolving the filter cake in a solvent, precipitating again in methanol or ether, filtering, and drying the filter cake to obtain the film-forming resin.
4. The preparation method according to claim 3, wherein the monomers I, II, III, IV and V in step (1) are prepared from the following monomers in parts by weight: (10-30): (1-20): (1-20): (30-80): (0.001-10); the mass volume ratio of the total monomer amount to the solvent is 100: (20-2000) g/mL.
5. The method according to claim 3 or 4, wherein the initiator in the step (1) is benzoyl peroxide, benzoic acid hydroperoxide, t-butyl hydroperoxide, azobisisobutyronitrile, azobisisoheptonitrile; the solvent in the steps (1) and (2) is one or more than two of dichloromethane, chloroform, tetrahydrofuran, toluene, acetone, dioxane, dichloroethane, trichloroethane, xylene and methyl ethyl ketone.
6. The method according to claim 5, wherein the reaction temperature in the step (1) is 40 to 80 ℃ and the reaction time is 1 to 12 hours.
7. The method according to claim 6, wherein the reaction temperature in the step (1) is 50 to 60 ℃ and the reaction time is 2 to 6 hours.
8. A photoresist composition, which is characterized by comprising the film-forming resin according to claim 1 and an organic solvent, wherein the film-forming resin accounts for 5-30% by mass, and the balance is the organic solvent.
9. The photoresist composition of claim 8, wherein the organic solvent in the composition is one or more of anisole, propylene glycol monoalkyl ether, toluene, chlorobenzene, benzene, carbon tetrachloride, chloroform, methylene chloride, hexane, butyl acetate, neopentyl acetate, ethyl lactate, propylene glycol alkyl ether acetate, ethyl acetate, butyl acetate, dimethylformamide, cyclopentanone, cyclohexanone, acetone, methyl ethyl ketone, methyl isobutyl ketone.
10. The process for preparing the photoresist composition according to claim 8 or 9, wherein the film-forming resin and the organic solvent are mixed according to the formula ratio, and are vibrated in dark for 12 to 96 hours to be fully dissolved; the photoresist solution was then filtered through a 0.5 micron filter or less to obtain a photoresist composition.
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