CN103324030A - Positive photoresist composition and positive photoresist developing process - Google Patents
Positive photoresist composition and positive photoresist developing process Download PDFInfo
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- CN103324030A CN103324030A CN2013102767386A CN201310276738A CN103324030A CN 103324030 A CN103324030 A CN 103324030A CN 2013102767386 A CN2013102767386 A CN 2013102767386A CN 201310276738 A CN201310276738 A CN 201310276738A CN 103324030 A CN103324030 A CN 103324030A
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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
- G03F7/16—Coating processes; Apparatus therefor
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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
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
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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
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
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Abstract
The invention provides a positive photoresist composition and a positive photoresist developing process. The positive photoresist composition comprises a polymer (A), a photoacid generator (B), a solvent, additives, a photosensitizer (C) and a nitrogen-containing compound (D). Light energy with the wavelength of 365nm can be absorbed by the positive photoresist, and electrons are transferred to the absorption-free photoacid generator at the wavelength of 365nm after excitation, so that the photoacid generator generates an acid. Meanwhile, according to the provided positive photoresist developing process, an image can be formed in a substrate by the photoresist. When the image is formed at the light irradiation of 365nm by virtue of the provided photoresist composition, the light sensitization speed is high, the resolution ratio is high, and the line edge roughness is low.
Description
Technical field
The present invention relates to the photoetching compositions field, especially a kind of chemical amplification type positive photoetching compositions and eurymeric photoresist developing technique.
Background technology
Photoresist refers to irradiation or the radiation by exposure sources such as ultraviolet light, electron beam, excimer laser beam, X ray, ion beams, the etch resistant membraneous material that solubleness is changed.It is mainly used in the photoetching in the figure transfer process from the mask plate to the chip, is the key material in the photoetching process, and it is constantly updated and regenerate with the development of integrated circuit.Photoresist has dividing of positive glue and negative glue.Positive glue is after overexposure, and the part that is subject to illumination becomes and easily dissolves, and through dissolved after developing, only stay the part that is not subjected to illumination and forms figure; And negative glue is on the contrary, after overexposure, the part that is subject to illumination can become not soluble, after developing, stay illumination and partly form the negative glue of figure in the photoetching process application the earliest, its process costs is low, output is high, but because it can expand after absorbing developer solution, cause its resolution (being to form minimum figure in the photoetching process) not as positive glue, therefore for the process technology of sub-micron even smaller szie, mainly use positive glue as photoresist.Positive glue is according to Moore's Law: the integrated level of integrated circuit (IC) was turned in per 18 months.
The semiconductor machining level enters into the nanoscale stage by micron order, submicron order (1.0～0.35 μ m), deep-submicron (0.35 μ m is following), and the requirement of the performances such as photoresist resolution is improved constantly.
The resolution of photoresist can represent with the following formula formula:
R is resolution, and λ is exposure wavelength, k
1Be process constant, NA is the numerical aperture of lens.
Improve the resolution of photoetching, mainly contain following several approach:
1. shortening exposure wavelength;
2. employing resolution enhance technology reduces k as adopting phase-shift mask technology, off-aixs illumination, optical approach effect to proofread and correct
1The factor;
3. increase the numerical aperture of lens, can reduce depth of focus (DOF) but improve the NA value.
Photoetching technique is along with the raising of integrated circuit integrated level, processing live width dwindles, experienced from G line (436nm) photoetching, I line (365nm) photoetching is to deep ultraviolet 248nm photoetching, and the development course of present 193nm photoetching, the photoresist that corresponds to each exposure wavelength is also used and is given birth to.Along with exposure wavelength changes, the composition of photoresist and structure also constantly change, so that the requirement of the full corresponding sufficient integrated technique processing procedure of the combination property of photoresist.
What use in G Lithography, I Lithography is phenolics-diazo naphthoquinone eurymeric photoresist, and its resolution limit can only reach 0.35 μ m.
When the 248nm photoetching, because exposure wavelength dwindles, single photon energy is large, adds the exposure source power limited, and photon numbers descends, and therefore requires corresponding photoresist to have high photosensitivity.Used photoresist is the chemical amplification type photoresist during 248nm photoetching, be characterized in photoresist, having added photo-acid generator in the prescription, under optical radiation, acid agent decomposites acid, when middle baking, acid is catalyzed into film resin and sloughs blocking group (positive glue) as catalyzer, or cross-linking catalyst and film-forming resin generation cross-linking reaction (negative glue); And after sloughing protecting group reaction and cross-linking reaction, acid can be discharged again, can continue Cui Huazuo usefulness, greatly reduces the required energy of exposure, thereby has increased substantially the photosensitivity of photoresist.
Because phenolics has very large non-bleaching absorption under the exposure wavelength of 248nm, make phenolics-diazo naphthoquinone eurymeric photoresist can not continue to be applied to the 248nm photoetching.The 248nm photoresist contains the 4-Vinyl phenol polymkeric substance, acid agent and other components, and the rate of dissolution contrast ratio phenolics of its exposure region and non-exposed area-diazo naphthoquinone eurymeric photoresist is large, has higher resolution potentiality.But the acid agent in the 248nm photoresist can not be that acid is produced in the longer optical excitation of 365nm or wavelength by wavelength, so the 248nm photoresist can not obtain thinner resolution for the photoetching of 365nm wavelength.
Below be several important indicators that are used for weighing the photoresist performance by the image of seeing under the analysis scan Electronic Speculum:
1. effective photosensitivity: show with the minimum exposure scale that obtains figure between 0.5 μ m 1:1 etc.
2. resolution: represent with viewed minimum feature size
3. line edge roughness: according to following criterion electron microscope observation
Good---line edge is straight line, and the edge is narrow
Poor---line edge is not a line, and width is arranged, and the edge is wide.
The patent No. is that 200510128887.3 Chinese invention patent discloses a kind of photoetching compositions, and this photoetching compositions mainly comprises acid reaction component and one or more resins and the photoactive component of interpolation.But the eurymeric photoresist component that the method provides can't obtain higher resolution.
The below illustrates the existing defective of prior art from following Comparative Examples:
Comparative Examples 1
Prepare photoresist by mixing following material:
Poly-(4-Vinyl phenol-co-tert-butoxy ketonic oxygen styrene), 30.4% PGMEA solution, 32.8947 grams
N-hydroxyl-5-norborene-2,3-two carbonyl acid imide trifluoromethane sulfonic acid esters (MDT), 0.26 gram
The PGMEA solution of Tetronic 150R1 surfactant(1%), 8 grams
The only methyl ether acetate of propylene glycol (PGMEA), 31.2153 grams
Said components is mixed, and after the dissolving, the Teflon filtrator filtration by 0.2 μ m namely gets photoresist solution.Coat at the substrate of processing through hexamethyldisilane, the photoetching compositions that said method is prepared is spin-coated on the substrate, will scribble the substrate 90 ℃/60s of hot plate preliminary drying (PAB) of photoresist, and it is 0.75 μ m that adjusting rotary speed makes dry rear thickness.Then by the i line exposing machine irradiation of figure between bar.Exposure gradually changes, the substrate after the exposure with hot plate after 115 ℃/60s of baking, then with substrate with 2.38wt% TMAH spray development 60S.
With the figure that forms after the scanning electron microscopic observation development, and assess its photosensitivity, resolution and line edge roughness.
Comparative Examples 2
Prepare photoresist by mixing following material:
Poly-(hydroxy styrenes-co-acrylic acid spy-butyl ester), 36.7% PGMEA solution, 27.2480 grams
Two-Te-butyl phenyl iodine camphorsulfonic acid ester, 0.6 gram
TBAH, 1% PGMEA solution, 3 grams
Silwet L-7604,1% PGMEA solution, 0.85 gram
The only methyl ether acetate solution of propylene glycol, 50.3380 grams
Said components is mixed, and after the dissolving, the Teflon filtrator filtration by 0.2 μ m namely gets photoresist solution.Coat at the substrate of processing through hexamethyldisilane, the photoetching compositions that said method is prepared is spin-coated on the substrate, will scribble the substrate 100 ℃/60s of hot plate preliminary drying (PAB) of photoresist, and it is 0.75 μ m that adjusting rotary speed makes dry rear thickness.Then by the i line exposing machine irradiation of figure between bar.Exposure gradually changes, the substrate after the exposure with hot plate after 130 ℃/60s of baking, then with substrate with 2.38wt% TMAH spray development 60S.
With the figure that forms after the scanning electron microscopic observation development, and with assessing its photosensitivity, resolution and line edge roughness.
Comparative Examples 3
Prepare photoresist by mixing following material:
The resin of cresols and formaldehyde condensation, Mw=8500,20 grams
Emulsion, the carboxylate of 1,2-naphthoquinones-2-diazonium-5-sulfonic acid chloride and tetrahydroxybenzophenone, esterification degree 75%, 4.3902 gram,
PF6320,1% PGMEA solution, 2.0732 grams,
The only methyl ether acetate solution of propylene glycol, 101.9061 grams
Said components is mixed, and after the dissolving, the Teflon filtrator filtration by 0.2 μ m namely gets photoresist solution.Coat at the substrate of processing through hexamethyldisilane, the photoetching compositions that said method is prepared is spin-coated on the substrate, will scribble the substrate 90 ℃/60s of hot plate preliminary drying (PAB) of photoresist, and it is 0.75 μ m that adjusting rotary speed makes dry rear thickness.Then by i line exposing machine ［ the Nikon i9c NA=0.45 ］ irradiation of figure between bar.Exposure gradually changes, the substrate after the exposure with hot plate after 115 ℃/60s of baking, then with substrate with 2.38wt% TMAH spray development 60S.
With the figure that forms after the scanning electron microscopic observation development, and assess its photosensitivity, resolution and line edge roughness.
Comparative Examples 4
Prepare photoresist by mixing following material:
The resin of cresols and formaldehyde condensation, Mw=8500,20 grams
Emulsion, 1,2-naphthoquinones-2-diazonium-5-sulfonic acid chloride and 2,6-two (2,4-dihydroxy benzyl)-p-Cresol carboxylate, esterification degree 60%, 3.8095 gram,
PF6320,1% PGMEA solution, 2.0238 grams,
The only methyl ether acetate solution of propylene glycol, 99.47986 grams
Said components is mixed, and after the dissolving, the Teflon filtrator filtration by 0.2 μ m namely gets photoresist solution.Coat at the substrate of processing through hexamethyldisilane, the photoetching compositions that said method is prepared is spin-coated on the substrate, will scribble the substrate 90 ℃/60s of hot plate preliminary drying (PAB) of photoresist, and it is 0.75 μ m that adjusting rotary speed makes dry rear thickness.Then by the i line exposing machine irradiation of figure between bar.Exposure gradually changes, the substrate after the exposure with hot plate after 115 ℃/60s of baking, then with substrate with 2.38wt% TMAH spray development 60S.
The figure that forms after developing with scanning electron microscopic observation, and assess its photosensitivity, resolution and line edge roughness with following methods.
Each Comparative Examples lithographic results under 365nm is summarized in table 1
Table 1
As can be known, Comparative Examples 1, Comparative Examples 2 do not obtain image owing to not adding i-line photosensitizer behind the i-Lithography from table.Comparative Examples 3, Comparative Examples 4 are traditional phenolics-diazo naphthoquinone system, and wherein the minimum feature that can differentiate of Comparative Examples 3 is 0.6 μ m, can not tell the lines of 0.5 μ m, and line edge roughness is poor; The minimum feature that Comparative Examples 4 can be differentiated is 0.45 μ m, and the required exposure amount is up to 130 mJ/cm2, and film speed is slow, and line edge roughness is poor.
On the whole, existing photoresist technology can't under the 365nm illumination so that phenolics-obtain high-resolution image after the exposure of diazo naphthoquinone eurymeric photoresist.In view of above problem, need especially the light exposure of a kind of energy by the 365nm wavelength, and have than existing phenolics-diazo naphthoquinone eurymeric photoresist and have more high-resolution photoresist.
Summary of the invention
The present invention is namely improved for defects, a kind of eurymeric photoetching compositions is provided, in prescription, adds photosensitizer, but the energy that this photosensitizer absorbing wavelength is the light of 365nm, then energy is transferred to the photo-acid generator without absorption at 365nm, makes the photo-acid generator sensitization produce acid.Compare with phenolics-diazo naphthoquinone eurymeric photoresist, photoetching compositions of the present invention has the advantages such as film speed is fast, resolution is high, line edge roughness is little when the light irradiation imaging of 365nm.
For achieving the above object, the invention provides a kind of novel eurymeric photoetching compositions, it comprises polymkeric substance (A), photo-acid generator (B), photosensitizer (C) and nitrogen-containing compound (D) and solvent and adjuvant.
Aforesaid eurymeric photoetching compositions, preferably, polymkeric substance (A) is a kind ofly can increase by the effect of acid alkali-soluble polymkeric substance.
Preferably, polymkeric substance (A) is for meeting the polymkeric substance (A) of general formula (1) in above-mentioned arbitrary scheme.
Preferably, R1 is the acid-unstable group that easily breaks away under the effect of acid in the described general formula (1) in above-mentioned arbitrary scheme.
In above-mentioned arbitrary scheme preferably, R1 in the general formula (1) can be one or more in the groups such as oxinane-2-base, 2-methyl oxinane-2-base, tetrahydrofuran-2-base, 2-methyltetrahydrofuran-2-base, 1-methoxy-propyl, 1-methoxyl-1-Methylethyl, 1-ethoxycarbonyl propyl, 1-ethoxy-1-Methylethyl, 1-methoxy ethyl, 1-ethoxyethyl group, uncle 1--butoxyethyl group, 1-isobutoxy ethyl, more preferably, R1 is tert-butoxycarbonyl.
Preferably, the described ratio that meets the middle x1:y1 of polymkeric substance (A) of general formula (1) is 10～90mol%:90～10mol% in above-mentioned any scheme, more preferably, and 50～85mol%:50%～15%mol.
Preferably, the described ratio that meets the middle x1:y1 of polymkeric substance (A) of general formula (1) is 20～80mol%:80～20mol% in above-mentioned any scheme.
Preferably, the described ratio that meets the middle x1:y1 of polymkeric substance (A) of general formula (1) is 30～70mol%:70～30mol% in above-mentioned any scheme.
Preferably, the described ratio that meets the middle x1:y1 of polymkeric substance (A) of general formula (1) is 40～60mol%:60～40mol% in above-mentioned any scheme.
Preferably, the described molecular weight that meets the polymkeric substance (A) of general formula (1) is 3000～30000 in above-mentioned any scheme, more preferably 5000～15000.
Preferably, the described molecular weight that meets the polymkeric substance (A) of general formula (1) is 4000～20000 in above-mentioned any scheme.
Preferably, the described molecular weight that meets the polymkeric substance (A) of general formula (1) is 5000～20000 in above-mentioned any scheme.
Preferably, the described molecular weight that meets the polymkeric substance (A) of general formula (1) is 6000～15000 in above-mentioned any scheme.
Preferably, the described molecular weight that meets the polymkeric substance (A) of general formula (1) is 7000～10000 in above-mentioned any scheme.
Preferably, the described molecular weight distribution that meets the polymkeric substance (A) of general formula (1) is less than or equal to 3 in above-mentioned any scheme, and more preferably, molecular weight distribution is less than or equal to 2.
Preferably, described polymkeric substance (A) is for meeting the polymkeric substance (A) of general formula (2) in above-mentioned any scheme.
Preferably, the Q2 in the general formula (2) of described polymkeric substance (A) can be hydrogen atom, methyl or trifluoromethyl, more preferably hydrogen atom in above-mentioned any scheme.
Preferably, the R2 in described polymkeric substance (A) general formula (2) is illustrated in the acid-unstable group that easily breaks away under the effect of acid in above-mentioned any scheme.
In above-mentioned any scheme preferably, Q2 in described polymkeric substance (A) general formula (2) can be oxinane-2-base, 2-methyl oxinane-2-base, tetrahydrofuran-2-base, 2-methyltetrahydrofuran-2-base, the 1-methoxy-propyl, 1-methoxyl-1-Methylethyl, the 1-ethoxycarbonyl propyl, 1-ethoxy-1-Methylethyl, the 1-methoxy ethyl, the 1-ethoxyethyl group, uncle 1--butoxyethyl group, 1-isobutoxy ethyl, methylcyclohexyl, methyl adamantane, the ethyl adamantyl, in the methyl isobornyl etc. one or more, the more preferably tert-butyl group.
Preferably, the ratio of the X2:Y2 in described polymkeric substance (A) general formula (2) is 10～90mol%:90～10mol% in above-mentioned any scheme, more preferably, and 50～85mol%:50%～15%mol.
Preferably, the ratio of the X2:Y2 in described polymkeric substance (A) general formula (2) is 20～80mol%:80～20mol% in above-mentioned any scheme.
In above-mentioned any scheme, preferably, the ratio of the X2:Y2 in described polymkeric substance (A) general formula (2) is 30～70mol%:70～30mol%.
Preferably, the ratio of the X2:Y2 in described polymkeric substance (A) general formula (2) is 40～60mol%:60～40mol% in above-mentioned any scheme.
Preferably, the described weight-average molecular weight MW that meets the polymkeric substance (A) of general formula (2) is 8000～50000 in above-mentioned any scheme, more preferably, and 15000～30000.
Preferably, the described weight-average molecular weight MW that meets the polymkeric substance (A) of general formula (2) is 9000～40000 in above-mentioned any scheme.
Preferably, the described weight-average molecular weight MW that meets the polymkeric substance (A) of general formula (2) is 10000～30000 in above-mentioned any scheme.
Preferably, the described weight-average molecular weight MW that meets the polymkeric substance (A) of general formula (2) is 20000～50000 in above-mentioned any scheme.
Preferably, the described molecular weight distribution that meets the polymkeric substance (A) of general formula (2) is less than or equal to 3 in above-mentioned any scheme, is more preferably to be less than or equal to 2.
In above-mentioned any scheme preferably, the described polymkeric substance (A) that meets general formula (2) also can contain other polymerized unit, such as styrene, a-methyl styrene, vinyl cyanide, other can participate in the monomer of polymerization one or more (methyl) methyl acrylates etc.
Preferably, photo-acid generator (B) component that eurymeric photoetching compositions of the present invention comprises has the acid imide sulphonic acid ester structure represented such as general formula (3) in above-mentioned any scheme.
Preferably, having such as R3 in the described photo-acid generator of general formula (3) (B) is in camphor, diamantane, alkyl (C1-12 alkyl), the perfluoroalkyl (perfluor C1-12 alkyl) one or more in above-mentioned any scheme.
Preferably, described photo-acid generator (B) is one or more in perfluoro octyl sulfonic acid ester, the perfluor nonyl sulphonic acid ester etc. in above-mentioned any scheme.More preferably, the acid imide sulphonic acid ester is N-[(perfluoro capryl sulfonamido) oxygen]-5-norborene-2, the 3-dimethyl imide.
Preferably, described photo-acid generator (B) is a kind of salt, comprises iodine compound and sulfonium compound in above-mentioned any scheme, and they can cooperate with various negative ion, form sulfonate.
Preferably, described photo-acid generator (B) is to have formula (4), structure salt compounded of iodine shown in the formula (5) in above-mentioned any scheme.
This salt compounded of iodine photo-acid generator can be that 96118111.2 European patent is prepared according to application number.This patent has described the synthetic method of above-mentioned patent in detail.
In above-mentioned any scheme preferably, described photo-acid generator (B) can be for above-mentioned formula (4), the camphorsulfonic acid ester negative ion that cooperates in the formula (5) changes the negative ion in the formula (3) into, and wherein R3 is diamantane, alkyl (C1-12 alkyl), perfluoroalkyl (perfluor C1-12 alkyl).Preferably, perfluoro octyl sulfonic acid ester, perfluor nonyl sulphonic acid ester etc.
Preferably, described photo-acid generator (B) is the sulfosalt with formula (6) structure in above-mentioned any scheme.
Preferably, the described middle R6 of photo-acid generator (B) with formula (6) structure is one or more in hydrogen atom, C1-12 alkyl, the C1-12 alkoxy in above-mentioned any scheme.
In above-mentioned any scheme, preferably, the described middle m of photo-acid generator (B) with formula (6) structure is the integer of 0-5, and m is preferably integer 0,1,2.
Preferably, the described middle Q6 of photo-acid generator (B) with formula (6) structure is one or more in camphor, diamantane, alkyl (C1-12 alkyl), the perfluoroalkyl (perfluor C1-12 alkyl) in above-mentioned any scheme.More preferably, perfluoro octyl sulfonic acid ester, perfluor nonyl sulphonic acid ester etc.
In above-mentioned any scheme preferably, described photo-acid generator (B) can also be in oxime sulfonate class acid agent, diazomethane class acid agent and other the known acid agent that uses one or more in chemical amplification photo etching glue composition in the past, be not particularly limited.
Preferably, described photo-acid generator (B) is with respect to polymkeric substance (A) component of 100 weight portions in above-mentioned any scheme, and its use amount is 0.5～30 weight portion, preferably, and 1～10 weight portion.If consumption is less than 0.5 weight portion, the formation of pattern can not be carried out satisfactorily, if consumption surpasses 30 weight portions, it is difficult to dissolve in the solvent of photoetching compositions, is difficult to obtain uniform photoresist solution, and the storage stability of photoresist descends.
Preferably, described photo-acid generator (B) is with respect to polymkeric substance (A) component of 100 weight portions in above-mentioned any scheme, and its use amount is 2～20 weight portions.
Preferably, described photo-acid generator (B) is with respect to polymkeric substance (A) component of 100 weight portions in above-mentioned any scheme, and its use amount is 3～10 weight portions.
Preferably, described photo-acid generator (B) is with respect to polymkeric substance (A) component of 100 weight portions in above-mentioned any scheme, and its use amount is 4～8 weight portions.
Preferably, described photosensitizer (C) is a kind of photosensitizer that contains anthryl in above-mentioned any scheme.
In above-mentioned any scheme preferably, the photosensitizer that contain anthryl of described photosensitizer (C) for having absorption characteristic at 365nm, it can absorbing wavelength be the luminous energy of 365nm, is stimulated, electronics is transferred to the photo-acid generator without absorption at 365nm, makes the photo-acid generator sensitization produce acid.
Preferably, described photosensitizer (C) is Isosorbide-5-Nitrae-dimethoxy anthracene, 9 in above-mentioned any scheme, 10-dimethoxy anthracene, 9, one or more in the photoactive substances such as 10-dimethylanthracene, 9-methylphenoxy anthracene.More preferably, photosensitizer (C) is 9-methanol-based anthracene.
Preferably, the addition of described photosensitizer (C) is 0.5%～10.0% of polymkeric substance in the photoetching compositions (A) in above-mentioned any scheme, preferred 1.5%-5.0%.
Preferably, the addition of described photosensitizer (C) is 2%～8% of polymkeric substance in the photoetching compositions (A) in above-mentioned any scheme.
In above-mentioned any scheme preferably, described photosensitizer (C) be incorporated as 3%～7% of polymkeric substance in the photoetching compositions (A).
The chemically amplified positive photoresist, in the placement during the PEB after the exposure, the acid meeting on photoresist film top layer is by the neutralization of the amine pollutant in the environment, causes when developing the top layer insoluble, has shelf-stability problem after the exposure; The excess diffusion of acid can cause the precision of picture size that problem is arranged during PEB in addition.For improving the rear shelf-stability of exposure and preventing sour excess diffusion, the preferred alkalescence that adds contains the N compound as sour quencher in chemically amplified positive photoresist of the present invention.
In above-mentioned any scheme, preferably, add sour quencher in the described eurymeric photoetching compositions.
Preferably, described sour quencher is that alkalescence contains the N compound in above-mentioned any scheme.
Preferably, described nitrogen-containing compound (D) is a kind of organic basic nitrogen-containing compound in above-mentioned any scheme.
In above-mentioned any scheme preferably, described nitrogen-containing compound (D) is lower aliphatic amine, such as in the materials such as diethylamine, triethylamine, two-n-propylamine, Tri-n-Propylamine, tri-n-octyl amine, dioctyl methyl amine one or more, more preferably, alkyl amine.
Preferably, described nitrogen-containing compound (D) is the lower aliphatic hydramine in above-mentioned any scheme, such as in the materials such as diethanolamine, triethanolamine, triisopropanolamine one or more, more preferably, tertiary alkanolamines.
In above-mentioned any scheme preferably, described nitrogen-containing compound (D) is the hydroxide alkyl amine, such as in the materials such as lactate of hydroxide tetraethyl amine, tetrabutylphosphoniuhydroxide hydroxide amine, tetrabutylphosphoniuhydroxide hydroxide amine one or more, more preferably, tetrabutylphosphoniuhydroxide hydroxide amine and lactate thereof.
In above-mentioned any scheme preferably, described nitrogen-containing compound (D) is uncle's alkoxyalkyl amine, such as three-(2-methoxymethoxy ethyl) amine, three-2-(2-methoxyl (ethoxy) ethylamine), in the material such as three-(2-(2-methoxy ethoxy) methoxy ethoxy amine one or more, more preferably, three-2-(2-methoxyl (ethoxy) ethylamine).
Preferably, described nitrogen-containing compound (D) is cyclic amine in above-mentioned any scheme, such as in the materials such as pyridine, picoline, ethylpyridine Isosorbide-5-Nitrae-diazabicylo ［ 2,2,2 ］ octane one or more.
Preferably, described nitrogen-containing compound (D) is polymeric amine in above-mentioned any scheme, such as poly-ethylpyridine, the Tetronic series polymer amine of BASF.
Preferably, described nitrogen-containing compound (D) is with respect to (A) component of 100 weight portions in above-mentioned any scheme, and its use amount is 0.01～5.0 weight portion.
Preferably, solvent of the present invention can be can dissolve component (A) in the photoetching compositions of the present invention, component (B), component (C), component (D) to produce any solvent of homogeneous solution in above-mentioned any scheme.
Preferably, solvent of the present invention can be as one or more solvents in the known solvent of the solvent of traditional chemical amplified positive photoresist in above-mentioned any scheme.
Preferably, solvent of the present invention is ketone in above-mentioned any scheme, such as in acetone, methyl ethyl ketone, cyclohexanone, methyl isoamyl ketone, the 2-HEPTANONE etc. one or more.
In above-mentioned any scheme preferably, solvent of the present invention is polyvalent alcohol and derivant thereof, such as 1,2-ethylidene glycol, diglycol, propylene glycol, ethylene glycol monoethyl ether, propylene glycol monomethyl ether, diethylene glycol monoethyl ether, ethylene glycol monoethyl ether acetate, one or more in the propylene glycol methyl ether acetate etc.
Preferably, solvent of the present invention is cyclic ethers class material in above-mentioned any scheme, such as in tetrahydrofuran, the dioxan etc. one or more.
In above-mentioned any scheme preferably, solvent of the present invention is ester type compound, such as in methyl lactate, ethyl lactate, methyl acetate, ethyl acetate, butyl acetate, methyl pyruvate, ethyl pyruvate, methoxy methyl propionate, ethoxyl ethyl propionate, the gamma-butyrolacton etc. one or more.
Preferably, solvent of the present invention is aromatic hydrocarbons in above-mentioned any scheme, as toluene and dimethylbenzene etc. one or more.
Preferably, the use amount of solvent of the present invention is 10～90 % by weight of photoetching compositions total amount in above-mentioned any scheme.More preferably, determine the actual amount of solvent according to required photoresist thickness.
Preferably, the use amount of solvent of the present invention is 20～80 % by weight of photoetching compositions total amount in above-mentioned any scheme.
Preferably, the use amount of solvent of the present invention is 30～70 % by weight of photoetching compositions total amount in above-mentioned any scheme.
Preferably, the use amount of solvent of the present invention is 40～60 % by weight of photoetching compositions total amount in above-mentioned any scheme.
In above-mentioned any scheme, preferably, in the photoetching compositions of the present invention, can further add the adjuvant with mixed nature as required.Such as adding for improvement photoresist additive resin, the surfactant that is used for improving coating character, dissolution inhibitor, plastifier, stabilizing agent, colorant, antihalation agent etc.
Another object of the present invention is, a kind of eurymeric photoresist developing technique is provided, and it may further comprise the steps:
(1) preparation of eurymeric photoetching compositions and substrate pre-service;
(2) the eurymeric photoetching compositions that obtains in the step (1) is covered be stated from the substrate;
(3) substrate that obtains in the step (2) is carried out the front pre-service of illumination;
(4) substrate that obtains in the step (3) is carried out illumination and aftertreatment;
(5) substrate that obtains in the step (4) is carried out finishing.
Preferably, eurymeric photoetching compositions of the present invention is to form pattern under wavelength is the light irradiation of 365nm.
Preferably, the substrate pre-service is for being coated with antireflecting coating described in the step (1) in above-mentioned any scheme.
Preferably, photoetching compositions can be applied on the substrate by spin coating, dip coated, roller coat or other any coating technique in the step (2) in above-mentioned any scheme.When using the rotary coating mode, according to employed apparatus for coating, can by regulating the solid content of photoresist, make it reach desired thickness.The viscosity of photoetching compositions, spin speed and and the coating time all be adjustable to the requirement of satisfying rotary coating.
Preferably, described substrate can be silicon chip, be coated with SiO in above-mentioned any scheme
2The silicon chip of coating also can be aluminium-chromium oxide, gallium arsenide, pottery, quartz, copper, glass substrate etc.
In above-mentioned any scheme preferably, pre-service was toasted 60 seconds～120 seconds under 70 ℃～150 ℃ for the substrate that will obtain in the step (2) before the illumination described in the step (3), desolventizing makes glued membrane dry, until photoresist coating adheres to the surface of substrate securely.
Preferably, pre-service was toasted 70～100 seconds under 80～100 degrees centigrade for the substrate that will obtain in the step (2) before the illumination described in the step (3) in above-mentioned any scheme.
Preferably, pre-service was toasted 80～110 seconds under 80～150 degrees centigrade for the substrate that will obtain in the step (2) before the illumination described in the step (3) in above-mentioned any scheme.
Preferably, the exposure during illumination described in the step (4) should be enough to activate the Photoactive compounds in the photoresist film in above-mentioned any scheme, forms patterned image in photoresist coating.
Preferably, the aftertreatment described in the step (4) was toasted 30～120 seconds under 70 ℃～150 ℃ temperature for the substrate after will exposing in above-mentioned any scheme.
Preferably, the aftertreatment described in the step (4) is that the substrate after will exposing toasted 40～100 seconds under 80～100 degrees centigrade in above-mentioned any scheme.
Preferably, the aftertreatment described in the step (4) was developed 30～120 seconds by gunite, paddling process, infusion process etc. for developing with alkaline-based developer after the baking in above-mentioned any scheme.
Preferably, the aftertreatment described in the step (4) was developed 50～100 seconds by gunite, paddling process, infusion process etc. for developing with alkaline-based developer after the baking in above-mentioned any scheme.
Preferably, the aftertreatment described in the step (4) is used rinsed with deionized water for after developing, and forms the resist pattern of regulation in above-mentioned any scheme.
Preferably, described alkaline-based developer can working concentration be one or more in the alkaline aqueous solutions such as the alkali metal hydroxide, ammoniacal liquor, alkyl amine, alkanol amine, heterocyclic amine, tetraalkylammonium hydroxide class of 1～5 % by weight in above-mentioned any scheme.Preferably, tetra-alkyl ammonium hydroxide solution, more preferably, the tetramethyl ammonium hydroxide solution of 0.26N.
In above-mentioned any scheme, preferably, add the materials such as surfactant in the described alkaline-based developer.
Preferably, the described finishing of step (5) can be to select suitable etching agent to carry out chemical etching to the substrate that obtains in the step (4) in above-mentioned any scheme.
Preferably, described etching agent can be the gas etching agent in above-mentioned any scheme.
Preferably, described gas etching agent can be the halogen plasmas etchant in above-mentioned any scheme.
Preferably, described halogen plasmas etchant can be Cl in above-mentioned any scheme
2
, CF
4, CHF
3In one or more.
In above-mentioned any scheme, preferably, after the described finishing of step (5) can be the substrate etching, use known degumming process that photoresist is removed from substrate.
The invention provides a kind of photoetching compositions, in prescription, add photosensitizer, but this photosensitizer absorbing wavelength is the energy of the light of 365nm, then energy is transferred at 365nm without the photo-acid generator that absorbs, make the photo-acid generator sensitization produce acid, have the advantages such as film speed is fast, resolution is high, line edge roughness is little during the imaging of light irradiation.
The invention provides a kind of photoetching compositions, the combination that can fill a prescription according to different technical requirements, manufacture craft is simple, and equipment requirement is lower.
Eurymeric photoetching compositions provided by the present invention and be coated with the combination in any that the technical scheme of echoing development step comprises each part mentioned above, the simple change of each part mentioned above assembly or combination still are protection scope of the present invention.
Embodiment
In order to understand better the present invention, below in conjunction with specific embodiment the present invention is made detailed description.But, obviously can carry out different modification and remodeling and not exceed the wider spirit and scope of the present invention that appended claim limits the present invention.Therefore, following examples have exemplary and hard-core implication.
Embodiment 1:
Prepare photoresist by mixing following material:
Poly-(4-Vinyl phenol-co-tert-butoxy ketonic oxygen styrene), 30% PGMEA solution, 32.8947 grams
N-hydroxyl-5-norborene-2,3-two carbonyl acid imide trifluoromethane sulfonic acid esters, 0.26 gram
9-methanol-based anthracene, 0.18 gram
The PGMEA solution of Tetronic 150R1 surfactant(1%), 8 grams
The only methyl ether acetate of propylene glycol (PGMEA), 31.2153 grams
Said components is mixed, and after the dissolving, the Teflon filtrator filtration by 0.2 μ m namely gets photoresist solution.Coat at the substrate of processing through hexamethyldisilane, the photoetching compositions that said method is prepared is spin-coated on the substrate, will scribble the substrate 90 ℃/60s of hot plate preliminary drying (PAB) of photoresist, and it is 0.75 μ m that adjusting rotary speed makes dry rear thickness.Then expose with i line exposing machine by figure between bar.Exposure gradually changes, the substrate after the exposure with hot plate after 115 ℃/60s of baking, then with substrate with 2.38wt% TMAH spray development 60S.
With the figure that forms after the scanning electron microscopic observation development, and assess its photosensitivity, resolution and line edge roughness.
Embodiment 2:
Prepare photoresist by mixing following material:
Poly-(hydroxy styrenes-co-acrylic acid spy-butyl ester), 35% PGMEA solution, 27.2480 grams
Two-Te-butyl phenyl iodine camphorsulfonic acid ester, 0.6 gram
9-methanol-based anthracene, 0.6 gram
TBAH, 1% PGMEA solution, 3 grams
Silwet L-7604,1% PGMEA solution, 0.85 gram
The only methyl ether acetate solution of propylene glycol, 50.3380 grams
Said components is mixed, and after the dissolving, the Teflon filtrator filtration by 0.2 μ m namely gets photoresist solution.Coat at the substrate of processing through hexamethyldisilane, the photoetching compositions that said method is prepared is spin-coated on the substrate, will scribble the substrate 100 ℃/60s of hot plate preliminary drying (PAB) of photoresist, and it is 0.75 μ m that adjusting rotary speed makes dry rear thickness.Then by i line exposing machine ［ the Nikon i9c NA=0.45 ］ irradiation of figure between bar.Exposure gradually changes, the substrate after the exposure with hot plate after 130 ℃/60s of baking, then with substrate with 2.38wt% TMAH spray development 60S.
With the figure that forms after the scanning electron microscopic observation development, and assess its photosensitivity and resolution and line edge roughness.
These two embodiment lithographic results under 365nm is summarized in table 2
Table 2
As can be known, photoresist not only has fast film speed and excellent resolution among the embodiment 1-2, and line edge roughness is little from table.
Embodiment 3:
Prepare photoresist by mixing following material:
Poly-(4-Vinyl phenol-co-tert-butoxycarbonyl oxygen styrene), 30% PGMEA solution, 33 grams
N-[(perfluoro capryl sulfonamido) oxygen]-5-norborene-2,3-dimethyl imide, 0.3 gram
9-methanol-based anthracene, 0.2 gram
The PGMEA solution of Tetronic 150R1 surfactant(1%), 8 grams
The only methyl ether acetate of propylene glycol (PGMEA), 31 grams
Said components is mixed, and after the dissolving, the Teflon filtrator filtration by 0.2 μ m namely gets photoresist solution.Coat at the substrate of processing through hexamethyldisilane, the photoetching compositions that said method is prepared is spin-coated on the substrate, will scribble the substrate 90 ℃/60s of hot plate preliminary drying (PAB) of photoresist, and it is 0.75 μ m that adjusting rotary speed makes dry rear thickness.Then expose with i line exposing machine by figure between bar.Exposure gradually changes, the substrate after the exposure with hot plate after 115 ℃/60s of baking, then with substrate with 2.38wt% TMAH spray development 60S.
Embodiment 4:
Prepare photoresist by mixing following material:
Poly-(hydroxy styrenes-co-acrylic acid spy-butyl ester), 35% PGMEA solution, 27.2480 grams
Perfluor nonyl sulphonic acid ester, 0.6 gram
9,10-dimethoxy anthracene, 0.6 gram
TBAH, 1% PGMEA solution, 3 grams
Silwet L-7604,1% PGMEA solution, 0.85 gram
The only methyl ether acetate solution of propylene glycol, 50.3380 grams
Said components is mixed, and after the dissolving, the Teflon filtrator filtration by 0.2 μ m namely gets photoresist solution.Coat at the substrate of processing through hexamethyldisilane, the photoetching compositions that said method is prepared is spin-coated on the substrate, will scribble the substrate 100 ℃/60s of hot plate preliminary drying (PAB) of photoresist, and it is 0.75 μ m that adjusting rotary speed makes dry rear thickness.Then by i line exposing machine ［ the Nikon i9c NA=0.45 ］ irradiation of figure between bar.Exposure gradually changes, the substrate after the exposure with hot plate after 130 ℃/60s of baking, then with substrate with 2.38wt% TMAH spray development 60S.
Embodiment 5:
Prepare photoresist by mixing following material:
Poly-(hydroxy styrenes-co-acrylic acid spy-butyl ester), 35% PGMEA solution, 27.2480 grams
The perfluoro octyl sulfonic acid ester, 0.6 gram
9,10-dimethoxy anthracene, 0.6 gram
TBAH, 1% PGMEA solution, 3 grams
Silwet L-7604,1% PGMEA solution, 0.85 gram
The only methyl ether acetate solution of propylene glycol, 50.3380 grams
Said components is mixed, and after the dissolving, the Teflon filtrator filtration by 0.2 μ m namely gets photoresist solution.Coat at the substrate of processing through hexamethyldisilane, the photoetching compositions that said method is prepared is spin-coated on the substrate, will scribble the substrate 100 ℃/60s of hot plate preliminary drying (PAB) of photoresist, and it is 0.75 μ m that adjusting rotary speed makes dry rear thickness.Then by i line exposing machine ［ the Nikon i9c NA=0.45 ］ irradiation of figure between bar.Exposure gradually changes, the substrate after the exposure with hot plate after 130 ℃/60s of baking, then with substrate with 2.38wt% TMAH spray development 80S.
Claims (10)
1. eurymeric photoetching compositions, comprise polymkeric substance (A), photo-acid generator (B), solvent and adjuvant, it is characterized in that: also comprise photosensitizer (C) and nitrogen-containing compound (D), so that described eurymeric photoetching compositions can absorbing wavelength be the luminous energy of 365nm, after excited by illumination, electronics is transferred to the photo-acid generator without absorption at 365nm, makes photo-acid generator produce acid.
2. eurymeric photoetching compositions as claimed in claim 1 is characterized in that: described polymkeric substance (A) is a kind ofly can increase by the effect of acid alkali-soluble polymkeric substance.
3. eurymeric photoetching compositions as claimed in claim 1 is characterized in that: described polymkeric substance (A) is for meeting the polymkeric substance of general formula (1).
4. eurymeric photoetching compositions as claimed in claim 3 is characterized in that: the acid-unstable group of R1 for easily breaking away under the effect of acid in the described general formula (1).
5. eurymeric photoetching compositions as claimed in claim 3, it is characterized in that: the R1 in the described general formula (1) is one or more in tert-butoxycarbonyl, oxinane-2-base, 2-methyl oxinane-2-base, tetrahydrofuran-2-base, 2-methyltetrahydrofuran-2-base, 1-methoxy-propyl, 1-methoxyl-1-Methylethyl, 1-ethoxycarbonyl propyl, 1-ethoxy-1-Methylethyl, 1-methoxy ethyl, 1-ethoxyethyl group, uncle 1--butoxyethyl group, the 1-isobutoxy ethyl.
6. eurymeric photoetching compositions as claimed in claim 3 is characterized in that: the ratio of x1:y1 is 10～90mol%:90～10mol% in the described general formula (1).
7. eurymeric photoetching compositions as claimed in claim 3 is characterized in that: the ratio of x1:y1 is 50～85mol%:50%～15%mol in the described general formula (1).
8. eurymeric photoetching compositions as claimed in claim 3, it is characterized in that: the described molecular weight that meets the polymkeric substance (A) of general formula (1) is 3000～30000.
9. eurymeric photoetching compositions as claimed in claim 8 is characterized in that: the described molecular weight 5000～15000 that meets the polymkeric substance (A) of general formula (1).
10. eurymeric photoresist developing technique comprises following step:
(1) preparation eurymeric photoetching compositions, and pre-service substrate;
(2) the eurymeric photoetching compositions that obtains in the step (1) is covered be stated from the substrate;
(3) substrate that obtains in the step (2) is carried out the front pre-service of illumination;
(4) substrate that obtains in the step (3) is carried out illumination and aftertreatment;
It is characterized in that: During Illumination is finished under the light irradiation of 365nm described in the step (4), and the substrate that obtains in step (4) is carried out finishing.
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| PCT/CN2013/081975 WO2015000214A1 (en) | 2013-07-03 | 2013-08-21 | Positive photoresist composition and positive photoresist developing process |
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| CN108864341A (en) * | 2017-05-12 | 2018-11-23 | 湖北固润科技股份有限公司 | Poly(4-hydroxystyrene) based epoxy resin, its synthesis and application |
| CN113419404A (en) * | 2021-06-29 | 2021-09-21 | 北京科华微电子材料有限公司 | Photoresist composition |
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| TWI742165B (en) * | 2017-09-27 | 2021-10-11 | 奇美實業股份有限公司 | Chemically-amplified type positive photo sensitive resin composition, resist pattern and method of forming thereof, and electronic device |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101305321A (en) * | 2005-11-10 | 2008-11-12 | Az电子材料美国公司 | Developable undercoating composition for thick photoresist layers |
| CN102317258A (en) * | 2009-02-20 | 2012-01-11 | 三亚普罗股份有限公司 | Sulfonium salt, photo-acid generator, and photosensitive resin composition |
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|---|---|---|---|---|
| CN101305321A (en) * | 2005-11-10 | 2008-11-12 | Az电子材料美国公司 | Developable undercoating composition for thick photoresist layers |
| CN102317258A (en) * | 2009-02-20 | 2012-01-11 | 三亚普罗股份有限公司 | Sulfonium salt, photo-acid generator, and photosensitive resin composition |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108864341A (en) * | 2017-05-12 | 2018-11-23 | 湖北固润科技股份有限公司 | Poly(4-hydroxystyrene) based epoxy resin, its synthesis and application |
| CN113419404A (en) * | 2021-06-29 | 2021-09-21 | 北京科华微电子材料有限公司 | Photoresist composition |
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