CN104529795B - A kind of compound for photoetching compositions - Google Patents
A kind of compound for photoetching compositions Download PDFInfo
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- CN104529795B CN104529795B CN201410855760.0A CN201410855760A CN104529795B CN 104529795 B CN104529795 B CN 104529795B CN 201410855760 A CN201410855760 A CN 201410855760A CN 104529795 B CN104529795 B CN 104529795B
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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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- 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
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Abstract
The present invention relates to a kind of compound for photoetching compositions, it is applicable to using the excimer laser lithography of ArF, KrF etc., EUV lithography and EB photoetching etc., and it shows outstanding various photoresist material abilities such as susceptibility, sharpness etc., and obtain line edge roughness and the pattern contour of special improvement.
Description
Technical field
The present invention relates to compound shown in a kind of formula (I), for the manufacture of the photoetching compositions of computer chip and unicircuit.
Background technology
Photoetching compositions for the manufacture of the microlithographic technique of miniaturized electronic components, such as, for the manufacture of computer chip and unicircuit.Usually, in these techniques, first the film coating of photoetching compositions is put on base material, then evaporate the solvent in photoetching compositions and coating is fixed in substrate, making to be coated in the exposure that suprabasil photoresist material carries out imaging mode finally by radiation.
Radiation causes the chemical transformation of coated surface, and wherein the optical, electrical son bundle of visible ray, ultraviolet (UV) and X-radiation can be normally used emission types in microlithography technology now.After exposure, coated substrate is used developing solution process, to dissolve and to remove the radiant exposure of photoresist material or unexposed region.The miniaturization tendency of semiconductor element, result in the use at the more and more newer photoresist material that Low emissivity wavelength place can be photosensitive, and result also in the use of complicated multilevel system, to overcome the difficulty relevant with this miniaturization.
In theory, the shorter sharpness that can make of exposure wavelength is higher.The wavelength of exposure light source progressively shortens to the g line with 436nm wavelength, the i line with 365nm wavelength, has the KrF excimer laser of 248nm wavelength, has the ArF excimer laser of 193nm wavelength.Wavelength is the F of 157nm
2excimer laser is expected to become exposure light source of future generation.With regard to the exposure light source of suceeding generation, the EUV (extreme ultraviolet) that wavelength is 13nm or shorter is proposed.The novel photoresist material that the trend of semiconductor device miniature is responsive under having caused being used in more and more lower radiation wavelength, but also cause the difficulty that the complicated multilevel hierarchy of use is brought to overcome this microminiaturization.
Photoresist material resolving power is defined as photoetching compositions can be transferred to minimal characteristic substrate after exposure and development from photomask with hi-vision edge sharpness.Manufacture in Application Areas at many frontier nature edges at present, need the photoresist material resolving power being less than about half micron.When photoresist material size has been brought down below 150nm, the roughness of photoetching agent pattern has become a crucial problem.The edge roughness of so-called line edge roughness is observed to the roughness along photoresist line for line and blank pattern usually, and is observed to sidewall roughness for contact hole.Edge roughness may produce detrimental action to the lithography characteristic of photoresist material, is especially reducing critical size amplitude and the line edge roughness of photoresist material is transferred to types of flexure face.Therefore, the minimized photoresist material of edge roughness is made to be high expectations.
Generally speaking, the image that high-resolution extreme ultraviolet (UV) photoresist material can obtain for making lower than 1/4th microns of geometrical dimensions forms pattern.So far, have three kinds of main extreme ultraviolet exposure techniques that marked improvement is provided in microminiaturized, and these technology are used in 248nm, send the laser apparatus of radiation under 193nm and 157nm.Photoresist material for extreme ultraviolet usually comprises and has acid labile group and can de-protected polymkeric substance in the presence of acid, the acidic photoactive component when absorb light, and solvent.
Photoetching compositions for the semiconductor micro fabrication adopting photoetching process comprises: resin, it has the structural unit derived from the compound with acid-unstable group, and to be insoluble to or to be insoluble in alkali aqueous solution but to become in the alkaline soluble aqueous solution by the effect of acid; Acidogenic agent, it comprises by the acidic compound of radiation; And basic cpd.United States Patent (USP) 5,914,219 disclose a kind of photoetching compositions, and it comprises: resin, it has the structural unit derived from the compound with acid-unstable group, and to be insoluble to or to be insoluble in alkali aqueous solution but to become in the alkaline soluble aqueous solution by the effect of acid; Acidogenic agent, it comprises by the acidic compound of radiation; And as the TBAH of basic cpd.In the photoetching compositions usually known, there is the problem that the generation line edge roughness because of sustained wave etc. occurs, namely the slickness of pattern sidewalls declines, and the homogeneity of result live width is deteriorated.
Summary of the invention
Technical problem to be solved by this invention is to provide compound shown in a kind of formula (I), it is for showing outstanding various photoresist material abilities such as susceptibility, sharpness etc. during photoetching compositions, and obtains line edge roughness and the pattern contour of special improvement.
According to an embodiment of the invention, the invention provides compound shown in a kind of formula for photoetching compositions (I):
Wherein R
1-R
12represent halogen, C independently
1-C
20direct-connected or branched-chain alkyl, C
3-C
30cyclic hydrocarbon group or C
2-C
20thiazolinyl, or R
1-R
11in two or more combine formation nitrogen heterocyclic ring; Y is counter anion.
In one embodiment of the invention, R
1-R
12represent C independently
1-C
6straight or branched alkyl, and wherein R
4-R
12one is had at least to be fluorine.
In one embodiment of the invention, R
1-R
12represent C independently
1-C
8straight or branched alkyl, and wherein R
4-R
12one is had at least to be halogen or CF
3.
According to an embodiment of the invention, the example of halogen atom comprises fluorine atom, chlorine atom, bromine atoms and atomic iodine, preferred fluorine atom.
In one embodiment of the invention, R
1-R
12represent butyl, methyl and octyl group independently, and wherein R
4-R
12one is had at least to be halogen or CF
3.
In one embodiment of the invention, the compound that formula (I) represents is with following formula (A) compound:
Wherein R
1-R
3for C
1-C
8alkyl, Y is counter anion.
In one embodiment of the invention, R
1-R
3for C
1-C
8alkyl, Y is counter anion.
Shown in formula (I), compound can such as by making tetra-alkyl ammonium hydroxide such as Tetramethylammonium hydroxide and corresponding hydroxy alkyl carboxylic acid react generation.Photoetching compositions of the present invention is capable of being combined uses compound shown in two or more formulas (I).
According to an embodiment of the invention, the invention provides a kind of method forming pattern at substrate surface, comprising:
(1) on substrate, apply the step of the photoetching compositions containing compound of the present invention,
(2) by carrying out the dry step forming photoresist film,
(3) described photoresist film is made to be exposed to the step of radiation,
(4) step of the described photoresist film through exposure is cured, and
(5) alkaline developer is utilized to make the described photoresist film development through curing form the step of photoetching agent pattern thus.
Comprise in photoetching compositions containing compound formula (I) Suo Shi:
(1) one or more resins,
(2) compound that represents of formula (I), in the solid ingredient gross weight of photoetching compositions for benchmark, the content of formula (I) compound is generally 0.01-10 % by weight, preferred 0.05-8 % by weight, more preferably 0.1-5 % by weight;
(3) solvent;
Described solid ingredient to refer in photoetching compositions component in addition to the solvents.
According to an embodiment of the invention, the resin in photoetching compositions of the present invention can be:
1) resin be suitable at the chemical-amplification positive resist of 248nm imaging can be provided to comprise: containing the polymkeric substance of vinylphenol with (methyl) acrylate unit, such as tert-butyl acrylate, Tert-butyl Methacrylate, vinylformic acid methyl adamantane base ester, methyl methacrylate adamantyl ester and other can carry out acyclic alkyl and the alicyclic ring acrylate of photic sour induced reaction, as U.S. patent 6,042,997 and 5,492, polymkeric substance in 793, is incorporated herein and for referencial use.
2) can provide and be suitable for comprising lower than the resin of 200nm wavelength as the chemical-amplification positive resist of 193nm imaging: i) containing the polymkeric substance of the polymerized unit of the optional norbornylene replaced, as being disclosed in U.S. patent 5,843, the polymkeric substance of 624; Ii) containing the polymkeric substance of (methyl) acrylate unit, as tert-butyl acrylate, methacrylic acid tertiary butyl ester, vinylformic acid methyl adamantane base ester, methyl methacrylate adamantyl ester and other acyclic alkyl and alicyclic radical (methyl) acrylate; These polymkeric substance have been described in U.S. patent 6,057, in 083.
According to an embodiment of the invention, the unit of following general formula (I), (II) and (III) is comprised for the resin in the photoresist material lower than 200nm such as 193nm imaging:
In formula: R
1(C
1-C
3) alkyl; R
2(C
1-C
3) alkylidene group; L
1it is lactone group; N is 1 or 2.
Applicable monomer for the formation of resin is purchased and/or can synthesizes with currently known methods.Those skilled in the art be easy to utilize currently known methods and other be purchased starting raw material and utilize monomer synthesize resin.In the mixture composition used in the present invention of two or more resins.Resin is present in anti-corrosion agent composition with the amount of abundance to obtain the uniform coating of desired thickness.
Normally, in the solid ingredient gross weight of photoetching compositions for benchmark, be present in the amount of the resin in composition from 70 to 95wt%.In the solid ingredient gross weight of photoetching compositions for benchmark, photoetching compositions of the present invention generally include based on solid ingredient summation 80 % by weight or more resin.
Resin is preferably insoluble to or is insoluble in alkali aqueous solution and become in the alkaline soluble aqueous solution by the effect of acid.The weight-average molecular weight of resin is preferably 500-100000, more preferably 1000-30000.Weight-average molecular weight gel available permeation chromatography measures.
When photoetching compositions of the present invention comprises solvent, the ratio (resin/solvent) of resin and solvent is generally 1/1 to 1/1000, and preferably 1/50 to 1/500.
According to an embodiment of the invention, R in the compound that represents of formula (I)
1-R
12represent C independently
1-C
8direct-connected or branched-chain alkyl, and wherein R
4-R
12one is had at least to be halogen or CF
3.
According to an embodiment of the invention, R in the compound that represents of formula (I)
1-R
12represent C independently
1-C
6alkyl, and wherein R
4-R
12one is had at least to be fluorine.
According to an embodiment of the invention, C involved in the compound that formula (I) represents
1-C
20the preferred C of alkyl
1-C
15straight chained alkyl and C
3-C
15branched-chain alkyl, more preferably C
1-C
10straight chained alkyl and C
3-C
10branched-chain alkyl, its specific examples comprises methyl, ethyl, propyl group, sec.-propyl, butyl, isobutyl-, sec-butyl, the tertiary butyl, amyl group, isopentyl, tert-pentyl, neo-pentyl, 1, 2-dimethyl propyl, 1-ethyl propyl, hexyl, heptyl, octyl group, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, 1-methylethyl, 1-methyl-propyl, 2-methyl-propyl, 1-methyl butyl, 2-methyl butyl, 3-methyl butyl, 1-ethyl-butyl, 2-ethyl-butyl, 1-methyl amyl, 2-methyl amyl, 3-methyl amyl and 4-methyl amyl.
According to an embodiment of the invention, C involved in the compound that formula (I) represents
3-C
30the preferred tool 3-20 carbon atom of saturated cyclic alkyl, more preferably 3-15 carbon atom, especially the preferably saturated cyclic alkyl of 3-8 carbon atom, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, suberyl and ring octyl group.
According to an embodiment of the invention, C involved in the compound that formula (I) represents
2-C
20thiazolinyl preferably has 2-5 carbon atom, more particularly by combination alkyl above-mentioned and vinyl (-CH=CH
2) thiazolinyl that formed.
Described C
1-C
20alkyl, C
3-C
30saturated cyclic alkyl and C
2-C
20thiazolinyl can have one or more substituting group.Substituent example comprises halogen atom, haloalkyl as C
1-C
20haloalkyl, alkyl are as C
1-C
20alkyl, alkoxyl group, hydroxy alkoxy base, alkyloxy-alkoxy, alkoxyl group carbonyl oxygen base, Alkoxycarbonylalkoxy, alkoxy carbonyl, aryl, heteroaryl and aralkyl.The example of halogen atom comprises fluorine atom, chlorine atom, bromine atoms and atomic iodine, preferred fluorine atom.As haloalkyl, preferred fluoro-alkyl.The example of alkyl comprises and described identical those above.The example of aryl comprises phenyl, xenyl, fluorenyl, naphthyl, anthryl and phenanthryl.The example of heteroaryl comprise one of them or more an above-mentioned aryl that the carbon atom forming aromatic ring is substituted as Sauerstoffatom, sulphur atom and nitrogen-atoms by heteroatoms.The example of aralkyl comprises benzyl, styroyl, 1-menaphthyl, 2-menaphthyl, 1-naphthalene ethyl and 2-naphthalene ethyl.As aralkyl, preferably by C that aryl replaces
1-C
4alkyl, more preferably by C that aryl replaces
1-C
2alkyl, especially preferably by methyl that aryl replaces.Described aryl, heteroaryl and aralkyl can have one or more substituting group as C
1-C
10alkyl, haloalkyl are (as C
1-C
8haloalkyl, preferred C
1-C
4haloalkyl), alkoxyl group, hydroxyl and halogen atom.
According to an embodiment of the invention, also solvent is comprised in photoetching compositions of the present invention.Amount usually account for the total amount of photoetching compositions of the present invention 90 % by weight of solvent or more, preferably 92 % by weight or more, more preferably 94 % by weight or more.Wrap solvent-laden photoetching compositions can be preferred for producing thin layer photoetching agent pattern.
The solvent that may be used for photoetching compositions of the present invention can be the Conventional solvents in photoresist material field, comprises such as: ketone, such as acetone, methyl ethyl ketone, methyl iso-butyl ketone (MIBK), pimelinketone, isophorone, methyl isoamyl ketone, 2-heptanone 4-hydroxyl, and 4-methyl-2 pentanone, C
1to C
10fatty alcohol, such as methyl alcohol, ethanol, and propyl alcohol, alcohol containing aromatic base, such as phenylcarbinol, cyclic carbonate, such as ethylene carbonate and Texacar PC, aliphatic series or aromatic hydrocarbons (such as, hexane, toluene, dimethylbenzene, etc.), cyclic ethers, such as two
alkane and tetrahydrofuran (THF), ethylene glycol, propylene glycol, hexylene glycol, ethylene glycol monoalkyl ether, such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol alkylether acetates, such as methylcellosolve acetate and ethyl cellosolve acetate, glycol dialkyl ether, such as glycol dimethyl ether, ethylene glycol diethyl ether, Ethylene Glycol Methyl ether, monoalkyl ethers of diethylene glycol, such as diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, and diglyme, propylene-glycol monoalky lether, such as propylene glycol monomethyl ether, propylene-glycol ethyl ether, propylene glycol propyl ether, and propandiol butyl ether, propylene glycol alkyl ether acetic acid ester, such as propylene glycol methyl ether acetate, propylene-glycol ethyl ether acetic ester, propylene glycol propyl ether acetic ester, and propandiol butyl ether acetic ester, propylene glycol alkyl ether propionic ester, such as propylene glycol monomethyl ether acetate, propylene-glycol ethyl ether propionic ester, propylene glycol propyl ether propionic ester, and propandiol butyl ether propionic ester, 2-methoxy ethyl ether (diglyme), there is the solvent of ether and hydroxylic moiety, such as methoxybutanol, ethoxybutanol, methoxypropanol, and oxyethyl group propyl alcohol, ester, such as methyl acetate, ethyl acetate, propyl acetate, and butylacetate Pyruvic Acid Methyl ester, Pyruvic Acid Ethyl ester, 2 hydroxy propanoic acid ethyl ester, 2-hydroxyl 2 Methylpropionic acid methyl esters, 2-hydroxyl 2 Methylpropionic acid ethyl ester, methylhydroxy acetic ester, ethyl glycollic acid ester, butylhydroxy acetic ester, methyl lactate, ethyl lactate, propyl lactate, n-Butyl lactate, 3-hydroxy methyl propionate, 3-hydroxypropionate, 3-hydroxy-propionic acid propyl ester, 3-hydroxy-propionic acid butyl ester, methyl 2-hydroxyl 3 Methylbutanoic acid, methyl methoxy yl acetate, ethyl methoxyacetic acid ester, propylmethoxy acetic ester, butylmethoxy acetic ester, methylethoxy yl acetate, ethyl ethoxyacetic acid ester, propyl group ethoxyacetic acid ester, butyl ethoxyacetic acid ester, methyl-prop ethoxyacetic acid ester, ethylpropoxy acetic ester, propyl group propoxy-acetic ester, butyl propoxy-acetic ester, methylbutoxy group acetic ester, ethyl-butoxy acetic ester, propylbutoxy acetic ester, butyl butoxy acetic acid ester, 2-methoxy methyl propionate, 2-methoxypropionate, 2-methoxy propyl propyl propionate, 2-methoxy propyl acid butyl ester, 2-ethoxypropanoate, 2-ethoxyl ethyl propionate, 2-ethoxy-c propyl propionate, 2-ethoxy-c acid butyl ester, 2-butoxy methyl propionate, 2-butoxy ethyl propionate, 2-butoxy propyl propionate, 2-butoxy butyl propionate, 3-methoxy methyl propionate, 3-methoxypropionate, 3-methoxy propyl propyl propionate, 3-methoxy propyl acid butyl ester, 3-ethoxypropanoate, 3-ethoxyl ethyl propionate, 3-ethoxy-c propyl propionate, 3-ethoxy-c acid butyl ester, 3-propoxy-methyl propionate, 3-propoxy-ethyl propionate, 3-propoxy-propyl propionate, 3-propoxy-butyl propionate, 3-butoxy methyl propionate, 3-butoxy ethyl propionate, 3-butoxy propyl propionate, with 3-butoxy butyl propionate, oxygen base isobutyrate, such as, methyl-2-hydroxy-isobutyric acid esters, α-methoxy isobutyl acid methyl esters, methoxy isobutyl acetoacetic ester, α-oxyethyl group methyl isobutyrate, α-oxyethyl group ethyl isobutyrate, 'beta '-methoxy methyl isobutyrate, 'beta '-methoxy ethyl isobutyrate, β-oxyethyl group methyl isobutyrate, β-oxyethyl group ethyl isobutyrate, β-isopropoxy methyl isobutyrate, β-isopropoxy ethyl isobutyrate, β-isopropoxy isopropyl isobutyrate, β-isopropoxy butyl isobutyrate, Beta-Butoxy methyl isobutyrate, Beta-Butoxy ethyl isobutyrate, Beta-Butoxy butyl isobutyrate, Alpha-hydroxy isobutyric acid methyl esters, ethyl alpha-hydroxyisobutyrate, Alpha-hydroxy isobutyric acid isopropyl ester, with Alpha-hydroxy isobutyric acid butyl ester, there is the solvent of ether and hydroxylic moiety, such as methoxybutanol, ethoxybutanol, methoxypropanol, and oxyethyl group propyl alcohol, and other solvent, such as dibasic ester, and gamma-butyrolactone, ether ketone derivative, such as Pyranton methyl ether, acetol derivative, such as hydroxyacetone or Pyranton, amide derivatives, such as N,N-DIMETHYLACETAMIDE or dimethyl formamide, methyl-phenoxide, and its mixture.
According to an embodiment of the invention, described photoetching compositions, in described photoetching compositions, the composition of solvent is preferably: (1) glycol dimethyl ether 15 weight part, (2) ethyl acetate 40 weight part and (3) gamma-butyrolactone 5 weight part.
According to an embodiment of the invention, other additive various is also comprised, such as tinting material, the dyestuff not playing photo-actinic action, anti-striped reagent, softening agent, tackifier, dissolution inhibitor, coating additive, photospeed enhancers, other light acid producing agent in photoetching compositions of the present invention.
The tensio-active agent (such as fluorinated surfactant) improving film uniformity, the sensitizing agent that energy can be passed to various exposure wavelength from specified range wavelength can also be comprised in photoetching compositions of the present invention.
Photoetching compositions of the present invention can contain one or more of basic cpd, and to prevent from forming T-shaped top (t-tops) or bridge type on photoresist material imaging surface, the content of basic cpd accounts for the 0.01-1 % by weight of solid ingredient usually.The preferred alkaline organic compounds containing nitrogen of described basic cpd, the example comprises amine compound as aliphatic amine and aromatic amine and ammonium salt.The example of aliphatic amine comprises primary amine, secondary amine and tertiary amine.
According to an embodiment of the invention, described photoetching compositions contains the basic cpd being selected from pyridine, amine, ammonium hydroxide, trioctylamine, diethanolamine and tetrabutylammonium hydroxide, in the total weight of solids of photoetching compositions for benchmark, the content of basic cpd accounts for the 0.01-1 % by weight of solid ingredient usually.
By at resin from it or photoetching compositions of the present invention applies radiation as optical, electrical son bundle etc., decompositions produces sour by resin.In photoetching compositions of the present invention, resin not only plays the effect of resin Composition but also plays the effect of acidogenic agent.
Although resin plays the effect of acidogenic agent in photoetching compositions of the present invention described above, photoetching compositions of the present invention also can contain other acidogenic agents.Acidogenic agent can be selected from by the acidic various compound with acidogenic agent described in x radiation x self or the photoetching compositions containing described acidogenic agent.The example of acidogenic agent comprises salt, haloalkyl triaizine compounds, two sulphones, the diazomethane compound with alkylsulfonyl, sulfonate compound and has the imide compound of sulfonyloxy.
The example of salt comprises that one or more nitro is included in salt in negatively charged ion, one or more ester group is included in salt in negatively charged ion.The example of salt comprises phenylbenzene iodine fluoroform sulphonate, (4-p-methoxy-phenyl) phenyl-iodide hexafluoro antimonate, (4-p-methoxy-phenyl) phenyl-iodide fluoroform sulphonate, two (4-tert-butyl-phenyl) iodine a tetrafluoro borate, two (4-tert-butyl-phenyl) iodine hexafluorophosphate, two (4-tert-butyl-phenyl) iodine hexafluoro antimonate, two (4-tert-butyl-phenyl) iodine fluoroform sulphonate, triphenylsulfonium hexafluorophosphate, triphenylsulfonium hexafluoro antimonate, triphenylsulfonium (1-adamantyl methoxyl group) carbonyl difluoro mesylate, triphenylsulfonium (3-methylol-1-adamantyl) methoxycarbonyl Difluore methane-sulfonic acid salt, triphenyl sulphur 1-(six hydrogen-2-oxo-3,5-methylene radical-2H-ring penta [b] furans-6-base oxygen carbonyls) Difluore methane-sulfonic acid salt, triphenylsulfonium (4-oxo-1-Buddha's warrior attendant alkoxyl group) carbonyl difluoro mesylate, triphenylsulfonium (3-hydroxyl-1-adamantyl) methoxycarbonyl Difluore methane-sulfonic acid salt, (4-aminomethyl phenyl) phenylbenzene sulfonium nine fluorine fourth sulfonate, (4-p-methoxy-phenyl) phenylbenzene sulfonium hexafluoro antimonate, (4-p-methoxy-phenyl) phenylbenzene sulfonium fluoroform sulphonate, (4-aminomethyl phenyl) phenylbenzene sulfonium fluoroform sulphonate, the pungent sulfonate of (4-aminomethyl phenyl) phenylbenzene sulfonium 17 fluorine, (2,4,6-trimethylphenyl) phenylbenzene sulfonium fluoroform sulphonate, (4-tert-butyl-phenyl) phenylbenzene sulfonium fluoroform sulphonate, (4-phenyl thiophenyl) phenylbenzene sulfonium hexafluorophosphate, (4-phenyl thiophenyl) phenylbenzene sulfonium hexafluoro antimonate, 1-(2-naphthoyl methyl) tetramethylene sulfide hexafluoro antimonate, 1-(2-naphthoyl methyl) tetramethylene sulfide fluoroform sulphonate, (4-hydroxyl-1-naphthyl) dimethyl sulfonium hexafluoro antimonate and (4-hydroxyl-1-naphthyl) dimethyl sulfonium fluoroform sulphonate.
The example of haloalkyl triaizine compounds comprises 2-methyl-4, two (trichloromethyl)-1 of 6-, 3, 5-triazine, 2, 4, 6-tri-(trichloromethyl)-1, 3, 5-triazine, 2-phenyl-4, two (trichloromethyl)-1 of 6-, 3, 5-triazine, 2-(4-chloro-phenyl-)-4, two (trichloromethyl)-1 of 6-, 3, 5-triazine, 2-(4-p-methoxy-phenyl)-4, two (trichloromethyl)-1 of 6-, 3, 5-triazine, 2-(4-methoxy-1-naphthyl)-4, two (trichloromethyl)-1 of 6-, 3, 5-triazine, 2-(benzo [d] [1, 3] dioxole-5-base)-4, two (trichloromethyl)-1 of 6-, 3, 5-triazine, 2-(4-methoxyl-styrene)-4, two (trichloromethyl)-1 of 6-, 3, 5-triazine, 2-(3, 4, 5-trimethoxy styryl)-4, two (trichloromethyl)-1.3 of 6-, 5-triazine, 2-(3, 4-dimethoxy-styryl)-4, two (trichloromethyl)-1 of 6-, 3, 5-triazine, 2-(2, 4-methoxyl-styrene)-4, two (trichloromethyl)-1 of 6-, 3, 5-triazine, 2-(2-methoxyl-styrene)-4, two (trichloromethyl)-1 of 6-, 3, 5-triazine, 2-(4-butyl phenyl ether vinyl)-4, two (trichloromethyl)-1 of 6-, 3, 5-triazine and 2-(4-amyl phenyl ether vinyl)-4, two (trichloromethyl)-1 of 6-, 3, 5-triazine.
The example of sulfonate compound comprises tosic acid 1-benzoyl-1-phenyl methyl esters (being commonly referred to " benzoin tosylate "), tosic acid 2-benzoyl-2-hydroxyl-2-phenyl chlorocarbonate (being commonly referred to " alpha-hydroxymethyl benzoin tosylate "), three (methylsulfonic acids) 1,2,3-benzene-three-ester, tosic acid 2,6-dinitrobenzene benzyl ester, tosic acid 2-p-Nitrobenzyl and tosic acid 4-p-Nitrobenzyl.
The example of two sulphones comprises phenylbenzene two sulfone and two (p-methylphenyl) two sulfone.
The example with the diazomethane compound of alkylsulfonyl comprises two (phenylSulphon) diazomethane, two (4-chloro-phenyl-sulphonyl) diazomethane, two (p-methylphenyl sulphonyl) diazomethane, two (4-tert-butyl-phenyl sulphonyl) diazomethane, two (2,4-xylyl sulphonyl) diazomethane, two (cyclohexylsulfonyl) diazomethane and (benzoyl) (phenylSulphon) diazomethane.
The example with the imide compound of sulfonyloxy comprises N-(phenylsulfonyloxy group) succinimide, N-(trimethyl fluoride sulfonyl oxygen base) succinimide, N-(trimethyl fluoride sulfonyl oxygen base) phthalic imidine, N-(trimethyl fluoride sulfonyl oxygen base)-5-norbornylene-2,3-dicarboximide, N-(trimethyl fluoride sulfonyl oxygen base) naphthalimide and N-(10-camphor sulfonyloxy) naphthalimide.Two or more acidogenic agents of use capable of being combined.
Acidogenic agent is being subject to can producing acid when activating radiation (radiation of such as EUV radiation, electron beam irradiation, 193 nano wave lengths or other source of radiation) irradiates.In described photoetching compositions, the consumption of acidogenic agent is enough to, when being subject to activating radiation and irradiating, in the coating of described composition, produce sub-image.Such as, in the total weight of solids of photoetching compositions for benchmark, the content of described acidogenic agent can be suitably 1-20 % by weight.
Photoetching compositions of the present invention can be used for the photoetching compositions that chemistry amplifies.
Photoetching agent pattern can produce according to the following steps: (1) applies the step of photoetching compositions on substrate, (2) by carrying out the dry step forming photoresist film, (3) described photoresist film is made to be exposed to the step of radiation, (4) cure the step of the described photoresist film through exposure, and (5) utilize alkaline developer to make the described photoresist film development through curing form the step of photoetching agent pattern thus.
The applying of photoetching compositions on substrate usually with conventional equipment as spin coater carries out.Any ordinary method that can be used by photoresist material field, is comprised dipping, spraying and spin coating, is applied in substrate by ready photoetching compositions solution.Before applying, the metre filter of photoetching compositions preferably through with aperture being 0.2 μm.When spin coating, such as, consider used swivel arrangement type and the permission time of rotating technics, the solids content per-cent of photoresist solution can be regulated, to provide the coat-thickness wanted.Suitable substrates comprises silicon, aluminium, fluoropolymer resin, silicon-dioxide, the silicon-dioxide of doping, silicon nitride, tantalum, copper, polysilicon, pottery, aluminium/copper mixture; Gallium arsenide and other this III/V compounds of group.Photoresist material also can be coated on anti-reflection coating.
The photoresist coating prepared by described technique is particularly suitable for silicon/silicon dioxide wafer, such as, for making microprocessor and other Small Scale Integration part.Aluminium/aluminum oxide wafer can also be used.Substrate also can comprise various fluoropolymer resin, particularly transparent polymer, such as polyester.
The formation of photoresist film usually with heating unit as hot plate or pressure reducer carry out, Heating temperature is generally 50-200 DEG C, and operating pressure is generally 1-1.0 × 105Pa.
Utilize exposure system that obtained photoresist film is exposed to radiation.Exposure is undertaken by the mask had corresponding to the pattern of required photoetching agent pattern usually.The example of exposure source comprise radiation UV-district laser light source (as KrF excimer laser (wavelength: 248nm), ArF excimer laser (wavelength: 193nm) and F2 laser apparatus (wavelength: 157nm)) and by the wavelength Conversion of laser from Solid State Laser light source (as YAG or semiconductor laser) light source of radiation UV district far away or vacuum UV district harmonic laser.
Stoving temperature through the photoresist film of exposure is generally 50-200 DEG C, preferred 70-150 DEG C.
The development of the photoresist film through curing is carried out with developing apparatus usually.Alkaline developer used can be any one in the various alkali aqueous solutions used in this area.In general, the normal aqueous solution using Tetramethylammonium hydroxide or (2-hydroxyethyl) trimethylammonium hydroxide (being often called " choline ").After development, the photoetching agent pattern formed preferably uses milli-Q water, and preferably removes remaining water on photoetching agent pattern and substrate.
Photoetching compositions of the present invention provides the photoetching agent pattern with fine resolution, therefore, photoetching compositions of the present invention is suitable for the photoetching of ArF excimer laser, the photoetching of KrF excimer laser, EUV (extreme ultraviolet) photoetching, EUV immersion lithographic and EB (electron beam) photoetching, and photoetching compositions of the present invention is particularly suitable for EUV (extreme ultraviolet) photoetching and EB (electron beam) photoetching.
Embodiment
Describe more specifically the present invention below by embodiment, these embodiments should not be construed as and limit the scope of the invention.Be used for any amount of substance used in " % " and " number " of the content representing any component and the following examples and comparative example all by weight, except separately explicitly pointing out.In the following examples, the weight-average molecular weight of any material used is the value recorded as standard reference material by gel permeation chromatography polystyrene standard.The structure of compound is determined by NMR and mass spectrum.
Synthetic example
Synthetic example 1
By equimolar 10-cyclopropyl-4-(trifluoromethyl) anthracene-1-carboxylic acid and appropriate ethyl acetate and 37% TBAH aqueous solution, gained mixture was in stirred at ambient temperature 1 hour.In gained mixture, add proper amount of methanol, gained mixture was in stirred at ambient temperature 16 hours.Concentrated gained solution, obtain D1 compound, productive rate is 67%.
1H-NMR (500.16MHz, d6-methyl-sulphoxide) δ ppm:0.96 (t, 12H), 1.33 (t, 6H), 1.50-1.52 (m, 8H), 3.35 (m, 6H), 6.70 (d, 1H), 7.32 (m, 2H), 7.29-7.32 (m, 1H), 7.67-7.82 (m, 4H)
13C-NMR (125.77MHz, d6-methyl-sulphoxide) δ ppm:9.33,12.55,13.80,20.81,28.01,60.17,112.92,122.8,123.11,123.66,127.12,128.29,131.6,135.2,136.74
Synthetic example 2
Equimolar 10-cyclopropyl-4-(trifluoromethyl) anthracene-1-carboxylic acid and the mixture of proper amount of methanol are mixed with the Tetramethylammonium hydroxide methanol solution of 37%, gained mixture was in stirred at ambient temperature 16 hours.Concentrated gained mixture, mixes gained resistates with appropriate ethyl acetate.The ion-exchange water washing three times of gained solution.Concentrated gained solution, obtain D2 compound, productive rate is 63%.
1H-NMR (500.16MHz, d6-methyl-sulphoxide) δ ppm:0.40-0.65 (m, 4H), 1.50 (t, 1H), 2.85 (m, 9H), 6.53 (d, 1H), 6.86 (d, 1H), 7.32 (t, 2H), 7.50-7.67 (m, 3H)
13C-NMR (125.77MHz, d6-methyl-sulphoxide) δ ppm:9.3,12.5,51.1,112.9,121.6,122.8,123.1,126.3,127.3,127.7,128.3,131.6,135.2,136.7,156.7
Synthetic example 3
Mixed with 10-cyclopropyl-4-(trifluoromethyl) anthracene-1-carboxylic acid by the mixture of equimolar four octyl group brometo de amonios and proper amount of methanol, gained mixture was in stirred at ambient temperature 16 hours.Concentrated gained mixture, mixes gained resistates with appropriate ethyl acetate.The sodium bicarbonate aqueous solution washing of appropriate 5% of gained solution, then washes twice with ion exchanged water.Concentrated gained solution, obtain D3 compound, productive rate is 47%.
1H-NMR (500.16MHz, d6-methyl-sulphoxide) δ ppm:0.96 (t, 6H), 1.29 (t, 12H), 1.33 (t, 4H), 1.50-1.52 (m, 7H), 3.35 (m, 4H), 6.70 (d, 1H), 7.32 (m, 2H), 7.67-7.73 (m, 2H)
13C-NMR (125.77MHz, d6-methyl-sulphoxide) δ ppm:9.3,12.5,14.1,22.8,25.8,27.7,29.1,31.9,60.4,112.9,121.6,122.8,123.1,126.3,127.3,127.7,128.3,131.6,135.2,136.7,156.7
Photoresist material preparation embodiment
Preparation embodiment 1
According to following ratio, formula (I) compound, resin, acidogenic agent are mixed in a solvent, use the fluoro-resin metre filter in 0.2 μm, aperture to prepare photoetching compositions.
| Component | Content (wt%) |
| Formula (I) compound | 0.2 |
| Resin | 4.2 |
| Acidogenic agent | 0.6 |
| Solvent | 95 |
Formula (I) compound in preparation embodiment 1 uses the compd A 1 prepared in synthetic example 1; Resin uses ECPMA
acidogenic agent uses tosic acid 2,6-dinitrobenzene benzyl ester; Solvent uses glycol dimethyl ether.
Preparation embodiment 2
According to following ratio, formula (I) compound, resin, acidogenic agent are mixed in a solvent, use the fluoro-resin metre filter in 0.2 μm, aperture to prepare photoetching compositions.
| Component | Content (wt%) |
| Formula (I) compound | 0.2 |
| Resin | 4.2 |
| Acidogenic agent | 0.6 |
| Solvent | 95 |
Formula (I) compound in preparation embodiment 2 uses the compd A 2 prepared in synthetic example 2; Resin uses ECPMA
acidogenic agent uses tosic acid 2,6-dinitrobenzene benzyl ester; Solvent uses glycol dimethyl ether.
Preparation embodiment 3
According to following ratio, formula (I) compound, resin, acidogenic agent are mixed in a solvent, use the fluoro-resin metre filter in 0.2 μm, aperture to prepare photoetching compositions.
| Component | Content (wt%) |
| Formula (I) compound | 0.2 |
| Resin | 4.2 |
| Acidogenic agent | 0.6 |
| Solvent | 95 |
Formula (I) compound in preparation embodiment 3 uses the compound A-13 prepared in synthetic example 3; Resin uses ECPMA
acidogenic agent uses tosic acid 2,6-dinitrobenzene benzyl ester; Solvent uses glycol dimethyl ether.
Preparation embodiment 4
According to following ratio, formula (I) compound, resin, acidogenic agent and basic cpd are mixed in a solvent, use the fluoro-resin metre filter in 0.2 μm, aperture to prepare photoetching compositions.
| Component | Content (wt%) |
| Formula (I) compound | 0.2 |
| Resin | 4.15 |
| Acidogenic agent | 0.6 |
| Basic cpd | 0.05 |
| Solvent | 95 |
Formula (I) compound in preparation embodiment 4 uses the compd A 1 prepared in synthetic example 1; Resin uses ECPMA
acidogenic agent uses tosic acid 2,6-dinitrobenzene benzyl ester; Basic cpd uses pyridine; Solvent uses glycol dimethyl ether.
Preparation embodiment 5
According to following ratio, formula (I) compound, resin, acidogenic agent and basic cpd are mixed in a solvent, use the fluoro-resin metre filter in 0.2 μm, aperture to prepare photoetching compositions.
| Component | Content (wt%) |
| Formula (I) compound | 0.2 |
| Resin | 4.15 |
| Acidogenic agent | 0.6 |
| Basic cpd | 0.05 |
| Solvent | 95 |
Formula (I) compound in preparation embodiment 5 uses the compd A 2 prepared in synthetic example 2; Resin uses ECPMA
acidogenic agent uses tosic acid 2,6-dinitrobenzene benzyl ester; Basic cpd uses pyridine; Solvent uses glycol dimethyl ether.
Preparation embodiment 6
According to following ratio, formula (I) compound, resin, acidogenic agent and basic cpd are mixed in a solvent, use the fluoro-resin metre filter in 0.2 μm, aperture to prepare photoetching compositions.
| Component | Content (wt%) |
| Formula (I) compound | 0.2 |
| Resin | 4.15 |
| Acidogenic agent | 0.6 |
| Basic cpd | 0.05 |
| Solvent | 95 |
Formula (I) compound in preparation embodiment 6 uses the compound A-13 prepared in synthetic example 3; Resin uses ECPMA
acidogenic agent uses tosic acid 2,6-dinitrobenzene benzyl ester; Basic cpd uses pyridine; Solvent uses glycol dimethyl ether.
Preparation embodiment 7
According to following ratio, formula (I) compound, resin, acidogenic agent are mixed in a solvent, use the fluoro-resin metre filter in 0.2 μm, aperture to prepare photoetching compositions.
| Component | Content (wt%) |
| Formula (I) compound | 0.2 |
| Resin | 4.2 |
| Acidogenic agent | 0.6 |
| Solvent E1 | 95 |
Formula (I) compound in preparation embodiment 7 uses the compound A-13 prepared in synthetic example 3; Resin uses ECPMA
acidogenic agent uses tosic acid 2,6-dinitrobenzene benzyl ester.
Preparation embodiment 8
According to following ratio, formula (I) compound, resin, acidogenic agent and basic cpd are mixed in a solvent, use the fluoro-resin metre filter in 0.2 μm, aperture to prepare photoetching compositions.
| Component | Content (wt%) |
| Formula (I) compound | 0.2 |
| Resin | 4.15 |
| Acidogenic agent | 0.6 |
| Basic cpd | 0.05 |
| Solvent E1 | 95 |
Formula (I) compound in preparation embodiment 8 uses the compound A-13 prepared in synthetic example 3; Resin uses ECPMA
acidogenic agent uses tosic acid 2,6-dinitrobenzene benzyl ester; Basic cpd uses pyridine.
Preparation embodiment 9
According to following ratio, formula (I) compound, resin, acidogenic agent and basic cpd are mixed in a solvent, use the fluoro-resin metre filter in 0.2 μm, aperture to prepare photoetching compositions.
| Component | Content (wt%) |
| Formula (I) compound | 0.2 |
| Resin | 4.15 |
| Acidogenic agent | 0.6 |
| Basic cpd | 0.05 |
| Solvent E1 | 95 |
Formula (I) compound in preparation embodiment 9 uses the compd A 2 prepared in synthetic example 2; Resin uses ECPMA
acidogenic agent uses tosic acid 2,6-dinitrobenzene benzyl ester; Basic cpd uses pyridine.
Preparation embodiment 10 (comparative example 1)
According to following ratio, compd B, resin, acidogenic agent are mixed in a solvent, use the fluoro-resin metre filter in 0.2 μm, aperture to prepare photoetching compositions.
| Component | Content (wt%) |
| Compd B | 0.2 |
| Resin | 4.2 |
| Acidogenic agent | 0.6 |
| Solvent | 95 |
Resin uses ECPMA
acidogenic agent uses tosic acid 2,6-dinitrobenzene benzyl ester; Solvent uses glycol dimethyl ether.
Preparation embodiment 11 (comparative example 2)
According to following ratio, compd B, resin, acidogenic agent and basic cpd are mixed in a solvent, use the fluoro-resin metre filter in 0.2 μm, aperture to prepare photoetching compositions.
| Component | Content (wt%) |
| Compd B | 0.2 |
| Resin | 4.15 |
| Acidogenic agent | 0.6 |
| Basic cpd | 0.05 |
| Solvent | 95 |
Resin uses ECPMA
acidogenic agent uses tosic acid 2,6-dinitrobenzene benzyl ester; Basic cpd uses pyridine; Solvent uses glycol dimethyl ether.
Preparation embodiment 12 (comparative example 3)
According to following ratio, compd B, resin, acidogenic agent and basic cpd are mixed in a solvent, use the fluoro-resin metre filter in 0.2 μm, aperture to prepare photoetching compositions.
| Component | Content (wt%) |
| Compd B | 3 |
| Resin | 15 |
| Acidogenic agent | 1 |
| Basic cpd | 1 |
| Solvent E1 | 80 |
Resin uses ECPMA
acidogenic agent uses tosic acid 2,6-dinitrobenzene benzyl ester; Basic cpd uses pyridine; Solvent uses glycol dimethyl ether.
In aforementioned preparation embodiment, containing following component in the solvent E1 of use: (1) glycol dimethyl ether 15 weight part, (2) ethyl acetate 40 weight part and (3) gamma-butyrolactone 5 weight part.The compd B used in comparative example is the compound with following structure:
In previous embodiment, compd A 1-A3 has negatively charged ion as identical in compd B.
Photoetching treatment
Photoetching treatment adopts this area ordinary method to carry out.Direct hot plate makes each silicon wafer at 110 DEG C, contact hexamethyldisilazane 60 seconds, after each photoetching compositions that spin coating is as above obtained on silicon wafer to drying, thickness is 0.10 μm.After applying each photoetching compositions, by the silicon wafer preliminary drying 60 seconds at the temperature of 110 DEG C being coated with each photoetching compositions like this.Adopt commercially available write electron-beam lithography system extreme ultraviolet (EUV) to expose, each silicon wafer it having formed each photoresist film is exposed to line and space pattern, progressively change exposure simultaneously.
After exposure, hot plate makes at the temperature of 100-110 DEG C each silicon wafer experience the post exposure bake of 60 seconds, then use (2-hydroxyethyl) trimethylammonium hydroxide aqueous development 60 seconds of 2.5 % by weight.
With each photoetching agent pattern that sem observation silicon substrate develops after development, result is shown in following table.
The slickness of pattern wall surface: with the pattern wall surface of the intensive line pattern of sem observation, when observing line edge roughness, being judged as "×" (poor), when not observing, being judged as "○" (good).
Resolving power: setting the exposure that each photoetching agent pattern becomes 1: 1 line and space pattern is effective sensitivity.Expose under being determined at effective sensitivity and the minimum feature of the line developed and space pattern.
The slickness of resolving power and pattern wall surface
Result in upper table shows, photoetching compositions containing compound of the present invention can produce the slickness of reasonable pattern wall surface, resolving power and effective sensitivity, and photoetching compositions of the present invention provides the photoetching agent pattern with fine resolution and is particularly suitable for the photoetching of KrF excimer laser, EUV lithography and EB photoetching.
The description of the invention described above illustrate and describes the present invention.In addition, the disclosure merely depict the preferred embodiments of the invention, should be appreciated that, the present invention can change or improve in the concept of the present invention expressed by this paper, and technology or the knowledge of this change or improvement and above-mentioned instruction and/or association area match.Therefore, this specification sheets is not used to the present invention to be limited to form disclosed herein.In addition, wish additional claim interpretation to be comprise alternative embodiment.
Claims (2)
1. compound shown in the formula for photoetching compositions (A):
Wherein R
1-R
3for C
1-C
8alkyl, Y is counter anion.
2. compound according to claim 1, is characterized in that R
1-R
3represent butyl, methyl and octyl group independently.
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| CN201410855760.0A CN104529795B (en) | 2014-12-31 | 2014-12-31 | A kind of compound for photoetching compositions |
| CN201510887556.1A CN105467763A (en) | 2014-12-31 | 2014-12-31 | Compound used for photoresist composition |
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| CN201410855760.0A CN104529795B (en) | 2014-12-31 | 2014-12-31 | A kind of compound for photoetching compositions |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1331257A (en) * | 2000-06-30 | 2002-01-16 | 海力士半导体有限公司 | Organic anti-reflecting paint polymer, anti-reflecting paint compsns. and its prepn. method |
| CN1828414A (en) * | 2005-03-02 | 2006-09-06 | 株式会社东进世美肯 | Polymer for forming anti-reflective coating |
| CN101556433A (en) * | 2008-04-11 | 2009-10-14 | 韩国锦湖石油化学株式会社 | Light absorbent and organic antireflection coating composition containing the same |
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2014
- 2014-12-31 CN CN201510887556.1A patent/CN105467763A/en not_active Withdrawn
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1331257A (en) * | 2000-06-30 | 2002-01-16 | 海力士半导体有限公司 | Organic anti-reflecting paint polymer, anti-reflecting paint compsns. and its prepn. method |
| CN1828414A (en) * | 2005-03-02 | 2006-09-06 | 株式会社东进世美肯 | Polymer for forming anti-reflective coating |
| CN101556433A (en) * | 2008-04-11 | 2009-10-14 | 韩国锦湖石油化学株式会社 | Light absorbent and organic antireflection coating composition containing the same |
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