WO2010061701A1 - 防食性フォトレジスト剥離剤組成物 - Google Patents
防食性フォトレジスト剥離剤組成物 Download PDFInfo
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- WO2010061701A1 WO2010061701A1 PCT/JP2009/068185 JP2009068185W WO2010061701A1 WO 2010061701 A1 WO2010061701 A1 WO 2010061701A1 JP 2009068185 W JP2009068185 W JP 2009068185W WO 2010061701 A1 WO2010061701 A1 WO 2010061701A1
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- anticorrosive
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- saccharide
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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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/42—Stripping or agents therefor
- G03F7/422—Stripping or agents therefor using liquids only
- G03F7/425—Stripping or agents therefor using liquids only containing mineral alkaline compounds; containing organic basic compounds, e.g. quaternary ammonium compounds; containing heterocyclic basic compounds containing nitrogen
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/02—Inorganic compounds ; Elemental compounds
- C11D3/04—Water-soluble compounds
- C11D3/046—Salts
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/02—Inorganic compounds
- C11D7/04—Water-soluble compounds
- C11D7/08—Acids
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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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/42—Stripping or agents therefor
- G03F7/422—Stripping or agents therefor using liquids only
- G03F7/423—Stripping or agents therefor using liquids only containing mineral acids or salts thereof, containing mineral oxidizing substances, e.g. peroxy compounds
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02041—Cleaning
- H01L21/02057—Cleaning during device manufacture
- H01L21/02068—Cleaning during device manufacture during, before or after processing of conductive layers, e.g. polysilicon or amorphous silicon layers
- H01L21/02071—Cleaning during device manufacture during, before or after processing of conductive layers, e.g. polysilicon or amorphous silicon layers the processing being a delineation, e.g. RIE, of conductive layers
Definitions
- the present invention relates to an anticorrosive photoresist remover composition, and particularly provides an anticorrosive photoresist remover composition having an excellent anticorrosive effect by containing a specific anticorrosive agent.
- Patent Document 1 describes various anticorrosive agents, and there is a description that an aromatic hydroxyl compound and a saccharide may be used in combination, but there is no specific example in this anticorrosive formulation.
- Patent Document 2 describes that a sugar (linear polyhydric alcohol) or an aromatic hydroxy compound is used as a corrosion inhibitor.
- a stripping composition comprising a combination of an aromatic hydroxy compound and a sugar is disclosed as follows. It is not specifically disclosed in the examples. Further, Patent Document 3 discloses a stripping solution composition containing saccharides, but does not describe any use of an aromatic hydroxy compound. Furthermore, Patent Document 7 relates to a non-aqueous cleaning composition containing a polar organic solvent, an organic hydroxylated amine compound, and the like, although there is a description regarding an aryl compound or the like in which two or more hydroxyl groups are directly bonded to a saccharide or an aromatic ring. There is no specific disclosure of a release agent composition comprising an aromatic hydroxy compound and a sugar in combination in Examples and the like.
- the present invention has been made to solve the above-mentioned problems, and has excellent anticorrosion for both copper and aluminum in a wide temperature range and in the presence and absence of water.
- An object of the present invention is to provide an anticorrosive photoresist remover composition that exhibits an effect.
- the present inventors have used the anticorrosive photoresist stripper composition using a combination of an aromatic polyhydroxy compound and a saccharide as an anticorrosive agent, and thus the above-mentioned problem.
- the present invention has been completed.
- the present invention 1. an anticorrosive photoresist stripping composition containing a polar organic solvent (A), an organic amine compound (B), and an anticorrosive agent (C) comprising a combination of an aromatic polyhydroxy compound and a saccharide; 2. the anticorrosive photoresist stripper composition according to the above 1, which contains a polar organic solvent (A), an organic amine compound (B), an anticorrosive agent (C) comprising a combination of an aromatic polyhydroxy compound and a saccharide, and water; 3.
- the anticorrosive photoresist stripping composition according to 1 or 2 above comprising only a polar organic solvent (A), an organic amine compound (B), an aromatic polyhydroxy compound and a saccharide, and an anticorrosive (C), and water alone, 4.
- the anticorrosive photoresist remover composition according to any one of 1 to 5 above, wherein the aromatic polyhydroxy compound is represented by the following general formula (a): R m —Ar— (OH) n (a) (In the formula, R is an alkyl group or an aryl group, Ar is an aromatic hydrocarbon structure, m is an integer of 0 to 4, and n is an integer of 2 to 6.) 7.
- the anticorrosive photoresist stripping composition according to any one of 1 to 7, wherein the anticorrosive (C) comprises an aromatic polyhydroxy compound and a saccharide in a mass ratio of 9: 1 to 1: 9. And 9.
- the above-mentioned 1 to 9 containing 19 to 95% by mass of the polar organic solvent (A), 4 to 80% by mass of the organic amine compound (B) and 0.001 to 10% by mass of the anticorrosive agent (C).
- the anticorrosive photoresist remover composition according to any one of 8; Is to provide.
- an anticorrosive photoresist stripper composition that exhibits an excellent anticorrosive effect in a wide temperature range and in the presence and absence of water for both copper and aluminum. Things can be provided.
- FIG. 3 is a graph showing the correlation between each water addition amount and the aluminum corrosion rate of the (anticorrosive) photoresist release agent compositions prepared in Examples 1 and 2 and Comparative Examples 1 to 3 (Table 3). It is a figure which shows the Cu corrosion rate in each temperature of the photoresist release agent composition prepared in Example 1 and Comparative Examples 3, 4 and 7 (Table 4). It is a figure which shows the Al corrosion rate in each temperature of the photoresist release agent composition prepared in Example 1 and Comparative Examples 3, 4, and 7 (Table 4).
- the anticorrosive photoresist stripping composition of the present invention contains an anticorrosive agent (C) comprising a combination of a polar organic solvent (A), an organic amine compound (B), an aromatic polyhydroxy compound and a saccharide.
- the polar organic solvent (A) is not particularly limited as long as it can dissolve organic amine compounds and aromatic polyhydroxy compounds and saccharides uniformly.
- Specific examples of the amide solvent include N-methyl-2-pyrrolidone (NMP), dimethylformamide (DMF), and a compound represented by the following general formula (1).
- NMP N-methyl-2-pyrrolidone
- DMF dimethylformamide
- an amide solvent having the following general formula is preferable, and specifically, 3-methoxy-N, N-dimethylpropionamide and 3-butoxy-N, N-dimethylpropionamide are more preferable.
- R 1 is a linear or branched alkyl group having 1 to 6 carbon atoms
- R 2 and R 3 are each independently a linear or branched alkyl group having 1 to 3 carbon atoms. is there.
- Specific examples of the linear alkyl group include methyl group, ethyl group, n-propyl group, n-butyl group, n-heptyl group and n-hexyl group.
- branched alkyl group examples include isopropyl group, s-butyl group, isobutyl group, t-butyl group, 2-methylbutyl group, 3-methylbutyl group, isopentyl group, 2-ethylpropyl group, and neopentyl group. It is done.
- ether alcohol solvent examples include diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monopropyl ether, diethylene glycol monobutyl ether (BDG), and the like.
- ester solvent examples include ⁇ -butyrolactone and butyl acetate.
- alcohol solvent examples include ethylene glycol and propylene glycol.
- the said polar organic solvent (A) may be used individually by 1 type, and may use 2 or more types together.
- amide solvents are preferable, and since they are amphiphilic and highly soluble, 3-methoxy-N, N-dimethylpropionamide and 3-butoxy-N, N-dimethylpropion Amides are particularly preferred. preferable.
- organic amine compound (B) examples include primary alkanolamines such as monoethanolamine, monoisopropanolamine, diglycolamine, N-methylethanolamine, N-methylpropanolamine, N-methylbutanolamine, N-ethyl Secondary amines such as ethanolamine and diethanolamine, secondary amines such as diethylamine, tertiary amines such as N, N-dimethylethanolamine, N-methyldiethanolamine, N-ethyldiethanolamine, N-propyldiethanolamine, N-butyldiethanolamine And tertiary amines such as alkanolamine and triethylamine.
- primary alkanolamines such as monoethanolamine, monoisopropanolamine, diglycolamine, N-methylethanolamine, N-methylpropanolamine, N-methylbutanolamine, N-ethyl Secondary amines such as ethanolamine and diethanolamine, secondary amines such as die
- ethanolamine compounds such as monoethanolamine, N-methylethanolamine and N, N-dimethylethanolamine can be preferably used.
- N-methylethanolamine which is a secondary alkanolamine
- N, N-dimethylethanolamine which is a tertiary alkanolamine.
- These organic amine compounds (B) may be used individually by 1 type, and may use 2 or more types together.
- the said anticorrosive (C) consists of a combination of an aromatic polyhydroxy compound and saccharides.
- aromatic polyhydroxy compound what is represented by the following general formula (a) is preferable.
- R m —Ar— (OH) n (a) Wherein R is an alkyl group or an aryl group, Ar is an aromatic hydrocarbon structure, m is an integer of 0 to 4, preferably 1 to 2, and n is 2 to 6, preferably 2 to It is an integer of 4.)
- R is an alkyl group or an aryl group.
- the alkyl group represented by R preferably has 1 to 50 carbon atoms, and more preferably has 1 to 20 carbon atoms.
- This alkyl group may be linear, branched or cyclic, and specific examples thereof include methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, tert-butyl group. Group, pentyl group, hexyl group, cyclohexyl group, heptyl group, octyl group, stearyl group and the like.
- the aryl group represented by R preferably has 6 to 50 carbon atoms, and more preferably has 6 to 18 carbon atoms.
- the aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a chrycenyl group, a biphenyl group, and a terphenyl group.
- the aromatic hydrocarbon structure represented by Ar preferably has 6 to 50 carbon atoms, and more preferably has 6 to 18 carbon atoms.
- Specific examples of the aromatic hydrocarbon structure include the structures of the groups listed as specific examples of the aryl group.
- aromatic polyhydroxy compound examples include pyrocatechol, t-butylcatechol, resorcinol, hydroquinone, pyrogallol, 1,2,4-benzenetriol, and hydroquinone is preferably used. These aromatic polyhydroxy compounds may be used individually by 1 type, and may use 2 or more types together.
- the saccharide examples include xylitol, sorbitol, arabitol, mannitol, glucose, galactose and the like, and xylitol and sorbitol are preferable. These saccharides may be used alone or in combination of two or more.
- the content ratio of the aromatic polyhydroxy compound and the saccharide in the anticorrosive agent (C) is preferably in the range of 9: 1 to 1: 9 by mass from the viewpoint of the anticorrosive effect, and 8: More preferably, it is in the range of 2 to 5: 5.
- the specific composition ratio of the anticorrosive photoresist stripping composition of the present invention is not particularly limited, and it is sufficient that the stripping performance can be used as a stripping agent.
- the polar organic solvent (A), organic amine With respect to the total amount of the compound (B) and the anticorrosive (C), the polar organic solvent (A) is 20 to 98% by mass, the organic amine compound (B) is 1 to 79% by mass, and the anticorrosive (C ) Is preferably contained in an amount of 0.001 to 10% by mass, (A) in an amount of 50 to 96% by mass, the organic amine compound (B) in an amount of 3 to 49% by mass, and the anticorrosive (C) in an amount of 0.8%.
- the content is from 01 to 5% by mass.
- the anticorrosive agent (C) exhibits an anticorrosive effect even in a very small amount, and preferably contains 0.001 to 10% by mass, more preferably 0.01 to 5% by mass. Further, the anticorrosive photoresist stripping composition of the present invention contains the anticorrosive (C) in an extremely small amount of 0.001 to 1% by mass, and further 0.01 to 0.5% by mass. Shows good anticorrosion properties.
- the anticorrosive photoresist remover composition of the present invention may further contain water.
- water In general, the presence of water in the photoresist stripper tends to cause degradation of stripping performance and corrosion of the inorganic substrate, but the anticorrosive photoresist stripper composition of the present invention is only in the absence of water. It exhibits an excellent anticorrosive effect even in the presence.
- the water content in the anticorrosive photoresist stripper composition of the present invention is 100 masses of water with respect to 100 mass parts of the total amount of the polar organic solvent (A), organic amine compound (B) and anticorrosive agent (C). Part or less, preferably 20 parts by weight or less of water.
- the total amount of the polar organic solvent (A), the organic amine compound (B) and the anticorrosive (C) is 100 parts by mass.
- the anticorrosive photoresist stripper composition of the present invention which is effective not only in the absence of water but also in the presence of water, a uniform anticorrosive effect is exhibited over a wide temperature range. Control is easy, and there is an advantage that the optimum temperature can be determined from the viewpoint of peeling performance.
- the anticorrosive photoresist stripping composition of the present invention is used preferably at 30 to 90 ° C., more preferably 40 to 80 ° C., and even more preferably 65 to 80 ° C., the effects of the present invention are remarkably exhibited.
- the anticorrosive photoresist remover composition of the present invention exhibits anticorrosive ability for various inorganic substrates.
- semiconductor wiring materials such as silicon, polysilicon, silicon oxide film, aluminum, aluminum alloy, titanium, titanium-tungsten, titanium nitride, tungsten, or compound semiconductors such as gallium-arsenic, gallium-phosphorus, indium-phosphorus, etc.
- LCD glass substrates and the like can be mentioned, and in particular, it exhibits excellent anticorrosive ability against metals such as aluminum, aluminum alloy (Al—Cu), copper, iridium, titanium, silicon and polysilicon.
- the anticorrosive photoresist stripping composition of the present invention is a photoresist film coated on an inorganic substrate, a photoresist layer remaining after dry etching of a photoresist film coated on an inorganic substrate, or ashing after dry etching. Can be used to remove the photoresist film on the inorganic substrate such as the remaining photoresist residue, and when removing these, use heating or ultrasonic waves appropriately as necessary. Can do.
- the treatment method using the anticorrosive photoresist stripping composition of the present invention is generally a spray method, but other methods such as an immersion method may be used.
- Example 1 Anticorrosive 1. Based on 86.5% by weight of 3-methoxy-N, N-dimethylpropionamide and 12.5% by weight of N-MeEtAm and consisting of 0.5% by weight of hydroquinone and 0.5% by weight of xylitol. 0% by mass was added to prepare an anticorrosive photoresist remover composition. The blending ratio is shown in Table 1. Moreover, about the obtained anticorrosion photoresist peeling agent composition, the corrosion rate of copper and aluminum, water concentration dependence, and temperature dependence were evaluated in the procedure shown below.
- test pieces Two types of test pieces were prepared by vapor-depositing Al and Cu (about 7000 mm) on a glass plate.
- the anticorrosive photoresist remover composition obtained above was maintained at 60 ° C., and two types of test pieces were immersed for 33 minutes. After immersion, the test piece was thoroughly washed with isopropyl alcohol, then air-dried, and the surface resistance was measured by a 4-probe method to calculate the corrosion rate.
- the evaluation results of the corrosion rate for Cu are shown in Table 2
- evaluation results of the corrosion rate for Al are shown in Table 3, respectively.
- Example 2 A photoresist remover composition was prepared in the same manner as in Example 1 except that the composition ratio shown in Table 1 was used, and its corrosion rate and water concentration dependency were evaluated. The evaluation results of the corrosion rate for Cu are shown in Table 2, and the evaluation results of the corrosion rate for Al are shown in Table 3, respectively.
- Comparative Examples 1 and 2 A photoresist stripping composition was prepared in the same manner as in Example 1 except that the blending ratio shown in Table 1 was used, and its corrosion rate and water concentration dependency were evaluated. The evaluation results of the corrosion rate for Cu are shown in Table 2, and the evaluation results of the corrosion rate for Al are shown in Table 3, respectively.
- Comparative Example 3 A photoresist stripping composition was prepared in the same manner as in Example 1 except that the blending ratio shown in Table 1 was used, and its corrosion rate, water concentration dependency, and temperature dependency were evaluated.
- the evaluation results of the corrosion rate for Cu are shown in Table 2
- the evaluation results of the corrosion rate for Al are shown in Table 3
- the evaluation results of temperature dependence are shown in Table 4, respectively.
- Comparative Example 1 not containing these, Comparative Example 2 containing only xylitol, and Comparative Example 3 containing only hydroquinone have particularly high corrosion rates for copper.
- the anticorrosive photoresist stripping compositions obtained in Examples 1 and 2 have excellent anticorrosive properties against both copper and aluminum.
- Comparative Examples 1 and 2 even when water was added to the anticorrosive photoresist stripping composition, excellent anticorrosive properties were exhibited in a wide water concentration region, whereas in Comparative Examples 1 to 3, With increasing water concentration, the corrosion rate, especially for copper, is significantly higher.
- the anticorrosive photoresist stripper composition obtained in Example 1 exhibits anticorrosion properties in a wide temperature range of 40 ° C. to 80 ° C., whereas the photoresists obtained in Comparative Examples 3, 4 and 7
- the stripping composition has a particularly high corrosion rate with respect to copper depending on the temperature.
- Examples 3 and 4 An anticorrosive photoresist remover composition was prepared in the same manner as in Example 1 except that the blending ratios shown in Table 5 were used, and their corrosion rates were evaluated. The evaluation results are shown in Table 5.
- Example 3 Based on Examples 3 and 4, it was examined whether there is a difference in the anticorrosive effect due to the use of the anticorrosive agent due to the difference in amine.
- monoethanolamine was blended with 3-methoxy-N, N-dimethylpropionamide, and in Example 4, tertiary alkanolamine DMAE was blended, and the corrosion rate evaluation results shown in Table 5 were obtained. It was. From this result, it can be seen that the effect of using both anticorrosives is greater when a system containing a secondary amine or a tertiary amine is used than when a primary amine is added.
- Examples 5 to 13 An anticorrosive photoresist remover composition was prepared in the same manner as in Example 1 except that the blending ratios shown in Tables 6 and 7 were used. 40 parts by mass of water was added to 100 parts by mass of the obtained anticorrosive photoresist stripping composition, and the corrosion rate was evaluated. The evaluation results are shown in Tables 6 and 7.
- Example 14 An anticorrosive photoresist remover composition was prepared in the same manner as in Example 1 except that the blending ratios shown in Table 8 were used. 10 parts by weight of water was added to 100 parts by weight of the obtained anticorrosive photoresist stripping composition, and the corrosion rate was evaluated. Table 8 shows the evaluation results.
- Comparative Example 4 A photoresist stripping composition was prepared in the same manner as in Example 14 except that the blending ratio shown in Table 8 was used, and the corrosion rate and temperature dependency were evaluated. Table 8 shows the evaluation results of the corrosion rate, and Table 4 shows the evaluation results of the temperature dependence.
- Comparative Examples 5 and 6 A photoresist stripping composition was prepared in the same manner as in Example 14 except that the blending ratio shown in Table 8 was used, and the corrosion rate was evaluated. Table 8 shows the evaluation results.
- Example 15 An anticorrosive photoresist remover composition was prepared in the same manner as in Example 1 except that the blending ratios shown in Table 9 were used. Moreover, the corrosion rate of the obtained anticorrosive photoresist stripping composition was evaluated. Table 9 shows the evaluation results.
- Comparative Example 7 A photoresist remover composition was prepared in the same manner as in Example 15 except that the blending ratio shown in Table 9 was used, and the corrosion rate and temperature dependency were evaluated. Table 9 shows the evaluation results of the corrosion rate, and Table 4 shows the evaluation results of the temperature dependence.
- Comparative Examples 8 and 9 A photoresist stripping composition was prepared in the same manner as in Example 15 except that the blending ratio shown in Table 9 was used, and the corrosion rate was evaluated. Table 9 shows the evaluation results.
- Example 16 An anticorrosive photoresist remover composition was prepared in the same manner as in Example 1 except that sorbitol was used in place of xylitol and the blending ratio shown in Table 10 was used, and the corrosion rate was evaluated. Table 10 shows the evaluation results. In addition, the stripping performance of the anticorrosive photoresist stripper composition was evaluated by the following procedure.
- a positive resist composition (manufactured by Fuji Film Electronics Materials Co., Ltd., HPR204, 8 cps) was applied with a spin coater (750 rpm ⁇ 20 s) on a sufficiently cleaned glass substrate, and baked in an oven under the following conditions. .
- Firing conditions 80 ° C. ⁇ 15 minutes + 130 ° C. ⁇ 15 minutes + 160 ° C. ⁇ 15 minutes This glass substrate was cut into a size of about 5 ⁇ 5 mm to obtain a test piece.
- About 10 milliliters of the anticorrosive photoresist remover composition was placed in a beaker, and the temperature was kept constant at 70 ° C. with an oil bath. The test piece was immersed in this, and after 2 minutes, it was immediately rinsed with pure water and then sufficiently dried by air drying. When the test piece was observed with a scanning electron microscope (SEM), it was confirmed that the resist was completely removed.
- SEM scanning electron microscope
- Comparative Example 10 A photoresist remover composition was prepared in the same manner as in Example 16 except that the blending ratio shown in Table 10 was used, and the corrosion rate was evaluated. The results are shown in Table 10.
- the anticorrosive photoresist stripper composition of the present invention formulated with a combination of an aromatic polyhydroxy compound and a saccharide has a low total anticorrosive concentration. It was also confirmed that the anticorrosion effect was sufficiently exhibited. On the other hand, with low concentration addition of sorbitol alone (Comparative Example 10), the corrosion protection effect against aluminum was confirmed, but copper corrosion proceeded greatly. As described above, it was confirmed that the anticorrosive photoresist remover composition of the present invention has no temperature dependency, exhibits high anticorrosion properties at a wide range of temperatures, and exhibits an anticorrosive effect at a wide range of water concentrations.
- the anticorrosion property is high for both copper and aluminum in the entire amount of water addition compared to a resist stripper formulated with xylitol or hydroquinone alone. It can be seen that Further, as shown in FIGS. 3 and 4, the anticorrosive photoresist stripper composition of the present invention has a temperature dependency lower than that of other anticorrosion formulations, and sufficiently exhibits an anticorrosive effect against both copper and aluminum at any temperature. It can be confirmed that it is exerted.
- the anticorrosive photoresist stripper composition of the present invention exhibits an excellent anticorrosive effect for both copper and aluminum, and has low water concentration dependency and temperature dependency. It is useful as a release agent for a resist coated on an inorganic substrate.
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Abstract
Description
これらの剥離剤については、高精度の回路配線を製造する観点から、剥離する際に金属配線として用いられているアルミニウムや銅、あるいは無機質基体を腐食させずにレジストを剥離できるものであることが要求されている。これらの要求を満たすため、安息香酸や酢酸等のカルボン酸、キレート化合物、ソルビトールなどの糖類、カテコールなどのポリヒドロキシ芳香族を防食剤として添加する手法が検討されている。
ところで、液晶ディスプレイにはアルミ配線が多く採用されているが、近年の液晶ディスプレイの大型化に伴い、コスト面やテレビの薄型化の観点からアルミニウムよりも抵抗値が小さい銅配線の採用が検討されている。そこでアルミニウムだけでなく銅に対しても優れた防食効果を有するレジスト剥離剤が望まれている。しかしながら、銅及びアルミニウムの両方に十分な防食効果を発揮できる防食処方をした剥離剤は、現在までに知られていない。
特許文献2には、腐食防止剤として糖(直鎖多価アルコール)や芳香族ヒドロキシ化合物を用いることは記載されているが、芳香族ヒドロキシ化合物と糖とを併用してなる剥離液組成物は、実施例中などにおいて具体的に開示されていない。
また、特許文献3には、糖類を含有する剥離液組成物が開示されているものの、芳香族ヒドロキシ化合物を用いることについては、何ら記載されていない。
さらに、特許文献7は、極性有機溶媒及び有機ヒドロキシル化アミン化合物等を含有する非水性の洗浄組成物に関し、糖類や芳香環に水酸基が2個以上直接結合したアリール化合物等に関する記載があるものの、実施例等において芳香族ヒドロキシ化合物と糖とを併用してなる剥離剤組成物について具体的な開示はない。
1. 極性有機溶剤(A)、有機アミン化合物(B)並びに芳香族ポリヒドロキシ化合物及び糖類の組合せからなる防食剤(C)を含有する防食性フォトレジスト剥離剤組成物、
2. 極性有機溶剤(A)、有機アミン化合物(B)、芳香族ポリヒドロキシ化合物及び糖類の組合せからなる防食剤(C)並びに水を含有する上記1記載の防食性フォトレジスト剥離剤組成物、
3.極性有機溶剤(A)、有機アミン化合物(B)、芳香族ポリヒドロキシ化合物及び糖類の組合せからなる防食剤(C)並びに水のみからなる上記1又は2記載の防食性フォトレジスト剥離剤組成物、
4. 前記極性有機溶剤(A)が、アミド系溶剤である上記1~3のいずれかに記載の防食性フォトレジスト剥離剤組成物、
5. 前記有機アミン化合物(B)が、モノエタノールアミン、N-メチルエタノールアミン及びN,N-ジメチルエタノールアミンから選ばれる1種以上である上記1~4のいずれかに記載の防食性フォトレジスト剥離剤組成物、
6. 前記芳香族ポリヒドロキシ化合物が下記一般式(a)で表される上記1~5のいずれかに記載の防食性フォトレジスト剥離剤組成物、
Rm-Ar-(OH)n・・・(a)
(式中、Rはアルキル基又はアリール基であり、Arは芳香族炭化水素構造であり、mは0~4の整数であり、nは2~6の整数である。)
7. 前記糖類が、キシリトール、ソルビトール、アラビトール、マンニトール、グルコース及びガラクトースから選ばれる1種以上である上記1~6のいずれかに記載の防食性フォトレジスト剥離剤組成物、
8. 前記防食剤(C)が、芳香族ポリヒドロキシ化合物と糖類とを、質量比9:1~1:9の割合で含む上記1~7のいずれかに記載の防食性フォトレジスト剥離剤組成物、及び
9. 前記極性有機溶剤(A)19~95質量%、前記有機アミン化合物(B)4~80質量%及び前記防食剤(C)0.001~10質量%を含有する上記1~8のいずれかに記載の防食性フォトレジスト剥離剤組成物、
を提供するものである。
前記極性有機溶剤(A)としては、有機アミン化合物および芳香族ポリヒドロキシ化合物と糖類を均一に溶解することができるものであれば特に限定されず、アミド系溶剤、エーテルアルコール系溶剤、アルコール系溶剤、エステル系溶剤、ジメチルスルホキシド(DMSO)等が挙げられる。アミド系溶剤の具体例としてはN-メチル-2-ピロリドン(NMP)、ジメチルフォルムアミド(DMF)、下記一般式(1)で表わされる化合物等が挙げられる。特に下記一般式のアミド系溶剤が好ましく、具体的には、3-メトキシ-N,N-ジメチルプロピオンアミド、3-ブトキシ-N,N-ジメチルプロピオンアミドがより好ましい。
上記直鎖状アルキル基の具体例としては、メチル基、エチル基、n-プロピル基、n-ブチル基、n-ヘプチル基及びn-ヘキシル基が挙げられる。
上記分岐状アルキル基の具体例としては、イソプロピル基、s-ブチル基、イソブチル基、t-ブチル基、2-メチルブチル基、3-メチルブチル基、イソペンチル基、2-エチルプロピル基、ネオペンチル基が挙げられる。
エステル系溶剤の具体例としては、γ-ブチロラクトン、酢酸ブチル等が挙げられる。
アルコール系溶剤の具体例としては、エチレングリコール、プロピレングリコールなどが挙げられる。
上記極性有機溶剤(A)は1種を単独で用いてもよく、また、2種以上を併用してもよい。上記極性有機溶剤(A)の中でもアミド系溶剤が好ましく、また、両親媒性で高い溶解性を有するため、3-メトキシ-N,N-ジメチルプロピオンアミド及び3-ブトキシ-N,N-ジメチルプロピオンアミドが特に好ましい。
好ましい。
前記芳香族ポリヒドロキシ化合物としては、下記一般式(a)で表されるものが好ましい。
Rm-Ar-(OH)n・・・(a)
(式中、Rはアルキル基又はアリール基であり、Arは芳香族炭化水素構造であり、mは0~4、好ましくは1~2の整数であり、nは2~6、好ましくは2~4の整数である。)
上記一般式(a)においてRで示されるアルキル基としては、炭素数1~50のものが好ましく、炭素数1~20のものがより好ましい。このアルキル基は、直鎖状、分岐状、環状のいずれであってもよく、その具体例としては、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、sec-ブチル基、tert-ブチル基、ペンチル基、ヘキシル基、シクロヘキシル基、ヘプチル基、オクチル基、ステアリル基等が挙げられる。
上記一般式(a)においてRで示されるアリール基としては、炭素数6~50のものが好ましく、炭素数6~18のものがより好ましい。アリール基の具体例としては、フェニル基、ナフチル基、アントラセニル基、ピレニル基、クリセニル基、ビフェニル基、ターフェニル基等が挙げられる。
上記一般式(a)においてArで示される芳香族炭化水素構造としては、炭素数6~50のものが好ましく、炭素数6~18のものがより好ましい。芳香族炭化水素構造の具体例としては、上記アリール基の具体例として挙げられた基の構造が挙げられる。
本発明においては、防食剤(C)における芳香族ポリヒドロキシ化合物と糖類との含有割合は、防食効果の観点から、質量比で9:1~1:9の範囲にあることが好ましく、8:2~5:5の範囲にあることがより好ましい。
また、本発明の防食性フォトレジスト剥離剤組成物は、前記防食剤(C)を0.001~1質量%、さらには0.01~0.5質量%のごく微量を含有するものであっても良好な防食性を示す。
本発明の防食性フォトレジスト剥離剤組成物における水分量としては、上記極性有機溶剤(A)、有機アミン化合物(B)及び防食剤(C)の合計量100質量部に対して、水100質量部以下が好ましく、水20質量部以下がより好ましい。一方、防食性フォトレジスト剥離剤組成物の引火点をなくし、取扱いを容易とする観点からは、極性有機溶剤(A)、有機アミン化合物(B)及び防食剤(C)の合計量100質量部に対して、水20質量部以上を含有することが好ましく、水20~100質量部含有することがより好ましい。
<配合成分>
実施例1~17及び比較例1~10において用いた配合成分を以下に示す。
極性有機溶剤(A):
3-メトキシ-N,N-ジメチルプロピオンアミド
ジエチレングリコールモノブチルエーテル(BDG、和光純薬工業株式会社製)
有機アミン化合物(B):
N-メチルエタノールアミン(N-MeEtAm、和光純薬工業株式会社製)
モノエタノールアミン(MEA、和光純薬工業株式会社製)
N,N-ジメチルエタノールアミン(DMAE、和光純薬工業株式会社製)
防食剤(C):
芳香族ポリヒドロキシ化合物:
ヒドロキノン(和光純薬工業株式会社製)
糖類:
キシリトール(シグマ-アルドリッチ社製)
ソルビトール(純正化学株式会社製)
3-メトキシ-N,N-ジメチルプロピオンアミド 86.5質量%とN-MeEtAm 12.5質量%をベースとし、これにヒドロキノン0.5質量%及びキシリトール0.5質量%からなる防食剤1.0質量%を添加し、防食性フォトレジスト剥離剤組成物を調製した。配合比率を表1に示す。また、得られた防食性フォトレジスト剥離剤組成物について、銅及びアルミニウムの腐食速度、水濃度依存性及び温度依存性を以下に示す手順で評価した。
ガラス板にAl、Cuをそれぞれ蒸着(約7000Å)して2種類の試験片を作製した。上記で得られた防食性フォトレジスト剥離剤組成物を60℃に維持し、2種類の試験片を33分間浸漬した。浸漬後、試験片をイソプロピルアルコールで十分に洗浄し、その後風乾させて4探針法によって表面抵抗を測定し、腐食速度を算出した。Cuに対する腐食速度の評価結果を表2に、Alに対する腐食速度の評価結果を表3にそれぞれ示す。
防食性フォトレジスト剥離剤組成物100質量部に対し、水1~99質量部を添加し、上記と同様にして腐食速度を評価した。Cuに対する腐食速度の評価結果を表2に、Alに対する腐食速度の評価結果を表3にそれぞれ示す。
処理温度40℃及び80℃について、それぞれ上記と同様にして腐食速度を評価した。各温度における腐食速度の評価結果を表4に示す。
表1に示す組成比とした以外は実施例1と同様にしてフォトレジスト剥離剤組成物を調製し、その腐食速度及び水濃度依存性を評価した。Cuに対する腐食速度の評価結果を表2に、Alに対する腐食速度の評価結果を表3にそれぞれ示す。
表1に示す配合比率とした以外は実施例1と同様にしてフォトレジスト剥離剤組成物を調製し、その腐食速度及び水濃度依存性を評価した。Cuに対する腐食速度の評価結果を表2に、Alに対する腐食速度の評価結果を表3にそれぞれ示す。
表1に示す配合比率とした以外は実施例1と同様にしてフォトレジスト剥離剤組成物を調製し、その腐食速度、水濃度依存性及び温度依存性を評価した。Cuに対する腐食速度の評価結果を表2に、Alに対する腐食速度の評価結果を表3に、温度依存性の評価結果を表4にそれぞれ示す。
また、実施例1及び2では、防食性フォトレジスト剥離剤組成物に水を添加しても、広い水濃度領域で優れた防食性が発現しているのに対し、比較例1~3では、水濃度の増加と共に特に銅に対する腐食速度が著しく高くなっている。
さらに、実施例1で得られた防食性フォトレジスト剥離剤組成物は、40℃~80℃の幅広い温度域において防食性を示すのに対し、比較例3、4及び7で得られたフォトレジスト剥離剤組成物は、温度によって特に銅に対する腐食速度が高くなっている。
表5に示す配合比率とした以外は実施例1と同様にして防食性フォトレジスト剥離剤組成物を調製し、それらの腐食速度を評価した。評価結果を表5に示す。
表6及び7に示す配合比率とした以外は実施例1と同様にして防食性フォトレジスト剥離剤組成物を調製した。得られた防食性フォトレジスト剥離剤組成物100質量部に対し、水40質量部を添加し、その腐食速度を評価した。評価結果を表6及び7に示す。
表8に示す配合比率とした以外は実施例1と同様にして防食性フォトレジスト剥離剤組成物を調製した。得られた防食性フォトレジスト剥離剤組成物100質量部に対し、水10質量部を添加し、その腐食速度を評価した。評価結果を表8に示す。
表8に示す配合比率とした以外は実施例14と同様にしてフォトレジスト剥離剤組成物を調製し、腐食速度及び温度依存性を評価した。腐食速度の評価結果を表8に、温度依存性の評価結果を表4にそれぞれ示す。
表8に示す配合比率とした以外は実施例14と同様にしてフォトレジスト剥離剤組成物を調製し、腐食速度を評価した。評価結果を表8に示す。
表9に示す配合比率とした以外は実施例1と同様にして防食性フォトレジスト剥離剤組成物を調製した。また、得られた防食性フォトレジスト剥離剤組成物の腐食速度を評価した。評価結果を表9に示す。
表9に示す配合比率とした以外は実施例15と同様にしてフォトレジスト剥離剤組成物を調製し、腐食速度及び温度依存性を評価した。腐食速度の評価結果を表9に、温度依存性の評価結果を表4にそれぞれ示す。
表9に示す配合比率とした以外は実施例15と同様にしてフォトレジスト剥離剤組成物を調製し、腐食速度を評価した。評価結果を表9に示す。
キシリトールに代えてソルビトールを使用し、表10に示す配合比率とした以外は実施例1と同様にして防食性フォトレジスト剥離剤組成物を調製し、その腐食速度を評価した。評価結果を表10に示す。また、防食性フォトレジスト剥離剤組成物の剥離性能を以下に示す手順で評価した。
充分に洗浄したガラス基板上に、ポジ型レジスト組成物(富士フィルム エレクトロニクスマテリアルズ株式会社製、HPR204、8cps)をスピンコーターで(750rpm×20s)で塗布し、オーブンにて以下の条件で焼成した。
焼成条件:80℃×15分 + 130℃×15分 + 160℃×15分
このガラス基板を約5×5mmの大きさにカットして試験片を得た。
ビーカーに約10ミリリットルの防食性フォトレジスト剥離剤組成物を入れ、オイルバスにより70℃に恒温した。この中に試験片を浸漬し、2分後に取り出し直ぐに純水で十分にリンスした後、風乾により充分乾燥させた。
試験片を走査型電子顕微鏡(SEM)で観察したところ、完全にレジストが除去されていることが確認された。
表10に示す配合比率とした以外は実施例16と同様にしてフォトレジスト剥離剤組成物を調製し、その腐食速度を評価した。結果を表10に示す。
以上のように、本発明の防食性フォトレジスト剥離剤組成物は、温度依存性がなく、幅広い温度で高い防食性を示し、また、幅広い水濃度において防食効果を示すことが確認された。
Claims (9)
- 極性有機溶剤(A)、有機アミン化合物(B)並びに芳香族ポリヒドロキシ化合物及び糖類の組合せからなる防食剤(C)を含有する防食性フォトレジスト剥離剤組成物。
- 極性有機溶剤(A)、有機アミン化合物(B)、芳香族ポリヒドロキシ化合物及び糖類の組合せからなる防食剤(C)並びに水を含有する請求項1記載の防食性フォトレジスト剥離剤組成物。
- 極性有機溶剤(A)、有機アミン化合物(B)、芳香族ポリヒドロキシ化合物及び糖類の組合せからなる防食剤(C)並びに水のみからなる請求項1記載の防食性フォトレジスト剥離剤組成物。
- 前記極性有機溶剤(A)が、アミド系溶剤である請求項1記載の防食性フォトレジスト剥離剤組成物。
- 前記有機アミン化合物(B)が、モノエタノールアミン、N-メチルエタノールアミン及びN,N-ジメチルエタノールアミンから選ばれる1種以上である請求項1記載の防食性フォトレジスト剥離剤組成物。
- 前記芳香族ポリヒドロキシ化合物が下記一般式(a)で表される請求項1記載の防食性フォトレジスト剥離剤組成物。
Rm-Ar-(OH)n・・・(a)
(式中、Rはアルキル基又はアリール基であり、Arは芳香族炭化水素構造であり、mは0~4の整数であり、nは2~6の整数である。) - 前記糖類が、キシリトール、ソルビトール、アラビトール、マンニトール、グルコース及びガラクトースから選ばれる1種以上である請求項1記載の防食性フォトレジスト剥離剤組成物。
- 前記防食剤(C)が、芳香族ポリヒドロキシ化合物と糖類とを、質量比9:1~1:9の割合で含む請求項1記載の防食性フォトレジスト剥離剤組成物。
- 前記極性有機溶剤(A)、有機アミン化合物(B)及び防食剤(C)の合計量に対して、前記極性有機溶剤(A)19~95質量%、前記有機アミン化合物(B)4~80質量%及び前記防食剤(C)0.001~10質量%を含有する請求項1記載の防食性フォトレジスト剥離剤組成物。
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- 2009-10-22 WO PCT/JP2009/068185 patent/WO2010061701A1/ja active Application Filing
- 2009-10-22 JP JP2010540428A patent/JP5302334B2/ja active Active
- 2009-10-22 CN CN200980155620.XA patent/CN102301282B/zh active Active
- 2009-11-09 TW TW98137945A patent/TWI470380B/zh not_active IP Right Cessation
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JP2017040928A (ja) * | 2010-12-02 | 2017-02-23 | エルティーシー カンパニー リミテッド | 1級アルカノールアミンを含むlcd製造用フォトレジスト剥離液組成物 |
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WO2018088511A1 (ja) * | 2016-11-11 | 2018-05-17 | 株式会社カネコ化学 | 硬化性樹脂の硬化物の剥離剤、硬化性樹脂の硬化物の膨潤剤及び硬化性樹脂の硬化フォームの減容剤 |
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Also Published As
Publication number | Publication date |
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CN102301282B (zh) | 2014-03-05 |
JPWO2010061701A1 (ja) | 2012-04-26 |
TWI470380B (zh) | 2015-01-21 |
CN102301282A (zh) | 2011-12-28 |
TW201035702A (en) | 2010-10-01 |
JP5302334B2 (ja) | 2013-10-02 |
KR20110096126A (ko) | 2011-08-29 |
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