CA1179581A - Stripping compositions and method of stripping resists - Google Patents
Stripping compositions and method of stripping resistsInfo
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- CA1179581A CA1179581A CA000410275A CA410275A CA1179581A CA 1179581 A CA1179581 A CA 1179581A CA 000410275 A CA000410275 A CA 000410275A CA 410275 A CA410275 A CA 410275A CA 1179581 A CA1179581 A CA 1179581A
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- stripping composition
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Abstract
B-1185 C-1 STRIPPING COMPOSITIONS AND METHODS OF STRIPPING RESISTS Abstract of the Disclosure Stripping compositions for removing resist materials from substrates comprise compositions of a 2-pyrrolidinone compound and a diethylene glycol monoalkyl ether compound. Polyethylene glycol may be added to provide even more effective stripping compositions.
Description
B-lla5 C-l STRIPPING COMPOSITIONS
AND METHODS OF STRIPPING RESI~TS
Field of the Invention This invention relates to novel resist stripping compositions and to methods of stripping resists em-ploying said stripping compositions. More particu-larly, this invention relates to a novel resist stripping composition comprising a mixture of a pyrrolidinone compound and a diethylene gylcol mono-alkyl ether compound and which can also include poly-ethylene glycol and to stripping resists with said stripping compositions.
Background of the Invention Modern technology utilizes positive-type resist materials for lithographically delineating patterns onto a substrate so that the patterns can be subse-quently etched or otherwise defined into the substrate material. The resist material is deposited as a film and the desired pattern is defined by exposing the resist film to energetic radiation. Thereafter the exposed regions are subject to a dissolution by a suitable developer liquid. After the pattern has been thus defined in the substrate the resist material must be completely removed from the substrate to avoid adversely affecting or hindering subsequent operations or processing steps.
It is necessary in such a photolithographic pro-cess that the photoresist material, following pattern ~k s-1185 c-l 1179S8~
delineation, be evenly and completely removed from all unexposed areas so as to permit further lithographic operations.
Even the partial remains of a resist in an area to be further patterned is undesirable. Also, undesired resist residues between patterned lines can have deleterious effects or subsequent processes, such as metallization, or cause undesirable surface states and charges.
Heretofore the resist materials have been removed by stripping agents containing one or more of the following: halogenated hydrocarbons, for example, methylene chloride or tetrachloroethylene; amines and their derivatives such as dimethyl~ormamide, N-methyl-
AND METHODS OF STRIPPING RESI~TS
Field of the Invention This invention relates to novel resist stripping compositions and to methods of stripping resists em-ploying said stripping compositions. More particu-larly, this invention relates to a novel resist stripping composition comprising a mixture of a pyrrolidinone compound and a diethylene gylcol mono-alkyl ether compound and which can also include poly-ethylene glycol and to stripping resists with said stripping compositions.
Background of the Invention Modern technology utilizes positive-type resist materials for lithographically delineating patterns onto a substrate so that the patterns can be subse-quently etched or otherwise defined into the substrate material. The resist material is deposited as a film and the desired pattern is defined by exposing the resist film to energetic radiation. Thereafter the exposed regions are subject to a dissolution by a suitable developer liquid. After the pattern has been thus defined in the substrate the resist material must be completely removed from the substrate to avoid adversely affecting or hindering subsequent operations or processing steps.
It is necessary in such a photolithographic pro-cess that the photoresist material, following pattern ~k s-1185 c-l 1179S8~
delineation, be evenly and completely removed from all unexposed areas so as to permit further lithographic operations.
Even the partial remains of a resist in an area to be further patterned is undesirable. Also, undesired resist residues between patterned lines can have deleterious effects or subsequent processes, such as metallization, or cause undesirable surface states and charges.
Heretofore the resist materials have been removed by stripping agents containing one or more of the following: halogenated hydrocarbons, for example, methylene chloride or tetrachloroethylene; amines and their derivatives such as dimethyl~ormamide, N-methyl-
2-pyrrolidone, diethanolamine and triethanolamine;
glycol ethers such as ethylene glycol monoethyl ether, 2-butoxyethanol, 2-(2-butoxyethoxy)ethanol, and the acetates thereof; ketones such as methyl ethyl ketone, acetone, methyl isobutyl ketone and cyclohexanone, as well as such materials as dioxane, sodium phenolate, isopropyl alcohol, sulfuric acid/nitric acid mixtures, persulfuric acid mixtures such as Caro's acid and sul-furic acid ammonium persulfate, and mixtures of caus-tic and phenol derivatives as well as various other materials.
However, there are various and numerous draw-backs and disadvantages with these various materials.
Among the one or more drawbacks and disadvantages found in the use of each such stripping agents there may be mentioned the following: undesirable flamma-bility, volatility, odor and toxicity; incomplete s-1185 C-l ~L17958~
removal of all resist film; effectiveness only on certain resist films; attack of components other than the resist material, such as attack of the metal substrates by the stripping agent; safety in handling and disposal of the stripper; and the undesired neces-sity for use at specified elevated temperatures when selected resists are being stripped. Furthermore, the limited stripping capabilities of the stripping agents is a very decided drawback. Additionally many such strippers are not sufficiently effective against resist materials that are subject to a severe post-baking operation thereby limiting their usefulness.
In some of the strippers the presence of water is extremely detrimental. Additionally, for those lS stripping applications requiring inertness of the agent to metal substrates, toxicity during handling and difficulty of disposal are primary drawbacks.
Summary of the Invention It has now been found that a suitable photoresist stripping composition in which the hereinbefore men-tioned disadvantages and drawbacks are eliminated or substantially reduced and in which the range of use-fulness of the stripping composition is greatly extended can be obtained in accordance with the teach-ings of the present invention. The novel stripping compositions also exhibit a synergistically enhanced stripping action and provide resist stripping capabil-ities not possible from the use of the individual components used alone as photoresist strippers. The novel stripping compositions of this invention com-prise a mixture of from about 55 to about 80 percent - B-1185 C-l 11'~9581 by weight of a 2-pyrrolidinone compound and from about 20 to about 45 percent by weight of a diethylene gly-col monoalkyl ether compound.
Even more effective stripping compositions are provided if there is added to the basic misture from about 3 to about 30 percent by weight of polyethylene glycol. The presence of water in the stripping . .
compositions of this invention is not detrimental and can be present in an amount of from about 0 to about 10 percent by weight without undue adverse effects resulting.
The invention also relates to the use of such stripping compositions for removing photoresist material from a substrate surface.
Detailed Description of the Invention The stripping compositions of this invention com-prise stripping compositions containing from about 55 to about 80 weight percent, preferably from about 60 to about 75 weight percent, and most preferably about 73 weight percent a 2-pyrrolidinone compound of the formula ~0 wherein R is selected from the group consisting of hydrogen, alkyl of 1 to 3 carbon atoms and hydroxyalkyl of 1 to 3 carbon atoms, and from about 20 to about 45 weight percent, preferably about 25 to about 40 weight percent, and most preferably about 27 s-1185 C-l 11'795~31 weight percent of a diethylene glycol monoalkyl ether of the formula HOCH2cH2_o_cH2cH2_o_Rl wherein Rl is alkyl of 1 to 4 carbon atoms.
As examples of 2-pyrrolidinone compounds suitable for use in this invention three may be mentioned, for example, 2-pyrrolidinone, 1-methyl-2-pyrrolidinone, 1-ethyl-2-pyrrolidinone, 1-propyl-2-pyrrolidinone, 1-hydroxymethyl-2-pyrrolidinone, 1-hydroxyethyl-2-pyrrolidinone, and 1-hydroxypropyl-2-pyrrolidinone.
Especially preferred is l-methyl-2-pyrrolidinone.
As examples of diethylene glycol monoalkyl ether compounds suitable for use in this invention there may be mentioned, for example, 2-(methoxyethoxy)ethanol, 2-(ethoxyethoxy)ethanol, 2-(2-propoxyethoxy)ethanol and 2-(butoxyethoxy)ethanol. Especially preferred is 2-(2-ethoxyethoxy)ethanol.
An even more effective and desirable stripping composition is provided when from about 3 to about 30 weight percent, preferably about 5 to about 25 weight percent, and most preferably about 6 to about 15 weight percent polyethylene glycol is added to the aforementioned stripping mixture.
A most preferred stripping composition of this invention comprises a mixture of from about 50%
l-methyl-2-pyrrolidinone, about 25~ 2-(2-ethoxyethoxy) ethanol and about 25% polyethylene glycol.
While the compositions of this invention can be free of water this is not essential and water can be present in an amount of up to about 10 percent by weight.
B-1185 C-l 11'7958i As exemplary stripping compositions of this invention there can be mentioned the following compositions of Table I.
Table I
Percents by Weight Composition Component A B C D E F' G
l-methyl-2-pyrrolidinone 50 70 70 -- -- -- --2-(2-ethoxyethoxy) ethanol 25 25 24 30 30 -- --polyethylene glycol 25 -- 6 -- -- -- --water -- 5 -- -- -- -- --pyrrolidinone -- -- -- 70 -- 70 --2-(2-butoxyethoxy) ethanol -- -- -- -- -- -- 30 l-ethyl-2-pyrrolidinone -- -- -- -- 70 -- 70 2-~2-methoxyethoxy) ethanol -- -- -- -- -- 30 --In the compositions of this invention any suit-able polyethylene glycol may be employed although polyethylene glycol of a molecular weight of about 200 is preferred.
The stripping compositions of this invention are effective in stripping a wide and varied range of positive photoresists. Most positive photoresists consist of an ortho napthoquinone diazide sulfonic acid ester or amide sensitizer or photoactive compon-ent, with novolak, resole, polyacrylamide or acrylic copolymer type binders or resins. Such positive photoresists are well known in the art. Such resists and sensitizers are described, for example, in United States Pat~nt Nos. 3,046,118; ~,046,121; 3,106,465;
glycol ethers such as ethylene glycol monoethyl ether, 2-butoxyethanol, 2-(2-butoxyethoxy)ethanol, and the acetates thereof; ketones such as methyl ethyl ketone, acetone, methyl isobutyl ketone and cyclohexanone, as well as such materials as dioxane, sodium phenolate, isopropyl alcohol, sulfuric acid/nitric acid mixtures, persulfuric acid mixtures such as Caro's acid and sul-furic acid ammonium persulfate, and mixtures of caus-tic and phenol derivatives as well as various other materials.
However, there are various and numerous draw-backs and disadvantages with these various materials.
Among the one or more drawbacks and disadvantages found in the use of each such stripping agents there may be mentioned the following: undesirable flamma-bility, volatility, odor and toxicity; incomplete s-1185 C-l ~L17958~
removal of all resist film; effectiveness only on certain resist films; attack of components other than the resist material, such as attack of the metal substrates by the stripping agent; safety in handling and disposal of the stripper; and the undesired neces-sity for use at specified elevated temperatures when selected resists are being stripped. Furthermore, the limited stripping capabilities of the stripping agents is a very decided drawback. Additionally many such strippers are not sufficiently effective against resist materials that are subject to a severe post-baking operation thereby limiting their usefulness.
In some of the strippers the presence of water is extremely detrimental. Additionally, for those lS stripping applications requiring inertness of the agent to metal substrates, toxicity during handling and difficulty of disposal are primary drawbacks.
Summary of the Invention It has now been found that a suitable photoresist stripping composition in which the hereinbefore men-tioned disadvantages and drawbacks are eliminated or substantially reduced and in which the range of use-fulness of the stripping composition is greatly extended can be obtained in accordance with the teach-ings of the present invention. The novel stripping compositions also exhibit a synergistically enhanced stripping action and provide resist stripping capabil-ities not possible from the use of the individual components used alone as photoresist strippers. The novel stripping compositions of this invention com-prise a mixture of from about 55 to about 80 percent - B-1185 C-l 11'~9581 by weight of a 2-pyrrolidinone compound and from about 20 to about 45 percent by weight of a diethylene gly-col monoalkyl ether compound.
Even more effective stripping compositions are provided if there is added to the basic misture from about 3 to about 30 percent by weight of polyethylene glycol. The presence of water in the stripping . .
compositions of this invention is not detrimental and can be present in an amount of from about 0 to about 10 percent by weight without undue adverse effects resulting.
The invention also relates to the use of such stripping compositions for removing photoresist material from a substrate surface.
Detailed Description of the Invention The stripping compositions of this invention com-prise stripping compositions containing from about 55 to about 80 weight percent, preferably from about 60 to about 75 weight percent, and most preferably about 73 weight percent a 2-pyrrolidinone compound of the formula ~0 wherein R is selected from the group consisting of hydrogen, alkyl of 1 to 3 carbon atoms and hydroxyalkyl of 1 to 3 carbon atoms, and from about 20 to about 45 weight percent, preferably about 25 to about 40 weight percent, and most preferably about 27 s-1185 C-l 11'795~31 weight percent of a diethylene glycol monoalkyl ether of the formula HOCH2cH2_o_cH2cH2_o_Rl wherein Rl is alkyl of 1 to 4 carbon atoms.
As examples of 2-pyrrolidinone compounds suitable for use in this invention three may be mentioned, for example, 2-pyrrolidinone, 1-methyl-2-pyrrolidinone, 1-ethyl-2-pyrrolidinone, 1-propyl-2-pyrrolidinone, 1-hydroxymethyl-2-pyrrolidinone, 1-hydroxyethyl-2-pyrrolidinone, and 1-hydroxypropyl-2-pyrrolidinone.
Especially preferred is l-methyl-2-pyrrolidinone.
As examples of diethylene glycol monoalkyl ether compounds suitable for use in this invention there may be mentioned, for example, 2-(methoxyethoxy)ethanol, 2-(ethoxyethoxy)ethanol, 2-(2-propoxyethoxy)ethanol and 2-(butoxyethoxy)ethanol. Especially preferred is 2-(2-ethoxyethoxy)ethanol.
An even more effective and desirable stripping composition is provided when from about 3 to about 30 weight percent, preferably about 5 to about 25 weight percent, and most preferably about 6 to about 15 weight percent polyethylene glycol is added to the aforementioned stripping mixture.
A most preferred stripping composition of this invention comprises a mixture of from about 50%
l-methyl-2-pyrrolidinone, about 25~ 2-(2-ethoxyethoxy) ethanol and about 25% polyethylene glycol.
While the compositions of this invention can be free of water this is not essential and water can be present in an amount of up to about 10 percent by weight.
B-1185 C-l 11'7958i As exemplary stripping compositions of this invention there can be mentioned the following compositions of Table I.
Table I
Percents by Weight Composition Component A B C D E F' G
l-methyl-2-pyrrolidinone 50 70 70 -- -- -- --2-(2-ethoxyethoxy) ethanol 25 25 24 30 30 -- --polyethylene glycol 25 -- 6 -- -- -- --water -- 5 -- -- -- -- --pyrrolidinone -- -- -- 70 -- 70 --2-(2-butoxyethoxy) ethanol -- -- -- -- -- -- 30 l-ethyl-2-pyrrolidinone -- -- -- -- 70 -- 70 2-~2-methoxyethoxy) ethanol -- -- -- -- -- 30 --In the compositions of this invention any suit-able polyethylene glycol may be employed although polyethylene glycol of a molecular weight of about 200 is preferred.
The stripping compositions of this invention are effective in stripping a wide and varied range of positive photoresists. Most positive photoresists consist of an ortho napthoquinone diazide sulfonic acid ester or amide sensitizer or photoactive compon-ent, with novolak, resole, polyacrylamide or acrylic copolymer type binders or resins. Such positive photoresists are well known in the art. Such resists and sensitizers are described, for example, in United States Pat~nt Nos. 3,046,118; ~,046,121; 3,106,465;
3,201,239; 3,538,137; 3,666,q73; 3,934,057; 3,984,582 and 4,007,047. As examples of such positive photo-resist compositions for which the stripping cornposi-tions of this invention may be used there may be men-tioned Eastman Kodak Company photoresist Kodak 809;
J. T. Baker Chemical Company photoresist PR-20;
Philip A. Hunt Chemical Corp. Waycoat HPR 104, HPR
* * *
106, HPR 204 and HPR 206 photoresists; Shipley Company * * *
Inc. photoresists AZ-1350, AZ-1350B, AZ-1350H, AZ-* * * * * *
1350J, AZ-1370, AZ-1450~3, AZ-1450J, AZ-1470, AZ-2400 and AZ-lll; Polychrome Corporation photoresists PC-* * *
129, PC-129SF and PC-13)3; Fuji Chemicals Industrial Co. photoresist FFPR-200; and Tokyo Ohka Kogyo Co.
Ltd. photoresist OFPR-800.
The stripping compositions of this invention are effective in removing photoresist materials from substrates even when they have been subjected to a post-bake treatment at about 150C for a period of about one hour.
The stripping compositions of this invention are especially advantageous for numerous reasons among which may be mentioned the following. The stripping compositions remove positive photoresist materials from metal and other substrates without attacking the substrate. The compositions are essentially non-toxic and are water miscible. The presence of water during the stripping operation is not deleterious to the operation of the stripping composition. Unlike phenolic based strippers ~he compositions of this invention require no special handling and are * Trade Mark ' B-1185 C-l 117~581 easily disposed of in normal sewage treatment facili-ties. Moreover the bath life and stripping effective-ness of the compositions are for the most part inde-pendent of temperature. Use of the stripping composi-tions of this invention requires only a subsequent rinse with deionized water whereas many prior strip-pers require the use of additional organic solvents.
The stripping compositions of this invention complete-ly remove difficult-to-remove positive photoresists at about 75C or less whereas some prior art strippers require both temperatures of about 95 to 100C. Also, most positive photoresists are completely stripped in about one minute or less while stripping times of 5 to 20 minutes are recommended for many commercial strip-ping compositions.
Additionally, although l-methyl-2-pyrrolidinone itself has been suggested as a stripping agent for certain positive photoresists, said compound is not an effective stripper for various positive photoresists.
It has been unexpectedly found that the stripping compositions of this invention effectively and com-pletely remove positive photoresist material from substrates which photoresist materials are not effec-tively and completely removed by the individual compo-nents of the compositions of this invention. The effectiveness and unexpected nature of the stripping action of stripping composition of this invention is illustrated by the data presented in the following Table II.
Wafer substrates were coated with positive photo-resist materials according to art recognized proce-,_~ B-1185 C-l 11'i~9S8~
dures and post-baked at about 150C for a period of about ~5 minutes to one hour. Stripping baths were maintained at constant temperature with water baths and the post-baked coated wafers were immersed into 600 ml beakers containing the constant temperature stripping compositions with intermittent agitation for the specified times after which the wafer is removed, rinsed in running deionized water and spin dried at 3000 rpm. Strippability was judged by inspection of the wafers to ascertain if any residue was present.
Compositions of this invention, denoted as Compo-sitions A through G, which correspond in composition to those so designated in Table I, are compared to results obtained for the individual components alone for three generally difficult-to-remove photoresists namely Shipley's AZ-1350J photoresist, Tokyo Ohka Kogyo Co. Ltd.'s OFPR-800 photoresist and Fuji's FPPR-200 photoresist.
-~ B-1185 C-l 11'~9S81 Table II
Temperature C, Time and % Removal Stripping AZ-1350J OFPR-800 FPPR-200 Composition Photoresist Photoresist Photoresist 1-methyl-2- 75,10 min., 75,~4.5 min., 25,~2 min., pyrrolidinone ~60% ~ 75% C 75 polyethylene 75,6.5min., 75,5 min., glycol 200 ~60% ~50%
2-(2-ethoxy- 75,6 min., 75,~5 min., ethoxy) ~ 60~ ~20%
ethanol pyrrolidinone 75,10 min., 100%
2-(2-butoxy- 75,10 min., lS ethoxy) 50%
ethanol l-ethyl-2- 75,5 1/2 min., pyrrolidinone 100%
2-(2-methoxy- 75,12 min., ethoxy) 60%
ethanol A 75,10 min., 75,22 min., 25,~55 sec., 70% 100% 100%
B 75,~1 min., 75,6 min., 25,6 min., 100% 75% 85%
C 75,~3 min., 99%
D 75,8 1/2 min., 100%
E 75,4 1/2 min., 100%
F 75,5 1/2 min., 100%
G 75,5 1/2 min., 100%
~-1185 C-l 11'~958~
The above examples are given merely by way of illustration and are not to be considered to limit the invention.
It is anticipated that the stripping compositions of this invention can be used as stripping agents for positive photoresists by contacting the unexposed photoresist on a substrate with the stripping compositions in a variety of means, such as by immersion in a stripping bath or by spraying the stripping composition over the surface of the unexposed photoresist.
While the use of the above compositions for stripping photoresist materials from substrates has alone been illustrated it wil]. be appreciated that the stripping compositions of the invention are suitable for other uses which will be apparent to those skilled in the art, such as, for example, in the stripping of polymer residues from reaction or curing vessels and the like, or for stripping coatings, such as, for example, paints and varnishes and the like, from surfaces.
J. T. Baker Chemical Company photoresist PR-20;
Philip A. Hunt Chemical Corp. Waycoat HPR 104, HPR
* * *
106, HPR 204 and HPR 206 photoresists; Shipley Company * * *
Inc. photoresists AZ-1350, AZ-1350B, AZ-1350H, AZ-* * * * * *
1350J, AZ-1370, AZ-1450~3, AZ-1450J, AZ-1470, AZ-2400 and AZ-lll; Polychrome Corporation photoresists PC-* * *
129, PC-129SF and PC-13)3; Fuji Chemicals Industrial Co. photoresist FFPR-200; and Tokyo Ohka Kogyo Co.
Ltd. photoresist OFPR-800.
The stripping compositions of this invention are effective in removing photoresist materials from substrates even when they have been subjected to a post-bake treatment at about 150C for a period of about one hour.
The stripping compositions of this invention are especially advantageous for numerous reasons among which may be mentioned the following. The stripping compositions remove positive photoresist materials from metal and other substrates without attacking the substrate. The compositions are essentially non-toxic and are water miscible. The presence of water during the stripping operation is not deleterious to the operation of the stripping composition. Unlike phenolic based strippers ~he compositions of this invention require no special handling and are * Trade Mark ' B-1185 C-l 117~581 easily disposed of in normal sewage treatment facili-ties. Moreover the bath life and stripping effective-ness of the compositions are for the most part inde-pendent of temperature. Use of the stripping composi-tions of this invention requires only a subsequent rinse with deionized water whereas many prior strip-pers require the use of additional organic solvents.
The stripping compositions of this invention complete-ly remove difficult-to-remove positive photoresists at about 75C or less whereas some prior art strippers require both temperatures of about 95 to 100C. Also, most positive photoresists are completely stripped in about one minute or less while stripping times of 5 to 20 minutes are recommended for many commercial strip-ping compositions.
Additionally, although l-methyl-2-pyrrolidinone itself has been suggested as a stripping agent for certain positive photoresists, said compound is not an effective stripper for various positive photoresists.
It has been unexpectedly found that the stripping compositions of this invention effectively and com-pletely remove positive photoresist material from substrates which photoresist materials are not effec-tively and completely removed by the individual compo-nents of the compositions of this invention. The effectiveness and unexpected nature of the stripping action of stripping composition of this invention is illustrated by the data presented in the following Table II.
Wafer substrates were coated with positive photo-resist materials according to art recognized proce-,_~ B-1185 C-l 11'i~9S8~
dures and post-baked at about 150C for a period of about ~5 minutes to one hour. Stripping baths were maintained at constant temperature with water baths and the post-baked coated wafers were immersed into 600 ml beakers containing the constant temperature stripping compositions with intermittent agitation for the specified times after which the wafer is removed, rinsed in running deionized water and spin dried at 3000 rpm. Strippability was judged by inspection of the wafers to ascertain if any residue was present.
Compositions of this invention, denoted as Compo-sitions A through G, which correspond in composition to those so designated in Table I, are compared to results obtained for the individual components alone for three generally difficult-to-remove photoresists namely Shipley's AZ-1350J photoresist, Tokyo Ohka Kogyo Co. Ltd.'s OFPR-800 photoresist and Fuji's FPPR-200 photoresist.
-~ B-1185 C-l 11'~9S81 Table II
Temperature C, Time and % Removal Stripping AZ-1350J OFPR-800 FPPR-200 Composition Photoresist Photoresist Photoresist 1-methyl-2- 75,10 min., 75,~4.5 min., 25,~2 min., pyrrolidinone ~60% ~ 75% C 75 polyethylene 75,6.5min., 75,5 min., glycol 200 ~60% ~50%
2-(2-ethoxy- 75,6 min., 75,~5 min., ethoxy) ~ 60~ ~20%
ethanol pyrrolidinone 75,10 min., 100%
2-(2-butoxy- 75,10 min., lS ethoxy) 50%
ethanol l-ethyl-2- 75,5 1/2 min., pyrrolidinone 100%
2-(2-methoxy- 75,12 min., ethoxy) 60%
ethanol A 75,10 min., 75,22 min., 25,~55 sec., 70% 100% 100%
B 75,~1 min., 75,6 min., 25,6 min., 100% 75% 85%
C 75,~3 min., 99%
D 75,8 1/2 min., 100%
E 75,4 1/2 min., 100%
F 75,5 1/2 min., 100%
G 75,5 1/2 min., 100%
~-1185 C-l 11'~958~
The above examples are given merely by way of illustration and are not to be considered to limit the invention.
It is anticipated that the stripping compositions of this invention can be used as stripping agents for positive photoresists by contacting the unexposed photoresist on a substrate with the stripping compositions in a variety of means, such as by immersion in a stripping bath or by spraying the stripping composition over the surface of the unexposed photoresist.
While the use of the above compositions for stripping photoresist materials from substrates has alone been illustrated it wil]. be appreciated that the stripping compositions of the invention are suitable for other uses which will be apparent to those skilled in the art, such as, for example, in the stripping of polymer residues from reaction or curing vessels and the like, or for stripping coatings, such as, for example, paints and varnishes and the like, from surfaces.
Claims (20)
1. A stripping composition comprising from about 55 to about 80 weight percent of a 2-pyrrolidinone compound of the formula wherein R is selected from the group consisting of hydrogen, alkyl of 1 to 3 carbon atoms and hydroxyalkyl of 1 to 3 carbon atoms, from about 20 to about 45 weight percent of diethylene glycol monoalkylether of the formula HOCH2CH2-O-CH2CH2-O-R1 wherein R1 is alkyl of 1 to 4 carbon atoms, and from about 5 to about 25 weight percent polyethyl-ene glycol.
2. A composition of claim 1, comprising from about 55 to about 80 weight percent 1-methyl-2-pyrrol-idinone, from about 20 to about 45 weight percent 2-(2-ethoxyethoxy)ethanol and from about 5 to about 25 weight percent polyethylene glycol.
3. A composition of claim 2, comprising about 60 to 75% 1-methyl-2-pyrrolidinone, 25 to 40% 2-(2-ethoxyethoxy)ethanol and 6 to 15 percent polyethylene glycol.
4. A composition of claim 2, comprising about 50% 1-methyl-2-pyrrolidinone, about 25% 2-(2-ethoxy-ethoxy)ethanol and about 25% polyethylene glycol.
5. A composition of claim 2, comprising about 70%
1-methyl-2-pyrrolidinone, about 24% 2-(2-e-thoxyethoxy)-ethanol and about 6% polyethylene glycol.
1-methyl-2-pyrrolidinone, about 24% 2-(2-e-thoxyethoxy)-ethanol and about 6% polyethylene glycol.
6. The composition of claim 1, wherein the poly-ethylene glycol is polyethylene glycol of molecular weight of about 200.
7. The composition of claim 2, wherein the poly-ethylene glycol is polyethylene glycol of molecular weight of about 200.
8. The composition of claim 3, wherein the poly-ethylene glycol is polyethylene glycol of molecular weight of about 200.
9. The composition of claim 4, wherein the poly-ethylene glycol is polyethylene glycol of molecular weight of about 200.
10. The composition of claim 5, wherein the poly-ethylene glycol is polyethylene glycol of molecular weight of about 200.
11. A method wherein unexposed photoresist is stripped from a substrate by contacting the unexposed photoresist with a stripping composition, the improvement comprising utilizing as the stripping composition the composition of claim 1.
12. A method wherein unexposed photoresist is stripped from a substrate by contacting the unexposed photoresist with a stripping composition, the improvement comprising utilizing as the stripping composition the composition of claim 2.
13. A method wherein unexposed photoresist is stripped from a substrate by contacting the unexposed photo-resist with a stripping composition, the improvement com-prising utilizing as the stripping composition the compo-sition of claim 3.
14. A method wherein unexposed photoresist is stripped from a substrate by contacting the unexposed photo-resist with a stripping composition, the improvement comprising utilizing as the stripping composition the com-position of claim 4.
15. A method wherein unexposed photoresist is stripped from a substrate by contacting the unexposed photoresist with a stripping composition, the improvement comprising utilizing as the stripping composition the com-position of claim 5.
16. A method wherein unexposed photoresist is stripped from a substrate by contacting the unexposed photoresist with a stripping composition, the improvement comprising utilizing as the stripping composition the com-position of claim 6.
17. A method wherein unexposed photoresist is stripped from a substrate by contacting the unexposed photo-resist with a stripping composition, the improvement comprising utilizing as the stripping composition the com-position of claim 7.
18. A method wherein unexposed photoresist is stripped from a substrate by contacting the unexposed photo-resist with a stripping composition, the improvement com-prising utilizing as the stripping composition the com-position of claim 8.
19. A method wherein unexposed photoresist is stripped from a substrate by contacting the unexposed photoresist with a stripping composition, the improvement comprising utilizing as the stripping composition the composition of claim 9.
20. A method wherein unexposed photoresist is stripped from a substrate by contacting the unexposed photo-resist with a stripping composition, the improvement comprising utilizing as the stripping composition the com-position of claim 10.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30478981A | 1981-09-23 | 1981-09-23 | |
| US304,789 | 1981-09-23 | ||
| US40885282A | 1982-08-17 | 1982-08-17 | |
| US408,852 | 1989-09-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1179581A true CA1179581A (en) | 1984-12-18 |
Family
ID=26974227
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000410275A Expired CA1179581A (en) | 1981-09-23 | 1982-08-27 | Stripping compositions and method of stripping resists |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA1179581A (en) |
-
1982
- 1982-08-27 CA CA000410275A patent/CA1179581A/en not_active Expired
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