CA1279561C - Solvents for photoresist removal - Google Patents
Solvents for photoresist removalInfo
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- CA1279561C CA1279561C CA000520952A CA520952A CA1279561C CA 1279561 C CA1279561 C CA 1279561C CA 000520952 A CA000520952 A CA 000520952A CA 520952 A CA520952 A CA 520952A CA 1279561 C CA1279561 C CA 1279561C
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Abstract
ABSTRACT OF THE DISCLOSURE
The invention relates to solvent systems which are based on water-soluble amino derivatives and propy-lene glycol components, for removing photoresists. These solvent systems are comprised of (a) from about 10 to 100% by weight of at least one water-soluble amine of the general formula in which R1, R2, R3, R4 denote H or alkyl groups n,m denote 0 to 2, and o denotes 1 to 3; and (b) from about 0 to 90% by weight of at least one water-soluble propylene glycol derivative of the general formula
The invention relates to solvent systems which are based on water-soluble amino derivatives and propy-lene glycol components, for removing photoresists. These solvent systems are comprised of (a) from about 10 to 100% by weight of at least one water-soluble amine of the general formula in which R1, R2, R3, R4 denote H or alkyl groups n,m denote 0 to 2, and o denotes 1 to 3; and (b) from about 0 to 90% by weight of at least one water-soluble propylene glycol derivative of the general formula
Description
1;~7~5g~i1 SOLVENTS FOR PHOTORESIST REMOVAL
BACKGROUND OF THE INVENTION
The present invention relates to novel solvent systems, based on water-soluble amino derivatives and propylene glycol compounds, that are useful for removing photoresists.
Photoresists are used as masks in the production of, via etching or implantation processes, integrated component parts, circuit boards, and the like. Aster having served their purposes, the masks are generally removed, frequently by means of agents which, depending on their mode of action, are known as "strippers" or "removers".
Systems of this kind are described, for example, by W.S. de Forest in "Photoresist: Materials and Processes" pages 203 _ seq., McGraw-Hill Book Co., New York, 1975. They contain, e.g., chlorinated hydrocar-bons, such as methylenechloride; polar solvents, such as dimethylformamide, N-methyl-2-pyrrolidone and monoetha-nolamine; glycol ethers, such as ethylene glycol mono-ethyl ether, ethylene glycol monobutyl ether and the ace-tates thereof; strong bases, such as tetramethyl ammonium hydroxide; and strong acids, such as sulfuric acid/H202 mixtures.
U.S. Patent No. 3,673,099 describes a mixture of N-methyl-2-pyrrolidone and a strong base, such as tetra-1;~ '7~
methyl ammonium hydroxide. It ls known that mixtures of this type attack sensitive substratesr such as aluminum layers, when water is added. It is, however, desirable for a product to be suitable for removing photoresist coatings both from sensitive and less sensitive substrate layers, since quite frequently these two types of substrate layers are used simultaneously. Moreover, tetramethyl ammonium hydroxide easily decomposes when heated, and thus the stripping solution has a very short service life at elevated temperatures.
U.S. Patent No. 3,796,602 describes a system comprising an organic solvent which is partially misceable with water.
However, the compounds mentioned in this publication, such as ethylene glycol monobutyl ether and monoaminoethanol, present ; toxicological problems. Furthermore, these compounds evaporate easily due to their low boiling points and, hence, cannot be employed at elevated temperatures.
European Patent Application No. 0 075 329 published March 30, 1983 describes a mixture of a derivative of 2-pyrrolidone and a diethylene glycol monoalkyl ether. Compounds ofthis kind are, however, hardly effective in their action. In the examples of the document, for instance, a stripper bath temperature of 75C is required for removal of a photoresist sub~ected to a post-bake treatment at about 150C.
European Patent Application No. 0 145 973 published June 26, 1985 describes a system of a piperazine derivative and a N-alkyl-2-pyrrolidone. The preferably employed N-aminoethyl ~;~79561 piperazine is classified as being toxic, whereas n-hydroxyethyl piperazine is scarcely effective.
SUMMARY OF THE INVENTION
It is therefore an object of the present invention to provide an agent for photoresist removal that can -2a-1~79561 be used at low temperatures and at elevated temperatures, that does not cause toxic problems, that can be rinsed off with water and is completely, or at least largely, non-corrosive of sensitive substrates.
In accomplishing the foregoing object, there has been provided, in accordance with one aspect of the pre-sent invention, an agent for photoresist removal that is comprised of:
(a) 10 to 100% by weight of at least one water-soluble amine represented by the formula l R3 H2N ~[(C)n - (C)m - O,~H]oH
in which Rl, R2, R3, R4 denote ~ or alkyl groups n,m denote 0 to 2, and o denotes 1 to 3;
and (b) 0 to 90% by weight of at least one water-soluble propylene glycol derivative represented by the formula R3 - O - [CH2 - CH - O]p - R4 in which R3, R4 denote H, alkyl or C-alkyl groups, and o P denotes 1 to 3.
1;~795~1 Other objects, features and advantages of the present invention will become apparent from the following detailed description. It should be understood, however, that the detailed description and specific examples, while indicating preferred embodiments of the invention, are given by way of illustration only, since various changes and modifications within the spirit and scope of the invention will become apparent to those skilled in the art from this detailed description.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
The solvent systems of the present invention are suitable for removing both positive-working resists and photopolymerizable resists. Resists which can be deve-loped with aqueous-alkaline solutions are preferably removed.
It has been found that mixtures made according to the instant invention, comprising water-soluble propy-lene glycol ethers and amino compounds, can be used as agents for photoresist removal, and do not exhibit the disadvantages of the prior art cited above. Preference is given to mixtures which, due to the high boiling tem-peratures (at least 180C) of the individual components, result in only slight weight losses when the agent is used at elevated temperatures over a prolonged period of time. A mixture of N-(2-amino-ethyl)ethanolamine and tripropylene glycol methyl ether is particularly pre-ferred.
It was not foreseeable that the photoresist remover of the present invention, comprising high-boiling propylene glycol ether derivatives such as tripropylene glycol methyl ether, would exhibit satisfactory proper-ties even at room temperature. Thus, it is possible to use the remover of the present invention to particular advantage for the purposes of the invention, since it can ~;~7~561 be employed effectively at room temperature and, due to its favorable evaporation characteristics, at elevated bath temperatures as well.
It has also been found that the particularly preferred mixture of tripropylene glycol methyl ether and N-(2-aminoethyl)-ethanolamine has a synergetic effect.
Since, in practice, photoresist layers which were not exposed to high temperatures have to be removed quite frequently, mixtures whose individual components have boiling points of 160C or higher are also pre-ferable. Of these, mixtures of dipropylene glycol methyl ether and isopropanolamine are particularly preferred.
These systems, too, exhibit the advantages described above, i.e., they can be used at room temperature and at elevated temperatures. Due to their higher evaporation rates, however, these removers are preferably employed at relatively low bath temperatures, and they have a synergetic effect.
It is true that the propylene glycol ethers, such as dipropylene glycol methyl ether or tripropylene glycol methyl ether which are preferably employed within this invention, are distinctly more hydrophobic than com-parable ethylene glycol ether products, and hence they possess good solubilizing properties with respect to organic polymers. Nevertheless, the compounds used in the present invention can be easily rinsed off with water without leaving any residues.
Despite their high efficiency, the mixtures according to the present invention do not corrode sen-sitive substrates, such as aluminum layers.
Mixtures containing lO to 90% by weight, and in particular 20 to 70% by weight, bf the amine and lO to 90%
by weight, and in particular 30 to 80% by weight, of the propylene glycol derivative, are preferred. It is par-ticularly preferred that these ratios be employed with isopropanolamine and/or N-(2-amino-ethyl)ethanolamine and ~795~
di- or tripropylene glycol methyl ether.
Apart from their low toxicity, the mentioned systems exhibit the advantage of having only a very faint odor, so that it is, for example, also possible to use them in uncovered baths.
It is self-evident that mixtures of one or several amines with one or several propylene glycol deri-vatives also come within the scope of the present inven-tion.
Although it is customary to remove photoresists in an immersion process, whereby the substrates carrying photoresist coatings are usually moved in a bath or, alternatively, the bath is moved, for example, by means of a circulation pump, the remover solutions of the pre-sent invention are also suitable for use in other pro-cesses, such as spray or puddle processes.
The present invention will now be explained in greater detail by references to the following, non-limiting examples.
Examples 1 to 5 To test the effectiveness of the remover, pho-toresist coatings conventionally employed in the produc-tion of integrated circuits were used. A commercially available photoresist on a diazoquinone/novolak basis (AZ 1350 J) was spin-coated onto silicon wafers at 4,000 rpm and dried at 90C for 30 minutes. A coating thickness of 1.8 ~m was measured. Subsequently, the substrates were baked at 200~C for 30 minutes.
The removal tests were performed in a moving bath having a temperature of 80C. After a dwell time of minutes in the bath, the wafers were rinsed with deionized water and the remaining thickness of the resist coating was measured. The results, which are compiled in Table 1, clearly show the superior effectiveness of N-(2-aminoethyl)-ethanolamine (AEEA) and isopropanolamine 9~
(IPA), which were employed in accordance with the inven-tion. Triethylene-tetraamine also had a good removing action, but because of its toxicity this compound is not preferred.
The amines used for comparative tests were added in equimolar amounts.
Examples 6 to 12 The following examples also served to test the effectiveness of various amino compounds. Here, too, the compositions were mixed such that equimolar amounts were present in each case.
The test conditions were the same as in Examples 1 to 5, except that the substrates had been baked at 160C for 30 minutes. The bath temperature was 22C, and the dwell time in the remover bath was 10 minutes.
Again, the thickness of the resist coating was measured.
The results shown in Table 2 indicate that even at 22C the removing action of N-(2-amino-ethyl)-ethanol-amine and triethylenetetraamine is superior. Whereas in this case the combination of isopropanolamine and tripro-pylene glycol methyl ether (TPM) is considered less pre-ferable, the mixture of isopropanolamine and dipropylene glycol methyl ether exhibited good properties at room temperature.
Examples 13 to 18 As described in Examples 1 to 5, various mix-tures of N-(2-aminoethyl)-ethanolamine and tripropylene glycol methyl ether were tested. The substrates had been baked at 200C for 30 minutes, and the baths had a tem-perature of 80C.
The results achieved with a bath dwell time of 4 minutes are compiled in Table 3. Under these conditions,-the photoresist coatings were not yet removed completely, but the synergetic effect between N-(2-aminoethyl)-eth-. ~
1~79S61 anolamine and tripropylene glycol methyl ether wasimpressively demonstrated by the measurement of the resist thicknesses of incompletely removed photoresist portions. A mixture comprised of 51% by weight of N-(2-aminoethyl)ethanolamine and 49% by weight of tripro-pylene glycol methyl ether was found to be the optimum composition.
Examples 19 to 21 As described in Examples 13 to 18, the synerge-tic effect between isopropanolamine and dipropylene gly-col methyl ether (DPM) was determined. In these examples, too, the dwell time in the remover bath had been chosen such that measurable resist coatings remained on the substrate.
The results compiled in Table 4 show that an optimum effectiveness is achieved when the mixture is comprised of 22.5% by weight of isopropanolamine and 77.5~ by weight of dipropylene glycol methyl e.her.
Examples 22 and 23 In these examples, the behavior of the removers towards aluminum layers was tested by heating the com-positions corresponding to Examples 13 and 19 to a tem-perature of 80C and allowing them to act on aluminum-coated wafers for 30 minutes. No attack of the aluminum layer was observed.
. Table 1:
.
Example Composition* Thickness of : No. . resist coatinc l 64.4% Di-(n-propylene)-triamine 0.380 ~m 35.6% Tripropylene-glycol-methyl ether (TPM) .
BACKGROUND OF THE INVENTION
The present invention relates to novel solvent systems, based on water-soluble amino derivatives and propylene glycol compounds, that are useful for removing photoresists.
Photoresists are used as masks in the production of, via etching or implantation processes, integrated component parts, circuit boards, and the like. Aster having served their purposes, the masks are generally removed, frequently by means of agents which, depending on their mode of action, are known as "strippers" or "removers".
Systems of this kind are described, for example, by W.S. de Forest in "Photoresist: Materials and Processes" pages 203 _ seq., McGraw-Hill Book Co., New York, 1975. They contain, e.g., chlorinated hydrocar-bons, such as methylenechloride; polar solvents, such as dimethylformamide, N-methyl-2-pyrrolidone and monoetha-nolamine; glycol ethers, such as ethylene glycol mono-ethyl ether, ethylene glycol monobutyl ether and the ace-tates thereof; strong bases, such as tetramethyl ammonium hydroxide; and strong acids, such as sulfuric acid/H202 mixtures.
U.S. Patent No. 3,673,099 describes a mixture of N-methyl-2-pyrrolidone and a strong base, such as tetra-1;~ '7~
methyl ammonium hydroxide. It ls known that mixtures of this type attack sensitive substratesr such as aluminum layers, when water is added. It is, however, desirable for a product to be suitable for removing photoresist coatings both from sensitive and less sensitive substrate layers, since quite frequently these two types of substrate layers are used simultaneously. Moreover, tetramethyl ammonium hydroxide easily decomposes when heated, and thus the stripping solution has a very short service life at elevated temperatures.
U.S. Patent No. 3,796,602 describes a system comprising an organic solvent which is partially misceable with water.
However, the compounds mentioned in this publication, such as ethylene glycol monobutyl ether and monoaminoethanol, present ; toxicological problems. Furthermore, these compounds evaporate easily due to their low boiling points and, hence, cannot be employed at elevated temperatures.
European Patent Application No. 0 075 329 published March 30, 1983 describes a mixture of a derivative of 2-pyrrolidone and a diethylene glycol monoalkyl ether. Compounds ofthis kind are, however, hardly effective in their action. In the examples of the document, for instance, a stripper bath temperature of 75C is required for removal of a photoresist sub~ected to a post-bake treatment at about 150C.
European Patent Application No. 0 145 973 published June 26, 1985 describes a system of a piperazine derivative and a N-alkyl-2-pyrrolidone. The preferably employed N-aminoethyl ~;~79561 piperazine is classified as being toxic, whereas n-hydroxyethyl piperazine is scarcely effective.
SUMMARY OF THE INVENTION
It is therefore an object of the present invention to provide an agent for photoresist removal that can -2a-1~79561 be used at low temperatures and at elevated temperatures, that does not cause toxic problems, that can be rinsed off with water and is completely, or at least largely, non-corrosive of sensitive substrates.
In accomplishing the foregoing object, there has been provided, in accordance with one aspect of the pre-sent invention, an agent for photoresist removal that is comprised of:
(a) 10 to 100% by weight of at least one water-soluble amine represented by the formula l R3 H2N ~[(C)n - (C)m - O,~H]oH
in which Rl, R2, R3, R4 denote ~ or alkyl groups n,m denote 0 to 2, and o denotes 1 to 3;
and (b) 0 to 90% by weight of at least one water-soluble propylene glycol derivative represented by the formula R3 - O - [CH2 - CH - O]p - R4 in which R3, R4 denote H, alkyl or C-alkyl groups, and o P denotes 1 to 3.
1;~795~1 Other objects, features and advantages of the present invention will become apparent from the following detailed description. It should be understood, however, that the detailed description and specific examples, while indicating preferred embodiments of the invention, are given by way of illustration only, since various changes and modifications within the spirit and scope of the invention will become apparent to those skilled in the art from this detailed description.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
The solvent systems of the present invention are suitable for removing both positive-working resists and photopolymerizable resists. Resists which can be deve-loped with aqueous-alkaline solutions are preferably removed.
It has been found that mixtures made according to the instant invention, comprising water-soluble propy-lene glycol ethers and amino compounds, can be used as agents for photoresist removal, and do not exhibit the disadvantages of the prior art cited above. Preference is given to mixtures which, due to the high boiling tem-peratures (at least 180C) of the individual components, result in only slight weight losses when the agent is used at elevated temperatures over a prolonged period of time. A mixture of N-(2-amino-ethyl)ethanolamine and tripropylene glycol methyl ether is particularly pre-ferred.
It was not foreseeable that the photoresist remover of the present invention, comprising high-boiling propylene glycol ether derivatives such as tripropylene glycol methyl ether, would exhibit satisfactory proper-ties even at room temperature. Thus, it is possible to use the remover of the present invention to particular advantage for the purposes of the invention, since it can ~;~7~561 be employed effectively at room temperature and, due to its favorable evaporation characteristics, at elevated bath temperatures as well.
It has also been found that the particularly preferred mixture of tripropylene glycol methyl ether and N-(2-aminoethyl)-ethanolamine has a synergetic effect.
Since, in practice, photoresist layers which were not exposed to high temperatures have to be removed quite frequently, mixtures whose individual components have boiling points of 160C or higher are also pre-ferable. Of these, mixtures of dipropylene glycol methyl ether and isopropanolamine are particularly preferred.
These systems, too, exhibit the advantages described above, i.e., they can be used at room temperature and at elevated temperatures. Due to their higher evaporation rates, however, these removers are preferably employed at relatively low bath temperatures, and they have a synergetic effect.
It is true that the propylene glycol ethers, such as dipropylene glycol methyl ether or tripropylene glycol methyl ether which are preferably employed within this invention, are distinctly more hydrophobic than com-parable ethylene glycol ether products, and hence they possess good solubilizing properties with respect to organic polymers. Nevertheless, the compounds used in the present invention can be easily rinsed off with water without leaving any residues.
Despite their high efficiency, the mixtures according to the present invention do not corrode sen-sitive substrates, such as aluminum layers.
Mixtures containing lO to 90% by weight, and in particular 20 to 70% by weight, bf the amine and lO to 90%
by weight, and in particular 30 to 80% by weight, of the propylene glycol derivative, are preferred. It is par-ticularly preferred that these ratios be employed with isopropanolamine and/or N-(2-amino-ethyl)ethanolamine and ~795~
di- or tripropylene glycol methyl ether.
Apart from their low toxicity, the mentioned systems exhibit the advantage of having only a very faint odor, so that it is, for example, also possible to use them in uncovered baths.
It is self-evident that mixtures of one or several amines with one or several propylene glycol deri-vatives also come within the scope of the present inven-tion.
Although it is customary to remove photoresists in an immersion process, whereby the substrates carrying photoresist coatings are usually moved in a bath or, alternatively, the bath is moved, for example, by means of a circulation pump, the remover solutions of the pre-sent invention are also suitable for use in other pro-cesses, such as spray or puddle processes.
The present invention will now be explained in greater detail by references to the following, non-limiting examples.
Examples 1 to 5 To test the effectiveness of the remover, pho-toresist coatings conventionally employed in the produc-tion of integrated circuits were used. A commercially available photoresist on a diazoquinone/novolak basis (AZ 1350 J) was spin-coated onto silicon wafers at 4,000 rpm and dried at 90C for 30 minutes. A coating thickness of 1.8 ~m was measured. Subsequently, the substrates were baked at 200~C for 30 minutes.
The removal tests were performed in a moving bath having a temperature of 80C. After a dwell time of minutes in the bath, the wafers were rinsed with deionized water and the remaining thickness of the resist coating was measured. The results, which are compiled in Table 1, clearly show the superior effectiveness of N-(2-aminoethyl)-ethanolamine (AEEA) and isopropanolamine 9~
(IPA), which were employed in accordance with the inven-tion. Triethylene-tetraamine also had a good removing action, but because of its toxicity this compound is not preferred.
The amines used for comparative tests were added in equimolar amounts.
Examples 6 to 12 The following examples also served to test the effectiveness of various amino compounds. Here, too, the compositions were mixed such that equimolar amounts were present in each case.
The test conditions were the same as in Examples 1 to 5, except that the substrates had been baked at 160C for 30 minutes. The bath temperature was 22C, and the dwell time in the remover bath was 10 minutes.
Again, the thickness of the resist coating was measured.
The results shown in Table 2 indicate that even at 22C the removing action of N-(2-amino-ethyl)-ethanol-amine and triethylenetetraamine is superior. Whereas in this case the combination of isopropanolamine and tripro-pylene glycol methyl ether (TPM) is considered less pre-ferable, the mixture of isopropanolamine and dipropylene glycol methyl ether exhibited good properties at room temperature.
Examples 13 to 18 As described in Examples 1 to 5, various mix-tures of N-(2-aminoethyl)-ethanolamine and tripropylene glycol methyl ether were tested. The substrates had been baked at 200C for 30 minutes, and the baths had a tem-perature of 80C.
The results achieved with a bath dwell time of 4 minutes are compiled in Table 3. Under these conditions,-the photoresist coatings were not yet removed completely, but the synergetic effect between N-(2-aminoethyl)-eth-. ~
1~79S61 anolamine and tripropylene glycol methyl ether wasimpressively demonstrated by the measurement of the resist thicknesses of incompletely removed photoresist portions. A mixture comprised of 51% by weight of N-(2-aminoethyl)ethanolamine and 49% by weight of tripro-pylene glycol methyl ether was found to be the optimum composition.
Examples 19 to 21 As described in Examples 13 to 18, the synerge-tic effect between isopropanolamine and dipropylene gly-col methyl ether (DPM) was determined. In these examples, too, the dwell time in the remover bath had been chosen such that measurable resist coatings remained on the substrate.
The results compiled in Table 4 show that an optimum effectiveness is achieved when the mixture is comprised of 22.5% by weight of isopropanolamine and 77.5~ by weight of dipropylene glycol methyl e.her.
Examples 22 and 23 In these examples, the behavior of the removers towards aluminum layers was tested by heating the com-positions corresponding to Examples 13 and 19 to a tem-perature of 80C and allowing them to act on aluminum-coated wafers for 30 minutes. No attack of the aluminum layer was observed.
. Table 1:
.
Example Composition* Thickness of : No. . resist coatinc l 64.4% Di-(n-propylene)-triamine 0.380 ~m 35.6% Tripropylene-glycol-methyl ether (TPM) .
2 50.7% Diethylene-triamine 0.249 ~m 49.3% TPM -3 71.8% Triethylene-tetraamine 0 ~m 28.2~ TPM
4 36.9% Isopropanolamine (IPA) 0 ~m 63.1% TPM
51.0% N-(2-aminoethyl)-ethanol amine (AEEA) 0 ~m 49.0% TPM
* Percentages expressed by weight . _g_ 1;~795~;1 Table 2:
Example Composition* jThickness of No. . resist coatinc 6 63.9~ Hydroxyethyl piperazine 1.517 ~m 36.1~ TPM
7 51.6~ Aminoethoxyethanol 0.396 ~m 48.4~ TPM
8 50.7% Diethylene triamine 0.369 ~m 49.3% TPM
9 36.9% IPA 0.293 ~m 63.1~ TPM
71.8% Triethylene tetramine O ~m 28.2% TPM
11 51.0~ AEEA O ~m 49.0% TPM
12 36.9% IPA
63.1% Dipropylene glycol methyl O ~m . ether (DPM) * Percentages expressed by weight . --10--~Z79S~l Table 3:
Example Composition* Thickness of No resist coatin _ 13 75~ N-~2-aminoethyl)-ethanol amine (AEEA) 0.652 ~m 25% Tripropylene-glycol-methyl ether (TPM) _ 14 51% AEEA 0.387 ~m 49% TPM
35~ AEEA 0.758 ~m 65~ TPM
16 25% AEEA 0.860 ~m 75% TPM
17 15% AEEA 0.896 ~m 85% TPM
18 10% AEEA 1.174 ~m 90~ TPM
* Percentages expressed by weight . . .
~;~79561 Table 4.
Example Composition Thickness of No resist coatinc _ 19 10.0% IPA 1.22 ~m 90.0% DPM
20. 22.5% IPA 0.S0 ~m 77.5% DPM _ 21 36.9% IPA 0.83 ~m 63.1% DPM _ * Percentages expressed by weight Examples 24 to 27 To test the effectiveness of removers of the present invention, photopolymerizable photoresists were used that are developable by means of aqueous-alkaline developers and are customarily employed in the production of circuit boards. A commercially available dry resist (Ozatec~ T 138, made by Hoechst AG) was bonded to a copper-clad laminate board at 115 C, exposed for 8 seconds to a 5 kw metal halide lamp arranged at a distance of 60 cm, and developed in a 1% strength aqueous Na2C3 solution having a temperature of 30C for 70 seconds.
The removal tests were performed in a movin~
bath having a temperature of 50 C. After 10 minutes, the results compiled in Table 5 were achieved. The re-sists were removed both by undiluted removal agents and by agents that had been diluted with water.
1~7956~
Table 5:
Example No. ComPOsition Resist removed 24 51% AEEA yes 49% TPM
12.75% AEEA yes 12.25% TPM
75~ water 26 22.5% IPA yes ; 77.5% DPM
27 5.63% IPA yes 19.37% DPM
: 7s% water
51.0% N-(2-aminoethyl)-ethanol amine (AEEA) 0 ~m 49.0% TPM
* Percentages expressed by weight . _g_ 1;~795~;1 Table 2:
Example Composition* jThickness of No. . resist coatinc 6 63.9~ Hydroxyethyl piperazine 1.517 ~m 36.1~ TPM
7 51.6~ Aminoethoxyethanol 0.396 ~m 48.4~ TPM
8 50.7% Diethylene triamine 0.369 ~m 49.3% TPM
9 36.9% IPA 0.293 ~m 63.1~ TPM
71.8% Triethylene tetramine O ~m 28.2% TPM
11 51.0~ AEEA O ~m 49.0% TPM
12 36.9% IPA
63.1% Dipropylene glycol methyl O ~m . ether (DPM) * Percentages expressed by weight . --10--~Z79S~l Table 3:
Example Composition* Thickness of No resist coatin _ 13 75~ N-~2-aminoethyl)-ethanol amine (AEEA) 0.652 ~m 25% Tripropylene-glycol-methyl ether (TPM) _ 14 51% AEEA 0.387 ~m 49% TPM
35~ AEEA 0.758 ~m 65~ TPM
16 25% AEEA 0.860 ~m 75% TPM
17 15% AEEA 0.896 ~m 85% TPM
18 10% AEEA 1.174 ~m 90~ TPM
* Percentages expressed by weight . . .
~;~79561 Table 4.
Example Composition Thickness of No resist coatinc _ 19 10.0% IPA 1.22 ~m 90.0% DPM
20. 22.5% IPA 0.S0 ~m 77.5% DPM _ 21 36.9% IPA 0.83 ~m 63.1% DPM _ * Percentages expressed by weight Examples 24 to 27 To test the effectiveness of removers of the present invention, photopolymerizable photoresists were used that are developable by means of aqueous-alkaline developers and are customarily employed in the production of circuit boards. A commercially available dry resist (Ozatec~ T 138, made by Hoechst AG) was bonded to a copper-clad laminate board at 115 C, exposed for 8 seconds to a 5 kw metal halide lamp arranged at a distance of 60 cm, and developed in a 1% strength aqueous Na2C3 solution having a temperature of 30C for 70 seconds.
The removal tests were performed in a movin~
bath having a temperature of 50 C. After 10 minutes, the results compiled in Table 5 were achieved. The re-sists were removed both by undiluted removal agents and by agents that had been diluted with water.
1~7956~
Table 5:
Example No. ComPOsition Resist removed 24 51% AEEA yes 49% TPM
12.75% AEEA yes 12.25% TPM
75~ water 26 22.5% IPA yes ; 77.5% DPM
27 5.63% IPA yes 19.37% DPM
: 7s% water
Claims (7)
1. An agent for the removal of photoresists which is comprised of (a) from about 10 to 100% by weight of at least one water-soluble amine represented by the formula in which R1, R2, R3, R4 denote H or alkyl groups n,m denote 0 to 2, and o denotes 1 to 3;
and (b) from about 0 to 90% by weight of at least one water-soluble propylene glycol derivative represented by the formula in which R3, R4 denote H, alkyl or C-alkyl groups, and P denotes 1 to 3.
and (b) from about 0 to 90% by weight of at least one water-soluble propylene glycol derivative represented by the formula in which R3, R4 denote H, alkyl or C-alkyl groups, and P denotes 1 to 3.
2. An agent as claimed in Claim 1, wherein said water-soluble amine is selected from a group comprising isopropanolamine or N-(2-aminoethyl)-ethanol-amine.
3. An agent as claimed in Claim 1, wherein said water-soluble propylene glycol derivative is selected from a group comprising dipropylene glycol methyl ether or tripropylene glycol methyl ether.
4. An agent as claimed in Claim 1, wherein said agent is comprised of a water-soluble amine in an amount from about 10-90% by weight, and a water-soluble propylene glycol derivative in an amount from about 10 to 90% by weight.
5. An agent as claimed in Claim 1, wherein said agent is comprised of a water-soluble amine in an amount from about 20-70% by weight, and a water-soluble propylene glycol derivative in an amount from about 30 to 80% by weight.
6. An agent as claimed in Claim 1, wherein the boiling points of said water-soluble amine and said water-soluble propylene glycol derivative are at least 160°C
7. An agent as claimed in Claim 1, wherein the boiling points of said water-soluble amine and said water-soluble propylene glycol derivative are at least 180°C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000520952A CA1279561C (en) | 1985-10-22 | 1986-10-21 | Solvents for photoresist removal |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3537441.1 | 1985-10-22 | ||
| CA000520952A CA1279561C (en) | 1985-10-22 | 1986-10-21 | Solvents for photoresist removal |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1279561C true CA1279561C (en) | 1991-01-29 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000520952A Expired - Fee Related CA1279561C (en) | 1985-10-22 | 1986-10-21 | Solvents for photoresist removal |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA1279561C (en) |
-
1986
- 1986-10-21 CA CA000520952A patent/CA1279561C/en not_active Expired - Fee Related
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| Date | Code | Title | Description |
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| MKLA | Lapsed |