CN108535971B - Stripping liquid composition for removing photoresist - Google Patents
Stripping liquid composition for removing photoresist Download PDFInfo
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- CN108535971B CN108535971B CN201810178861.7A CN201810178861A CN108535971B CN 108535971 B CN108535971 B CN 108535971B CN 201810178861 A CN201810178861 A CN 201810178861A CN 108535971 B CN108535971 B CN 108535971B
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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
Abstract
The present invention relates to a resist remover composition, and more particularly, to a resist remover composition which does not contain toxic substances harmful to the human body, has excellent dissolution of a removed resist, minimizes problems in processes such as filter clogging, and minimizes corrosion of metal wiring.
Description
Technical Field
The present invention relates to a resist remover composition, and more particularly, to a resist remover composition which does not contain toxic substances harmful to the human body, has excellent dissolution of a removed resist, minimizes problems in processes such as filter clogging, and minimizes corrosion of metal wiring.
Background
The photolithography process is a series of photo processes for transferring a pattern designed on a mask (mask) onto a substrate on which a thin film to be processed is formed.
More specifically, a thin film is formed on a substrate, a photoresist as a photosensitive material is uniformly coated on the thin film, a mask is disposed on the substrate coated with the photoresist and exposure is performed, and then the photoresist is developed (development) to form a photoresist pattern. The thin film may be also referred to as a lower film, and may be, for example, a conductive metal film such as aluminum, aluminum alloy, copper alloy, molybdenum alloy, or the like, an insulating film such as a silicon oxide film or a silicon nitride film, or the like.
The photoresist pattern may be etched by wet or dry etching using a mask, and the fine circuit pattern may be transferred and etched. After such patterning, a photoresist remaining on the thin film is removed, and a photoresist removing stripper (stripper) composition is used for this purpose.
The photoresist removing stripping liquid used in the process of forming the electrode circuit for the display and the semiconductor should be capable of stripping the photoresist at a low temperature in a short time, and should not leave a photoresist residue on the substrate after washing (ring), and should have an ability to strip the organic insulating film and the metal wiring without damaging them.
In korean laid-open patent No. 10-2011-0129555, korean laid-open patent No. 10-2014-0028962, korean laid-open patent No. 10-2015-0102354, and the like, as a stripping liquid for photoresist removal, an organic compound such as an amine compound, an alkylene glycol alkyl ether compound, an aprotic polar solvent, and an anticorrosive agent is used, and among them, an aprotic solvent such as N-methylformamide (NMF) or N-methylpyrrolidone (NMP) excellent in stripping property and anticorrosive property has been used as a main solvent. Although such solvents have the advantage of excellent peeling force, they are substances exhibiting reproductive toxicity, and have the disadvantage of being harmful to the environment and human body, so that their use is gradually restricted. Therefore, in practice, there is a demand for development of a stripping liquid composition having an excellent stripping force even without using NMF or NMP, but a stripping liquid composition exhibiting a sufficient stripping force and washing force has not been developed until now.
Further, the stripping liquid composition containing the NMF and NMP has the following problems: over time, the decomposition of the amine compound is promoted, and the peeling force, the washing force, and the like decrease over time. Such problems may be further exacerbated as a portion of the residual photoresist dissolves in the stripper composition as the stripper composition is used a number of times.
In view of such problems, a stripping solution composition containing other polar aprotic solvents such as N, N' -Dimethylformamide (DMF) in place of the NMF has been studied, but it is known that the DMF also exhibits biotoxicity, and thus, there is a need for restrictions in use.
In view of the above, there has been no real development of a stripping liquid composition which does not contain a solvent exhibiting biotoxicity and which maintains excellent stripping force and detergency over time.
In view of such a practical situation, a method of including an excessive amount of an amine compound in a stripping liquid composition has been conventionally used in order to maintain excellent stripping force and washing force over time, but in this case, the economical efficiency and efficiency of the process may be greatly reduced, and environmental and process problems may occur due to the excessive amount of the amine compound.
Prior art literature
Patent literature
Korean laid-open patent No. 10-2011-0129955
Korean laid-open patent No. 10-2014-0028962
Korean laid-open patent No. 10-2015-0102354
Disclosure of Invention
The present invention has been made to solve the above problems, and an object of the present invention is to provide a stripping liquid composition for removing a photoresist, which can strip a photoresist at a low temperature in a short time even when such a solvent is used, can further improve the stripping speed, can remove an organic insulating film and a metal wiring without leaving a photoresist residue on a substrate after washing (ring), and can remove the organic insulating film and the metal wiring without damaging the substrate.
Further, it is an object to provide a stripping liquid composition for removing a photoresist, which is excellent in stability with time.
More specifically, the present invention aims to provide a stripping liquid composition for removing photoresist, which is harmless to the environment and the human body and can maximize the stripping force and the dissolution force of the stripped resist by using N-ethylformamide (NEF) and a polar solvent containing a hydrophobic group.
Further, it is an object of the present invention to provide a stripping liquid composition for removing a photoresist, which is more excellent in water-exchange property and also excellent in stability with time.
Further, it is an object to provide a method for stripping a photoresist using the stripping liquid composition for removing a photoresist.
The present invention for achieving the above object relates to a stripping liquid composition for removing photoresist, which comprises N-ethylformamide, a first amine compound represented by the following chemical formula 1, and a first polar solvent represented by the following chemical formula 2.
[ chemical formula 1]
In the chemical formula 1, R is 1 Selected from hydrogen, straight-chain or branched C 1 ～C 5 Alkylamine and straight-chain or branched C 1 ～C 5 A hydroxyalkyl group.
[ chemical formula 2]
In the chemical formula 2, R is 2 Selected from hydrogen, straight-chain or branched C 1 ～C 5 Alkyl, wherein n is a natural number selected from 1 to 3.
In one embodiment of the present invention, the first amine compound represented by chemical formula 1 may be any one or a mixture of two or more selected from the group consisting of 1-amino-2-propanol, 1- [ (2-aminoethyl) amino ] -2-propanol, and 1, 1-iminodi-2-propanol.
In one embodiment of the present invention, the first polar solvent represented by chemical formula 2 may be any one or a mixture of two or more selected from dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monopropyl ether and dipropylene glycol monobutyl ether.
In one embodiment of the present invention, the stripping liquid composition may further include a second amine compound satisfying the following relation 1, a second polar solvent satisfying the following relation 2, and a mixture thereof.
[ relation 1]
A1 bp <A2 bp
In the above relation 1, the above A1 bp The boiling point temperature of the first amine compound, A2 bp Is the boiling temperature of the second amine compound.
[ relation 2]
S1 bp <S2 bp
In the above relation 2, the above S1 bp The boiling point temperature of the first polar solvent is S2 bp Is the boiling temperature of the second polar solvent.
In one embodiment of the present invention, the first amine compound may be 1-amino-2-propanol or 1- [ (2-aminoethyl) amino ] -2-propanol, and the second amine compound may be any one or a mixture of two or more selected from monoethanolamine, 2- (2-aminoethoxy) ethanol, diethanolamine, 3-amino-1-propanol and N- (2-aminoethyl) ethanolamine.
In one embodiment of the present invention, the first polar solvent may be dipropylene glycol monomethyl ether, and the second polar solvent may be any one or a mixture of two or more selected from diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol t-butyl ether, triethylene glycol t-butyl ether, diethylene glycol monohexyl ether, triethylene glycol monoethyl ether, triethylene glycol monomethyl ether, and polyethylene glycol.
In one embodiment of the present invention, the stripping liquid composition may further include any one selected from the group consisting of an anticorrosive agent and deionized water, or a mixture thereof.
In one embodiment of the present invention, the anticorrosive agent may be any one or a mixture of two or more selected from the group consisting of triazole-based compounds and gallate-based compounds.
In one embodiment of the present invention, the total weight of the stripping liquid composition may include 10 to 90 wt%, more specifically 20 to 85 wt%, of the N-ethylformamide, 1 to 50 wt%, more specifically 3 to 30 wt%, of the first amine compound represented by chemical formula 1, and 1 to 50 wt%, more specifically 5 to 40 wt%, of the first polar solvent represented by chemical formula 2.
In one embodiment of the present invention, the total weight of the stripping liquid composition may further include 1 to 20 wt% of a second polar solvent satisfying the following relation 1,1 to 30 wt% of a second polar solvent satisfying the following relation 2, and a mixture thereof.
[ relation 1]
A1 bp <A2 bp
In the above relation 1, the above A1 bp The boiling point temperature of the first amine compound, A2 bp Is the boiling temperature of the second amine compound.
[ relation 2]
S1 bp <S2 bp
In the above relation 2, the above S1 bp The boiling point temperature of the first polar solvent is S2 bp Is the boiling temperature of the second polar solvent.
In one embodiment of the present invention, the total weight of the stripping liquid composition may further include any one or a mixture of 0.01 to 5 wt% of an anticorrosive agent and 1 to 40 wt% of deionized water.
Furthermore, the present invention relates to a photoresist stripping method, comprising:
a step of forming a photoresist pattern on the substrate on which the lower film is formed;
patterning the lower film using the photoresist pattern; and
and stripping the photoresist by using the stripping liquid composition.
The stripping liquid composition for removing photoresist of the present invention can rapidly strip photoresist even without using N-methylformamide (NMF) and N-methylpyrrolidone (NMP) as main solvents, which are harmful to the environment and human body. The stripping liquid composition for removing photoresist of the present invention can rapidly strip the modified photoresist even after dry or wet etching.
Further, it is possible to provide a stripping liquid composition for removing a photoresist, which can strip a photoresist in a short time at a low temperature, can further improve the stripping speed, can leave no photoresist residue on a substrate after washing (ring), and can strip an organic insulating film and a metal wiring without damaging the same.
In addition, the following advantages are present: the stripped photoresist has excellent dissolving power, and filter clogging is minimized in the process, so that the process efficiency can be significantly increased.
Further, a stripping liquid composition for removing photoresist having excellent stability with time can be provided.
Detailed Description
Hereinafter, the photoresist remover composition will be described in detail. The present invention relates to a stripper composition for photoresist removal used in display, OLED fabrication and semiconductor fabrication, which can be better understood by the following examples, which are given to illustrate the present invention and not to limit the scope of protection defined by the appended claims.
The inventors of the present invention have studied to develop a stripping liquid composition that can improve the removal rate of a photoresist without using N-methylformamide (NMF) and N-methylpyrrolidone (NMP) as main solvents, and as a result, have found that when N-ethylformamide, a first amine compound represented by the following chemical formula 1, and a first polar solvent represented by the following chemical formula 2 are used together, the time consumed for removing the photoresist can be shortened, the dissolution force of the stripped photoresist is excellent, the problems in the process of filter clogging can be minimized, and the stability over time is excellent, and thus have completed the present invention.
[ chemical formula 1]
In the chemical formula 1, R is 1 Selected from hydrogen, straight-chain or branched C 1 ～C 5 Alkylamine and straight-chain or branched C 1 ～C 5 A hydroxyalkyl group.
[ chemical formula 2]
In the chemical formula 2, R is 2 Selected from hydrogen, straight-chain or branched C 1 ～C 5 Alkyl, wherein n is a natural number selected from 1 to 3.
Specifically, it was found that the use of N-ethylformamide solves the environmental problems caused by the use of N-methylformamide (NMF) and N-methylpyrrolidone (NMP), and that the use of a compound containing a hydrophobic isopropylidene (isopropylene) structure as shown in chemical formula 1 and chemical formula 2 together with N-ethylformamide allows an amine compound to exert an effect of more easily cleaving the crosslinking bond of a photoresist according to the synergistic effect of these compounds, and can further shorten the peeling time, and achieve a peeling rate equivalent to or superior to that of a conventional NMF or NMP composition, thereby completing the present invention. Further, it has been found that the resist to be stripped is excellent in not only stripping force but also dissolution force and stability with time, and the present invention has been completed.
Further, it has been found that the composition further contains a second amine compound having a higher boiling point than the first amine compound in addition to the first amine compound represented by the chemical formula 1, and thus the stability with time can be further improved.
It was found that the water-exchange property can be further improved by further including a second polar solvent having a higher boiling point and hydrophilicity than those of the first polar solvent in the composition, in addition to the first polar solvent represented by the chemical formula 2.
An embodiment of the present invention will be described in more detail below.
The first embodiment of the present invention includes N-ethylformamide, a first amine compound represented by chemical formula 1, and a first polar solvent represented by chemical formula 2.
The second embodiment of the present invention comprises N-ethylformamide, a first amine compound represented by chemical formula 1, a first polar solvent represented by chemical formula 2, and an anticorrosive agent.
A third embodiment of the present invention includes N-ethylformamide, a first amine compound represented by chemical formula 1. A first polar solvent represented by chemical formula 2, and ultrapure water or deionized water.
The fourth aspect of the present invention comprises N-ethylformamide, the first amine compound represented by chemical formula 1, the first polar solvent represented by chemical formula 2, an anticorrosive agent, and ultrapure water or deionized water.
A fifth aspect of the present invention includes N-ethylformamide, a first amine compound represented by chemical formula 1, a first polar solvent represented by chemical formula 2, and a second amine compound satisfying the following relationship 1.
[ relation 1]
A1 bp <A2 bp
In the above relation 1, the above A1 bp The boiling point temperature of the first amine compound, A2 bp Is the boiling temperature of the second amine compound.
A sixth aspect of the present invention includes N-ethylformamide, a first amine compound represented by chemical formula 1, a first polar solvent represented by chemical formula 2, and a second polar solvent satisfying the following relationship 2.
[ relation 2]
S1 bp <S2 bp
In the above relation 2, the above S1 bp The boiling point temperature of the first polar solvent is S2 bp Is the boiling temperature of the second polar solvent.
A seventh aspect of the present invention includes N-ethylformamide, a first amine compound represented by chemical formula 1, a first polar solvent represented by chemical formula 2, a second amine compound satisfying the above-mentioned relation 1, and a second polar solvent satisfying the above-mentioned relation 2.
An eighth aspect of the present invention includes N-ethylformamide, a first amine compound represented by chemical formula 1, a first polar solvent represented by chemical formula 2, a second amine compound satisfying the above-described relationship 1, and an anticorrosive agent.
The ninth aspect of the present invention comprises N-ethylformamide, a first amine compound represented by chemical formula 1, a first polar solvent represented by chemical formula 2, a second polar solvent satisfying the above-mentioned relationship 2, and an anticorrosive agent.
A tenth aspect of the present invention includes N-ethylformamide, a first amine compound represented by chemical formula 1, a first polar solvent represented by chemical formula 2, a second amine compound satisfying the above-mentioned relation 1, a second polar solvent satisfying the above-mentioned relation 2, and an anticorrosive agent.
The first to tenth embodiments described above are only one embodiment for specifically illustrating the present invention, and are not limited thereto. In addition, additives commonly used in the art may be further contained as needed.
In one embodiment of the present invention, the content of the N-ethylcarboxamide is not limited, but may be contained in an amount of 10 to 90% by weight in the total composition. It may more preferably comprise 20 to 85% by weight, more preferably 40 to 85% by weight. In the above range, the stripping force can be improved to significantly shorten the photoresist removal time, and the lower film corrosion can be minimized.
In one embodiment of the present invention, the first amine compound represented by chemical formula 1 acts on a relatively weak portion of the surface of the modified photoresist, thereby allowing the solvent component to easily permeate. Further, by using the N-ethylformamide and the first polar solvent represented by chemical formula 2, the composition is harmless to the human body and exerts a protruding effect of maximizing the stripping force and the dissolution force of the stripped photoresist. In addition, the effect of improving the stability with time is obtained.
The first amine compound represented by the above chemical formula 1 may be specifically any one or a mixture of two or more selected from, for example, 1-amino-2-propanol, 1- [ (2-aminoethyl) amino ] -2-propanol, 1-iminodi-2-propanol, and the like, but is not limited thereto.
The content of the first amine compound represented by the above chemical formula 1 may be 1 to 50% by weight based on the total weight of the stripping liquid composition for photoresist removal. More preferably from 3 to 30% by weight, even more preferably from 5 to 15% by weight. When the content is within the above range, the stripping force for the modified photoresist can be significantly improved.
In one embodiment of the present invention, the first polar solvent represented by chemical formula 2 is a glycol compound containing an isopropylidene group as a hydrophobic group, and is excellent in wettability to a photoresist, and therefore, not only the stripping force but also the dissolution force of the stripped photoresist can be significantly improved.
The first polar solvent represented by chemical formula 2 is used together with the N-ethylformamide and the first amine compound represented by chemical formula 1, thereby being harmless to the human body and exerting a protruding effect of maximizing the stripping force and the dissolution force of the stripped photoresist. In addition, the effect of improving the stability with time is obtained.
The first polar solvent represented by the above chemical formula 2 may be specifically any one or a mixture of two or more selected from propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monopropyl ether, dipropylene glycol monobutyl ether, tripropylene glycol monomethyl ether, tripropylene glycol monoethyl ether, tripropylene glycol monopropyl ether, tripropylene glycol monobutyl ether, and the like.
More preferably, it is one or a mixture of two or more selected from dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monopropyl ether and dipropylene glycol monobutyl ether.
The content of the first polar solvent represented by the above chemical formula 2 may be 1 to 50 wt% based on the total weight of the stripping liquid composition for photoresist removal. More preferably from 5 to 40 wt%, more preferably from 15 to 30 wt%. By including the above-mentioned range, even if an aprotic polar solvent harmless to the human body is used, the stripping force of the photoresist and the dissolution force of the stripped photoresist can be significantly improved, and the process efficiency can be improved.
In one embodiment of the present invention, the stripping liquid composition for removing photoresist may further include an amine compound commonly used in the art, in addition to the first amine compound represented by chemical formula 1.
More preferably, the second amine compound having a higher boiling point than the first amine compound as shown in the following formula 1 is further contained, whereby the volatility can be further reduced and the stability with time can be further improved.
[ relation 1]
A1 bp <A2 bp
In the above relation 1, the above A1 bp The boiling point temperature of the first amine compound, A2 bp Is the boiling temperature of the second amine compound.
More specifically, for example, by including an amine compound having a boiling point higher than the first amine compound by 1 ℃ or more, more preferably 10 ℃ or more, as the second amine compound, the stability with time can be further improved.
Specific examples of the second amine compound may be any one or a mixture of two or more selected from monoethanolamine, 2- (2-aminoethoxy) ethanol, diethanolamine, 3-amino-1-propanol, N- (2-aminoethyl) ethanolamine, and the like, but are not limited thereto. More suitably 2- (2-aminoethoxy) ethanol and diethanolamine.
More specifically, for example, the first amine compound may be 1-amino-2-propanol or 1- [ (2-aminoethyl) amino ] -2-propanol, and the second amine compound may be any one or a mixture of two or more selected from monoethanolamine, 2- (2-aminoethoxy) ethanol, diethanolamine, 3-amino-1-propanol and N- (2-aminoethyl) ethanolamine.
The content of the second amine compound may be 1 to 50% by weight based on the total weight of the stripping liquid composition for photoresist removal. More preferably from 1 to 20% by weight, even more preferably from 3 to 10% by weight. By including the above range, the stability with time can be further improved without inhibiting the peeling force and the dissolution force.
In one embodiment of the present invention, the stripping liquid composition for removing photoresist may further include a polar solvent commonly used in the art, in addition to the first polar solvent represented by chemical formula 2.
More preferably, the water-exchange property can be further improved by further containing a second polar solvent having a higher boiling point than the first polar solvent as shown in the following formula 2.
[ relation 2]
S1 bp <S2 bp
In the above relation 2, the above S1 bp The boiling point temperature of the first polar solvent is S2 bp Is the boiling temperature of the second polar solvent.
More specifically, for example, the water-exchange property can be further improved by including a polar solvent having a boiling point higher than the first polar solvent by 1 ℃ or more, more preferably 10 ℃ or more, as the second polar solvent. More preferably, a polar solvent having a high boiling point and a higher polarity because it does not contain an isopropylidene structure as shown in the above-mentioned relational expression 2 can be used.
Specific examples of the second polar solvent may be any one or a mixture of two or more selected from diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol t-butyl ether, triethylene glycol t-butyl ether, diethylene glycol monohexyl ether, triethylene glycol monoethyl ether, triethylene glycol monomethyl ether, polyethylene glycol, and the like, but are not limited thereto. More suitably diethylene glycol monobutyl ether, diethylene glycol monoethyl ether, diethylene glycol monohexyl ether, triethylene glycol monoethyl ether, triethylene glycol monomethyl ether and polyethylene glycol.
More specifically, for example, the first polar solvent may be dipropylene glycol monomethyl ether, and the second polar solvent may be any one or a mixture of two or more selected from diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol t-butyl ether, triethylene glycol t-butyl ether, diethylene glycol monohexyl ether, triethylene glycol monoethyl ether, triethylene glycol monomethyl ether, and polyethylene glycol.
The content of the second polar solvent may be 1 to 50 wt% based on the total weight of the stripping liquid composition for photoresist removal. More preferably from 1 to 30% by weight, even more preferably from 10 to 20% by weight. When the content is within the above range, the water-exchange property can be further improved without inhibiting the peeling force and the dissolving force.
In one embodiment of the present invention, the stripping liquid composition for removing photoresist may contain an anticorrosive agent, and the anticorrosive agent is not limited as long as it is an anticorrosive agent commonly used in the art, and specifically, for example, a triazole compound, a gallate compound, and the like may be used. The anticorrosive agent is easily dissolved in the stripping liquid, and functions as an oxidizing agent and a complex in the DI washing step, and is characterized by suppressing an electrochemical effect (Galvanic effect) caused by an organic amine and eliminating the corrosive effect on the metal wiring.
The triazole compound is not limited as long as it is a compound which is obviously known in the art, and specifically, any one or a mixture of two or more selected from benzotriazole, o-tolyltriazole, m-tolyltriazole, p-tolyltriazole, carboxybenzotriazole, 1-hydroxybenzotriazole, nitrobenzotriazole, dihydroxypropylbenzotriazole, tetrahydrotolyltriazole and the like can be used, but is not limited thereto.
The gallate compound is not limited as long as it is a compound which is obviously known in the art, and specifically, any one or a mixture of two or more selected from the group consisting of methyl gallate, ethyl gallate, propyl gallate, isopropyl gallate, butyl gallate, t-butyl gallate and octyl gallate can be used, but the present invention is not limited thereto.
The content of the anticorrosive agent in the stripping liquid composition for photoresist removal may be used within a range that does not inhibit the physical properties of the stripping liquid composition for photoresist removal, and may be 0.01 to 5 wt%, more preferably 0.05 to 2 wt%, still more preferably 0.1 to 0.5 wt%, but is not limited thereto.
The stripping liquid composition for removing photoresist of the present invention may further contain, in addition to the above components, additives which are usually added, if necessary, without limitation, and specifically, may further contain one or more additives selected from, for example, water-exchange improving agents, surfactants, antifoaming agents, and mixtures thereof.
That is, a surfactant may be further added to the composition of the present invention in order to improve the uniformity of cleaning, and an antifoaming agent may be used as an additive in order to suppress the occurrence of bubbles that interfere with cleaning. The amount of the additive is not limited, but may be 20 parts by weight or less, preferably 5 parts by weight or less, based on 100 parts by weight of the total weight of the stripping liquid composition for removing a photoresist, but is not limited thereto. On the other hand, examples of usable surfactants and antifoaming agents are generally known in the art, and for example, as the surfactant, amphoteric, cationic, anionic, nonionic or fluorine-based surfactants may be used, and as the antifoaming agent, a silicon-based or non-silicon-based antifoaming agent may be used.
In one embodiment of the present invention, the photoresist stripping liquid composition may be an aqueous or non-aqueous composition.
To make the aqueous composition, deionized water may be further included. The deionized water may be used in the same manner as ultrapure water, purified water, or the like, and may be used in a range that does not inhibit the physical properties of the stripping liquid composition for photoresist removal, but is not limited thereto, but may be more specifically contained in an amount of 1 to 40% by weight, and may be further specifically contained in an amount of 2 to 15% by weight.
Further, according to still another embodiment of the present invention, there may be provided a method of stripping a photoresist which is treated with the stripping liquid composition for photoresist removal described above.
The photoresist stripping method may include: and a stripping (stripping) step of etching the substrate with the photoresist pattern formed on the substrate including the organic insulating film, the metal wiring, or the lower film such as the metal wiring and the inorganic material layer as a mask, and stripping the photoresist with the stripping liquid composition for photoresist removal.
More specifically, it may include: a step of forming a photoresist pattern on the substrate on which the lower film is formed; patterning the lower film using the photoresist pattern; and a step of stripping the photoresist using the stripping liquid composition.
In such a lift-off method, first, a photoresist pattern may be formed on a substrate on which a lower film to be patterned is formed, through a photolithography process. After that, the photoresist pattern may be used as a mask, and the lower film may be patterned, and then the photoresist may be stripped by using the stripping liquid composition or the like. In the above steps, the formation of the photoresist pattern and the patterning of the lower film may be performed in accordance with a normal device manufacturing process, and thus additional description thereof will be omitted.
On the other hand, when the photoresist is stripped by the stripping liquid composition, the photoresist pattern may be first processed on the substrate with the stripping liquid composition, washed with an alkaline buffer solution, washed with ultrapure water, and dried.
The method of stripping a photoresist from a substrate etched with a fine circuit pattern using the stripping liquid composition for a photoresist according to an embodiment of the present invention may use the following manner: a dipping method of dipping (dipping) a plurality of substrates to be peeled in a large amount of peeling liquid at the same time; and a single-wafer method of removing the photoresist by spraying a stripping liquid onto a single substrate, but the method is not limited thereto.
Examples of the type of photoresist that can be stripped using the stripping liquid composition for photoresist of the present invention include positive photoresist, negative photoresist, and positive/negative photoresist (dual tone photoresist). The photoresist that can be applied particularly effectively may be a photoresist composed of a photoactive compound containing a novolak-type phenol resin and diazonaphthoquinone, although the constituent components are not limited.
The metal wiring to which the photoresist removing stripping liquid composition can be applied may include Al, cu, ag, ti, mo, and the like as a lower film, and may be used as a p-electrode and an n-electrode, but is not limited thereto.
Hereinafter, preferred embodiments of the stripping liquid composition for removing photoresist and the performance measurement method of the present invention will be described in detail.
1) Photoresist stripping force evaluation
For the stripping liquid composition for removing photoresist, which was prepared as shown in Table 1 below, in order to evaluate the stripping performance of the photoresist, a glass substrate was coated with a photoresist (AZEM, DTR-300) at a thickness of 1.5 μm, and then hard baked (hard cake; H/B) at 160℃and 170℃for 10 minutes, respectively, to prepare test pieces. The time required for the photoresist to be completely peeled off by the peeling liquid was measured under a spray pressure of 0.4kgf using a peeling apparatus in a form of a single spray maintained at a temperature of 60 c, and the evaluation results are shown in table 2 below.
At this time, after ultraviolet rays were irradiated on the glass substrate, whether or not the photoresist remained was observed, and whether or not the photoresist was peeled was confirmed.
2) Evaluation of solvency
For the stripping liquid composition for removing photoresist, which was prepared as shown in table 1 below, in order to evaluate the dissolution force of photoresist, the photoresist (AZEM, DTR-300) was dried for 4 hours at 150 ℃ in a hot plate, thereby preparing photoresist powder. The dissolution force was evaluated by charging 2 wt% of the dry photoresist powder into the stripping liquid composition in a constant temperature state at 60℃under stirring at 300rpm and stirring for 20 minutes to dissolve it, and then passing it through a 10 μm filter (PTFE having pores of 10 μm). The case where 2% by weight of the photoresist was completely dissolved within 20 minutes and the remaining amount was not measured after filtration was taken as 100%, and it is considered that the higher the value, the more the photoresist was dissolved, and therefore the more the number of processed sheets was. The dissolution force can be calculated according to the following formula.
Dissolution force (%) = [ (content of photoresist used for 2 wt% of solid content-content of photoresist remaining in filter)/content of photoresist used for 2 wt% of solid content ] ×100
3) Lower film corrosion evaluation
The lower film damage degree was confirmed by a 200-magnification optical microscope and a 10K to 50K magnification FE-SEM for a dried test piece after complete peeling with the peeling liquid of examples and comparative examples under a spray pressure of 0.4kgf using a peeling apparatus maintaining a single spray form at a temperature of 60 ℃. The results are shown in table 2 below.
And (3) the following materials: no corrosion occurs
O: mild corrosion occurs
Delta: corrosion occurs
X: severe corrosion occurs
4) Evaluation of stability with time
(1) Evaluation of Peel force after time-lapse change
In order to evaluate the stability of the composition over time, the peeling force of the composition after the composition was evaluated over time by the same method as in 1) above. The results are shown in table 2 below.
500g of the stripping liquid compositions produced in examples and comparative examples were prepared, and 2 wt% of a photoresist (AZEM, DTR-300) was charged and dissolved in the state of being heated to 60 ℃. The above stripping solution was heated at 60 ℃ for 12 to 48 hours to cause a change over time under severe conditions.
The peeling force was measured in the same manner as in 1) above for the peeling liquid composition that had undergone such a change over time, and the stability over time was evaluated.
(2) Evaluation of dissolution force after time-lapse
The photoresist (AZEM, DTR-300) was dried for 4 hours at 150 ℃ with a heating plate to manufacture photoresist powder. The dry photoresist powder was poured into the stripping liquid composition in a constant temperature state of 60 c under stirring at 300rpm for 2 wt% and stirred for 20 minutes to be dissolved. The above stripping solution was heated at 60 ℃ for 12 to 48 hours to cause a change over time under severe conditions.
As in 2) above, the dissolution force was evaluated by passing the stripping liquid composition which had been changed with time through a1 μm filter (PTFE having pores of 1 μm).
Dissolution force (%) = [ (content of photoresist used for 2 wt% of solid content-content of photoresist remaining in filter)/content of photoresist used for 2 wt% of solid content ] ×100
5) Evaluation of Water substitution degree
The final step in the photoresist stripping process includes a step of washing with water. Therefore, the stripping liquid containing the photoresist remaining on the substrate should have good water-exchange properties with respect to water, and an evaluation was made to confirm the water-exchange properties.
The substrate immersed in the stripping liquid for 1 minute was taken out, and the stripping liquid was excessively dried for 1 minute by an air knife. After rinsing the substrate subjected to the drying in water, the speckle property of the substrate was visually confirmed. The composition having good water-exchange properties showed a weaker patch strength, and the results are shown in table 2 below.
And (3) the following materials: very good
O: good quality
Delta: occurrence of speckle
X: severe streaking occurs
6) Volatility degree
To confirm the volatility, 500g of the composition was put into a 1L beaker, and then placed in a 60℃incubator. After that, the weight after 24 hours was measured, and the volatility was calculated according to the following formula.
Volatility = [ (weight (g) of existing composition)) - (weight (g) of existing composition after 24 hours)) ]/weight (g) of existing composition x 100
Examples and comparative examples
The components and compositions described in table 1 below were mixed to prepare a stripping liquid composition for removing photoresist. At this time, the mixture was carried out at room temperature, and the mixture was mixed so as to be sufficiently dissolved for 1 hour or more, and then filtered by a Teflon filter (PTFE having pores of 1 μm) and used.
TABLE 1
< solvent >
NEF: n-ethyl formamide
NMF: n-methyl formamide
< first amine Compound >
MIPA: 1-amino-2-propanol
HEA:1- [ (2-aminoethyl) amino ] -2-propanol
IDP:1, 1-iminodi-2-propanol
< second amine Compound >
MEA: monoethanolamine
AEE:2- (2-Aminoethoxy) ethanol
DEA: diethanolamine (DEA)
3-AP: 3-amino-1-propanol
AEEA: n- (2-aminoethyl) ethanolamine
< first polar solvent >
DPGME: dipropylene glycol monomethyl ether
DPGEE: dipropylene glycol monoethyl ether
DPEPE: dipropylene glycol monopropyl ether
DPEBE: dipropylene glycol monobutyl ether
< second polar solvent >
MDG: diethylene glycol monomethyl ether
BDG: diethylene glycol monobutyl ether
EDG diethylene glycol monoethyl ether
TGTB: triethylene glycol tert-butyl ether
DGTB: diethylene glycol tertiary butyl ether
HDG: diethylene glycol monohexyl ether
TEG: triethylene glycol monoethyl ether
TMG: triethylene glycol monomethyl ether
< anticorrosive agent >
H4TT: tetrahydrotolyltriazole
TT: tolyltriazole
MG: methyl gallate
EG: gallic acid ethyl ester
PG: propyl gallate
BG: butyl gallate
OG: octyl gallate
In table 2 below, Δ12 refers to the physical properties measured after a change over time of 12 hours, and Δ48 refers to the physical properties measured after a change over time of 48 hours.
TABLE 2
As shown in table 2, it was confirmed that the stripping liquid composition for removing photoresist of the present invention was excellent in not only the removal rate and the dissolution force but also the lower film corrosion. Further, it was found that the stability with time was excellent.
As shown in examples 1 to 11, it was confirmed that the stripping force and the dissolution force were most excellent when the NEF, the first amine compound represented by chemical formula 1, and the first polar solvent represented by chemical formula 2 were used in combination.
Further, as shown in examples 12 to 16, even when the second polar solvent was further contained, the peeling force and the dissolution force were not changed, and it was confirmed that the water-exchange property was further improved.
Further, as shown in example 17, it was found that the peeling force and the dissolution force were reduced in the case of adding deionized water, but were more excellent than those of the comparative examples.
Further, as shown in examples 18 to 20, it was confirmed that the occurrence of corrosion of the lower film was further reduced by containing the corrosion inhibitor.
Further, as shown in examples 21 to 23, even when the second amine compound was further contained, the peeling force and the dissolution force were not changed, and it was confirmed that the stability with time was further improved because the volatility was lower than that in example 1.
Further, as shown in examples 24 to 31, even when the second polar solvent and the second amine compound were further contained, the peeling force and the dissolution force were not changed, the stability with time was further improved due to the low volatility, and the degree of water substitution was further improved.
As shown in comparative examples 1 to 7, it was confirmed that physical properties were lowered when any of the components was excluded from the composition of the present invention. The reason for this is that the first polar solvent represented by chemical formula 2 has a strong affinity to the photoresist that is the target to be removed and is rapidly wetted (wet), and at this time the first polar solvent represented by chemical formula 2 brings the first amine compound represented by chemical formula 1 of a similar structure to the photoresist surface at the same time to peel off and dissolve the photoresist more rapidly.
Further, as shown in comparative examples 8 to 10, it was confirmed that the dissolution force was lowered when other amide solvents such as NMP were used instead of NEF.
From this, it was confirmed that the stripping liquid composition for removing photoresist according to the present invention can provide a stripping liquid composition which is excellent in stripping force, dissolution force and stability with time, and can improve process efficiency even if it contains a solvent harmless to the human body, an amine compound, and a polar solvent containing a hydrophobic group.
While the preferred embodiments of the present invention have been described above, the present invention is susceptible to various modifications and alternative forms, and it is apparent that the above embodiments can be applied equally with appropriate modifications. Accordingly, the above description does not limit the scope of the invention, which is defined by the following claims.
Claims (11)
1. A stripping liquid composition for removing photoresist, which comprises N-ethylformamide, a first amine compound represented by the following chemical formula 1 and a first polar solvent comprising any one or more than two selected from dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monopropyl ether and dipropylene glycol monobutyl ether,
comprising 59.5 to 85% by weight of the N-ethylformamide, 5 to 15% by weight of the first amine compound represented by chemical formula 1, 5 to 30% by weight of the first polar solvent,
chemical formula 1
In the chemical formula 1, R is 1 Selected from hydrogen, straight-chain or branched C 1 ～C 5 Alkylamine and straight-chain or branched C 1 ～C 5 A hydroxyalkyl group.
2. The photoresist stripper composition according to claim 1, wherein the first amine compound represented by chemical formula 1 is one or a mixture of two or more selected from the group consisting of 1-amino-2-propanol, 1- [ (2-aminoethyl) amino ] -2-propanol and 1, 1-iminodi-2-propanol.
3. The stripping liquid composition for removing photoresist as claimed in claim 1, wherein the stripping liquid composition further comprises a second amine compound satisfying the following relation 1, a second polar solvent satisfying the following relation 2, and a mixture thereof,
relation 1
A1 bp <A2 bp
In the relation 1, the A1 bp At the boiling point temperature of the first amine compound, the A2 bp Is the boiling temperature of the second amine compound,
relation 2
S1 bp <S2 bp
In the relation 2, the S1 bp Is the boiling point temperature of the first polar solvent, the S2 bp Is the boiling temperature of the second polar solvent.
4. The resist removing stripper composition according to claim 3, wherein the first amine compound is 1-amino-2-propanol or 1- [ (2-aminoethyl) amino ] -2-propanol, and the second amine compound is any one or a mixture of two or more selected from the group consisting of monoethanolamine, 2- (2-aminoethoxy) ethanol, diethanolamine, 3-amino-1-propanol and N- (2-aminoethyl) ethanolamine.
5. The resist removing stripper composition according to claim 3, wherein the first polar solvent is dipropylene glycol monomethyl ether, and the second polar solvent is any one or a mixture of two or more selected from diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol t-butyl ether, triethylene glycol t-butyl ether, diethylene glycol monohexyl ether, triethylene glycol monoethyl ether, triethylene glycol monomethyl ether, and polyethylene glycol.
6. The stripping liquid composition for photoresist removal according to claim 1 or 3, wherein the stripping liquid composition further comprises any one selected from the group consisting of anticorrosive agents and deionized water or a mixture thereof.
7. The stripping liquid composition for removing photoresist as claimed in claim 6, wherein the anticorrosive is any one or a mixture of two or more selected from triazole-based compounds and gallate-based compounds.
8. The stripping liquid composition for removing photoresist as claimed in claim 1, further comprising a second polar solvent 1 to 20 wt% satisfying the following relation 1,1 to 30 wt% satisfying the following relation 2, and a mixture thereof, based on the total weight of the stripping liquid composition:
relation 1
A1 bp <A2 bp
In the relation 1, the A1 bp Boiling for the first amine compoundPoint temperature, A2 bp Is the boiling temperature of the second amine compound,
relation 2
S1 bp <S2 bp
In the relation 2, the S1 bp Is the boiling point temperature of the first polar solvent, the S2 bp Is the boiling temperature of the second polar solvent.
9. The stripping liquid composition for removing photoresist as claimed in claim 8, further comprising any one selected from the group consisting of 0.01 to 5% by weight of an anticorrosive agent and 1 to 40% by weight of deionized water or a mixture thereof, in the total weight of the stripping liquid composition.
10. A method of stripping photoresist, comprising:
a step of forming a photoresist pattern on the substrate on which the lower film is formed;
a step of patterning the lower film using the photoresist pattern; and
a step of stripping a photoresist using the stripping liquid composition as claimed in any one of claims 1 to 5.
11. A method of stripping photoresist, comprising:
a step of forming a photoresist pattern on the substrate on which the lower film is formed;
patterning the lower film using the photoresist pattern; and
a step of stripping a photoresist using the stripping liquid composition as claimed in claim 6.
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| KR1020180020986A KR102512488B1 (en) | 2017-03-03 | 2018-02-22 | Photoresist stripper composition |
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