CN108535971A - Photoresist removal remover composition - Google Patents
Photoresist removal remover composition Download PDFInfo
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- CN108535971A CN108535971A CN201810178861.7A CN201810178861A CN108535971A CN 108535971 A CN108535971 A CN 108535971A CN 201810178861 A CN201810178861 A CN 201810178861A CN 108535971 A CN108535971 A CN 108535971A
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- photoresist
- remover composition
- chemical formula
- amine compounds
- polar solvent
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/42—Stripping or agents therefor
- G03F7/422—Stripping or agents therefor using liquids only
- G03F7/425—Stripping or agents therefor using liquids only containing mineral alkaline compounds; containing organic basic compounds, e.g. quaternary ammonium compounds; containing heterocyclic basic compounds containing nitrogen
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- General Physics & Mathematics (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
Abstract
The present invention relates to a kind of anticorrosive additive stripping liquid controlling compositions, more specifically, it is related to that the dissolving power not comprising harmful toxicant, the resist being stripped is excellent and problem in the processes such as plugged filter can be made to minimize and the corrosion of metal wiring is made to minimize photoresist removal remover composition.
Description
Technical field
The present invention relates to anticorrosive additive stripping liquid controlling compositions, more specifically, are related to not including harmful toxic substance
Matter, the dissolving power for the resist being stripped are excellent and the problem in the processes such as plugged filter can be made to minimize and make metal
The photoresist removal remover composition that the corrosion of wiring minimizes.
Background technology
Photo-mask process is that the pattern by design in mask (mask) is transferred on the substrate for being formed with the film to be processed
A series of photos process.
More specifically, film is formed on substrate, is equably coated with the light as photosensitive material on the above-mentioned films
Resist is caused, mask is configured on the substrate for being coated with above-mentioned photoresist and is exposed (exposure), it then will be above-mentioned
Development of photoresist (develop) and form photoresist pattern.Above-mentioned film is also referred to as lower film, such as can be
Insulating films such as the conductive metal film of aluminium, aluminium alloy, copper, copper alloy, molybdenum and molybdenum alloy etc., silicon oxide film, silicon nitride film etc..
Above-mentioned photoresist pattern can be etched by wet type or dry type using mask, by fine circuit pattern
It transfers and is etched.The process that can be removed via the photoresist that will remain on film after such patterning process,
Photoresist removal stripper (stripper) composition is used thus.
Wherein, the photoresist removal stripper utilized in the process of display and semiconductor telegraph circuit is formed
Photoresist should can be removed in the short time at low temperature, washing on (rinse) metacoxal plate should not there are photoresists
Agent residue, while should have the ability that can not be removed with damaging to organic insulating film and metal wiring.
KR published patent the 10-2011-0124955th, KR published patent the 10-2014-0028962nd and South Korea
During publication the 10-2015-0102354th is equal, as photoresist removal stripper, amine compounds, alkylene are used
The organic compound of base glycol alkyl ether compound, aprotic polar solvent and anticorrosive etc, wherein always using stripping
Property and the excellent N-METHYLFORMAMIDE (N-methylforamide of anticorrosive property；NMF), N-Methyl pyrrolidone (N-
methylpyrrolidone；) etc. NMP non-protonic solvents are as main solvent.Although such solvent exists with excellent
The advantages of peeling force, but it is the substance for showing genotoxicity, have the shortcomings that it is harmful to environment and human body, therefore its use by
Gradually it is restricted.Therefore actual conditions are, it is desirable that develop the stripping with excellent peeling force without using NMF and NMP
Liquid composition, but do not develop the remover composition for showing sufficient peeling force and washing force yet so far actually.
Moreover, there are the following problems for the remover composition comprising above-mentioned NMF and NMP：With time going by, amine compounds
The decomposition of object is promoted, to peeling force and washing force etc. through when decline.With the access times of remover composition, residual light
When a part for resist being caused to be dissolved in remover composition, this problem may be further aggravated.
Due to this problem, has studied instead of above-mentioned NMF and include N, other poles such as N'- dimethylformamides (DMF)
Property aprotic solvent remover composition, but known above-mentioned DMF also shows organismal toxicity, therefore will produce using restricting
Necessity.
Therefore actual conditions are not developed veritably so far while the solvent not comprising display organismal toxicity
Through when maintain the remover composition of excellent peeling force and washing force.
Consider such actual conditions, in the past in order to through when maintain excellent peeling force and washing force, used and removed
Include the method for excessive amine compounds in liquid composition, but in this case, the economy and efficiency of process may substantially reduce,
And the environment caused by excessive amine compounds or the problem in process may occur.
Existing technical literature
Patent document
KR published patent the 10-2011-0124955th
KR published patent the 10-2014-0028962nd
KR published patent the 10-2015-0102354th
Invention content
The present invention to solve the above-mentioned problems, for the purpose of using the solvent harmless to environment and human body, it is intended that
There is provided using such solvent can at low temperature in the short time stripping photoresist and can more improve stripping
Speed, and do not stay photoresist residue on substrate after washing (rinse), while organic insulating film and metal can be matched
The photoresist removal remover composition that line is removed with not damaging.
In addition, it is therefore intended that, the photoresist removal remover composition of ongoing change excellent in stability is provided.
More specifically, it is therefore intended that, it is molten by using N- ethyl-formamides (NEF) and the polarity comprising hydrophobic group
Agent, to which the dissolving power for providing resist that is harmless to environment and human body and can making peeling force and be stripped is maximumlly photic
Resist removal remover composition.
In addition, it is therefore intended that, provide that water substituting is more excellent and the photoresist of ongoing change excellent in stability is gone
Except using remover composition.
In addition, it is therefore intended that, the stripping of the photoresist using photoresist removal remover composition is provided
Method.
The present invention for achieving the above object is related to a kind of photoresist removal remover composition, wherein packet
Ethyl-formamide containing N-, the first amine compounds represented by following chemical formula 1 and the first polarity represented by following chemical formula 2 are molten
Agent.
[chemical formula 1]
In above-mentioned chemical formula 1, above-mentioned R1C selected from hydrogen, linear chain or branched chain1~C5The C of alkylamine and linear chain or branched chain1~C5
Hydroxy alkyl.
[chemical formula 2]
In above-mentioned chemical formula 2, above-mentioned R2C selected from hydrogen, linear chain or branched chain1~C5Alkyl, above-mentioned n are in 1 to 3
Natural number.
In the mode of the present invention, the first amine compounds represented by above-mentioned chemical formula 1 can be selected from 1- amino -2- third
Alcohol, 1- [(2- amino-ethyls) amino] any one of -2- propyl alcohol and 1,1- imino-diacetic -2- propyl alcohol or two or more mixing
Object.
In the mode of the present invention, the first polar solvent represented by above-mentioned chemical formula 2 can be selected from dipropylene glycol list
Any one of methyl ether, dihydroxypropane single-ethyl ether, dipropylene glycol list propyl ether and dipropylene glycol mono butyl base ether or two kinds with
On mixture.
In the mode of the present invention, above-mentioned remover composition, which can further include, meets the second of following relational expressions 1
Amine compounds, the second polar solvent and their mixture for meeting following relational expressions 2.
[relational expression 1]
A1bp<A2bp
In above-mentioned relation formula 1, above-mentioned A1bpFor the boiling temperature of the first amine compounds, above-mentioned A2bpFor the second amine compounds
Boiling temperature.
[relational expression 2]
S1bp<S2bp
In above-mentioned relation formula 2, above-mentioned S1bpFor the boiling temperature of the first polar solvent, above-mentioned S2bpFor the second polar solvent
Boiling temperature.
In the mode of the present invention, above-mentioned first amine compounds can be 1- amino -2- propyl alcohol or 1- [(2- amino-ethyls)
Amino] -2- propyl alcohol, above-mentioned second amine compounds can be selected from monoethanolamine, 2- (2- amino ethoxies) ethyl alcohol, diethanol
Any one of amine, 3- amino -1- propyl alcohol and N- (2- amino-ethyls) ethanol amine or two or more mixtures.
In the mode of the present invention, above-mentioned first polar solvent can be dipropylene glycol monomethyl ether, above-mentioned second polarity
Solvent can be selected from diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, the tertiary fourth of diethylene glycol
Base ether, triethylene glycol tertbutyl ether, diethylene glycol monohexyl ether, triethylene glycol monoethyl ether, triethylene glycol monomethyl ether and poly-
Any one of ethylene glycol or two or more mixtures.
In the mode of the present invention, above-mentioned remover composition can be further included selected from anticorrosive and deionized water
Any one of or their mixture.
In the mode of the present invention, above-mentioned anticorrosive can be in three azole compounds and gallic acid ester based compound
Any one or more mixtures.
Can include above-mentioned N- ethyl-formamides in above-mentioned remover composition total weight in the mode of the present invention
10 to 90 weight %, more specifically 20~85 weight %, 1 to 50 weight % of the first amine compounds represented by above-mentioned chemical formula 1,
More specifically 3 to 30 weight %, 1 to 50 weight % of the first polar solvent represented by above-mentioned chemical formula 2, more specifically 5 to 40
Weight %.
In the mode of the present invention, in above-mentioned remover composition total weight, it can further include and meet following passes
Be 1 to the 20 weight % of the second amine compounds of formula 1, meet following relational expressions 21 to 30 weight % of the second polar solvent and they
Mixture.
[relational expression 1]
A1bp<A2bp
In above-mentioned relation formula 1, above-mentioned A1bpFor the boiling temperature of the first amine compounds, above-mentioned A2bpFor the second amine compounds
Boiling temperature.
[relational expression 2]
S1bp<S2bp
In above-mentioned relation formula 2, above-mentioned S1bpFor the boiling temperature of the first polar solvent, above-mentioned S2bpFor the second polar solvent
Boiling temperature.
In the mode of the present invention, in above-mentioned remover composition total weight, it can further include selected from anticorrosion
Any one of 1 to 40 weight % of 0.01 to 5 weight % of agent and deionized water or their mixture.
In addition, the present invention relates to a kind of stripping means of photoresist comprising：
In the step of forming photoresist pattern on the substrate for be formed with lower film；
Using above-mentioned photoresist pattern by the patterned step of lower film；And
The step of photoresist is removed using above-mentioned remover composition.
Even if the photoresist removal remover composition of the present invention is not used to environment and the harmful N- first of human body
Base formamide (N-methylforamide；) and N-Methyl pyrrolidone (N-methylpyrrolidone NMF；NMP) as master
Solvent also can quickly remove photoresist.In addition, even if the photoresist removal remover composition of the present invention exists
Also modified photoresist can be quickly removed after dry type or wet etching.
It is furthermore possible to also provide can at low temperature in the short time stripping photoresist and can more improve stripping speed
Degree, and do not stay photoresist residue on substrate after washing (rinse), while can be to organic insulating film and metal wiring
The photoresist removal remover composition removed with not damaging.
In addition there is following advantage：The dissolving power for the photoresist being stripped is excellent, and plugged filter is made in process not
It is good minimized, so as to dramatically increase process efficiency.
It is furthermore possible to also provide the photoresist removal remover composition of ongoing change excellent in stability.
Specific implementation mode
Hereinafter, photoresist removal is described in detail with remover composition.The present invention relates to display,
The photoresist removal remover composition used in OLED manufactures and semiconductor manufacturing, can be by following embodiments
More fully understand that the present invention, following embodiments do not limit the protection limited by appended claims for illustrating the present invention
Range.
The present inventor etc. do not use harmful N-METHYLFORMAMIDE (N-methylforami to develop
de；) and N-Methyl pyrrolidone (N-methylpyrrolidone NMF；NMP it) is used as main solvent, and photoresist can be improved
The remover composition of the removal speed of agent and studied, as a result, it has been found that, be used together N- ethyl-formamides, following chemistry
In the case of the first polar solvent represented by the first amine compounds and following chemical formula 2 represented by formula 1, removal can be shortened
The dissolving power of the time that photoresist is consumed, the photoresist being stripped are excellent and can make the process of plugged filter
On problem it is minimized, and ongoing change excellent in stability, thereby completing the present invention.
[chemical formula 1]
In above-mentioned chemical formula 1, above-mentioned R1C selected from hydrogen, linear chain or branched chain1~C5The C of alkylamine and linear chain or branched chain1~C5
Hydroxy alkyl.
[chemical formula 2]
In above-mentioned chemical formula 2, above-mentioned R2C selected from hydrogen, linear chain or branched chain1~C5Alkyl, above-mentioned n are in 1 to 3
Natural number.
Specifically, finding by using N- ethyl-formamides, to solve because using N-METHYLFORMAMIDE (N-
methylforamide；) and N-Methyl pyrrolidone (N-methylpyrrolidone NMF；NMP the environmental problem caused by),
And by being used together as shown in above-mentioned chemical formula 1 and chemical formula 2 comprising hydrophobic isopropylidene with N- ethyl-formamides
(isopropylene) compound of structure, according to their synergistic effect, amine compounds performance is more prone to cut off photic anti-
The effect for losing the cross-bond of agent, can further shorten splitting time, and can realize and use in the past the composition of NMF, NMP
Same or superior peeling rate, thereby completing the present invention.It is found furthermore that not only peeling force is excellent but also is stripped against corrosion
The dissolving power of agent is excellent, ongoing change excellent in stability, thereby completing the present invention.
It is found furthermore that other than the first amine compounds represented by above-mentioned chemical formula 1, in above-mentioned composition further
Including high boiling second amine compounds compared with the first amine compounds, so as to further increase ongoing change stability.
It is found furthermore that other than the first polar solvent represented by above-mentioned chemical formula 2, in above-mentioned composition further
Including higher boiling and hydrophilic second polar solvent compared with the first polar solvent, so as to further increase water displacement
Property.
Hereinafter, one embodiment of the invention is described in more detail.
The 1st aspect of the present invention includes the first amine compounds and chemical formula represented by N- ethyl-formamides, chemical formula 1
The first polar solvent represented by 2.
The 2nd aspect of the present invention includes the first amine compounds, the chemical formula 2 represented by N- ethyl-formamides, chemical formula 1
The first represented polar solvent and anticorrosive.
The 3rd aspect of the present invention includes the first amine compounds represented by N- ethyl-formamides, chemical formula 1.Chemical formula 2
The first represented polar solvent and ultra-pure water or deionized water.
The 4th aspect of the present invention includes the first amine compounds, the chemical formula 2 represented by N- ethyl-formamides, chemical formula 1
Represented the first polar solvent, anticorrosive and ultra-pure water or deionized water.
The 5th aspect of the present invention includes the first amine compounds, the chemical formula 2 represented by N- ethyl-formamides, chemical formula 1
Represented the first polar solvent and the second amine compounds for meeting following relational expressions 1.
[relational expression 1]
A1bp<A2bp
In above-mentioned relation formula 1, above-mentioned A1bpFor the boiling temperature of the first amine compounds, above-mentioned A2bpFor the second amine compounds
Boiling temperature.
The 6th aspect of the present invention includes the first amine compounds, the chemical formula 2 represented by N- ethyl-formamides, chemical formula 1
Represented the first polar solvent and the second polar solvent for meeting following relational expressions 2.
[relational expression 2]
S1bp<S2bp
In above-mentioned relation formula 2, above-mentioned S1bpFor the boiling temperature of the first polar solvent, above-mentioned S2bpFor the second polar solvent
Boiling temperature.
The 7th aspect of the present invention includes the first amine compounds, the chemical formula 2 represented by N- ethyl-formamides, chemical formula 1
Represented the first polar solvent meets the second amine compounds of above-mentioned relation formula 1 and meets the second polarity of above-mentioned relation formula 2
Solvent.
The 8th aspect of the present invention includes the first amine compounds, the chemical formula 2 represented by N- ethyl-formamides, chemical formula 1
Represented the first polar solvent, the second amine compounds and anticorrosive for meeting above-mentioned relation formula 1.
The 9th aspect of the present invention includes the first amine compounds, the chemical formula 2 represented by N- ethyl-formamides, chemical formula 1
Represented the first polar solvent, the second polar solvent and anticorrosive for meeting above-mentioned relation formula 2.
The 10th aspect of the present invention includes the first amine compounds, the chemical formula 2 represented by N- ethyl-formamides, chemical formula 1
Represented the first polar solvent meets the second amine compounds of above-mentioned relation formula 1, meets the second polarity of above-mentioned relation formula 2
Solvent and anticorrosive.
Above-mentioned first method to the tenth mode is only intended to the mode of the particular instantiation present invention and is not limited to this.This
Outside, as needed, additive usually used in this field can be further included.
In the mode of the present invention, there is no limit, can be with but in all compositions content for above-mentioned N- ethyl-formamides content
Including 10 to 90 weight %.It can more preferably include 20 to 85 weight %, more appropriately include 40 to 85 weight %.In above-mentioned model
When enclosing, peeling force can be improved and significantly shorten the photoresist removal time, and lower part erosion can be made to minimize.
In the mode of the present invention, the first amine compounds represented by above-mentioned chemical formula 1 are by acting on the light being modified
Weaker part in the surface of resist is caused, so as to play the effect for being easy to make solvent composition to permeate.In addition, by with
The first polar solvent represented by above-mentioned N- ethyl-formamides and above-mentioned chemical formula 2 is used together, to harmless and
Play the maximized outstanding role of photoresist dissolving power for making peeling force and being stripped.In addition, with ongoing change is improved
The effect of stability.
The first amine compounds represented by above-mentioned chemical formula 1, which are specifically as follows, is selected from such as 1- amino -2- propyl alcohol, 1- [(2-
Amino-ethyl) amino] -2- propyl alcohol and 1, any one of 1- imino-diacetic -2- propyl alcohol etc. or two or more mixtures, but not
It is limited to this.
On the basis of the total weight of photoresist removal remover composition, first represented by above-mentioned chemical formula 1
The content of amine compounds can be 1 to 50 weight %.More preferably can include 3 to 30 weight %, more appropriately can include 5 to
15 weight %.By including with above range, so as to significantly improve the peeling force of the photoresist for being modified.
In the mode of the present invention, the first polar solvent represented by above-mentioned chemical formula 2 is comprising as hydrophobic group
Isopropylidene diatomic alcohol compounds, it is excellent for the wetability of photoresist, therefore stripping can not only be significantly improved
Power and the dissolving power that the photoresist being stripped can be significantly improved.
The first polar solvent represented by above-mentioned chemical formula 2 by with 1 institute of above-mentioned N- ethyl-formamides and above-mentioned chemical formula
The first amine compounds indicated are used together, the photoresist for making peeling force to harmless and performance and being stripped
The maximized outstanding role of dissolving power.In addition, having the effect of improving ongoing change stability.
The first polar solvent represented by above-mentioned chemical formula 2 is specifically as follows selected from such as propylene glycol monomethyl ether, the third two
Alcohol list ethylether, propylene glycol monopropyl ether, glycol monobutyl ether, dipropylene glycol monomethyl ether, dihydroxypropane single-ethyl ether, two
Propylene glycol monopropyl ether, dipropylene glycol mono butyl base ether, tripropylene glycol monomethyl ether, tripropylene glycol list ethylether, tripropylene glycol list
Any one of propyl ether and tripropylene glycol monobutyl base ether etc. or two or more mixtures.
More appropriately can be selected from dipropylene glycol monomethyl ether, dihydroxypropane single-ethyl ether, dipropylene glycol list propyl ether
With any one of dipropylene glycol mono butyl base ether or two or more mixtures.
On the basis of the total weight of photoresist removal remover composition, first represented by above-mentioned chemical formula 2
The content of polar solvent can be 1 to 50 weight %.It more preferably can include 5 to 40 weight %, more appropriately can include 15
To 30 weight %.By including with above range, to be shown using harmless aprotic polar solvent
It writes the peeling force of raising photoresist and the dissolving power for the photoresist being stripped and promotes process efficiency.
In the mode of the present invention, above-mentioned photoresist removal remover composition is in addition to 1 table of above-mentioned chemical formula
Amine compounds usually used in this field can be further included except the first amine compounds shown.
More appropriately, high compared with above-mentioned first amine compounds by further including as shown in following relational expressions 1
Second amine compounds of boiling point, ongoing change stability is more improved so as to further decrease volatility.
[relational expression 1]
A1bp<A2bp
In above-mentioned relation formula 1, above-mentioned A1bpFor the boiling temperature of the first amine compounds, above-mentioned A2bpFor the second amine compounds
Boiling temperature.
More specifically, for example, by comprising boiling point than high 1 DEG C of above-mentioned first amine compounds or more, more appropriately high by 10
DEG C or more amine compounds as the second amine compounds, so as to further increase ongoing change stability.
The concrete example of above-mentioned second amine compounds can be selected from monoethanolamine, 2- (2- amino ethoxies) ethyl alcohol, diethyl
Any one of hydramine, 3- amino -1- propyl alcohol and N- (2- amino-ethyls) ethanol amine etc. or two or more mixtures, but it is unlimited
In this.More appropriately can be 2- (2- amino ethoxies) ethyl alcohol and diethanol amine.
More specifically, such as above-mentioned first amine compounds can be 1- amino -2- propyl alcohol or 1- [(2- amino-ethyls) ammonia
Base] -2- propyl alcohol, above-mentioned second amine compounds can be selected from monoethanolamine, 2- (2- amino ethoxies) ethyl alcohol, diethanol amine,
Any one of 3- amino -1- propyl alcohol and N- (2- amino-ethyls) ethanol amine or two or more mixtures.
On the basis of the total weight of photoresist removal remover composition, the content of above-mentioned second amine compounds can
Think 1 to 50 weight %.It can include more preferably 1 to 20 weight %, more appropriately can include 3 to 10 weight %.By with
Above range includes, so as to not hinder above-mentioned peeling force and solvent while further increasing ongoing change and stablize
Property.
In the mode of the present invention, above-mentioned photoresist removal remover composition is in addition to 2 tables of above-mentioned chemical formula
Polar solvent usually used in this field can be further included except the first polar solvent shown.
More appropriately, high compared with above-mentioned first polar solvent by further including as shown in following relational expressions 2
Second polar solvent of boiling point, so as to further increase water substituting.
[relational expression 2]
S1bp<S2bp
In above-mentioned relation formula 2, above-mentioned S1bpFor the boiling temperature of the first polar solvent, above-mentioned S2bpFor the second polar solvent
Boiling temperature.
More specifically, for example, by comprising boiling point than high 1 DEG C of above-mentioned first polar solvent or more, more appropriately high by 10
DEG C or more polar solvent as the second polar solvent, so as to further increase water substituting.More appropriately, it can use
Boiling point height and the polar solvent of polarity bigger due to not comprising isopropylidene structure as shown in above-mentioned relational expression 2.
The concrete example of above-mentioned second polar solvent can be selected from diethylene glycol monomethyl ether, diethylene glycol monoethyl ether,
Diethylene glycol monobutyl ether, diethylene glycol tertbutyl ether, triethylene glycol tertbutyl ether, diethylene glycol monohexyl ether, triethylene glycol
Any one of single ethylether, triethylene glycol monomethyl ether and polyethylene glycol etc. or two or more mixtures, but be not limited to
This.More appropriately can be diethylene glycol monobutyl ether, diethylene glycol monoethyl ether, diethylene glycol monohexyl ether, triethylene glycol
Single ethylether, triethylene glycol monomethyl ether and polyethylene glycol.
More specifically, such as above-mentioned first polar solvent can be dipropylene glycol monomethyl ether, and above-mentioned second polarity is molten
Agent can be selected from diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol tertiary butyl
Ether, triethylene glycol tertbutyl ether, diethylene glycol monohexyl ether, triethylene glycol monoethyl ether, triethylene glycol monomethyl ether and poly- second
Any one of glycol or two or more mixtures.
On the basis of the total weight of photoresist removal remover composition, the content of above-mentioned second polar solvent can
Think 1 to 50 weight %.It can include more preferably 1 to 30 weight %, more appropriately can include 10 to 20 weight %.By with
Above range includes, so as to not hinder peeling force and solvent while further increasing water substituting.
In the mode of the present invention, above-mentioned photoresist removal remover composition can include anticorrosive, only
If anticorrosive usually used in this field can use without limitation, such as triazole compounds can be specifically used
With gallate ester compounds etc..Above-mentioned anticorrosive can be easy dissolving in stripper, and play conduct in DI washing procedures
The effect of oxidant and complex compound, to inhibit the electrochemical effect caused by organic amine (Galvanic effect) and
Eliminate the feature of the corrosion impact for metal wiring.
There is no limit can specifically make above-mentioned triazole compounds as long as well known compound apparent in the art
With selected from such as benzotriazole, o-tolyl triazole, tolyl-triazole, p-methylphenyl triazole, carboxyl benzotriazole, 1- hydroxyls
Any one of benzotriazole, nitrobenzene and triazolam, dihydroxypropyl benzotriazole and tetrahydrochysene tolyl-triazole etc. or two kinds with
On mixture, but it is not limited to this.
Just there is no limit as long as compound apparent well known in the art for above-mentioned gallate ester compounds, specifically can be with
Using pungent selected from such as methyl gallate, ethyl gallate, propyl gallate, gallate isopropyl ester, gallate butyl ester, the gallate tert-butyl ester and gallate
Any one of ester etc. or two or more mixtures, but it is not limited to this.
In above-mentioned photoresist removal remover composition, the content of above-mentioned anticorrosive can not hinder it is photic
It is used in the range of the physical property of resist removal remover composition, can include 0.01 to 5 weight %, it more appropriately can be with
Including 0.05 to 2 weight %, can include more appropriately 0.1 to 0.5 weight %, but it is not limited to this.
In addition, the photoresist removal remover composition of the present invention can be as needed other than mentioned component
The additional additive usually added without limitation, specifically, can further include selected from such as water substituting enhancer,
The additive of one or more of surfactant, antifoaming agent and their mixture.
That is, in order to improve the uniformity of cleaning, surfactant can be further added in composition of the invention, in order to
Inhibit to interfere the bubble of cleaning to occur, antifoaming agent can be used as additive.Although there is no limit opposite for the amount of additive
In above-mentioned photoresist removal 100 parts by weight of remover composition total weight, can with below 20 parts by weight, preferably with 5
Parts by weight content below includes additive, but not limited to this.On the other hand, the example of workable surfactant and antifoaming agent
Son is commonly known in the art, for example, as surfactant, can use amphoteric, cationic, anion
Type, nonionic or fluorine system surfactant can use silicon systems or non-silicon systems antifoaming agent as antifoaming agent.
In the mode of the present invention, above-mentioned photoresist removal remover composition can be water system or non-water system group
Close object.
In order to which water system composition is made, deionized water can be further included.Above-mentioned deionized water can with ultra-pure water,
The identical meaning such as Purified Water uses, can be in the range of not hindering the physical property of photoresist removal remover composition
It uses, although there is no limit can include more specifically 1 to 40 weight %, can include specifically further 2 to 15 weight %.
In addition, still another embodiment according to the present invention, can be provided with above-mentioned photoresist removal stripper group
Close the stripping means for the photoresist that object is handled.
The stripping means of above-mentioned photoresist may include：It will be formed in comprising organic insulating film, metal wiring or gold
Belong to the photoresist pattern on the substrate of the lower films such as wiring and inorganic material layer as mask, place is etched to substrate
Reason, stripping (stripping) step for being removed photoresist with above-mentioned photoresist removal remover composition.
More specifically, may include：In the step of forming photoresist pattern on the substrate for be formed with lower film；Profit
With above-mentioned photoresist pattern by the patterned step of lower film；And photoresist is shelled using above-mentioned remover composition
From the step of.
In such stripping means, it is possible, firstly, on the substrate for the lower film for being formed with desirable pattern, pass through photoetching work
Sequence forms photoresist pattern.Later, lower film can be patterned using such photoresist pattern as mask
Afterwards, photoresist is removed using above-mentioned remover composition etc..In above-mentioned operation, the formation of photoresist pattern and under
The patterning process of portion's film can be according to common element manufacturing process, therefore omits the additional explanation to this.
On the other hand, when being removed photoresist using above-mentioned remover composition, it is possible, firstly, to above-mentioned stripper
Composition is handled on the substrate of residual pattern, is cleaned using alkaline buffer solution, and ultra-pure water is used
Cleaning, and carry out drying process.
Using the photoresist remover composition of one embodiment of the invention from the base for being carved with fine circuit pattern
The method that plate removes photoresist can use such as under type：It is more that (dipping) is impregnated in a large amount of stripper simultaneously
Open the impregnation method of the substrate to be removed；And it sprays stripper to individual substrate and removes the single sheet type side of photoresist
Formula, but it is not limited to this.
Kind as the photoresist that can be removed with remover composition using the photoresist of the present invention
Class may include such as positive light anti-etching agent, negative type photoresist and eurymeric/minus dual-purpose photoresist (dual
Tone photoresist) etc..Although in addition, for its constituent, there is no limit can be especially effectively applicable photic
Resist can be the photoresist being made of the Photoactive compounds comprising phenolic varnish type phenolic resin and diazo naphthoquinone.
About the metal wiring that can be applicable in above-mentioned photoresist removal remover composition, such as lower part
Film, can include Al, Cu, Ag, Ti and Mo etc., they can be used as p-electrode and n-electrode to use, and but it is not limited to this.
Hereinafter, the preferred embodiment to the photoresist removal remover composition of the present invention and performance measurement
Method is described in detail.
1) photoresist peeling force is evaluated
For the photoresist removal remover composition manufactured as described in Table 1, in order to evaluate photoresist
Agent stripping performance, on the glass substrate with 1.5 μm of thickness painting photoresist (AZEM, DTR-300), then at 160 DEG C
10 minutes hard baking (hard bake are carried out respectively with 170 DEG C；H/B), to preparing experiment test piece.Utilize 60 DEG C of temperature of maintenance
The peel-off device of single sheet type spray discharge pattern, under the conditions of the atomisation pressure of 0.4kgf, it is complete that measurement photoresist is stripped liquid
Time needed for stripping, and evaluation result is shown in following table 2.
At this point, irradiating whether observation photoresist after ultraviolet light remains on the glass substrate, to confirm photoresist
Whether agent is stripped.
2) dissolving power is evaluated
For the photoresist removal remover composition manufactured as described in Table 1, in order to evaluate photoresist
Agent dissolving power, it is in 150 DEG C of heating plates that photoresist (AZEM, DTR-300) is 4 hours dry, to manufacture photoresist
Powder.Dry photoresist powder is put into the remover composition of 60 DEG C of temperature constant states under 300rpm stirring conditions
2 weight % simultaneously stir 20 minutes to make it dissolve, and 10 μm of filters (PTFE that stomata is 10 μm) are then made it through, to comment
Valence dissolving power.2 weight % of photoresist is completely dissolved in 20 minutes and measures after filtering and is set as less than the case where surplus
More than 100%, it is believed that more there is high level, more photoresists can be dissolved, therefore handling number.Dissolving power can
To be calculated according to following formula.
Dissolving power (%)=[(filter is remained on for the content-of 2 weight % of the solid constituent photoresists used
Photoresist content)/for the content of 2 weight % of the solid constituent photoresists used] × 100
3) lower film corrosion evaluation
Using the peel-off device for the single sheet type spray discharge pattern for maintaining 60 DEG C of temperature, under the conditions of the atomisation pressure of 0.4kgf,
After being completely exfoliated with the stripper of embodiment and comparative example, for dry test piece, by the light microscopes of 200 multiplying powers and
The FE-SEM of 10K~50K multiplying powers confirms lower film degree of injury.It the results are shown in following table 2.
◎：Do not corrode
○：Mild corrosion occurs
△：Corrode
X：Heavy corrosion occurs
4) ongoing change estimation of stability
(1) peeling force is evaluated after ongoing change
In order to evaluate ongoing change stability, using with above-mentioned 1) identical method, evaluate remover composition through when
Peeling force after variation.It the results are shown in following table 2.
Prepare the remover composition 500g manufactured in embodiment and comparative example, in the state of being warming up to 60 DEG C, input
Relative to the photoresist (AZEM, DTR-300) that all compositions is 2 weight % and dissolve.By above-mentioned stripper with 60 DEG C
It heats 12 to 48 hours and causes the ongoing change under harsh conditions.
For the remover composition via such ongoing change, removed using being measured with above-mentioned 1) identical method
Power, to evaluate ongoing change stability.
(2) dissolving power is evaluated after ongoing change
Photoresist (AZEM, DTR-300) is dried 4 hours in 150 DEG C of heating plates and manufactures photoresist powder.
Dry 2 weight of photoresist powder is put into the remover composition of 60 DEG C of temperature constant states under 300rpm stirring conditions
It measures % and stirs 20 minutes to make it dissolve.By above-mentioned stripper with 60 DEG C are heated 12 to 48 hours and are caused under harsh conditions
Ongoing change.
As it is above-mentioned 2), making filter that the remover composition via such ongoing change passes through 1 μm, (stomata is
1 μm of PTFE), to evaluate dissolving power.
Dissolving power (%)=[(filter is remained on for the content-of 2 weight % of the solid constituent photoresists used
Photoresist content)/for the content of 2 weight % of the solid constituent photoresists used] × 100
5) water replaces degree evaluation
Final step includes the steps that washing with water in photoresist stripping process.Therefore, including remaining on substrate
The stripper of photoresist should be good for the water substituting of water, has carried out the evaluation for being able to confirm that the water substituting.
The substrate after being impregnated 1 minute in stripper is taken out, using air knife, by over-drying 1 minute of stripper.It will pass through
After the dry substrate of degree rinses in water, the speckle of substrate is with the naked eye confirmed.The good composition of water substituting, speckle
Intensity is weaker, and the results are shown in following table 2
◎：It is very good
○：Well
△：Speckle occurs
X：Serious speckle occurs
6) volatility
In order to confirm volatility, after putting into composition 500g into 1L beakers, it is put into 60 DEG C of thermostats.Later, 24 are measured
Weight after hour calculates volatility according to following formula.
Volatility=[(weight (g) of existing composition)-(weight (g) of the existing composition after 24 hours)]/existing
Weight (g) × 100 of composition
[embodiment and comparative example]
Ingredient and composition recorded in following table 1 are mixed and manufacture photoresist removal remover composition.
At this point, mixing is to carry out at normal temperatures, is mixed in a manner of it can fully dissolve 1 hour or more, then Teflon is utilized to filter
Device (Teflon filter, the PTFE that stomata is 1 μm) uses after being filtered.
[table 1]
<Solvent>
NEF：N- ethyl-formamides
NMF：N-METHYLFORMAMIDE
<First amine compounds>
MIPA：1- amino -2- propyl alcohol
HEA：1- [(2- amino-ethyls) amino] -2- propyl alcohol
IDP：1,1- imino-diacetic -2- propyl alcohol
<Second amine compounds>
MEA：Monoethanolamine
AEE：2- (2- amino ethoxies) ethyl alcohol
DEA：Diethanol amine
3-AP：3- amino -1- propyl alcohol
AEEA：N- (2- amino-ethyls) ethanol amine
<First polar solvent>
DPGME：Dipropylene glycol monomethyl ether
DPGEE：Dihydroxypropane single-ethyl ether
DPEPE：Dipropylene glycol list propyl ether
DPEBE：Dipropylene glycol mono butyl base ether
<Second polar solvent>
MDG：Diethylene glycol monomethyl ether
BDG：Diethylene glycol monobutyl ether
EDG:Diethylene glycol monoethyl ether
TGTB：Triethylene glycol tertbutyl ether
DGTB：Diethylene glycol tertbutyl ether
HDG：Diethylene glycol monohexyl ether
TEG：Triethylene glycol monoethyl ether
TMG：Triethylene glycol monomethyl ether
<Anticorrosive>
H4TT：Tetrahydrochysene tolyl-triazole
TT：Tolyl-triazole
MG：Methyl gallate
EG：Ethyl gallate
PG：Propyl gallate
BG：Gallate butyl ester
OG：Gallate monooctyl ester
In following table 2, △ 12 refers to the physical property measured after 12 hours ongoing change, △ 48 refer to 48 hours through when
The physical property measured after variation.
[table 2]
As shown in Table 2 above, can confirm the present invention photoresist removal not only removed with remover composition speed,
Dissolving power is excellent, and lower part erosion is also all apparent excellent.In addition, understanding ongoing change excellent in stability.
As shown in embodiment 1~11, confirm by the first amine compounds and chemical formula 2 represented by NEF, chemical formula 1
Represented this three of first polar solvent combination and in use, peeling force and dissolving power are most excellent.
In addition, as shown in embodiment 12~16, it is known that even if in the case where further including the second polar solvent, stripping
Power and dissolving power also do not change, and confirm water substituting and further increase.
In addition, as described in Example 17, it is known that in the case where adding deionized water, although peeling force and dissolving power display
Decline compared with other embodiment, but shows superior peeling force and dissolving power compared with comparative example.
In addition, as shown in embodiment 18-20, confirm by comprising anticorrosive, being further reduced the corrosion of lower film
Occur.
In addition, as shown in embodiment 21-23, it is known that even if in the case where further including the second amine compounds, stripping
Power and dissolving power also do not change, and confirm due to volatility is less than embodiment 1 that ongoing change stability further increases.
In addition, as shown in embodiment 24-31, it is known that even if further including the second polar solvent and the second amine compounds
In the case of, peeling force and dissolving power also do not change, and ongoing change stability further increases due to volatility is low, and
Water displacement degree further increases.
As shown in comparative example 1~7, confirm in the case of excluding any ingredient in the present compositions, physical property
Decline.Known to should the reason is that, the first polar solvent represented by chemical formula 2 is to the photoresist as the target for needing to remove
Affinity it is strong and by quick humidification (wetting), the first polar solvent represented by chemical formula 2 is simultaneously by similar structure at this time
Chemical formula 1 represented by the first amine compounds take to photoresist surface to faster remove and dissolve photoresist.
In addition, as shown in comparative example 8~10, confirm in the case where replacing NEF using other amide solvents such as NMP,
Dissolving power declines.
It thereby confirms that, photoresist removal remover composition according to the present invention, even if including harmless
Solvent and amine compounds, the polar solvent containing hydrophobic group, can also provide because of peeling force, dissolving power and ongoing change
Excellent in stability and the remover composition that process efficiency can be improved.
A preferred embodiment of the present invention is explained above, but the present invention can carry out a variety of variations and can use equivalent
Object, it is clear that similarly applied after can suitably changing above-described embodiment.Therefore, above-mentioned contents do not limit by following power
The scope of the present invention that the content of sharp claim determines.
Claims (14)
1. a kind of photoresist removal remover composition is comprising 1 N- ethyl-formamides, following chemical formula table
The first polar solvent represented by the first amine compounds and following chemical formula 2 shown,
Chemical formula 1
In the chemical formula 1, the R1C selected from hydrogen, linear chain or branched chain1~C5The C of alkylamine and linear chain or branched chain1~C5Hydroxyl
Alkyl,
Chemical formula 2
In the chemical formula 2, the R2C selected from hydrogen, linear chain or branched chain1~C5Alkyl, the n are the nature in 1 to 3
Number.
2. photoresist removal remover composition according to claim 1, wherein represented by the chemical formula 1
The first amine compounds be selected from 1- amino -2- propyl alcohol, 1- [(2- amino-ethyls) amino] -2- propyl alcohol and 1,1- imino-diacetics -
Any one of 2- propyl alcohol or two or more mixtures.
3. photoresist removal remover composition according to claim 1, wherein represented by the chemical formula 2
The first polar solvent be selected from dipropylene glycol monomethyl ether, dihydroxypropane single-ethyl ether, dipropylene glycol list propyl ether and dipropyl
Any one of glycol single-butyl ether or two or more mixtures.
4. photoresist removal remover composition according to claim 1, wherein the remover composition is also
Including meeting the second amine compounds of following relational expressions 1, the second polar solvent for meeting following relational expressions 2 and their mixing
Object,
Relational expression 1
A1bp<A2bp
In the relational expression 1, the A1bpFor the boiling temperature of the first amine compounds, the A2bpFor the boiling point of the second amine compounds
Temperature,
Relational expression 2
S1bp<S2bp
In the relational expression 2, the S1bpFor the boiling temperature of the first polar solvent, the S2bpFor the boiling point of the second polar solvent
Temperature.
5. photoresist removal remover composition according to claim 4, wherein first amine compounds are
1- amino -2- propyl alcohol or 1- [(2- amino-ethyls) amino] -2- propyl alcohol, second amine compounds are selected from monoethanolamine, 2-
Any one of (2- amino ethoxies) ethyl alcohol, diethanol amine, 3- amino -1- propyl alcohol and N- (2- amino-ethyls) ethanol amine or two
Kind or more mixture.
6. photoresist removal remover composition according to claim 4, wherein first polar solvent is
Dipropylene glycol monomethyl ether, second polar solvent are selected from diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethyl
Glycol single-butyl ether, diethylene glycol tertbutyl ether, triethylene glycol tertbutyl ether, diethylene glycol monohexyl ether, triethylene glycol list second
Any one of base ether, triethylene glycol monomethyl ether and polyethylene glycol or two or more mixtures.
7. photoresist removal remover composition according to claim 1 or 4, wherein the stripper combination
Object also includes to be selected from any one of anticorrosive and deionized water or their mixture.
8. photoresist removal remover composition according to claim 7, wherein the anticorrosive be selected from
Any one of three azole compounds and gallic acid ester based compound or two or more mixtures.
9. photoresist removal remover composition according to claim 1, wherein in the remover composition
In total weight, including the first amine compounds 1 represented by 10 to 90 weight % of the N- ethyl-formamides, the chemical formula 1 to
1 to 50 weight % of the first polar solvent represented by 50 weight %, the chemical formula 2.
10. photoresist removal remover composition according to claim 9 is comprising the N- ethyls first
Represented by 3 to 30 weight % of the first amine compounds, the chemical formula 2 represented by 20~85 weight % of amide, the chemical formula 1
5 to 40 weight % of the first polar solvent.
11. photoresist removal remover composition according to claim 9, wherein combined in the stripper
Also include 1 to the 20 weight % of the second amine compounds for meeting following relational expressions 1, meet following relational expressions 2 the in object total weight
Two polar solvents, 1 to 30 weight % and their mixture,
Relational expression 1
A1bp<A2bp
In the relational expression 1, the A1bpFor the boiling temperature of the first amine compounds, the A2bpFor the boiling point of the second amine compounds
Temperature,
Relational expression 2
S1bp<S2bp
In the relational expression 2, the S1bpFor the boiling temperature of the first polar solvent, the S2bpFor the boiling point of the second polar solvent
Temperature.
12. the photoresist removal remover composition according to claim 9 or 11, wherein in the stripper
Also include selected from any one of 1 to 40 weight % of 0.01 to 5 weight % of anticorrosive and deionized water in composition total weight
Or their mixture.
13. a kind of stripping means of photoresist comprising：
In the step of forming photoresist pattern on the substrate for be formed with lower film；
Using the photoresist pattern by the patterned step of lower film；And
The step of photoresist is removed using the remover composition described in any one of claim 1 to 6.
14. a kind of stripping means of photoresist comprising：
In the step of forming photoresist pattern on the substrate for be formed with lower film；
Using above-mentioned photoresist pattern by the patterned step of lower film；And
The step of photoresist is removed using the remover composition described in claim 7.
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| KR10-2017-0027592 | 2017-03-03 | ||
| KR20170027592 | 2017-03-03 | ||
| KR1020180020986A KR102512488B1 (en) | 2017-03-03 | 2018-02-22 | Photoresist stripper composition |
| KR10-2018-0020986 | 2018-02-22 |
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