CN1249530C - Alkoxyl N-hydroxy alkyl acylamine used as corrosion inhibitor remover - Google Patents
Alkoxyl N-hydroxy alkyl acylamine used as corrosion inhibitor remover Download PDFInfo
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- CN1249530C CN1249530C CNB991119657A CN99111965A CN1249530C CN 1249530 C CN1249530 C CN 1249530C CN B991119657 A CNB991119657 A CN B991119657A CN 99111965 A CN99111965 A CN 99111965A CN 1249530 C CN1249530 C CN 1249530C
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/42—Stripping or agents therefor
- G03F7/422—Stripping or agents therefor using liquids only
- G03F7/425—Stripping or agents therefor using liquids only containing mineral alkaline compounds; containing organic basic compounds, e.g. quaternary ammonium compounds; containing heterocyclic basic compounds containing nitrogen
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
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Abstract
The present invention relates to a sort of resist removing agent and a sort of resist removing composition, having an excellent capability for removing a resist and polymer and which does not attack underlying layers, a method for preparing the same and a resist removing method using the same. The resist removing agent includes alkoxy N-hydroxyalkyl alkanamide. The resist removing composition includes alkoxy N-hydroxyalkyl alkanamide, and at least a polar material having a dipole moment of 3 or greater, an attack inhibitor and alkanolamine. A substrate has the resist thereon is brought into contact with the resist removing agent or resist removing composition to remove the resist.
Description
Invention field
The present invention relates to a kind of resist and remove the method that agent, a kind of composition, its preparation method and employing said composition that removes resist remove resist.Particularly, the present invention relates to the method that alkoxyl N-hydroxy alkyl chain acid amides removes the purposes of agent, the composition that removes resist and its preparation method and adopts said composition to remove resist as resist.
Background of invention
The resist subtractive process is the main process of preparation semiconductor device.After the various processes that are used to prepare semiconductor device such as etching process (dry ecthing or wet etching) or ion implantation process are finished, must remove the resist pattern that uses as covert.In addition, when the resist floating, also must remove the resist pattern to form new resist pattern.Particularly, various different material layers such as oxide skin(coating), aluminium lamination, copper layer, silicone layer, silicide layer or polyimide layer can be present in below the resist layer of desiring to remove.Thereby for removing the resist process, the problem of overriding concern is exactly to remove resist as quickly as possible fully, simultaneously would not the chemical erosion bottom.
At present extensively the resist that adopts remove agent comprise such as the basic amine of hydramine, diglycolamine, monoethanolamine or methylethanolamine and such as the polar solvent of water or alcohol as solvent.
Because this conventional resist removes agent and can not remove polymkeric substance fully, thus also need to adopt remove polymkeric substance remove step in advance.Described polymkeric substance is a kind of when carrying out plasma etching or active-ion-etch (RIE) when adopting the resist pattern as covert with etching bottom, constitutes the material that the component of resist pattern such as carbon (C), hydrogen (H) or oxygen (O) and plasma reaction produce.Particularly, when metal level forms, can produce organometallic polymer under the resist pattern.If do not remove this polymkeric substance or organometallic polymer, but still in contact hole or in the via hole time, contact resistance will increase.Therefore, adopting before resist removes agent, must with cleaning reinforcing agent such as the salpeter solution that can remove polymkeric substance matrix handled removing in advance in the step process.
But conventional resist removes agent chemical erosion bottom.The representative instance of erodible bottom is a metal level.Its reason is that resist removes agent and mainly is made up of basic solvent that is easy to the corroding metal layer or water.Therefore, after carrying out, remove rinse step before, remove step after also must preventing to corrode.After remove in the step, for example adopt isopropyl alcohol (IPA).
Thereby owing to further adopted nitric acid treatment step (promptly removing step in advance) and isopropyl alcohol treatment step (removing step promptly), resist subtractive process to become quite complicated, prolong process time, thereby reduced productive capacity.In addition because except that resist removes material, also need to remove in advance material such as nitric acid and after remove material such as isopropyl alcohol, cause production cost to increase.In addition and since need various remove in advance step and after remove the container of step, unnecessarily increased the volume that resist removes equipment.
First purpose of the present invention provides a kind of resist and removes agent, and it has the excellent ability that removes resist and polymkeric substance, and can not corrode and be exposed to the bottom that resist removes agent.
Second purpose of the present invention provides a kind of composition that is used to remove resist, and it has the excellent ability that removes resist and polymkeric substance, and can not corrode and be exposed to the bottom that resist removes agent.
The 3rd purpose of the present invention provides a kind of method that resist removes agent for preparing.
The 4th purpose of the present invention provides a kind of resist that adopts and removes the method that composition removes resist.
Therefore, for realizing above-mentioned purpose of the present invention and other purpose and advantage, provide a kind of resist that comprises alkoxyl N-hydroxy alkyl alkanamides to remove agent.
On the other hand, resist removes composition to comprise alkoxyl N-hydroxy alkyl alkanamides and at least a dipole moment is 3 or greater than 3 polar material and a kind of erosion inhibitor.
On the other hand, resist removes composition and comprises alkoxyl N-hydroxy alkyl alkanamides and alkanolamine.It is 3 or greater than 3 polar material and a kind of erosion inhibitor that said composition also further comprises at least a dipole moment.
On the other hand, the method for preparing alkoxyl N-hydroxy alkyl alkanamides comprises makes alkanolamine mix with the alkoxyalkanoic acids Arrcostab, and makes the potpourri reaction of alkanolamine and alkoxyalkanoic acids Arrcostab.
In order to realize the 4th purpose, the method that removes resist is provided, this method comprises: a kind of matrix is provided, on matrix, form resist, making matrix and the resist that contains alkoxyl N-hydroxy alkyl alkanamides remove agent or remove composition with resist contacts to remove resist from matrix, described resist removes that composition comprises alkoxyl N-hydroxy alkyl alkanamides and alkanolamine and at least a dipole moment that is selected from is 3 or greater than 3 polar material, a kind of erosion inhibitor, and alkanolamine.
Resist of the present invention removes agent or resist and removes composition and have the excellent ability that removes resist, and can remove polymkeric substance and organometallic polymer effectively, and can not corrode and be exposed to the bottom that resist removes agent or composition.
The accompanying drawing summary
Fig. 1 is a process flow diagram, and wherein, solid line represents to adopt resist of the present invention to remove agent or resist removes the method that composition is removed resist and polymkeric substance, and dotted line represents because the conventional steps that the present invention saves;
Fig. 2 removes the block scheme that resist that agent or resist remove composition removes equipment for adopting resist of the present invention;
Fig. 3 removes the synoptic diagram that horizontal resist that agent or resist remove composition removes equipment for adopting resist of the present invention;
Fig. 4 removes the synoptic diagram that vertical resist that agent or resist remove composition removes equipment for adopting resist of the present invention;
Fig. 5 adopts resist of the present invention for explanation and removes the stereoscan photograph that composition removes resist pattern result;
Fig. 6 adopts conventional resist for explanation and removes the stereoscan photograph that composition removes resist pattern result;
Fig. 7 is the sectional view with matrix of copper layer, and it removes compositions-treated without resist;
Fig. 8 is the sectional view with matrix of copper layer, and it removes composition with resist of the present invention and handles;
Fig. 9 is the sectional view with matrix of copper layer, and it removes composition with conventional resist and handles;
Figure 10 for explanation before the matrix with copper layer removes compositions-treated with resist of the present invention, employing Auger electron microscope is to the synoptic diagram of the observations of the copper layer that forms on the matrix;
Figure 11 for explanation after the matrix with copper layer removes compositions-treated with resist of the present invention, employing Auger electron microscope is to the synoptic diagram of the observations of the copper layer that forms on the matrix; With
Figure 12 is the synoptic diagram of the component concentration variation of explanation resist composition, and adopting gas chromatography was interval measurement 48 hours with 8 hours.
The preferred embodiment explanation
Below, will describe that resist of the present invention removes agent and resist removes composition in detail, also will describe their preparation method in detail and adopt them to remove the method for resist, and the resist that is adopted in the resist removal methods removes equipment.Yet the present invention can multiple multi-form embodying, and the present invention should not be limited in the following embodiment.In addition it is of the present invention open more abundant and complete to provide these embodiments to make, and make those skilled in the art can realize the present invention fully.
Resist removes agent
Resist of the present invention removes agent and comprises alkoxyl N-hydroxy alkyl alkanamides.More particularly, alkoxyl N-hydroxy alkyl alkanamides is represented by formula (I):
R
4-O-R
3-CO-N-R
1R
2OH (I)
Wherein, R
1Be hydrogen atom, C
1-C
5Alkyl (non-ring alkyl that promptly has 1-5 carbon atom) or have 1-3 the ring aromatic hydrocarbyl; R
2Be C
1-C
5Alkyl or have 1-3 the ring aromatic hydrocarbyl; R
3And R
4Be C independently of one another
1-C
5In the alkyl any.
In preferred embodiments, R
1Be hydrogen atom, R
2For-CH
2CH
2-, R
3For-CH
2CH
2-, R
4For-CH
3
Resist of the present invention removes agent and comprises hydroxyl (OH), alkoxy (OR
4) and carbonyl (C=O).Thereby resist of the present invention removes agent can peel off and dissolve resist and polymkeric substance very effectively.
Equally, shown in following reaction equation (1), resist removes agent and organometallic polymer reaction, thereby, be easy to remove organometallic polymer from the surface of matrix:
(reaction equation 1)
Wherein, Mp represents organometallic polymer.
Resist removes composition
According to first embodiment of the present invention, resist removes composition, and to comprise alkoxyl N-hydroxy alkyl alkanamides, at least a dipole moment be 3 or greater than 3 polar material and a kind of erosion inhibitor.
The alkoxyl N-hydroxy alkyl alkanamides compound of formula (I) as previously mentioned of serving as reasons.
Dipole moment is 3 or demonstrates cross-linked polymer and the very high dissolubility of resist greater than 3 polar material.That is to say, can remove the polymkeric substance that is bonded on the resist pattern sidewalls strongly and exposes bottom surface effectively by this polar material.Simultaneously, by this polar material also can convenient resist self remove.Adoptable dipole moment is 3 or is water, methyl alcohol or dimethyl sulfoxide greater than 3 polar material.
Erosion inhibitor can make each layer (particularly metal level) that is exposed to resist and removes composition avoid corroding.Erosion inhibitor is represented by following formula (II):
R
6-(OH)
n (II)
Wherein, R
6Be C
1-C
5Alkyl has-C of COOH group
1-C
5Alkyl has the aromatic hydrocarbyl of 1-3 ring, or has 1-3 ring and have at least one encircles-alkyl of COOH group.Integer n can be 1-4, comprises endpoint value.
Particularly, preferred R
6Be phenyl ring, etchant is that n is 2 catechol.Equally, gallic acid also is a kind of erosion inhibitor that can be used for known formula of the present invention (II) expression.
When erosion inhibitor was catechol, the erosion of metal level suppressed mechanism and is illustrated by following reaction equation (2):
(reaction equation 2)
Wherein, M represents metal.
Remove composition according to the resist of second embodiment of the present invention and comprise alkoxyl N-hydroxy alkyl alkanamides and alkanolamine.
Alkanolamine is the compound of following formula (III) expression:
R
1-NH-R
2OH (III)
Wherein, R
1Be hydrogen, C
1-C
5Alkyl or have 1-3 the ring aromatic hydrocarbyl, R
2Be C
1-C
5Alkyl, or have 1-3 aromatic hydrocarbyl that encircles.In preferred embodiments, R
1Be hydrogen, R
2Be monoethanolamine, promptly-CH
2CH
2-.
Alkanolamine also can be removed organometallic polymer effectively.When adopting monoethanolamine, the organometallic polymer of alkanolamine removes mechanism and is represented by following reaction equation (3):
(reaction equation 3)
Wherein, Mp represents organometallic polymer.
The resist of second kind of embodiment of the present invention removes composition, and preferably also to comprise at least a dipole moment be 3 or greater than 3 polar material and a kind of erosion inhibitor.
Resist of the present invention removes the weight percentage of composition and various components by following table 1 expression.In the table 1, the content of preferred composition provides with parenthesis.
Table 1: resist removes composition
| Be used to remove the composition of resist | Alkoxyl N-hydroxy alkyl alkanamides (wt%) | Alkanolamine (wt%) | Polar material (wt%) | Erosion inhibitor (wt%) |
| 1 | 30-99.99 | 0.01-70 | ||
| 2 | 30-99.99 | 0.01-70 | ||
| 3 | 30-99.98 (40-60) | 0.01-40 (20-30) | 0.01-40 (20-30) | |
| 4 | 30-99.9 | 0.1-70 | ||
| 5 | 30-99.89 | 0.1-40 | 0.01-30 | |
| 6 | 30-99.89 | 0.1-40 | 0.01-30 | |
| 7 | 30-99.88 (40-65) | 0.1-40 (5-30) | 0.01-30 (5-20) | 0.01-30 (5-20) |
The content of above-mentioned composition is optimum content, and wherein, resist and polymkeric substance can be removed effectively, and this composition removes agent or resist and removes composition and be positioned at the erosion minimum of the layer of resist layer below as metal level being exposed to resist.
In above-mentioned composition, composition 3 and 7 has all comprised polar material and erosion inhibitor, and it is best that they remove the effect of resist and polymkeric substance.Equally, when having metal level below resist, the fast composition of institute can the attack metal layer.
In addition, when being removed material that composition corrodes such as metal level by resist and be not exposed to resist and remove composition, the composition 1,4 and 5 that does not comprise erosion inhibitor also has composition 3 effect identical with 7.Equally, suppress to become prior factor in erosion when metal material, the amount of removing of polymkeric substance is considerably less, or when having carried out removing step in advance, does not comprise dipole moment and be 3 or also have composition 3 effect identical with 7 greater than the composition 2,4 and 6 of 3 polar material.
As mentioned above, resist removes agent or resist and removes composition and have excellent performance aspect resist and the polymkeric substance (accessory substance of etching process) removing.Equally, they can not corrode the layer below the resist, for example metal level.In addition, to remove composition than conventional resist cheap for above-mentioned material.
Prepare the method that resist removes agent
The alkanolamine that alkoxyl N-hydroxy alkyl alkanamides of the present invention can be by making formula (III) and the alkoxyalkanoic acids Arrcostab of formula (IV) react according to following reaction equation (4) and prepare:
(reaction equation 4)
<III> <IV> <I> +<V>
Wherein, R
1Be hydrogen atom, C
1-C
5Alkyl or have 1-3 the ring aromatic hydrocarbyl; R
2Be C
1-C
5Alkyl or have 1-3 the ring aromatic hydrocarbyl; R
3And R
4Be C independently of one another
1-C
5In the alkyl any.
The preferred monoethanolamine of alkanolamine, wherein, R
1Be hydrogen atom, R
2For-CH
2CH
2-, the preferred methoxypropionic acid methyl esters of alkoxyalkanoic acids Arrcostab, wherein, R
3For-CH
2CH
2-, R
4For-CH
3, R
5For-CH
3
Here, for providing enough energy to this reaction, temperature of reaction should remain on room temperature to about 120 ℃.In the preferred embodiment of this method, with extremely about 80 ℃ to about 90 ℃ of mixture heated.
From above-mentioned reaction equation as can be seen, amine (III) produces acid amides (I) and alcohol (V) with ester (IV) reaction.
When alcohol (V) is lower boiling C
1-C
5Alcohol is during as the about 60 ℃ methyl alcohol of boiling point, and acid amides (I) is a high boiling substance, the methoxyl N-hydroxyethyl propionamide about 200 ℃ as boiling point.Thereby, adopt fractionating process can remove alcohol (V), obtain acid amides (I) compound.
Preferred fractional distillation process by carrying out, or makes alcohol (V) evaporation by the pressure that reduces reactor with the bubbling of nitrogen in reactor.Certainly, two kinds of methods also can adopt simultaneously.
The preparation resist removes method for compositions
Resist as shown in table 1 removes composition and prepares like this: at first, prepare alkoxyl N-hydroxy alkyl alkanamides of the present invention in the above described manner, then, make its hydramine with content shown in the table 1 and at least a erosion inhibitor that is selected from, has dipole moment and is 3 or mix greater than 3 the material and the material of alkanolamine.
Equally, the described composition 1 to 7 of table 1 can be according to following process preparation.
At first, the erosion inhibitor of 0.01-30wt% at least, the polar material of 0.01-30wt%, the alkanolamine of 10-70wt% (preferred 30-40wt%) are mixed with the alkoxyalkanoic acids Arrcostab of 10-70wt% (preferably 30-40wt%).The mixing ratio of preference chain alkanolamine and alkoxyalkanoic acids Arrcostab should make the total amount of alkoxyalkanoic acids Arrcostab can be fully and the alkanolamine reaction to be converted to acid amides.The temperature of potpourri remains on room temperature to about 120 ℃.Preferably with extremely about 80 ℃ to about 90 ℃ of mixture heated.Reaction time is 1-24 hour, preferred 1-12 hour.After heating is finished, reactant was placed separately 1-7 hour.
Whether reaction is finished can be determined by visual discriminating or by gas chromatography.Be that the layer that attachment reaction carries out observing in the component separates disappearance in visual discriminating.When the component layers complete obiteration that separates, can assert that reaction finishes.When adopting gas chromatographic analysis to form, the area percent of N-alkanol alkoxyalkyl alkanamides surpasses at 80% o'clock, means to react to finish.Area percent is defined as the area at peak relevant with a kind of component in the gas chromatography divided by the total area of all components under all peaks, and quotient multiply by 100 again.
Subsequently, in order to remove the low-flash alcohol that produces with accessory substance, must carry out fractionation operation.Preferred fractional distillation process by carrying out, or makes the alcohol evaporation by the pressure that reduces reactor with the bubbling of nitrogen in reactor.Two kinds of methods also can adopt simultaneously.Preferably carry out fractionation so that 7-8wt% (in total composition) or still less pure residual.
Remove the method for resist
Adopting resist of the present invention to remove agent and resist removes the step that composition removes resist and will be described with reference to the solid line step of figure 1.What also must illustrate is that conventional method is represented by Fig. 1 solid line and dotted line step.Various methods that prepare semiconductor device such as etching (dry ecthing or wet etching) method or ion injection method adopt to be finished as the resist pattern of covert.Then, on the matrix that forms the resist pattern, carry out cineration step (step 110), promptly dry stripping process.Cineration step can omit.Subsequently, making the listed resist of the matrix that forms the resist pattern and table 1 remove agent or resist removes composition and contacts to remove resist or polymkeric substance or to remove resist simultaneously and polymkeric substance (step 120).This step is finished like this: resist is removed agent or resist remove composition and be positioned in the container, then, matrix is immersed in the container.Perhaps, when matrix moves through thrower, resist is removed agent or resist remove composition and be injected on the matrix.
When adopting resist of the present invention to remove agent or resist to remove composition, resist removes step at about 70 ℃ or be lower than under 70 ℃ the temperature and carry out, and particularly, in room temperature to 70 ℃, carries out under preferred 45 ℃ to 70 ℃.Duration of contact, preferably about 10-was about 30 seconds.
Remove agent or resist by resist of the present invention and remove the resist that composition removes and can be the resist that is applicable to short wavelength illumination, as be used for ArF excimer laser (193nm) resist, be used for the resist of conventional i-line (365nm) or be used for the resist of KrF excimer laser (248nm).
After resist is removed fully, remove the resist of staying on the matrix by rinsing (step 140) and remove the resist that agent, resist remove composition and dissolving.Rinse step adopts rinsing solution such as deionized water to carry out.If necessary, rinse step can be carried out in two steps.At last, matrix is undertaken dry to remove the deionized water (step 150) that residues on the matrix by Rotary drying method or employing isopropyl alcohol seasoning.
Behind drying steps 150, matrix is transferred to the following process process.When using in the resist step afterwards, after finishing this step, by step shown in Figure 1 the resist that is adopted is removed again.This repeat element construction process of process and resist remove step and finish semiconductor device.
As shown in Figure 1, because resist of the present invention removes agent or resist removes the ability that removes resist or polymkeric substance that composition has excellence, thereby, unlike the prior art, need not to remove in advance step 100 (dotted line); Equally, because the layer below resist avoids corroding, also can economize and remove step 130 (dotted line) after omitting.Therefore, compare,, only need to adopt simple method can remove resist fully according to the present invention with conventional resist removal methods.Therefore, the productive capacity of semiconductor device can significantly improve.
Resist removes equipment
As previously mentioned, owing to simplified the resist removal methods, resist of the present invention removes equipment and also can make forr a short time or tightr.
Referring to Fig. 2, resist of the present invention removes equipment 200 and comprises a resist simply and remove unit 210, rinse unit 220 and drying unit 230.That is to say, need not to adopt conventional remove in advance the unit and after remove the unit.Therefore, compared with prior art, removing equipment 200 occupied areas by resist can significantly reduce.When resist removed equipment 200 and adopts infusion processes, unit 210,220 and 230 was respectively corresponding to a container independently.Therefore, unlike the prior art, remove container handling after need not to adopt nitric acid to remove container handling and isopropyl alcohol (IPA) in advance, thereby saved two containers, remove the occupied area of equipment 200 thereby reduced resist significantly.
The resist of employing spray process removes equipment and can be divided into horizontal and vertical two kinds.
Referring to Fig. 3, horizontal resist removes equipment 300 and adopts horizontal load device 340, and as transmission system, operating parts (handler) or motion arm, this equipment is divided into resist and removes unit 310, rinse unit 320 and drying unit 330.Source apparatus 360 contains that resist of the present invention removes agent or resist removes composition, and it removes to resist through feeding unit 370, and unit 310 supply resists remove agent or resist removes composition.Rinsing liquid unit source apparatus 362 also is connected with rinse unit and drying unit 330 by feeding unit 370 respectively with drying agent unit source apparatus 364.Nozzle 312,322 and 332 is installed in the unit of the blasting materials that is applicable to each Elementary Function.In when operation, when matrix enters resist and removes in the unit 310, spray by nozzle 312 that resists remove agent or resist removes composition to remove resist.Here, matrix is passed through load device 340 continuously towards rinse unit 320 horizontal transport.At last, matrix is transferred to drying unit 330, carries out drying by drying agent then, as uses air drying, or by nozzle 322 jet drying chemical substance on matrix.Because horizontal resist removes equipment and only comprises three unit, the size of equipment greatly reduces.
Referring to Fig. 4, vertical resist removes equipment and adopts vertical movable matrix support member 440.Vertical equipment also comprises supply resist of the present invention and removes agent or resist and remove the source apparatus 460 of composition and supply resist and remove the feeding unit 470 that agent or resist remove composition.In preferred embodiments, matrix support member 440 is rotatable.Equally, the inside of equipment is configured to three sections zones with bed structure, vertically is provided with each other, and is not independent each other.That is to say that with vertical order, the unit removes zone 410 by arid region 430, rinsing zone 420 and resist and forms.Rinsing solution source apparatus 462 is connected through feeding unit 470 with feeder sleeve 450 with drying agent source apparatus 464.In this embodiment, single supply pipe 450 provides the material of all three unit in order.
When the matrix (not shown) after forming resist thereon enters in the matrix support member 440, support member 440 at first moves to the zone that removes resist, through feeding unit 470, remove agent or resist from the resist of feeding mechanism 460 and remove composition and spray by supply pipe 450.In preferred embodiments, after resist removed step and finishes, resist removed agent or resist and removes composition and discharge through the delivery pipe (not shown), and matrix support member 440 is moved downward to rinse unit 420 places with matrix.Rinsing solution is spurted in the rinse unit 420 through supply pipe 450.At last, matrix is sent to by 440 lengthwise movements of matrix support member and carries out drying in the drying unit 430.Though Fig. 4 has only shown that drying unit 430, rinse unit 420 and resist remove unit 410 and be provided with according to the order of sequence to the top bottom in the vertical, these unit can be according to opposite direction setting.Because vertical resist of the present invention removes equipment and also only comprises three unit, to compare with the vertical equipment of prior art, the size of equipment also is being reduction.
The present invention further describes in detail and will provide referring to following embodiment, still, is appreciated that the present invention is not limited to these embodiment.
Preparation methoxyl N-hydroxyethyl propionamide
To mix as the 200ml monoethanolamine of alkanolamine with as the 200ml methoxypropionic acid methyl esters of ester.Subsequently, potpourri was heated 5 hours down at 90 ℃.After the heating, reactant was at room temperature placed 5 hours.
The material that forms is analyzed with gas chromatography, to confirm to obtain methoxyl N-hydroxyethyl propionamide.In addition, product carry out proton magnetic resonance (PMR) (
1H-NMR) spectral analysis provides the relative populations (ppm) of each component.The NMR data of product are as follows: 6.8ppm (1H), 3.7-3.8ppm (4H), 3.4-3.5ppm (3H), 2.8-2.9ppm (1H).
Preparation methoxyl N-butyl hydroxyethyl propionamide
Will be as the 200mlN of alkanolamine, N-tert-butyl group monoethanolamine and mix as the 200ml methoxypropionic acid methyl esters of ester.Subsequently, potpourri was heated 5 hours down at 90 ℃.After the heating, reactant was at room temperature placed 5 hours.
The product that obtains is analyzed with gas chromatography, confirmed to obtain methoxyl N-butyl hydroxyethyl propionamide.
Suitable temperature evaluation in preparation methoxyl N-hydroxyethyl propionamide process
To mix as the 200ml monoethanolamine (MEA) of alkanolamine with as the 200ml methoxypropionic acid methyl esters of ester.Subsequently, determine to be applicable to the temperature of amine and ester reaction, synthesizing methoxy N-hydroxyethyl propionamide under different temperatures shown in the table 2 is measured and is finished the synthetic time that consumes.Adopt gas chromatographic analysis, surpass the 80% synthetic selection of time of finishing of time affirmation that is consumed with area % by acid amides (methoxyl N-hydroxyethyl propionamide).
Table 2: the temperature and time of methoxyl N-hydroxyethyl propionamide reaction
| Temperature of reaction (℃) | 25 | 35 | 45 | 55 | 65 | 80 | 90 |
| Reaction time (hour) | 55 | 24 | 30 | 7 | 6 | 4 | 3 |
Find out that from The above results reaction can at room temperature be carried out, it is faster that speed is at high temperature carried out in reaction.But, consider processing conditions, preferable reaction temperature is no more than 120 ℃.Therefore, the temperature of preparation amide compound of the present invention is preferably room temperature to about 120 ℃.In the preferred embodiment of this method, temperature of reaction is about 80 ℃ to about 90 ℃.
EXAMPLE IV
The preparation resist removes composition and estimates the effect that it removes resist
As shown in table 3, adopt MEA, MMP, catechol and seven kinds of resists of water preparation of different content to remove composition.Subsequently, composition was heated 5 hours down at 80 ℃.Again the product that forms was at room temperature placed 6 hours.Then, remove methyl alcohol, nitrogen bubble is passed through, and adopt the decompression method simultaneously, to finish preparation of compositions by fractionation.
Adopting above-mentioned resist to remove the resist that composition removes prepares on 7 matrix in the following manner.Forming thickness at first, respectively on 7 matrix is BoroPhosphoSilicate glass (BPSG) layer of 5000 .Then, form titanium layer and nitric acid titanium layer that thickness is 200 more respectively, heating.Next, deposition aluminium lamination to thickness is 6000 , flows then.Nitric acid titanium layer as the end seal is formed on the aluminium lamination, forms the interlayer dielectric that thickness is 10000 then.After this, on interlayer dielectric, apply resist, carry out photoetch again to form the resist pattern that limits via hole.With resist pattern baking, the row etching during to middle dielectric layer with the oxide etching agent of buffering then adopts the resist pattern as covert, forms the via hole that is exposed to aluminium lamination.
After forming via hole, 7 kinds of matrix are carried out ashing, and be immersed in 7 containers that comprise the listed 7 kinds of compositions of table 3.The temperature of container is remained on 60 ℃.In submergence after 20 minutes, with substrate with water rinsing 5 minutes, drying.Adopt scanning electron microscope (SEM) to detect matrix then.According to the SEM observed result, matrix is assessed as good, good, best several grades, adopt the listed symbolic representation grade of table 3.The state of matrix is a characteristic present by the relative populations of the resist of the polymkeric substance of remnants and polymkeric substance.
Table 3: the resist of several compositions removes performance
| MEA(ml) | MMP(ml) | Catechol (g) | Water (ml) | |
|
| 1 | 50 | 350 | 60 | 100 | ○ |
| 2 | 100 | 300 | 60 | 100 | ○ |
| 3 | 150 | 250 | 60 | 100 | ⊙ |
| 4 | 200 | 200 | 60 | 100 | ⊙ |
| 5 | 250 | 150 | 60 | 100 | ◎ |
| 6 | 300 | 100 | 60 | 100 | ○ |
| 7 | 350 | 50 | 60 | 100 | ○ |
(zero: good; ◎: good; ⊙: the best)
" very " is similar with the result that the conventional resist of employing removes composition EKC-245, and " good " compared performance with conventional situation and improve, and " the best " then compared performance with conventional situation and significantly improved.EKC-245 is that conventional resist removes composition, and it comprises hydramine, diglycolamine, catechol and water as solvent.
EXAMPLE V
Composition component is analyzed
According to the ratio shown in the table 3 each component is mixed, then at the fixed time after, analyze the component concentration of each composition.Analysis result shows that each composition comprises each component that table 4 is listed.
Table 4: component is formed
| Methoxyl N-hydroxyethyl propylamine (wt%) | Monoethanolamine (wt%) | Catechol (wt%) | Water (wt%) | |
| 1 | 71.9 | 0.1 | 13 | 15 |
| 2 | 67 | 5 | 13 | 15 |
| 3 | 62 | 10 | 13 | 15 |
| 4 | 55 | 17 | 13 | 15 |
| 5 | 47 | 25 | 13 | 15 |
| 6 | 42 | 30 | 13 | 15 |
| 7 | 32 | 40 | 13 | 15 |
Example VI
The evaluation of suitable process time
In order to check suitable process time, adopt No. 4 compositions shown in the table 4, removing resist under different process times shown in the table 5.Other processing conditions is identical with EXAMPLE IV.The result that is etched of the removal effect of resist and aluminium lamination and silicon layer observes with SEM.
Table 5: the performance that removes that changes resist in time
| Process time (minute) | Resist removes ability and observes | Corrode or do not corrode (Al, Si) | |
| 1 | 10 | ◎ | × |
| 2 | 15 | ⊙ | × |
| 3 | 20 | ⊙ | × |
| 4 | 25 | ⊙ | × |
| 5 | 30 | ⊙ | × |
(◎: good; ⊙: the best)
In the table 5 corresponding to removal effect meet with table 3 in identical." * " shows that bottom is not etched in the table 5.
Find out that from the result of table 5 reaction time that optimum removes resist is 10 to 30 minutes, bottom can not be etched fully.
Example VII A
The evaluation of suitable processing temperature
For the processing temperature of confirming to suit, adopt No. 4 compositions shown in the table 4.Removing resist under the different processing temperatures shown in the table 6.Other processing conditions is identical with EXAMPLE IV.The result that is etched of the removal effect of resist and aluminium lamination and silicon layer adopts SEM to observe.
Table 6: the performance that removes that varies with temperature resist
| Processing temperature (℃) | Resist removes ability and observes | Corrode or do not corrode (Al, Si) | |
| 1 | 45 | ⊙ | × |
| 2 | 50 | ⊙ | × |
| 3 | 55 | ⊙ | × |
| 4 | 60 | ⊙ | × |
| 5 | 65 | ⊙ | × |
| 6 | 70 | ⊙ | × |
In the table 6 meet with table 5 in identical.Find out from the result of table 6, to about 70 ℃ lower temperature, can remove resist rapidly at about 45 ℃.
Example VII A I
Resist removes performance relatively
In the mode identical with EXAMPLE IV, adopt the resist pattern to form access opening, resist removes with No. 4 compositions shown in the table 4, and the processing time is 20 minutes, and temperature of reaction is 60 ℃.The product that obtains is observed with SEM, and observations as shown in Figure 5.
In comparing embodiment, resist adopts conventional resist to remove composition EKC-245 and removes, and other condition is same with the above-mentioned embodiment, and the product that obtains is observed with SEM, and observations as shown in Figure 6.
The result that Fig. 5 and SEM photo shown in Figure 6 are compared adopts resist of the present invention to remove composition and can remove resist fully as can be seen, and conventional resist then can stay the part resist when removing composition (as EKC-245).Equally, the bottom aluminium lamination can not be etched among the present invention, and when adopting EKC-245, then aluminium lamination can be etched.
Example I X
Measurement to the erosion action of copper layer
As shown in Figure 7, in order to determine that the copper layer (is interconnected layer as following one deck generation, should more note it) erosion action, at first, forming thickness on a plurality of matrix 1100 respectively is the bpsg layer 1200 of 5000 , then, adopt photo-engraving process on the bpsg layer of every kind of matrix, to form pattern to obtain a plurality of contact holes.Subsequently, order forms the titanium/ titanium nitride layer 1300 and 1350 as barrier metal layer on the surface of contact hole, and its thickness is respectively 200 , then, forms the copper layer 1400 of filling each contact hole, and its thickness is 10000 .
After this, a plurality of matrix are divided into three groups of A, B and C.A group need not remove compositions-treated by any resist, the B group is immersed in shown in 65 ℃ of following tables 4 No. 4 resists removes in the composition 100 minutes, with the C group be immersed in 65 ℃ down conventional resists remove in the composition (EKC-245) 100 minutes.
Adopt SEM to connect several matrix of observing each group.Fig. 7 has shown that working as matrix does not remove the situation (A group) that composition is handled with resist, and Fig. 8 has shown that working as matrix removes the situation (B group) that composition is handled with resist of the present invention.When adopting resist of the present invention to remove composition to handle, can reach the identical result of situation who does not remove compositions-treated, this ideal results with resist of the present invention.In other words, can confirm that resist of the present invention removes composition can not corrode the copper layer.But as shown in Figure 9, when adopting conventional resist to remove composition to handle (C group), it is very serious that the copper layer is etched, and almost completely removed the copper layer.From the result of Fig. 7 to 9, can calculate the etching speed of copper layer.The etching speed that calculates is listed in table 7.
Table 7: the etching speed of copper layer
| Group | A | B | C |
| Etching speed (/minute) | 0 | 0 | ＞1000 |
In order to determine that resist of the present invention removes the effect of composition to the copper laminar surface, the copper laminar surface of A group (not removing compositions-treated with resist crosses) and B group (removing compositions-treated with resist of the present invention crosses) copper laminar surface are analyzed with the Auger electronic spectrum, and analysis result is shown in respectively in Figure 10 and 11.Shown in Figure 10 and 11, because the Auger electronic spectrum shown in Figure 10 and 11 is basic identical, therefore, resist of the present invention removes composition can not have any effect to the copper layer.
Embodiment X
Resist removes the analysis of each component of composition
Each components contents that his-and-hers watches 4 described No. 4 resists remove composition served as to analyze at interval with vapor-phase chromatography with 8 hours.Analysis result is shown in Figure 12, wherein ,-■-the be meant area % of acid amides ,-△-the be meant area % of monoethanolamine ,-*-be meant the area % of methoxypropionic acid methyl esters.From result shown in Figure 12 as can be seen, even after 48 hours, the area % of acid amides is also constant in about 80%.Equally, the area % of monoethanolamine is constant in 3.4.And the area % of methoxypropionic acid methyl esters is after 24 hours, reduces to 0.5 from 0.9, until became 0 basically after 40 hours.Be appreciated that equally composition of the present invention has carried out reaction completely, become stable, comprise acid amides, amine, catechol and water.The main active component of considering composition of the present invention is an acid amides, even the content of acid amides is also almost constant after 48 hours, this hints out that composition of the present invention can not consume fast in process, can use the long time.This shows, removes composition EKC-245 (it must be changed every 24 hours) with the resist of routine employing and compares, and composition of the present invention can increase productive capacity, and can significantly reduce production costs.
Amide compound of the present invention has the ability that removes resist.Therefore, the resist of the present invention with amide compound removes agent or resist and removes composition and can remove polymkeric substance and organometallic polymer effectively.Equally, the layer below resist can not suffer erosion.Thereby, when adopting resist to remove agent or resist to remove composition, need not to remove again polymkeric substance remove step in advance and prevent that bottom from weathering after remove step.Because of drawing, the resist removal methods is simplified, and can shorten process time.In addition, removing the required temperature of resist can be arranged under the lower temperature.And then resist removes equipment and can simplify and make more compactly.
Those skilled in the art are appreciated that under the prerequisite that does not deviate from the spirit or scope of the present invention can carry out various improvement and variation to the present invention.Therefore, the present invention comprises these improvement and variation.
Claims (28)
1, a kind of resist removes agent, and it comprises the alkoxyl N-hydroxy alkyl chain acid amides by formula (I) expression:
R
4-O-R
3-CO-N-R
1R
2OH (I)
Wherein
R
1Be hydrogen atom, C
1-C
5Alkyl or have 1-3 the ring aromatic hydrocarbyl;
R
2Be C
1-C
5Alkyl or have 1-3 the ring aromatic hydrocarbyl;
R
3And R
4Be C independently of one another
1-C
5Alkyl.
2, the resist according to claim 1 removes agent, wherein, and R
1Be hydrogen, R
2For-CH
2CH
2-, R
3For-CH
2CH
2-, R
4For-CH
3
3, a kind of resist removes composition, and it comprises:
Alkoxyl N-hydroxy alkyl alkanamides by formula (I) expression:
R
4-O-R
3-CO-N-R
1R
2OH (I)
Wherein
R
1Be hydrogen atom, C
1-C
5Alkyl or have 1-3 the ring aromatic hydrocarbyl;
R
2Be C
1-C
5Alkyl or have 1-3 the ring aromatic hydrocarbyl;
R
3And R
4Be C independently of one another
1-C
5Alkyl; With
At least a dipole moment is 3 or greater than 3 polar material and a kind of erosion inhibitor,
Wherein, polar material is selected from water, methyl alcohol and dimethyl sulfoxide,
Wherein, erosion inhibitor is represented by following formula (II):
R
6-(OH)
n (II)
Wherein, R
6Be C
1-C
5Alkyl has-C of COOH group
1-C
5Alkyl has the aromatic hydrocarbyl of 1-3 ring, or has 1-3 ring and have at least one encircles-alkyl of COOH group.N is integer 1-4.
4, the resist according to claim 3 removes composition, wherein, removes composition weight meter with resist, and the content of alkoxyl N-hydroxy alkyl alkanamides is 30 to 99.9wt%.
5, the resist according to claim 3 removes composition, wherein, removes composition weight meter with resist, and the content of polar material and erosion inhibitor is respectively 0.01 to 30wt%.
6, a kind of resist removes composition, and it comprises:
Alkoxyl N-hydroxy alkyl alkanamides by formula (I) expression;
R
4-O-R
3-CO-N-R
1R
2OH (I)
Wherein
R
1Be hydrogen atom, C
1-C
5Alkyl or have 1-3 the ring aromatic hydrocarbyl;
R
2Be C
1-C
5Alkyl or have 1-3 the ring aromatic hydrocarbyl;
R
3And R
4Be C independently of one another
1-C
5Alkyl; With
Alkanolamine.
7, the resist according to claim 6 removes composition, also comprises at least a dipole moment and be 3 or greater than 3 polar material and a kind of erosion inhibitor, wherein, polar material is selected from water, methyl alcohol and dimethyl sulfoxide,
Wherein, erosion inhibitor is represented by following formula (II):
R
6-(OH)
n (II)
Wherein, R
6Be C
1-C
5Alkyl has-C of COOH group
1-C
5Alkyl has the aromatic hydrocarbyl of 1-3 ring, or has 1-3 ring and have at least one encircles-alkyl of COOH group, and n is integer 1-4.
8, the resist according to claim 7 removes composition, and wherein, alkanolamine is represented by following formula (III):
R
1-NH-R
2OH (III)
Wherein, R
1Be hydrogen, C
1-C
5Alkyl or have 1-3 the ring aromatic hydrocarbyl, R
2Be C
1-C
5Alkyl, or have 1-3 aromatic hydrocarbyl that encircles.
9, the resist according to claim 6 removes composition, wherein, removes composition weight meter with resist, and the content of alkoxyl N-hydroxy alkyl alkanamides is 30 to 99.9wt%.
10, the resist according to claim 6 removes composition, wherein, removes composition weight meter with resist, and the content of alkanolamine is respectively 0.1 to 70wt%.
11, the resist according to claim 7 removes composition, wherein, removes composition weight meter with resist, and the content of polar material and erosion inhibitor is respectively 0.01 to 30wt%.
12, the resist according to claim 7 removes composition, wherein, remove composition weight meter with resist, the content of alkoxyl N-hydroxy alkyl alkanamides, alkanolamine, polar material and erosion inhibitor is respectively 40 to 65wt%, 5 to 30wt%, 5 to 20wt% and 5 to 20wt%.
13, a kind of method for preparing alkoxyl N-hydroxy alkyl alkanamides, this method comprises:
Alkanolamine is mixed with the alkoxyalkanoic acids Arrcostab; With
Make the reaction of alkanolamine and alkoxyalkanoic acids Arrcostab form the alkoxyl N-hydroxy alkyl alkanamides of representing by formula (I)
R
4-O-R
3-CO-N-R
1R
2OH (I)
Wherein
R
1Be hydrogen atom, C
1-C
5Alkyl or have 1-3 the ring aromatic hydrocarbyl;
R
2Be C
1-C
5Alkyl or have 1-3 the ring aromatic hydrocarbyl;
R
3And R
4Be C independently of one another
1-C
5Alkyl.
14, according to the method for claim 13, wherein, in described mixed process, alkanolamine has formula (III):
R
1-NH-R
2OH (III)
Wherein, R
1Be hydrogen, C
1-C
5Alkyl or have 1-3 the ring aromatic hydrocarbyl, R
2Be C
1-C
5Alkyl, or have 1-3 aromatic hydrocarbyl that encircles;
The alkoxyalkanoic acids Arrcostab has following formula (IV):
R
4-O-R
3-COO-R
5 (IV)
Wherein, R
3, R
4And R
5Be C independently of one another
1-C
5Alkyl.
15, according to the method for claim 14, wherein, in described mixed process, remove composition in resist, the content of alkanolamine is 10 to 70wt%, and the content of alkoxyalkanoic acids Arrcostab is 10 to 70wt%.
16, according to the method for claim 13, wherein, in described mixed process, further mix at least a dipole moment and be 3 or greater than 3 polar material and a kind of erosion inhibitor, wherein, polar material is selected from water, methyl alcohol and dimethyl sulfoxide,
Wherein, erosion inhibitor is represented by following formula (II):
R
6-(OH)
n (II)
Wherein, R
6Be C
1-C
5Alkyl has-C of COOH group
1-C
5Alkyl has the aromatic hydrocarbyl of 1-3 ring, or has 1-3 ring and have at least one encircles-alkyl of COOH group, and n is integer 1-4.
17, according to the method for claim 16, wherein, in described mixed process, remove composition in resist, the content of polar material and erosion inhibitor is respectively 0.01 to 30wt%,
18, according to the method for claim 13, wherein, described being reflected under the room temperature to 120 ℃ carried out.
19, according to the method for claim 18, after described reaction, further comprise the process of recovery as the alcohol of byproduct of reaction generation.
20, a kind of resist removal methods comprises:
A kind of matrix is provided;
On matrix, form resist; With
Making matrix and a kind of resist that contains alkoxyl N-hydroxy alkyl alkanamides remove agent or resist removes composition and contacts, to remove resist from matrix, described resist removes composition, and to comprise alkoxyl N-hydroxy alkyl alkanamides and at least a dipole moment be 3 or greater than 3 polar material, a kind of erosion inhibitor and alkanolamine
Wherein, in described contact process, alkoxyl N-hydroxy alkyl alkanamides is represented by formula (I):
R
4-O-R
3-CO-N-R
1R
2OH (I)
Wherein
R
1Be hydrogen atom, C
1-C
5Alkyl or have 1-3 the ring aromatic hydrocarbyl;
R
2Be C
1-C
5Alkyl or have 1-3 the ring aromatic hydrocarbyl;
R
3And R
4Be C independently of one another
1-C
5Alkyl;
Wherein, in described contact process, polar material is selected from water, methyl alcohol and dimethyl sulfoxide;
Wherein, in described contact process, erosion inhibitor is the compound by following formula (II) expression:
R
6-(OH)
n (II)
Wherein, R
6Be C
1-C
5Alkyl has-C of COOH group
1-C
5Alkyl has the aromatic hydrocarbyl of 1-3 ring, or has 1-3 ring and have at least one encircles-alkyl of COOH group, and n is integer 1-4.
21, according to the method for claim 20, wherein, in described contact process, alkanolamine has formula (III):
R
1-NH-R
2OH (III)
Wherein
R
1Be hydrogen, C
1-C
5Alkyl or have 1-3 the ring aromatic hydrocarbyl; With
R
2Be C
1-C
5Alkyl, or have 1-3 aromatic hydrocarbyl that encircles.
22, according to the method for claim 20, wherein, in described contact process, wherein, remove composition weight meter with resist, the content of alkoxyl N-hydroxy alkyl alkanamides is 30 to 99.9wt%.
23, according to the method for claim 20, wherein, in described mixed process, remove composition in resist, the content of polar material and erosion inhibitor is respectively 0.01 to 30wt%.
24, according to the method for claim 20, wherein, in described contact process, remove composition in resist, the content of alkanolamine is 10 to 70wt%.
25, according to the method for claim 20, wherein, remove composition weight meter with resist, the content of alkoxyl N-hydroxy alkyl alkanamides, alkanolamine, polar material and erosion inhibitor is respectively 40 to 65wt%, 5 to 30wt%, 5 to 20wt% and 5 to 20wt%.
26, according to the method for claim 20, after described contact, further comprise:
Rinsing matrix; With
Dry matrices.
27, according to the method for claim 26, before described contact, further comprise the step of ashing matrix.
28, according to the method for claim 20, wherein, described contact process is carried out under 45 ℃ to 70 ℃.
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR32354/1998 | 1998-08-05 | ||
| KR32355/1998 | 1998-08-05 | ||
| KR19980032355 | 1998-08-05 | ||
| KR19980032354 | 1998-08-05 | ||
| KR20973/1999 | 1999-06-07 | ||
| KR1019990020973A KR100335484B1 (en) | 1998-08-05 | 1999-06-07 | Use of an Alkoxy N-Hydroxyalkyl Alkanamide as Resist Removing Agent, Composition for Removing Resist, Method for Preparing the Same and Resist Removing Method Using the Same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1243971A CN1243971A (en) | 2000-02-09 |
| CN1249530C true CN1249530C (en) | 2006-04-05 |
Family
ID=27349792
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB991119657A Expired - Fee Related CN1249530C (en) | 1998-08-05 | 1999-08-05 | Alkoxyl N-hydroxy alkyl acylamine used as corrosion inhibitor remover |
Country Status (4)
| Country | Link |
|---|---|
| KR (1) | KR100335484B1 (en) |
| CN (1) | CN1249530C (en) |
| FR (1) | FR2782176B1 (en) |
| GB (1) | GB2340256B (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6274537B1 (en) * | 1998-08-05 | 2001-08-14 | Samsung Electronics Co., Ltd. | Use of alkoxy N-hydroxyalkyl alkanamide as resist removing agent, composition for removing resist, method for preparing the same and resist removing method using the same |
| KR100335484B1 (en) * | 1998-08-05 | 2002-05-04 | 윤종용 | Use of an Alkoxy N-Hydroxyalkyl Alkanamide as Resist Removing Agent, Composition for Removing Resist, Method for Preparing the Same and Resist Removing Method Using the Same |
| KR100360397B1 (en) * | 1999-11-26 | 2002-11-18 | 삼성전자 주식회사 | Resist removing composition and resist removing method using the same |
| JP4810764B2 (en) * | 2001-06-29 | 2011-11-09 | 三菱瓦斯化学株式会社 | Resist stripper composition |
| KR100468714B1 (en) * | 2001-07-03 | 2005-01-29 | 삼성전자주식회사 | Resist removing composition and resist removing method using the same |
| KR100434491B1 (en) | 2001-08-17 | 2004-06-05 | 삼성전자주식회사 | Resist or etching by-products removing composition and resist removing method using the same |
| KR101017738B1 (en) * | 2002-03-12 | 2011-02-28 | 미츠비시 가스 가가쿠 가부시키가이샤 | Photoresist stripping composition and cleaning composition |
| US7037852B2 (en) | 2002-09-26 | 2006-05-02 | Samsung Electronics Co., Ltd. | Composition for stripping photoresist and method of preparing the same |
| JP4085262B2 (en) * | 2003-01-09 | 2008-05-14 | 三菱瓦斯化学株式会社 | Resist stripper |
| KR100751919B1 (en) | 2005-11-18 | 2007-08-31 | 램테크놀러지 주식회사 | Photoresist stripping composition and method of forming a pattern using the same |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2820801A (en) * | 1958-01-21 | Chjchj | ||
| US2704280A (en) * | 1951-05-29 | 1955-03-15 | Colgate Palmolive Co | Long-chain aliphatic ether-amides in detergent compositions |
| GB2199587B (en) * | 1986-12-10 | 1991-03-27 | Advanced Chem Tech | Stripping compositions and use therof |
| US5204026A (en) * | 1988-05-20 | 1993-04-20 | The Boeing Company | Solvent with alicyclic carbonate and ethylene dipropionate |
| US5690747A (en) * | 1988-05-20 | 1997-11-25 | The Boeing Company | Method for removing photoresist with solvent and ultrasonic agitation |
| JP2759462B2 (en) * | 1988-11-11 | 1998-05-28 | ナガセ電子化学株式会社 | Aqueous release agent composition |
| JPH02253265A (en) * | 1989-03-28 | 1990-10-12 | Nippon Zeon Co Ltd | Resist peeling agent |
| US5556482A (en) * | 1991-01-25 | 1996-09-17 | Ashland, Inc. | Method of stripping photoresist with composition containing inhibitor |
| US5753601A (en) * | 1991-01-25 | 1998-05-19 | Ashland Inc | Organic stripping composition |
| JPH08190205A (en) * | 1995-01-10 | 1996-07-23 | Mitsubishi Gas Chem Co Inc | Photoresist removing agent composition and removing method |
| JPH08202051A (en) * | 1995-01-26 | 1996-08-09 | Mitsubishi Gas Chem Co Inc | Peeling agent composition for photoresist and peeling method |
| KR100234532B1 (en) * | 1996-09-21 | 1999-12-15 | 윤종용 | Thinner composition used in cleaning photoresist and semiconductor manufacturing method using the same |
| JPH11125917A (en) * | 1997-10-21 | 1999-05-11 | Fuji Film Olin Kk | Photoresist stripping solution |
| KR100335484B1 (en) * | 1998-08-05 | 2002-05-04 | 윤종용 | Use of an Alkoxy N-Hydroxyalkyl Alkanamide as Resist Removing Agent, Composition for Removing Resist, Method for Preparing the Same and Resist Removing Method Using the Same |
-
1999
- 1999-06-07 KR KR1019990020973A patent/KR100335484B1/en not_active IP Right Cessation
- 1999-08-04 FR FR9910120A patent/FR2782176B1/en not_active Expired - Fee Related
- 1999-08-04 GB GB9918418A patent/GB2340256B/en not_active Expired - Fee Related
- 1999-08-05 CN CNB991119657A patent/CN1249530C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| KR100335484B1 (en) | 2002-05-04 |
| KR20000016878A (en) | 2000-03-25 |
| GB9918418D0 (en) | 1999-10-06 |
| GB2340256A (en) | 2000-02-16 |
| CN1243971A (en) | 2000-02-09 |
| FR2782176A1 (en) | 2000-02-11 |
| GB2340256B (en) | 2002-06-19 |
| FR2782176B1 (en) | 2005-09-23 |
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