CN1244029A - Method and apparatus for removing corrosion inhibitor - Google Patents
Method and apparatus for removing corrosion inhibitor Download PDFInfo
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- CN1244029A CN1244029A CN 98123847 CN98123847A CN1244029A CN 1244029 A CN1244029 A CN 1244029A CN 98123847 CN98123847 CN 98123847 CN 98123847 A CN98123847 A CN 98123847A CN 1244029 A CN1244029 A CN 1244029A
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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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Abstract
The present invention relates to a resist removing method and a resist removing apparatus using the method. The resist removing method comprises the steps of providing a basis material and forming resist thereon; and then the basis material is brought into contact with the resist removing agent containing alkoxy N-hydroxyalkyl alkanamide to remove the resist from the basis material. Alternately, the basis material is brought into contact with the resist removing composition containing alkoxy N-hydroxyalkyl alkanamide, etching inhibitor or alkanolamine and alkyl oxyalkyl alkanoic acid ester. The productivity of the semiconductor element manufacture apparatus can be increased by using simple method to removing resist at short time and by reducing the size of the resist removing apparatus.
Description
The present invention relates to a kind of method of resist, a kind of semiconductor element that removes the equipment of resist and prepare in this way of removing.More particularly, the present invention relates to a kind of like this method and apparatus that removes resist, it is delivered to the novel material that removes resist on the resist of base material.
Removing the resist process is important process during semiconductor element is made.For example, making the various processes of semiconductor element, for example after etching process (dry etching or wet etching) or the ion implantation process, must remove on semiconductor substrate resist figure as shelter.In addition, if this resist map migration, it must remove from new resist figure.Below resist layer, can there be various material layers to exist, for example oxide skin(coating), aluminium lamination, polysilicon layer, silicide layer or polyimide layer.So, be as far as possible promptly to remove resist layer and don't etch bottom fully to an important consideration of resist subtractive process.
At present widely used a kind of resist removes agent and contains basic amine (for example azanol, diglycolamine, monoethanolamine or methylethanolamine) and polar solvent (for example water and alcohol) as its key component.
Because removing agent, so traditional resist can not remove polymer fully, so also need a step that removes polymer in advance.Such polymer is when carrying out plasma etching or reactive ion etching (RIE) with the resist figure as shelter, by the component that the constitutes resist material that generates of carbon (C), hydrogen (H) or oxygen (O) and plasma reaction for example.Specifically, when the resist figure forms metal level down, just generate organometallic polymer.If such polymer or organometallic polymer do not remove, so still contact with hole or passage, for example can make the contact resistance increase and in semiconductor element, produce defective.Therefore, before the use resist removes agent, must remove in advance in the step, remove for example nitric acid (HNO of agent with polymer
3) the solution-treated base material.
Traditional resist removes agent may the etch bottom.Be metal level easily by exemplary in the bottom of etch.Above-mentioned reason is because 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 before the cleaning step, must remove step after etch from carrying out for preventing.After this, remove in the step, for example use isopropyl alcohol (IPA).
Because also will carry out nitric acid treatment step (removing step in advance) and IPA treatment step (afterwards removing step) usually, so the resist subtractive process becomes more complicated, and prolong process time, thereby productivity ratio is descended.In addition because also need to use remove in advance material for example nitric acid and after remove material for example IPA and resist remove material, so manufacturing expense increases.In addition, because need be used for the various material troughs of splendid attire nitric acid and IPA, become very big thereby make resist remove equipment.
An object of the present invention is to provide a kind of solves basically because the resist removal methods of one or more problems that the restriction of correlation technique and shortcoming produce.
Second purpose of the present invention is to provide a kind of resist that is used for this method to remove equipment.
Therefore, for reach above-mentioned purpose of the present invention with and other objects and advantages, the resist removal methods comprises to be provided a kind of base material and form resist on this base material.Then base material is removed agent with the resist that contains N alkanol alkoxyl alkane acid amides and contact, so that remove resist from base material.
According to the inventive method on the other hand, base material removes composition with the resist that contains N alkanol alkoxyl alkane acid amides and etch inhibitor and contacts.Polar material can be added in the said composition.
According to the inventive method on the other hand, resist removes composition and contains alkanolamine and alkyl alkoxy alkanoate.Preferably, said composition also contains etch inhibitor and polar material.
In another aspect of this invention, the equipment that removes resist from base material comprises that the resist that contains N alkanol alkoxyl alkane acid amides removes the source.Feed unit communicates with above-mentioned source fluid, and resist removes agent and provides by it.Remove the unit with the resist of feed unit fluid communication and resist is removed agent send to and remove the base material of placing in the unit with resist and contact, thereby remove resist from base material.
In present device on the other hand, this source is that resist removes source.Said composition can be N alkanol alkoxyl alkane acid amides and etch inhibitor, perhaps can be alkanolamine and alkyl alkoxy alkanoate.Can both be added in the composition that provides with etch inhibitor or polar material or they.
Resist removal methods of the present invention can remove resist and polymer fully with simple process, with the short time, and don't the bottom of etch resist.Therefore used equipment is simpler and littler.
Fig. 1 is a flow chart, and wherein solid line represents to use resist of the present invention to remove agent or resist removes the method that composition removes resist, and dotted line represents to use the conventional procedures of being cancelled behind the present invention;
Fig. 2 removes the calcspar that resist that agent or resist remove composition removes equipment for using resist of the present invention;
Fig. 3 removes equipment drawing for the horizontal resist that uses resist of the present invention to remove composition;
Fig. 4 removes equipment drawing for the vertical resist that uses resist of the present invention to remove composition;
Fig. 5 removes the variation diagram of each constituent content in the composition for resist, and every interval was measured with gas chromatography in 8 hours in 48 hours.
Hereinafter will describe amide compound, resist and remove the method that agent and resist remove composition and prepare them. The present invention relates to remove equipment with the resist that they remove the method for resist and are used for this resist removal methods, hereinafter will at length be described.
Being used for novel amidation compound of the present invention is N chain triacontanol base alkoxyl alkane acid amides. In detail, this N chain triacontanol base alkoxyl alkane acid amides represents with formula (1):
R
4-O-R
3-CO-N-R
1R
2In OH (1) formula, R1Be hydrogen atom, C1-C
5Alkyl (acyclic hydrocarbon group that 1-5 carbon atom namely arranged) or have 1-3 the ring aromatic hydrocarbyl; R2Be C1-C
5Alkyl or have 1-3 the ring aromatic hydrocarbyl; R3And R4Independent separately is C1-C
5Alkyl. In preferred embodiments, R1Be hydrogen atom, R2For-CH2CH
2-，R
3For-CH2CH
2，R
4For-CH3。
Be used for amide compound of the present invention contain can play necleophilic reaction with resist hydroxyl (OH), and can (OH) play the alkoxyl (OR of hydrophilic reaction with hydroxyl4). Therefore, to remove agent be effectively removing aspect the resist to the present invention's resist of containing amide compound. So according to one embodiment of the invention, N chain alkyl alcohol alkoxyl acylamide compounds itself just consists of a kind of resist and removes agent.
In another embodiment, resist removes composition and contains N alkanol alkoxyl alkane acid amides and etch inhibitor. In addition, resist remove composition also the optional dipole moment that contains be 3 or larger polar material.
For example, remove in the composition at resist, according to the total weight of the composition, the content of N alkanol alkoxyl alkane acid amides is 50-99.9% (weight), and etch presses down the content of agent agent and can be 0.01-30% (weight). In preferred embodiments, the content of N chain triacontanol base alkoxyl alkane acid amides is 70-90% (weight), and the content of etch inhibitor is 7-15% (weight). In addition, its dipole moment be 3 or the content of larger polar material can be 0.01-30% (weight), be preferably 3-20% (weight).
N alkanol alkoxyl alkane acid amides is the compound of expression in the above-mentioned formula (1). The etch inhibitor is shown in the following formula (2):
R
6-(OH)
n(2) in the formula, R6Be C1-C
5Alkyl, have-C of COOH base1-C
5Alkyl, the aromatic hydrocarbyl of 1-3 ring is arranged or 1-3 ring arranged and at least one encircles, have-aromatic hydrocarbyl of COOH base. The numerical value of Integer n is 1-4. In preferred embodiments, R6Be phenyl ring, and the etch inhibitor is catechol, wherein n is 2. In addition, gallate is the etch inhibitor that general known formula (2) represents, it can be used for the present invention.
For dipole moment is 3 or bigger polar material, can make water, formic acid or methyl-sulfoxide.Dipole moment be 3 or bigger polar material for crosslinked polymer and resist high solubility is arranged.In other words, such polar material can remove the polymer on the bottom surface of the sidewall of resist figure of strong bond connection and exposure effectively.In addition, such polar material also makes resist remove and itself becomes easy.
Be used for another embodiment that resist of the present invention removes composition and contain alkanolamine (it is a kind of amines) and alkyl alkoxy alkanoate (it is a kind of ester compounds).In addition, can choose also that to contain etch inhibitor or dipole moment be 3 or bigger polar material wantonly, or these two kinds of materials.
For example, in this embodiment, the content of alkanolamine is the 10-70% (weight) that resist removes composition, and the content of alkyl alkoxy alkanoate is 10-70% (weight).In preferred embodiments, the content of alkanolamine is 30-40% (weight), and the content of alkyl alkoxy alkanoate is 30-40% (weight).
In this embodiment, the content of etch inhibitor is the 0.01-30% (weight) that resist removes composition.In preferred embodiments, the content of etch inhibitor is 7-15% (weight).In addition, the content of polar material is the 0.01-30% (weight) that resist removes composition.In preferred embodiments, the content of polar material is 3-20% (weight).
Be applicable to N alkanolamine of the present invention following formula (3) expression:
R
1-NH-R
2In OH (3) formula, R
1Be hydrogen atom, C
1-C
5The aromatic hydrocarbyl of alkyl or 1-3 ring; R
2Be C
1-C
5Alkyl or have 1-3 the ring aromatic hydrocarbyl.In preferred embodiments, R
1Be hydrogen, R
2Be monoethanolamine, promptly-CH
2CH
2-.
Be applicable to alkyl alkoxy alkanoate of the present invention following formula (4) expression:
R
4-O-R
3-COO-R
5(4) in the formula, R
3, R
4And R
5Independent separately is C
1-C
5Alkyl.Preferred alkyl alkoxy alkanoate is methyl methoxy base propionic ester, wherein R
3For-CH
2CH
2-, R
4For-CH
3And R
5For-CH
3
The reaction mechanism of the composition of last embodiment is described now.At first, shown in the following reaction equation (5), the necleophilic reaction mechanism by alkanolamine produces peeling off of resist.In addition, produce dissolving by the necleophilic reaction mechanism of hydroxyl in the alkanolamine and the hydrophilic reaction mechanism of the alkoxyl in the alkyl alkoxy alkanoate.In addition, the etch inhibitor can prevent effectively that bottom (being specially metal level) is subjected to etch.In addition, polar material for example water the effect that removes of polymer is strengthened.
For convenience of explanation, the mechanism described in the reaction equation (5) is R
1Situation for hydrogen.
In order to generate composition fully, composition can be heated to room temperature to about 120 ℃.In preferred embodiments, composition is heated to about 80 to about 90 ℃.The reason of above-mentioned measure is in order to accelerate the reaction of each combination in the reaction equation (5), to obtain N alkanol alkoxyl alkane acid amides.On the other hand, can with catalysts for example platinum be added in the reaction equation (5), so that accelerated reaction.
Being used for resist of the present invention removes composition and lists following table 1 in.In table 1, provide the content of preferred ingredient in the bracket.
Table 1: resist removes composition
| Remove the composition of resist | N alkanol alkoxyl alkane acid amides (% (weight)) | Alkanolamine (% (weight)) | Alkyl alkoxy alkanoate (% (weight)) | Etch inhibitor (% (weight)) | Polar material (% (weight)) |
| ????1 | 50 to 99.9 | 0.01 to 30 | |||
| ????2 | 50 to 99.9 (70 to 90) | 0.01 to 30 (7 to 15) | 0.01 to 30 (3 to 20) | ||
| ????3 | 10 to 70 | 10 to 70 | |||
| ????4 | 10 to 70 (30 to 40) | 10 to 70 (30 to 40) | 0.01 to 30 | ||
| ????5 | 10 to 70 (30 to 40) | 10 to 70 (30 to 40) | 0.01 to 30 (7 to 15) | 0.01 to 30 (3 to 20) |
Being used for resist of the present invention removes agent and resist and removes composition and have the fabulous ability that removes resist and polymer (etch by-products).In addition, the layer below their not etches resist, for example metal level.In addition, to remove each component of composition than traditional resist more cheap for above-mentioned material.
N alkanol alkoxyl alkane acid amides (amide compound of the present invention) prepares by the method below the present invention.At first, will as the alkanolamine shown in the formula (3) of amines with mix as the alkyl alkoxy alkanoate shown in the formula (4) of ester compounds.The weight mixing ratio of alkanolamine and alkyl alkoxy alkanoate is 1: 1.Secondly, with amine and ester reaction, make the N alkanol alkoxyl alkane acid amides shown in the formula (1).For enough reaction energies are provided, the temperature of mixture is remained on room temperature to about 120 ℃.In the preferred embodiment of this method, mixture is heated to about 80 to about 90 ℃.
The resist of explanation removes composition 1 or 2 by the N alkanol alkoxyl alkane acid amides of method for preparing and etch inhibitor or polar material or both are prepared by the mixed that suits in the table 1.
In addition, can prepare composition 1 or 2 by the following method.At first, 10-70% (weight) alkanolamine and 10-70% (weight) alkyl alkoxy alkanoate and 0-30% (weight) etch inhibitor or 0-30% (weight) polar material or both are mixed.Then, the temperature with mixture remains on room temperature to about 120 ℃.In the preferred embodiment of this method, mixture is heated to about 80 to about 90 ℃.Reaction time is about 1 to about 24 hours, preferred about 1 to 12 hour.After the heating, allow reactant place 1-7 hour, make chemical reactant stable.
Therefore, make mainly by N alkanol alkoxyl alkane acid amides and etch inhibitor or polar material or composition that both form.A spot of unreacted alkanol amine and alkyl alkoxy alkanoate can exist.
Can detect by an unaided eye or with gas chromatography confirm the reaction finish.In naked eyes are identified,, observe the layer that separates between each component and disappear along with the process of reaction.When observing the component layers complete obiteration that separates, just think to react and finish.When with the gas chromatographic analysis composition, the area percent of N alkanol alkoxyl alkane acid amides just shows to react above 80% to be finished.The area that area percent is defined as peak relevant with a certain component in the gas-chromatography sample divided by the area at all peaks of all components and, multiply by 100 again.
In the preparation of composition 3-5, each component is pressed the listed mixed of table 1, they were reacted 1-24 hour down for extremely about 120 ℃ in room temperature.Usually, being used to remove before the resist, make these compositions 3-5 earlier.But,, can save above-mentioned reactions steps of separating so if might make the temperature of composition 3-5 contact resist be set in said temperature.
With reference to the solid line step among Fig. 1 the method that the present invention removes resist is described.Should be pointed out that traditional method represents with solid line step among Fig. 1 and dotted line step.Make the various processes of semiconductor element, for example etching (dry method or wet type) process or ion implantation process all use the resist figure to carry out as shelter.Subsequently, the resist that the base material and the table 1 of top formation resist figure is listed removes agent or composition contacts, so that remove resist or polymer or both (step 110).Remove composition and put into groove by resist being removed agent or resist, base material is immersed finish in the groove this step then.On the other hand, when base material moves by sprayer, resist can be removed agent or resist and remove composition spray to base material.
In removing step, can be made into resist and remove agent, resist is removed composition 1 and 2 mix, can contact with base material immediately then, so that remove resist.At first the composition 3-5 shown in the table 1 is mixed, also can contact with base material immediately then; But, preferably removing before the step, composition 3-5 reaction certain hour.This is reflected at room temperature and carried out 1-12 hour under about 120 ℃, even can carry out under the condition that does not heat.In preferred embodiments, after reaction is finished even again through after a while, after for example reaction is passed through 1-7 hour after finishing again, composition is contacted with the base material that resist is arranged.
Use these compositions, resist removal methods of the present invention can be carried out under the low temperature below 70 ℃ or 70 ℃, carries out under 45-70 ℃ particularly.Be preferably about 10 to about 30 minutes time of contact.
On the other hand, when the works that forms on the base material has high thermal endurance, the composition 3-5 that does not heat can be placed on resist and remove in the unit and contact with base material.Subsequently, the temperature that the adjustment that resist can be removed the unit can be reacted to amine and ester (room temperature and more than the room temperature) is so that generate acid amides.Then, can occur simultaneously generating the reaction of acid amides and the reaction that resist removes from base material by composition.That is to say, in this case, removing before the step, can save the separately step of reaction of composition 3-5.
It is that resist removes agent or resist and removes the resist that composition can be used for being applicable to the shortwave irradiation that resist removes material, for example the resist in the resist of ArF excimer laser (193 nanometer) and traditional i line (365 nanometer) source or the resist of KrF excimer laser (248 nanometer).
After resist removes fully, wash (step 130) with remaining in the resist that resist on the base material removes material and dissolving.With cleaning solution for example deionized water carry out cleaning step.If desired, cleaning step can be undertaken by two steps.At last, air is used to dry substrate as the Rotary drying method of drier or with isopropyl alcohol as the seasoning of drier, so that remove the deionized water (step 140) that remains on the base material.
Behind the drying steps 140, base material is sent to subsequently procedure of processing.When forming the resist shelter in the step subsequently, after the step of finishing subsequently, remove resist by step shown in Figure 1.Remove step by such repetitive manufacture process and resist and make semiconductor element.
As shown in Figure 1, removing material the fabulous ability that removes resist or polymer is arranged because be used for resist of the present invention, is unnecessary so remove step 100 (dotted line) in advance, and this point is different with traditional technology.In addition because the layer below the resist is not weathered, after remove step 120 (dotted line) and also can save, these are also different with conventional art.Therefore, compare with traditional resist subtractive process, according to the present invention, available simpler process removes resist fully.So, can improve the productivity ratio of semiconductor element greatly.
In addition, as mentioned above, because the resist subtractive process more simplifies, resist of the present invention removes equipment and can make forr a short time or compacter.
Referring to Fig. 2, resist of the present invention removes equipment 200 and comprises that simply resist removes unit 210, cleaning unit 220 and drying unit 230.That is to say, traditional remove in advance the unit and after to remove the unit be unnecessary.Therefore, compare with traditional technology, resist removes equipment 200 shared areas and can reduce significantly.
Resist of the present invention removes the unit, and to remove material source with the resist that is used for the inventive method be fluid communication.
Remove under the situation that equipment 200 uses acid wash at resist, unit 210,220 and 230 is separately corresponding to a groove independently.Therefore, different with traditional technology, nitric acid (HNO
3) remove in advance that to remove treatment trough behind treatment trough and the isopropyl alcohol (IPA) be unnecessary, therefore can remove this two grooves, remove the shared area of equipment 200 thereby significantly reduced resist.
The resist of use spray-on process removes equipment and can be divided into horizontal and vertical two kinds.
Referring to Fig. 3, horizontal resist removes equipment 300 and uses a kind of horizontal feed equipment 340, and for example a kind of conveyer system is divided into resist with this equipment and removes unit 310, cleaning unit 320 and drying unit 330.Resist removes material source 360 N alkanol alkoxyl alkane acid amides or alkanolamine and alkyl alkoxy alkanoate.This source and resist remove unit 310 for example by feed unit 370 fluid communication.Traditional cleaning solution source 362 and drier source 364 are also arranged respectively, also can be by feed unit 370 and separately unit 320 and 330 fluid communication.Nozzle 312,322 and 332 is installed in each unit, is used to spray be applicable to the material of unit separately.Specifically, nozzle 312 is installed in resist and removes unit 310.In operation, when base material is put into resist and removed unit 310, resist of the present invention is removed material from nozzle 312 sprayings, so that remove resist.Then, by delivery system 340 the base material continuous horizontal is transported to cleaning unit 320.In cleaning unit 320, cleaning solution is sprayed by nozzle 322.At last, by delivery system 340 base material is transported to drying unit 330.Be sprayed to drier air or dry carry out drying for example on the base material with nozzle 332 with chemicals.Have only three unit because horizontal resist removes equipment, thereby the size of equipment can reduce greatly.
Referring to Fig. 4, a kind of vertical resist removes equipment 400 and uses a kind of substrate holder 440 that can vertically move.The feed unit 470 that resist of the present invention removes material source 460 and provides resist to remove material also is provided vertical equipment.In preferred embodiments, substrate holder 440 is rotatable.In addition, there are three bed shape structural regions the inside of this equipment, their hard each other in line row, but be not chamber independently.That is to say that these unit remove zone 410 by arid region 430, cleaning zone 420 and resist and form by the straight order of heavily fortified point.Also cleaning solution source 462 and drier source 464 can be arranged respectively, these materials can be carried by feed unit 470.In this embodiment, single feed line 450 can be all three unit separately material is provided.
For example, when base material was placed on the substrate holder 440, support 440 at first moved to and carries out the zone that resist removes, and the resist that removes source 460 from resist removes material through feed unit 470, by feed line 450 sprayings.In preferred embodiments, resist removes material and is discharged into outside the equipment by the discharge pipe line (not shown).When resist removed step and finishes, substrate holder 440 moved to cleaning unit 420 by general who has surrendered's base material down.By feed line 450 cleaning solution is sprayed to cleaning unit 420 then.At last, take base material to drying unit 430, carry out drying by substrate holder is vertically mobile.
Though Fig. 4 illustrates drying unit 430, cleaning unit 420 and resist and removes unit 410 by vertically arranging the end of to the order on top that these unit also can vertically be arranged by opposite order.
Have only three unit because vertical resist of the present invention removes equipment, therefore compare with traditional vertical equipment, its size reduces greatly.
With reference to following examples the present invention is described in further detail, but should be appreciated that and the invention is not restricted to these specific embodiments.
The preparation of example I N ethanol methoxy propyl acid amides
In this embodiment, will mix as 200 milliliter monoethanolamines of alkanolamine with as 200 milliliters of methyl methoxy base propionic esters of ester.Subsequently, mixture was heated 5 hours down at 90 ℃.After the heating, reactant was at room temperature put 5 hours.
With the material that gc analysis generates, determine to have made N ethanol methoxy propyl acid amides product.Usefulness proton magnetic resonance (PMR) in addition, (
1H-NMR) analysis of spectrum product, the relative quantity of each component is represented with ppm.The NMR data of product are as follows: 6.8ppm (1H), 3.7ppm (4H), 3.5ppm (3H) and about 2.8ppm (1H).
Example II N, the preparation of N-tert-butyl group ethanol methoxy propyl acid amides
In this enforcement, will be as 200 milliliters of N of alkanolamine, N-tert-butyl group monoethanolamine and mix as 200 milliliters of methyl methoxy base propionic esters of ester.Subsequently, mixture was heated 5 hours down at 90 ℃.After the heating, reactant was at room temperature put 5 hours.
With the material that gc analysis generates, determine to have made N, N-tert-butyl group ethanol methoxy propyl acid amides.
The evaluation of EXAMPLE III preference temperature in preparation N ethanol methoxy propyl acid amides
In this embodiment, will mix as 200 milliliters of monoethanolamines of alkanolamine with as 200 milliliters of methyl methoxy base propionic esters of ester.Subsequently,, under the listed different temperatures of table 2, synthesize N ethanol methoxy propyl acid amides, and measure and finish this synthetic time of being consumed in order to determine to be fit to the reaction temperature of this amine and ester.Area % by gc analysis acid amides (N ethanol based methoxy propyl acid amides) determines the synthetic time of finishing above 80% elapsed time.
The reaction temperature and the time of table 2:N ethanol methoxy propyl acid amides
| Reaction temperature (℃) | ????25 | ??35 | ??45 | ??55 | ??65 | ??80 | ??90 |
| Reaction time (hour) | ????55 | ??24 | ??30 | ???7 | ???6 | ???4 | ???3 |
Can draw from The above results, be reflected under the room temperature and take place, row gets rapider when reacting under higher temperature.But, consider other processing conditions, preferable reaction temperature is no more than 120 ℃.Therefore, the temperature for preparing amide compound of the present invention is wished between room temperature to 120 ℃.In the preferred embodiment of this method, reaction temperature is about 80 to about 90 ℃ of scopes.
The EXAMPLE IV resist removes preparation of compositions and it is removed the evaluation of resist
As shown in table 3, prepare 7 kinds of resists with monoethanolamine (MEA), methyl methoxy base propionic ester (MMP), catechol and the water of different content and removed composition.Subsequently, these compositions were heated 5 hours down at 80 ℃.Then, the material that generates was at room temperature put 6 hours, made composition react complete.
Table 3: the resist of several compositions removes performance
| Project | MEA (milliliter) | MMP (milliliter) | Catechol (g) | Water (milliliter) | Observed result |
| ???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, ◎: better, ⊙: best)
Preparation will remove the resist that composition removes with above-mentioned resist on every kind of 7 plate substrate with the following methods.At first, make Boro PhosphoSilicate Glass (BPSG) layer of thickness 5000 dusts.Then, each is titanium layer and the titanium nitride layer and the heating of 200 dusts to make thickness.Secondly, with the aluminium layer deposition of thickness 6000 dusts, arrive next operation then.On aluminium lamination, make titanium nitride layer and lead, make the intermediate dielectric layer of thickness 10000 dusts then as binding.Then, resist-coating on intermediate dielectric layer, and is carried out the resist figure that optical graving becomes passage to determine.Baking resist figure comes etching intermediate dielectric layer as shelter by the oxide etching agent through buffering with the resist figure then, forms the aluminium lamination that passage exposes.
After making passage, 7 kinds of base materials immersions are equipped with in 7 grooves of the listed 7 kinds of compositions of table 3.The temperature of groove is remained on 60 ℃.After the submergence 20 minutes, water cleans base material 5 minutes, and is dry then, uses scanning electron microscopy (SEM) observation base material again.On the basis of SEM observed result, it is good, better, best that base material is classified as, and with symbol grade is shown in table 3.The situation of base material characterizes with the relative populations of residual polymer and photoresist.Good situation is the situation that the known traditional resist of similar use those skilled in the art removes composition.Better situation improves to some extent for comparing with traditional situation; Best state is to have compared significant improvement with traditional situation.
The evaluation that EXAMPLE V suits process time
In order to determine suitable process time, use in the table 3 composition corresponding to 4, resist removed under the different process times shown in the table 4.Identical in other processing conditions and the EXAMPLE IV.The situation that removes of resist and the etch situation of aluminium lamination and silicon layer are observed with SEM.The symbol of representing the situation that removes in table 4 is identical with table 3.In table 4, x represents that bottom does not weather.
Listed result can find out from table 4, and the suitable reaction time that removes resist is 10-30 minute.
Table 4: the time removes Effect on Performance to resist
(◎: better, ⊙: best)
| Project | MEA (milliliter) | MMP (milliliter) | Catechol (gram) | Water (milliliter) | Time (branch) | Resist removes the observed result of ability | Etch is arranged or do not have etch (Al, Si) |
| ??1 | ??200 | ??200 | ???60 | ????100 | ??10 | ????⊙ | ?????× |
| ??2 | ??200 | ??200 | ???60 | ????100 | ??15 | ????◎ | ?????× |
| ??3 | ??200 | ??200 | ???60 | ????100 | ??20 | ????◎ | ?????× |
| ??4 | ??200 | ??200 | ???60 | ????100 | ??25 | ????◎ | ?????× |
| ??5 | ??200 | ??200 | ???60 | ????100 | ??30 | ????◎ | ?????× |
The detailed valency of the processing temperature that example VI is suitable
In order to determine suitable processing temperature, use table 3 listed corresponding to 4 composition, under the listed different processing temperatures of table 5, remove resist.Identical among other processing conditions and the embodiment 4.The situation that removes of resist and the etch situation of aluminium lamination and silicon layer are observed with SEM.Equally, x represents that bottom is not subjected to erosion, and circle is represented the erosion of bottom amine.
The result listed from table 5 can find out that the suitable reaction temperature that removes resist is at lower temperature range (about 45 to about 70 ℃), because bottom is not subjected to tangible etch in this scope.
Table 5: temperature removes Effect on Performance to resist
| Project | MEA (milliliter) | MMP (milliliter) | Catechol (gram) | Water (milliliter) | Temperature (℃) | Resist removes the observed result of ability | Etch is arranged or do not have etch (Al, Si) |
| ??1 | ??200 | ??200 | ???60 | ????100 | ??45 | ???◎ | ?????× |
| ??2 | ??200 | ??200 | ???60 | ????100 | ??50 | ???◎ | ?????× |
| ??3 | ??200 | ??200 | ???60 | ????100 | ??55 | ???◎ | ?????× |
| ??4 | ??200 | ??200 | ???60 | ????100 | ??60 | ???◎ | ?????× |
| ??5 | ??200 | ??200 | ???60 | ????100 | ??65 | ???◎ | ?????× |
| ??6 | ??200 | ??200 | ???60 | ????100 | ??70 | ???◎ | ?????× |
The example VII A resist removes the comparison of ability
In this embodiment, press the identical mode of embodiment 4, make passage with the resist figure, remove resist with the composition corresponding to 4 shown in the table 3, be 20 minutes process time, reaction temperature is 60 ℃.With the material that SEM observation generates, observed result is shown in Fig. 3.
In Comparative Examples, remove composition with traditional resist and remove resist, other conditions are same as the previously described embodiments, then the material that generates with SEM observation.Observed result is shown in Fig. 4.
When SEM photo relatively, people as can be seen, when using resist of the present invention to remove composition, resist is removed fully; And when using traditional resist to remove composition, resist partly keeps.In addition, bottom layer of aluminum is not subjected to etch in the present invention, and is using traditional resist to remove under the situation of component, and aluminium lamination is subjected to the part etch.
Example VII A I resist removes the consumption of each component of composition
In the resist subtractive process, removed the quantity of each component of composition with the gc analysis resist in per 8 hours, said composition is corresponding to the composition shown in the table 34.Analysis result is shown in Fig. 5, wherein-■-be the area % of acid amides ,-△-be the area % of monoethanolamine ,--be the area % of methyl methoxy base propionic ester.Can find out from result shown in Figure 5, even through after 48 hours, the area % of acid amides remains unchanged at about 80% place.In addition, the area % of monoethanolamine also remains on 3.4 constant.After through 24 hours, the area % of methyl methoxy base propionic ester drops to 0.5 from 0.9, and it becomes 0 basically after 40 hours.
Consider that active component main in the composition of the present invention is an acid amides, even the content of acid amides changes seldom and means that composition of the present invention can not consume during the course very soon after 48 hours, can use for a long time.This means that composition of the present invention can make productivity ratio improve, and can reduce manufacturing expense significantly, to remove composition different with traditional resist for it, and latter's replacing in essential per 24 hours once.
Amide compound of the present invention has the fabulous ability that removes resist.Therefore, the present invention has the resist of acid amides to remove agent or resist to remove composition the fabulous ability that removes resist is arranged, and can remove polymer and organometallic polymer effectively.In addition, the layer below the resist can not be subjected to etch.So, when using resist of the present invention to remove agent or resist to remove composition, needn't remove polymer remove step in advance and prevent bottom be subjected to etch after remove step.Therefore, can simplify the resist subtractive process and shorten process time.In addition, remove the required temperature of resist and can be set to lower temperature.Resist removes equipment also can be simplified and can be compacter.
Those skilled in the art are very clear, under the situation of essence of the present invention or scope, can make various improvement and change to the present invention.Therefore, the present invention's plan comprises these improvement of the present invention and change, as long as they are in the scope of appended claims and equivalent thereof.
Claims (44)
1. resist removal methods, this method comprises provides a kind of base material; On this base material, make resist; And this base material is removed agent with the resist that contains N alkanol alkoxyl alkane acid amides contact, resist is removed from base material.
2. according to the process of claim 1 wherein in described contact, N alkanol alkoxyl alkane acid amides is the compound of formula (1):
R
4-O-R
3-CO-N-R
1R
2OH(1)
In the formula, 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 the ring aromatic hydrocarbyl, R
3And R
4Independent separately is C
1-C
5Alkyl.
3. according to the method for claim 2, wherein in described contact: R
1Be hydrogen, R
2For-CH
2CH
2-, R
3For-CH
2CH
2-, R
4For-CH
3
4. also comprise cleaning base material and dry substrate according to the process of claim 1 wherein.
5. according to the process of claim 1 wherein that described contact carries out in about 45 to 70 ℃ temperature range.
6. according to the process of claim 1 wherein that described contact carries out to about 30 minutes time range about 10.
7. resist removal methods, this method comprises: a kind of base material is provided; On this base material, make resist; And make base material remove composition with the resist that contains N alkanol alkoxyl alkane acid amides and etch inhibitor to contact, so that remove resist from base material.
8. according to the method for claim 7, wherein in described contact process, N alkanol alkoxyl alkane acid amides is the compound of formula (1):
R
4-O-R
3-CO-N-R
1R
2OH??(1)
In the formula, R
1Be hydrogen, C
1-C
5Alkyl or have 1-3 the ring aromatic hydrocarbyl, R
2Be C
1-C
5Alkyl or the aromatic hydrocarbyl of 1-3 ring is arranged, and R
3And R
4Independent separately is C
1-C
5Alkyl.
9. according to the method for claim 7, wherein in described contact process, the etch inhibitor is the compound of formula (2):
R
6-(OH)
n??(2)
In the formula, R
6Be C
1-C
5Alkyl, have-C of COOH base
1-C
5Alkyl, the aromatic hydrocarbyl of 1-3 ring is arranged or have 1-3 ring reach-aromatic hydrocarbyl of COOH base and n are an integer among the 1-4.
10. according to the method for claim 7, wherein in described contact process, N alkanol alkoxyl alkane acid amides account for composition about 50 to about 99.9% (weight), and the etch inhibitor account for resist remove composition about 0.01 to about 30% (weight).
11. according to the method for claim 7, wherein also be included in and finish before the described contact, dipole moment is not less than about 3 polar material is mixed into resist and removes in the composition.
12. according to the method for claim 11, wherein in described mixed process, polar material account for resist remove composition about 0.01 to about 30% (weight).
13., wherein also comprise the cleaning base material according to right 7 methods; And dry substrate.
14. according to the method for claim 7, wherein said contact is carried out to about 70 ℃ temperature range about 45.
15. according to the method for claim 7, wherein said contact is carried out to about 30 minutes time range about 10.
16. a resist removal methods, this method comprises: a kind of base material is provided; On this base material, make resist; And base material removed composition and contact with containing the resist of alkanolamine with the alkyl alkoxy alkanoic acid ester, so that remove resist from base material.
17. according to the method for claim 16, wherein in described contact process, alkanolamine is the compound of formula (3):
R
1-NH-R
2OH????(3)
In the formula, 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 the ring aromatic hydrocarbyl.
18. according to the method for claim 16, wherein in described contact process, the alkyl alkoxy alkanoic acid ester is the compound of formula (4):
R
4-O-R
3-COO-R
5????(4)
In the formula, R
3, R
4And R
5Independent separately is C
1-C
5Alkyl.
19. according to the method for claim 16, wherein in described contact process, alkanolamine accounts for about 10 to 70% (weight) of composition, and the alkyl alkoxy alkanoic acid ester account for composition about 10 to about 70% (weight).
20. according to the method for claim 17, wherein in described contact process, R
1Be hydrogen, R
2For-CH
2CH
2-.
21. according to the method for claim 18, wherein in described contact process, R
3For-CH
2CH
2-, R
4For-CH
3And R
5For-CH
3
22. according to the method for claim 16, wherein also be included in and finish before the described contact, the etch inhibitor mixed is removed in the composition to resist.
23. according to the method for claim 22, wherein in described mixed process, the etch inhibitor is the compound of formula (2):
R
6-(OH)
n??(2)
In the formula, R
6Be C
1-C
5Alkyl, have-C of COOH base
1-C
5Alkyl, the aromatic hydrocarbyl of 1-3 ring is arranged or have 1-3 ring to reach-aromatic hydrocarbyl of COOH base, n is an integer among the 1-4.
24. according to the method for claim 22, wherein in described mixed process, the etch inhibitor account for resist remove composition about 0.01 to about 30% (weight).
25. according to the method for claim 16, wherein also be included in and finish before the described contact, dipole moment is not less than about 3 polar material is mixed into resist and removes in the composition.
26. according to the method for claim 25, wherein in described mixed process, polar material account for resist remove composition about 0.01 to about 30% (weight).
27. according to the method for claim 16, wherein said contact is carried out to about 120 ℃ temperature range in about room temperature.
28. according to the method for claim 16, wherein said contact is carried out in about 10 to 30 minutes time range.
29. according to the method for claim 16, wherein also be included in before the described contact, heat resist in about room temperature down to about 120 ℃ and remove composition.
30. according to the method for claim 29, wherein said contact is carried out to about 70 ℃ temperature about 45.
31., wherein also comprise the cleaning base material according to the method for claim 16; And dry substrate.
32. a resist removal methods, this method comprises: a kind of base material is provided; On this base material, form resist; And base material and resist are removed composition contact, so that remove resist from base material, resist removes composition and contains and account for composition about 10 alkanolamines to about 70% (weight), account for the alkyl alkoxy alkanoic acid ester of composition about 10 to about 70% (weight), account for the etch inhibitor of composition about 0.01, and account for composition about 0.01 to about 30% (weight), dipole moment and be not less than about 3 polar material to about 30% (weight).
33., wherein also be included in before the described contact according to the method for claim 32, heat resist in about room temperature down to about 120 ℃ and remove composition, wherein to about 70 ℃ temperature range, contact about 45.
34., wherein to about 120 ℃ temperature range, carry out described contact in about room temperature according to the method for claim 32.
35., to about 30 minutes time range, carry out described contact about 10 according to the method for claim 33.
36., to about 30 minutes time range, carry out described contact about 10 according to the method for claim 34.
37. one kind removes the equipment of resist from base material, this equipment comprises: the resist that contains N alkanol alkoxyl alkane acid amides removes the agent source; With the feed unit that described source fluid communicates, resist removes agent by its feed; And remove the unit with the resist of feed unit fluid communication, send into resist and remove agent and contact, thereby remove resist from base material with remove the base material of handling in the unit at resist.
38. one kind removes the equipment of resist from base material, this equipment comprises: the resist that contains N alkanol alkoxyl alkane acid amides and etch inhibitor removes source; The feed unit that communicates with this source fluid provides resist to remove composition by it; And remove the unit with the resist of feed unit fluid communication, be used for sending into resist and remove composition and contact, thereby remove resist from base material with remove the base material of placing in the unit at resist.
39. one kind removes the equipment of resist from base material, this equipment comprises: the resist that contains alkanolamine and alkyl alkoxy alkanoate removes source; With the feed unit that this source fluid communicates, resist removes composition and provides by it; And remove the unit with the resist of feed unit fluid communication, and be used for sending into resist and remove composition, contact with remove the base material of placing in the unit at resist, thereby remove resist from base material.
40. equipment that removes resist from base material, this equipment comprises: a kind of resist removes source, it contains and accounts for composition about 10 alkanolamines to about 70% (weight), account for the alkyl alkoxy alkanoate of composition about 10 to about 70% (weight), account for the etch inhibitor of composition about 0.01, and account for composition about 0.01 to about 30% (weight), dipole moment and be not less than about 3 polar material to about 30% (weight); With the feed unit that this source fluid communicates, resist removes composition and provides by it; And remove the unit with the resist of feed unit fluid communication, and be used for sending into resist and remove composition, contact with remove the base material of handling in the unit at resist, thereby remove resist from base material.
41., wherein also comprise the cleaning solution source according to claim 37,38,39 or 40 equipment; Remove with resist that the unit is connected, and the cleaning unit that communicates with the cleaning solution source fluid, be used for removing the back and clean with cleaning solution and to remove the base material of placing in the unit at resist at resist; The drier source; And be connected with cleaning unit, and the drying unit that communicates with the drier source fluid is stayed the cleaning solution on the base material of handling in the drying unit with the drier drying.
42. according to the equipment of claim 41, wherein resist removes the unit and comprises and remove groove; Cleaning unit comprises and is different from the rinse bath that removes groove; And drying unit comprises and is different from the dry slot that removes groove and rinse bath.
43. equipment according to claim 41, wherein also comprise and remove groove with resist, the combination transfer device that rinse bath is connected with dry slot, be used for that base material is removed the unit from resist and be transported to drying unit by cleaning unit, wherein resist removes the unit and also comprises first nozzle with the feed unit fluid communication, be used for that resist is removed agent and resist removes composition spray to base material, cleaning unit also comprises and second nozzle of cleaning solution source by the feed unit fluid communication, be used for cleaning solution is sprayed to base material, and drying unit also comprises and three nozzle of drier source by the feed unit fluid communication, is used for drier is sprayed to base material.
44. the equipment according to claim 41 wherein also comprises: a kind of vertical substrate holder, it carries base material and removes unit, cleaning unit and drying unit along resist and vertically move; Remove the feeder sleeve of material source fluid communication by feed unit and cleaning solution source, drier source and resist, be used for removing material, cleaning solution and drier to the base material resist of spraying successively, wherein resist removes unit, cleaning unit and drying unit and vertically arranges each other, and wherein resist to remove material be that resist removes agent and resist removes one of composition.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR32355/1998 | 1998-08-05 | ||
| KR19980032355 | 1998-08-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1244029A true CN1244029A (en) | 2000-02-09 |
Family
ID=19546809
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 98123847 Pending CN1244029A (en) | 1998-08-05 | 1998-11-05 | Method and apparatus for removing corrosion inhibitor |
Country Status (5)
| Country | Link |
|---|---|
| CN (1) | CN1244029A (en) |
| FR (1) | FR2782175A1 (en) |
| GB (1) | GB9823967D0 (en) |
| SG (1) | SG76567A1 (en) |
| TW (1) | TW594442B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104014497A (en) * | 2013-02-28 | 2014-09-03 | 细美事有限公司 | Nozzle assembly, substrate treatment apparatus, and method of treating substrate |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100434491B1 (en) | 2001-08-17 | 2004-06-05 | 삼성전자주식회사 | Resist or etching by-products removing composition and resist removing method using the same |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4722355A (en) * | 1985-08-19 | 1988-02-02 | Rolf Moe | Machine and method for stripping photoresist from wafers |
| GB2199587B (en) * | 1986-12-10 | 1991-03-27 | Advanced Chem Tech | Stripping compositions and use therof |
| US5690747A (en) * | 1988-05-20 | 1997-11-25 | The Boeing Company | Method for removing photoresist with solvent and ultrasonic agitation |
| US5204026A (en) * | 1988-05-20 | 1993-04-20 | The Boeing Company | Solvent with alicyclic carbonate and ethylene dipropionate |
| JPH02253265A (en) * | 1989-03-28 | 1990-10-12 | Nippon Zeon Co Ltd | Resist peeling agent |
| US5753601A (en) * | 1991-01-25 | 1998-05-19 | Ashland Inc | Organic stripping composition |
| US5753135A (en) * | 1995-10-23 | 1998-05-19 | Jablonsky; Julius James | Apparatus and method for recovering photoresist developers and strippers |
| KR100234532B1 (en) * | 1996-09-21 | 1999-12-15 | 윤종용 | Thinner composition used in cleaning photoresist and semiconductor manufacturing method using the same |
-
1998
- 1998-10-21 TW TW87117417A patent/TW594442B/en not_active IP Right Cessation
- 1998-10-21 SG SG1998004235A patent/SG76567A1/en unknown
- 1998-11-02 GB GBGB9823967.6A patent/GB9823967D0/en not_active Ceased
- 1998-11-04 FR FR9813857A patent/FR2782175A1/en active Pending
- 1998-11-05 CN CN 98123847 patent/CN1244029A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104014497A (en) * | 2013-02-28 | 2014-09-03 | 细美事有限公司 | Nozzle assembly, substrate treatment apparatus, and method of treating substrate |
Also Published As
| Publication number | Publication date |
|---|---|
| SG76567A1 (en) | 2000-11-21 |
| TW594442B (en) | 2004-06-21 |
| GB9823967D0 (en) | 1998-12-30 |
| FR2782175A1 (en) | 2000-02-11 |
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