CN103605268A - Cleaning liquid used during semiconductor manufacturing process - Google Patents
Cleaning liquid used during semiconductor manufacturing process Download PDFInfo
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- CN103605268A CN103605268A CN201310511175.4A CN201310511175A CN103605268A CN 103605268 A CN103605268 A CN 103605268A CN 201310511175 A CN201310511175 A CN 201310511175A CN 103605268 A CN103605268 A CN 103605268A
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Abstract
The present invention provides a cleaning liquid, which comprises pentaerythritol, potassium hydroxide, an organic amine, an anticorrosion agent and a solvent. The cleaning liquid has characteristics of strong photosensory membrane cleaning ability and low corrosion on semiconductor wafer patterns and substrates.
Description
Technical field
The present invention relates to semiconductor technology manufacturing technology field, relate in particular to a kind of light-sensitive surface cleaning fluid.
Background technology
Photosensitive material is a kind of emerging material, is widely used in semiconductor manufacturing industry.In common semiconductor fabrication process, by form the mask of light-sensitive surface on the surface of some materials, after exposure, carry out figure transfer, after obtaining the figure needing, before carrying out next process, need to peel off residual light-sensitive surface.In this process, require to remove completely unwanted light-sensitive surface, can not corrode any base material simultaneously.
At present, light-sensitive surface cleaning fluid is mainly comprised of polar organic solvent, highly basic and/or water etc., by semiconductor wafer being immersed in cleaning fluid or utilizing cleaning fluid to rinse semiconductor wafer, removes the light-sensitive surface on semiconductor wafer.As JP1998239865 discloses a kind of cleaning fluid, its composition is Tetramethylammonium hydroxide (TMAH), dimethyl sulfoxide (DMSO) (DMSO), 1,3 '-dimethyl-2-imidazolidinone (DMI) and water.Wafer is immersed in this cleaning fluid, at 50～100 ℃, remove light-sensitive surfaces more than 20 μ m in metal and dielectric substrate; It is slightly high to the corrosion of semiconductor wafer base material, and can not remove the light-sensitive surface on semiconductor wafer completely, and cleansing power is not enough; US5529887 forms alkaline cleaning fluid by potassium hydroxide (KOH), alkylene glycol monoalkyl ether, soluble fluoride and water etc., and wafer is immersed in this cleaning fluid, removes the thick film light-sensitive surface in metal and dielectric substrate at 40～90 ℃.Its corrosion to semiconductor wafer base material is higher; US5091103 discloses 1-METHYLPYRROLIDONE, 1, the cleaning fluid of 2-propylene glycol and Tetramethylammonium hydroxide, at 105～125 ℃, remove the light-sensitive surface that cured (hard bake) through high temperature, it is characterized in that not containing water, operating temperature is high, once cleaning fluid is sneaked into water, its corrosion rate to metallic aluminium and copper all rises.
As can be seen here, find and more effectively to suppress the metal erosion method of inhibitioning and efficient light-sensitive surface removal ability is that such light-sensitive surface cleaning fluid is made great efforts improved privileged direction.
Summary of the invention
The technical problem to be solved in the present invention is exactly that the cleansing power that exists for existing light-sensitive surface cleaning fluid is not enough or to wafer pattern and the stronger defect of base material corrosivity, and provides a kind of light-sensitive surface cleansing power strong and to semiconductor wafer pattern and the lower light-sensitive surface cleaning fluid of base material corrosivity.
For solving the problems of the technologies described above, the invention provides a kind of novel light-sensitive surface cleaning fluid, it comprises pentaerythrite, potassium hydroxide, organic amine, anticorrosive and solvent.
Wherein, the mass percent of pentaerythrite is 0.1-15%, and the mass percent of potassium hydroxide is 0.1-10%, and the mass percent of organic amine is 0.5-30%, anticorrosive 0.5-5%, and solvent is She's amount, each constituent mass number percent sum is 100%.
Further, the mass percent of pentaerythrite is 10%, and the mass percent of potassium hydroxide is 8%, and the mass percent of organic amine is 25%, anticorrosive 3%, and solvent is 54%.
Wherein, described machine amine for be selected from comprise monoethanolamine, isopropanolamine, amino ethoxy ethanol, n-methylethanolamine, dimethylethanolamine, diethyl ethanolamine, 2-aminoethyl ethylaminoethanol, at least one compound of group of aminoethyl piperazine, aminopropyl piperazine, 1-(2-hydroxyethyl) piperazine, 1-amino-4-methyl piperazine, 2-methyl piperazine, 1-methyl piperazine, 1-benzyl diethylenediamine, 2-phenylpiperazine, 1-aminoethyl piperidine, 1-amino piperidine and 1-aminomethyl piperidines.
Wherein, described solvent is one or more in sulfoxide, sulfone, imidazolidinone, imidazolone, alcohol, ether, acid amides.
Wherein, described sulfoxide is dimethyl sulfoxide (DMSO); Described sulfone is sulfolane; Described imidazolidinone is 1,3-dimethyl-2-imidazolidinone; Described imidazolone is DMI; Described acid amides is dimethyl formamide, dimethyl acetamide; Described alcohol is propylene glycol, diethylene glycol; Ether is glycol ether or propylene glycol.
Wherein, described glycol ether is ethylene glycol ethyl ether, butyl glycol ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether; Described propylene glycol is propylene-glycol ethyl ether, propandiol butyl ether, dipropylene glycol monomethyl ether, DPE, Dipropylene glycol mono-n-butyl Ether.
Described anticorrosive is by O ', and O '-Diphenyl disulfide is for phosphoric acid-N, TMSDEA N diethylamine and ω, and ω '-bis-(benzimidazolyl-2 radicals-yl) alkane forms, and both quality are 1:1～1:2.
Described ω, ω '-bis-(benzimidazolyl-2 radicals-yl) alkane represents by formula 1, wherein, n=8.
Described O ', O '-Diphenyl disulfide is for phosphoric acid-N, and TMSDEA N diethylamine is represented by formula 2.
Wherein, described O ', O '-Diphenyl disulfide is for phosphoric acid-N, and the preparation method of TMSDEA N diethylamine is specially:
By 22.2g phosphorus pentasulfide (0.1mol), 37.6g phenol (0.4mol) joins in 250mL there-necked flask, adds 70mL toluene to make solvent; Gradually temperature is elevated to while stirring to about 100 ℃ reaction 45min; Heat up again until reflux, backflow 3h, in course of reaction, solid fades away; Solution is slightly cold, adds a small amount of activated charcoal boiling decoloring, filters while hot, and filtrate is cooled to room temperature; Gained filtrate is transferred in beaker, and water-bath is cooling and under agitation dropwise drip 22mL diethylamine (0.2mol), and reaction system is emitted a large amount of heat, liquid color gradually becomes Chinese red, use glass bar rapid stirring, have precipitation to produce, one night of static placement under room temperature; Filtration under diminished pressure, by toluene wash, to white, product is white needle-like crystals; Toluene recrystallization, filtration under diminished pressure, vacuum drying, obtains white crystal, obtains.
Wherein, described ω, the preparation method of ω '-bis-(benzimidazolyl-2 radicals-yl) alkane is specially:
Take respectively 0.11mol o-phenylenediamine and 0.05mol fat diacid, in mortar, fully grind it is mixed, be transferred in three-neck flask.Add nitration mixture, logical nitrogen, heating reflux reaction under mechanical raking.TLC tracking and monitoring finishes to reaction, and about 10h, pours in 250mL beaker, standing cooling, with strong aqua, regulates pH=7.Standing over night at 4 ℃, suction filtration is dry, and gained crude product methanol/water recrystallization, obtains sterling.
Beneficial effect of the present invention:
Light-sensitive surface cleaning fluid light-sensitive surface cleansing power provided by the invention is strong and lower to semiconductor wafer pattern and base material corrosivity.
Embodiment
A novel light-sensitive surface cleaning fluid, it comprises pentaerythrite, potassium hydroxide, organic amine, anticorrosive and solvent.
Wherein, the mass percent of pentaerythrite is 0.1-15%, and the mass percent of potassium hydroxide is 0.1-10%, and the mass percent of organic amine is 0.5-30%, anticorrosive 0.5-5%, and solvent is She's amount, each constituent mass number percent sum is 100%.
Further, the mass percent of pentaerythrite is 10%, and the mass percent of potassium hydroxide is 8%, and the mass percent of organic amine is 25%, anticorrosive 3%, and solvent is 54%.
Wherein, described machine amine for be selected from comprise monoethanolamine, isopropanolamine, amino ethoxy ethanol, n-methylethanolamine, dimethylethanolamine, diethyl ethanolamine, 2-aminoethyl ethylaminoethanol, at least one compound of group of aminoethyl piperazine, aminopropyl piperazine, 1-(2-hydroxyethyl) piperazine, 1-amino-4-methyl piperazine, 2-methyl piperazine, 1-methyl piperazine, 1-benzyl diethylenediamine, 2-phenylpiperazine, 1-aminoethyl piperidine, 1-amino piperidine and 1-aminomethyl piperidines.
Wherein, described solvent is one or more in sulfoxide, sulfone, imidazolidinone, imidazolone, alcohol, ether, acid amides.
Wherein, described sulfoxide is dimethyl sulfoxide (DMSO); Described sulfone is sulfolane; Described imidazolidinone is 1,3-dimethyl-2-imidazolidinone; Described imidazolone is DMI; Described acid amides is dimethyl formamide, dimethyl acetamide; Described alcohol is propylene glycol, diethylene glycol; Ether is glycol ether or propylene glycol.
Wherein, described glycol ether is ethylene glycol ethyl ether, butyl glycol ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether; Described propylene glycol is propylene-glycol ethyl ether, propandiol butyl ether, dipropylene glycol monomethyl ether, DPE, Dipropylene glycol mono-n-butyl Ether.
Described anticorrosive is by O ', and O '-Diphenyl disulfide is for phosphoric acid-N, TMSDEA N diethylamine and ω, and ω '-bis-(benzimidazolyl-2 radicals-yl) alkane forms, and both quality are 1:1～1:2.
Described ω, ω '-bis-(benzimidazolyl-2 radicals-yl) alkane represents by formula 1, wherein, n=8.
Described O ', O '-Diphenyl disulfide is for phosphoric acid-N, and TMSDEA N diethylamine is represented by formula 2.
Wherein, described O ', O '-Diphenyl disulfide is for phosphoric acid-N, and the preparation method of TMSDEA N diethylamine is specially:
By 22.2g phosphorus pentasulfide (0.1mol), 37.6g phenol (0.4mol) joins in 250mL there-necked flask, adds 70mL toluene to make solvent; Gradually temperature is elevated to while stirring to about 100 ℃ reaction 45min; Heat up again until reflux, backflow 3h, in course of reaction, solid fades away; Solution is slightly cold, adds a small amount of activated charcoal boiling decoloring, filters while hot, and filtrate is cooled to room temperature; Gained filtrate is transferred in beaker, and water-bath is cooling and under agitation dropwise drip 22mL diethylamine (0.2mol), and reaction system is emitted a large amount of heat, liquid color gradually becomes Chinese red, use glass bar rapid stirring, have precipitation to produce, one night of static placement under room temperature; Filtration under diminished pressure, by toluene wash, to white, product is white needle-like crystals; Toluene recrystallization, filtration under diminished pressure, vacuum drying, obtains white crystal, obtains.
Wherein, described ω, the preparation method of ω '-bis-(benzimidazolyl-2 radicals-yl) alkane is specially:
Take respectively 0.11mol o-phenylenediamine and 0.05mol fat diacid, in mortar, fully grind it is mixed, be transferred in three-neck flask.Add nitration mixture, logical nitrogen, heating reflux reaction under mechanical raking.TLC tracking and monitoring finishes to reaction, and about 10h, pours in 250mL beaker, standing cooling, with strong aqua, regulates pH=7.Standing over night at 4 ℃, suction filtration is dry, and gained crude product methanol/water recrystallization, obtains sterling.
Below adopt embodiment to describe embodiments of the present invention in detail, to the present invention, how application technology means solve technical matters whereby, and the implementation procedure of reaching technique effect can fully understand and implement according to this.
Embodiment 1
Embodiment 1O ', O '-Diphenyl disulfide is for phosphoric acid-N, the preparation of TMSDEA N diethylamine
By 22.2g phosphorus pentasulfide (0.1mol), 37.6g phenol (0.4mol) joins in 250mL there-necked flask, adds 70mL toluene to make solvent; Gradually temperature is elevated to while stirring to about 100 ℃ reaction 45min; Heat up again until reflux, backflow 3h, in course of reaction, solid fades away; Solution is slightly cold, adds a small amount of activated charcoal boiling decoloring, filters while hot, and filtrate is cooled to room temperature; Gained filtrate is transferred in beaker, and water-bath is cooling and under agitation dropwise drip 22mL diethylamine (0.2mol), and reaction system is emitted a large amount of heat, liquid color gradually becomes Chinese red, use glass bar rapid stirring, have precipitation to produce, one night of static placement under room temperature; Filtration under diminished pressure, by toluene wash, to white, product is white needle-like crystals; Toluene recrystallization, filtration under diminished pressure, vacuum drying, obtains white crystal, obtains.
Embodiment 2 ω, the preparation of ω '-bis-(benzimidazolyl-2 radicals-yl) alkane
Take respectively 0.11mol o-phenylenediamine and 0.05mol fat diacid, in mortar, fully grind it is mixed, be transferred in three-neck flask.Add nitration mixture, logical nitrogen, heating reflux reaction under mechanical raking.TLC tracking and monitoring finishes to reaction, and about 10h, pours in 250mL beaker, standing cooling, with strong aqua, regulates pH=7.Standing over night at 4 ℃, suction filtration is dry, and gained crude product methanol/water recrystallization, obtains sterling.
Embodiment 3 cleaning fluids 1
By the O ' of N-ethyl carbamic acid ethyl ester 25g, ethylene glycol monobutyl ether 8g, gallic acid 4g, organic solvent dimethyl sulfoxide (DMSO) 90g and embodiment 1 preparation, O '-Diphenyl disulfide is for phosphoric acid-N, the ω of TMSDEA N diethylamine 4g, embodiment 2 preparations, ω '-bis-(benzimidazolyl-2 radicals-yl) alkane 4g mixes to clarification, obtains cleaning fluid 1.
Comparative example 1 cleaning fluid 2
By the O ' of N-ethyl carbamic acid ethyl ester 25g, ethylene glycol monobutyl ether 8g, gallic acid 4g, organic solvent dimethyl sulfoxide (DMSO) 90g and embodiment 1 preparation, O '-Diphenyl disulfide is for phosphoric acid-N, and TMSDEA N diethylamine 8g mixes to clarification, obtains cleaning fluid 2.
Comparative example 2 cleaning fluids 3
By the ω of N-ethyl carbamic acid ethyl ester 25g, ethylene glycol monobutyl ether 8g, gallic acid 4g, organic solvent dimethyl sulfoxide (DMSO) 90g and embodiment 2 preparations, ω '-bis-(benzimidazolyl-2 radicals-yl) alkane 8g mixes to clarification, obtains cleaning fluid 3.
Comparative example 3 cleaning fluids 4
N-ethyl carbamic acid ethyl ester 25g, ethylene glycol monobutyl ether 8g, gallic acid 4g, organic solvent dimethyl sulfoxide (DMSO) 90g are mixed to clarification, obtain cleaning fluid 4.
Effect test
For evaluating the test piece to corrosion of metal ability, preparation with the following methods.That is, glass surface with
the aluminium of left and right thickness (aluminum), molybdenum (molybdenum), copper (copper) form after film (film formation), and coating etchant resist also completes development (develop) and makes test piece 1.
The second, for evaluating the test piece of etchant resist stripping performance, preparation with the following methods.; at glass surface, by chromium (Cr), formed after film; coating etchant resist; and carry out providing dry etching gas (dry etching gas) after wet etching (wet etching); thereby test piece 2 in addition to make n+a-Si:H activation film (active film); for forming the etchant resist through the serious modification of dry method etch technology, again carry out dry etching (etching) operation, thereby make test piece 3.In chromium (chromium) layer, the adhesion of etchant resist becomes large, if and be subject to dry etching gas (dry etching gas), can cause the modification of etchant resist and be difficult to peel off with remover, therefore described test piece is suitable for testing etchant resist stripping performance.
Extent of corrosion: ◎ (not corrosion completely); Zero (slightly corrosion); △ (seriously corroded); X (corrosion completely).
Evaluate the stripping performance of etchant resist: ◎ (etchant resist is removed completely); Zero (the slightly residue of etchant resist); △ (residue of etchant resist is serious); X (can not remove etchant resist completely).
Use test piece 2,3 pairs of single raw-material etchant resist stripping performances of test piece to evaluate; And use the corrosive power of test piece 1 pair of aluminium, molybdenum and copper to evaluate, its result is illustrated in table 1.
Table 1
All above-mentioned these intellecture properties of primary enforcement, do not set restriction this new product of other forms of enforcement and/or new method.Those skilled in the art will utilize this important information, and foregoing is revised, to realize similar implementation status.But all modifications or transformation belong to the right of reservation based on new product of the present invention.
The above, be only preferred embodiment of the present invention, is not the present invention to be done to the restriction of other form, and any those skilled in the art may utilize the technology contents of above-mentioned announcement to be changed or be modified as the equivalent embodiment of equivalent variations.But every technical solution of the present invention content that do not depart from, any simple modification, equivalent variations and the remodeling above embodiment done according to technical spirit of the present invention, still belong to the protection domain of technical solution of the present invention.
Claims (9)
1. a novel light-sensitive surface cleaning fluid, is characterized in that: comprise pentaerythrite, potassium hydroxide, organic amine, anticorrosive and solvent.
2. light-sensitive surface cleaning fluid as claimed in claim 1, it is characterized in that: the mass percent of pentaerythrite is 0.1-15%, the mass percent of potassium hydroxide is 0.1-10%, the mass percent of organic amine is 0.5-30%, anticorrosive 0.5-5%, solvent is She's amount, and each constituent mass number percent sum is 100%.
3. light-sensitive surface cleaning fluid as claimed in claim 1 or 2, is characterized in that: the mass percent of pentaerythrite is 10%, and the mass percent of potassium hydroxide is 8%, and the mass percent of organic amine is 25%, anticorrosive 3%, and solvent is 54%.
4. the light-sensitive surface cleaning fluid as described in claims 1 to 3, is characterized in that: described machine amine for be selected from comprise monoethanolamine, isopropanolamine, amino ethoxy ethanol, n-methylethanolamine, dimethylethanolamine, diethyl ethanolamine, 2-aminoethyl ethylaminoethanol, at least one compound of group of aminoethyl piperazine, aminopropyl piperazine, 1-(2-hydroxyethyl) piperazine, 1-amino-4-methyl piperazine, 2-methyl piperazine, 1-methyl piperazine, 1-benzyl diethylenediamine, 2-phenylpiperazine, 1-aminoethyl piperidine, 1-amino piperidine and 1-aminomethyl piperidines.
5. the light-sensitive surface cleaning fluid as described in claim 1 to 4, is characterized in that: described solvent is one or more in sulfoxide, sulfone, imidazolidinone, imidazolone, alcohol, ether, acid amides.
6. the light-sensitive surface cleaning fluid as described in claim 1 to 5, is characterized in that: described sulfoxide is dimethyl sulfoxide (DMSO); Described sulfone is sulfolane; Described imidazolidinone is 1,3-dimethyl-2-imidazolidinone; Described imidazolone is DMI; Described acid amides is dimethyl formamide, dimethyl acetamide; Described alcohol is propylene glycol, diethylene glycol; Ether is glycol ether or propylene glycol.
7. the etchant resist remover as described in claim 1 to 6, it is characterized in that: described anticorrosive is by the O ' shown in formula 2, O '-Diphenyl disulfide is for phosphoric acid-N, ω shown in TMSDEA N diethylamine and formula 1, ω '-bis-(benzimidazolyl-2 radicals-yl) alkane forms, wherein, n=8, both quality are 1:1～1:2.
8. the etchant resist remover as described in claim 1 to 7, is characterized in that: described O ', and O '-Diphenyl disulfide is for phosphoric acid-N, and the preparation method of TMSDEA N diethylamine is specially:
By 22.2g phosphorus pentasulfide (0.1mol), 37.6g phenol (0.4mol) joins in 250mL there-necked flask, adds 70mL toluene to make solvent; Gradually temperature is elevated to while stirring to about 100 ℃ reaction 45min; Heat up again until reflux, backflow 3h, in course of reaction, solid fades away; Solution is slightly cold, adds a small amount of activated charcoal boiling decoloring, filters while hot, and filtrate is cooled to room temperature; Gained filtrate is transferred in beaker, and water-bath is cooling and under agitation dropwise drip 22mL diethylamine (0.2mol), and reaction system is emitted a large amount of heat, liquid color gradually becomes Chinese red, use glass bar rapid stirring, have precipitation to produce, one night of static placement under room temperature; Filtration under diminished pressure, by toluene wash, to white, product is white needle-like crystals; Toluene recrystallization, filtration under diminished pressure, vacuum drying, obtains white crystal, obtains.
9. the etchant resist remover as described in claim 1 to 8, is characterized in that: described ω, and the preparation method of ω '-bis-(benzimidazolyl-2 radicals-yl) alkane is specially:
Take respectively 0.11mol o-phenylenediamine and 0.05mol fat diacid, in mortar, fully grind it is mixed, be transferred in three-neck flask.Add nitration mixture, logical nitrogen, heating reflux reaction under mechanical raking.TLC tracking and monitoring finishes to reaction, and about 10h, pours in 250mL beaker, standing cooling, with strong aqua, regulates pH=7.Standing over night at 4 ℃, suction filtration is dry, and gained crude product methanol/water recrystallization, obtains sterling.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201310511175.4A CN103605268A (en) | 2013-10-25 | 2013-10-25 | Cleaning liquid used during semiconductor manufacturing process |
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| CN201310511175.4A CN103605268A (en) | 2013-10-25 | 2013-10-25 | Cleaning liquid used during semiconductor manufacturing process |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103616806A (en) * | 2013-10-25 | 2014-03-05 | 青岛华仁技术孵化器有限公司 | Cleaning fluid for photosensitive membrane |
| CN103616805A (en) * | 2013-10-25 | 2014-03-05 | 青岛华仁技术孵化器有限公司 | Cleaning fluid used in semiconductor manufacture process |
| CN104049477A (en) * | 2014-05-30 | 2014-09-17 | 青岛华仁技术孵化器有限公司 | Resist remover |
| CN106337196A (en) * | 2016-07-31 | 2017-01-18 | 深圳市贝加电子材料有限公司 | Micro pore sealing agent for noble metal surface treatment of printed circuit board |
-
2013
- 2013-10-25 CN CN201310511175.4A patent/CN103605268A/en active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103616806A (en) * | 2013-10-25 | 2014-03-05 | 青岛华仁技术孵化器有限公司 | Cleaning fluid for photosensitive membrane |
| CN103616805A (en) * | 2013-10-25 | 2014-03-05 | 青岛华仁技术孵化器有限公司 | Cleaning fluid used in semiconductor manufacture process |
| CN103616806B (en) * | 2013-10-25 | 2017-02-08 | 马佳 | Cleaning fluid for photosensitive membrane |
| CN104049477A (en) * | 2014-05-30 | 2014-09-17 | 青岛华仁技术孵化器有限公司 | Resist remover |
| CN104049477B (en) * | 2014-05-30 | 2017-12-19 | 江苏弘汉生物科技有限公司 | Corrosion inhibitor stripper |
| CN106337196A (en) * | 2016-07-31 | 2017-01-18 | 深圳市贝加电子材料有限公司 | Micro pore sealing agent for noble metal surface treatment of printed circuit board |
| CN106337196B (en) * | 2016-07-31 | 2018-08-10 | 深圳市贝加电子材料有限公司 | Microscopic void sealer for the processing of printed wiring board precious metal surface |
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