CN103543619A - Anticorrosive agent composition comprising imidazoline - Google Patents
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- CN103543619A CN103543619A CN201310456533.6A CN201310456533A CN103543619A CN 103543619 A CN103543619 A CN 103543619A CN 201310456533 A CN201310456533 A CN 201310456533A CN 103543619 A CN103543619 A CN 103543619A
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Abstract
The invention provides an anticorrosive agent composition for anticorrosive film peeling, which is characterized by comprising chlorinated 1-hydroxyethyl-3-hexadecyl imidazole and 1-(2-amino-thioureidoethyl)-2-oleyl imidazoline. When being used for peeling the anticorrosive film for a layout electronic circuit or display element metal wire, the anticorrosive film peeling agent does not corrode the metal, especially aluminum, molybdenum, copper, titanium and other metals, and has the advantage of excellent anticorrosive film peeling property.
Description
Technical field
The present invention relates to remove the remover combination of etchant resist used (resist) in photolithography method (photo-lithography), relate in particular to a kind of when the etchant resist of removing for Butut metal line, the corrosion to metal line can be reduced, and the outstanding etchant resist remover combination of peeling off effect can be reached.
Background technology
Conventionally, etchant resist (photoresist, photo-resist) be requisite material in photolithography process, and photolithography process is generally applied to integrated circuit (integrated circuit, IC), large scale integrated circuit (large scale integration, LSI), the manufacture of the image display device such as the semiconductor device such as VLSI (very large scale integrated circuit) (very large scale integration, VLSI) and liquid crystal display, flat-panel monitor
Yet, carrying out photolithography technique (photo-lithography processing) afterwards, etchant resist is at high temperature stripped from solution removal, but in this process, exists lower metal film may be stripped from too quickly the problem of solution corrosion.
That is,, due to described etchant resist stripping solution, there is the problem of the extent of corrosion quickening of metal line.In order to address the above problem, United States Patent (USP) the 5th, 417, No. 877, United States Patent (USP) the 5th, in 556, No. 482 and Jap.P. JP1999-375267 (No. 2001-188363rd, Japanese Patent Publication), disclose for preventing the preparation method of the etchant resist stripping solution of metal line corrosion.
Described method is to add corrosion inhibitor in the potpourri of acid amides (amide) and organic amine (organic amine), described potpourri is prevented to corrosion of metal in metal line as etchant resist stripping solution, and the method has pointed out that organic amine is preferably used monoethanolamine (monoethanolamine).In addition, pointed out the suitable consumption of corrosion inhibitor, and if while surpassing suitable consumption, the peeling off effect and will reduce of described photoresist film.
In addition, the amine in conventional etchant resist stripping solution is mainly used one-level or the secondary amines such as monoethanol (monoethanolamine), methylethanolamine (methylethanolamine).
Yet described one-level or secondary amine have and form the labile shortcoming of partial volume because boiling point is low, and through weight and composition, because changing, have therefore brought the inconvenience that needs to change whole stripping solutions in technological process after a period of time.In addition, when described one-level or secondary amine do not comprise corrosion inhibitor, even if sneak into a small amount of water, also can make metal line heavy corrosion.
Summary of the invention
The object of the invention is in order to overcome the deficiencies in the prior art, a kind of process peeling off for the etchant resist of Butut electronic circuit or display element metal line is provided, do not corrode metal line, particularly do not corrode the metals such as aluminium (aluminum), molybdenum (molybdenum), copper (copper), titanium (titanium), and there is the etchant resist remover combination of outstanding etchant resist fissility.
For solving the problems of the technologies described above, the invention provides a kind of anticorrosive composition of peeling off for etchant resist, it comprises chlorination 1-hydroxyethyl-3-cetyl imidazoles and 1-(2-amino-thiourea ethyl)-2-oleic acid base imidazoline.
Wherein, the mass ratio of described chlorination 1-hydroxyethyl-3-cetyl imidazoles and 1-(2-amino-thiourea ethyl)-2-oleic acid base imidazoline is 2:1～1:2.
Wherein, the preparation method of described chlorination 1-hydroxyethyl-3-cetyl imidazoles is specially:
The first step, the preparation of 1-cetyl imidazoles mixes the bromohexadecane of 1.79 imidazoles and 3.8mL in the ethyl acetate of 35mL, and magnetic agitation mixes for 10 minutes.Potpourri is poured in the polytetrafluoroethyllining lining that capacity is 60mL, polytetrafluoroethyllining lining is encapsulated in stainless steel cauldron, and put into digital baking oven, from room temperature is heated to 120 ℃ of isothermal reaction 16h, naturally cool to room temperature.Then potpourri is filtered to taking-up filtrate, with distilled water washing, for several times to remove the imidazoles of not participating in reaction, with Rotary Evaporators, solvent ethyl acetate is steamed, products therefrom 1-cetyl imidazoles is dried 12 hours to constant weight in 70 ℃ of vacuum drying chambers.Obtain weak yellow liquid, weigh product;
Second step, the ethylene chlorhydrin of the 1-cetyl imidazoles of 2.9g and 1ml is mixed in the ethyl acetate of 35ml, and magnetic agitation mixes for 10 minutes, wherein, reactant ethylene chlorhydrin is excessive, 1-cetyl imidazoles is fully reacted, potpourri is poured in the polytetrafluoroethyllining lining that capacity is 60mL, polytetrafluoroethyllining lining is encapsulated in stainless steel cauldron, and put into digital baking oven, from room temperature, be heated to 120 ℃, isothermal reaction 6h, naturally cools to room temperature.With Rotary Evaporators, solvent and excessive reactant ethylene chlorhydrin are steamed, within dry 12 hours in 70 ℃ of vacuum drying chambers, to constant weight, the chlorination 1-hydroxyethyl-3-cetyl imidazoles obtaining is white solid to products therefrom.
Wherein, the preparation method of described 1-(2-amino-thiourea ethyl)-2-oleic acid base imidazoline is specially:
The oleic acid of 0.2mol is evenly mixed with the diethylenetriamine of 0.24mol, and to add massfraction be that 25%～35% dimethylbenzene is as azeotropic agent, continue to be subsequently uniformly mixed liquid, simultaneously constant-speed heating carries out dehydration of amide to 415K～435K, after reaction 2.5h, obtain acid amides, on this basis, continue to be warming up to 495～515K and carry out cyclodehydration, after reaction 2h, be cooled to 395K, utilize vacuum pump under reduced pressure, to distill 0.5h to remove removal xylene and the complete diethylenetriamine of unreacted, finally adopt isopropyl alcohol to carry out recrystallization to crude product and obtain 1-(2-aminoethyl)-2-oleic acid base imidazoline,
Second step adds 0.2mol thiosemicarbazide and 30ml n-octyl alcohol to carry out vulcanizing treatment in synthetic 1-(2-aminoethyl)-2-oleic acid base imidazoline.First mixed liquor is continued to stir and be heated to the condensation reaction that 415K～435K carries out 3.5h, then utilize vacuum pump to carry out decompression distillation 0.5h at 405KK, obtain 1-(2-amino-thiourea ethyl)-2-oleic acid base imidazoline.
The present invention also provides the application of above-mentioned anticorrosive composition in etchant resist stripping process.
Beneficial effect of the present invention:
Etchant resist remover provided by the invention does not corrode metal line while peeling off etchant resist, particularly do not corrode the metals such as aluminium (aluminum), molybdenum (molybdenum), copper (copper), titanium (titanium), and there is outstanding etchant resist fissility.
Embodiment
An etchant resist remover, it comprises N-ethyl carbamic acid ethyl ester, ethylene glycol monobutyl ether, gallic acid, organic solvent and anticorrosive.
Described organic solvent is 1-METHYLPYRROLIDONE, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide (DMSO), dimethyl acetamide, dimethyl formamide, N-METHYLFORMAMIDE, sulfolane, butyl diethylene glycol, ethyl diethylene glycol, methyl diethylene glycol, triethylene glycol, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, and composition thereof.
In described etchant resist remover, the weight portion of each component is respectively N-ethyl carbamic acid ethyl ester 20 weight portion～30 weight portions, ethylene glycol monobutyl ether 5 weight portion～10 weight portions, gallic acid 3～5 weight portions, organic solvent 60～70 weight portions and anticorrosive 5～10 weight portions.
Further preferably, in described etchant resist remover, the weight portion of each component is respectively N-ethyl carbamic acid ethyl ester 25 weight portions, ethylene glycol monobutyl ether 8 weight portions, gallic acid 4 weight portions, organic solvent 65 weight portions and anticorrosive 8 weight portions.
Described anticorrosive consists of chlorination 1-hydroxyethyl-3-cetyl imidazoles and 1-(2-amino-thiourea ethyl)-2-oleic acid base imidazoline.
Wherein, the preparation method of described chlorination 1-hydroxyethyl-3-cetyl imidazoles is specially:
The first step, the preparation of 1-cetyl imidazoles mixes the bromohexadecane of 1.79 imidazoles and 3.8mL in the ethyl acetate of 35mL, and magnetic agitation mixes for 10 minutes.Potpourri is poured in the polytetrafluoroethyllining lining that capacity is 60mL, polytetrafluoroethyllining lining is encapsulated in stainless steel cauldron, and put into digital baking oven, from room temperature is heated to 120 ℃ of isothermal reaction 16h, naturally cool to room temperature.Then potpourri is filtered to taking-up filtrate, with distilled water washing, for several times to remove the imidazoles of not participating in reaction, with Rotary Evaporators, solvent ethyl acetate is steamed, products therefrom 1-cetyl imidazoles is dried 12 hours to constant weight in 70 ℃ of vacuum drying chambers.Obtain weak yellow liquid, weigh product;
Second step, the ethylene chlorhydrin of the 1-cetyl imidazoles of 2.9g and 1ml is mixed in the ethyl acetate of 35ml, and magnetic agitation mixes for 10 minutes, wherein, reactant ethylene chlorhydrin is excessive, 1-cetyl imidazoles is fully reacted, potpourri is poured in the polytetrafluoroethyllining lining that capacity is 60mL, polytetrafluoroethyllining lining is encapsulated in stainless steel cauldron, and put into digital baking oven, from room temperature, be heated to 120 ℃, isothermal reaction 6h, naturally cools to room temperature.With Rotary Evaporators, solvent and excessive reactant ethylene chlorhydrin are steamed, within dry 12 hours in 70 ℃ of vacuum drying chambers, to constant weight, the chlorination 1-hydroxyethyl-3-cetyl imidazoles obtaining is white solid to products therefrom.
The preparation method of described 1-(2-amino-thiourea ethyl)-2-oleic acid base imidazoline is specially:
The first step, the oleic acid of 0.2mol is evenly mixed with the diethylenetriamine of 0.24mol, and to add massfraction be that 25%～35% dimethylbenzene is as azeotropic agent, continue to be subsequently uniformly mixed liquid, simultaneously constant-speed heating carries out dehydration of amide to 415K～435K, after reaction 2.5h, obtain acid amides, reaction equation is suc as formula (1).On this basis, continue to be warming up to 495～515K and carry out cyclodehydration, after reaction 2h, be cooled to 395K, utilize vacuum pump under reduced pressure, to distill 0.5h to remove removal xylene and the complete diethylenetriamine of unreacted, finally adopt isopropyl alcohol to carry out recrystallization to crude product and obtain 1-(2-aminoethyl)-2-oleic acid base imidazoline, shown in (2);
Second step adds 0.2mol thiosemicarbazide and 30ml n-octyl alcohol to carry out vulcanizing treatment in synthetic 1-(2-aminoethyl)-2-oleic acid base imidazoline.First mixed liquor is continued to stir and be heated to the condensation reaction that 415K～435K carries out 3.5h, then utilize vacuum pump to carry out decompression distillation 0.5h at 405KK, obtain 1-(2-amino-thiourea ethyl)-2-oleic acid base imidazoline, shown in (3).
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.
The preparation of embodiment 1 chlorination 1-hydroxyethyl-3-cetyl imidazoles
The bromohexadecane of 1.79 imidazoles and 3.8mL (amount of substance is than being 2:1) is mixed in the ethyl acetate of 35mL, and magnetic agitation mixes for 10 minutes.Potpourri is poured in the polytetrafluoroethyllining lining that capacity is 60mL, polytetrafluoroethyllining lining is encapsulated in stainless steel cauldron, and put into digital baking oven, from room temperature is heated to 120 ℃ of isothermal reaction 16h, naturally cool to room temperature.Then potpourri is filtered to taking-up filtrate, with distilled water washing, for several times to remove the imidazoles of not participating in reaction, with Rotary Evaporators, solvent ethyl acetate is steamed, products therefrom 1-cetyl imidazoles is dried 12 hours to constant weight in 70 ℃ of vacuum drying chambers.Obtain weak yellow liquid, weigh product, the ethylene chlorhydrin of the 1-cetyl imidazoles of 2.9g and 1ml (amount of substance is than being 1:1.2) is mixed in the ethyl acetate of 35ml, magnetic agitation mixes for 10 minutes, wherein, reactant ethylene chlorhydrin is excessive, 1-cetyl imidazoles is fully reacted, potpourri is poured in the polytetrafluoroethyllining lining that capacity is 60mL, polytetrafluoroethyllining lining is encapsulated in stainless steel cauldron, and puts into digital baking oven, from room temperature, be heated to 120 ℃, isothermal reaction 6h, naturally cools to room temperature.With Rotary Evaporators, solvent and excessive reactant ethylene chlorhydrin are steamed, within dry 12 hours in 70 ℃ of vacuum drying chambers, to constant weight, the chlorination 1-hydroxyethyl-3-cetyl imidazoles obtaining is white solid to products therefrom.
The preparation of embodiment 21-(2-amino-thiourea ethyl)-2-oleic acid base imidazoline
By the oleic acid of 0.2mol (Tianjin Bo Di Chemical Co., Ltd., analyze pure) with diethylenetriamine (the Tianjin Bo Di Chemical Co., Ltd. of 0.24mol, analyze pure) evenly mix, and to add massfraction be 25%～35% dimethylbenzene (Laiyang City Kant Chemical Co., Ltd., analyze pure) as azeotropic agent, continue to be subsequently uniformly mixed liquid, constant-speed heating carries out dehydration of amide to 415K～435K simultaneously, after reaction 2.5h, obtains acid amides.On this basis, continue to be warming up to 495～515K and carry out cyclodehydration, after reaction 2h, be cooled to 395K, utilize vacuum pump under reduced pressure, to distill 0.5h to remove removal xylene and the complete diethylenetriamine of unreacted, finally adopt isopropyl alcohol (economic and technological development zone, Laiyang Fine Chemical Works, analyze pure) crude product is carried out to recrystallization obtain 1-(2-aminoethyl)-2-oleic acid base imidazoline, in synthetic 1-(2-aminoethyl)-2-oleic acid base imidazoline, add 0.2mol thiosemicarbazide (Tianjin chemical reagent company limited, analyze pure) and 30ml n-octyl alcohol (Tianjin chemical reagent company limited, analyze pure) carry out vulcanizing treatment.First mixed liquor is continued to stir and be heated to the condensation reaction that 415K～435K carries out 3.5h, then utilize vacuum pump to carry out decompression distillation 0.5h at 405K K, obtain 1-(2-amino-thiourea ethyl)-2-oleic acid base imidazoline.
Embodiment 3
1-(2-amino-thiourea ethyl)-2-oleic acid base imidazoline 4g of chlorination 1-hydroxyethyl-3-cetyl imidazoles 4g of N-ethyl carbamic acid ethyl ester 25g, ethylene glycol monobutyl ether 8g, gallic acid 4g, organic solvent and embodiment 1 preparation, embodiment 2 preparations is mixed to clarification, obtain remover.
Effect test
For evaluating the test piece to corrosion of metal ability, preparation with the following methods.That is, at glass surface with 2000
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.
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 (6)
1. an anticorrosive composition of peeling off for etchant resist, is characterized in that: comprise chlorination 1-hydroxyethyl-3-cetyl imidazoles and 1-(2-amino-thiourea ethyl)-2-oleic acid base imidazoline.
2. the anticorrosive composition of peeling off for etchant resist as claimed in claim 1, is characterized in that: the mass ratio of described chlorination 1-hydroxyethyl-3-cetyl imidazoles and 1-(2-amino-thiourea ethyl)-2-oleic acid base imidazoline is 2:1～1:2.
3. the anticorrosive composition of peeling off for etchant resist as claimed in claim 1 or 2, is characterized in that: the preparation method of described chlorination 1-hydroxyethyl-3-cetyl imidazoles is specially:
The first step, the preparation of 1-cetyl imidazoles mixes the bromohexadecane of 1.79 imidazoles and 3.8mL in the ethyl acetate of 35mL, and magnetic agitation mixes for 10 minutes.Potpourri is poured in the polytetrafluoroethyllining lining that capacity is 60mL, polytetrafluoroethyllining lining is encapsulated in stainless steel cauldron, and put into digital baking oven, from room temperature is heated to 120 ℃ of isothermal reaction 16h, naturally cool to room temperature.Then potpourri is filtered to taking-up filtrate, with distilled water washing, for several times to remove the imidazoles of not participating in reaction, with Rotary Evaporators, solvent ethyl acetate is steamed, products therefrom 1-cetyl imidazoles is dried 12 hours to constant weight in 70 ℃ of vacuum drying chambers.Obtain weak yellow liquid, weigh product;
Second step, the ethylene chlorhydrin of the 1-cetyl imidazoles of 2.9g and 1ml is mixed in the ethyl acetate of 35ml, and magnetic agitation mixes for 10 minutes, wherein, reactant ethylene chlorhydrin is excessive, 1-cetyl imidazoles is fully reacted, potpourri is poured in the polytetrafluoroethyllining lining that capacity is 60mL, polytetrafluoroethyllining lining is encapsulated in stainless steel cauldron, and put into digital baking oven, from room temperature, be heated to 120 ℃, isothermal reaction 6h, naturally cools to room temperature.With Rotary Evaporators, solvent and excessive reactant ethylene chlorhydrin are steamed, within dry 12 hours in 70 ℃ of vacuum drying chambers, to constant weight, the chlorination 1-hydroxyethyl-3-cetyl imidazoles obtaining is white solid to products therefrom.
4. the anticorrosive composition of peeling off for etchant resist as described in claims 1 to 3, is characterized in that: the preparation method of described 1-(2-amino-thiourea ethyl)-2-oleic acid base imidazoline is specially:
The oleic acid of 0.2mol is evenly mixed with the diethylenetriamine of 0.24mol, and to add massfraction be that 25%～35% dimethylbenzene is as azeotropic agent, continue to be subsequently uniformly mixed liquid, simultaneously constant-speed heating carries out dehydration of amide to 415K～435K, after reaction 2.5h, obtain acid amides, on this basis, continue to be warming up to 495～515K and carry out cyclodehydration, after reaction 2h, be cooled to 395K, utilize vacuum pump under reduced pressure, to distill 0.5h to remove removal xylene and the complete diethylenetriamine of unreacted, finally adopt isopropyl alcohol to carry out recrystallization to crude product and obtain 1-(2-aminoethyl)-2-oleic acid base imidazoline,
Second step adds 0.2mol thiosemicarbazide and 30ml n-octyl alcohol to carry out vulcanizing treatment in synthetic 1-(2-aminoethyl)-2-oleic acid base imidazoline.First mixed liquor is continued to stir and be heated to the condensation reaction that 415K～435K carries out 3.5h, then utilize vacuum pump to carry out decompression distillation 0.5h at 405KK, obtain 1-(2-amino-thiourea ethyl)-2-oleic acid base imidazoline.
5. the preparation method of the anticorrosive composition of peeling off for etchant resist as described in claim 1 to 5, is characterized in that: described two kinds of components are mixed and be get final product.
6. the application of anticorrosive composition in etchant resist stripping process described in claim 1 to 5.
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Application publication date: 20140129 |