CN113563983A - Cleaning liquid for semiconductor integrated circuit and production process thereof - Google Patents
Cleaning liquid for semiconductor integrated circuit and production process thereof Download PDFInfo
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- CN113563983A CN113563983A CN202110664820.0A CN202110664820A CN113563983A CN 113563983 A CN113563983 A CN 113563983A CN 202110664820 A CN202110664820 A CN 202110664820A CN 113563983 A CN113563983 A CN 113563983A
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- 239000004065 semiconductor Substances 0.000 title claims abstract description 38
- 238000004140 cleaning Methods 0.000 title claims abstract description 35
- 239000007788 liquid Substances 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title abstract description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 35
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000003607 modifier Substances 0.000 claims abstract description 24
- 239000003463 adsorbent Substances 0.000 claims abstract description 22
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims abstract description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 22
- 238000002156 mixing Methods 0.000 claims abstract description 21
- FEKZISUDCVHILF-UHFFFAOYSA-N 2-(dodecylamino)ethane-1,1-diol Chemical compound CCCCCCCCCCCCNCC(O)O FEKZISUDCVHILF-UHFFFAOYSA-N 0.000 claims abstract description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229960000892 attapulgite Drugs 0.000 claims abstract description 12
- 229910052625 palygorskite Inorganic materials 0.000 claims abstract description 12
- 239000002994 raw material Substances 0.000 claims abstract description 7
- 238000003756 stirring Methods 0.000 claims description 71
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 38
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 20
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 19
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 239000008367 deionised water Substances 0.000 claims description 12
- 229910021641 deionized water Inorganic materials 0.000 claims description 12
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 claims description 8
- 229940010698 activated attapulgite Drugs 0.000 claims description 8
- -1 binaphthyl diphenyl phosphate Chemical compound 0.000 claims description 8
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 claims description 8
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 7
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 7
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 7
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 7
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 7
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 claims description 7
- 238000005286 illumination Methods 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 4
- 230000003213 activating effect Effects 0.000 claims description 3
- 230000004913 activation Effects 0.000 claims description 3
- 230000018044 dehydration Effects 0.000 claims description 3
- 238000006297 dehydration reaction Methods 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 238000000227 grinding Methods 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 238000007873 sieving Methods 0.000 claims description 3
- 239000002689 soil Substances 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract description 5
- 238000001179 sorption measurement Methods 0.000 abstract description 4
- 244000005700 microbiome Species 0.000 abstract description 3
- 235000017168 chlorine Nutrition 0.000 description 9
- 230000009471 action Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000004075 alteration Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 125000001309 chloro group Chemical class Cl* 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
- B01J20/10—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising silica or silicate
- B01J20/12—Naturally occurring clays or bleaching earth
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/42—One nitrogen atom
- C07D251/46—One nitrogen atom with oxygen or sulfur atoms attached to the two other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2003—Alcohols; Phenols
- C11D3/2006—Monohydric alcohols
- C11D3/201—Monohydric alcohols linear
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2003—Alcohols; Phenols
- C11D3/2006—Monohydric alcohols
- C11D3/2017—Monohydric alcohols branched
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2003—Alcohols; Phenols
- C11D3/2041—Dihydric alcohols
- C11D3/2044—Dihydric alcohols linear
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/24—Organic compounds containing halogen
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Dispersion Chemistry (AREA)
- Geochemistry & Mineralogy (AREA)
- Inorganic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a cleaning solution for a semiconductor integrated circuit and a production process thereof, belonging to the technical field of cleaning solutions for integrated circuits. The cleaning solution for the semiconductor integrated circuit comprises the following raw materials in parts by weight: 30-50 parts of absolute ethyl alcohol, 10-20 parts of isopropanol, 5-15 parts of N, N-bis-hydroxyethyl dodecyl amide, 5.2-6.2 parts of dichloromethane, 4.5-6.5 parts of 1, 4-butanediol and 4.3-6.5 parts of adsorbent; the cleaning solution for the semiconductor integrated circuit is prepared by the steps of preparing solution A, preparing solution B, mixing and the like, wherein an adsorbent is prepared, attapulgite is used as a raw material, a modifier with quaternary ammonium salt is combined with the attapulgite, the modified attapulgite has oleophylic groups and quaternary ammonium salt groups, microorganisms and oil stains can be taken away, and the cleaning solution prepared by the adsorbent has excellent adsorption capacity.
Description
Technical Field
The invention relates to the technical field of integrated circuit cleaning liquid, in particular to a cleaning liquid for a semiconductor integrated circuit and a production process thereof.
Background
The semiconductor integrated circuit is a semiconductor integrated circuit device having at least one circuit block on a semiconductor substrate, and the semiconductor integrated circuit is formed by interconnecting active elements such as transistors and diodes and passive elements such as resistors and capacitors on a semiconductor single chip according to a predetermined circuit, thereby performing a specific circuit or system function.
Semiconductor integrated circuits are currently used in various fields, such as the computer industry, industrial control, machinery, electronics, aviation, and many others. Because of its high precision and high performance, the integrated circuit will accumulate a plurality of impurity dusts during long-term use, and it needs to be cleaned strictly, otherwise it will have serious influence on its performance, and it can not reach the use requirement, so it is necessary to prepare a cleaning solution for semiconductor integrated circuit.
Disclosure of Invention
Technical problem to be solved
The invention provides a cleaning solution for a semiconductor integrated circuit and a production process thereof, which are used for solving the problems of the background art.
(II) technical scheme
In order to achieve the purpose, the invention is realized by the following technical scheme: a cleaning solution for a semiconductor integrated circuit comprises the following raw materials in parts by weight: 30-50 parts of absolute ethyl alcohol, 10-20 parts of isopropanol, 5-15 parts of N, N-bis-hydroxyethyl dodecyl amide, 5.2-6.2 parts of dichloromethane, 4.5-6.5 parts of 1, 4-butanediol and 4.3-6.5 parts of adsorbent;
the adsorbent is prepared by the following steps:
placing attapulgite raw soil at 100 ℃ for dehydration and activation for 4h to obtain activated attapulgite, then adding the activated attapulgite, a modifier and deionized water into a flask, reacting at a constant temperature of 50 ℃ and at a rotation speed of 300r/min for 5h, filtering and washing after the reaction is finished, drying at 80 ℃ for 12h, activating at 110 ℃ for 1h, and grinding and sieving with a 80-mesh sieve to obtain the adsorbent.
Further, the dosage ratio of the activated attapulgite to the modifier to the deionized water is 1 g: 1 g: 50 mL.
Further, the modifier is prepared by the following steps:
step S1: adding p-aminotoluene, p-chlorotoluene and toluene into a flask, introducing nitrogen for protection, adding palladium acetate, binaphthyl diphenyl phosphate and cesium carbonate, stirring and reacting for 5 hours at the temperature of 75 ℃, and preparing an intermediate 1 after the reaction is finished; the dosage ratio of the p-aminotoluene, the p-chlorotoluene, the toluene, the palladium acetate, the binaphthyl diphenyl phosphate and the cesium carbonate is 0.01 mol: 0.01 mol: 25mL of: 0.005 g: 0.006 g: 0.01 g;
the reaction process is as follows:
step S2: adding cyanuric chloride, N-diisopropylethylamine and tetrahydrofuran into a flask, introducing nitrogen for protection, stirring for 10-20min at the temperature of 0-5 ℃ and the rotation speed of 300r/min, then adding the intermediate 1, and reacting for 3-5h to obtain an intermediate 2; the dosage ratio of the cyanuric chloride, the N, N-diisopropylethylamine, the tetrahydrofuran and the intermediate 1 is 0.1 mol: 0.12 mol: 100mL of: 0.1 mol;
the reaction process is as follows:
step S3: adding the intermediate 2 and tetrahydrofuran into a flask, stirring for 10-20min at the temperature of 20-30 ℃ and the rotation speed of 200-400r/min, introducing chlorine, and reacting for 1-1.5h under the illumination condition to obtain an intermediate 3; the molar ratio of the intermediate 2 to chlorine is 1: 2;
the reaction process is as follows:
step S4: adding the intermediate 3, potassium carbonate and deionized water into a flask, stirring and mixing for 10-15min, then adding tetraethylammonium bromide, and carrying out reflux reaction for 1-1.5h at the temperature of 110-120 ℃ to prepare an intermediate 4; the dosage ratio of the intermediate 3, potassium carbonate, deionized water and tetraethylammonium bromide is 0.1 mol: 0.1 g: 100mL of: 0.2 mol;
the reaction process is as follows:
step S5: adding the intermediate 5 and tetrahydrofuran into a flask, stirring for 10min at the temperature of 0-5 ℃, then adding p-chlorobenzyl into the flask, and stirring for reacting for 2h at the temperature of 0-5 ℃ and the pH of 7 to prepare an intermediate 5; the dosage ratio of the intermediate 5 to the tetrahydrofuran to the p-chlorobenzyl is 0.01 mol: 50mL of: 0.02 mol;
the reaction process is as follows:
step S6: adding the intermediate 5 and N, N-dimethylformamide into a flask, stirring for 10-20min, heating to the temperature of 110-; the dosage ratio of the intermediate 5, the N, N-dimethylformamide solution and the trimethylamine solution is 0.1 mol: 50mL of: 10 mL;
the reaction process is as follows:
a production process of a cleaning solution for a semiconductor integrated circuit specifically comprises the following steps:
the method comprises the following steps: adding the adsorbent and isopropanol into a stirring kettle, and stirring and mixing for 30min at the temperature of 25-35 ℃ and the rotating speed of 500-700r/min to prepare a solution A;
step two: adding absolute ethyl alcohol and N, N-bis-hydroxyethyl dodecyl amide into a stirring kettle, and stirring and mixing for 20-40min at the temperature of 30 ℃ and the rotating speed of 600r/min to prepare a solution B;
step three: adding the solution A, the solution B, dichloromethane and 1, 4-butanediol into a stirring kettle, stirring and mixing for 25-35min at the temperature of 35 ℃ and the rotating speed of 300-.
(III) advantageous effects
The invention provides a cleaning solution for a semiconductor integrated circuit and a production process thereof. Compared with the prior art, the method has the following beneficial effects: the invention adds absolute ethyl alcohol, methylene dichloride, isopropanol and other organic solvents capable of removing oil stains as a cleaning liquid matrix, wherein N, N-bis-hydroxyethyl dodecyl amide is added to further improve the oil stain removing capability, an adsorbent is added, attapulgite is used as the matrix for modification preparation, a modifier is prepared for modification of attapulgite, the modifier is prepared by reacting amino of p-aminotoluene and active chlorine of p-chlorotoluene to prepare an intermediate 1, then-NH of the intermediate 1 is reacted with one active chlorine of chlorocyanogen to prepare an intermediate 2, then the intermediate 2 is reacted with chlorine under the illumination condition to ensure that two methyl groups of the intermediate 2 are chlorinated to prepare an intermediate 3, then halogen groups of the intermediate 3 are hydrolyzed to generate an intermediate 4 with hydroxyl groups, then two active chlorines of the intermediate 4 are reacted with hydroxyl groups of p-hydroxyl chlorobenzyl, the intermediate 5 is prepared, the intermediate 5 and trimethylamine are subjected to quaternization reaction to prepare the modifier, the modifier can be combined with the interior of the attapulgite through ion exchange reaction of two quaternary ammonium salt groups carried by the modifier, partial quaternary ammonium salt is exposed outside, the quaternary ammonium salt has positive charge and can be combined with the surface of a microorganism with negative charge, so that the microorganism on the surface of an integrated circuit is adsorbed and taken away, the overlook of the integrated circuit is prevented, the attapulgite has good adsorption effect, the adsorption effect of the modified attapulgite is better, the modifier has a structure of hydroxyl, benzene rings and the like, the attapulgite is easy to dissolve in an organic solvent matrix and can adsorb oily impurities, and a cleaning solution prepared by using the modifier has excellent adsorption capacity.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
Preparing a modifier, wherein the modifier is prepared by the following steps:
step S1: adding p-aminotoluene, p-chlorotoluene and toluene into a flask, introducing nitrogen for protection, adding palladium acetate, binaphthyl diphenyl phosphate and cesium carbonate, stirring and reacting for 5 hours at the temperature of 75 ℃, and preparing an intermediate 1 after the reaction is finished;
step S2: adding cyanuric chloride, N-diisopropylethylamine and tetrahydrofuran into a flask, introducing nitrogen for protection, stirring for 10min at the temperature of 0 ℃ and the rotation speed of 300r/min, then adding the intermediate 1, and reacting for 3h to obtain an intermediate 2;
step S3: adding the intermediate 2 and tetrahydrofuran into a flask, stirring for 10min at the temperature of 20 ℃ and the rotating speed of 200r/min, then introducing chlorine, and reacting for 1h under the illumination condition to obtain an intermediate 3;
step S4: adding the intermediate 3, potassium carbonate and deionized water into a flask, stirring and mixing for 10min, then adding tetraethylammonium bromide, and carrying out reflux reaction for 1h at the temperature of 110 ℃ to prepare an intermediate 4;
step S5: adding the intermediate 5 and tetrahydrofuran into a flask, stirring for 10min at the temperature of 0 ℃, then adding p-chlorobenzyl into the flask, and stirring for reacting for 2h at the temperature of 0 ℃ and the pH of 7 to obtain an intermediate 5;
step S5: adding the intermediate 5 and N, N-dimethylformamide into a flask, stirring for 10min, heating to 110 ℃, continuing stirring for 20min, then dropwise adding a trimethylamine solution into the flask under the conditions that the temperature is 130 ℃ and the rotating speed is 400r/min, and stirring for reacting for 2h to obtain the modifier.
Example 2
Preparing a modifier, wherein the modifier is prepared by the following steps:
step S1: adding p-aminotoluene, p-chlorotoluene and toluene into a flask, introducing nitrogen for protection, adding palladium acetate, binaphthyl diphenyl phosphate and cesium carbonate, stirring and reacting for 5 hours at the temperature of 75 ℃, and preparing an intermediate 1 after the reaction is finished;
step S2: adding cyanuric chloride, N-diisopropylethylamine and tetrahydrofuran into a flask, introducing nitrogen for protection, stirring for 15min at the temperature of 3 ℃ and the rotation speed of 300r/min, then adding the intermediate 1, and reacting for 4h to obtain an intermediate 2;
step S3: adding the intermediate 2 and tetrahydrofuran into a flask, stirring for 15min at the temperature of 25 ℃ and the rotating speed of 300r/min, then introducing chlorine, and reacting for 1.25h under the illumination condition to obtain an intermediate 3;
step S4: adding the intermediate 3, potassium carbonate and deionized water into a flask, stirring and mixing for 1.25min, then adding tetraethylammonium bromide, and carrying out reflux reaction for 1.25h at the temperature of 115 ℃ to prepare an intermediate 4;
step S5: adding the intermediate 5 and tetrahydrofuran into a flask, stirring for 10min at the temperature of 3 ℃, then adding p-chlorobenzyl into the flask, and stirring for reacting for 2h at the temperature of 3 ℃ and the pH of 7 to obtain an intermediate 5;
step S5: adding the intermediate 5 and N, N-dimethylformamide into a flask, stirring for 15min, heating to 112.5 ℃, continuing stirring for 20min, then dropwise adding a trimethylamine solution into the flask under the conditions that the temperature is 132.5 ℃ and the rotating speed is 400r/min, and stirring for reacting for 2.5h to obtain the modifier.
Example 3
Preparing a modifier, wherein the modifier is prepared by the following steps:
step S1: adding p-aminotoluene, p-chlorotoluene and toluene into a flask, introducing nitrogen for protection, adding palladium acetate, binaphthyl diphenyl phosphate and cesium carbonate, stirring and reacting for 5 hours at the temperature of 75 ℃, and preparing an intermediate 1 after the reaction is finished;
step S2: adding cyanuric chloride, N-diisopropylethylamine and tetrahydrofuran into a flask, introducing nitrogen for protection, stirring for 20min at the temperature of 5 ℃ and the rotation speed of 300r/min, then adding the intermediate 1, and reacting for 5h to obtain an intermediate 2;
step S3: adding the intermediate 2 and tetrahydrofuran into a flask, stirring for 20min at the temperature of 30 ℃ and the rotating speed of 400r/min, then introducing chlorine, and reacting for 1.5h under the illumination condition to obtain an intermediate 3;
step S4: adding the intermediate 3, potassium carbonate and deionized water into a flask, stirring and mixing for 15min, then adding tetraethylammonium bromide, and carrying out reflux reaction for 1.5h at the temperature of 120 ℃ to obtain an intermediate 4;
step S5: adding the intermediate 5 and tetrahydrofuran into a flask, stirring for 10min at the temperature of 5 ℃, then adding p-chlorobenzyl into the flask, and stirring for reacting for 2h at the temperature of 5 ℃ and the pH of 7 to obtain an intermediate 5;
step S5: adding the intermediate 5 and N, N-dimethylformamide into a flask, stirring for 20min, heating to 115 ℃, continuing stirring for 20min, then dropwise adding a trimethylamine solution into the flask under the conditions that the temperature is 135 ℃ and the rotating speed is 400r/min, and stirring for reacting for 3h to obtain the modifier.
Example 4
Preparing an adsorbent, wherein the adsorbent is prepared by the following steps:
the method comprises the steps of placing attapulgite raw soil at 100 ℃ for dehydration and activation for 4 hours to obtain activated attapulgite, then adding the activated attapulgite, the modifier prepared in example 2 and deionized water into a flask, reacting at a constant temperature of 50 ℃ and at a rotation speed of 300r/min for 5 hours, filtering and washing after the reaction is finished, drying at 80 ℃ for 12 hours, activating at 110 ℃ for 1 hour, and grinding and sieving with a 80-mesh sieve to obtain the adsorbent.
Example 5
A cleaning solution for a semiconductor integrated circuit comprises the following raw materials in parts by weight: 30 parts of absolute ethyl alcohol, 10 parts of isopropanol, 5 parts of N, N-bis-hydroxyethyl dodecyl amide, 5.2 parts of dichloromethane, 4.5 parts of 1, 4-butanediol and 4.3 parts of the adsorbent prepared in example 4;
the production process of the cleaning solution for the semiconductor integrated circuit specifically comprises the following steps:
the method comprises the following steps: adding the adsorbent and isopropanol into a stirring kettle, and stirring and mixing for 30min at the temperature of 25 ℃ and the rotating speed of 500r/min to prepare solution A;
step two: adding absolute ethyl alcohol and N, N-bis-hydroxyethyl dodecyl amide into a stirring kettle, and stirring and mixing for 20min at the temperature of 30 ℃ and the rotating speed of 600r/min to prepare a solution B;
step three: and adding the solution A, the solution B, dichloromethane and 1, 4-butanediol into a stirring kettle, and stirring and mixing for 25min at the temperature of 35 ℃ and the rotating speed of 300r/min to prepare the cleaning solution for the semiconductor integrated circuit.
Example 6
A cleaning solution for a semiconductor integrated circuit comprises the following raw materials in parts by weight: 40 parts of absolute ethyl alcohol, 15 parts of isopropanol, 10 parts of N, N-bis-hydroxyethyl dodecyl amide, 5.7 parts of dichloromethane, 5.5 parts of 1, 4-butanediol and 5.4 parts of the adsorbent prepared in example 4;
the production process of the cleaning solution for the semiconductor integrated circuit specifically comprises the following steps:
the method comprises the following steps: adding the adsorbent and isopropanol into a stirring kettle, and stirring and mixing for 30min at the temperature of 30 ℃ and the rotating speed of 600r/min to prepare a solution A;
step two: adding absolute ethyl alcohol and N, N-bis-hydroxyethyl dodecyl amide into a stirring kettle, and stirring and mixing for 30min at the temperature of 30 ℃ and the rotating speed of 600r/min to prepare a solution B;
step three: and adding the solution A, the solution B, dichloromethane and 1, 4-butanediol into a stirring kettle, and stirring and mixing for 30min at the temperature of 35 ℃ and the rotating speed of 400r/min to prepare the cleaning solution for the semiconductor integrated circuit.
Example 7
A cleaning solution for a semiconductor integrated circuit comprises the following raw materials in parts by weight: 50 parts of absolute ethyl alcohol, 20 parts of isopropanol, 15 parts of N, N-bis-hydroxyethyl dodecyl amide, 6.2 parts of dichloromethane, 6.5 parts of 1, 4-butanediol and 6.5 parts of the adsorbent prepared in example 4;
the production process of the cleaning solution for the semiconductor integrated circuit specifically comprises the following steps:
the method comprises the following steps: adding the adsorbent and isopropanol into a stirring kettle, and stirring and mixing for 30min at the temperature of 35 ℃ and the rotating speed of 700r/min to prepare solution A;
step two: adding absolute ethyl alcohol and N, N-bis-hydroxyethyl dodecyl amide into a stirring kettle, and stirring and mixing for 40min at the temperature of 30 ℃ and the rotating speed of 600r/min to prepare a solution B;
step three: and adding the solution A, the solution B, dichloromethane and 1, 4-butanediol into a stirring kettle, and stirring and mixing for 35min at the temperature of 35 ℃ and the rotating speed of 500r/min to prepare the cleaning solution for the semiconductor integrated circuit.
Comparative example: in comparison with example 6, no adsorbent was added.
The semiconductor integrated circuits were cleaned using examples 5 to 7 and comparative example, and the results are shown in the following table:
as can be seen from the above table, the cleaned semiconductor integrated circuits of examples 5-7 have the advantages of clean removal of oil stains and dust, no corrosion, and a drying rate 28-34% faster than that of the comparative example.
It is noted that, herein, relational terms such as first and second, and the like may be used solely to distinguish one entity or action from another entity or action without necessarily requiring or implying any actual such relationship or order between such entities or actions. Also, the terms "comprises," "comprising," or any other variation thereof, are intended to cover a non-exclusive inclusion, such that a process, method, article, or apparatus that comprises a list of elements does not include only those elements but may include other elements not expressly listed or inherent to such process, method, article, or apparatus.
Although embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that changes, modifications, substitutions and alterations can be made in these embodiments without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (10)
1. A cleaning liquid for a semiconductor integrated circuit, characterized in that: the feed comprises the following raw materials in parts by weight: 30-50 parts of absolute ethyl alcohol, 10-20 parts of isopropanol, 5-15 parts of N, N-bis-hydroxyethyl dodecyl amide, 5.2-6.2 parts of dichloromethane, 4.5-6.5 parts of 1, 4-butanediol and 4.3-6.5 parts of adsorbent;
the adsorbent is prepared by the following steps:
placing attapulgite raw soil at 100 ℃ for dehydration and activation for 4h to obtain activated attapulgite, then adding the activated attapulgite, a modifier and deionized water into a flask, reacting at a constant temperature of 50 ℃ and at a rotation speed of 300r/min for 5h, filtering and washing after the reaction is finished, drying at 80 ℃ for 12h, activating at 110 ℃ for 1h, and grinding and sieving with a 80-mesh sieve to obtain the adsorbent.
2. The cleaning liquid for semiconductor integrated circuits according to claim 1, wherein: the dosage ratio of the activated attapulgite to the modifier to the deionized water is 1 g: 1 g: 50 mL.
3. The cleaning liquid for semiconductor integrated circuits according to claim 1, wherein: the modifier is prepared by the following steps:
step S1: adding p-aminotoluene, p-chlorotoluene and toluene into a flask, introducing nitrogen for protection, adding palladium acetate, binaphthyl diphenyl phosphate and cesium carbonate, stirring and reacting for 5 hours at the temperature of 75 ℃, and preparing an intermediate 1 after the reaction is finished;
step S2: adding cyanuric chloride, N-diisopropylethylamine and tetrahydrofuran into a flask, introducing nitrogen for protection, stirring for 10-20min at the temperature of 0-5 ℃ and the rotation speed of 300r/min, then adding the intermediate 1, and reacting for 3-5h to obtain an intermediate 2;
step S3: adding the intermediate 2 and tetrahydrofuran into a flask, stirring for 10-20min at the temperature of 20-30 ℃ and the rotation speed of 200-400r/min, introducing chlorine, and reacting for 1-1.5h under the illumination condition to obtain an intermediate 3;
step S4: adding the intermediate 3, potassium carbonate and deionized water into a flask, stirring and mixing for 10-15min, then adding tetraethylammonium bromide, and carrying out reflux reaction for 1-1.5h at the temperature of 110-120 ℃ to prepare an intermediate 4;
step S5: adding the intermediate 5 and tetrahydrofuran into a flask, stirring for 10min at the temperature of 0-5 ℃, then adding p-chlorobenzyl into the flask, and stirring for reacting for 2h at the temperature of 0-5 ℃ and the pH of 7 to prepare an intermediate 5;
step S5: adding the intermediate 5 and N, N-dimethylformamide into a flask, stirring for 10-20min, heating to the temperature of 110-.
4. A cleaning solution for semiconductor integrated circuits according to claim 3, characterized in that: the dosage ratio of the p-aminotoluene, the p-chlorotoluene, the toluene, the palladium acetate, the binaphthyl diphenyl phosphate and the cesium carbonate in the step S1 is 0.01 mol: 0.01 mol: 25mL of: 0.005 g: 0.006 g: 0.01 g.
5. A cleaning solution for semiconductor integrated circuits according to claim 3, characterized in that: the dosage ratio of the cyanuric chloride, the N, N-diisopropylethylamine, the tetrahydrofuran and the intermediate 1 in the step S2 is 0.1 mol: 0.12 mol: 100mL of: 0.1 mol.
6. A cleaning solution for semiconductor integrated circuits according to claim 3, characterized in that: the molar ratio of the intermediate 2 to the chlorine gas in the step S3 is 1: 2.
7. A cleaning solution for semiconductor integrated circuits according to claim 3, characterized in that: the dosage ratio of the intermediate 3, the potassium carbonate, the deionized water and the tetraethylammonium bromide in the step S4 is 0.1 mol: 0.1 g: 100mL of: 0.2 mol.
8. A cleaning solution for semiconductor integrated circuits according to claim 3, characterized in that: in the step S5, the dosage ratio of the intermediate 5, the tetrahydrofuran and the p-chlorobenzyl is 0.01 mol: 50mL of: 0.02 mol.
9. A cleaning solution for semiconductor integrated circuits according to claim 3, characterized in that: the dosage ratio of the intermediate 5, the N, N-dimethylformamide solution and the trimethylamine solution in the step S6 is 0.1 mol: 50mL of: 10 mL.
10. The process according to claim 1, wherein the cleaning liquid for semiconductor integrated circuits comprises: the method specifically comprises the following steps:
the method comprises the following steps: adding adsorbent and isopropanol into a stirring kettle, stirring and mixing at 25-35 deg.C for 30min to obtain solution A;
step two: adding absolute ethanol and N, N-bis-hydroxyethyl dodecyl amide into a stirring kettle, and stirring and mixing at 30 ℃ for 20-40min to obtain solution B;
step three: adding the solution A, the solution B, dichloromethane and 1, 4-butanediol into a stirring kettle, stirring and mixing for 25-35min at the temperature of 35 ℃ and the rotating speed of 300-.
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| CN101607190A (en) * | 2009-07-28 | 2009-12-23 | 淮阴工学院 | A kind of preparation of attapulgite of selectively absorbing tannin |
| CN106512924A (en) * | 2016-12-14 | 2017-03-22 | 严帝 | Attapulgite adsorbent with large adsorption capacity and preparation method thereof |
| CN106693902A (en) * | 2016-12-14 | 2017-05-24 | 严帝 | Quaternary ammonium salt modified attapulgite adsorbent and preparation method thereof |
| CN108690744A (en) * | 2018-08-01 | 2018-10-23 | 芜湖彰鸿工程技术有限公司 | A kind of robot PCB circuit board high-efficient cleaning washing lotion |
| CN108728267A (en) * | 2018-07-04 | 2018-11-02 | 合肥帧讯低温科技有限公司 | High-performance oil and stain removal detergent for kitchen |
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2021
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|---|---|---|---|---|
| CN101607190A (en) * | 2009-07-28 | 2009-12-23 | 淮阴工学院 | A kind of preparation of attapulgite of selectively absorbing tannin |
| CN106512924A (en) * | 2016-12-14 | 2017-03-22 | 严帝 | Attapulgite adsorbent with large adsorption capacity and preparation method thereof |
| CN106693902A (en) * | 2016-12-14 | 2017-05-24 | 严帝 | Quaternary ammonium salt modified attapulgite adsorbent and preparation method thereof |
| CN108728267A (en) * | 2018-07-04 | 2018-11-02 | 合肥帧讯低温科技有限公司 | High-performance oil and stain removal detergent for kitchen |
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Application publication date: 20211029 |