CN112898185A - Fluorine-containing compound for immersion photoresist, preparation method thereof and photoresist - Google Patents
Fluorine-containing compound for immersion photoresist, preparation method thereof and photoresist Download PDFInfo
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- CN112898185A CN112898185A CN202110110177.7A CN202110110177A CN112898185A CN 112898185 A CN112898185 A CN 112898185A CN 202110110177 A CN202110110177 A CN 202110110177A CN 112898185 A CN112898185 A CN 112898185A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1809—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/189—Purification, separation, stabilisation, use of additives
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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
- G03F7/004—Photosensitive materials
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Abstract
The invention provides a fluorine-containing compound for an immersion photoresist and a preparation method thereof, wherein the method comprises the following steps: adding a prepared compound, 4-dimethylaminopyridine, l-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride and trichloromethane into a reaction vessel, and uniformly mixing to form a reaction system; dropwise adding N, N-dimethyl propane diamine into the reaction system, and reacting to generate a fluorine-containing compound; wherein the chemical structure of the preparatory compound is
n ≧ 1, is an integer. The invention also provides the immersion photoresist added with the fluorine-containing compound. The fluorine-containing compound prepared by the preparation process provided by the technical scheme can be prevented from being added into the photoresistThe impurities in the pure water pollute the lens of the photoetching machine, and the pollution of the impurities to the lens is effectively reduced. The technical scheme provided by the invention replaces the existing formula of adding the hydrophobic layer, and has the advantages of simple process, short production period, improved production efficiency, saved production cost and the like.
Description
Technical Field
The invention belongs to the technical field of chemistry, and particularly relates to a fluorine-containing compound for an immersion photoresist, a preparation method of the fluorine-containing compound and the photoresist.
Background
The photoresist is one of the key materials in the field of integrated circuit manufacturing, the technical requirements on the photoresist are higher and higher along with the continuous development of the manufacturing technology, and in order to meet the increasingly rigorous process conditions, a photoresist product with higher performance needs to be developed. As the integrated circuit manufacturing process enters a technical node below 45nm, the immersion lithography process is widely used, and pure water is used as a medium for a lens of the immersion lithography machine, so that in order to prevent impurities in the pure water from polluting the lens of the lithography machine in the production process, the impurity precipitation amount of the immersion photoresist needs to be strictly controlled, and the pollution of the impurities to the lens is reduced.
Considering that the photoresist can be directly contacted with pure water in an exposure process, and the impurity precipitation amount of the photoresist can pollute the pure water, so that a lens of a photoetching machine is damaged.
In the above solution, the transparent hydrophobic layer material needs to be purchased separately, and after the immersion photoresist is coated, a coating process of the hydrophobic layer needs to be added, so that the process complexity is increased, the production period is prolonged, the production efficiency is lowered, and the equipment cost is increased.
Disclosure of Invention
The embodiment of the invention provides a fluorine-containing compound for an immersion photoresist, a preparation method thereof and the photoresist, aiming at solving the defects of increased process complexity, long production period, low production efficiency and increased production cost of the existing scheme for controlling the impurity precipitation amount of the immersion photoresist.
The embodiment of the invention is realized by that the fluorine-containing compound for the immersion photoresist comprises the following steps:
adding a prepared compound, 4-dimethylaminopyridine, l-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride and trichloromethane into a reaction vessel, and uniformly mixing to form a reaction system;
dropwise adding N, N-dimethyl propane diamine into the reaction system, and reacting to generate the fluorine-containing compound;
wherein the chemical structure of the preparation compound is
In addition, the invention also provides a fluorine-containing compound for immersion photoresist, which is prepared by the preparation method.
In addition, the invention also provides a photoresist which is added with the fluorine-containing compound prepared by the preparation method.
The fluorine-containing compound for the immersion photoresist obtained by the manufacturing process is added into a conventional photoresist finished product after being purified, and the fluorine-containing photoresist is prepared after being fully and uniformly stirred. The fluorine-containing photoresist is subjected to a film coating experiment, after a 12-inch silicon wafer is subjected to film coating and baking, the silicon wafer is placed in a container filled with pure water to test the separation of impurities, after the silicon wafer is soaked for 48 hours, the change condition of the impurity content in the pure water is measured, and the result is compared with the formula of a hydrophobic layer, so that the result shows that the impurities separated out by the fluorine-containing photoresist in the scheme are obviously lower than those in a comparison group. The fluorine-containing compound prepared by the preparation process provided by the technical scheme is added into the photoresist, so that impurities in pure water can be prevented from polluting a lens of a photoetching machine, and the pollution of the impurities to the lens is effectively reduced. Therefore, the technical scheme provided by the invention replaces the existing formula of the hydrophobic layer, and has the advantages of simple process, short production period, improved production efficiency, production cost saving and the like.
Drawings
FIG. 1 is a flow chart of a method of making a fluorine-containing compound for use in an immersion photoresist according to an embodiment of the present invention.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is described in further detail below with reference to the accompanying drawings and embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
As shown in fig. 1, an embodiment of the present invention provides a method for preparing a fluorine-containing compound for an immersion photoresist. The preparation method of the fluorine-containing compound for the immersion photoresist comprises the following steps:
step S10, adding a preparation compound, 4-dimethylaminopyridine, l-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride and trichloromethane into a reaction vessel, and uniformly mixing to form a reaction system;
the reaction vessel can be a reactor, a reaction kettle, a decomposing kettle, a polymerizing kettle and the like, and can also be a glass or alloy vessel of other chemical laboratories.
The addition ratio of each reactant in the reaction vessel is as follows:
preparing a compound: 4-dimethylaminopyridine: l-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride (EDCI): the trichloromethane is 1:1:1: 2-1: 1:1: 15. The unit of measurement of the addition ratio may be one of the mass ratio, volume ratio, and the like of the substance, and is preferably the mass ratio of the substance.
Further, the addition ratio of each reactant in the reaction vessel is preferably a preliminary compound: 4-dimethylaminopyridine: l-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride (EDCI): the trichloromethane is 1:1:1: 5-1: 1:1: 10.
And step S20, dropwise adding N, N-dimethyl propane diamine into the reaction system, and reacting to generate the fluorine-containing compound.
The amount of N, N-dimethylpropylenediamine added to the reaction mixture depends on the amount of the preliminary compound, and the amount of N, N-dimethylpropylenediamine charged is generally 1 to 3 times the amount of the preliminary compound. In order to reduce the residual amount of the reactant, the dosage of the N, N-dimethylpropylenediamine is preferably 1.2 to 2.5 times of that of the preparation compound.
Wherein the chemical structure of the preparatory compound is:
Furthermore, the value of n in the chemical structural formula of the preparation compound is preferably 1-12.
In one embodiment, after the last reactant, i.e., N-dimethylpropylenediamine, is added to the reaction system, the reaction is terminated after 24 hours at room temperature, and the purification treatment of the product is performed.
The purification treatment of the product may comprise the following operations:
firstly, washing a reaction solution by deionized water and saturated salt water to remove water-soluble impurities;
separating the organic phase, drying the organic phase with anhydrous sodium sulfate, and optionally drying the organic phase with other reagents, such as zeolite;
finally filtering the filtrate, and distilling at 50-90 deg.C under normal pressure to remove solvent, preferably at 70 deg.C.
And (3) after the reaction of the reactants is finished, purifying the obtained fluorine-containing compound, adding the purified fluorine-containing compound into a conventional photoresist finished product, and fully and uniformly stirring to obtain the fluorine-containing photoresist. Wherein the purity of the purified fluorine-containing compound is up to the technical standard of photoresist. Further, a coating experiment is carried out on the fluorine-containing photoresist, after coating and baking are carried out on a 12-inch silicon wafer, the silicon wafer is placed into a container filled with pure water to test the separation of impurities, after soaking for 48 hours, the change condition of the impurity content in the pure water is measured, and the result is compared with the formula of the hydrophobic layer, so that the result shows that the impurities separated out by the fluorine-containing photoresist in the scheme are obviously lower than those in a comparison group. The addition of the fluorine-containing compound changes the surface energy of the photoresist film, improves the hydrophobicity of the photoresist to contain fluorine, and reduces the precipitation of small molecular compounds in the liquid pure water of the lens, so that the fluorine-containing photoresist is coated on a silicon wafer to play a role in isolating impurities.
According to experimental results, the fluorine-containing compound prepared by the preparation process provided by the technical scheme is added into the photoresist, so that impurities in pure water can be prevented from polluting the lens of the photoetching machine, and the pollution of the impurities to the lens is effectively reduced. Therefore, the technical scheme provided by the invention replaces the existing formula of the hydrophobic layer, and has the advantages of simple process, short production period, improved production efficiency, production cost saving and the like.
The formula of the hydrophobic layer is a commonly used method for solving the problem in the prior art that pure water is polluted by the precipitation amount of impurities of the photoresist, so that a lens of a photoetching machine is damaged.
The following examples illustrate the preparation of fluorine-containing compounds for immersion photoresists according to embodiments of the invention and demonstrate that photoresists incorporating such fluorine-containing compounds are more effective at sequestering contaminants.
Example one
To a 5L reaction vessel were added 2mol of compound 1(n ═ 2), 2mol of 4-dimethylaminopyridine, and 2mol of ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride (EDCI), 6mol of chloroform in that order. And (3) dropwise adding 1.2mol of N, N-dimethyl propane diamine into the system, naturally heating to room temperature after dropwise adding is finished, and stopping reaction after reaction is continued for 24 hours. The reaction solution was washed with deionized water and saturated brine, the organic phase was separated, dried over anhydrous sodium sulfate for 48 hours, the solid was filtered and the liquid was collected and the solvent was distilled off at 70 ℃ under normal pressure to obtain the product. And purifying the prepared product to the technical standard of a photoresist product, adding the product into a finished photoresist product, and fully stirring to prepare the photoresist product. And (2) carrying out a film coating experiment on the photoresist product added with the additive, placing the photoresist product into a container filled with pure water to test the separation of impurities after film coating and baking on a 12-inch silicon wafer, soaking for 48 hours, measuring the change condition of the content of the impurities in the pure water (see table 1 below), and comparing the change condition with the formula of the hydrophobic layer, wherein the result shows that the photoresist product is qualified.
Table 1 experimental results in example one
Example 2
To a 5L reaction vessel were added 2mol of compound 1(n ═ 1), 2mol of 4-dimethylaminopyridine, and 2mol of ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride (EDCI), 8mol of chloroform in that order. And (3) dropwise adding 1.6mol of N, N-dimethyl propane diamine into the system, naturally heating to room temperature after dropwise adding is finished, and stopping reaction after reaction is continued for 24 hours. The reaction solution was washed with deionized water and saturated brine, the organic phase was separated, dried over anhydrous sodium sulfate for 48 hours, the solid was filtered and the liquid was collected and the solvent was distilled off at 70 ℃ under normal pressure to obtain the product. And purifying the prepared product to the technical standard of a photoresist product, adding the product into a finished photoresist product, and fully stirring to prepare the photoresist product. And (3) carrying out a film coating experiment on the photoresist product added with the additive, carrying out film coating and baking on a 12-inch silicon wafer, putting the silicon wafer into a container filled with pure water to test the precipitation of impurities, soaking the silicon wafer for 48 hours, measuring the change condition of the content of the impurities in the pure water (see the following table), and comparing the change condition with the formula of the hydrophobic layer, wherein the result shows that the photoresist product is qualified.
Table 2 experimental results in example two
Example 3
To a 5L reaction vessel were added 2mol of compound 1(n ═ 1), 2mol of 4-dimethylaminopyridine, and 2mol of ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride (EDCI), 7mol of chloroform in that order. And (3) dropwise adding 2.1mol of N, N-dimethyl propane diamine into the system, naturally heating to room temperature after dropwise adding is finished, and stopping reaction after reaction is continued for 24 hours. The reaction solution was washed with deionized water and saturated brine, the organic phase was separated, dried over anhydrous sodium sulfate for 48 hours, the solid was filtered and the liquid was collected and the solvent was distilled off at 70 ℃ under normal pressure to obtain the product. And purifying the prepared product to the technical standard of a photoresist product, adding the product into a finished photoresist product, and fully stirring to prepare the photoresist product. And (3) carrying out a film coating experiment on the photoresist product added with the additive, carrying out film coating and baking on a 12-inch silicon wafer, putting the silicon wafer into a container filled with pure water to test the precipitation of impurities, soaking the silicon wafer for 48 hours, measuring the change condition of the content of the impurities in the pure water (see the following table), and comparing the change condition with the formula of the hydrophobic layer, wherein the result shows that the photoresist product is qualified.
Table 3 experimental results in example three
The invention has the beneficial effects that the fluorine-containing compound obtained by the reaction in the invention is added into the conventional photoresist finished product after being purified, and the fluorine-containing photoresist is prepared after being fully and uniformly stirred. The fluorine-containing photoresist is subjected to a film coating experiment, after a 12-inch silicon wafer is subjected to film coating and baking, the silicon wafer is placed in a container filled with pure water to test the separation of impurities, after the silicon wafer is soaked for 48 hours, the change condition of the impurity content in the pure water is measured, and the result is compared with the formula of a hydrophobic layer, so that the result shows that the impurities separated out by the fluorine-containing photoresist in the scheme are obviously lower than those in a comparison group.
According to experimental results, the fluorine-containing compound prepared by the preparation process provided by the technical scheme is added into the photoresist, so that impurities in pure water can be prevented from polluting the lens of the photoetching machine, and the pollution of the impurities to the lens is effectively reduced. Therefore, the technical scheme provided by the invention replaces the existing formula of the hydrophobic layer, and has the advantages of simple process, short production period, improved production efficiency, production cost saving and the like.
Further, the invention also provides a fluorine-containing compound for immersion photoresist, which is prepared by the preparation method of the embodiment.
And the fluorine-containing compound for the immersion photoresist is added into a conventional photoresist finished product after being purified, and the fluorine-containing photoresist is prepared after being fully and uniformly stirred. The fluorine-containing photoresist is subjected to a film coating experiment, after a 12-inch silicon wafer is subjected to film coating and baking, the silicon wafer is placed in a container filled with pure water to test the separation of impurities, after the silicon wafer is soaked for 48 hours, the change condition of the impurity content in the pure water is measured, and the result is compared with the formula of a hydrophobic layer, so that the result shows that the impurities separated out by the fluorine-containing photoresist in the scheme are obviously lower than those in a comparison group.
According to experimental results, the fluorine-containing compound prepared by the preparation process provided by the technical scheme is added into the photoresist, so that impurities in pure water can be prevented from polluting the lens of the photoetching machine, and the pollution of the impurities to the lens is effectively reduced. Therefore, the technical scheme provided by the invention replaces the existing formula of the hydrophobic layer, and has the advantages of simple process, short production period, improved production efficiency, production cost saving and the like.
Further, the invention also provides a photoresist which comprises the fluorine-containing compound for the immersion photoresist prepared by the preparation method in the embodiment.
The fluorine-containing compound for the immersion photoresist prepared by the preparation method is added into a conventional photoresist finished product after being purified, and the fluorine-containing photoresist is prepared after being fully and uniformly stirred. The fluorine-containing photoresist is subjected to a film coating experiment, after a 12-inch silicon wafer is subjected to film coating and baking, the silicon wafer is placed in a container filled with pure water to test the separation of impurities, after the silicon wafer is soaked for 48 hours, the change condition of the impurity content in the pure water is measured, and the result is compared with the formula of a hydrophobic layer, so that the result shows that the impurities separated out by the fluorine-containing photoresist in the scheme are obviously lower than those in a comparison group.
According to experimental results, the fluorine-containing compound prepared by the preparation process provided by the technical scheme is added into the photoresist, so that impurities in pure water can be prevented from polluting the lens of the photoetching machine, and the pollution of the impurities to the lens is effectively reduced. Therefore, the technical scheme provided by the invention replaces the existing formula of the hydrophobic layer, and has the advantages of simple process, short production period, improved production efficiency, production cost saving and the like.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents and improvements made within the spirit and principle of the present invention are intended to be included within the scope of the present invention.
Claims (9)
1. A method of preparing a fluorochemical for immersion photoresist, said method comprising the steps of:
adding a prepared compound, 4-dimethylaminopyridine, l-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride and trichloromethane into a reaction vessel, and uniformly mixing to form a reaction system;
dropwise adding N, N-dimethyl propane diamine into the reaction system, and reacting to generate the fluorine-containing compound;
wherein the chemical structure of the preparation compound is
2. The method of claim 1, wherein n is an integer and has a value in the range of 1 to 12.
3. The method for preparing a fluorine-containing compound for an immersion photoresist according to claim 1,
the preparation compound is: 4-dimethylaminopyridine: l-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride (EDCI): the trichloromethane is 1:1:1: 2-1: 1:1: 15;
the feeding amount of the N, N-dimethyl propane diamine is 1-3 times of that of the preparation compound.
4. The method of claim 3, wherein the preparation compound: 4-dimethylaminopyridine: l-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride (EDCI): the trichloromethane is 1:1:1: 5-1: 1:1: 10;
the dosage of the N, N-dimethyl propane diamine is 1.2-2.5 times of that of the preparation compound.
5. The method for producing a fluorine-containing compound for an immersion photoresist according to any of claims 1 to 4, wherein the step of dropping N, N-dimethylpropylenediamine into the reaction system to react to produce the fluorine-containing compound further comprises:
stopping the reaction after reacting at room temperature for a preset time;
and purifying the reaction liquid to obtain the fluorine-containing compound.
6. The method of claim 5, wherein the step of purifying the reaction solution comprises:
washing the reaction solution with deionized water and saturated brine;
separating the organic phase and drying the organic phase;
filtering to obtain filtrate, and removing the solvent in the filtrate to obtain the fluorine-containing compound.
7. The method of claim 6, wherein the solvent is removed from the filtrate by atmospheric distillation at 50-90 ℃.
8. A fluorine-containing compound for use in an immersion photoresist, wherein the fluorine-containing compound is obtained by the production method according to any one of claims 1 to 7.
9. A photoresist characterized by adding the fluorine-containing compound according to claim 8 to the photoresist.
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Citations (4)
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| CN1107585A (en) * | 1994-01-25 | 1995-08-30 | 莫顿国际股份有限公司 | Waterborne photoresists having non-ionic fluorocarbon surfactants |
| CN1470010A (en) * | 2000-10-13 | 2004-01-21 | 纳幕尔杜邦公司 | Dissolution inhibitors in photoresist compositions for microlithography |
| CN1849557A (en) * | 2003-07-23 | 2006-10-18 | 帝斯曼知识产权资产管理有限公司 | Dissolution inhibitors in photoresist compositions for microlithography |
| CN1896039A (en) * | 2002-08-21 | 2007-01-17 | 旭硝子株式会社 | Fluorinated compound |
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2021
- 2021-01-26 CN CN202110110177.7A patent/CN112898185B/en active Active
Patent Citations (4)
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| CN1107585A (en) * | 1994-01-25 | 1995-08-30 | 莫顿国际股份有限公司 | Waterborne photoresists having non-ionic fluorocarbon surfactants |
| CN1470010A (en) * | 2000-10-13 | 2004-01-21 | 纳幕尔杜邦公司 | Dissolution inhibitors in photoresist compositions for microlithography |
| CN1896039A (en) * | 2002-08-21 | 2007-01-17 | 旭硝子株式会社 | Fluorinated compound |
| CN1849557A (en) * | 2003-07-23 | 2006-10-18 | 帝斯曼知识产权资产管理有限公司 | Dissolution inhibitors in photoresist compositions for microlithography |
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| KOJI HONDA ET AL.: "Molecular Aggregation Structure and Surface Properties of Poly(fluoroalkyl acrylate) Thin Films", 《MACROMOLECULES》 * |
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