CN112679499A - Sulfonium sulfonate photo-acid generator synthesized from matrine and synthesis method thereof - Google Patents
Sulfonium sulfonate photo-acid generator synthesized from matrine and synthesis method thereof Download PDFInfo
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Abstract
The invention discloses a sulfonium sulfonate photo-acid generator synthesized from matrine, relates to the field of photoresist, and particularly relates to a photo-acid generator, wherein the sulfonium sulfonate photo-acid generator synthesized from matrine has a structural formula as follows:
Description
Technical Field
The invention relates to the field of photoresist, in particular to a sulfonium sulfonate photo-acid generator synthesized from matrine and a synthesis method thereof.
Background
The photolithography technique is a fine processing technique for transferring a pattern designed on a mask plate to a pattern on a substrate by using the chemical sensitivity of a photoresist under the action of visible light, ultraviolet rays, electron beams and the like through the processes of exposure, development, etching and the like.
The development of the photoetching technology cannot be separated from the development of the photoresist, the chemical amplification photoresist is a widely-applied photoresist, the main components are resin, a photoacid generator and corresponding additives and solvents, the materials have photochemical sensitivity, and the solubility of the materials in a developing solution is changed through photochemical reaction. Chemically amplified photoresists are classified into positive photoresists and negative photoresists according to the difference of photochemical reaction mechanism: after exposure, the solubility of the photoresist in a developing solution is increased, and the photoresist with the same pattern as that of the mask is obtained and is called as a positive photoresist; after exposure, the photoresist has reduced solubility or even no solubility in a developing solution, and a negative photoresist with a pattern opposite to that of the mask is obtained.
Acid diffusion is an important factor affecting the pattern shape and line edge roughness, and in order to reduce the acid diffusion, the following two schemes are often adopted: the anion of the photoacid generator is designed to be a structure with a larger molecular weight or some weakly basic quencher is added when the photoresist is formulated. The former is based on the principle that molecules with macromolecular structures diffuse slowly, and the latter is based on the principle that basic compounds are used for neutralizing diffused acids. The two schemes are usually used in conjunction.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provides a sulfonium sulfonate photo-acid generator synthesized from matrine and a synthesis method thereof.
In order to solve the technical problems, the invention provides the following technical scheme:
the invention relates to a sulfonium sulfonate photo-acid generator synthesized from matrine, which has the structural formula as follows:
r is fluorine substituted alkyl.
As a preferred embodiment of the present invention, the photoacid generator includes:
a synthetic method of a sulfonium sulfonate photo-acid generator synthesized from matrine comprises the following specific synthetic steps:
wherein M is an alkali metal; r1Is an alkane;
the first step is as follows: dissolving 2-3 equivalents of diisopropylamine into a tetrahydrofuran solution, cooling to minus 60-80 ℃, slowly dropwise adding 2-3 equivalents of n-butyllithium tetrahydrofuran solution into the solution, after dropwise adding, stirring and reacting the reaction solution at minus 60-80 ℃ for 20-40 minutes, slowly dropwise adding 1 equivalent of matrine tetrahydrofuran solution into the reaction solution, and after dropwise adding, continuously stirring at minus 60-80 ℃ for 20-40 minutes; then dripping 1.2-2 equivalents of tetrahydrofuran solution of dialkyl carbonate into the reaction solution, stirring for 20-40 minutes at minus 60-80 ℃, naturally heating to room temperature, and continuously stirring for reaction for 3-6 hours; slowly quenching the reaction liquid by using a saturated ammonium chloride aqueous solution, extracting a water phase by using ethyl acetate, combining organic phases, drying the organic phases by using anhydrous sodium sulfate, concentrating to obtain a crude product, and purifying the crude product by using column chromatography to obtain an intermediate I;
the second step is that: adding 1-1.5 equivalents of aqueous solution of inorganic base into 1 equivalent of ethanol solution of the intermediate I, stirring for 1.5-3 hours at room temperature, neutralizing with dilute hydrochloric acid, concentrating the reaction solution, adding ethanol into the solid, stirring, filtering, drying the filtrate with anhydrous sodium sulfate, and concentrating to obtain an intermediate II;
the third step: adding 1 equivalent of the intermediate II, 1-1.2 equivalents of the intermediate III and 0.1-0.2 equivalent of an acid catalyst into toluene, heating and refluxing for 16-20 hours, and cooling to room temperature; filtering the mixture to obtain a solid, adding the solid into methyl tert-butyl ether for pulping, filtering the mixed solution, and collecting and drying a filter cake to obtain an intermediate IV;
the fourth step: under the protection of inert gas, dissolving 1 equivalent of (cyclohexyl-1, 5-dialkenyloxy) -trimethyl-silane and 1 equivalent of tetramethylene sulfoxide in chloroform, cooling to minus 20-minus 40 ℃, slowly adding 1.3-2.0 equivalents of trifluoroacetic anhydride in 30 minutes, stirring for reacting for 20-40 minutes, adding 1 equivalent of saturated aqueous solution of an intermediate III under stirring, stirring for reacting for 0.5-1.5 hours, recovering to room temperature after the reaction is finished, separating water and chloroform, extracting an aqueous phase with chloroform, concentrating a chloroform phase under vacuum to obtain a crude product, and washing the crude product with diisopropyl ether to obtain the light acid generator.
In a preferred embodiment of the present invention, the dialkyl carbonate is dimethyl carbonate or diethyl carbonate.
In a preferred embodiment of the present invention, the inorganic base is sodium hydroxide or potassium hydroxide.
As a preferred technical scheme of the invention, the acid catalyst is p-toluenesulfonic acid or sulfuric acid.
In a preferred embodiment of the present invention, M is potassium, sodium or lithium.
Compared with the prior art, the invention has the following beneficial effects:
1) the matrine structure has larger molecular weight, and the synthesized photo-acid generator keeps the structure of the matrine, not only has larger molecular weight, but also is alkalescent, can effectively reduce the diffusion of acid, is beneficial to improving the edge roughness of a photoetching graph and improving the graph resolution.
2) The photo-acid generator has hydrophilic-lipophilic balance, can be well dissolved in a solvent, and has proper adhesion.
3) The photoacid generator contains very large aliphatic rings and has excellent etching resistance.
4) The synthesized photoacid generator does not contain benzene rings, has better transparency at 193nm, and has less influence on the transparency of 193nm photoresist when being doped to form 193nm photoresist, thereby being beneficial to better exposure of the photoresist.
5) The synthetic route is simple.
Detailed Description
It should be understood that the preferred embodiments described herein are for purposes of illustration and explanation only and are not intended to limit the present invention.
Example 1
a. Dissolving diisopropylamine (20.5g,203mmol) into a tetrahydrofuran solution (250g), cooling to-78 ℃, slowly dropwise adding a tetrahydrofuran solution of n-butyllithium (2.5M, 80ml), stirring the reaction solution at-78 ℃ for 30 minutes after dropwise adding, slowly dropwise adding a tetrahydrofuran (100g) solution of matrine 1-1(20g, 81mmol) into the reaction solution, and continuously stirring at-78 ℃ for 30 minutes after dropwise adding; then, a solution of dimethyl carbonate (11g, 122mmol) in tetrahydrofuran (100g) was added dropwise to the reaction mixture, and the mixture was stirred at-78 ℃ for 30 minutes, then naturally warmed to room temperature, and stirred to react for 4 hours. Slowly quenching the reaction solution with saturated ammonium chloride aqueous solution (300ml), extracting the water phase with ethyl acetate (250ml) for three times, combining the organic phases, drying the organic phases with anhydrous sodium sulfate, concentrating to obtain a crude product, and purifying the crude product by column chromatography to obtain the compound 1-2(18g, 59mmol, yield 73%)
b. A solution of sodium hydroxide (2.5g, 62.5mmol) in water (20g) was added to a solution of compound 1-2(18g, 59mmol) in ethanol (100g), stirred at room temperature for 2 hours, neutralized with dilute hydrochloric acid (2.5M), the reaction was concentrated, the solid was added to ethanol (300ml), stirred for half an hour, filtered, the filtrate was dried over anhydrous sodium sulfate, and concentrated to give compound 1-3(16.6g, 56.8mmol, 96.6% yield).
c. Compound 1-3(16.6g, 56.8mmol), sodium 1,1, 2, 2-tetrafluoro-4-hydroxybutanesulfonate (15g, 60mmol) and p-toluenesulfonic acid monohydrate (1.6g, 8.4mmol) were added to toluene (350g), heated under reflux for 18 hours, and cooled to room temperature. The mixture was filtered to give a solid, which was slurried in methyl t-butyl ether, the mixture was filtered, and the oven dried cake was collected to give compound 3-4 as a solid (24g, 46mmol, 81% yield).
d. Under the protection of nitrogen flow, (cyclohexa-1, 5-dienyloxy) -trimethyl-silane (7.8g, 46mmol) and tetramethylene sulfoxide (5g, 48mmol) were dissolved in chloroform (500g), cooled to-30 ℃, trifluoroacetic anhydride (15g, 71mmol) was slowly added over 30 minutes, stirred for reaction for 30 minutes, 1-4(24g, 46mmol) of saturated aqueous solution was added under stirring, stirred for reaction for 1 hour, the reaction was brought to room temperature at the end, water and chloroform were separated, the aqueous phase was extracted with chloroform, the chloroform phase was concentrated under vacuum to give the crude product, which was washed with diisopropyl ether to give 1-5(26g, 38mmol, yield 83%).
Example 2
a. Dissolving diisopropylamine (20.5g,203mmol) into a tetrahydrofuran solution (250g), cooling to-78 ℃, slowly dropwise adding a tetrahydrofuran solution of n-butyllithium (2.5M, 80ml), stirring the reaction solution at-78 ℃ for 30 minutes after dropwise adding, adding matrine 2-1(20g, 81mmol) into tetrahydrofuran (100g) to prepare a solution, slowly dropwise adding the solution into the reaction solution at-78 ℃, and continuously stirring at-78 ℃ for 30 minutes after dropwise adding; dimethyl carbonate (11g, 122mmol) is added into tetrahydrofuran (100g) to prepare a solution, the solution is dripped into the reaction solution at-78 ℃, stirred for 30 minutes at-78 ℃, naturally heated to room temperature, and stirred for reaction for 4 hours. The reaction was slowly quenched with saturated aqueous ammonium chloride (300ml), the aqueous phase was extracted three times with ethyl acetate (250ml), the organic phases were combined, dried over anhydrous sodium sulfate and concentrated to give a crude product, which was purified by column chromatography to give compound 2-2(18.2g, 59mmol, yield 74%).
b. Compound 2-2(18.2g, 59mmol) was added to ethanol (100g) and dissolved with stirring, sodium hydroxide (2.5g, 62.5mmol) was dissolved in water (20g) and then added to the above solution, stirred at room temperature for 2 hours, neutralized with dilute hydrochloric acid (2.5M), the reaction solution was concentrated, the solid was added to ethanol (300ml), stirred for half an hour, filtered, the filtrate was dried over anhydrous sodium sulfate, and concentrated to give compound 2-3(16.8g, 57.5mmol, yield 96.7%).
c. Compound 2-3(16.8g, 56.8mmol), sodium 1, 1-difluoro-2-hydroxyethanesulfonate (11g, 60mmol), and p-toluenesulfonic acid monohydrate (1.7g, 8.9mmol) were added to toluene (350g), heated under reflux for 18 hours, and cooled to room temperature. The mixture was filtered to give a solid, which was slurried in methyl t-butyl ether, the mixture was filtered, and the oven dried cake was collected to give compound 2-4 as a solid (22g, 48mmol, 84% yield).
d. Under the protection of nitrogen flow, (cyclohexa-1, 5-dienyloxy) -trimethyl-silane (8g, 48mmol) and tetramethylene sulfoxide (5g, 48mmol) are dissolved in chloroform (500g), cooled to-30 ℃, trifluoroacetic anhydride (15.6g, 74mmol) is slowly added over 30 minutes, the reaction is stirred for 30 minutes, 2-4(24g, 46mmol) of saturated aqueous solution is added under stirring, the reaction is stirred for 1 hour, the reaction is brought to room temperature after completion, water and chloroform are separated, the aqueous phase is extracted with chloroform, the chloroform phase is concentrated under vacuum to give the crude product, which is washed with diisopropyl ether to give 2-5(24.6g, 40mmol, 83% yield).
Finally, it should be noted that: although the present invention has been described in detail with reference to the foregoing embodiments, it will be apparent to those skilled in the art that changes may be made in the embodiments and/or equivalents thereof without departing from the spirit and scope of the invention. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (7)
1. A sulfonium sulfonate photo-acid generator synthesized from matrine is characterized in that the structure formula of the photo-acid generator is as follows:
r is fluorine substituted alkyl.
2. The photoacid generator of sulfonium sulfonate salt synthesized from matrine according to claim 1, wherein the photoacid generator comprises:
3. the method for synthesizing the sulfonium sulfonate photo-acid generator synthesized from matrine according to claim 1 or 2, which comprises the following specific synthetic steps:
wherein M is an alkali metal; r1Is an alkane;
the first step is as follows: dissolving 2-3 equivalents of diisopropylamine into a tetrahydrofuran solution, cooling to minus 60-80 ℃, slowly dropwise adding 2-3 equivalents of n-butyllithium tetrahydrofuran solution into the solution, after dropwise adding, stirring and reacting the reaction solution at minus 60-80 ℃ for 20-40 minutes, slowly dropwise adding 1 equivalent of matrine tetrahydrofuran solution into the reaction solution, and after dropwise adding, continuously stirring at minus 60-80 ℃ for 20-40 minutes; then dripping 1.2-2 equivalents of tetrahydrofuran solution of dialkyl carbonate into the reaction solution, stirring for 20-40 minutes at minus 60-80 ℃, naturally heating to room temperature, and continuously stirring for reaction for 3-6 hours; slowly quenching the reaction liquid by using a saturated ammonium chloride aqueous solution, extracting a water phase by using ethyl acetate, combining organic phases, drying the organic phases by using anhydrous sodium sulfate, concentrating to obtain a crude product, and purifying the crude product by using column chromatography to obtain an intermediate I;
the second step is that: adding 1-1.5 equivalents of aqueous solution of inorganic base into 1 equivalent of ethanol solution of the intermediate I, stirring for 1.5-3 hours at room temperature, neutralizing with dilute hydrochloric acid, concentrating the reaction solution, adding ethanol into the solid, stirring, filtering, drying the filtrate with anhydrous sodium sulfate, and concentrating to obtain an intermediate II;
the third step: adding 1 equivalent of the intermediate II, 1-1.2 equivalents of the intermediate III and 0.1-0.2 equivalent of an acid catalyst into toluene, heating and refluxing for 16-20 hours, and cooling to room temperature; filtering the mixture to obtain a solid, adding the solid into methyl tert-butyl ether for pulping, filtering the mixed solution, and collecting and drying a filter cake to obtain an intermediate IV;
the fourth step: under the protection of inert gas, dissolving 1 equivalent of (cyclohexyl-1, 5-dialkenyloxy) -trimethyl-silane and 1 equivalent of tetramethylene sulfoxide in chloroform, cooling to minus 20-minus 40 ℃, slowly adding 1.3-2.0 equivalents of trifluoroacetic anhydride in 30 minutes, stirring for reacting for 20-40 minutes, adding 1 equivalent of saturated aqueous solution of an intermediate III under stirring, stirring for reacting for 0.5-1.5 hours, recovering to room temperature after the reaction is finished, separating water and chloroform, extracting an aqueous phase with chloroform, concentrating a chloroform phase under vacuum to obtain a crude product, and washing the crude product with diisopropyl ether to obtain the light acid generator.
4. The method as claimed in claim 3, wherein the dialkyl carbonate is dimethyl carbonate or diethyl carbonate.
5. The method for synthesizing a sulfonium sulfonate photo-acid generator from matrine according to claim 3 or 4, wherein the inorganic base is sodium hydroxide or potassium hydroxide.
6. The method as claimed in claim 5, wherein the acid catalyst is p-toluenesulfonic acid or sulfuric acid.
7. The method as claimed in claim 6, wherein M is K, Na or Li.
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| CN112661805A (en) * | 2020-12-23 | 2021-04-16 | 上海博栋化学科技有限公司 | Sulfonium salt photo-acid generator synthesized from Bromus buxus alkali B and preparation method thereof |
| WO2023097826A1 (en) * | 2021-11-30 | 2023-06-08 | 上海新阳半导体材料股份有限公司 | Krf light source thick film photoresist composition, preparation method therefor and use method thereof |
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| CN111138405A (en) * | 2019-12-28 | 2020-05-12 | 上海博栋化学科技有限公司 | Sulfonium sulfonate photo-acid generator synthesized from patchouli alcohol and synthesis method thereof |
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| WO2023097826A1 (en) * | 2021-11-30 | 2023-06-08 | 上海新阳半导体材料股份有限公司 | Krf light source thick film photoresist composition, preparation method therefor and use method thereof |
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Application publication date: 20210420 |