CN111116546A - Sulfonium sulfonate photo-acid generator synthesized from beta-eucalyptol and synthesis method thereof - Google Patents
Sulfonium sulfonate photo-acid generator synthesized from beta-eucalyptol and synthesis method thereof Download PDFInfo
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- CN111116546A CN111116546A CN201911384564.9A CN201911384564A CN111116546A CN 111116546 A CN111116546 A CN 111116546A CN 201911384564 A CN201911384564 A CN 201911384564A CN 111116546 A CN111116546 A CN 111116546A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/46—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings substituted on the ring sulfur atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/06—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing halogen atoms, or nitro or nitroso groups bound to the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/07—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton
- C07C309/12—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing esterified hydroxy groups bound to the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/17—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing carboxyl groups bound to the carbon skeleton
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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
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/14—All rings being cycloaliphatic
- C07C2602/26—All rings being cycloaliphatic the ring system containing ten carbon atoms
- C07C2602/28—Hydrogenated naphthalenes
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract
The invention discloses a sulfonium sulfonate photo-acid generator synthesized from beta-eucalyptol and a synthesis method thereof, belonging to the field of chemical synthesis and photoetching materials. The general structural formula of the photoacid generator is as follows:
in the formula, R1Is composed of
And
one of (1); r2Is one of alkyl, cycloalkyl, ester group-containing alkyl and fluorine-containing alkyl. The synthetic method of the photoacid generator comprises the following steps: reacting beta-cineol with a sulfonate compound to obtain an intermediate; and (2) reacting the intermediate with (cyclohexyl-1, 5-dialkenyloxy) -trimethyl-silane, tetramethylene sulfoxide and trifluoroacetic anhydride to obtain the sulfonium sulfonate photo-acid generator. The raw material beta-cineol adopted by the invention has higher molecular weight, and the formed photoacid generator also has higher molecular weight, so that the diffusion of the photoacid generator can be reduced, the improvement of edge roughness is facilitated, the line width roughness is reduced, and the resolution is improved.
Description
Technical Field
The invention relates to the field of chemical synthesis and photoetching materials, in particular to a sulfonium sulfonate photo-acid generator synthesized from beta-eucalyptol 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 photolithography material (particularly 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 lithography technology is not independent of the development of the lithography material, and the development of the lithography material determines the development and application of the lithography technology to a certain extent. The photolithography material (specifically referred to as photoresist), also called photoresist, is the most critical functional chemical material involved in photolithography technology, and its main components are resin, Photo Acid Generator (PAG), and corresponding additives and solvents. The photoacid generator is a photosensitive compound, which decomposes under light irradiation to generate an acid, which can decompose or crosslink the acid-sensitive resin, thereby increasing the dissolution contrast between the irradiated part and the non-irradiated part in a developer, and can be used in the technical field of pattern microfabrication.
With the development of large-scale and ultra-large-scale integrated circuits in recent years, the research, development and application of photoresist are greatly promoted. As the feature size of integrated circuits decreases, the effect of edge roughness becomes more pronounced and the types of photoacid generators are developed. However, the conventional photoacid generator still has a problem of diffusion of acid, and thus edge roughness cannot be reduced.
Disclosure of Invention
An object of an embodiment of the present invention is to provide a sulfonium sulfonate photoacid generator synthesized from beta-eudesmol, so as to solve the problems in the background art.
In order to achieve the above purpose, the embodiments of the present invention provide the following technical solutions:
a sulphonyl sulfonium salt photo-acid generator synthesized from beta-eudesmol has a structural general formula as shown in formula I:
in the formula, R1Is composed of
One of (1); r2Is one of alkyl, cycloalkyl, ester group-containing alkyl and fluorine-containing alkyl.
As a preferred embodiment of the present invention, the structural formula of the sulfonium sulfonate salt photoacid generator is one of formula II, formula III and formula IV:
another object of the embodiments of the present invention is to provide a method for synthesizing the above sulfonium sulfonate photoacid generator, which comprises the following steps:
reacting beta-cineol with a sulfonate compound to obtain an intermediate;
and (2) reacting the intermediate with (cyclohexyl-1, 5-dialkenyloxy) -trimethyl-silane, tetramethylene sulfoxide and trifluoroacetic anhydride to obtain the sulfonium sulfonate photo-acid generator.
As another preferable mode of the embodiment of the present invention, the sulfonate compound is a carboxyl group-containing sulfonate; the method comprises the following steps of reacting beta-cineol with a sulfonate compound to obtain an intermediate, and specifically comprises the following steps:
carrying out esterification reaction on beta-cineol and sulfonate containing carboxyl to obtain an intermediate; the intermediate is sulfonate containing beta-eudesmol ester group.
Wherein R in the formula of the sulfonic sulfonium salt type photoacid generator obtained by the technical scheme1Is composed of
As another preferable mode of the embodiment of the present invention, the sulfonate compound is a hydroxyl group-containing sulfonate; the method comprises the following steps of reacting beta-cineol with a sulfonate compound to obtain an intermediate, and specifically comprises the following steps:
reacting beta-eudesmol with hydroxyl-containing sulfonate to obtain an intermediate; the intermediate is sulfonate containing beta-cineol carbonate group.
Wherein R in the formula of the sulfonic sulfonium salt type photoacid generator obtained by the technical scheme1Is composed of
As another preferable mode of the embodiment of the present invention, the sulfonate compound is a hydroxyl group-containing sulfonate; the method comprises the following steps of reacting beta-cineol with a sulfonate compound to obtain an intermediate, and specifically comprises the following steps:
reacting beta-cineol with ester-group-containing halide to obtain ester-group-containing ether compounds;
hydrolyzing the ester group of the ether compound containing the ester group under an alkaline condition, and adjusting the ester group to be acidic to obtain an ether compound containing a carboxyl group;
carrying out esterification reaction on the ether compound containing carboxyl and sulfonate containing hydroxyl to obtain an intermediate; the intermediate is sulfonate containing ester group.
Wherein R in the formula of the sulfonic sulfonium salt type photoacid generator obtained by the technical scheme1Is composed of
In another preferable embodiment of the present invention, the sulfonate compound is one of a sodium sulfonate compound, a potassium sulfonate compound, and a lithium sulfonate compound.
As another preferable mode of the embodiment of the present invention, p-toluenesulfonic acid is used as a catalyst in the esterification reaction.
As another preferable scheme of the embodiment of the present invention, the step of reacting beta-eudesmol with hydroxyl-containing sulfonate to obtain an intermediate specifically includes:
the beta-cineol and the sulfonate containing hydroxyl are placed in a system containing pyridine and bis (trichloromethyl) carbonate for reaction to obtain an intermediate.
Another objective of the embodiments of the present invention is to provide an application of the above sulfonium sulfonate photoacid generator synthesized from beta-eudesmol in a lithography material.
Compared with the prior art, the embodiment of the invention has the beneficial effects that:
(1) the synthetic raw material beta-eucalyptol adopted by the sulfonium sulfonate photoacid generator provided by the embodiment of the invention has higher molecular weight, and the formed photoacid generator also has higher molecular weight, so that the diffusion of the photoacid generator can be reduced, the improvement of edge roughness is facilitated, the line width roughness is reduced, and the resolution is improved.
(2) The sulfonium sulfonate photoacid generator provided by the embodiment of the invention contains an ester group, so that the lipid solubility of the photoacid generator can be increased, the photoacid generator is more easily dissolved in a solvent, the polarity of the photoacid generator and resin is closer, the resin and the photoacid generator are more uniformly mixed in the solvent, and the formation of more uniform photoresist is facilitated.
(3) The synthetic raw material beta-cineol adopted by the sulfonium sulfonate photoacid generator provided by the embodiment of the invention contains an aliphatic ring, and the aliphatic ring has excellent etching resistance.
(4) The sulfonium sulfonate photoacid generator provided by the embodiment of the invention has a simple synthetic route and is convenient to prepare and generate.
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
This example provides a sulfonium sulfonate photoacid generator synthesized from beta-eucalyptol, the reaction route of the synthesis method of the photoacid generator is as follows:
the method specifically comprises the following steps:
s1, dissolving sodium hydroxide (12.8g, 325mmol) in water (30g) to prepare a solution; adding methyl fluorosulfonyl difluoroacetate (20g, 104mmol) into ice water (50g) to obtain a reaction solution, slowly adding a prepared sodium hydroxide solution into the reaction solution under stirring, stirring the reaction solution in an ice bath (the temperature is controlled to be lower than 10 ℃) for 2.5 hours after the addition is finished, then continuing stirring at room temperature for 1 hour, starting heating until the temperature rises to 95 ℃ within 30 minutes, stirring at 95 ℃ for 3 hours, stopping heating, cooling to room temperature, neutralizing with hydrochloric acid, filtering the reaction solution, collecting a filtrate, adding acetone (800g) into the filtrate, separating out a white solid, filtering, washing a filter cake with acetone (100g), and drying to obtain a compound 1-2(21g, 95.4mmol, the yield is 91.7%).
S2, compound 1-2(21g, 95.4mmol) was added to acetonitrile (350g), p-toluenesulfonic acid monohydrate (27.5g, 145mmol) was added thereto, and the mixture was stirred at room temperature for 30 minutes to obtain a reaction solution, and then the reaction solution was heated to 80 degrees celsius, and after stirring at 80 degrees celsius for 3 hours, the reaction solution was cooled to room temperature, filtered, and the filter cake was dried to obtain compound 1-3(16g, 80.8mmol, yield 84.6%) as a white solid.
S3, adding 1-3(16g, 80.8mmol) and beta-eudesmol (18g, 80.9mmol) into 500g of ethylbenzene, adding p-toluenesulphonic acid monohydrate (23g, 121mmol) to obtain a reaction solution, refluxing the reaction solution for 42 hours, cooling the reaction solution, filtering to obtain a solid, washing the solid with acetonitrile three times, concentrating the mixed acetonitrile solution, adding the concentrated acetonitrile solution into methyl tert-butyl ether for pulping, filtering the mixed solution, and collecting the dried filter cake to obtain 1-4(25g, 62mmol, 77% yield) of the intermediate of the solid.
S4, (cyclohexane-1, 5-dialkenyloxy) -trimethyl-silane (10.5g, 62mmol) and tetramethylene sulfoxide (6.5g, 62mmol) are dissolved in chloroform (500g) under the protection of nitrogen flow and cooled to-30 ℃, then trifluoroacetic anhydride (20g, 95mmol) is slowly added within 30 minutes, after stirring for reaction for 30 minutes, a saturated aqueous solution of the above-mentioned intermediate 1-4(25g, 62mmol) is further added with stirring and stirring for reaction for 1 hour, after the reaction is finished, the temperature is returned to room temperature, water and chloroform are separated, the aqueous phase is extracted with chloroform, the chloroform phase is concentrated under vacuum to obtain a crude product, which is washed with methyl tert-butyl ether and dried to obtain sulfonic sulfonium salt photoacid generator 1-5(28g, 50mmol, yield 80%).
Example 2
This example provides a sulfonium sulfonate photoacid generator synthesized from beta-eucalyptol, the reaction route of the synthesis method of the photoacid generator is as follows:
the method specifically comprises the following steps:
s1, under the protection of nitrogen at 0 ℃, adding pyridine (27g, 341mmol) and bis (trichloromethyl) carbonate (13.5g, 34mmol) into dichloromethane (800g), and slowly adding beta-cineol (30g, 135mmol) under stirring to obtain a reaction solution; next, the reaction solution was left at room temperature and stirred for 3 hours, then 1, 1-difluoro-2-hydroxy-ethanesulfonic acid sodium salt (25g, 136mmol) was added to the reaction solution, stirred for 10 hours, the reaction solution was concentrated under vacuum to give a mixture, the mixture was filtered to give a solid, the solid was washed three times with acetonitrile, the mixed acetonitrile solution was concentrated and added to methyl tert-butyl ether for beating, the above mixture was filtered, and the dried cake was collected to give intermediate 2-2(55g, 127mmol, yield 94.3%) as a solid.
S2, (cyclohexyl-1, 5-dialkenyloxy) -trimethyl-silane (21.5g, 128mmol) and tetramethylene sulfoxide (13.3g, 128mmol) are dissolved in chloroform (800g) under the protection of nitrogen flow and cooled to-30 ℃, trifluoroacetic anhydride (41g, 195mmol) is slowly added within 30 minutes, after stirring for reaction for 30 minutes, a saturated aqueous solution of the above intermediate 2-2(55g, 127mmol) is further added with stirring and stirring for reaction for 1 hour, after the reaction is finished, the temperature is returned to room temperature, water and chloroform are separated, the aqueous phase is extracted with chloroform, the chloroform phase is concentrated under vacuum to obtain a crude product, and after the crude product is washed with methyl tert-butyl ether, the crude product is dried to obtain sulfonic sulfonium salt photoacid generator 2-3(56g, 94mmol, yield 74.3%).
Example 3
This example provides a sulfonium sulfonate photoacid generator synthesized from beta-eucalyptol, the reaction route of the synthesis method of the photoacid generator is as follows:
the method specifically comprises the following steps:
s1, slowly adding sodium hydride (5g, 208mmol) to a mixture of beta-eucalyptol 3-1(30g, 135mmol) and anhydrous tetrahydrofuran (400g) at 0 ℃ under nitrogen, and stirring for 20 minutes; then, ethyl 2-bromo-2-cyclopentylacetate (32g, 136mmol) was added dropwise to the above mixed solution, and stirred for 20 minutes; then, the reaction was carried out by stirring at 25 ℃ for 6 hours, and after completion of the reaction, water was added thereto to quench at 0 ℃. Concentrating the quenched mixed solution by rotary evaporation, extracting with dichloromethane (250g multiplied by 3) for three times, combining the extract, washing with saturated saline solution (200g), drying with anhydrous sodium sulfate, and concentrating by rotary evaporation to obtain a crude product; the crude product was purified by column chromatography to give compound 3-2(48.2g, 128mmol, yield 95%).
S2, adding the compound 3-2(48.2g, 128mmol) and sodium hydroxide (8g, 200mmol) into a mixed solution of water (50g) and methanol (250g), and stirring at 25 ℃ for 24h to obtain a reaction solution; then, concentrating the reaction solution, and adjusting the pH value of the reaction solution to 2 by using hydrochloric acid to obtain a mixed solution; then, the resulting mixture was extracted twice with ethyl acetate (300g × 2), the extracts were combined, washed with saturated brine (200g), dried over anhydrous sodium sulfate, and concentrated by rotary evaporation to obtain compound 3-3(42.7g, 123mmol, yield 95.7%) as a liquid.
S3, compound 3-3(42.7g, 123mmol), 1-difluoro-2-hydroxy-ethanesulfonic acid sodium salt (22.6g, 123mmol) and p-toluenesulfonic acid monohydrate (35g, 184mmol) were added to toluene (700g), and after heating under reflux for 18 hours, cooled to room temperature again to give a mixture. The mixture was then filtered to give a solid, which was washed three times with acetonitrile. The mixed acetonitrile solution was concentrated and added to methyl t-butyl ether for pulping, the above mixture was filtered, and the dried cake was collected to obtain intermediate 3-4(60.3g, 117mmol, yield 95.6%) as a solid.
S4, (cyclohexyl-1, 5-dialkenyloxy) -trimethyl-silane (19.8g, 117mmol) and tetramethylene sulfoxide (12.3g, 118mmol) are dissolved in chloroform (900g) under the protection of nitrogen flow and cooled to-30 ℃, trifluoroacetic anhydride (37g, 176mmol) is slowly added within 30 minutes, after stirring for reaction for 30 minutes, a saturated aqueous solution of the above intermediate 3-4(60.3g, 117mmol) is further added with stirring and stirring for reaction for 1 hour, after the reaction is finished, the temperature is returned to room temperature, water and chloroform are separated, the aqueous phase is extracted with chloroform, the chloroform phase is concentrated under vacuum to obtain a crude product, which is washed with methyl tert-butyl ether and dried to obtain 3-5(58g, 86mmol, yield 73%) of the sulfonate sulfonium salt photoacid generator.
In light of the foregoing description of the preferred embodiment of the present invention, many modifications and variations will be apparent to those skilled in the art without departing from the spirit and scope of the invention. The technical scope of the present invention is not limited to the content of the specification, and must be determined according to the scope of the claims.
Claims (10)
1. The sulfonium sulfonate photoacid generator synthesized from beta-eucalyptol is characterized by having a general structural formula as shown in formula I:
in the formula, R1Is composed of
One of (1); r2Is one of alkyl, cycloalkyl, ester group-containing alkyl and fluorine-containing alkyl.
2. The sulfonium sulfonate photoacid generator synthesized from beta-eucalyptol as claimed in claim 1, wherein the sulfonium sulfonate photoacid generator has a structure of one of formula II, formula III and formula IV:
3. a method for synthesizing a sulfonium sulfonate photoacid generator synthesized from beta-eucalyptol as claimed in any of claims 1-2, comprising the steps of:
reacting beta-cineol with a sulfonate compound to obtain an intermediate;
and (2) reacting the intermediate with (cyclohexyl-1, 5-dialkenyloxy) -trimethyl-silane, tetramethylene sulfoxide and trifluoroacetic anhydride to obtain the sulfonium sulfonate photo-acid generator.
4. The method as claimed in claim 3, wherein the sulfonate compound is a carboxyl group-containing sulfonate; the method comprises the following steps of reacting beta-cineol with a sulfonate compound to obtain an intermediate, and specifically comprises the following steps:
carrying out esterification reaction on beta-cineol and sulfonate containing carboxyl to obtain an intermediate; the intermediate is sulfonate containing beta-eudesmol ester group.
5. The method as claimed in claim 3, wherein the sulfonate compound is a hydroxyl group-containing sulfonate; the method comprises the following steps of reacting beta-cineol with a sulfonate compound to obtain an intermediate, and specifically comprises the following steps:
reacting beta-eudesmol with hydroxyl-containing sulfonate to obtain an intermediate; the intermediate is sulfonate containing beta-cineol carbonate group.
6. The method as claimed in claim 3, wherein the sulfonate compound is a hydroxyl group-containing sulfonate; the method comprises the following steps of reacting beta-cineol with a sulfonate compound to obtain an intermediate, and specifically comprises the following steps:
reacting beta-cineol with ester-group-containing halide to obtain ester-group-containing ether compounds;
hydrolyzing the ester group of the ether compound containing the ester group under an alkaline condition, and adjusting the ester group to be acidic to obtain an ether compound containing a carboxyl group;
carrying out esterification reaction on the ether compound containing carboxyl and sulfonate containing hydroxyl to obtain an intermediate; the intermediate is sulfonate containing ester group.
7. The method as claimed in any one of claims 4 to 6, wherein the sulfonate compound is one of a sodium sulfonate compound, a potassium sulfonate compound and a lithium sulfonate compound.
8. The method as claimed in claim 4 or 6, wherein p-toluenesulfonic acid is used as a catalyst in the esterification reaction.
9. The method as claimed in claim 5, wherein the step of reacting beta-cineol with hydroxyl group-containing sulfonate to obtain intermediate comprises:
the beta-cineol and the sulfonate containing hydroxyl are placed in a system containing pyridine and bis (trichloromethyl) carbonate for reaction to obtain an intermediate.
10. Use of the sulfonium sulfonate photoacid generator synthesized from beta-eucalyptol as claimed in any of claims 1-2 in photolithography materials.
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| CN112645951A (en) * | 2020-12-23 | 2021-04-13 | 上海博栋化学科技有限公司 | Sulfonium sulfonate photo-acid generator synthesized from vinblastine and synthetic method thereof |
| CN112645849A (en) * | 2020-12-23 | 2021-04-13 | 上海博栋化学科技有限公司 | Sulfonium sulfonate photo-acid generator synthesized from abietic acid and synthetic method thereof |
| 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 |
| CN112679499A (en) * | 2020-12-23 | 2021-04-20 | 上海博栋化学科技有限公司 | Sulfonium sulfonate photo-acid generator synthesized from matrine and synthesis method thereof |
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Application publication date: 20200508 |