CN111138331A - Sulfonium salt photo-acid generator containing β -eucalyptol structure and preparation method thereof - Google Patents
Sulfonium salt photo-acid generator containing β -eucalyptol structure and preparation method thereof Download PDFInfo
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- CN111138331A CN111138331A CN201911372791.XA CN201911372791A CN111138331A CN 111138331 A CN111138331 A CN 111138331A CN 201911372791 A CN201911372791 A CN 201911372791A CN 111138331 A CN111138331 A CN 111138331A
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- eucalyptol
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
- C07C381/12—Sulfonium compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
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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
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- 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
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Materials For Photolithography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to the technical field of photoresist, and particularly discloses a sulfonium salt photo-acid generator containing an β -eucalyptol structure and a preparation method thereof, wherein the photo-acid generator comprises anions and cations, and the anions and the cations respectively have the following structures:
wherein R represents alkyl, cycloalkyl, heteroalkyl or heterocycloalkyl, P1、P2And P3Each independently represents a hydrogen atom or has 1 to 1The photoacid generator prepared by the invention has good hydrophilicity, can improve the solubility in an organic solvent, and can effectively inhibit the diffusion of acid, and the invention also provides a preparation method of the sulfonium salt photoacid generator containing β -eucalyptol structure, wherein β -eucalyptol is used as a reaction initiator to react with sulfonium halide to obtain the sulfonium salt photoacid generator containing β -eucalyptol structure, and the preparation method is simple.
Description
Technical Field
The invention relates to the technical field of photoresist, in particular to a sulfonium salt photo-acid generator containing β -eucalyptol structure and a preparation method thereof.
Background
The photoacid generator is also called as photoacid generator, is a light-sensitive compound, is decomposed under illumination to generate acid, and the generated acid can enable acid-sensitive resin to generate decomposition or crosslinking reaction, so that the dissolution contrast of an illuminated part and a non-illuminated part in a developing solution is increased, and the photoacid generator can be used in the technical field of pattern micro-processing.
Among them, photoacid generators are widely used in imaging systems such as chemically amplified resists (also known as photoresists). Commonly used photoacid generators include diazonium salt compounds, onium salt compounds, nitrogen hydroxysulfonate compounds, and the like. Among them, onium salt compounds are very important photoacid generating systems. Currently, sulfonium salts and iodonium salts are important. The sulfonium salt and the iodonium salt have low production cost and mature process and are commercialized in large batch. Because the onium salt photo-acid generator counter anion is super strong base anion, the proton acid generated after photolysis is super strong acid, and the method is stable, non-volatile, small in diffusion range and widely applicable to chemical amplification resists.
The chemically amplified resist is widely applied to integrated circuits, and the development of large-scale and super-large-scale integrated circuits in recent years greatly promotes the research, development and application of photoresist, and along with the gradual reduction of the feature size of the integrated circuits, the influence of edge roughness is more and more obvious, and the type of the photoacid generator is also developed forward. However, the conventional onium salt type photoacid generators still have a problem of diffusion of acid, and thus edge roughness cannot be reduced.
Disclosure of Invention
The invention aims to provide a sulfonium salt photo-acid generator containing β -eucalyptol structure, which aims to solve the problem of acid diffusion of the existing onium salt photo-acid generators proposed in the background art.
In order to achieve the purpose, the invention provides the following technical scheme:
a sulfonium salt photo-acid generator containing β -eucalyptol structure comprises anion and cation, wherein the structure of the anion is shown as the following formula:
R represents alkyl, cycloalkyl, heteroalkyl or heterocycloalkyl; and the methylene group in the alkyl, cycloalkyl, heteroalkyl, or heterocycloalkyl group may be substituted with an ester group, a carbonate group, and a difluoromethylene group.
The structure of the cation is shown as the following formula:
P1、P2And P3Each independently represents a hydrogen atom or an optionally substituted alkyl group having 1 to 12 carbon atoms.
As a further scheme of the invention: the anion comprises any one of the following structural formulas:
the preparation method of the sulfonium salt photo-acid generator containing the β -eucalyptol structure comprises the following steps:
β -cineol is used as a reaction initiator, and sulfonic acid groups are introduced through reaction to obtain a sulfonate compound containing β -cineol structure;
and (2) carrying out ion exchange reaction on the β -eucalyptol structure-containing sulfonate compound and sulfonium halide, and sequentially recrystallizing, filtering and drying reaction liquid to obtain the photoacid generator, wherein preferably, the molar ratio of the β -eucalyptol structure-containing sulfonate compound to the sulfonium halide is 0.9-1.0: 0.9-1.0.
As a still further aspect of the present invention, the structure of said β -eudesmol is represented by the following formula:
as a still further scheme of the invention: the sulfonium halide is any one of triphenylsulfonium bromide, triphenylsulfonium chloride, tris (4-methylphenyl) sulfonium chloride or tris (4-methylphenyl) sulfonium bromide.
Compared with the prior art, the invention has the beneficial effects that:
the prepared sulfonium salt photoacid generator containing β -eucalyptol structure has good hydrophilic-lipophilic balance and low diffusivity, anions in the photoacid generator comprise β -eucalyptol structure and ester group structure, the β -eucalyptol has large molecular weight, the diffusion of photoacid generator substances can be inhibited, and the edge roughness of photoresist is reduced, the ester group structure can increase the lipid solubility of the photoacid generator in resin and solvent, form uniformly dissolved photoresist, is favorable for imaging, ensure that the photoacid generator has certain hydrophilicity, can be well adhered to a silicon wafer, namely the photoacid generator has good hydrophilicity and improves the solubility in an organic solvent, solves the problem that the existing onium salt photoacid generator still has acid diffusion, and can reduce the edge roughness, thereby improving the resolution.
The synthesis process is simple, convenient to operate and few in synthesis steps, and meanwhile, the trumpet-shaped tea alcohol is used as the raw material, and the β -cineol is a green natural product, so that the synthesis process is pollution-free, simple and easy to obtain, and has wide market prospect.
Detailed Description
The present invention will be described in further detail with reference to specific examples. The following examples will assist those skilled in the art in further understanding the invention, but are not intended to limit the invention in any way. It should be noted that variations and modifications can be made by persons skilled in the art without departing from the spirit of the invention. All falling within the scope of the present invention.
Example 1
A sulfonium salt photo-acid generator 1-3 comprises the following specific synthetic steps:
1) a mixture of β -eucalyptol 1-1(45.0mmol, 10g), p-methoxyphenol (0.8mmol, 0.1g), sodium difluorosulfoacetate (44.9mmol, 8.9g) and p-toluenesulfonic acid monohydrate (5.2mmol, 1g) was heated under reflux in toluene (150g) for 18 hours and cooled to room temperature, the mixture was filtered, the solid was washed three times with acetonitrile, the mixed acetonitrile solution was then concentrated and slurried in methyl t-butyl ether, the dried cake was filtered and collected to give compound 1-2(38.8mmol, 15.6g, 86.2% yield) as a sulfonate containing β -eucalyptol structure in solid form.
2) Dissolving the β -eucalyptol structure-containing sulfonate compound 1-2(37.3mmol, 15g) and triphenylsulfonium bromide (37.3mmol, 12.8g) obtained in the step 1) in a mixed solvent of dichloromethane (100g) and water (100g), stirring the mixture at 30 ℃ for 24 hours, washing a reaction solution with deionized water (50g multiplied by 4), evaporating an organic solvent, dissolving the obtained residue in dichloromethane (50g), adding the dichloromethane (100g) into methyl tert-butyl ether, recrystallizing, carrying out vacuum filtration on crystallized solid, washing with methyl tert-butyl ether, and carrying out vacuum drying to obtain a white-like solid (34.8mmol, 22.4g, the yield is 93.5%), wherein the white-like solid is a photoacid generator 1-3.
Specifically, the synthetic route from step 1) to step 2) is as follows:
example 2
A sulfonium salt photo-acid generator 2-3 is specifically synthesized by the following steps:
1) a mixture of β -eucalyptol 2-1(45.0mmol, 10g), p-methoxyphenol (0.8mmol, 0.1g), 2-sulfoacetate sodium salt (45.0mmol, 7.3g), p-toluenesulfonic acid monohydrate (5.2mmol, 1g) was heated under reflux in toluene (150g) for 18 hours and cooled to room temperature, the mixture was filtered, the solid was washed three times with acetonitrile, then the mixed acetonitrile solution was concentrated and added to methyl t-butyl ether for pulping, the dried cake was filtered and collected to give compound 2-2(39.0mol, 14.3g, 86.8%) as a sulfonate containing β -eucalyptol structure in solid form.
2) Dissolving the β -eucalyptol structure-containing sulfonate compound 2-2(38.2mmol, 14g) and tris (4-methylphenyl) sulfonium chloride (38.4mmol, 13.1g) obtained in the step 1) in a mixed solvent of dichloromethane (100g) and water (100g), stirring the mixture at 30 ℃ for 24 hours, washing a reaction solution by deionized water (50g multiplied by 4), evaporating an organic solvent, dissolving the obtained residue in dichloromethane (50g), adding the dichloromethane to methyl tert-butyl ether (100g), recrystallizing, carrying out vacuum filtration on the crystallized solid, washing by methyl tert-butyl ether, and carrying out vacuum drying to obtain a white-like solid (35.4mmol, 23g, the yield is 92.8%), wherein the white-like solid is a photoacid generator 2-3.
Specifically, the synthetic route from step 1) to step 2) is as follows:
example 3
3-3 of a sulfonium salt photo-acid generator, which comprises the following specific synthetic steps:
1) pyridine (113.8mmol, 9g) and bis (trichloromethyl) carbonate (15.2mmol, 4.5g) are added into dichloromethane (200g) under the protection of nitrogen at 0 ℃ and stirred, then β -eucalyptol 3-1(45.0mmol, 30g) is slowly added, the reaction liquid is stirred for 3 hours at 25 ℃, then 1, 1-difluoro-2-hydroxy-ethanesulfonic acid sodium salt (45.1mmol, 8.3g) is added into the reaction liquid and stirred for 10 hours, rotary evaporation concentration is carried out to obtain a mixture, the mixture is filtered, solid is washed three times by acetonitrile, then the mixed acetonitrile solution is concentrated and added into methyl tert-butyl ether for pulping, and the filter cake is filtered and collected, and dried to obtain solid sulfonate compound 3-2(34.7mmol, 15g, yield 77.1%) containing β -eucalyptol structure.
2) Dissolving the β -eudesmol structure-containing sulfonate compound 3-2(34.7mmol, 15g) and triphenyl sulfonium chloride (34.8mmol, 10.4g) obtained in the step 1) in a mixed solvent of dichloromethane (100g) and water (100g), stirring the mixture at 30 ℃ for 4 hours, washing a reaction solution with deionized water (50g multiplied by 4), evaporating the organic solvent to dryness, dissolving the obtained residue in dichloromethane (50g), adding the dichloromethane (100g) into methyl tert-butyl ether (100g), recrystallizing, carrying out vacuum filtration on the crystallized solid, washing with methyl tert-butyl ether, and carrying out vacuum drying to obtain a white-like solid (32.4mmol, 21.8g, the yield is 93.4%) which is 3-3 percent of the photoacid generator.
Specifically, the synthetic route from step 1) to step 2) is as follows:
example 4
A sulfonium salt photo-acid generator 4-5 is specifically synthesized by the following steps:
1) slowly adding sodium hydride (70.8mmol, 1.7g) into a mixed solution of β -eucalyptol 4-1(45.0mmol, 10g) and tetrahydrofuran (200g) at 0 ℃ under nitrogen, stirring for 20 minutes, then dropwise adding 2-bromo-2-cyclopentyl ethyl acetate (45.1mmol, 10.6g) into the mixed solution, stirring for 20 minutes, then mixing and stirring for 6 hours at 25 ℃, adding water into the reaction solution at 0 ℃ after the reaction is finished, quenching the quenched mixed solution, carrying out rotary evaporation and concentration, extracting with dichloromethane (200g multiplied by 3), combining the extracts, washing with saturated saline (500g), drying with anhydrous sodium sulfate, carrying out rotary evaporation and concentration to obtain a crude product, and carrying out column chromatography purification on the crude product to obtain a first liquid compound 4-2(34.5mmol, 13g, yield 76.8%).
2) Adding the first liquid compound 4-2(34.5mmol, 13g) obtained in step 1) and sodium hydroxide (52.5mmol, 2.1g) to a mixture of water (10g) and methanol (100g), and stirring at 25 ℃ for 24 h; concentrating the reaction solution, and adjusting the pH value of the solution (3mol/L) to 2 by using hydrochloric acid to obtain a mixed solution; the resulting mixture was extracted with ethyl acetate (300g × 2), the combined extracts were washed with saturated brine (500g), dried over anhydrous sodium sulfate, and concentrated by rotary evaporation to give a second liquid compound 4-3(33.6mmol, 11.7g, yield 97.2%).
3) Heating a mixture of the second liquid compound 4-3(31.6mmol, 11g) obtained in step 2), p-methoxyphenol (0.8mmol, 0.1g), 1, 1-difluoro-2-hydroxy-ethanesulfonic acid sodium salt (32.0mmol, 5.9g) and p-toluenesulfonic acid monohydrate (5.7mmol, 1.1g) in toluene (150g) under reflux for 18 h and cooling to room temperature; the mixture was filtered and the solid was washed three times with acetonitrile; the mixed acetonitrile solution was then concentrated and added to methyl t-butyl ether for slurrying, filtration and collection of the dried cake to give the first solid compound 4-4(24.3mmol, 12.5g, 77.0% yield).
4) Dissolving the first solid compound 4-4(23.3mmol, 12g) and tris (4-methylphenyl) sulfonium bromide (23.4mmol, 9g) obtained in step 3) in a mixed solvent of dichloromethane (60g) and water (60 g); the mixture was stirred at 30 ℃ for 24 hours; the reaction solution was washed with deionized water (50g × 4), and the organic solvent was evaporated to dryness, after which the obtained residue was dissolved in methylene chloride (50g), and then added to methyl t-butyl ether (100g) to conduct recrystallization; the crystallized solid was vacuum filtered, washed with methyl tert-butyl ether and vacuum dried to give an off-white solid (21.3mmol, 17g, 91.5% yield) which was 4-5% of the photoacid generator.
Specifically, the synthetic route from step 1) to step 4) is as follows:
while the preferred embodiments of the present invention have been described in detail, the present invention is not limited to the above embodiments, and various changes can be made without departing from the spirit of the present invention within the knowledge of those skilled in the art. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications of the invention may be made without departing from the scope of the invention.
Claims (5)
1. A sulfonium salt photo-acid generator containing β -eucalyptol structure, which is characterized in that the photo-acid generator comprises anion and cation, wherein the structure of the anion is shown as the following formula:
R represents alkyl, cycloalkyl, heteroalkyl or heterocycloalkyl;
the structure of the cation is shown as the following formula:
P1、P2And P3Each independently represents a hydrogen atom or an optionally substituted alkyl group having 1 to 12 carbon atoms.
2. The photoacid generator of a sulfonium salt type containing β -eucalyptol structure as claimed in claim 1, wherein said anion comprises any one of the following structural formulas:
3. a method for producing a photoacid generator of the sulfonium salt type containing β -eucalyptol structure as defined in any of claims 1-2, comprising the steps of:
β -cineol is used as a reaction initiator, and sulfonic acid groups are introduced through reaction to obtain a sulfonate compound containing β -cineol structure;
and (3) carrying out ion exchange reaction on the β -eucalyptol structure-containing sulfonate compound and sulfonium halide, and sequentially recrystallizing, filtering and drying reaction liquid to obtain the photoacid generator.
4. The method for preparing a sulfonium salt photoacid generator containing β -cineol structure as claimed in claim 3, wherein the structure of β -cineol is represented by the following formula:
5. the method for producing a sulfonium salt photoacid generator containing an β -eucalyptol structure as claimed in claim 3, wherein the sulfonium halide is any one of triphenylsulfonium bromide, triphenylsulfonium chloride, tris (4-methylphenyl) sulfonium chloride or tris (4-methylphenyl) sulfonium bromide.
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112114495A (en) * | 2020-10-23 | 2020-12-22 | 华衍化学(上海)有限公司 | Fluorine-free photoacid generator and preparation method thereof |
| CN112552298A (en) * | 2020-12-23 | 2021-03-26 | 上海博栋化学科技有限公司 | Sulfonium salt photo-acid generator synthesized from 16-epi-NB-methyl Voacarpine base and preparation method thereof |
| CN112631072A (en) * | 2020-12-23 | 2021-04-09 | 上海博栋化学科技有限公司 | Sulfonium salt photo-acid generator synthesized from 10-hydroxy climbing mountain orange alkali and preparation 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 |
| CN112661755A (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 isocorynanthine and preparation method thereof |
| CN112661756A (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 20-hydroxyduraline and preparation method thereof |
| CN112679514A (en) * | 2020-12-23 | 2021-04-20 | 上海博栋化学科技有限公司 | Sulfonium salt photo-acid generator synthesized from papaya alkali and preparation method thereof |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112114495A (en) * | 2020-10-23 | 2020-12-22 | 华衍化学(上海)有限公司 | Fluorine-free photoacid generator and preparation method thereof |
| CN112552298A (en) * | 2020-12-23 | 2021-03-26 | 上海博栋化学科技有限公司 | Sulfonium salt photo-acid generator synthesized from 16-epi-NB-methyl Voacarpine base and preparation method thereof |
| CN112631072A (en) * | 2020-12-23 | 2021-04-09 | 上海博栋化学科技有限公司 | Sulfonium salt photo-acid generator synthesized from 10-hydroxy climbing mountain orange alkali and preparation 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 |
| CN112661755A (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 isocorynanthine and preparation method thereof |
| CN112661756A (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 20-hydroxyduraline and preparation method thereof |
| CN112679514A (en) * | 2020-12-23 | 2021-04-20 | 上海博栋化学科技有限公司 | Sulfonium salt photo-acid generator synthesized from papaya alkali and preparation method thereof |
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Application publication date: 20200512 |