CN111116426A - Sulfonium salt photo-acid generator containing patchouli alcohol structure and preparation method thereof - Google Patents
Sulfonium salt photo-acid generator containing patchouli alcohol structure and preparation method thereof Download PDFInfo
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- CN111116426A CN111116426A CN201911372620.7A CN201911372620A CN111116426A CN 111116426 A CN111116426 A CN 111116426A CN 201911372620 A CN201911372620 A CN 201911372620A CN 111116426 A CN111116426 A CN 111116426A
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- patchouli alcohol
- alcohol structure
- sulfonium salt
- sulfonium
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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
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
-
- 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
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
Abstract
The invention relates to the technical field of photoresist, and particularly discloses a sulfonium salt photo-acid generator containing a patchouli alcohol 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 an optionally substituted alkyl group having 1 to 12 carbon atoms. The photoacid generator prepared by the present invention has good hydrophilicityCan improve the solubility in organic solvents and effectively inhibit the diffusion of acid. The invention also provides a preparation method of the sulfonium salt photoacid generator containing the patchouli alcohol structure, which is characterized in that the patchouli alcohol is used as a reaction initiator to react with sulfonium halide to obtain the sulfonium salt photoacid generator containing the patchouli alcohol 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 a patchouli alcohol 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 photoacid generator containing a patchouli alcohol structure and a preparation method thereof, so as to solve the problem that the existing onium salt photoacid generator in the background art still has acid diffusion.
In order to achieve the purpose, the invention provides the following technical scheme:
a sulfonium salt photo-acid generator containing a patchouli alcohol structure comprises an anion and a 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.
Preferably, the methylene group of the alkyl, cycloalkyl, heteroalkyl, or heterocycloalkyl group may be substituted with an ester group, a carbonate group, and a difluoromethylene group.
As a further scheme of the invention: the anion comprises any one of the following structural formulas:
the preparation method of the sulfonium salt photoacid generator containing the patchouli alcohol structure comprises the following steps:
sulfonic group is introduced by taking patchouli alcohol as a reaction initiator through reaction to obtain a sulfonate compound containing a patchouli alcohol structure;
and carrying out ion exchange reaction on the sulfonate compound containing the patchouli alcohol structure and halogenated sulfonium, and sequentially recrystallizing, filtering and drying reaction liquid to obtain the sulfonium salt photo-acid generator containing the patchouli alcohol structure.
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:
1) the sulfonium salt photoacid generator containing the patchouli alcohol structure has good hydrophilic-lipophilic balance, improves the solubility in an organic solvent while having good hydrophilicity, has low diffusivity, solves the problem that the existing onium salt photoacid generator still has acid diffusion, can reduce the edge roughness and improve the resolution.
2) The photoacid generator provided by the invention contains a patchouli alcohol structure, further, anions comprise the patchouli alcohol structure and an ester group structure, the molecular weight of the patchouli alcohol is 222.37, the molecular weight is larger, the diffusion of the photoacid generator can be inhibited, and the edge roughness of the photoresist is reduced; the ester group structure can increase the lipid solubility of the photoacid generator in resin and solvent to form photoresist which is dissolved uniformly, is favorable for imaging, and enables the photoacid generator to have certain hydrophilicity and to be well adhered on a silicon wafer.
3) The synthesis process is simple, the operation is convenient, and meanwhile, the patchouli alcohol is used as a raw material and a green natural product, 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 containing patchouli alcohol structure comprises the following specific synthetic steps:
1) patchouli alcohol 1-1(0.225mol, 50g), sodium difluorosulfoacetate (0.227mol, 45g) and p-toluenesulfonic acid monohydrate (0.026mol, 5g) were added to toluene (500g), heated at reflux for 18 hours and cooled to room temperature to give a mixture; filtering the mixture to obtain a solid, said solid being washed three times with acetonitrile; and concentrating the mixed acetonitrile solution, adding the concentrated acetonitrile solution into methyl tert-butyl ether for pulping, filtering the mixed solution, collecting and drying a filter cake to obtain 1-2(0.162mol, 65g, yield 71.8%) of the sulfonate compound containing the patchouli alcohol structure.
2) Dissolving the sulfonate compound 1-2(0.159mol, 60g) containing the patchouli alcohol structure obtained in the step 1) and triphenyl sulfonium bromide (0.151mol, 52g) in a mixed solvent of dichloromethane (300g) and water (300 g); the mixture was stirred at 30 ℃ for 24 hours; the reaction solution was washed with deionized water (200g × 4), and the organic solvent was evaporated to dryness, after which the obtained residue was dissolved in dichloromethane and added to methyl tert-butyl ether for recrystallization; the recrystallized solid was vacuum filtered, washed with methyl t-butyl ether and vacuum dried to give an off-white solid (0.140mol, 90g, yield 93.9%) as 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 containing patchouli alcohol structure comprises the following specific synthetic steps:
1) patchouli alcohol 2-1(0.225mol, 50g), 2-sulfoacetate sodium salt (0.228mol, 37g) and p-toluenesulfonic acid monohydrate (0.026mol, 5g) were added to toluene (500g), heated to reflux for 18 hours and cooled to room temperature; the mixture was filtered to give a solid, which was washed three times with acetonitrile; and concentrating the mixed acetonitrile solution, adding the concentrated acetonitrile solution into methyl tert-butyl ether for pulping, filtering the mixed solution, collecting and drying a filter cake to obtain the sulfonate compound 2-2(0.172mol, 63g and 76.5%) containing the patchouli alcohol structure.
2) Dissolving the sulfonate compound 2-2(0.163mol, 60g) containing the patchouli alcohol structure obtained in the step 1) and tris (4-methylphenyl) sulfonium chloride (0.164mol, 56g) in a mixed solvent of dichloromethane (400g) and water (400 g); the mixture was stirred at 30 ℃ for 24 hours; the reaction solution was washed with deionized water (200g × 4), and the organic solvent was evaporated to dryness, after which the obtained residue was dissolved in dichloromethane and added to methyl tert-butyl ether for recrystallization; the recrystallized solid was vacuum filtered, washed with methyl t-butyl ether and vacuum dried to give an off-white solid (0.154mol, 100g, yield 94.1%) as photoacid generator 2-3.
Specifically, the synthetic route from step 1) to step 2) is as follows:
example 3
A sulfonium salt photo-acid generator 3-3 containing patchouli alcohol structure comprises the following specific synthetic steps:
1) pyridine (0.569mol, 45g) and bis (trichloromethyl) carbonate (0.078mol, 23g) were added to dichloromethane (2000g) under nitrogen protection at 0 ℃ and stirred, followed by slow addition of patchouli alcohol 3-1(0.225mol, 50 g); the reaction mixture was stirred at 25 ℃ for 3 hours; then 1, 1-difluoro-2-hydroxy-ethanesulfonic acid sodium salt (0.228mol, 89g) was added to the reaction solution, and stirred for 10 hours; concentrating by rotary evaporation to obtain a mixture, filtering the mixture to obtain a solid, and washing the solid with acetonitrile for three times; and concentrating the mixed acetonitrile solution, adding the concentrated acetonitrile solution into methyl tert-butyl ether for pulping, filtering the mixture, collecting a dried filter cake, and obtaining the sulfonate compound 3-2 containing the patchouli alcohol structure (0.162mol, 70g, yield 72.0%).
2) Dissolving the sulfonate compound 3-2(0.139mol, 60g) containing the patchouli alcohol structure obtained in the step 1) and triphenyl sulfonium chloride (0.141mol, 42g) in a mixed solvent of dichloromethane (300g) and water (300 g); the mixture was stirred at 30 ℃ for 4 hours; the reaction solution was washed with deionized water (200g × 4), and the organic solvent was evaporated to dryness, after which the obtained residue was dissolved in dichloromethane and added to methyl tert-butyl ether for recrystallization; the recrystallized solid was vacuum filtered, washed with methyl t-butyl ether and vacuum dried to give an off-white solid (0.126mol, 85g, yield 91.1%) as photoacid generator 3-3.
Specifically, the synthetic route from step 1) to step 2) is as follows:
example 4
A sulfonium salt photo-acid generator 4-5 containing patchouli alcohol structure comprises the following specific synthetic steps:
1) slowly adding sodium hydride (0.333mol, 8g) into a mixture of patchouli alcohol 4-1(0.225mol, 50g) and tetrahydrofuran (600g) at 0 ℃ under nitrogen, and stirring for 20 minutes; then, 2-bromo-2-cyclopentyl ethyl acetate (0.225mol, 53g) was added dropwise to the above mixed solution, and stirred for 20 minutes; then mixing and stirring for 6 hours at 25 ℃; after the reaction is finished, adding water for quenching at 0 ℃; the quenched mixture was concentrated by rotary evaporation and extracted with dichloromethane (200g × 3); mixing the extractive solutions, washing with saturated saline (500g), drying with anhydrous sodium sulfate, and concentrating by rotary evaporation to obtain crude product; the crude product was purified by column chromatography to give the first liquid compound 4-2(0.181mol, 68g, yield 80.3%).
2) Adding the first liquid compound 4-2(0.159mol, 60g) obtained in step 1) and sodium hydroxide (0.25mol, 10g) to a mixed solution of water (50g) and methanol (400g), and stirring at 25 ℃ for 24 hours; concentrating the reaction solution, and adjusting the pH value of the solution to 2 by using hydrochloric acid to obtain a mixed solution; the resulting mixture was extracted with ethyl acetate (500g × 2), the combined extracts were washed with saturated brine (1000g), dried over anhydrous sodium sulfate, and concentrated by rotary evaporation to give a second liquid compound 4-3(0.152mol, 53g, yield 95.4%).
3) Adding the second liquid compound 4-3(0.143mol, 50g) obtained in step 2), 1-difluoro-2-hydroxy-ethanesulfonic acid sodium salt (0.147mol, 27g) and p-toluenesulfonic acid monohydrate (0.026mol, 5g) to toluene (450g), heating under reflux for 18 hours and cooling to room temperature; the mixture was 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-mentioned mixed solution was filtered, and the filter cake was collected and dried to obtain a first solid compound 4-4(0.117mol, 60g, yield 81.3%).
4) Dissolving the first solid compound 4-4(0.107mol, 55g) and tris (4-methylphenyl) sulfonium bromide (0.106mol, 41g) obtained in step 3) in a mixed solvent of dichloromethane (300g) and water (300 g); the mixture was stirred at 30 ℃ for 24 hours; the reaction solution was washed with deionized water (200g × 4), and the organic solvent was evaporated to dryness, after which the obtained residue was dissolved in dichloromethane and added to methyl tert-butyl ether for recrystallization; the recrystallized solid was vacuum filtered, washed with methyl t-butyl ether and vacuum dried to give an off-white solid (0.100mol, 80g, yield 93.9%) as photoacid generator 4-5.
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 a patchouli alcohol structure is characterized by comprising an anion and a 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 sulfonium salt-based photoacid generator having a patchouli alcohol structure according to claim 1, wherein a methylene group in the alkyl group, cycloalkyl group, heteroalkyl group or heterocycloalkyl group may be substituted with an ester group, a carbonate group and a difluoromethylene group.
3. The sulfonium salt photoacid generator containing a patchouli alcohol structure of claim 1, wherein the anion comprises any of the following structural formulas:
4. a method for preparing the sulfonium salt type photoacid generator containing a patchouli alcohol structure as claimed in any one of claims 1 to 3, comprising the steps of:
sulfonic group is introduced by taking patchouli alcohol as a reaction initiator through reaction to obtain a sulfonate compound containing a patchouli alcohol structure;
and carrying out ion exchange reaction on the sulfonate compound containing the patchouli alcohol structure and halogenated sulfonium, and sequentially recrystallizing, filtering and drying reaction liquid to obtain the sulfonium salt photo-acid generator containing the patchouli alcohol structure.
5. The method for preparing the sulfonium salt photoacid generator having a patchouli alcohol structure as claimed in claim 4, 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 (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| 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 |
| 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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| Publication number | Priority date | Publication date | Assignee | Title |
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| 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 |
| 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 |
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| 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: 20200508 |