CN112661756A - Sulfonium salt photo-acid generator synthesized from 20-hydroxyduraline and preparation method thereof - Google Patents
Sulfonium salt photo-acid generator synthesized from 20-hydroxyduraline and preparation method thereof Download PDFInfo
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- CN112661756A CN112661756A CN202011548531.6A CN202011548531A CN112661756A CN 112661756 A CN112661756 A CN 112661756A CN 202011548531 A CN202011548531 A CN 202011548531A CN 112661756 A CN112661756 A CN 112661756A
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- hydroxyduraline
- sulfonium salt
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- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 239000002253 acid Substances 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 7
- 239000011737 fluorine Substances 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 7
- -1 sulfoacetate compound Chemical class 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 6
- 125000000542 sulfonic acid group Chemical group 0.000 claims abstract description 5
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000003054 catalyst Substances 0.000 claims abstract description 3
- 239000012295 chemical reaction liquid Substances 0.000 claims abstract description 3
- 238000005342 ion exchange Methods 0.000 claims abstract description 3
- 125000005647 linker group Chemical group 0.000 claims abstract description 3
- 239000002585 base Substances 0.000 claims description 14
- 125000004185 ester group Chemical group 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 125000005587 carbonate group Chemical group 0.000 claims description 4
- LZKVGVXWGQWLAI-UHFFFAOYSA-M sodium;1,1-difluoro-2-hydroxyethanesulfonate Chemical compound [Na+].OCC(F)(F)S([O-])(=O)=O LZKVGVXWGQWLAI-UHFFFAOYSA-M 0.000 claims description 4
- XSQIGJCTPAJWQT-UHFFFAOYSA-M sodium;1,1-difluoro-2-hydroxy-2-oxoethanesulfonate Chemical compound [Na+].OS(=O)(=O)C(F)(F)C([O-])=O XSQIGJCTPAJWQT-UHFFFAOYSA-M 0.000 claims description 3
- SMKZBQZAMSKHNS-UHFFFAOYSA-M sodium;2-sulfoacetate Chemical compound [Na+].OS(=O)(=O)CC([O-])=O SMKZBQZAMSKHNS-UHFFFAOYSA-M 0.000 claims description 3
- WLXGQMVCYPUOLM-UHFFFAOYSA-N 1-hydroxyethanesulfonic acid Chemical class CC(O)S(O)(=O)=O WLXGQMVCYPUOLM-UHFFFAOYSA-N 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 229920002120 photoresistant polymer Polymers 0.000 abstract description 8
- 238000009792 diffusion process Methods 0.000 abstract description 5
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000004537 pulping Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 238000010009 beating Methods 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N beta-hydroxyethanesulfonic acid Natural products OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000206 photolithography Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000002223 garnet Substances 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000001459 lithography Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- VMJFYMAHEGJHFH-UHFFFAOYSA-M triphenylsulfanium;bromide Chemical compound [Br-].C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 VMJFYMAHEGJHFH-UHFFFAOYSA-M 0.000 description 1
- ZFEAYIKULRXTAR-UHFFFAOYSA-M triphenylsulfanium;chloride Chemical compound [Cl-].C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 ZFEAYIKULRXTAR-UHFFFAOYSA-M 0.000 description 1
- GDXHNOZSKQKGCT-UHFFFAOYSA-M tris(4-methylphenyl)sulfanium;chloride Chemical compound [Cl-].C1=CC(C)=CC=C1[S+](C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 GDXHNOZSKQKGCT-UHFFFAOYSA-M 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention belongs to the technical field of photoresist, and discloses a sulfonium salt photo-acid generator synthesized by 20-hydroxyduraline and a preparation method thereof. The structure general formula of the sulfonium salt photo-acid generator synthesized by 20-hydroxyduraline is as follows:
wherein R is1Is a linking group, R2Is a hydrocarbon group or a fluorine-containing hydrocarbon group, P1、P2And P3Independently of one another, represents hydrogen or optionally substituted alkyl having 1 to 12 carbon atoms. The synthesis steps are as follows: reacting 20-hydroxyduraline with sulfoacetate compound under catalyst condition or with di (trichloromethyl) carbonate and hydroxyethanesulfonic compound under alkaline condition to form 2-containingIntermediates of 0-hydroxygarnet base structure and sulfonic acid structure; and carrying out ion exchange reaction on the intermediate and halogenated sulfonium, and purifying reaction liquid to obtain the photoacid generator containing a 20-hydroxyduraline structure. The sulfonium salt photo-acid generator synthesized by the invention has low diffusion and hydrophilic-lipophilic balance, 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 synthesized by 20-hydroxyduraline and a preparation method thereof.
Background
The photolithography material (specifically referred to as photoresist), also called photoresist, is the most critical functional chemical material involved in photolithography technology, and the main components are resin, Photo Acid Generator (PAG), and corresponding additives and solvents.
As the feature size of Integrated Circuits (ICs) is gradually reduced, the influence of the acid diffusion length on the lithography pattern becomes more and more significant, including low mask fidelity, deterioration of LWR (Line Width Roughness), and deterioration of pattern rectangularity. The structure of the PAG anion has been found to play an important role in the overall performance of the photoresist by affecting the interaction between the PAG and other photoresist components. These interactions affect the diffusion characteristics of the photogenerated acid. It is therefore very important to prepare photoacid generators (PAGs) with controllable acid diffusivity.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provides a sulfonium salt photo-acid generator synthesized by 20-hydroxyduraline and a preparation method thereof.
In order to solve the technical problems, the invention provides the following technical scheme:
the invention provides a sulfonium salt photo-acid generator synthesized by 20-hydroxyduraline, which has the following structural general formula:
wherein R is1Is a linking group, R2Is a hydrocarbon group or a fluorine-containing hydrocarbon group; p1、P2And P3Independently of one another, represents hydrogen or optionally substituted alkyl having 1 to 12 carbon atoms.
As a preferable technical means of the present invention, R is1Is an ester group or a carbonate group.
As a preferred embodiment of the present invention, the photoacid generator includes the following structure:
wherein, the P1、P2And P3Independently of one another, represents hydrogen or optionally substituted alkyl having 1 to 12 carbon atoms.
As a preferred technical solution of the present invention, the photoacid generator specifically includes the following structure:
the preparation method of the sulfonium salt photo-acid generator synthesized by 20-hydroxyduraline comprises the following steps:
s1, carrying out esterification reaction on the 20-hydroxygarnet base I and a sulfoacetate compound under the condition of a catalyst, and purifying to obtain an intermediate II containing a 20-hydroxygarnet base structure and a sulfonic acid structure;
and S2, carrying out ion exchange reaction on the intermediate II and halogenated sulfonium, and purifying reaction liquid to obtain the sulfonium salt photo-acid generator III containing the 20-hydroxyduraline structure.
The synthetic route is as follows:
In a preferred embodiment of the present invention, the sulfoacetate compound in S1 is sodium carboxydifluoromethanesulfonate and sodium carboxymethylsulfonate.
As a preferred embodiment of the present invention, S1 is replaced with: reacting 20-hydroxygarnet base I with bis (trichloromethyl) carbonate and hydroxyethanesulfonic acid compounds under alkaline conditions, and purifying to obtain an intermediate II containing a 20-hydroxygarnet base structure and a sulfonic acid structure;
the synthetic route is as follows:
wherein R is1Is a carbonate group, R2Is a hydrocarbon group or a fluorine-containing hydrocarbon group; m is an alkali metal.
As a preferable technical scheme of the invention, the hydroxyethanesulfonic acid compound is 1, 1-difluoro-2-hydroxy-ethanesulfonic acid sodium salt.
Preferably, the hydroxyethanesulfonic acid compound is 1, 1-difluoro-2-hydroxy-ethanesulfonic acid sodium salt.
Compared with the prior art, the invention has the following beneficial effects:
(1) the sulfonium salt photo-acid generator synthesized by 20-hydroxygarnet base, provided by the invention, has the advantages that the anion comprises a 20-hydroxygarnet base structure and an ester group structure, the molecular weight of the 20-hydroxygarnet base is 414.49, the molecular weight is larger, the diffusion of the photo-acid generator can be reduced, the edge roughness of a photoresist is reduced, the photo-acid generator contains amino, and the diffusion of the photo-acid generator can be inhibited; 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, also ensures that the photoacid generator has certain hydrophilicity, and can be better adhered to a silicon wafer.
(2) The invention takes 20-hydroxygarnet as a raw material, and the 20-hydroxygarnet is a green natural product, has no pollution, and is simple and easy to obtain.
(3) The synthesis process is simple and convenient to operate.
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
1-3 parts of photoacid generator prepared by using 20-hydroxyduraline as raw material, wherein the synthetic route is as follows:
the method comprises the following specific steps:
s1, sodium carboxydifluoromethanesulfonate (24.2mmol, 4.8g), dicyclohexylcarbodiimide (24.2mmol,5g) and 4-dimethylaminopyridine (4.09mmol,0.5g) were added to a solution of 20-hydroxyduraline 1-1(24.1mmol,10g) in dichloromethane (150g), followed by stirring at room temperature for 24 hours. The reaction solution was concentrated, and the residue was added to methyl t-butyl ether for beating, and the above-mentioned mixture was filtered, and the dried cake was collected to obtain solid compound 1-2(20.2mmol, 12g, yield 83.7%).
S2, Compound 1-2(20.2mmol, 12g) and triphenylsulfonium bromide (20.1mmol,6.9g) were dissolved in a mixed solvent of dichloromethane (80g) and water (80 g). The mixture was stirred at 30 ℃ for 24 hours. The reaction solution was washed with deionized water and the organic solvent was evaporated off, after which the residue obtained was dissolved in dichloromethane and added to methyl tert-butyl ether for pulping. The resulting solid was vacuum filtered, washed with methyl tert-butyl ether and vacuum dried to give 1-3(18.0mmol, 15g, 89.0% yield) of an off-white solid photoacid generator.
Example 2
2-3 parts of photoacid generator prepared by taking 20-hydroxygarnet base as a raw material, wherein the synthetic route is as follows:
the method comprises the following specific steps:
s1, sodium carboxymethyl sulfonate (24.7mmol,4g), dicyclohexylcarbodiimide (24.2mmol,5g) and 4-dimethylaminopyridine (4.09mmol,0.5g) were added to a solution of 20-hydroxyduraline 2-1(24.1mmol,10g) in dichloromethane (150g), followed by stirring at room temperature for 24 hours. The reaction solution was concentrated, and the residue was slurried in methyl t-butyl ether, the mixture was filtered, and the dried cake was collected to give compound 2-2(17.9mmol, 10g, 74.2%) as a solid.
S2, Compound 2-2(17.9mmol, 10g) and tri-p-tolylsulfonium chloride (17.9mmol,6.1g) were dissolved in a mixed solvent of dichloromethane (80g) and water (80 g). The mixture was stirred at 30 ℃ for 24 hours. The reaction solution was washed with deionized water and the organic solvent was evaporated off, after which the residue obtained was dissolved in dichloromethane and added to methyl tert-butyl ether for pulping. The resulting solid was vacuum filtered, washed with methyl tert-butyl ether and vacuum dried to give 2-3(14.9mmol, 12.5g, 83.0% yield) as an off-white solid photoacid generator.
Example 3
3-3 parts of photoacid generator prepared by taking 20-hydroxyl garnet base as a raw material, wherein the synthetic route is as follows:
the method comprises the following specific steps:
s1, pyridine (60.7mmol,4.8g) and bis (trichloromethyl) carbonate (8.09mmol,2.4g) were added to dichloromethane (150g) under nitrogen protection at 0 ℃ with stirring, then 20-hydroxygarnet 3-1(24.1mmol,10g) was added slowly. The reaction mixture was stirred at 25 ℃ for 3 hours. Then 1, 1-difluoro-2-hydroxy-ethanesulfonic acid sodium salt (24.4mmol, 4.5g) was added to the reaction solution, and stirred for 10 hours. Concentration by rotary evaporation gave a mixture which was filtered and washed three times with acetonitrile. The mixed acetonitrile solution was concentrated and added to methyl t-butyl ether for beating, and the above-mentioned mixture was filtered, and the dried cake was collected to obtain solid compound 3-2(17.6mmol, 11g, yield 73.0%).
S2, Compound 3-2(17.6mmol, 11g) and triphenylsulfonium chloride (17.7mmol,5.3g) were dissolved in a mixed solvent of dichloromethane (70g) and water (70 g). The mixture was stirred at 30 ℃ for 4 hours. The reaction solution was washed with deionized water and the organic solvent was evaporated off, after which the residue obtained was dissolved in dichloromethane and added to methyl tert-butyl ether for pulping. The resulting solid was vacuum filtered, washed with methyl tert-butyl ether and vacuum dried to give 3-3(15.0mmol, 13g, 85.3% yield) as an off-white solid.
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 (8)
1. A sulfonium salt photoacid generator synthesized from 20-hydroxyduraline, characterized in that the structure general formula of the photoacid generator is as follows:
2. The sulfonium salt-based photoacid generator synthesized from 20-hydroxyduraline according to claim 1, wherein R is1Is an ester group or a carbonate group.
3. The sulfonium salt-based photoacid generator synthesized from 20-hydroxygarnet base according to claim 1 or 2, characterized in that the photoacid generator comprises the following structure:
wherein, the P1、P2And P3Independently of one another, represent hydrogen or have 1 to 12 carbon atomsOptionally substituted alkyl of a subgroup.
4. The sulfonium salt-based photoacid generator synthesized from 20-hydroxyduraline according to claim 3, wherein the photoacid generator specifically comprises the following structure:
5. a preparation method of a sulfonium salt photo-acid generator synthesized by 20-hydroxyduraline is characterized by comprising the following steps:
s1, carrying out esterification reaction on the 20-hydroxygarnet base I and a sulfoacetate compound under the condition of a catalyst, and purifying to obtain an intermediate II containing a 20-hydroxygarnet base structure and a sulfonic acid structure;
s2, carrying out ion exchange reaction on the intermediate II and halogenated sulfonium, and purifying reaction liquid to obtain a sulfonium salt photo-acid generator III containing a 20-hydroxyduraline structure;
the synthetic route is as follows:
wherein R is1Is an ester group, R2Is a hydrocarbon group or a fluorine-containing hydrocarbon group; p1、P2And P3Independently of one another, represents hydrogen or optionally substituted alkyl having 1 to 12 carbon atoms; m is an alkali metal.
6. The method for producing a sulfonium salt-based photoacid generator synthesized from 20-hydroxyduraline according to claim 5, wherein the sulfoacetate compound in S1 is sodium carboxydifluoromethanesulfonate and sodium carboxymethylsulfonate.
7. The method for producing a sulfonium salt-based photoacid generator synthesized from 20-hydroxyduraline according to claim 5, wherein S1 is replaced with: reacting 20-hydroxygarnet base I with bis (trichloromethyl) carbonate and hydroxyethanesulfonic acid compounds under alkaline conditions, and purifying to obtain an intermediate II containing a 20-hydroxygarnet base structure and a sulfonic acid structure;
the synthetic route is as follows:
wherein R is1Is a carbonate group, R2Is a hydrocarbon group or a fluorine-containing hydrocarbon group; m is an alkali metal.
8. The method for producing a sulfonium salt-based photoacid generator synthesized from 20-hydroxyduraline according to claim 7, wherein the hydroxyethanesulfonic compound is 1, 1-difluoro-2-hydroxy-ethanesulfonic acid sodium salt.
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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 |
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