CN111704601A - Degradable photoresist acid-producing resin monomer synthesized from 3, 5-dihydroxycyclohexanone and preparation method thereof - Google Patents
Degradable photoresist acid-producing resin monomer synthesized from 3, 5-dihydroxycyclohexanone and preparation method thereof Download PDFInfo
- Publication number
- CN111704601A CN111704601A CN202010550069.7A CN202010550069A CN111704601A CN 111704601 A CN111704601 A CN 111704601A CN 202010550069 A CN202010550069 A CN 202010550069A CN 111704601 A CN111704601 A CN 111704601A
- Authority
- CN
- China
- Prior art keywords
- dihydroxycyclohexanone
- resin monomer
- acid
- molar ratio
- photoresist
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
- C07C321/24—Thiols, sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
- C07C321/28—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
- C07C321/30—Sulfides having the sulfur atom of at least one thio group bound to two carbon atoms of six-membered aromatic rings
-
- 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
-
- 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
Abstract
The invention discloses a degradable photoresist acid-producing resin monomer synthesized by 3, 5-dihydroxycyclohexanone and a preparation method thereof, wherein the resin monomer comprises the following structural general formula
Wherein R is1Comprising C1～C12Alkyl, heteroalkyl, or a connecting bond, R2And R4Respectively comprise hydrogen, halogen and C1～C12Alkyl or heteroalkyl, R3Is alkyl, P1、P2And P3The photoresist containing the resin monomer has better etching resistance, improves the edge roughness of a developed pattern, improves the resolution of a photoetching pattern, and has a simple preparation method of the resin monomer.
Description
Technical Field
The invention relates to the technical field of photoresist, in particular to a degradable photoresist acid-producing resin monomer synthesized from 3, 5-dihydroxycyclohexanone and a preparation method thereof.
Background
Lithography (Lithography) refers to a fine processing technique for transferring a pattern designed on a Mask (Mask) to a pattern on a substrate by using the chemical sensitivity of a Lithography material (particularly a photoresist) under the action of visible light, ultraviolet light, an electron beam and the like through the processes of exposure, development, etching and the like.
The main components of the photoresist are resin, photoacid generator, and corresponding additives and solvents, and these materials have chemical sensitivity with light (including visible light, ultraviolet light, electron beam, etc.) and undergo a photochemical reaction to change their solubility in a developing solution. According to the difference of photochemical reaction mechanism, the photoresist is divided into a positive photoresist and a negative photoresist: after exposure, the solubility of the photoresist in a developing solution is increased, and the photoresist with the same pattern as that of the mask is obtained and is called as a positive photoresist; after exposure, the photoresist has reduced solubility or even no solubility in a developing solution, and a negative photoresist with a pattern opposite to that of the mask is obtained.
Photoacid generators are one of the key components in chemically amplified photoresists, and their structure and properties have a large influence on the image formed by the photoresist system. The acid-sensitive resin is a compound which can be decomposed to generate specific acid under the irradiation of a specific light source or radiation, the generated acid can enable the acid-sensitive resin to generate decomposition or crosslinking reaction, and the acid-sensitive resin monomer is an important component for realizing the dissolution difference of the resin in a developing solution before and after exposure.
As Integrated Circuit (IC) feature sizes have decreased, the problem of photoacid generator diffusion has become more important.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide a novel degradable photoresist acid-producing resin monomer synthesized from 3, 5-dihydroxycyclohexanone, and a corresponding preparation method.
In order to solve the technical problems, the invention provides the following technical scheme:
the invention relates to a degradable photoresist acid-producing resin monomer synthesized from 3, 5-dihydroxycyclohexanone, which comprises the following structural general formula:
wherein R is1Comprising C1～C12Alkyl, heteroalkyl, or a connecting bond, R2And R4Respectively comprise hydrogen, halogen and C1～C12Alkyl or heteroalkyl, R3Is alkyl, P1、P2And P3Respectively, include alkyl or heteroalkyl groups.
As a preferable technical means of the present invention, R is1Is a fluoroalkyl group.
As a preferred embodiment of the present invention, the resin monomer comprises the following structure:
the preparation method of the degradable photoresist acid-producing resin monomer synthesized from 3, 5-dihydroxycyclohexanone is characterized by comprising the following steps:
reacting S1, 3, 5-dihydroxycyclohexanone I with an acrylic compound under an alkaline condition, and purifying to obtain an intermediate II;
s2, forming an intermediate III containing an acetal structure by the intermediate II and the hydroxyl-containing acrylic compound under the acid catalysis condition;
s3, carrying out esterification reaction on the intermediate III and sulfonate to form an intermediate IV;
s4, the intermediate IV reacts with halogenated sulfonium to form a resin monomer V.
As a preferable technical scheme of the invention, the molar ratio of the 3, 5-dihydroxycyclohexanone I, the acrylic compound and the alkali is 1 (0.9-1.1) to (1.5-3), the molar ratio of the intermediate II to the acrylic compound is 1: (0.9-1.2), wherein the molar ratio of the intermediate III to the sulfonate is 1: (1-1.2), wherein the molar ratio of the intermediate IV to the sulfonium halide is 1: (1-1.2).
In a preferred embodiment of the present invention, the molar ratio of the 3, 5-dihydroxycyclohexanone I to the acrylic compound to the base is 1:1:2, and the molar ratio of the intermediate II to the hydroxyl group-containing acrylic compound is 1:1, the molar ratio of the intermediate III to the sulfonate is 1:1, the molar ratio of the intermediate IV to the sulfonium halide is 1: 1.
in a preferred embodiment of the present invention, in S1, the acrylic compound includes one of acrylic anhydride, acryloyl chloride, methacrylic anhydride, and methacryloyl chloride.
Compared with the prior art, the invention has the following beneficial effects:
(1) the invention provides a resin monomer, which contains two unsaturated carbon-carbon double bonds and can generate crosslinking in the polymerization process with other resin monomers to form a three-dimensional network structure polymer resin, and the generated crosslinked polymer resin has better etching resistance.
(2) The resin monomer is also connected with a photoacid generator, so that the diffusion of the photoacid generator from an exposed area to a non-exposed area can be reduced, the line edge roughness is improved, and the resolution is improved.
(3) The resin monomer also comprises an acetal structure, when in exposure, the photoacid generator generates acid, so that the structure of the side chain acetal of the formed resin is broken under an acidic condition, thereby breaking the polymer resin, generating a product with smaller molecular weight, reducing the line edge roughness, simultaneously increasing the solubility of the exposed resin in a developing solution by hydroxyl groups formed by breaking the polymer resin, increasing the difference of the dissolving speeds of the polymer resin before and after exposure in the developing solution, improving the contrast of the photoresist and improving the resolution of a photoetching pattern.
(4) The invention has simple synthetic route and convenient operation.
Detailed Description
The present invention will be further described with reference to specific examples, which are intended to illustrate and explain the present invention, but are not intended to limit the present invention.
Example 1
The resin monomer 1-5 prepared by taking (3R,5S) -3, 5-dihydroxycyclohexanone as a raw material has the following structure:
specific synthetic routes of resin monomers 1-5:
the specific synthesis steps are as follows:
s1, (3R,5S) -3, 5-dihydroxycyclohexanone 1-1(10g, 76.8mmol), triethylamine (15.5g, 153.2mmol) and p-methoxyphenol (0.02g, 0.16mmol) were added to tetrahydrofuran (300g), and acryloyl chloride (7g, 77.3mmol) was added dropwise with stirring at 25 ℃ to react for 5 hours. Adding water into the reaction solution for reaction, extracting with ethyl acetate, washing the extract with sodium bicarbonate aqueous solution and saturated saline solution in sequence, and concentrating an organic layer to obtain a crude product. The crude product was purified by silica gel column chromatography to give compound 1-2(9.5g, 51.6mmol, 67.1% molar yield).
S2, Compound 1-2(9.5g, 51.6mmol), 2, 3-dihydroxypropyl acrylate (7.6g, 52.0mmol), p-toluenesulfonic acid (0.5g, 2.9mmol) and p-methoxyphenol (0.02g, 0.16mmol) were added to benzene (150g), and heated under reflux for 5 hours. The reaction mixture was washed with water and saturated brine in this order, and then benzene was removed by distillation under reduced pressure to give a crude product, which was purified by distillation to give compound 1-3(11g, 35.2mmol, molar yield 68.3%).
S3, Compound 1-3(11g, 35.2mmol), sodium difluorosulfoacetate (7g, 35.3mmol), p-toluenesulfonic acid (0.5g, 2.9mmol) and p-methoxyphenol (0.02g, 0.16mmol) were added to toluene (150g), and heated under reflux for 8 hours. The reaction solution was filtered and washed with acetonitrile. The resulting acetonitrile-containing solution was concentrated, and added to methyl t-butyl ether to slurry and filtered to obtain solid compound 1-4(13.5g, 27.4mmol, molar yield 77.8%).
S4, Compounds 1 to 4(13.5g, 27.4mmol), triphenylsulfonium bromide (9.5g, 27.7mmol) and p-methoxyphenol (0.02g, 0.16mmol) were dissolved in a mixed solvent of dichloromethane (100g) and water (100 g). Stirring was carried out at 30 ℃ for 8 hours. The reaction solution was separated into an organic layer and an aqueous layer, and the organic layer was washed with deionized water, then concentrated and added to methyl t-butyl ether for recrystallization to give compound 1-5 as a solid (17g, 23.2mmol, 84.6% molar yield).
Example 2
The resin monomer 2-5 prepared by taking (3R,5S) -3, 5-dihydroxycyclohexanone as a raw material has the following structure:
the specific synthetic route of the resin monomers 2-5 is as follows:
the specific synthesis steps are as follows:
s1, (3R,5S) -3, 5-dihydroxycyclohexanone 2-1(10g, 76.8mmol), triethylamine (15.5g, 153.2mmol) and p-methoxyphenol (0.02g, 0.16mmol) were added to tetrahydrofuran (300g), and methacrylic anhydride (11.8g, 76.5mmol) was added dropwise with stirring at 25 ℃ to react for 5 hours. Adding water into the reaction solution to stop the reaction, extracting with ethyl acetate, washing the extract with sodium bicarbonate aqueous solution and saturated saline solution in sequence, and concentrating the organic layer to obtain a crude product. The crude product was purified by silica gel column to give compound 2-2(9.2g, 46.4mmol, molar yield 60.4%);
s2, Compound 2-2(9.2g, 46.4mmol), 2, 3-dihydroxypropyl acrylate (6.8g, 46.5mmol), p-toluenesulfonic acid (0.5g, 2.9mmol) and p-methoxyphenol (0.02g, 0.16mmol) were added to benzene (150g), and heated under reflux for 5 hours. Washing the reaction solution with water and saturated saline water in sequence, then distilling out benzene under reduced pressure to obtain a crude product, and distilling and purifying the crude product to obtain a compound 2-3(10.5g, 32.2mmol, and the molar yield is 69.3%);
s3, Compound 2-3(10.5g, 32.2mmol), sodium difluorosulfoacetate (6.4g, 32.3mmol), p-toluenesulfonic acid (0.5g, 2.9mmol) and p-methoxyphenol (0.02g, 0.16mmol) were added to toluene (150g), and heated under reflux for 8 hours. The reaction solution was filtered and washed with acetonitrile. Concentrating the obtained acetonitrile-containing solution, adding the concentrated acetonitrile-containing solution into methyl tert-butyl ether, pulping, and filtering to obtain solid compound 2-4(12.5g, 24.7mmol, and the molar yield is 76.7%);
s4, Compound 2-4(12.5g, 24.7mmol), tris (4-methylphenyl) sulfonium bromide (9.5g, 24.7mmol) and p-methoxyphenol (0.02g, 0.16mmol) were dissolved in a mixed solvent of dichloromethane (100g) and water (100 g). Stirring was carried out at 30 ℃ for 8 hours. The reaction solution was separated into an organic layer and an aqueous layer, and the organic layer was washed with deionized water, then concentrated and added to methyl t-butyl ether for recrystallization to give compound 2-5 as a solid (17g, 21.5mmol, 87.3% molar yield).
Example 3
The resin monomer 3-5 prepared by taking (3R,5S) -3, 5-dihydroxycyclohexanone as a raw material has the following structure:
the specific synthetic route of the resin monomers 3-5 is as follows:
the specific synthesis steps are as follows:
s1, (3R,5S) -3, 5-dihydroxycyclohexanone 1-1(10g, 76.8mmol), triethylamine (15.5g, 153.2mmol) and p-methoxyphenol (0.02g, 0.16mmol) were added to tetrahydrofuran (300g), and methacryloyl chloride (8g, 76.5mmol) was added dropwise with stirring at 25 ℃ to react for 5 hours. Adding water into the reaction solution to stop the reaction, extracting with ethyl acetate, washing the extract with sodium bicarbonate aqueous solution and saturated saline solution in sequence, and concentrating the organic layer to obtain a crude product. The crude product was purified by silica gel column to give compound 3-2(9g, 45.4mmol, 59.1% molar yield);
s2, Compound 3-2(9g, 45.4mmol), 3, 4-dihydroxybutyl acrylate (7.3g, 45.6mmol), p-toluenesulfonic acid (0.5g, 2.9mmol) and p-methoxyphenol (0.02g, 0.16mmol) were added to benzene (150g), and heated under reflux for 5 hours. The reaction solution is washed by water and saturated saline water in sequence, then benzene is removed by reduced pressure distillation to obtain a crude product, and the crude product is purified by distillation to obtain a compound 3-3(10.7g, 31.4mmol, molar yield 69.2%);
s3, Compound 3-3(10.7g, 31.4mmol), sodium difluorosulfoacetate (6.2g, 31.3mmol), p-toluenesulfonic acid (0.5g, 2.9mmol) and p-methoxyphenol (0.02g, 0.16mmol) were added to toluene (150g), and heated under reflux for 8 hours. The reaction solution was filtered and washed with acetonitrile. Concentrating the obtained acetonitrile-containing solution, adding the concentrated acetonitrile-containing solution into methyl tert-butyl ether, pulping, and filtering to obtain solid compound 3-4(13g, 25.0mmol, and the molar yield is 79.5%);
s4, Compound 3-4(13g, 25.0mmol), triphenylsulfonium bromide (8.5g, 24.8mmol) and p-methoxyphenol (0.02g, 0.16mmol) were dissolved in a mixed solvent of dichloromethane (100g) and water (100 g). Stirring was carried out at 30 ℃ for 8 hours. The reaction solution was separated into an organic layer and an aqueous layer, the organic layer was washed with deionized water, and then the organic layer was concentrated and added to methyl t-butyl ether to conduct recrystallization to obtain 3 to 5(17g, 22.3mmol, molar yield 89.5%) as a solid compound
Compared with the prior art, the invention has the following beneficial effects:
(1) the invention provides a resin monomer, which contains two unsaturated carbon-carbon double bonds and can generate crosslinking in the polymerization process with other resin monomers to form a three-dimensional network structure polymer resin, and the generated crosslinked polymer resin has better etching resistance.
(2) The resin monomer is also connected with a photoacid generator, so that the diffusion of the photoacid generator from an exposed area to a non-exposed area can be reduced, the line edge roughness is improved, and the resolution is improved.
(3) The resin monomer also comprises an acetal structure, when in exposure, the photoacid generator generates acid, so that the structure of the side chain acetal of the formed resin is broken under an acidic condition, thereby breaking the polymer resin, generating a product with smaller molecular weight, reducing the line edge roughness, simultaneously increasing the solubility of the exposed resin in a developing solution by hydroxyl groups formed by breaking the polymer resin, increasing the difference of the dissolving speeds of the polymer resin before and after exposure in the developing solution, improving the contrast of the photoresist and improving the resolution of a photoetching pattern.
(4) The invention has simple synthetic route and convenient operation.
Finally, it should be noted that: although the present invention has been described in detail with reference to the foregoing embodiments, those skilled in the art will understand that various changes, modifications and substitutions can be made without departing from the spirit and scope of the invention as defined by the appended claims. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (7)
1. A degradable photoresist acid-producing resin monomer synthesized from 3, 5-dihydroxycyclohexanone is characterized by comprising the following structural general formula:
wherein R is1Comprising C1～C12Alkyl, heteroalkyl, or a connecting bond, R2And R4Respectively comprise hydrogen, halogen and C1～C12Alkyl or heteroalkyl, R3Is alkyl, P1、P2And P3Respectively, include alkyl or heteroalkyl groups.
2. The degradable photoresist acid-producing resin monomer synthesized from 3, 5-dihydroxycyclohexanone according to claim 1, wherein R is the same as R1Is a fluoroalkyl group.
3. The degradable photoresist acid-producing resin monomer synthesized from 3, 5-dihydroxycyclohexanone according to claim 2, wherein the resin monomer comprises the following structure:
4. a method for preparing the degradable photoresist acid-producing resin monomer synthesized from 3, 5-dihydroxycyclohexanone according to any one of claims 1 to 3, which comprises the following steps:
reacting S1, 3, 5-dihydroxycyclohexanone I with an acrylic compound under an alkaline condition, and purifying to obtain an intermediate II;
s2, forming an intermediate III containing an acetal structure by the intermediate II and the hydroxyl-containing acrylic compound under the acid catalysis condition;
s3, carrying out esterification reaction on the intermediate III and sulfonate to form an intermediate IV;
s4, the intermediate IV reacts with halogenated sulfonium to form a resin monomer V.
5. The method for preparing the acid-producing resin monomer for the degradable photoresist synthesized from 3, 5-dihydroxycyclohexanone according to claim 4, wherein the molar ratio of the 3, 5-dihydroxycyclohexanone I, the acrylic compound and the alkali is 1 (0.9-1.1) to (1.5-3), and the molar ratio of the intermediate II and the hydroxyl-containing acrylic compound is 1: (0.9-1.2), wherein the molar ratio of the intermediate III to the sulfonate is 1: (1-1.2), wherein the molar ratio of the intermediate IV to the sulfonium halide is 1: (1-1.2).
6. The method for preparing the degradable photoresist acid-producing resin monomer synthesized from 3, 5-dihydroxycyclohexanone according to claim 5, wherein the molar ratio of the 3, 5-dihydroxycyclohexanone I to the acrylic compound to the alkali is 1:1:2, and the molar ratio of the intermediate II to the hydroxyl-containing acrylic compound is 1:1, the molar ratio of the intermediate III to the sulfonate is 1:1, the molar ratio of the intermediate IV to the sulfonium halide is 1: 1.
7. the method for preparing the degradable acid-producing photoresist resin monomer synthesized from 3, 5-dihydroxycyclohexanone according to claim 4, wherein in S1, the acrylic compound comprises one of acrylic anhydride, acryloyl chloride, methacrylic anhydride or methacryloyl chloride.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010550069.7A CN111704601A (en) | 2020-06-16 | 2020-06-16 | Degradable photoresist acid-producing resin monomer synthesized from 3, 5-dihydroxycyclohexanone and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010550069.7A CN111704601A (en) | 2020-06-16 | 2020-06-16 | Degradable photoresist acid-producing resin monomer synthesized from 3, 5-dihydroxycyclohexanone and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN111704601A true CN111704601A (en) | 2020-09-25 |
Family
ID=72540818
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010550069.7A Pending CN111704601A (en) | 2020-06-16 | 2020-06-16 | Degradable photoresist acid-producing resin monomer synthesized from 3, 5-dihydroxycyclohexanone and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111704601A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112661769A (en) * | 2020-12-23 | 2021-04-16 | 上海博栋化学科技有限公司 | Resin monomer synthesized from 5- (hydroxymethyl) -1, 3-cyclohexanedione and preparation method thereof |
| CN113416177A (en) * | 2021-06-24 | 2021-09-21 | 徐州博康信息化学品有限公司 | Main chain degradable photoresist resin monomer and preparation method and application thereof |
| CN113429377A (en) * | 2021-06-23 | 2021-09-24 | 徐州博康信息化学品有限公司 | Degradable resin monomer containing fluorine-free photoacid generator and preparation method and application thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1841200A (en) * | 2005-03-30 | 2006-10-04 | 住友化学株式会社 | Salt suitable for acid generator and chemical amplifying type corrosion-resistant composition containing the same |
| CN101955476A (en) * | 2009-07-16 | 2011-01-26 | 住友化学株式会社 | Salt and the photo-corrosion-resisting agent composition that contains this salt |
| JP2015043079A (en) * | 2013-07-24 | 2015-03-05 | Jsr株式会社 | Radiation-sensitive resin composition, method for forming resist pattern, polymer, compound, and production method of compound |
| CN107129448A (en) * | 2016-02-29 | 2017-09-05 | 罗门哈斯电子材料有限责任公司 | Light acid produces monomer, includes the photo-corrosion-resisting agent composition of the polymer from its derivative polymer |
-
2020
- 2020-06-16 CN CN202010550069.7A patent/CN111704601A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1841200A (en) * | 2005-03-30 | 2006-10-04 | 住友化学株式会社 | Salt suitable for acid generator and chemical amplifying type corrosion-resistant composition containing the same |
| CN101955476A (en) * | 2009-07-16 | 2011-01-26 | 住友化学株式会社 | Salt and the photo-corrosion-resisting agent composition that contains this salt |
| JP2015043079A (en) * | 2013-07-24 | 2015-03-05 | Jsr株式会社 | Radiation-sensitive resin composition, method for forming resist pattern, polymer, compound, and production method of compound |
| CN107129448A (en) * | 2016-02-29 | 2017-09-05 | 罗门哈斯电子材料有限责任公司 | Light acid produces monomer, includes the photo-corrosion-resisting agent composition of the polymer from its derivative polymer |
Non-Patent Citations (1)
| Title |
|---|
| JUNG HEE KIM等: "Antimicrobial Activity of p-Hydroxyphenyl Acrylate Derivatives", 《JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112661769A (en) * | 2020-12-23 | 2021-04-16 | 上海博栋化学科技有限公司 | Resin monomer synthesized from 5- (hydroxymethyl) -1, 3-cyclohexanedione and preparation method thereof |
| CN112661769B (en) * | 2020-12-23 | 2022-06-28 | 上海博栋化学科技有限公司 | Resin monomer synthesized from 5- (hydroxymethyl) -1, 3-cyclohexanedione and preparation method thereof |
| CN113429377A (en) * | 2021-06-23 | 2021-09-24 | 徐州博康信息化学品有限公司 | Degradable resin monomer containing fluorine-free photoacid generator and preparation method and application thereof |
| CN113416177A (en) * | 2021-06-24 | 2021-09-21 | 徐州博康信息化学品有限公司 | Main chain degradable photoresist resin monomer and preparation method and application thereof |
| CN113416177B (en) * | 2021-06-24 | 2022-10-25 | 徐州博康信息化学品有限公司 | Main chain degradable photoresist resin monomer and preparation method and application thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP6454625B2 (en) | Resin and resist composition | |
| CN111704601A (en) | Degradable photoresist acid-producing resin monomer synthesized from 3, 5-dihydroxycyclohexanone and preparation method thereof | |
| KR20100090655A (en) | Chemically amplified photoresist composition and method for forming pattern | |
| JP5512430B2 (en) | Salt and photoresist composition | |
| CN111662267B (en) | Photoresist acid-producing resin monomer containing dioxobicyclo [2.2.2] octane dicarboxylic acid ester structure and preparation method thereof | |
| CN111635341A (en) | Trifluoro sulfonamide octahydro-pentalene photoresist resin monomer and preparation method thereof | |
| JP5512431B2 (en) | Polymer, photoresist composition and pattern production method | |
| CN111056945A (en) | Photoresist resin monomer synthesized from spiro [5.5] undecane-3, 9-dione and synthesis method thereof | |
| US6258508B1 (en) | Polymer using norbornene monomers with derivatives of cholic acid, deoxycholic acid or lithocholic acid and use thereof | |
| CN113493382A (en) | Photoresist acid-sensitive resin monomer with good alkali solubility and synthesis method and application thereof | |
| CN112159341A (en) | Photoresist resin monomer | |
| CN112645923A (en) | Photoresist resin monomer containing photoacid generator and synthetic method thereof | |
| JP5992658B2 (en) | Salt and resist composition | |
| JP2002193895A (en) | Cyclic skeleton-containing 3-acryloyloxypropionic ester derivative and acrylic ester mixture | |
| CN111675720B (en) | Trifluoro sulfonamide hexahydrofuro [3,2-b ] furan photoresist resin monomer and preparation method thereof | |
| CN112592277A (en) | Degradable resin monomer synthesized by dicyclohexyl ketone and preparation method thereof | |
| CN113429292A (en) | Photoresist resin monomer and synthetic method and application thereof | |
| CN111675680A (en) | Trifluoro sulfonamide pyran type photoresist resin monomer and preparation method thereof | |
| CN112625022A (en) | Photoresist resin monomer and synthetic method thereof | |
| CN111763160A (en) | Trifluoro sulfonamide adamantane photoresist resin monomer and preparation method thereof | |
| CN112679462A (en) | Photoresist resin monomer with adamantane structure and synthesis method thereof | |
| CN111777587A (en) | Degradable photoresist resin monomer synthesized from oxaspiro [4.5] decanedione and synthesis method thereof | |
| CN111777583A (en) | Degradable photoresist resin monomer synthesized from pyran-3, 5-dione and synthesis method thereof | |
| CN112645997B (en) | Resin monomer synthesized from epiandrosterone and preparation method thereof | |
| CN111675616A (en) | Degradable photoresist resin monomer synthesized from epoxy alisma alkene and synthesis method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20200925 |