Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Photoresist resin monomer containing Meldrum's acid structure and synthesis method thereof

A technology of resin monomer and synthesis method, which is applied in the field of photoresist resin monomer containing Mie's acid structure and its synthesis, can solve the problems of reduced etching resistance, higher price, etc. Etching resistance, the effect of increasing alkali solubility

Inactive Publication Date: 2021-04-16
上海博栋化学科技有限公司
View PDF7 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Photoresist resin is obtained by copolymerization of different resin monomers, and different resin monomers play different roles, such as deprotection and degradation under photoacid, adjusting alkali solubility, adjusting adhesion with wafer, and increasing etch resistance Wait, the existing resin monomers for adjusting alkali solubility mostly contain fluorine, such as hexafluoroisopropanol structure, and the electron-withdrawing effect of F makes the resin monomer have a certain acidity, and the F-containing structure usually reduces the etching resistance properties, and in terms of synthesis, F atoms are basically introduced by raw materials, and fluorine-containing raw materials are generally more expensive. The present invention provides a new type of resin monomer without F

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Photoresist resin monomer containing Meldrum's acid structure and synthesis method thereof
  • Photoresist resin monomer containing Meldrum's acid structure and synthesis method thereof
  • Photoresist resin monomer containing Meldrum's acid structure and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Preparation of Resin Monomers 1-3

[0026] The synthetic route is as follows:

[0027]

[0028] Reaction steps:

[0029] 3-Hydroxy-2-butanone 1-1 (20 g, 227 mmol) was added to dichloromethane (500 mL), triethylamine (45 g, 445 mmol) was added, the ice water was cooled to 0 °C, and acryloyl chloride ( 25g, 276mmol), warmed to room temperature and stirred for 3 hours, quenched by adding water (250mL) under ice-water cooling, the aqueous phase was extracted three times with dichloromethane (100mL×3), the combined organic phases were washed with saturated brine, anhydrous sodium sulfate After drying, concentrated in vacuo to obtain compound 1-2 (29.8 g, 210 mmol, yield: 92.4%).

[0030] Malonic acid (22 g, 211 mmol) and acetic anhydride (25.6 g, 251 mmol) were added to the reaction flask, concentrated sulfuric acid (1.8 g, 18.4 mmol) was added under ice-water bath cooling, stirred until malonic acid was dissolved, and slowly added dropwise Compound 1-2 (29.8 g, 210 mm...

Embodiment 2

[0032] Synthesis of Resin Monomers 2-4

[0033] The synthetic route is as follows:

[0034]

[0035] 3-Hydroxyadamantane-1-carboxylic acid 2-1 (20 g, 102 mmol) was added to dichloromethane (300 mL), triethylamine (21 g, 208 mmol) was added, and acryloyl chloride ( 10 g, 110 mmol), warmed to room temperature and stirred for 3 hours, under ice-water cooling, added water (300 mL) to quench, the aqueous phase was extracted with dichloromethane (150 mL×3), the organic phases were combined, washed with saturated brine, and concentrated in vacuo to obtain Compound 2-2 (23.1 g, 92 mmol, yield: 90.6%);

[0036] Compound 2-2 (23.1 g, 92 mmol) and 3-hydroxy-2-butanone (8.2 g, 93 mmol) were added to toluene (250 mL), p-toluenesulfonic acid (2 g, 12 mmol) was added, and the mixture was heated to reflux for 16 hours, Water (150 mL) was added to the reaction solution, the layers were separated, the aqueous phase was extracted with ethyl acetate (80 mL×3), the organic phases were combine...

Embodiment 3

[0039] Synthesis of Resin Monomers 3-4

[0040]

[0041] The synthetic route is as follows:

[0042] 1,3-adamantanediol 3-1 (20 g, 119 mmol) was added to dichloromethane (350 mL), triethylamine (24 g, 237 mmol) was added, and acryloyl chloride (12.9 g) was slowly added dropwise in an ice-water bath. , 143 mmol), rose to room temperature and stirred for 3 hours, quenched by adding water (200 mL) under ice-water bath cooling, the aqueous phase was extracted with dichloromethane (100 mL×3), the organic phases were combined and washed with saturated brine, and concentrated in vacuo to obtain Compound 3-2 (24 g, 108 mmol, yield: 90.9%).

[0043] Compound 3-2 (24 g, 108 mmol) was added to dichloromethane (300 mL), followed by carbonyldiimidazole (17.6 g, 109 mmol), stirred at 40°C for 3 hours, concentrated, added acetonitrile (300 mL), and then added 1- Hydroxy-2-butanone (9.5 g, 108 mmol) was continuously stirred at room temperature for 3 hours, the reaction solution was conce...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a photoresist resin monomer containing a Meldrum's acid structure, and relates to the field of photoresist resin monomers. The structural formula of the photoresist resin monomer is shown in the specification, R1 is methyl or H, R2 is alkyl, naphthenic base, alkyl containing O atoms, or naphthenic base containing O atoms, R3 is H or alkyl, and the resin monomer is beneficial to increase of the alkali solubility of the photoresist resin, the edge side roughness of a photo-etched pattern can be improved, the etching resistance is better, the resolution of the photo-etched pattern is greatly improved, and the adsorption force of the photoresist on a silicon wafer can be improved.

Description

technical field [0001] The invention relates to the field of photoresist resin monomers, in particular to a photoresist resin monomer containing a Michaelis acid structure and a synthesis method thereof. Background technique [0002] Photolithography technology refers to the use of the chemical sensitivity of photoresist under the action of visible light, ultraviolet light, electron beam, etc., through the process of exposure, development, etching, etc., to transfer the pattern designed on the mask to the substrate. Graphic micromachining technology. [0003] Photoresist, also known as photoresist, is the most critical functional chemical material involved in lithography technology. The main components are resin, photoacid generator, and corresponding additives and solvents. These materials are photochemically sensitive. , After photochemical reaction, its solubility in developing solution changes. According to different photochemical reaction mechanisms, photoresist is di...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07D319/06G03F7/004
Inventor 贺宝元潘惠英蒋小惠王尹卓郭颖
Owner 上海博栋化学科技有限公司
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com