Photosensitive photoresist resin monomer containing polycyclic beta-ketone structure and synthesis method thereof

A technology of resin monomer and synthesis method, which is applied in the field of photosensitive resin monomer and its synthesis, can solve the problems of different solubility and poor polarity of polar developers, achieve good uniformity, large difference in solubility, and improve sensitivity and resolution rate effect

Inactive Publication Date: 2020-11-03
XUZHOU B&C CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Photosensitive resin monomer is an important part of photoresist polymer resin, the main function is to produce polarity difference before and after exposure, resulting in different solubility in polar developer, the invention provides a photosensitive photoresist resin monomer with a new structure body

Method used

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  • Photosensitive photoresist resin monomer containing polycyclic beta-ketone structure and synthesis method thereof
  • Photosensitive photoresist resin monomer containing polycyclic beta-ketone structure and synthesis method thereof
  • Photosensitive photoresist resin monomer containing polycyclic beta-ketone structure and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Add spiro[4.5]dec-2-ene-1,4-dione A (50g, 305mmol) into dichloromethane (1.2L), cool to 0°C in an ice-water bath, add m-chloroperoxybenzoic acid (62g , 359mmol), the reaction solution was raised to room temperature and stirred for 16 hours, filtered, the filtrate was neutralized by adding saturated sodium bicarbonate solution, the aqueous phase was extracted with dichloromethane (200mL×3), the organic phase was washed with saturated brine, and separated. After drying with anhydrous sodium sulfate and spin-drying in vacuo, the oily compound B (46.8 g, 260 mmol, 85.3%) was obtained.

[0026] Compound B (46.8g, 260mmol) was added to 3M sulfuric acid (500mL), heated to reflux and stirred for 16 hours, the reaction solution was cooled to 5 degrees Celsius, and sodium carbonate powder was added under stirring to adjust the pH to weak alkalinity, and the solvent was spin-dried , the solid was added into THF (500 mL) and stirred, the solid was removed by filtration, and the sol...

Embodiment 2

[0030] Compound D (10g, 40mmol) and 3,4-dihydro-2H-pyran (3.4g, 40mmol) were added to acetonitrile (100mL), methanesulfonic acid (0.5g, 5mmol) was added, and the reaction solution was stirred at room temperature React for 16 hours, add saturated sodium bicarbonate solution to quench the reaction, concentrate in vacuo to remove the acetonitrile solvent, add water (100 mL), extract the aqueous phase with ethyl acetate (100 mL×3), combine the organic phases, and wash the organic phases with saturated brine. Drying over anhydrous sodium sulfate gave the crude product, which was purified by distillation to obtain resin monomer E-2 (12.6 g, 37 mmol, 94.5%).

Embodiment 3

[0032] Add compound D (10g, 40mmol) to acetonitrile (200mL), add triethylamine (8g, 79mmol), cool to 0°C with ice water, slowly add 1-chloro-1-methoxy-2-methyl Propane (4.9g, 40mmol) in acetonitrile solution (80mL), raised to 50°C and stirred for 12 hours, then quenched the reaction by adding saturated sodium bicarbonate solution under ice water cooling, concentrated to remove acetonitrile, added ethyl acetate (200mL) and water (150mL), liquid separation, the aqueous phase was extracted three times with ethyl acetate (100mL×3), the organic phase was combined, the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and spin-dried in vacuo to obtain the crude product, which was distilled and purified to obtain the resin Monomer E-3 (11.5 g, 34 mmol, 85.7%).

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Abstract

The invention discloses a photosensitive photoresist resin monomer containing a polycyclic beta ketone structure, and relates to the field of photoresist resin monomers; wherein the structural formulaof the photosensitive photoresist resin monomer is shown in the specification, R1 is methyl or H, R2 and R3 are respectively and independently hydrogen, alkyl and naphthenic base, R4 is alkyl or naphthenic base, and R2 and R4, R3 and R4 or R2 and R3 can be connected through a covalent bond to form a cyclic structure; wherein n is an integer of 1-10, and the resin monomer has large solubility difference before and after exposure, can reduce roughness and improve sensitivity and resolution, is beneficial to formation of a photoetching pattern with good uniformity, and has good etching resistance.

Description

technical field [0001] The invention relates to the field of photoresist resin monomers, in particular to a photosensitive resin monomer and a synthesis method thereof. Background technique [0002] Photolithography technology refers to the chemical sensitivity of photoresist materials (especially photoresist) under the action of visible light, ultraviolet rays, electron beams, etc., through exposure, development, etching and other processes, the design on the mask plate Graphics microfabrication technology that transfers graphics to the substrate. [0003] Photolithography materials (especially photoresist), also known as photoresist, are the most critical functional chemical materials involved in photolithography technology. The main components are resin, photoacid generator, and corresponding additives and solvents. , This type of material is chemically sensitive to light (including visible light, ultraviolet rays, electron beams, etc.), and its solubility in the develop...

Claims

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Application Information

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IPC IPC(8): C07C69/54C07C67/29C07D309/12G03F7/027G03F7/004
CPCC07C69/54C07C67/08C07C67/29C07C45/64C07D301/14C07D303/32C07D309/12G03F7/027G03F7/004C07C2603/94C07C2601/08C07C2601/14C07C2603/74C07C49/513
Inventor 傅志伟贺宝元邵严亮潘新刚薛富奎
Owner XUZHOU B&C CHEM CO LTD
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