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Degradable photoresist resin monomer synthesized from pyran-3, 5-diketone and synthesis method thereof

A technology of resin monomer and synthesis method, applied in the field of resin monomer and its synthesis, can solve the problems of insufficient resolution, weak etching resistance, etc., and achieve the advantages of good solubility, good etching resistance and improved edge roughness Effect

Pending Publication Date: 2020-10-16
XUZHOU B&C CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Resin is a polymer formed by the polymerization of various resin monomers. Among them, the acid-sensitive resin monomer is an important part to realize the difference in the dissolution of the resin in the developer solution before and after exposure. The common acid-sensitive resin monomer has only one acid-sensitive group. , the resin monomer is a linear polymer with weak etching resistance, and the poor solubility in the developer solution after exposure is only determined by the acid-sensitive resin monomer, resulting in insufficient resolution.

Method used

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  • Degradable photoresist resin monomer synthesized from pyran-3, 5-diketone and synthesis method thereof
  • Degradable photoresist resin monomer synthesized from pyran-3, 5-diketone and synthesis method thereof
  • Degradable photoresist resin monomer synthesized from pyran-3, 5-diketone and synthesis method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0021]

[0022] The first step: a. Preparation of methyl Grignard reagent: adding magnesium chips (4.3g, 177mmol) to anhydrous ether (15mL), then adding an iodine tablet, and dissolving methyl bromide (17g, 179mmol) Prepare a solution in diethyl ether (25mL). Under nitrogen protection, first add methyl bromide diethyl ether solution (6mL) to the above reaction solution. After a few minutes, the reaction solution boils slightly and the color of iodine disappears. Continue to drop Add the remaining ether solution of methyl bromide, add ether (20mL), raise the temperature and keep boiling slightly, and reflux for half an hour; b. Synthesis of intermediate 1-2: Cool the prepared methyl Grignard reagent with ice water, stir Add a solution of 2H-pyran-3,5(4H,6H)-dione 1-1 (10g, 87.6mmol) in diethyl ether (20mL) dropwise, control the rate of addition, and keep the reaction solution slightly boiling. After the addition, Stirring was continued for half an hour at 25 degrees Celsius,...

Embodiment 2

[0025]

[0026] The first step: the operation steps and raw material dosage are the same as the first step reaction of Example 1, and the reaction obtains compound 2-2 (10.8g, 73.9mmol, 84.3%);

[0027] The second step: the operation steps are the same as the second step reaction of Example 1, intermediate 1-2 (10.6g, 72.5mmol) is replaced by intermediate 2-2 (10.8g, 73.9mmol), acryloyl chloride (13.5g, 149 mmol) was replaced by methacryloyl chloride (15.5 g, 148 mmol) to obtain compound 2-3 (16.7 g, 59.2 mmol, 80.1%).

Embodiment 3

[0029]

[0030] The first step, the operating steps are the same as the first step of Example 1, wherein methyl bromide (17g, 179mmol) is changed to ethyl bromide (19.2g, 176mmol), to obtain compound 3-2 (12.3g, 70.6mmol, 80.5 %);

[0031] The second step: the operation steps are the same as the second step of Example 1, the intermediate 1-2 (10.6g, 72.5mmol) is replaced by 3-2 (12.3g, 70.6mmol), and triethylamine (30g, 296mmol) is replaced Triethylamine (29g, 287mmol), acryloyl chloride (13.5g, 149mmol) was replaced by acryloyl chloride (13g, 144mmol) to obtain compound 3-3 (16.5g, 58.4mmol, 82.8%).

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Abstract

The invention discloses a degradable photoresist resin monomer synthesized from pyran-3, 5-diketone and a synthesis method thereof, and relates to the field of photoresist resin monomers. The structural formula of the degradable photoresist resin monomer is shown in the specification, R1 is hydrogen or methyl, and R2 is saturated alkane or cycloalkane. The synthesis method comprises the followingsteps: carrying out Grignard reaction on 2H-pyran-3, 5 (4H, 6H)-diketone (I) and an alkyl Grignard reagent or a cycloalkyl Grignard reagent to obtain an intermediate (II); and carrying out esterification reaction on the intermediate (II) and acryloyl chloride or methacryloyl chloride to obtain a resin monomer (III). The resin monomer has better etching resistance, the difference between dissolution rates before and after exposure is increased, the improvement of the edge roughness of a developed pattern is facilitated, the resolution of a photoetching pattern is greatly improved, and the solubility of polymer resin containing the resin monomer in an ester solvent is improved.

Description

technical field [0001] The invention relates to the field of photoresist resin, in particular to a 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 developer solution changes thro...

Claims

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Application Information

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IPC IPC(8): C07D309/10G03F7/027G03F7/004
CPCC07D309/10G03F7/027G03F7/004
Inventor 傅志伟贺宝元邵严亮毛国平余文清薛富奎刘司飞
Owner XUZHOU B&C CHEM CO LTD
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