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Degradable photoresist resin monomer synthesized from furandione and synthesis method thereof

A technology of resin monomer and furandione, applied in the field of resin monomer and its synthesis, can solve the problems of insufficient resolution and weak etching resistance, achieve good solubility, good etching resistance, and improve 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 furandione and synthesis method thereof
  • Degradable photoresist resin monomer synthesized from furandione and synthesis method thereof
  • Degradable photoresist resin monomer synthesized from furandione and synthesis method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0026]

[0027] The first step: a. Preparation of methyl Grignard reagent: adding magnesium chips (4.9g, 202mmol) to anhydrous ether (15mL), then adding an iodine tablet, and dissolving methyl bromide (19g, 200mmol) 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: under nitrogen protection, the prepared methyl Grignard reagent Cool in water, add furan-3,4(2H, 5H)-diketone (10.0g, 55mmol) dropwise in diethyl ether (20mL) solution under stirring, control the rate of addition, keep the reaction solution slightly boiling, after the dropwise addition, at 25 Stirring was continued for h...

Embodiment 2

[0030]

[0031] The first step: the operation steps and raw material dosage are the same as the first step reaction in Example 1, and the reaction obtains compound 2-2 (11.5g, 87mmol, 87.1%);

[0032] The second step: the operation steps are the same as the second step reaction of Example 1, wherein the reactants and the charging amount: intermediate 1-2 (11.3g, 86mmol) is replaced by intermediate 2-2 (11.5g, 87mmol), propylene Acyl chloride (15.5g, 171mmol) was replaced by methacryloyl chloride (18.2g, 174mmol), triethylamine (34.6g, 342mmol) was replaced by triethylamine (35.3g, 349mmol), and compound 2-3 (19.3g, 72 mmol, 82.7%).

Embodiment 3

[0034]

[0035] The first step: the operation steps are the same as the first step of Example 1, wherein methyl bromide (19g, 200mmol) is changed to ethyl bromide (21.8g, 200mmol), to obtain compound 3-2 (13.5g, 84mmol, 84.3% );

[0036] The second step: the operation steps are the same as the second step reaction of Example 1, wherein reactants and charging amount: intermediate 1-2 (11.3g, 86mmol) is replaced by intermediate 3-2 (13.5g, 84mmol), propylene Acyl chloride (15.5g, 171mmol) was replaced by acryloyl chloride (15.3g, 169mmol), triethylamine (34.6g, 342mmol) was replaced by triethylamine (34.2g, 338mmol), and compound 3-3 (19.5g, 73mmol, 86.2%).

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Abstract

The invention discloses a degradable photoresist resin monomer synthesized from furandione and a synthesis method thereof, and relates to the field of photoresist resin. The structural formula of theresin monomer is shown in the specification, R1 is saturated alkane or cycloalkane, and R2 is hydrogen or methyl. The synthesis method comprises the following steps: reacting furan-3, 4 (2H, 5H)-diketone (I) with an alkyl Grignard reagent or a naphthenic base Grignard reagent under the protection of inert gas, adding water for quenching after the reaction is finished, and carrying out aftertreatment and purification to obtain an intermediate (II); and 2, esterification reaction: reacting the intermediate (II) with acryloyl chloride or methacryloyl chloride under alkaline conditions, and carrying out post-treatment purification to obtain the resin monomer (III). Polymer resin formed by polymerizing the resin monomer and other resin monomers has better etching resistance, is beneficial to improving the edge roughness of a developed pattern, greatly improves the resolution of a photoetching pattern, and increases the fat solubility.

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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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/20G03F7/027G03F7/004
CPCC07D307/20G03F7/027G03F7/004
Inventor 邵严亮傅志伟贺宝元潘新刚薛富奎汪进波
Owner XUZHOU B&C CHEM CO LTD
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