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Photoresist resin monomer synthesized from 3-ethylbicyclo[3.3.1]nonane-2,4-dione, and synthesis method thereof

A technology of resin monomer and synthesis method, which is applied in the field of photoresist resin monomer and its synthesis, can solve the problem of low resolution of photolithographic patterns, achieve improved resolution, increase dissolution speed difference, and improve edge roughness Effect

Pending Publication Date: 2020-05-12
上海博栋化学科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, due to the specific structure of the acid-sensitive resin monomer in the existing photoresist, there is a problem of low photolithographic pattern resolution

Method used

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  • Photoresist resin monomer synthesized from 3-ethylbicyclo[3.3.1]nonane-2,4-dione, and synthesis method thereof
  • Photoresist resin monomer synthesized from 3-ethylbicyclo[3.3.1]nonane-2,4-dione, and synthesis method thereof
  • Photoresist resin monomer synthesized from 3-ethylbicyclo[3.3.1]nonane-2,4-dione, and synthesis method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0032] This embodiment provides a photoresist resin monomer synthesized by 3-ethylbicyclo[3.3.1]nonane-2,4-dione, the reaction scheme of the synthesis method of the photoresist resin monomer is as follows :

[0033]

[0034] It specifically includes the following steps:

[0035] S1, preparation of methyl Grignard reagent: first add 2.7g of magnesium chips (111mmol) to 15ml of anhydrous ether, and add an iodine tablet to obtain a reaction solution; then, dissolve 10.6g of methyl bromide (112mmol) in 25mL Prepare a methyl bromide ether solution in diethyl ether; then, under the protection of nitrogen, first add 6mL methyl bromide ether solution to the above reaction solution. After 5 minutes, the reaction solution boils slightly, and the color of iodine disappears. Under stirring, continue to Add the remaining methyl bromide ethyl ether solution dropwise, and add 20 mL of diethyl ether, raise the temperature to keep boiling slightly, and reflux for half an hour to obtain the...

Embodiment 2

[0039] This embodiment provides a photoresist resin monomer synthesized by 3-ethylbicyclo[3.3.1]nonane-2,4-dione, the reaction scheme of the synthesis method of the photoresist resin monomer is as follows :

[0040]

[0041] It specifically includes the following steps:

[0042] S1. According to the steps S1-S2 of the above-mentioned Example 1, 9.5 g of the intermediate (Formula 2-2, 45 mmol) was obtained, and the yield was 80.6%.

[0043]S2. Dissolve 9.5g of the above intermediate in 120mL of anhydrous tetrahydrofuran, and add 18.2g of triethylamine (180mmol); then, cool to 0 degrees Celsius with ice water, and slowly drop into it under the protection of nitrogen Add a solution of methacryloyl chloride (9.4g, 90mmol) in anhydrous tetrahydrofuran (50mL) to obtain a reaction solution; after the reaction solution rises to room temperature and continues to react for 5 hours, the reaction solution is then concentrated under vacuum to remove the solvent, and added 50mL of ethy...

Embodiment 3

[0045] This embodiment provides a photoresist resin monomer synthesized by 3-ethylbicyclo[3.3.1]nonane-2,4-dione, the reaction scheme of the synthesis method of the photoresist resin monomer is as follows :

[0046]

[0047] It specifically includes the following steps:

[0048] S1. Preparation of ethyl Grignard reagent: first add 2.7g of magnesium chips (111mmol) to 15ml of anhydrous ether, and add an iodine tablet to obtain a reaction solution; then, dissolve 12.1g of ethyl bromide (111mmol) in 25mL Prepare ethyl bromide ether solution in diethyl ether; then, under the protection of nitrogen, first add 6mL ethyl bromide ether solution to the above reaction solution. After 5 minutes, the reaction solution boils slightly, and the color of iodine disappears. Under stirring, continue to Add the remaining ethyl bromide ether solution dropwise, and add 20 mL of diethyl ether, raise the temperature to keep boiling slightly, and reflux for half an hour to obtain ethyl Grignard r...

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Abstract

The invention discloses a photoresist resin monomer synthesized from 3-ethylbicyclo[3.3.1]nonane-2,4-dione, and a synthesis method thereof, and belongs to the technical fields of chemical synthesis and photoetching. The structural general formula of the photoresist resin monomer is represented by formula I shown in the description; and in the formula I, R1 is saturated alkane or cycloalkane, and R2 is hydrogen or a methyl group. The synthesis method comprises the following steps: carrying out a Grignard reaction on 3-ethylbicyclo[3.3.1] nonane-2,4-dione and an alkyl Grignard reagent or a cycloalkyl Grignard reagent under the protection of an inert gas, adding water for quenching after the Grignard reaction is finished, and carrying out post-treatment purification to obtain an intermediate;and carrying out an esterification reaction on the intermediate and acryloyl chloride or methacryloyl chloride, and carrying out post-treatment purification after the esterification reaction is finished in order to obtain the resin monomer. The resin monomer is a degradable resin monomer, and polymer resin containing the resin monomer has good etching resistance and can improve the resolution ofphotoresist photoetching patterns.

Description

technical field [0001] The invention relates to the technical fields of chemical synthesis and photolithography, in particular to a photoresist resin monomer synthesized from 3-ethylbicyclo[3.3.1]nonane-2,4-dione 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...

Claims

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Application Information

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IPC IPC(8): C07C67/14C07C69/54C08F22/14G03F7/004
CPCC07C67/14C07C69/54C08F22/14G03F7/004C07C2602/46C07C2601/14
Inventor 蒋小惠毕景峰潘惠英郭颖
Owner 上海博栋化学科技有限公司
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