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Preparation method of acid-sensitive photoresist resin monomer

A technology of resin monomer and photoresist, applied in the field of photoresist, can solve the problem of low purity of the preparation method, and achieve the effects of high purity, high yield and less impurities

Pending Publication Date: 2022-04-12
XUZHOU B&C CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Poly(meth)acrylate system is a kind of resin polymer widely used in 193nm photoresist, but the preparation method of existing (meth)acrylate resin monomer is not high in purity

Method used

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  • Preparation method of acid-sensitive photoresist resin monomer
  • Preparation method of acid-sensitive photoresist resin monomer
  • Preparation method of acid-sensitive photoresist resin monomer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

1,

[0076]

[0077] Add methanol (720 g) and cyclohexyl formic acid (150 g, 1.17 mol) to a four-necked reaction flask, add 9 g of concentrated sulfuric acid (6 wt % of cyclohexyl formic acid) with a mass concentration of 98% under stirring, and heat to reflux for 2 h (oil bath temperature 90°C), GC traced until the raw materials basically disappeared, and after rotary distillation of methanol until there was no liquid drop (water bath temperature 40°C), oil pump simple distillation (distillation temperature 25~30°C, oil bath 50°C) obtained 133g of the product, molar yield 80%, 98.8% pure.

2,

[0078]

[0079] Tetrahydrofuran (450g) was added into the four-necked bottle, the stopper was sealed with parafilm, and weighed. Cool to -20°C with dry ice ethanol, start to pass through methyl bromide (record the weight of the steel cylinder), pay attention to observe the bubbler, after the ventilation is completed, weigh the weight of the four-necked bottle again, and confirm ...

Embodiment 2

1,

[0085]

[0086] Add methanol (720g) and cyclohexyl formic acid (150g, 1.17mol) to a four-necked reaction flask, add 15 g of concentrated sulfuric acid (10 wt% of cyclohexyl formic acid) with a mass concentration of 98% under stirring, and heat to reflux for 1.5 h (oil bath temperature 95°C), GC traced until the raw materials basically disappeared, and after rotary distillation of methanol until there was no liquid drop (water bath temperature 40°C), oil pump simple distillation (distillation temperature 25~30°C, oil bath 50°C) obtained 136g of product, molar yield The yield is 83%, and the purity is 98.6%.

2,

[0087]

[0088] Tetrahydrofuran (450g) was added into the four-necked bottle, the stopper was sealed with parafilm, and weighed. Cool to -10°C with dry ice ethanol, start to ventilate methyl chloride (record the weight of the steel cylinder), pay attention to observe the bubbler, after the ventilating, weigh the weight of the four-neck bottle again, confirm...

Embodiment 3

1,

[0093]

[0094] Methanol (720g) and cyclohexyl formic acid (150g, 1.17mol) were added to a four-necked reaction flask, and under stirring, 7.5 g of concentrated sulfuric acid (5 wt% of cyclohexyl formic acid) with a mass concentration of 98% was added, and the reaction was heated under reflux for 2.5h ( oil bath temperature 85°C), GC traced until the raw materials basically disappeared, and after rotary distilling methanol until there was no liquid drop (water bath temperature 40°C), oil pump simple distillation (distillation 25~30°C, oil bath 50°C) obtained 130g of product, molar yield Yield 78.1%, purity 98.9%.

2,

[0095]

[0096] Tetrahydrofuran (450g) was added into the four-necked bottle, the stopper was sealed with parafilm, and weighed. Cool to -20°C with dry ice ethanol, start to pass through methyl bromide (record the weight of the steel cylinder), pay attention to observe the bubbler, after the ventilation is completed, weigh the weight of the four-neck...

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Abstract

The invention relates to a preparation method of an acid-sensitive photoresist resin monomer, which is characterized in that the preparation method comprises the following reaction route: M is cycloalkyl with 5-7 carbon atoms, R1 is hydrogen atom or alkyl, and R2 is alkyl; the preparation method comprises the following steps: c) introducing halomethane into a first solvent to obtain a halomethane-containing first solvent solution; d) under the condition of inert gas, adding metal lithium and a compound in a formula IV into a first solvent, mixing, dropwise adding the first solvent solution containing halomethane prepared in the step c), stirring, reacting, and purifying to obtain a compound in a formula III; and f) adding the compound shown in the formula III and an acid-binding agent into a second solvent, mixing, dropwise adding a compound shown in the formula II, and carrying out esterification reaction and purification to obtain a compound shown in the formula I. The resin monomer obtained by the preparation method is an acid-sensitive photoresist resin monomer, and the obtained product has the advantages of high yield, high purity and few impurities.

Description

technical field [0001] The invention relates to the technical field of photoresist, in particular to a preparation method of an acid-sensitive photoresist resin monomer. Background technique [0002] The 193nm photoresist is basically a chemical amplification glue, which is a kind of photoresist based on the principle of chemical amplification, and its main components are polymer resin, photoacid generator and corresponding additives (alkaline additives, dissolution inhibitors etc.) and solvents. Among them, the polymer resin is formed by the copolymerization of resin monomers with different side chain structures. The side chain structure is the key component that endows the polymer resin with the required functions, and usually provides polar groups and acid-sensitive groups for the polymer resin. group. Polar groups can balance the hydrophilicity and hydrophobicity of the resin, improve the adhesion between the resin and the substrate, and provide developability for the ...

Claims

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Application Information

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IPC IPC(8): C07C67/14C07C69/54C07C67/48C07C67/08C07C69/75C07C29/147C07C31/135
Inventor 傅志伟潘新刚余文卿陆伟邵严亮
Owner XUZHOU B&C CHEM CO LTD
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