CN114315625A - Preparation method of acid diffusion inhibitor - Google Patents
Preparation method of acid diffusion inhibitor Download PDFInfo
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- CN114315625A CN114315625A CN202111632871.1A CN202111632871A CN114315625A CN 114315625 A CN114315625 A CN 114315625A CN 202111632871 A CN202111632871 A CN 202111632871A CN 114315625 A CN114315625 A CN 114315625A
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Abstract
The invention relates to a preparation method of an acid diffusion inhibitor, which comprises the following reaction route:
wherein R is1Is a hydrogen atom or an alkyl group, R2Is an alkyl group. The method comprises the following steps: b) adding a compound shown in a formula II into an alcohol solvent, adding an acid catalyst, and reacting to obtain a mixed product; c) adding an alkaline compound into the mixed product, adjusting the pH value to be alkaline, then removing the alcohol solvent, d) adding a first solvent, filtering, and concentrating the filtrate to obtain a crude product; e) adding polymerization inhibitor into the crude product, and then distilling under reduced pressure to obtain the compound shown in the formula I. Acid diffusion inhibition prepared by the inventionThe agent polymerization is less and the purity is high.
Description
Technical Field
The invention relates to the technical field of photoresist, in particular to a preparation method of an acid diffusion inhibitor.
Background
The chemically amplified photoresist is a photoresist based on the principle of chemical amplification, and the main components of the chemically amplified photoresist are polymer resin, Photo Acid Generator (PAG), and corresponding additives (additives) and solvent. PAG is a light-sensitive compound that decomposes under light to produce an acid (H +). These acids act as catalysts to cleave the pendant acid labile groups on the polymer resin during the Post Exposure Bake (PEB) process and generate new acids. The shedding of the pendant groups changes the polarity of the polymer resin, and after enough pendant groups are shed, the photoresist can be dissolved in a developing solution.
One of the ways to control the diffusion capability of PAGs in photolithographic processes is to use basic additives, known as acid diffusion inhibitors, to reduce the diffusion range of PAGs using the principle of acid-base neutralization. Controlling PAG diffusion is an important tool to improve resolution and reduce line width roughness. The existing micromolecular acrylic acid diffusion inhibitor is easy to polymerize and difficult to purify.
Disclosure of Invention
The present invention aims at providing a method for preparing high-purity acid diffusion inhibitor to overcome the defects of the prior art.
In order to achieve the object of the present invention, the present application provides the following technical solutions.
In a first aspect, the present application provides a process for the preparation of an acid diffusion inhibitor, the reaction scheme being as follows:
preferably, R1Is a hydrogen atom or C1～C6Alkyl radical, R2Is C1～C6An alkyl group.
The method comprises the following steps:
b) adding a compound shown in a formula II into an alcohol solvent, adding an acid catalyst, and reacting to obtain a mixed product;
c) adding alkaline compound into the mixed product, adjusting pH to alkalinity, then removing the alcohol solvent,
d) adding a first solvent, filtering, and concentrating the filtrate to obtain a crude product;
e) adding polymerization inhibitor into the crude product, and then distilling under reduced pressure to obtain the compound shown in the formula I.
In an embodiment of the first aspect, step b) further includes at least one of the following technical features:
b1) the acid catalyst is concentrated sulfuric acid or p-toluenesulfonic acid;
b2) the alcohol solvent is selected from one of methanol, ethanol, isopropanol, n-butanol, 1-pentanol, cyclopentanol, cyclohexanol and 1-hexanol;
b3) the reaction temperature is 23-26 ℃, and the reaction time is 1-5 h.
In an embodiment of the first aspect, step c) further includes at least one of the following technical features:
c1) the alkaline compound is selected from one of sodium bicarbonate, sodium carbonate and potassium carbonate;
c2) adjusting the pH value to be more than 9;
c3) the temperature for removing the alcohol solvent is not more than 35 ℃.
In one embodiment of the first aspect, the preparation method further comprises the following technical features:
the step d) is specifically as follows: adding a first solvent, separating out a solid, filtering to obtain a first solid and a first filtrate, performing salt washing on the first filtrate, drying with anhydrous sodium sulfate, filtering to obtain a second solid and a second filtrate, and performing rotary evaporation on the second filtrate to obtain a crude product.
In an embodiment of the first aspect, the preparation method further comprises at least one of the following technical features:
d1) the temperature during rotary evaporation is not more than 35 ℃;
d2) the first solvent is selected from one of ethyl acetate, isopropyl acetate, methyl tert-butyl ether and isopropyl ether.
In an embodiment of the first aspect, step e) further includes at least one of the following technical features:
e1) the polymerization inhibitor is selected from one of phenothiazine, hydroquinone, 2, 6-di-tert-butyl-p-cresol, p-tert-butyl catechol and p-methoxyphenol;
e2) the input amount of the polymerization inhibitor is 1-2 wt% of the crude product;
e3) the vacuum distillation recovered a fraction at a temperature of 52 ℃.
In one embodiment of the first aspect, the preparation process further comprises the preparation of a compound of formula ii, the reaction scheme is as follows:
preferably, R1Is a hydrogen atom or C1～C6Alkyl radical
The method comprises the following steps:
a) dissolving a compound shown in the formula III and paraformaldehyde in a solvent, adding a catalyst under a stirring state, reacting, and removing the solvent through rotary evaporation to obtain a compound shown in the formula II.
In an embodiment of the first aspect, step a) further includes at least one of the following technical features:
a1) the molar ratio of the compound of the formula III to paraformaldehyde is 1: (1-1.5), such as 1: 1.1;
a2) the solvent is selected from one of dichloromethane, dichloroethane and chloroform;
a3) the catalyst is selected from one of sodium tert-butoxide, sodium methoxide and sodium ethoxide,
a4) the addition amount of the catalyst is 0.1-0.2 wt% of the compound shown in the formula III;
a5) the reaction temperature is 35-38 ℃, and the reaction time is 2-5 h.
In one embodiment of the first aspect, step a) further comprises the following refining step, in particular:
a6) and (3) removing the solvent by rotary evaporation to obtain a crude product, dissolving the crude product in acetone, cooling, crystallizing and filtering to obtain the compound shown in the formula II.
In one embodiment of the first aspect, the refining step further comprises the following technical features:
a61) the temperature for dissolving the crude product in acetone is 50-60 ℃;
a62) the crystallization temperature is-10 to-30 ℃.
Compared with the prior art, the invention has the beneficial effects that:
the acid diffusion inhibitor prepared by the invention has less polymerization and high purity.
Drawings
FIG. 1 is an LC spectrum of the crude intermediate prepared in example 1;
FIG. 2 is a LC spectrum of the intermediate product prepared in example 1;
FIG. 3 is a GC detection spectrum of the product prepared in example 1.
Detailed Description
Unless otherwise indicated, implied from the context, or customary in the art, all parts and percentages herein are by weight and the testing and characterization methods used are synchronized with the filing date of the present application. Where applicable, the contents of any patent, patent application, or publication referred to in this application are incorporated herein by reference in their entirety and their equivalent family patents are also incorporated by reference, especially as they disclose definitions relating to synthetic techniques, products and process designs, polymers, comonomers, initiators or catalysts, and the like, in the art. To the extent that a definition of a particular term disclosed in the prior art is inconsistent with any definitions provided herein, the definition of the term provided herein controls.
The numerical ranges in this application are approximations, and thus may include values outside of the ranges unless otherwise specified. A numerical range includes all numbers from the lower value to the upper value, in increments of 1 unit, provided that there is a separation of at least 2 units between any lower value and any higher value. For example, if a component, physical or other property (e.g., molecular weight, etc.) is recited as 100 to 1000, it is intended that all individual values, e.g., 100, 101,102, etc., and all subranges, e.g., 100 to 166,155 to 170,198 to 200, etc., are explicitly recited. For ranges containing a numerical value less than 1 or containing a fraction greater than 1 (e.g., 1.1, 1.5, etc.), then 1 unit is considered appropriate to be 0.0001, 0.001, 0.01, or 0.1. For ranges containing single digit numbers less than 10 (e.g., 1 to 5), 1 unit is typically considered 0.1. These are merely specific examples of what is intended to be expressed and all possible combinations of numerical values between the lowest value and the highest value enumerated are to be considered to be expressly stated in this application. It should also be noted that the terms "first," "second," and the like herein do not define a sequential order, but merely distinguish between different structures.
When used with respect to chemical compounds, the singular includes all isomeric forms and vice versa (e.g., "hexane" includes all isomers of hexane, individually or collectively) unless expressly specified otherwise. In addition, unless explicitly stated otherwise, the use of the terms "a", "an" or "the" are intended to include the plural forms thereof.
The terms "comprising," "including," "having," and derivatives thereof do not exclude the presence of any other component, step or procedure, and are not intended to exclude the presence of other elements, steps or procedures not expressly disclosed herein. To the extent that any doubt is eliminated, all compositions herein containing, including, or having the term "comprise" may contain any additional additive, adjuvant, or compound, unless expressly stated otherwise. Rather, the term "consisting essentially of … …" excludes any other components, steps or processes from the scope of any of the terms hereinafter recited, except those necessary for performance. The term "consisting of … …" does not include any components, steps or processes not specifically described or listed. Unless explicitly stated otherwise, the term "or" refers to the listed individual members or any combination thereof.
The synthetic route is as follows:
the materials were as follows:
examples
The following will describe in detail the embodiments of the present invention, which are implemented on the premise of the technical solution of the present invention, and the detailed embodiments and the specific operation procedures are given, but the scope of the present invention is not limited to the following embodiments.
Example 1
The first step is as follows:
the reaction equation is as follows:
the operation process is as follows:
a1 liter four-necked reaction flask was charged with methacrylamide (85g, 1mol), paraformaldehyde (33.1g, 1.1mol), and methylene chloride (550g), and 85mg (0.1% catalytic amount) of sodium tert-butoxide was added under stirring at an internal temperature of 35 to 38 ℃. Reacting for 3 hours at 35-38 ℃, sampling and detecting by HPLC (raw materials are less than or equal to 6%), as shown in figure 1. Removing the solvent by rotary evaporation to obtain an oily substance; the crude intermediate was obtained as a white solid by suction drying at 23 ℃ in about 115g with 100% molar yield and 94.5% purity, and the LCMS spectrum is shown in FIG. 1.
Refining: adding 5g of crude product and 15g of acetone into a 50mL four-mouth bottle, heating to 50-60 ℃, stirring, dissolving, gradually cooling, and crystallizing at about-10 ℃. Stirring for 20 minutes at-25-30 ℃, filtering, and pumping to obtain an intermediate product of 4g of white solid, the molar yield of which is 80 percent, and sampling and LCMS (product is more than 99 percent) for detection, wherein the results are shown in figure 2.
The second step is that:
the reaction equation is as follows:
the operation process is as follows:
A1L reaction flask was charged with the intermediate (113g, 0.98mol) methanol (350g) and stirred, and 0.6g (0.5% catalytic amount) of concentrated sulfuric acid was added dropwise thereto at room temperature (23-26 ℃ C.). Reacting for 2 hours at room temperature (23-26 ℃) (the content GC of the intermediate product is detected to be less than or equal to 2%).
Adding NaHCO3(1.2g), sulfuric acid was neutralized with stirring to a pH > 9. At 35 ℃ the major part of the methanol solvent was removed by rotary evaporation (no droplets in the condenser), then ethyl acetate (350g) was added, a white solid precipitated, the solid was removed by filtration and washed with saturated brine (90g x 2). Anhydrous sodium sulfate (30g) was added to remove water, and the solid was removed by filtration. The filtrate was rotary evaporated to remove the solvent to give 130g of crude liquid.
130g of crude product is put into a 250mL four-port bottle, phenothiazine (2.4g) is added, then reduced pressure distillation is carried out, the oil bath temperature is 65 ℃, and the top temperature is about 52 ℃, and effluent begins to exist. The reaction mixture was collected for about 2 hours, and 113g of the fraction (GC. gtoreq.95%) was collected in a molar yield of 89.3% and about 1g of the residue (containing no phenothiazine) was collected and subjected to GC analysis to obtain 99% purity, the results of which are shown in FIG. 3.
Example 2
An intermediate product was obtained by the same preparation operation as in example 1 except for the preparation conditions in the second step.
Second step of
A1L reaction flask was charged with the intermediate (113g, 0.98mol) methanol (350g) and stirred, and 0.6g (0.5% catalytic amount) of concentrated sulfuric acid was added dropwise thereto at room temperature (23-26 ℃ C.). The reaction is carried out for 2 hours at room temperature (25 ℃) (the GC content of the intermediate product is detected to be less than or equal to 2%).
Adding NaHCO3(2g) The sulfuric acid is neutralized with stirring to a pH of > 10.5. At 30 ℃, rotatingThe major part of the methanol solvent was removed by rotary evaporation (no droplets in the condenser), ethyl acetate (350g) was added to precipitate a white solid, which was removed by filtration and washed with saturated brine (90g x 2). Anhydrous sodium sulfate (30g) was added to remove water, and the solid was removed by filtration. The solvent was removed by rotary evaporation to give 131g of crude liquid.
131g of crude product is placed in a 250mL four-port bottle, phenothiazine (2.4g) is added, then reduced pressure distillation is carried out, effluent begins to exist at the oil bath temperature of 65 ℃ and the top temperature of about 52 ℃. Received for about 2 hours, and had 117g of fraction, 92.4% molar yield, and 99.53% purity.
Comparative example 1
An intermediate product was obtained by the same preparation operation as in example 1 except for the preparation conditions in the second step.
Second step of
A1L reaction flask was charged with the intermediate (113g, 0.98mol) methanol (350g) and stirred, and 0.6g (0.5% catalytic amount) of concentrated sulfuric acid was added dropwise thereto at room temperature (23-26 ℃ C.). Reacting for 2 hours at room temperature (25 ℃) (detecting the content GC of the intermediate product is less than or equal to 2 percent).
Adding NaHCO3(0.08g) sulfuric acid was neutralized with stirring to pH 7. At 35 ℃ the major part of the methanol solvent was removed by rotary evaporation (no droplets in the condenser), ethyl acetate (350g) was added to precipitate a white solid, which was removed by filtration and washed with saturated brine (90g x 2). Anhydrous sodium sulfate (30g) was added to remove water, and the solid was removed by filtration. The solvent was removed by rotary evaporation to give 124g of crude liquid.
124g of the crude product is placed in a 250mL four-port bottle, phenothiazine (2.4g) is added, then reduced pressure distillation is carried out, the oil bath temperature is 65 ℃, and the top temperature is about 52 ℃, and effluent begins to exist. The product was received for about 2 hours and was 105g of a fraction with a molar yield of 83% and a purity of 92.2%.
Comparative example 2
An intermediate product was obtained by the same preparation operation as in example 1 except for the preparation conditions in the second step.
Second step of
A1L reaction flask was charged with the intermediate (113g, 0.98mol) methanol (350g) and stirred, and 0.6g (0.5% catalytic amount) of concentrated sulfuric acid was added dropwise thereto at room temperature (23-26 ℃ C.). Reacting for 2 hours at room temperature (25 ℃) (detecting the content GC of the intermediate product is less than or equal to 2 percent).
Adding NaHCO3(0.2g) sulfuric acid was neutralized with stirring to a pH > 9. At 40 ℃ the major part of the methanol solvent was removed by rotary evaporation (no droplets in the condenser), ethyl acetate (350g) was added to precipitate a white solid, which was removed by filtration and washed with saturated brine (90g x 2). Anhydrous sodium sulfate (30g) was added to remove water, and the solid was removed by filtration. The solvent was removed by rotary evaporation to yield 125g of crude liquid.
125g of the crude product is placed in a 250mL four-port bottle, phenothiazine (2.4g) is added, then reduced pressure distillation is carried out, the oil bath temperature is 65 ℃, and the top temperature is about 52 ℃, and effluent begins to exist. The reaction mixture was received for about 2 hours, and 85g of a fraction was obtained in a molar yield of 67% and a purity of 85.2%, and the product was polymerized to a large extent.
The embodiments described above are intended to facilitate the understanding and appreciation of the application by those skilled in the art. It will be readily apparent to those skilled in the art that various modifications to these embodiments may be made, and the generic principles described herein may be applied to other embodiments without the use of the inventive faculty. Therefore, the present application is not limited to the embodiments herein, and those skilled in the art who have the benefit of this disclosure will appreciate that many modifications and variations are possible within the scope of the present application without departing from the scope and spirit of the present application.
Claims (10)
1. The preparation method of the acid diffusion inhibitor is characterized in that the reaction route is as follows:
the method comprises the following steps:
b) adding a compound shown in a formula II into an alcohol solvent, adding an acid catalyst, and reacting to obtain a mixed product;
c) adding alkaline compound into the mixed product, adjusting pH to alkalinity, then removing the alcohol solvent,
d) adding a first solvent, filtering, and concentrating the filtrate to obtain a crude product;
e) adding polymerization inhibitor into the crude product, and then distilling under reduced pressure to obtain the compound shown in the formula I.
2. The method of preparing an acid diffusion inhibitor according to claim 1, wherein step b) further comprises at least one of the following technical features:
b1) the acid catalyst is selected from concentrated sulfuric acid or p-toluenesulfonic acid;
b2) the alcohol solvent is selected from one of methanol, ethanol, isopropanol, n-butanol, 1-pentanol, cyclopentanol, cyclohexanol and 1-hexanol;
b3) the reaction temperature is 23-26 ℃, and the reaction time is 1-5 h.
3. The method of preparing an acid diffusion inhibitor according to claim 1, wherein step c) further comprises at least one of the following technical features:
c1) the alkaline compound is selected from one of sodium bicarbonate, sodium carbonate and potassium carbonate;
c2) adjusting the pH value to be more than 9;
c3) the temperature for removing the alcohol solvent is not more than 35 ℃.
4. The method of preparing an acid diffusion inhibitor according to claim 1, wherein the method further comprises the following technical features:
the step d) is specifically as follows: adding a first solvent, separating out a solid, filtering to obtain a first solid and a first filtrate, performing salt washing on the first filtrate, drying with anhydrous sodium sulfate, filtering to obtain a second solid and a second filtrate, and performing rotary evaporation on the second filtrate to obtain a crude product.
5. The method of preparing an acid diffusion inhibitor according to claim 4, wherein the method further comprises at least one of the following technical features:
d1) the temperature of the rotary evaporation is not more than 35 ℃;
d2) the first solvent is selected from one of ethyl acetate, isopropyl acetate, methyl tert-butyl ether and isopropyl ether.
6. The method of preparing an acid diffusion inhibitor according to claim 1, wherein step e) further comprises at least one of the following technical features:
e1) the polymerization inhibitor is selected from one of phenothiazine, hydroquinone, 2, 6-di-tert-butyl-p-cresol, p-tert-butyl catechol and p-methoxyphenol;
e2) the input amount of the polymerization inhibitor is 1-2 wt% of the crude product;
e3) the vacuum distillation recovered a fraction at a temperature of 52 ℃.
7. The method of preparing an acid diffusion inhibitor according to claim 1, further comprising preparing a compound of formula ii, the reaction scheme being:
the method comprises the following steps:
a) dissolving a compound shown in the formula III and paraformaldehyde in a solvent, adding a catalyst under a stirring state, reacting, and removing the solvent through rotary evaporation to obtain a compound shown in the formula II.
8. The method of preparing an acid diffusion inhibitor according to claim 7, wherein step a) further comprises at least one of the following technical features:
a1) the molar ratio of the compound of the formula III to paraformaldehyde is 1: (1-1.5);
a2) the solvent is selected from one of dichloromethane, dichloroethane and chloroform;
a3) the catalyst is selected from one of sodium tert-butoxide, sodium methoxide and sodium ethoxide,
a4) the addition amount of the catalyst is 0.1-0.2 wt% of the compound shown in the formula III;
a5) the reaction temperature is 35-38 ℃, and the reaction time is 2-5 h.
9. The method of preparing an acid diffusion inhibitor according to claim 7, wherein step a) further comprises the following refining step:
a6) and (3) removing the solvent by rotary evaporation to obtain a crude product, dissolving the crude product in acetone, cooling, crystallizing and filtering to obtain the compound shown in the formula II.
10. The method of preparing an acid diffusion inhibitor according to claim 9, wherein said refining step further comprises the following technical features:
a61) the temperature for dissolving the crude product in acetone is 50-60 ℃;
a62) the crystallization temperature is-10 to-30 ℃.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62281849A (en) * | 1986-05-29 | 1987-12-07 | Nitto Chem Ind Co Ltd | Production of n-alkoxymethyl (meth)acrylamide |
| JPH08176081A (en) * | 1994-12-22 | 1996-07-09 | Nitto Chem Ind Co Ltd | Production of n-alkoxymethyl(meth)acrylamide |
| JP2006225446A (en) * | 2005-02-15 | 2006-08-31 | San Nopco Ltd | (meth)acrylamide and photo-polymerizable composition containing it |
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2021
- 2021-12-28 CN CN202111632871.1A patent/CN114315625A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62281849A (en) * | 1986-05-29 | 1987-12-07 | Nitto Chem Ind Co Ltd | Production of n-alkoxymethyl (meth)acrylamide |
| JPH08176081A (en) * | 1994-12-22 | 1996-07-09 | Nitto Chem Ind Co Ltd | Production of n-alkoxymethyl(meth)acrylamide |
| JP2006225446A (en) * | 2005-02-15 | 2006-08-31 | San Nopco Ltd | (meth)acrylamide and photo-polymerizable composition containing it |
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