CN114276239B - Preparation method of ketal structure-containing acid-sensitive photoresist resin monomer - Google Patents
Preparation method of ketal structure-containing acid-sensitive photoresist resin monomer Download PDFInfo
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- CN114276239B CN114276239B CN202111646902.9A CN202111646902A CN114276239B CN 114276239 B CN114276239 B CN 114276239B CN 202111646902 A CN202111646902 A CN 202111646902A CN 114276239 B CN114276239 B CN 114276239B
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- photoresist resin
- ketal structure
- sensitive photoresist
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- 229920005989 resin Polymers 0.000 title claims abstract description 21
- 239000011347 resin Substances 0.000 title claims abstract description 21
- 239000002253 acid Substances 0.000 title claims abstract description 19
- 239000000178 monomer Substances 0.000 title claims abstract description 17
- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 238000000526 short-path distillation Methods 0.000 claims abstract description 10
- 239000002120 nanofilm Substances 0.000 claims abstract description 9
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 238000005406 washing Methods 0.000 claims abstract description 5
- 238000007259 addition reaction Methods 0.000 claims abstract description 3
- 239000003513 alkali Substances 0.000 claims abstract description 3
- 239000012295 chemical reaction liquid Substances 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 8
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 4
- MMVUZMIOJNPDME-UHFFFAOYSA-N 4-methylbenzenesulfonate;triethylazanium Chemical compound CC[NH+](CC)CC.CC1=CC=C(S([O-])(=O)=O)C=C1 MMVUZMIOJNPDME-UHFFFAOYSA-N 0.000 claims description 4
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 claims description 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 2
- 230000008569 process Effects 0.000 description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000002952 polymeric resin Substances 0.000 description 5
- 229920003002 synthetic resin Polymers 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000654 additive Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- -1 vinyl diethyl ether Chemical compound 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 230000009471 action Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000001360 synchronised effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The application relates to a preparation method of an acid sensitive photoresist resin monomer containing a ketal structure, which comprises the following synthetic routes:wherein R is 1 Is C 1 ～C 6 Alkyl of R 2 Is a hydrogen atom or C 1 ～C 6 Alkyl of (a); the preparation method comprises the following steps: a) Adding a compound of a formula II and a catalyst into an organic solvent, then adding a compound of a formula III, and carrying out addition reaction to obtain a compound of a formula I; b) And c), performing alkali washing on the reaction liquid in the step a), and performing short-path distillation on a molecular film to obtain the ketal structure-containing acid-sensitive photoresist resin monomer. The preparation method of the application ensures that the product has high yield and high purity.
Description
Technical Field
The application relates to the technical field of photoresist, in particular to a preparation method of an acid sensitive photoresist resin monomer containing a ketal structure.
Background
A chemically amplified resist is a resist based on the principle of chemical amplification, and its main components are a polymer resin, a photoacid generator (photo acid generator, PAG), and corresponding additives (additives) and solvents. . Wherein the polymer resin is formed by copolymerization between resin monomers of different side chain structures, the side chain structures are key components for endowing the polymer resin with required functions, and polar groups and acid-sensitive groups are generally provided for the polymer resin. The polar groups can balance the hydrophilicity and hydrophobicity of the resin, improve adhesion between the resin and the substrate, and provide developability to the host resin. The acid-sensitive group can be separated from the side chain under the action of the photoacid generator, so that the resin is converted from insoluble to alkali-soluble, and the solubility contrast of the exposed area and the unexposed area is realized.
The ketal structure-containing acid-sensitive resin monomer is a polymer resin widely applied to 193nm photoresist, but the ketal structure is unstable, so that the ketal structure is not easy to purify.
Disclosure of Invention
The application aims to overcome the defects of the prior art and provide a preparation method of an acid sensitive photoresist resin monomer containing a ketal structure.
In order to achieve the purpose of the application, the application provides the following technical scheme.
In a first aspect, the present application provides a method for preparing an acid-sensitive photoresist resin monomer containing a ketal structure, which is characterized in that the preparation method comprises the following synthetic route:
wherein R is 1 Is C 1 ～C 6 Alkyl of R 2 Is a hydrogen atom or C 1 ～C 6 Alkyl of (a);
the preparation method comprises the following steps:
a) Adding a compound of a formula II and a catalyst into an organic solvent, then adding a compound of a formula III, and carrying out addition reaction to obtain a compound of a formula I;
b) And c), performing alkali washing on the reaction liquid in the step a), and performing short-path distillation on a molecular film to obtain the ketal structure-containing acid-sensitive photoresist resin monomer.
In one embodiment of the first aspect, in step a), the catalyst is selected from at least one of pyridinium tosylate or triethylamine p-toluenesulfonate.
In one embodiment of the first aspect, in step a), the compound of formula II and the compound of formula III are added in a molar ratio of 1 (1-2), such as 1:1.2.
In one embodiment of the first aspect, in step a), the catalyst is 1% to 10% by weight, such as 5% by weight, of the compound of formula II.
In one embodiment of the first aspect, in step a), the organic solvent is selected from at least one of dichloromethane or dichloroethane.
In one embodiment of the first aspect, in step a), the temperature at which the compound of formula III is added is less than or equal to 12 ℃.
In one embodiment of the first aspect, in step a), the reaction temperature is 28 to 32 ℃ and the reaction time is 12 to 24 hours.
In one embodiment of the first aspect, in step b), the alkaline wash is a 5wt% sodium hydroxide solution wash.
In one embodiment of the first aspect, in step b), the jacket oil temperature of the molecular membrane short path distillation is between 35 and 40 ℃.
Compared with the prior art, the application has the beneficial effects that:
the preparation method of the application ensures that the product has high yield and high purity, the yield is more than 79 percent, and the purity is more than 98.5 percent; and compared with common distillation, the molecular film short-path distillation is adopted, so that high-temperature distillation is avoided, the decomposition of products is effectively prevented, and the yield is improved.
Drawings
FIG. 1 is a GC spectrum for the reaction controls in example 1;
FIG. 2 is a GC spectrum of the product of example 1.
Detailed Description
Unless otherwise indicated, implied from the context, or common denominator in the art, all parts and percentages in the present application are based on weight and the test and characterization methods used are synchronized with the filing date of the present application. Where applicable, the disclosure of any patent, patent application, or publication referred to in this disclosure is incorporated herein by reference in its entirety, and the equivalent patents are incorporated herein by reference, especially with respect to the definitions of synthetic techniques, product and process designs, polymers, comonomers, initiators or catalysts, etc. in the art, as disclosed in these documents. If the definition of a particular term disclosed in the prior art is inconsistent with any definition provided in the present application, the definition of the term provided in the present application controls.
The numerical ranges in the present application are approximations, so that it may include the numerical values outside the range unless otherwise indicated. The numerical range includes all values from the lower value to the upper value that increase by 1 unit, provided that there is a spacing 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., as well as all subranges, e.g., 100 to 166,155 to 170,198 to 200, etc., are explicitly recited. For ranges containing values less than 1 or containing fractions greater than 1 (e.g., 1.1,1.5, etc.), then 1 unit is suitably considered to be 0.0001,0.001,0.01, or 0.1. For a range containing units of less than 10 (e.g., 1 to 5), 1 unit is generally considered to be 0.1. These are merely specific examples of what is intended to be provided, 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 disclosure. It should also be noted that the terms "first," "second," and the like herein do not limit the order of precedence, but are used merely to distinguish materials of different structures.
As used with respect to chemical compounds, the singular includes all isomeric forms and vice versa unless explicitly stated otherwise (e.g., "hexane" includes all isomers of hexane, either individually or collectively). In addition, unless explicitly stated otherwise, the use of the terms "a," "an," or "the" include plural referents.
The terms "comprises," "comprising," "including," and their derivatives do not exclude the presence of any other component, step or process, and are not related to whether or not such other component, step or process is disclosed in the present application. For the avoidance of any doubt, all use of the terms "comprising", "including" or "having" herein, unless expressly stated otherwise, may include any additional additive, adjuvant or compound. Rather, the term "consisting essentially of … …" excludes any other component, step or process from the scope of any of the terms recited below, except as necessary for operability. The term "consisting of … …" does not include any components, steps or processes not specifically described or listed. The term "or" refers to the listed individual members or any combination thereof unless explicitly stated otherwise.
Examples
The following will describe embodiments of the present application in detail, and the embodiments and specific operation procedures are given by implementing the present application on the premise of its technical solution, but the scope of protection of the present application is not limited to the following embodiments.
Example 1
The reaction equation:
the material ratio is as follows:
the operation process comprises the following steps:
methacrylic acid (300 g,3.48 mol), pyridine p-toluenesulfonate (15 g) and methylene dichloride (900 g) are added into a 2L four-port reaction bottle under the protection of nitrogen, stirring is started, the temperature is reduced to 10+/-2 ℃ after stirring and clearing, vinyl diethyl ether (301.5 g,4.18 mol) is added dropwise, and the dropwise adding temperature is controlled to be not higher than 12 ℃.
After the completion of the dropping, the temperature was raised to 30.+ -. 2 ℃ and the reaction was continued for 12 hours. Sampling center control (RTmin4.38.ltoreq.1% for methacrylic acid), the results are shown in FIG. 1).
After passing the central control, 300mL of 5wt% sodium hydroxide solution is added for washing twice, the organic phase is concentrated to obtain crude product, 452g of colorless liquid is obtained through molecular film short-path distillation (jacket oil temperature is 35-40 ℃), the GC spectrum is shown in figure 2, GC=98.9% and the yield y=82.1%.
In the operation process, molecular film short-path distillation is adopted, so that high-temperature distillation is avoided, decomposition is prevented, and the purity of more than 98.5% can be obtained; and the use of the pyridine p-toluenesulfonate is more complete in reaction (the methacrylic acid content of the raw material is less than or equal to 1%) than the use of the p-toluenesulfonic acid alone for catalysis, so that the dosage is less, and the obtained product is colorless and has high yield.
Example 2
Methacrylic acid (300 g,3.48 mol), triethylamine p-toluenesulfonate (15 g) and dichloroethane (1000 g) are added into a 2L four-port reaction bottle under the protection of nitrogen, stirring is started, the temperature is reduced to 10+/-2 ℃ after stirring and clearing, vinyl diethyl ether (251.5 g,4.18 mol) is added dropwise, and the dropwise adding temperature is controlled to be not higher than 12 ℃.
After the completion of the dropping, the temperature was raised to 30.+ -. 2 ℃ and the reaction was continued for 12 hours. Sampling center control (methacrylic acid RTmin4.38.ltoreq.1%).
After passing the central control, 300mL of 5wt% sodium hydroxide solution is added for washing twice, the organic phase is concentrated to obtain a crude product, and colorless liquid 433 g, GC=99.0% and yield y=79.2% are obtained through short-path distillation of a molecular film (jacket oil temperature is 35-40 ℃).
In the operation process, molecular film short-path distillation is adopted, so that high-temperature distillation is avoided, decomposition is prevented, and the purity of more than 98.5% can be obtained; and the triethylamine p-toluenesulfonate is adopted for catalysis, so that the reaction is more complete (the methacrylic acid content of the raw material is less than or equal to 1 percent), the consumption is less, and the obtained product is colorless and has high yield.
The embodiments are described above in order to facilitate the understanding and application of the present application by those of ordinary skill in the art. It will be apparent to those skilled in the art that various modifications can be made to these embodiments and that the general principles described herein may be applied to other embodiments without the use of inventive faculty. Accordingly, the present application is not limited to the embodiments herein, and those skilled in the art, based on the present disclosure, make improvements and modifications within the scope and spirit of the application.
Claims (6)
1. The preparation method of the ketal structure-containing acid-sensitive photoresist resin monomer is characterized by comprising the following synthetic routes:
wherein R is 1 Is C 1 ～C 6 Alkyl of R 2 Is a hydrogen atom or C 1 ～C 6 Alkyl of (a);
the preparation method comprises the following steps:
a) Adding a compound of a formula II and a catalyst into an organic solvent, then adding a compound of a formula III, and carrying out addition reaction to obtain a compound of a formula I; wherein the catalyst is selected from at least one of pyridine tosylate or triethylamine p-toluenesulfonate, and the organic solvent is selected from at least one of dichloromethane or dichloroethane;
b) And c) performing alkali washing on the reaction liquid in the step a), and performing short-path distillation on the molecular film, wherein the temperature of a jacket oil of the short-path distillation on the molecular film is 35-40 ℃, so as to obtain the ketal structure-containing acid sensitive photoresist resin monomer.
2. The method for preparing an acid sensitive photoresist resin monomer containing ketal structure according to claim 1, wherein in step a), the molar ratio of the compound of formula II to the compound of formula III is 1 (1-2).
3. The method for preparing an acid sensitive photoresist resin monomer containing ketal structure according to any one of claims 1-2 wherein in step a), the catalyst is 1wt% to 10wt% of the compound of formula ii.
4. The method for preparing an acid sensitive photoresist resin monomer containing ketal structure according to claim 1 wherein in step a), the temperature of the compound of formula iii is not more than 12 ℃.
5. The method for preparing an acid sensitive photoresist resin monomer containing ketal structure according to claim 1 wherein in step a), the reaction temperature is 28-32 ℃ and the reaction time is 12-24 hours.
6. The method for preparing an acid sensitive photoresist resin monomer containing ketal structure according to claim 1 wherein in step b), the alkaline wash is a wash with 5wt% sodium hydroxide solution.
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