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Fluorine-containing photoacid generator as well as preparation method and application thereof

A technology of photoacid generators and solvents, which is applied in the preparation of sulfonates, photosensitive materials for optomechanical equipment, organic chemistry, etc., can solve the problems of incompatibility, sensitivity and resolution reduction, and reduce the Effects of phase separation, low absorption, and high thermal stability

Inactive Publication Date: 2021-10-26
安徽庆润新材料技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The technical problem to be solved by the present invention is that the photoacid generator in the prior art is not easy to be compatible with the resin after compounding, and the H produced by the acid generator in the drying process after phase separation is easy to occur + Migration to unexposed areas, resulting in loss of sensitivity and resolution

Method used

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  • Fluorine-containing photoacid generator as well as preparation method and application thereof
  • Fluorine-containing photoacid generator as well as preparation method and application thereof
  • Fluorine-containing photoacid generator as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] The preparation process of fluorine-containing photoacid generator is shown below, and r.t in the figure represents room temperature;

[0036]

[0037] Concrete preparation method comprises the following steps:

[0038] 2,3,5,6-Tetrafluorophenol (10.1 g, 61.4 mmol) was added to 22 mL of oleum (containing 30 wt % SO 3 ) at room temperature for 18 hours, and then the mixture was poured into 200 mL ice-brine. The product was precipitated by stirring in NaCl solution until no more precipitate formed.

[0039] The mixture was filtered through a sintered glass disc, and the collected solid was placed in 330 mL of boiling CH 3 In CN, hot filtration through paper followed by slow cooling to ambient temperature gave a colorless crystalline product, 9.64 g (64%) after drying in vacuo. Then react overnight with methacrylic acid in trifluoroacetic acid (TFA) and trifluoroacetic anhydride (TFAA) under nitrogen as a medium, then react the reaction product with triphenylsulfur c...

Embodiment 2

[0041] The preparation process of fluorine-containing photoacid generator is as follows:

[0042]

[0043] Concrete preparation method comprises the following steps:

[0044] Trifluoromethylphenol (15g) was added dropwise to 20mL oleum (containing 20wt% SO 3), the mixture was maintained at 100 °C for 1 h. The mixture was stirred with water (25 mL) at room temperature for 2 days, then washed with a large amount of water (100 mL) and sodium chloride. A tan solid (19.1 g) was collected by filtration.

[0045] The intermediate was then reacted with methacrylic acid in trifluoroacetic acid (TFA) and trifluoroacetic anhydride (TFAA) overnight under nitrogen atmosphere. After removing the solvent and washing with ether, the yield was 51%. Finally, it was reacted with an aqueous solution of triphenylsulfur chloride (0.03 mol) with a mass fraction of 50 wt%, overnight at room temperature. The product was purified with dichloromethane and n-hexane to obtain triphenylmethacryloxy...

Embodiment 3

[0047] The photosensitive resin was prepared by using the fluorine-containing photoacid generator in Example 1, and the preparation process is as follows.

[0048]

[0049] Specifically include the following steps:

[0050] The composition ratio of the photosensitive resin in this embodiment is shown in Table 1, wherein the volume ratio of tetrahydrofuran and acetonitrile is 1:1.

[0051] Table 1 is the component ratio of photosensitive resin in the present embodiment

[0052] components Proportion(%) 2-Ethyl-2-adamantyl methacrylate 42 2-Oxotetrahydrofuran-3-yl methacrylate 8 2-thiophene methyl methacrylate 8 4-Hydroxystyrene 7 Fluorinated Photoacid Generators 3 Azodiethylbutyronitrile 1.5 THF, Acetonitrile 30.5

[0053] Weigh and weigh 4-hydroxystyrene, 2-oxotetrahydrofuran-3-yl methacrylate, 2-thiophene methyl methacrylate, and 2-ethyl-2-adamantyl methacrylate according to the proportion of ingredients , fluorin...

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Abstract

The invention discloses a fluorine-containing photoacid generator, and relates to the technical field of photosensitive resin synthesis, and the fluorine-containing photoacid generator comprises one or two of compounds represented by a structural formula E and a structural formula F, or the structural formula of the fluorine-containing photoacid generator is a structural formula E or a structural formula F shown in the specification. The invention also provides a preparation method and application of the fluorine-containing photoacid generator. The fluorine-containing photoacid generator and the photosensitive resin thereof have the beneficial effects that the fluorine-containing photoacid generator and the photosensitive resin thereof have low absorption and relatively high optical transparency at 193nm; and the thermal stability is relatively high. An acid generator is grafted to a polymer main chain to be copolymerized with other functional monomers, so that phase separation can be effectively reduced, H<+> generated by the acid generator is prevented from diffusing to an unexposed area, LER is reduced, light sensitivity and resolution are improved, and meanwhile, the fluorine-containing photoacid generator has the advantage of relatively low gas emission.

Description

technical field [0001] The invention relates to the technical field of photosensitive resin synthesis, in particular to a fluorine-containing photoacid generator and its preparation method and application. Background technique [0002] Photoresist is a basic chemical material in the integrated circuit industry, and photoresist is required to be continuously updated to meet the needs of its rapid development. As an important part of photoresist, film-forming resin is the bottleneck restricting the development of photoresist. Since the invention of the first photosensitive resin polyvinyl alcohol cinnamate (ultraviolet negative resist) by Kodak Company of the United States in 1954, it has created a precedent for photoresists used in integrated circuits, and with the development of the integrated circuit industry, the exposure light source is from G line (436nm), line (365nm) development of deep ultraviolet KrF (248nm), ArF (193nm) and vacuum ultraviolet 157nm, as well as EUV a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C309/42C07C303/32C07C381/12C08F220/18C08F220/38C08F220/32C08F212/14G03F7/004
CPCC07C309/42C07C381/12C08F220/1812G03F7/004C08F220/382C08F220/32C08F220/38C08F212/24
Inventor 董其宝符勇
Owner 安徽庆润新材料技术有限公司
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