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Fluorine-containing sulfonates having polymerizable anions and manufacturing method therefor, fluorine-containing resins, resist compositions, and pattern-forming method using same

A kind of polymerization and sulfonate technology, which is applied in the preparation of sulfonate, the application of radioactive source radiation, the photoplate making process of pattern surface, etc., which can solve the problems of expensive sulfonic acid and so on

Inactive Publication Date: 2013-07-31
CENT GLASS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, all sulfonic acids are manufactured using expensive raw materials through complicated processes, and there are problems in industrial use

Method used

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  • Fluorine-containing sulfonates having polymerizable anions and manufacturing method therefor, fluorine-containing resins, resist compositions, and pattern-forming method using same
  • Fluorine-containing sulfonates having polymerizable anions and manufacturing method therefor, fluorine-containing resins, resist compositions, and pattern-forming method using same
  • Fluorine-containing sulfonates having polymerizable anions and manufacturing method therefor, fluorine-containing resins, resist compositions, and pattern-forming method using same

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Experimental program
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Effect test

Embodiment

[0318] Hereinafter, the present invention will be described in detail using synthesis examples, examples, and reference examples, but the present invention is not limited to the following examples.

[0319] First, two types of polymerizable monomers were synthesized in the following procedure.

Synthetic example 1-1

[0320] [Synthesis Example 1-1] Production of Methacryloyloxyacetyl Chloride

[0321]

[0322] In a 100mL reactor equipped with a condenser, 30g (purity 46%, 95.1mmol) methacryloyloxyacetic acid (there is a description of the production method in the International Publication No. 96 / 41842 pamphlet, etc.), 347mg (4.8 47.6 g (380.5 mmol / 4.0 equivalent) of thionyl chloride was added dropwise to dimethylformamide in mmol / 0.05 equivalent, and stirred at 70° C. for 1 hour. Then, purification was carried out by distillation to obtain 10.0 g of the target methacryloxyacetyl chloride. At this point the purity was 70%, and the yield was 45%.

[0323] [Physical properties of methacryloyloxyacetyl chloride] 1 H NMR (measurement solvent: deuterated chloroform, reference substance: tetramethylsilane): δ=6.22(s, 1H), 5.70(s, 1H), 4.96(s, 2H; CH 2 ), 1.97(s, 3H; CH 3 ).

Synthetic example 1-2

[0324] [Synthesis Example 1-2] Production of 2-bromo-2,2-difluoroethyl trimethylacetate

[0325]

[0326] Into a glass flask equipped with a thermometer, condenser, and dropping funnel were charged 271 g (2.24 mol) of trimethylacetyl chloride, 360 g (2.23 mol) of 2-bromo-2,2-difluoroethanol and 1.5 L of diisopropyl ether and stir. Then, 318 g (3.14 mol) of triethylamine was added dropwise in an ice bath. After completion of the dropwise addition, stirring was continued at room temperature for 1 hour, and the termination of the reaction was confirmed by gas chromatography. 300ml of water was added to the reaction solution to dissolve the entire reaction solution, and then 500ml of 2N hydrochloric acid was added. After separating the organic layer and the aqueous layer, the aqueous layer was extracted with 500 ml of diisopropyl ether. Next, the organic phase was washed with 500 ml of saturated brine, and dried over anhydrous sodium sulfate. Then, the solvent was distilled...

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Abstract

According to the present invention, there is provided a polymerizable fluorine-containing sulfonic acid onium salt of the following general formula (2) and a resin obtained by polymerization thereof. It is possible by the use of this sulfonate resin of the present invention to provide a resist composition with high resolution, board depth of focus tolerance (DOF), small line edge roughness (LER) and high sensitivity. In the formula, Z represents a substituted or unsubstituted C1-C6 straight or branched alkylene group, or a divalent moiety in which substituted or unsubstituted C1-C6 straight or branched alkylene groups are bonded in series to a divalent group obtained by elimination of two hydrogen atoms from an alicyclic or aromatic hydrocarbon; R represents a hydrogen atom, a halogen atom, or a C1-C3 alkyl or fluorine-containing alkyl group; and Q+ represents a sulfonium cation or an iodonium cation.

Description

technical field [0001] The present invention relates to a novel fluorine-containing sulfonate having a polymerizable anion, a method for producing the same, a fluorine-containing resin, a resist composition, and a pattern forming method using the same. In particular, it relates to a resist composition which can be suitably used as a chemically amplified resist useful for microprocessing, a novel fluorine-containing resin which can be used in the resist composition, and a novel fluorine-containing sulfonic acid which can be used for synthesizing a fluorine-containing resin Salts and production methods thereof, the micro-processing uses KrF excimer lasers, ArF excimer lasers, F 2 Excimer lasers such as excimer lasers or high-energy rays such as near ultraviolet rays, far ultraviolet rays, extreme ultraviolet rays (EUV), soft X-rays, X-rays, gamma rays, or charged particle beams such as electron beams generated by synchrotron radiation. Background technique [0002] In recent ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F20/38C07C303/32C07C309/12C07C381/12G03F7/004G03F7/038G03F7/039H01L21/027
CPCG03F7/0397Y10S430/108G03F7/0046G03F7/2041G03F7/30C07C309/12Y10S430/111C08F220/38C08F220/24G03F7/0382C07C309/20C07C303/32G03F7/0045C07C381/12C08F220/382C08F220/20H01L21/0277
Inventor 增渕毅森和规萩原勇士成塚智前田一彦
Owner CENT GLASS CO LTD