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Novel acryl monomer, polymer, and resist composition comprising same

An acrylic and polymer technology, applied in the field of polymers for resist additives and resist compositions, can solve problems such as watermark defects

Active Publication Date: 2014-08-20
SK MATERIALS PERFORMANCE CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, since the resist film is directly in contact with water (pure water), the amine compound added to the resist film as an acid or a quencher (quencher) is easily dissolved in water due to the photoacid generator, so there is a change formed. Resist pattern shape or various defect phenomena such as pattern collapse due to expansion, bubble defect, or watermark defect, etc.

Method used

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  • Novel acryl monomer, polymer, and resist composition comprising same
  • Novel acryl monomer, polymer, and resist composition comprising same
  • Novel acryl monomer, polymer, and resist composition comprising same

Examples

Experimental program
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preparation example

[0263] Preparation Example: Synthesis of Monomers and Polymers

Synthetic example 1

[0265]

[0266] 30.0g of 2,2-bis(hydroxymethyl)propionic acid (2,2-bis(hydroxymethyl)propionic acid) and 41.4mL of 2,2-dimethoxypropane (2,2-dimethoxypropane) and 2.13 g of p-toluenesulfonic acid monohydrate (p-toluenesulfonic acid monohydrate) was put into 300 mL of acetone, and stirred at room temperature for 2 hours to prepare a mixed solution. After adding NH3 / EtOH solution to the resultant mixed solution for neutralization, the solvent was removed by a rotary concentrator. The resulting reactant was washed with methylene chloride and distilled water to obtain Compound 1.

[0267] 16g of 2-hydroxyethylmethacrylate (2-hydroxyethylmethacrylate) and 23.5g of the prepared compound 1 and 4.2g of dimethylaminopyridine (DMAP, dimethylaminopyridine) and 27.9g of N,N'-bicyclic Hexylcarbodiimide (DCC, N,N'-dicyclohexylcarbodimide) was mixed with 300mL of dichloromethane to prepare a mixed solution, and stirred at room temperature for 24 hours. Compound 2 was obtained by column ...

Synthetic example 2

[0275] The polymer, except for 1-(2-isopropyl-adamantan-2-yl)-3-methyl-but-3-en-2-one (1-(2-isopropyl-adamantan-2- yl)-3-methyl-but-3-en-2-one) to replace 2-methyl-acrylic acid 1-methylcyclohexyl ester (2-methyl-acrylic acid1-methyl-cyclohexyl ester) in Synthesis Example 1, Moreover, with 2-methacrylic acid 5-oxo-4-oxatricyclo[4.2.1.03,7]non-2-yl ester (2-methyl-acrylic acid5-oxo-4-oxa-tricyclo[4.2. 1.03,7]non-2-yl ester) substituted 2-methacrylic acid 2-oxo-tetrahydro-furan-3-yl ester (2-methyl-acrylic acid2-oxo-tetrahydro-furan-3-yl ester) Otherwise, the same method as in Synthesis Example 1 of the polymer was carried out to obtain a polymer (II) represented by the following chemical formula. The polystyrene equivalent weight average molecular weight Mw of this polymer was 11000 g / mol, and the molar ratio of each repeating unit was 1:m:n=35:35:30.

[0276]

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Abstract

The present invention relates to an acryl monomer of the following chemical formula 1, which is useful as a monomer for forming an anticorrosive additive, a polymer for anticorrosive additive including a repeating unit derived from the same and a resist composition including the same. The polymer includes a repeating unit derived from the acryl monomer of the following chemical formula 1. In performing a micromachining process by immersion lithography, the hydrophobicity of a surface of a resist film in an exposure process may be elevated, thereby inhibiting the resist film being digested by water. The resist film is changed into hydrophilic in a developing process after exposure, so that a surface of the resist film has a lower static contact angle, thereby a fine resist pattern having excellent photosensitivity and resolution can be formed. Chemical formula 1 (the definition of each substituent in the formula is as described in the description).

Description

technical field [0001] The present invention relates to novel acrylic monomers for forming resist additives, polymers for resist additives containing repeating units derived therefrom, and resist compositions containing the same. Background technique [0002] Recently, with the high integration and high speed of large-scale integrated circuits (LSI, large scale integrated circuit), miniaturization of photoresist patterns is required. As an exposure light source for forming a resist pattern, g-rays (436 nm) such as mercury or i-rays (365 nm) are mainly used. [0003] However, the resolution by increasing the exposure wavelength is actually approaching the limit, and as a method of forming a finer resist pattern, a method of shortening the wavelength has been proposed. As a specific example, short-wavelength KrF excimer laser light (248 nm), ArF excimer laser light, or the like is used instead of i-rays (365 nm). [0004] The ArF immersion lithography method using an ArF exc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/67G03F7/004G03F7/00C08F220/28C08F220/32
CPCC07C69/67C08F220/18C08F220/28C08F220/282G03F7/004C08F220/32C07C57/04C08F20/10G03F7/0045G03F7/0046G03F7/20G03F7/2002
Inventor 裵昌完金三珉尹队卿柳印泳黃晳浩
Owner SK MATERIALS PERFORMANCE CO LTD
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