Novel onium salt compound, acid amplifier derived therefrom, and resist composition comprising same

An acid enhancer and compound technology, which can be applied in the fields of organic chemistry, sulfonate preparation, photoengraving process of pattern surface, etc., and can solve problems such as few photons

Active Publication Date: 2014-05-07
SK MATERIALS PERFORMANCE CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, when the sensitivity (10-15mJ/cm 2 ), there is th

Method used

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  • Novel onium salt compound, acid amplifier derived therefrom, and resist composition comprising same
  • Novel onium salt compound, acid amplifier derived therefrom, and resist composition comprising same
  • Novel onium salt compound, acid amplifier derived therefrom, and resist composition comprising same

Examples

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preparation example Construction

[0133] Specifically, the compound of the chemical formula 3 can be prepared by the following preparation method, which includes the following steps: making the hydroxyl ring compound of the following chemical formula 5 and the sulfonyl halide of the following chemical formula 6 in the presence of a basic compound A step of reacting to obtain a compound of the following chemical formula 7; and a step of reacting the compound of the chemical formula 7 with a sulfoxide compound of the following chemical formula 8 and trifluoromethanesulfonic anhydride.

[0134] chemical formula 5

[0135]

[0136] chemical formula 6

[0137]

[0138] chemical formula 7

[0139]

[0140] chemical formula 8

[0141]

[0142] In said chemical formula,

[0143] R a , R b and R d same as defined above,

[0144] X is selected from the group consisting of an aryl group with 6 to 30 carbon atoms, a heteroaryl group with 5 to 30 carbon atoms, and a heterocycloalkyl group with 2 to 30 ca...

Synthetic example 1

[0256] In a round bottom flask, dissolve 6.9g of phenol and 23g of 3,5-bis-trifluoromethyl-benzenesulfonyl chloride in 200ml of dichloromethane Then, to the solution obtained by stirring, 8.9 g of triethylamine (triethylamine) was slowly added dropwise at normal temperature, and stirred for 2 hours. After confirming the completion of the reaction by TLC, the resulting reaction solution was washed with an aqueous sodium hydroxide solution and then twice with distilled water, and the organic layer was separated and collected. Obtained 3,5-bis-trifluoromethyl-benzenesulfonic acid phenyl ester (3,5-Bis-trifluoromethyl-benzenesulfonic acid phenyl ester) (i) after removing the solvent component in the collected organic layer with a vacuum distiller (22.2 g, 81% yield). The structure of the obtained compound was confirmed by 1H NMR.

[0257] 1 H NMR (CDCl 3 , internal standard: tetramethylsilane): (ppm) 7.00 (d, 2H), 7.3 ~ 7.4 (t, 3H), 8.2 (s, 1H), 8.3 (s, 1H)

[0258] Reaction 1 ...

Synthetic example 2

[0261] After putting 5 g of 3,5-bis-trifluoromethyl-benzenesulfonic acid phenyl ester (i) and 3 g of phenyl sulfone (phenyl sulfoxide) synthesized in the synthesis example 1 into a round bottom flask, as a reaction solvent Dissolution was performed using 50 ml of dichloromethane. After preparing an ice bath (bath) and cooling the reaction flask to -10°C, 4.8 g of trifluoromethanesulfonic anhydride (trifluoromethanesulfonic anhydride) was slowly dropped into the reactor. After completion of the dropwise addition, stirring was carried out for 2 hours while maintaining the internal temperature of the reactor at -10°C. After confirming the completion of the reaction with TLC, the reaction solution obtained as a result was added to potassium carbonate (K 2 CO 3 ) in the aqueous solution for vigorous stirring to neutralize. After the neutralization process was completed, it was washed twice with distilled water, and only the organic layer was separated and collected. The solvent...

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Abstract

Provided are a novel noium salt compound which is helpful in forming monomers of an acid amplifier, an acid amplifier containing repetitive units derived therefrom, and a resist composition comprising same. The noium salt compound has a structure described in Formula 1. The acid amplifier containing repetitive units derived therefrom, when being used as an additive during preparing a resist, shows a high acid yield in the same photosensibility, thereby raising the photosensibility of the resist and forming finest corrosion patterns having excellent photosensibility and distinguishability. The Formula 1 is described in the description. And in the Formula 1, all the substituent groups are the same as defined in the description.

Description

technical field [0001] The present invention relates to a novel onium salt compound useful as a monomer for forming an acid enhancer, an acid enhancer containing a repeating unit derived therefrom, and a resist composition containing the same. Background technique [0002] Recently, in lithography technology, mass production (HVM, high volume manufacturing) using ArF immersion lithography technology (immersion) is being actively carried out, and technology development for realizing a line width of 50 nm or less is mainly carried out. In addition, lithography using extreme ultraviolet (EUV, extreme UV) is expected to be the most likely candidate for next-generation technology. [0003] EUV lithography is a next-generation technology being researched mainly to realize patterns below 30nm, and is currently expected to be commercialized in all aspects except energy output and defects that occur in masks. In addition, in the International Semiconductor Technology Roadmap (ITRS r...

Claims

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Application Information

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IPC IPC(8): C07C381/12C07C303/32C07C309/12C07D333/46G03F7/00C08F220/28C08F220/32C08F220/38G03F7/004
CPCC07C309/29C07C321/10G03F7/004G03F7/0042G03F7/0045G03F7/0046
Inventor 朱炫相金真湖韩俊熙柳京辰
Owner SK MATERIALS PERFORMANCE CO LTD
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