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Sulfonium compound, resist composition, and patterning process

一种锍化合物、抗蚀剂的技术，应用在有机化学、图纹面的照相制版工艺、仪器等方向，能够解决含氟起始反应物昂贵、环境安全不能令人满意、不足以精确控制酸扩散等问题

Active Publication Date: 2018-03-13
SHIN ETSU CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the degree of fluorine substitution is reduced, these PAGs still have the following problems: Since they do not have decomposable substituents such as ester structures, they are not satisfactory in terms of environmental safety due to easy decomposability; Limited molecular design for sulfonic acid size; expensive fluorine-containing starting reactants
However, resist compositions containing this PAG are still insufficient to precisely control acid diffusion, and their lithographic performance is unsatisfactory when comprehensively evaluated in terms of LWR (as an indicator of pattern roughness) and resolution

Method used

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  • Sulfonium compound, resist composition, and patterning process
  • Sulfonium compound, resist composition, and patterning process
  • Sulfonium compound, resist composition, and patterning process

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-1

[0311] Embodiment 1-1: Synthesis of Intermediate A

[0312]

[0313] 220 g of 4-phenylthiophenol were dissolved in a mixture of 550 g THF and 133 g water. At room temperature, 25% by weight of caustic soda was added dropwise to the solution aged for 15 minutes. Thereafter, a solution of 352 g of Compound A dissolved in 250 g of THF was added dropwise thereto at room temperature. The solution was aged overnight, and then 5% by weight hydrochloric acid was added thereto for quenching. The reaction solution was diluted with 620 g of hexane and 620 g of toluene, and washed with water. 1% by weight of caustic soda was added to the organic layer, followed by separation. The organic layer was mixed with 2.5% by weight hydrochloric acid, washed with water again, and then separated. The organic layer was concentrated to obtain 208 g of the final compound, Intermediate A, as a colorless oil (yield 65%).

[0314] Intermediate A was analyzed by spectroscopy. figure 1 and 2 The...

Embodiment 1-2

[0317] Embodiment 1-2: the synthesis of intermediate B

[0318]

[0319] 183 g of Intermediate A were dissolved in 1300 g of acetic acid. Under ice cooling, 51 g of 35% by weight aqueous hydrogen peroxide was added to the solution. The solution was matured overnight at room temperature, and then a solution of 25 g of sodium thiosulfate dissolved in 120 g of water was added dropwise at room temperature. After stirring for 1 hour, the reaction solution was diluted with 2000 g of ethyl acetate and 1000 g of toluene, and washed with 1000 g of water. The organic layer was mixed with 1% by weight caustic soda, then separated. The organic layer was washed once with water, mixed with 2.5% by weight hydrochloric acid, and then separated. The organic layer was washed with water and concentrated, and ethyl acetate was added to the concentrate to form a 50% by weight ethyl acetate solution. The solution was added dropwise to a mixture of n-hexane and toluene (weight ratio 2:1) fo...

Embodiment 1-3

[0323] Example 1-3: Synthesis of Intermediate C

[0324]

[0325] 117 g of Intermediate B were dissolved in a mixture of 69 g of diisopropylethylamine and 590 g of acetonitrile. Under ice-cooling, 36 g of chloromethyl methyl ether was added dropwise to the solution. The solution was aged overnight at room temperature, then mixed with 800 g of water and 800 g of toluene, and then separated. The organic layer was washed once with water, washed with 1% by weight ammonia, and then washed with water again. The solution was further washed with 1% by weight hydrochloric acid, and washed with water. The organic layer was taken out and concentrated under reduced pressure. The obtained solid was dried in vacuo to obtain 127 g of the final compound, Intermediate C, as white crystals (yield 82%).

[0326] Intermediate C was analyzed by spectroscopy. Figure 5 and 6 The NMR spectrum is shown in DMSO-d 6 of 1 H-NMR and 19 F NMR. exist 1 In H-NMR analysis, a small amount of r...

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Abstract

A sulfonium salt containing an acid-eliminatable substituent group which is effective for improving contrast is highly soluble and uniformly dispersible. A resist composition comprising the sulfoniumsalt as photoacid generator forms a pattern with a high resolution, rectangularity, and reduced LWR.

Description

[0001] Cross References to Related Applications [0002] This non-provisional application claims priority under 35 U.S.C. §119(a) based on Patent Application No. 2016-169793 filed in Japan on August 31, 2016, the entire contents of which are incorporated herein by reference. technical field [0003] The present invention relates to a sulfonium compound, a resist composition containing the above sulfonium compound, and a pattern forming method using the above resist composition. Background technique [0004] Driven by higher integration and operating speed of LSI devices, efforts are recently being made to achieve finer pattern rules, while DUV and EUV lithography methods are considered to hold particular promise as next-generation microfabrication technologies. In particular, photolithography using an ArF excimer laser is necessary for a micropatterning technique capable of achieving a feature size of 0.13 μm or less. [0005] ArF lithography has been partially used since t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C381/12C07D327/08C07D333/76C07D339/08G03F7/004
CPCC07C381/12C07D327/08C07D333/76C07D339/08G03F7/004C07C2602/42C07C2603/68C07C2603/74G03F7/0046G03F7/0397G03F7/11G03F7/325G03F7/0045G03F7/322G03F7/038G03F7/2004G03F7/32C07C309/02C07C309/20G03F7/16G03F7/2041G03F7/2053G03F7/38
Inventor 三井亮藤原敬之谷口良辅长谷川幸士大桥正树
Owner SHIN ETSU CHEM CO LTD
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