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Onium salt compound, chemically amplified resist composition, and pattern forming method

A compound, onium salt technology, applied in the direction of organic chemistry, optics, photolithography process of pattern surface, etc., can solve the problems of inability to obtain photolithography performance and defects

Active Publication Date: 2021-05-21
SHIN ETSU CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, even when the following onium salts are used as acid diffusion inhibitors, in the generation requiring ultra-fine processing using ArF lithography and extreme ultraviolet (EUV) lithography, satisfactory performances and defects in various lithography cannot be obtained. the result of

Method used

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  • Onium salt compound, chemically amplified resist composition, and pattern forming method
  • Onium salt compound, chemically amplified resist composition, and pattern forming method
  • Onium salt compound, chemically amplified resist composition, and pattern forming method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-1

[0530][Example 1-1] Synthesis of an acid diffusion inhibitor Q-1

[0531](1) Synthesis of Compound SM-2

[0532][化 116]

[0533]

[0534]354.7 g of Compound SM-1 was mixed with 437.2 g of tert-butoxybenzoic acid, N, N-dimethylaminopyridine 66.5 g and methylene chloride 3,400 g, add N- (3-dimethylaminopropyl) The group) -N'-ethyl carbon diimine hydrochloride was 450.9 g for stirring at room temperature for 21 hours. use19F-NMR confirms that 5% by mass Nahco is added after completion of the reaction3The aqueous solution was 1,600 g and stirred, and the reaction was quenched. After separating the organic layer, add 1,600 g of pure water and 400 g of saturated saline, and wash it once. After the obtained organic layer was concentrated under reduced pressure, hexane 2,000 g was added to dissolve, and the organic layer was washed with pure water 1,000 g, 5% by weight of 1,000 g and pure water 1,000 g. The obtained organic layers were concentrated under reduced pressure, and the crude product was evap...

Embodiment 1-2

[0549][Example 1-2] Synthesis of an acid diffusion inhibitor Q-22

[0550](1) Synthesis of Compound SM-5

[0551]119]

[0552]

[0553]11.8 g of Compound SM-1, 14.8 g of Compound SM-4, N, N-dimethylaminopyridine 0.73 g and 70 g of dichloromethane were mixed, and N- (3-dimethylaminopropyl) was added. N'-ethyl carbon diimide hydrochloride was 13.8 g for stirring at room temperature for 60 hours. use19F-NMR confirmed that after the reaction was completed, 40 g of pure water was added and stirred, and the reaction was quenched. After separating the organic layer, washed 40 g of 2% by mass hydrochloric acid. Further, the organic layer was washed once at pure water 40g 40 g of a saturated aqueous solution of sodium hydrogencarbonate, washed once, and washed once in pure water, and washed with 40 g of saline. The obtained organic layer was added to the activated carbon 1.2 g and stirred for 60 hours, and the activated carbon was filtered, and the obtained filtrate was concentrated under reduced pressu...

Embodiment 1-3～1-22

[0568][Examples 1-3 ~ 1-22] Synthesis of acid diffusion inhibitors Q-2 ~ Q-21

[0569]Further, reference to the first 1-1 to 1-2, the following acid diffusion inhibitors Q-2 to Q-21 are synthesized.

[0570]122]

[0571]

[0572]123]

[0573]

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Abstract

The invention relates to an onium salt compound, a chemically amplified resist composition, and a pattern forming method. The present invention addresses the problem of providing: a chemically amplified resist composition which has excellent dissolution contrast, acid diffusion suppression ability, and excellent lithography performance such as CDU, LWR, and sensitivity in optical lithography using a high-energy ray such as a KrF excimer laser, an ArF excimer laser, an electron beam, or an extreme ultraviolet ray as a light source; the invention also provides an acid diffusion inhibitor used in the chemical amplification resist composition, and a pattern forming method using the chemical amplification resist composition. The solution of this problem is an onium salt compound represented by formula (1), an acid diffusion inhibitor comprising the onium salt compound, and a chemically amplified resist composition containing the acid diffusion inhibitor.

Description

Technical field[0001]The present invention relates to a phosphonium salt compound, a chemical amplitude resist composition, and a pattern forming method.Background technique[0002]In recent years, with the high intensification and high speed of LSI, the shortage of pattern rules is required, and as the high resolution resist pattern is gradually required, in addition to improving the pattern shape, contrast, mask error factor (Mask Error Factor (MEF )), Focus depth, size uniformity (CDU), line width roughness (Line Width Roughnes (LWR), etc., is further improved Deficing of the resist pattern after development.[0003]As one of the improvement means of photolithography, it is possible to use an acid diffusion inhibitor, in particular, such as a weak acid phosphonium salt of a weak acid, an inhibitory structure, and a solvent solubility adjustment. Further, by causing the additive ingredient other than the base polymer, it is tried to improve the contrast to the function of the solubili...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C381/12C07C69/80C07C25/18C07C69/92C07C69/96C07D309/12C07D333/76G03F7/004G03F7/039G03F7/32
CPCC07C381/12C07D309/12C07D333/76C07C69/92C07C69/96C07C69/80C07C25/18G03F7/004G03F7/039G03F7/322C07C2601/08C07C2603/74C07C2601/14G03F7/0045G03F7/325G03F7/0397C07C69/76C07C25/00C08F212/24C09D125/18C08F220/1809C08F220/1806C08F220/1808C08F212/22C08F220/1818C08F212/32C08F220/283C08F220/382C07C69/708G03F7/066G03F7/0384G03F7/0392G03F7/2004G03F7/26G03F7/32G03F7/0382
Inventor 藤原敬之及川健一小林知洋福岛将大
Owner SHIN ETSU CHEM CO LTD
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