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Alcohol compound, chemically amplified negative resist composition, and resist pattern forming method

An alcohol compound, chemical amplification technology, applied in the direction of organic chemistry, optics, photolithography process of pattern surface, etc., can solve the problem of line edge roughness, line width, roughness, size uniformity deterioration, insufficient insolubilization of base polymer, polymer Insufficient insolubilization and other problems, to achieve the effect of excellent limit resolution, excellent insolubilization, and reduced solubility

Pending Publication Date: 2022-06-24
SHIN ETSU CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the case of a negative resist composition using an alkaline developer, an acid is generated in the exposed part, and the base polymer is insolubilized by the action of the acid, but the crosslinkability may decrease due to the structure of the polymer. The insolubilization of the polymer becomes insufficient, and the limit resolution deteriorates
In addition, the acid and alkali developer generated in the exposed part have a high affinity, and the exposed part will dissolve during development, so the line edge roughness (LER), line width roughness (LWR), and dimensional uniformity (CDU) will deteriorate. will be a problem
In addition, when the control of acid diffusion is insufficient, the insolubilization of the base polymer becomes insufficient due to the diffusion of acid from the exposed part to the unexposed part. The alkali solubility of the unexposed part decreases and becomes a problem of scum (scum)

Method used

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  • Alcohol compound, chemically amplified negative resist composition, and resist pattern forming method
  • Alcohol compound, chemically amplified negative resist composition, and resist pattern forming method
  • Alcohol compound, chemically amplified negative resist composition, and resist pattern forming method

Examples

Experimental program
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preparation example Construction

[0147] As shown in Scheme A, the first step in the synthesis of compound A1-1 is to react the intermediate In-A, which can be obtained in the form of a commercial product or can be synthesized by a known organic synthesis method, with a Grignard reagent or an organolithium reagent to obtain Procedure for intermediate In-B. The reaction can be carried out by a known organic synthesis method. Specifically, the Grignard reagent or the organolithium reagent is diluted in a solvent such as tetrahydrofuran (THF) and diethyl ether, and a solution obtained by dissolving the intermediate In-A in a solvent such as THF and diethyl ether is added dropwise thereto. reaction. The amount of Grignard reagent or organolithium reagent used should be (2m 1 +2) Equivalent. The reaction temperature is preferably in the range from room temperature to about the boiling point of the solvent used. When the reaction time is followed by gas chromatography (GC) or silica gel thin layer chromatography...

Embodiment 1-1

[0335] [Example 1-1] Synthesis of crosslinking agent CA-1

[0336] (1) Synthesis of intermediate In-1

[0337] [Chemical 61]

[0338]

[0339]Under a nitrogen atmosphere, the Grignard reagent prepared from magnesium (145.9 g, 6 equivalents relative to M-1), THF (3,000 g) and methyl chloride was measured in the flask at the temperature in the flask (hereinafter referred to as the internal temperature). The solution which consists of M-1 (210g) and THF (500g) was dripped in the range of 40-55 degreeC. After the dropwise addition, it was aged for 3 hours at an internal temperature of 50°C. After aging, the reaction system was cooled, and a mixed aqueous solution of ammonium chloride (600 g) and a 3.0 mass % aqueous hydrochloric acid solution (1,800 g) was added dropwise to stop the reaction. Then, extraction was carried out with ethyl acetate (2,000 mL), the usual aqueous work-up was carried out, the solvent was distilled off, and In-1 was obtained as white crystals by recr...

Embodiment 1-2～1-15

[0346] [Examples 1-2 to 1-15] Synthesis of cross-linking agents CA-2 to CA-15

[0347] In addition, the crosslinking agents CA-2 to CA-15 were synthesized by the same organic synthesis method.

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Abstract

The invention relates to an alcohol compound, a chemically amplified negative resist composition and a resist pattern forming method. The present invention addresses the problem of providing: a photosensitive resin composition which has high sensitivity and excellent dissolution contrast; the present invention relates to a chemically amplified negative resist composition which is capable of providing a pattern having a small LER and CDU and a good shape, an alcohol compound suitable as a crosslinking agent used in the chemically amplified negative resist composition, and a resist pattern forming method using the chemically amplified negative resist composition. The solution of this problem is an alcohol compound represented by formula (A1).

Description

【Technical field】 [0001] The present invention relates to an alcohol compound, a chemically amplified negative resist composition, and a method for forming a resist pattern. 【Background technique】 [0002] Along with the high integration and high speed of LSIs, the miniaturization of pattern rules is also rapidly progressing. In particular, the expansion of the flash memory market and the increase in memory capacity are leading to miniaturization. As far as the most advanced miniaturization technology is concerned, the mass production of devices at the 65nm node using ArF lithography is already underway, and preparations for the next era of mass production at the 45nm node using ArF immersion lithography are in progress . For the 32nm node in the next era, there is an immersion lithography using an ultra-high NA lens that combines a liquid with a higher refractive index than water, a high-refractive-index lens, and a high-refractive-index resist composition. . In recent ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/23C07D493/18C07D307/00C07D495/18C07C69/712C07C69/78G03F7/038
CPCC07C43/23C07D493/18C07D307/00C07D495/18C07C69/712C07C69/78G03F7/038C07C69/82C07C69/44C07C69/76G03F7/0382G03F7/0045G03F7/0046C08F212/24C08F220/24C09D125/18C08F8/00C08F232/08C08F220/382C08F212/32C08F220/26C07C43/20C07C43/263C08K5/0016C08K5/06C08F220/301C08F220/302C08F220/22C08F2/44G03G7/004G03F7/2004G03F7/32G03F7/2006G03F7/327G03F7/38G03F7/40
Inventor 井上直也渡边聪小竹正晃
Owner SHIN ETSU CHEM CO LTD
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