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Resin having fluorene structure and underlayer film-forming material for lithography

A technology of resin and benzofluorene, which is applied in the field of the lower layer film for lithography, and achieves the effects of high heat resistance, high solvent solubility, and high carbon concentration

Inactive Publication Date: 2014-05-28
MITSUBISHI GAS CHEM CO INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the technology of Patent Document 8 needs improvement in heat resistance and etching resistance

Method used

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  • Resin having fluorene structure and underlayer film-forming material for lithography
  • Resin having fluorene structure and underlayer film-forming material for lithography
  • Resin having fluorene structure and underlayer film-forming material for lithography

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0220] Hereinafter, the present invention will be described in more detail based on synthesis examples and examples, but the present invention is not limited to these examples.

[0221] · Carbon concentration and oxygen concentration in the resin

[0222] The carbon concentration and oxygen concentration (mass %) in the resin were measured by organic elemental analysis.

[0223] Device: CHN CORDER MT-6 (manufactured by Yanaco Analytical Industry Co., Ltd.)

[0224] ·Molecular weight

[0225] The polystyrene-equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) were determined by gel permeation chromatography (GPC) analysis, and the degree of dispersion (Mw / Mn) was determined.

[0226] Device: Shodex GPC-101 (manufactured by Showa Denko Co., Ltd.)

[0227] Chromatographic column: KF-80M×3

[0228] Eluent: THF1ml / min

[0229] Temperature: 40°C

[0230] ·Structural analysis

[0231] Structural analysis was carried out in combination with ...

Synthetic example 1

[0259] Into a 200-ml three-necked flask with an internal volume equipped with a serpentine condenser, a thermometer, and a stirring blade, 33 g (0.2 mol) of fluorene (manufactured by Acros Organics) was added under nitrogen flow, and the temperature was raised to 230° C. for 12 hours. 2 ml of methanesulfonic acid (manufactured by Kanto Chemical Co., Ltd.) was added to the reaction liquid at intervals of 1 hour from the beginning of the reaction, and a total of 8 additions were made. Then, 80 g of methyl isobutyl ketone (manufactured by Kanto Chemical Co., Ltd.) and 40 g of anisole (manufactured by Kanto Chemical Co., Ltd.) were added to the reaction solution to dilute, neutralized and washed with water, and the solvent was removed under reduced pressure, thereby 13 g of resin (NF-1) of synthesis example 1 which is a target object were obtained.

[0260] As a result of GPC analysis, Mn: 830, Mw: 3040, Mw / Mn: 3.66. As a result of organic element analysis, the carbon concentrati...

Synthetic example 2

[0263] Into a four-neck flask with an internal volume of 1 L equipped with a serpentine condenser, a thermometer, and a stirring blade, 128 g (1.0 mol) of naphthalene (manufactured by Kanto Chemical Co., Ltd.) and 9-fluorenone (manufactured by Acros Organics) were added under a nitrogen stream. 180 g (1.0 mol), heated up to 230° C. and reacted for 8 hours. 2.5 ml of methanesulfonic acid (manufactured by Kanto Chemical Co., Ltd.) was added to the reaction solution at intervals of 1 hour from the beginning of the reaction, and a total of 8 additions were made. Then, 400 g of methyl isobutyl ketone (manufactured by Kanto Chemical Co., Ltd.) and 200 g of anisole (manufactured by Kanto Chemical Co., Ltd.) were added to the reaction solution to dilute, neutralized and washed with water, and the solvent was removed under reduced pressure, thereby 200 g of resin (NF-2) of the synthesis example 2 which is a target object was obtained.

[0264] As a result of GPC analysis, Mn: 625, Mw:...

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Abstract

Provided are: a resin having a novel fluorene structure which has a relatively high carbon concentration in the resin, relatively high heat resistance and relatively high solubility in solvents and which is applicable to a wet process; a method for producing the resin having a novel fluorene structure; an underlayer film-forming material which is useful for forming, as an underlayer film for multilayer resists, a novel resist underlayer film that has excellent heat resistance and excellent etching resistance; a pattern forming method which uses the material; and the like. A resin of the present invention has a structure represented by general formula (1). (In general formula (1), each of R3 and R4 independently represents a benzene ring or a naphthalene ring; the carbon atom in the bridgehead position of a fluorene skeleton or a (di)benzofluorene skeleton is bonded with a carbon atom in another aromatic ring; and a carbon atom in an aromatic ring of the fluorene skeleton or the (di)benzofluorene skeleton is bonded with the carbon atom in the bridgehead position of another fluorene skeleton or another (di)benzofluorene skeleton.)

Description

technical field [0001] The present invention relates to a resin having a fluorene structure useful in a multilayer resist process used in microfabrication in the production process of semiconductor elements and the like, and a production method thereof. In addition, the present invention relates to a resin composition containing the resin, an underlayer film-forming material for lithography, an underlayer film for lithography formed from the underlayer film-forming material for lithography, and a pattern forming method using the material. Background technique [0002] The reaction of phenols and formaldehyde in the presence of an acidic catalyst is generally known as a reaction for producing novolak resins and the like. Also, it is disclosed that polyphenols are produced by reacting aldehydes such as acetaldehyde, propionaldehyde, isobutyraldehyde, crotonaldehyde, and benzaldehyde (see Patent Document 1) and novolak resins (see Patent Document 2). In addition, it is disclos...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/02C08L65/00G03F7/11H01L21/027
CPCC08G61/02C08L65/00G03F7/11C08G2261/3142H01L21/31116H01L21/31138H01L21/31144G03F7/40C08G2261/314C08G2261/592C08G61/12G03F7/0041G03F7/094
Inventor 东原豪内山直哉越后雅敏
Owner MITSUBISHI GAS CHEM CO INC
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