Compound, resin, composition, resist pattern forming method and pattern forming method

A technology of compounds and compositions, which is applied in the fields of compounds, resins, compositions, and resist pattern formation and pattern formation, can solve problems such as difficult to obtain resist pattern film thickness, and achieve good formability and good resist pattern High effect of shape and solubility

Inactive Publication Date: 2019-05-21
MITSUBISHI GAS CHEM CO INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, when simply thinning the resist, it is difficult to obtain a film thickness of the resist pattern sufficient for substrate processing.

Method used

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  • Compound, resin, composition, resist pattern forming method and pattern forming method
  • Compound, resin, composition, resist pattern forming method and pattern forming method
  • Compound, resin, composition, resist pattern forming method and pattern forming method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0342] Hereinafter, this embodiment will be described in more detail with reference to synthesis examples and examples, but this embodiment is not limited to these examples at all.

[0343] (carbon concentration and oxygen concentration)

[0344] Carbon concentration and oxygen concentration (mass %) were measured by organic elemental analysis using the following apparatus.

[0345] Device: CHNCORDERMT-6 (manufactured by YanacoCo., Ltd.)

[0346] (molecular weight)

[0347] The molecular weight of the compound was measured by LC-MS analysis using Acquity UPLC / MALDI-Synapt HDMS manufactured by Water Corporation.

[0348] In addition, gel permeation chromatography (GPC) analysis was carried out under the following conditions to obtain polystyrene-equivalent weight average molecular weight (Mw), number average molecular weight (Mn), and degree of dispersion (Mw / Mn).

[0349] Device: Shodex GPC-101 (manufactured by Showa Denko Co., Ltd.)

[0350] Column: KF-80M×3

[0351] Elu...

Synthetic example 1

[0379] A four-neck flask with an internal volume of 10 L and a detachable bottom equipped with a serpentine condenser, a thermometer, and a stirring blade was prepared. In this four-necked flask, 1.09 kg (7 mol, manufactured by Mitsubishi Gas Chemical Co., Ltd.) of 1,5-dimethylnaphthalene was added to 2.1 kg (28 mol as formaldehyde) of 40% by mass formalin solution in a nitrogen stream. , manufactured by Mitsubishi Gas Chemical Co., Ltd.) and 0.97 mL of 98% by mass sulfuric acid (manufactured by Kanto Chemical Co., Ltd.), were reacted under normal pressure at 100° C. for 7 hours while refluxing. Thereafter, as a diluting solvent, 1.8 kg of ethylbenzene (Special grade manufactured by Wako Pure Chemical Industries, Ltd.) was added to the reaction liquid, and after standing still, the aqueous phase of the lower layer was removed. Further, neutralization and water washing were performed, and ethylbenzene and unreacted 1,5-dimethylnaphthalene were distilled off under reduced pressu...

Embodiment 1～2、 Embodiment 1A～2A

[0383] (Examples 1-2, Examples 1A-2A, Comparative Example 1)

[0384] With regard to the aforementioned BiF-1, BiF-3, and CR-1, the solubility of each was evaluated. The results are shown in Table 1.

[0385] Separately, underlayer film-forming materials for lithography having the compositions shown in Table 1 were prepared. Next, the material for forming an underlayer film for lithography was spin-coated on a silicon substrate, and then baked at 240°C for 60 seconds, and further baked at 400°C for 120 seconds to form an underlayer film with a film thickness of 200 nm. . For acid generators, crosslinking agents and organic solvents, the following were used.

[0386] Acid generator: Di-tert-butyldiphenyliodonium nonafluoromethanesulfonate (DTDPI) manufactured by Midori Kagaku Co., Ltd.

[0387] ・Crosslinking agent: NIKALAC MX 270 (Nikalac) manufactured by Sanwa Chemical Co., Ltd.

[0388] Organic solvent: propylene glycol monomethyl ether acetate (PGMEA)

[0389] [etching...

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Abstract

A compound selected from a group consisting of compounds represented by expression (1) is provided. (In expression (1), the RS's are independently a hydrogen atom, an alkyl group of 1-30 carbons optionally having a substituent, an aryl group of 6-30 carbons optionally having a substituent, an alkenyl group of 2-30 carbons optionally having a substituent, an alkoxy group of 1-30 carbons optionallyhaving a substituent, a halogen atom, a nitro group, an amino group, a carboxylic acid group, a thiol group or a hydroxy group, with the aforementioned alkyl group, aryl group, alkenyl group and alkoxy group optionally containing an ether bond, a ketone bond or an ester bond, and at least one RS's is a hydroxy group, the RT's are independently a hydrogen atom, an alkyl group of 1-30 carbons optionally having a substituent, an aryl group of 6-30 carbons optionally having a substituent, an alkenyl group of 2-30 carbons optionally having a substituent, an alkoxy group of 1-30 carbons optionally having a substituent, a halogen atom, a nitro group, an amino group, a carboxylic acid group, a thiol group or a hydroxy group, with the aforementioned alkyl group, aryl group, alkenyl group and alkoxygroup optionally including an ether bond, a ketone bond or an ester bond, and optionally including an annular structure through two RT's bonding together.)

Description

technical field [0001] The present invention relates to a compound having a specific structure, a resin, a composition, and a method for forming a resist pattern and a method for forming a circuit pattern. Background technique [0002] In the manufacture of semiconductor devices, microfabrication is performed by photolithography using a photoresist material, but in recent years, along with the high integration and high speed of LSI, further miniaturization by pattern rule is required. In addition, the light source for lithography used in resist pattern formation has been shortened from KrF excimer laser (248nm) to ArF excimer laser (193nm), and the introduction of extreme ultraviolet (EUV, 13.5nm) is also expected. [0003] However, in photolithography using conventional polymer resist materials, the molecular weight is as large as 10,000 to 100,000, and the molecular weight distribution is also wide, resulting in roughness on the surface of the pattern, making it difficult ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/08C08G16/00G03F7/004G03F7/031G03F7/038G03F7/039G03F7/11G03F7/20G03F7/26H01L21/027
CPCC07D493/08G02B1/043C08G16/0256G03F7/0226G03F7/094G03F7/0397H05K3/287H05K3/064G03F7/004G03F7/031G03F7/038G03F7/039G03F7/11G03F7/20G03F7/26H01L21/027H01L21/311C07D307/92C07D493/04C08G16/0262C09D161/00G02B1/04G03F7/168G03F7/2037G03F7/322G03F7/38H01L21/0274H01L21/30604H01L21/3081H01L21/3086
Inventor 越后雅敏
Owner MITSUBISHI GAS CHEM CO INC
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