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Compound, resin, composition, and pattern formation method

A compound and carbon number technology, applied in the direction of organic chemistry, photoengraving process of pattern surface, instruments, etc., can solve the problems of difficulty in obtaining resist pattern, resolution problem, resist pattern collapse, etc.

Inactive Publication Date: 2019-05-03
MITSUBISHI GAS CHEM CO INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In addition, if the miniaturization of the resist pattern is promoted, there will be problems such as resolution problems and resist pattern collapse after development, so it is desired to reduce the thickness of the resist.
However, it becomes difficult to obtain a film thickness of a resist pattern sufficient for substrate processing only by thinning the resist

Method used

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  • Compound, resin, composition, and pattern formation method
  • Compound, resin, composition, and pattern formation method
  • Compound, resin, composition, and pattern formation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0900] Hereinafter, this embodiment will be described in more detail based on synthesis examples, synthesis examples, examples, and comparative examples, but this embodiment is not limited to these examples.

[0901] (carbon concentration and oxygen concentration)

[0902] Carbon concentration and oxygen concentration (mass %) were measured by organic elemental analysis using the following apparatus.

[0903] Device: CHN CORDER MT-6 (manufactured by Yanac Analytical Industry Co., Ltd.)

[0904] (molecular weight)

[0905] The molecular weight of the compound was measured by LC-MS analysis using Acquity UPLC / MALDI-Synapt HDMS manufactured by Water Corporation.

[0906]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).

[0907] Device: Shodex GPC-101 (manufactured by Showa Denko Co....

Synthetic example 1

[0922] Synthesis of BiN-1

[0923] After melting 10 g (69.0 mmol) of 2-naphthol (reagent manufactured by Sigma-Aldrich) at 120° C. in a container with an internal volume of 300 mL equipped with a stirrer, a condenser, and a burette, 0.27 g of sulfuric acid was added, and 4-acetyl 2.7 g (13.8 mmol) of biphenyl (a reagent manufactured by Sigma-Aldrich Co., Ltd.) was stirred at 120° C. for 6 hours to react the contents to obtain a reaction liquid. Next, 100 mL of N-methyl-2-pyrrolidone (manufactured by Kanto Chemical Co., Ltd.) and 50 mL of pure water were added to the reaction liquid, followed by extraction with ethyl acetate. Next, pure water was added to separate the liquid until neutral, and then concentrated to obtain a solution.

[0924] The obtained solution was separated by column chromatography to obtain 1.0 g of a target compound (BiN-1) represented by the following formula (BiN-1).

[0925] The molecular weight of the obtained compound (BiN-1) was measured to be 466...

Synthetic example 2

[0929] Synthesis of BiP-1

[0930] Except that 2,2'-biphenol was used instead of 2-naphthol, the reaction was carried out in the same manner as in Synthesis Example 1 to obtain 0.1 g of the target compound represented by the following formula (BiP-1).

[0931] The molecular weight of the obtained compound (BiP-1) was measured to be 466 by the method described above.

[0932] The obtained compound (BiP-1) was subjected to NMR measurement under the above-mentioned measurement conditions. As a result, the following peak was observed, and it was confirmed that it had the chemical structure of the following formula (BiP-1).

[0933] δ(ppm)9.40(4H, O-H), 6.80~7.80(23H, Ph-H), 2.25(3H, C-H)

[0934]

[0935] Synthesis of Al-BiN-1

[0936] 9.8 g (21 mmol) of the compound represented by the above formula (BiN-1) and 6.2 g (45 mmol) of potassium carbonate were added to 100 mL of acetone in a container with an inner volume of 100 ml equipped with a stirrer, a condenser, and a bure...

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Abstract

The present invention provides a compound that is represented by formula (0). (In formula (0), RY is a C1-30 alkyl group or a C6-30 aryl group; RZ is a C1-60 N-valent group or a single bond; each RT is independently an optionally substituted C1-30 alkyl group, an optionally substituted C6-30 aryl group, an optionally substituted C2-30 alkenyl group, an optionally substituted C1-30 alkoxy group, ahalogen atom, a nitro group, an amino group, a carboxylic acid group, a thiol group, or a hydroxyl group, the alkyl group, the aryl group, the alkenyl group, and the alkoxy group optionally includingan ether linkage, a ketone linkage, or an ester linkage, at least one RT being a hydroxyl group, and at least one RT being a C2-30 alkenyl group; X is an oxygen atom, a sulfur atom, a single bond, orthe absence of a crosslink; each m is independently an integer from 0 to 9, at least one being an integer from 2 to 9 or at least two being integers from 1 to 9; N is an integer from 1 to 4, the structures inside the N [ ] being the same or different when N is 2 or greater; and each r is independently an integer from 0 to 2.)

Description

technical field [0001] The present invention relates to compounds and resins with specific structures and compositions containing them. In addition, it also relates to a pattern forming method using the composition. Background technique [0002] In the manufacture of semiconductor devices, microfabrication by photolithography using photoresist materials is performed, but in recent years, with the high integration and high speed of LSIs, further miniaturization by pattern rules 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 light (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. Therefore, roughness occurs on the surface of the pattern, mak...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/21C07D311/78C08G8/20G03F7/004G03F7/027G03F7/11G03F7/20
CPCC07D311/78C07C39/21C08G8/20G03F7/004G03F7/027G03F7/11G03F7/20C07C39/225C07C43/202
Inventor 越后雅敏
Owner MITSUBISHI GAS CHEM CO INC
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