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.
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[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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