Material for forming organic film, substrate, method for forming organic film, patterning process, and compound for forming organic film
An organic film and compound technology, applied in the field of organic film-forming compounds, can solve the problems of insufficient filling properties and flattening properties, and achieve the effects of excellent adhesion and high heat resistance
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[0337] Hereinafter, the present invention will be described more specifically by illustrating synthesis examples, comparative synthesis examples, examples, and comparative examples, but the present invention is not limited thereto. In addition, in terms of molecular weight and degree of dispersion, polystyrene-equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) were obtained by gel permeation chromatography (GPC) using tetrahydrofuran as an eluent. , and obtain the degree of dispersion (Mw / Mn).
Synthetic example
[0338] Synthesis Example Synthesis of Compounds for Organic Membrane Materials
[0339] Compounds (A1) to (A19) for organic membrane materials were synthesized using aniline derivatives B: (B1) to (B5) and tetracarboxylic dianhydrides C: (C1) to (C11) shown below.
[0340] Aniline derivatives:
[0341] [chemical 50]
[0342]
[0343] Tetracarboxylic dianhydrides:
[0344] [Chemical 51]
[0345]
[0346] The following chemical formulas are considered to have three isomer structures such as the following (1) to (3) when producing an amic acid compound using, for example, tetracarboxylic dianhydride (C1) and aniline derivative (B1). Therefore, with respect to the amic acid compound and the amic acid ester compound derived from amic acid having the same isomer structure, one of the isomer structures is designated as a representative structure.
[0347] [Chemical 52]
[0348]
Synthetic example 1
[0349] [Synthesis Example 1] Synthesis of Compound (A1)
[0350] Add 100g of N-methyl-2-pyrrolidone to 15.51g of (C1), make a homogeneous solution at an internal temperature of 40°C under a nitrogen atmosphere, and slowly add the solution that has been dissolved in N-methyl-2-pyrrolidone in advance dropwise. 11.72 g of 30 g of (B1) was reacted at internal temperature 40 degreeC for 3 hours, and an amic-acid solution was obtained. After adding 3.96 g of pyridine to the obtained amic-acid solution, and adding 12.25 g of acetic anhydride slowly, reaction was implemented at internal temperature 60 degreeC for 4 hours, and imidization was performed. After completion of the reaction, cool to room temperature and add 300 g of methyl isobutyl ketone, wash the organic layer with 100 g of 3% aqueous nitric acid solution, wash with 100 g of pure water 6 times, and dry the organic layer under reduced pressure. After adding 100 g of THF (tetrahydrofuran) to the residue to obtain a homogen...
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