1-methoxypropan-2-yl acetate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 432 g of propyleneglycol monomethyl ether acetate and 13 g of azobisisobutyronitrile were poured into a five-necked reaction vessel having a capacity of one litter. Then, while introducing nitrogen gas into the reaction vessel, the resultant mixture was heated to 80° C. Then, a mixed liquid constituted by 96.3 g of styrene and 11.8 g of acrylic acid was added drop-wise to the above mixture taking two hours. 30 minutes after finishing of the dropping of the mixed liquid, 6.5 g of azoisobutyronitrile was added to the resultant mixture and the mixture thus obtained was heated for 5 hours to obtain a styrene-acrylic acid copolymer. The weight average molecular weight of the styrene-acrylic acid copolymer thus obtained was 3000. Then, while introducing nitrogen gas into the reaction vessel was added drop-wise to the above mixture 30 minutes the mixture thus obtained was heated for 5 hours

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 432 g of propyleneglycol monomethyl ether acetate and 13 g of azobisisobutyronitrile were poured into a five-necked reaction vessel having a capacity of one litter. Then, while introducing nitrogen gas into the reaction vessel, the resultant mixture was heated to 80° C. Then, a mixed liquid constituted by 98.9 g of styrene and 9.1 g of acrylic acid was added drop-wise to the above mixture taking two hours. 30 minutes after finishing of the dropping of the mixed liquid, 6.5 g of azoisobutyronitrile was added to the resultant mixture and the mixture thus obtained was heated for 5 hours to obtain a styrene-acrylic acid copolymer. The weight average molecular weight of the styrene-acrylic acid copolymer thus obtained was 3100. Then, while introducing nitrogen gas into the reaction vessel was added drop-wise to the above mixture 30 minutes the mixture thus obtained was heated for 5 hours

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 320 g of propylene glycol monomethyl ether acetate (PGMEA) was dissolved 70 g of poly(p-hydroxystyrene) (VP-8000, manufactured by Nippon Soda Co., Ltd.) with heating and the solution was subjected to dehydration by distillation under a reduce pressure and cooled to 20° C. To the solution were added 0.35 g of pyridinium p-toluenesulfonate and 22.4 g of 2-cyclohexylethanol. Then, 17.5 g of tert-butyl vinyl ether was gradually added to the solution, followed by reacting at 20° C. for 5 hours. To the reaction mixture were added 0.28 g of triethylamine and 320 ml of ethyl acetate and the mixture was washed three times with each 150 ml of distilled water. The solvent was distilled off to concentrate, the resulting oily substance was dissolved in 100 ml of acetone and the solution was gradually poured into 2 liters of distilled water. The powder thus-deposited was collected by filtration and dried to obtain 54 g of the desired compound. The Mw of the resin was 12,000 and the molecular weight distribution (Mw/Mn) thereof was 1.1. with heating the solution was subjected to dehydration by distillation under a reduce pressure To the solution were added 0.35 g of pyridinium p-toluenesulfonate and 22.4 g of 2-cyclohexylethanol Then, 17.5 g of tert-butyl vinyl ether was gradually added to the solution To the reaction mixture were added 0.28 g of triethylamine and 320 ml of ethyl acetate the mixture was washed three times with each 150 ml of distilled water The solvent was distilled off to concentrate the resulting oily substance was dissolved in 100 ml of acetone the solution was gradually poured into 2 liters of distilled water The powder thus-deposited was collected by filtration dried

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 1000 ml glass flask, to a mixture of 150 g of methanol, 22 g of 2-(3,4-epoxycyclohexyl) ethyl trimethoxy silane, 77 g of trimethoxymethyl silane, 14 g of phenyl trimethoxy silane, and 1.5 g of oxalic acid was added dropwise a mixed solution of 40 g of deionized water and 20 g of methanol at a liquid temperature of 40 degrees C. After that, this solution was stirred for 12 hours at 40 degrees C. After the reaction finished, the solvent was removed under a reduced pressure. Thus-obtained residue was dissolved in 1000 ml of ethyl acetate, and washed with deionized water for washing. After the water layer was separated, the organic layer was washed twice with deionized water. To this organic layer was added 600 g of propylene glycol monomethyl ether acetate (PGMEA), and the contents were heated up to a liquid temperature of 40 degrees C. under a reduced pressure to remove ethyl acetate and to give a PGMEA solution of a polymer. the solvent was removed under a reduced pressure Thus-obtained residue was dissolved in 1000 ml of ethyl acetate washed with deionized water for washing After the water layer was separated the organic layer was washed twice with deionized water To this organic layer was added 600 g of propylene glycol monomethyl ether acetate (PGMEA) the contents were heated up to a liquid temperature of 40 degrees C under a reduced pressure to remove ethyl acetate

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 1000 ml glass flask, to a mixture of 150 g of methanol, 22 g of 2-(3,4-epoxycyclohexyl) ethyl trimethoxy silane, 77 g of trimethoxymethyl silane, 14 g of phenyl trimethoxy silane, and 1.5 g of oxalic acid was added dropwise a mixed solution of 40 g of deionized water and 20 g of methanol at a liquid temperature of 40 degrees C. After that, this solution was stirred for 12 hours at 40 degrees C. After the reaction finished, the solvent was removed under a reduced pressure. Thus-obtained residue was dissolved in 1000 ml of ethyl acetate, and washed with deionized water for washing. After the water layer was separated, the organic layer was washed twice with deionized water. To this organic layer was added 600 g of propylene glycol monomethyl ether acetate (PGMEA), and the contents were heated up to a liquid temperature of 40 degrees C. under a reduced pressure to remove ethyl acetate and to give a PGMEA solution of a polymer. the solvent was removed under a reduced pressure Thus-obtained residue was dissolved in 1000 ml of ethyl acetate washed with deionized water for washing After the water layer was separated the organic layer was washed twice with deionized water To this organic layer was added 600 g of propylene glycol monomethyl ether acetate (PGMEA) the contents were heated up to a liquid temperature of 40 degrees C under a reduced pressure to remove ethyl acetate

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 3000 ml glass flask, 1400 g of ethanol, 700 g of pure water, and 50 g of 25% tetraethylammonium hydroxide were placed, and stirred. To this mixture was added dropwise a mixture of 79 g of 2-(3,4-epoxycyclohexyl) ethyl trimethoxy silane, 70 g of tetraethoxy silane, and 14 g of phenyl trimethoxy silane at a liquid temperature of 40 degrees C. After that, the solution was stirred for 2 hours at 40 degrees C. After the reaction finished, the reaction was quenched by adding 35 g of acetic acid, and ethanol was removed under a reduced pressure. To thus-obtained solution was added 2000 ml of ethyl acetate, and a water layer was separated. An organic layer was washed twice with ultrapure water. To this contents was added 600 g of propylene glycol monomethyl ether acetate (PGMEA), and the contents were heated up to a liquid temperature of 40 degrees C. under a reduced pressure to remove ethyl acetate and to give a PGMEA solution of a polymer. To this mixture was added dropwise After that, the solution was stirred for 2 hours at 40 degrees C the reaction was quenched by adding 35 g of acetic acid, and ethanol was removed under a reduced pressure To thus-obtained solution a water layer was separated An organic layer was washed twice with ultrapure water To this contents was added 600 g of propylene glycol monomethyl ether acetate (PGMEA) under a reduced pressure to remove ethyl acetate

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 3000 ml glass flask, 1400 g of ethanol, 700 g of pure water, and 50 g of 25% tetraethylammonium hydroxide were placed, and stirred. To this mixture was added dropwise a mixture of 79 g of 2-(3,4-epoxycyclohexyl) ethyl trimethoxy silane, 70 g of tetraethoxy silane, and 14 g of phenyl trimethoxy silane at a liquid temperature of 40 degrees C. After that, the solution was stirred for 2 hours at 40 degrees C. After the reaction finished, the reaction was quenched by adding 35 g of acetic acid, and ethanol was removed under a reduced pressure. To thus-obtained solution was added 2000 ml of ethyl acetate, and a water layer was separated. An organic layer was washed twice with ultrapure water. To this contents was added 600 g of propylene glycol monomethyl ether acetate (PGMEA), and the contents were heated up to a liquid temperature of 40 degrees C. under a reduced pressure to remove ethyl acetate and to give a PGMEA solution of a polymer. To this mixture was added dropwise After that, the solution was stirred for 2 hours at 40 degrees C the reaction was quenched by adding 35 g of acetic acid, and ethanol was removed under a reduced pressure To thus-obtained solution a water layer was separated An organic layer was washed twice with ultrapure water To this contents was added 600 g of propylene glycol monomethyl ether acetate (PGMEA) under a reduced pressure to remove ethyl acetate

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 3000 ml glass flask, 1400 g of ethanol, 700 g of pure water, and 50 g of 25% tetraethylammonium hydroxide were placed, and stirred. To this mixture was added dropwise a mixture of 139 g of 2-(3,4-epoxycyclohexyl) ethyl trimethoxy silane and 32 g of phenyl trimethoxy silane at a liquid temperature of 40 degrees C. After that, the solution was stirred for 2 hours at 40 degrees C. After the reaction finished, the reaction was quenched by adding 35 g of acetic acid, and ethanol was removed under a reduced pressure. To thus-obtained solution was added 2000 ml of ethyl acetate, and a water layer was separated. An organic layer was washed twice with ultrapure water. To this contents was added 600 g of propylene glycol monomethyl ether acetate (PGMEA), and the contents were heated up to a liquid temperature of 40 degrees C. under a reduced pressure to remove ethyl acetate and to give a PGMEA solution of a polymer. To this mixture was added dropwise After that, the solution was stirred for 2 hours at 40 degrees C the reaction was quenched by adding 35 g of acetic acid, and ethanol was removed under a reduced pressure To thus-obtained solution a water layer was separated An organic layer was washed twice with ultrapure water To this contents was added 600 g of propylene glycol monomethyl ether acetate (PGMEA) under a reduced pressure to remove ethyl acetate

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 3000 ml glass flask, 1400 g of ethanol, 700 g of pure water, and 50 g of 25% tetraethylammonium hydroxide were placed, and stirred. To this mixture was added dropwise a mixture of 139 g of 2-(3,4-epoxycyclohexyl) ethyl trimethoxy silane and 32 g of phenyl trimethoxy silane at a liquid temperature of 40 degrees C. After that, the solution was stirred for 2 hours at 40 degrees C. After the reaction finished, the reaction was quenched by adding 35 g of acetic acid, and ethanol was removed under a reduced pressure. To thus-obtained solution was added 2000 ml of ethyl acetate, and a water layer was separated. An organic layer was washed twice with ultrapure water. To this contents was added 600 g of propylene glycol monomethyl ether acetate (PGMEA), and the contents were heated up to a liquid temperature of 40 degrees C. under a reduced pressure to remove ethyl acetate and to give a PGMEA solution of a polymer. To this mixture was added dropwise After that, the solution was stirred for 2 hours at 40 degrees C the reaction was quenched by adding 35 g of acetic acid, and ethanol was removed under a reduced pressure To thus-obtained solution a water layer was separated An organic layer was washed twice with ultrapure water To this contents was added 600 g of propylene glycol monomethyl ether acetate (PGMEA) under a reduced pressure to remove ethyl acetate

Conditions: temp:81.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To the solvents of 60 g ethanol and 30 g PGMEA, 33.33 g TEOS, 5.71 g VTEOS and 2.40 g PTEOS monomers were individually added. While stirring a mixture of 1.13 g 0.1N nitric acid and 18.92 g water was poured, the reaction mixture was heated to reflux at 81° C. for 4 hours before cooling down. 8.84 g butanol was added to the reaction mixture and stirred at room temperature overnight. The resulting polymer was measured to have a molecular weight of Mn=1121 amu, Mw=1723 amu analyzed using the same GPC system as mentioned above. was poured the reaction mixture was heated before cooling down stirred at room temperature overnight

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 1.0 g of a commercially available phenol novolac resin (manufactured by Gunei Chemical Industry Co., Ltd.), 0.2 g of an epoxy-based cross-linking agent (manufactured by Tohto Kasei Co., Ltd., trade name: YH434L) and 0.003 g of a surfactant (manufactured by DIC Corporation, product name: MEGAFAC [registered trademark] R-30, composed of a fluorine-based surfactant) were added. The resultant mixture was dissolved in 6.7 g of propylene glycol monomethyl ether and 15.6 g of propylene glycol monomethyl ether acetate to obtain a solution. Subsequently, the solution was filtered using a polyethylene microfilter with a pore diameter of 0.2 μm to prepare a solution of the organic underlayer film forming composition for use in a lithography process with a multilayer film. were added

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 2 g of the resin obtained in Synthesis Example 2, 0.01 g of a surfactant (manufactured by DIC Corporation, product name: MEGAFAC [trade name] R-30, composed of a fluorine-based surfactant) was added. The resultant mixture was dissolved in 3.5 g of propylene glycol monomethyl ether acetate, 18.4 g of cyclohexanone, and 1.2 g of γ-butyrolactone to obtain a solution. Subsequently, the solution was filtered using a polyethylene microfilter with a pore diameter of 0.2 μm to prepare a solution of the organic underlayer film forming composition for use in a lithography process with a multilayer film. was added