Calixresorcinarene compounds, photoresist base materials, and compositions thereof
A photoresist, resorcinol cup technology, applied in the preparation of organic compounds, optics, organic chemistry, etc., can solve the problems of reduced sensitivity of photoresist and inability to carry out reaction, etc.
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Embodiment 1
[0155] [Photoresist substrate]
[0156] (1) Synthesis of calix-[4]-resorcinol arene
[0157] Under nitrogen flow, in the three-neck flask (capacity 500 milliliters) that is fully dried and replaced with nitrogen, is provided with dropping funnel, Dimroth condenser, thermometer, encloses resorcinol (33g, 300 mmol) and acetaldehyde ( 17 ml, 300 mmol), and distilled methanol (300 ml) was added under nitrogen pressure to prepare a methanol solution. This methanol solution was heated to 75°C with stirring in an oil bath. Next, 75 ml of concentrated hydrochloric acid was slowly dropped into the mixture using a dropping funnel, followed by heating and stirring at 75° C. for 2 hours. After the reaction was completed, it was left to cool to room temperature, and then cooled with an ice bath. After standing still for 1 hour, white crude crystals of the target compound were formed, which were filtered off. This crude crystal was washed twice with pure water (100 milliliters), then re...
manufacture example 1
[0161] [Photoresist substrate]
[0162] (1) Synthesis of calix-[4]-resorcinol arenes
[0163] Under nitrogen flow, in the three-neck flask (capacity 500 milliliters) that is fully dried and replaced with nitrogen, is provided with dropping funnel, Dimroth condenser, thermometer, encloses resorcinol (33g, 300 mmol) and acetaldehyde ( 17 ml, 300 mmol), and distilled methanol (300 ml) was added under nitrogen pressure to prepare a methanol solution. This methanol solution was heated to 75°C with stirring in an oil bath. Next, 75 ml of concentrated hydrochloric acid was slowly dropped into the mixture using a dropping funnel, followed by heating and stirring at 75° C. for 2 hours. After the reaction was completed, it was left to cool to room temperature, and then cooled with an ice bath. After standing still for 1 hour, white crude crystals of the target compound were formed, which were filtered off. This crude crystal was washed twice with pure water (100 milliliters), then r...
Embodiment 2
[0169] [Photoresist composition]
[0170] As the substrate, 87 parts by weight of the resorcinolcalixarene compound from which basic impurities were removed by washing with an acidic aqueous solution and treating with an ion exchange resin in Production Example 1 (3) was used, and triphenylsulfonium trifluoride was used as the PAG. 10 parts by weight of methanesulfonate, 3 parts by weight of 1,4-diazabicyclo[2.2.2]octane as a quencher, and dissolve the solid composed of these components at a ratio that can finally make it 20% by weight In 2-methoxyethanol, a photoresist solution (photoresist composition) was thus prepared. This photoresist solution was spin-coated (4000 rpm, 60 seconds) on a silicon wafer, and heated at 90° C. for 180 seconds to form a thin film with a thickness of 200 nm. Next, using an electron beam exposure device (JBX-5DR manufactured by JEOL Ltd.), 20 μC / cm 2 Electron beams used to draw line and space patterns with line widths and line spaces of 50nm, 8...
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