Photoresist composition, coated substrate including the photoresist composition, and method of forming electronic device
A technology of photoresist and composition, applied in the original parts for photomechanical processing, photosensitive materials for photomechanical equipment, optics, etc., can solve unsolved problems such as structural characteristics and physical properties of PAG
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example 1
[0151] Example 1: The photoacid generator PAG 1 was prepared according to the synthetic scheme outlined in Synthetic Scheme 1.
[0152] Synthesis process 1
[0153]
[0154] A solution of malononitrile (10.00 grams (g), 151 millimoles (mmol)), 1-(trimethoxymethyl)adamantane (18.19 g, 76 mmol) and pyridine (5.99 g, 76 mmol) was heated at reflux for 20 minutes (min). The reaction mixture was allowed to cool to room temperature. The reaction mixture was charged with dichloromethane (200 milliliters (mL)), triphenylsulfonium bromide (23.38 g, 68 mmol), and deionized water (100 mL) with stirring. The mixture was stirred at room temperature for 16 hours. The organic phase was separated and washed with three 100 mL volumes of deionized water. The solvent was removed under vacuum to yield triphenylsulfonium 2-adamantyl-1,1,3,3-tetracyanoacrylate (PAG 1) (36.70 g, 100% yield).
example 2
[0155] Example 2: The photoacid generator PAG-2 was prepared according to the synthetic scheme outlined in Synthetic Scheme 2.
[0156] Synthesis process 2
[0157]
[0158] The synthesis of the starting material 2-methoxy-1,1,3,3-tetracyanopropenide is described in J.Am.Chem.Soc. 1958, 80 , 2795 in. Sodium 2-methoxy-1,1,3,3-tetracyanopropenide (10.00 g, 51.5 mmol) was dissolved in methanol (100 mL) and adamantylmethylamine (8.51 g, 51.5 mmol) was added to it. The reaction mixture was heated at reflux for two hours and cooled to ambient temperature. Solvent was removed under vacuum. To the residual solid triphenylsulfonium bromide (15.91 g, 46.4 mmol) was added dichloromethane (150 mL) and deionized water (75 mL). The mixture was stirred for 16 hours. The organic phase was separated and washed with three 75 mL volumes of deionized water. The solvent was removed under vacuum to afford triphenylsulfonium 2-adamantylmethylamino-1,1,3,3-tetracyanoacrylate (PAG 2) (26.34 ...
example 3
[0159] Example 3: The photoacid generator PAG 3 was prepared by the synthetic scheme outlined in Scheme 3.
[0160] Synthesis process 3
[0161]
[0162] According to literature procedure ("Journal of Organic Chemistry (J.Org.Chem.)", 2013, 78 (3), 1014) prepare the starting material 1,3-bis(dicyanomethylene)-2,3-dihydro-1H-indene-2-ammonium and mix it with an equimolar amount of tribromide The phenylsulfonium was mixed in a water / dichloromethane 1 / 1 volume mixture. The mixture was stirred for 16 hours. The organic phase was separated and washed three times with deionized water. The solvent was removed under vacuum to afford PAG 3.
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