Sulfonium sulfonate photoacid generator synthesized from abietic acid and synthesis method of sulfonium sulfonate photoacid generator
A technology of photoacid generator and synthesis method, which is applied in the field of photoresist, can solve the problems of exposure influence, poor transparency, etc., and achieve the effects of excellent etching resistance, uniform dissolution, and simple synthesis route
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[0037]Example 1:
[0038]
[0039]The first step: 1-1 (10 g, 33.1 mmol), 1,1-difluoro-2-hydroxythhane-1-sulfonate (6.1 g, 33.1 mmol) was added to toluene (100 g), Toluenesulfonic acid (0.8 g, 4.6 mmol) was added, and the reaction liquid was refluxed for 16 hours. After cooling, the reaction liquid was cooled to obtain a solid, and the solid was washed three times with acetonitrile (100 g × 3), and the mixed acetonitrile solution was concentrated, and added to Methyl tert-butyl ether (100 g) is performed, and the above mixed liquid is filtered, and the dry filter cake is collected from the solid compound 1-2 (12.5 g, 26.7 mmol, yield 80.6%);
[0040]Step 2: Under nitrogen stream protection, (cyclohexex-1,5-dienyloxy) -timethyl-silane (4.5 g, 26.7 mmol) and tetramel sulfoxide (2.8 g, 26.9) Mmol) The solution was cooled to -30 degrees Celsius in chloroform (250 g), and Trifluoroacetic anhydride (8 g, 38.1 mmol) was slowly added, and the reaction was stirred for 30 minutes, and 1-2 was added to ...
Example Embodiment
[0041]Example 2:
[0042]
[0043]The first step: 2-1 (10 g, 33.1 mmol), 1,1,2,2-tetrafluoro-3-hydroxypropane-1-sulfonate (7.7 g, 32.9 mmol) and sulfuric acid (0.5 g) 5.1 mmol) was added to toluene (150 g), heat reflux for 18 hours and cooled to room temperature. The mixture was filtered to give a solid, and the solid was washed three times with acetonitrile (100 g × 3). The mixed acetonitrile solution was concentrated and added to methyl tert-butyl ether (100 g), and the mixed liquid was filtered, and the dry filter cake was collected, and the intermediate 2-2 (13.5 g, 26.0 mmol, yield) 78.7%).
[0044]Step 2: Under nitrogen stream protection, (cyclohexene-1,5-diene oxyloxy) -timethyl-silane (4.4 g, 26.1 mmol) and tetramel sulfoxide (2.7 g, 25.9) Mmol) dissolved in chloroform (200 g), cooled to -30 degrees Celsius, slowly added trifluoroacetic anhydride (6.5 g, 30.9 mmol), stirred for 30 minutes, add 2-2 under stirring (13.5 g , 26.0 mmol) saturated aqueous solution, stirring reaction for 1...
Example Embodiment
[0045]Example 3:
[0046]
[0047]The first step: Pulsi acid (10 g, 33.1 mmol) was dissolved in anhydrous tetrahydrofuran (100 g), cooled to 0 degrees Celsius with ice water bath, slowly added hydride (2.5 g, 65.9 mmol) under nitrogen gas stream protection. The reaction liquid was heated and refluxed for 12 hours. The reaction liquid cooled to 0.5 g of water, adding 15% sodium hydroxide solution (6 g), adding 7.5 g of water, stirring to room temperature for half an hour, adding tetrahydrofuran 50g dilution Filtering with celite is filtered, the filter cake was washed with tetrahydrofuran (50 g), and the filtrate was dried over anhydrous sodium sulfate, and the intermediate 3-2 (9.1 g, 31.5 mmol, yield: 95.4%) was concentrated under vacuum. ).
[0048]Step 2: 3-2 (9.1 g, 31.5 mmol), sodium carboxyvylfluoromethanesulfonate (6.2 g, 31.3 mmol) is added to toluene (100 g), adding methabenzulfonic acid (0.8 g) 4.6 mmol), the reaction liquid was heated and refluxed for 16 hours. After cooling of th...
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