Sulfonium onium salt photoacid generator containing patchouli alcohol structure, and preparation method thereof
A technology of photoacid generator and patchouli alcohol, which is applied in the field of photoresist to achieve the effect of improving solubility, low diffusivity and improving resolution
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Embodiment 1
[0027] A sulfonium salt photoacid generator 1-3 containing a patchouli alcohol structure, the specific synthesis steps are as follows:
[0028] 1) Add patchouli alcohol 1-1 (0.225mol, 50g), sodium salt of difluorosulfoacetic acid (0.227mol, 45g) and p-toluenesulfonic acid monohydrate (0.026mol, 5g) into toluene (500g) , heated to reflux for 18 hours and cooled to room temperature to obtain a mixture; the mixture was filtered to obtain a solid, and the solid was washed three times with acetonitrile; the mixed acetonitrile solution was concentrated and added to methyl tert-butyl ether for beating, and the above The mixed solution was collected and the filter cake was dried to obtain the sulfonate compound 1-2 (0.162mol, 65g, yield 71.8%) containing patchouli alcohol structure.
[0029] 2) The sulfonate compound 1-2 (0.159mol, 60g) and triphenylsulfonium bromide (0.151mol, 52g) obtained in step 1) containing the patchouli alcohol structure were dissolved in dichloromethane ( 300...
Embodiment 2
[0033] A sulfonium salt photoacid generator 2-3 containing a patchouli alcohol structure, the specific synthesis steps are as follows:
[0034] 1) Patchouli alcohol 2-1 (0.225mol, 50g), 2-sulfoacetate sodium salt (0.228mol, 37g) and p-toluenesulfonic acid monohydrate (0.026mol, 5g) were added to toluene (500g ), heated to reflux for 18 hours and cooled to room temperature; filtered the mixture to obtain a solid, and the solid was washed three times with acetonitrile; the mixed acetonitrile solution was concentrated and added to methyl tert-butyl ether for beating, and the above mixed solution was filtered, The dried filter cake was collected to obtain the sulfonate compound 2-2 (0.172mol, 63g, 76.5%) containing patchouli alcohol structure.
[0035] 2) The sulfonate compound 2-2 (0.163mol, 60g) containing the patchouli alcohol structure obtained in step 1) and three (4-methylphenyl) sulfonium chloride (0.164mol, 56g) Dissolved in a mixed solvent of dichloromethane (400g) and w...
Embodiment 3
[0039] A sulfonium salt-based photoacid generator 3-3 containing a patchouli alcohol structure, the specific synthesis steps are as follows:
[0040] 1) Under nitrogen protection at 0°C, add pyridine (0.569mol, 45g), bis(trichloromethyl)carbonate (0.078mol, 23g) into dichloromethane (2000g) and stir, then slowly add patchouli alcohol 3-1 (0.225mol, 50g); the reaction mixture was stirred at 25°C for 3 hours; then 1,1-difluoro-2-hydroxyl-ethanesulfonic acid sodium salt (0.228mol, 89g) was added to the reaction solution, Stir for 10 hours; concentrate by rotary evaporation to obtain a mixture, filter the mixture to obtain a solid, and wash the solid three times with acetonitrile; concentrate the mixed acetonitrile solution, and add it to methyl tert-butyl ether for beating, filter the above mixture, collect and dry The filter cake was dried to obtain the sulfonate compound 3-2 (0.162mol, 70g, yield 72.0%) containing patchouli alcohol structure.
[0041] 2) The sulfonate compound...
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