Sulfonium onium salt photoacid generator containing beta-eudesmol structure, and preparation method thereof
A technology of photoacid generator and eucalyptol, which is applied in the field of photoresist, can solve the problems of acid diffusion, achieve low diffusivity, simple synthesis process, and favorable effects for imaging
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Embodiment 1
[0027] A sulfonium salt photoacid generator 1-3, the specific synthesis steps are as follows:
[0028] 1) β-cineole 1-1 (45.0mmol, 10g), p-methoxyphenol (0.8mmol, 0.1g), difluorosulfoacetic acid sodium salt (44.9mmol, 8.9g) and p-toluenesulfonic acid A mixture of monohydrate (5.2 mmol, 1 g) was heated to reflux in toluene (150 g) for 18 hours and cooled to room temperature; the mixture was filtered and the solid was washed three times with acetonitrile; the combined acetonitrile solution was then concentrated and added to methyl Beat in tert-butyl ether, filter and collect the dried filter cake to obtain solid sulfonate compound 1-2 containing β-cineole structure (38.8mmol, 15.6g, yield 86.2%).
[0029] 2) The sulfonate compound 1-2 (37.3mmol, 15g) and triphenylsulfonium bromide (37.3mmol, 12.8g) obtained in step 1) containing β-eucalyptol structure were dissolved in di In a mixed solvent of methyl chloride (100g) and water (100g); the mixture was stirred at 30°C for 24 hours...
Embodiment 2
[0033] A kind of sulfonium salt photoacid generator 2-3, concrete synthetic steps are as follows:
[0034] 1) β-cineole 2-1 (45.0mmol, 10g), p-methoxyphenol (0.8mmol, 0.1g), 2-sulfoacetate sodium salt (45.0mmol, 7.3g), p-toluene A mixture of sulfonic acid monohydrate (5.2 mmol, 1 g) was heated to reflux in toluene (150 g) for 18 hours and cooled to room temperature; the mixture was filtered and the solid was washed three times with acetonitrile; the combined acetonitrile solution was then concentrated and added to Slurry was performed in methyl tert-butyl ether, filtered and dried filter cake was collected to obtain solid sulfonate compound 2-2 (39.0mol, 14.3g, 86.8%) containing β-cineole structure.
[0035] 2) The sulfonate compound 2-2 (38.2mmol, 14g) containing the β-cineole structure obtained in step 1) and tri(4-methylphenyl)sulfonium chloride (38.4mmol, 13.1g) was dissolved in a mixed solvent of dichloromethane (100g) and water (100g); the mixture was stirred at 30°C fo...
Embodiment 3
[0039] A sulfonium salt photoacid generator 3-3, the specific synthesis steps are as follows:
[0040] 1) Under nitrogen protection at 0°C, pyridine (113.8mmol, 9g), bis(trichloromethyl)carbonate (15.2mmol, 4.5g) was added to dichloromethane (200g) and stirred, then slowly added β- Eucalyptol 3-1 (45.0mmol, 30g); the reaction solution was stirred at 25°C for 3 hours; then 1,1-difluoro-2-hydroxyl-ethanesulfonic acid sodium salt (45.1mmol, 8.3g) was added into the reaction solution, stirred for 10 hours; concentrated by rotary evaporation to obtain a mixture, filtered the mixture, washed the solid with acetonitrile three times; then concentrated the mixed acetonitrile solution, added it to methyl tert-butyl ether for beating, filtered The dried filter cake was collected to obtain solid sulfonate compound 3-2 (34.7 mmol, 15 g, yield 77.1%) containing β-eucalyptol structure.
[0041] 2) The sulfonate compound 3-2 (34.7mmol, 15g) and triphenylsulfonium chloride (34.8mmol, 10.4g) o...
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