Dendritic polyphenyl substituted adamantane derivative monomolecular resin, positive photoresist composition and negative photoresist composition
A positive photoresist and negative photoresist technology, applied in optics, optomechanical equipment, instruments, etc., can solve the problem of large molecular volume, insufficient lithography pattern resolution and edge roughness, molecular weight polydispersity, etc. question
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Embodiment 1
[0057] The synthetic route for preparing 1,3,5,7-tetrakis-(3,5-dibromophenyl)adamantane is as follows:
[0058]
[0059] Concrete steps: Add 5.0g (i.e. 11.0mmol) tetrabromoadamantane and 20mL (i.e. 165mmol) m-dibromobenzene in a 250ml three-neck flask equipped with a condenser tube, connect an inverted funnel to 30% from the upper end of the condenser tube with a conduit NaOH aqueous solution to absorb the HBr produced by the reaction. Under the cold water bath at 5°C, add 1.2g (ie 4.5mmol) of AlBr to the reaction system 3 , continue to stir and react under the cold water bath for 1 hour, then remove the cold water bath, return to room temperature and react for about 3 hours, and finally the reaction system is heated to 60°C in the oil bath for 4 hours, the reaction solution is cooled to room temperature, and poured into 100mL acidic ice Stir in water for 1h. After the ice melted completely, add 100ml of dichloromethane to the mixture for extraction, wash the organic laye...
Embodiment 2
[0061] The preparation of 1,3,5,7-tetra-[3,5-bis(3,4-dimethoxyphenyl)-phenyl]adamantane, the synthetic route is as follows:
[0062]
[0063] Specific steps:
[0064] Under the protection of high-purity nitrogen, in the Schleck reaction flask of 100ml, add the 1,3,5,7-tetra-(3,5-dibromophenyl) adamantane of 1071.0mg (being 1mmol), 36.6mg (being 0.05mmol ) PdCl 2 (dppf), 1.82g (i.e. 10.0mmol) 3,4-dimethoxyphenylboronic acid, 581mg (i.e. 10mmol) of potassium fluoride solid, the system was under a nitrogen atmosphere, and finally 20ml of distilled dioxane was added , the reaction solution was heated to reflux for 6h, cooled to room temperature, and extracted with dichloromethane / water, the organic layers were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure to remove the solvent, and recrystallized in ethyl acetate / n-hexane to obtain a white solid 1.16g , yield 76%. 1 H NMR (400MHz, CDCl 3 )δ(ppm)7.81(s,8H,benzene),7.38(s,4H),7.19-7.08 (m,...
Embodiment 3
[0066] The preparation of 1,3,5,7-tetra-[3,5-bis(3,4-dihydroxyphenyl)-phenyl]adamantane, the synthetic route is as follows:
[0067]
[0068] Specific steps:
[0069] Add 1.53g (i.e. 1.0mmol) of 1,3,5,7-tetra-[3,5-bis(3,4-dimethoxyphenyl)-phenyl]adamantane and Dissolve 50ml of dichloromethane under a nitrogen atmosphere. At a low temperature of -78°C, add 10ml of boron tribromide-containing dichloromethane solution (concentration: 0.4g / ml) dropwise to the reaction solution with a syringe, and the reaction solution is kept at -78°C After reacting for 1 hour, the temperature was gradually raised to room temperature, and the reaction was continued for 6 hours. The reaction was quenched by slowly adding 20 ml of ice water to the reaction system, and a large amount of white solid was precipitated. The reaction system was filtered to obtain a white solid, which was washed with water and dichloromethane respectively to obtain The solid was precipitated three more times with metha...
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