Adamantane-polyphenol oligomer and its photoresist composition and application
A technology of oligomer and adamantane, which is applied in the field of adamantane-polyphenol oligomer and its photoresist composition, can solve the problems such as complex synthesis method, achieve simple synthesis process, improve etching resistance performance, and use raw materials simple effect
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Embodiment 1
[0069] Preparation of adamantane-hydroquinone oligomers, the synthetic route is as follows:
[0070]
[0071] n=an integer from 4 to 20, E 1 for H or Indicates the connection key
[0072] Specific steps: Add 1,3-adamantanediol (16.8g, 100mmol, 1.0eq), hydroquinone (11.0g, 100mmol, 1.0eq.) and 180mL CF in a 250ml Schlenk reaction flask 3 COOH. The temperature of the reaction system was raised to 85°C and heated to reflux. A large amount of white solids appeared during the reaction, and the reaction time was 12 hours. After the reaction was completed, it was directly filtered to obtain a white solid. The solid was dissolved in 200 mL of ethyl acetate, washed with water until neutral, washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was rotary evaporated under reduced pressure to obtain 23 g of a white solid with a yield of 89%. 1 H NMR (400MHz, (CD 3 ) 2SO) δ8.27~8.48 (m, phenolic hydroxyl group), 6.53 (m, benzene ring) 1....
Embodiment 2
[0074] Prepare the adamantane-hydroquinone oligomer protected by Boc anhydride, the synthetic route is as follows:
[0075]
[0076] In the formula, Boc represents E. 1 for H or Indicates the connection key, n=4~20 integers.
[0077] Specific steps are as follows:
[0078] Add adamantane-hydroquinone oligomer (23.0g, chain number: 94.2mmol, 1.0eq), Boc anhydride (di-tert-butyl dicarbonate) (79.1g, 282.6mmol, 3.0eq) into a 100mL three-necked flask .) and 120ml of dry tetrahydrofuran, stirring and dissolving under a nitrogen atmosphere, adding a catalytic amount of 4-N,N-dimethylaminopyridine (DMAP) (550mg, 4.5mmol, 0.05eq) to the solution to initiate the reaction, stirring at room temperature 24h. The reaction solution was extracted with ethyl acetate / water, the organic phase was washed three times with saturated aqueous sodium bisulfate solution and water respectively, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obt...
Embodiment 3
[0080] Preparation of adamantane-catechol oligomers, the synthetic route is as follows:
[0081]
[0082] n=an integer from 4 to 20, E 1 for H or Indicates the connection key
[0083] The specific steps are the same as in Example 1, except that hydroquinone is replaced with catechol, and the reaction yield is 82%. 1 HNMR (400MHz, (CD 3 ) 2 SO) δ8.57~8.32 (m, phenolic hydroxyl group), 6.61~6.75 (m, benzene ring) 1.57~2.33 (m, adamantane). MS (MALDI-TOF): test value m / z=1079.3 (M + , n=4,E 1 = H, the end is ), calculated value: C 70 h 78 o 10 m / z=1078.56 ([M] + ); test value m / z=1471.4 (M + , n=6,E 1 = H, E 2 =OH), calculated value: C 96 h 110 o 13 m / z= 1470.79([M] + ); test value m / z=1955.7 (M + , n=8,E 1 = H, E 2 =OH) Calculated value: C 128 h 146 o 17 m / z=1955.06 ([M] + ).
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