Tertiary amine compounds having an ester structure and processes for preparing same
The present invention provides ester group-containing tertiary amine compounds of the formula (R 1 OCH 2 CH 2 ) n N(CH 2 CH 2 CO 2 R 2 ) 3-n which, when used as additives in chemical amplification photolithography, can yield photoresists having a high resolution and an excellent focus margin. The present invention also provides a process comprising the step of subjecting a primary or secondary amine compound to Michael addition to an acrylic ester compound; a process comprising the steps of subjecting monoethanolamine or diethanolamine to Michael addition to an acrylic ester compound so as to form an ester group-containing amine compound and introducing a R 1 group to the resultant ester group-containing amine compound; and a process comprising the step of effecting the ester exchange reaction of an ester group-containing tertiary amine with R 2 OH.
1. An ester group-containing tertiary amine compound represented by the following general formula (1)
(R 1 OCH 2 CH 2 ) n N(CH 2 CH 2 CO 2 R 2 ) 3-n (1)
wherein n is 1 or 2; and R 1 independently represents a straight-chain, branched or cyclic saturated alkyl group of 1 to 20 carbon atoms which may contain an ether, or carbonyloxy group; and R 2 independently represents a straight-chain, branched or cyclic saturated alkyl group of 1 to 20 carbon atoms which may contain an ether, carbonyl or carbonyloxy group.
2. An ester group-containing tertiary amine compound as claimed in claim 1 wherein, in the above general formula (1), R 1 has 1 to 10 carbon atoms and R 2 has 2 to 10 carbon atoms.
3. An ester group-containing tertiary amine compound as claimed in claim 1 wherein, in the above general formula (1), R 2 has 2 to 10 carbon atoms.
4. An ester group-containing tertiary amine compound as claimed in claim 1 wherein, in the above general formula (1), R 1 is a methyl group and R 2 has 2 to 10 carbon atoms.
5. An ester group-containing tertiary amine compound as claimed in claim 2 wherein, in the above general formula (1), R 1 is a methyl group and R 2 has 2 to 10 carbon atoms.
6. An ester group-containing tertiary amine compound represented by the following general formula (1)
(R 1 OCH 2 CH 2 ) n N(CH 2 CH 2 CO 2 R 2 ) 3-n (1)
wherein n is 1; and R 1 and R 2 each independently represents a straight-chain, branched or cyclic saturated alkyl group of 1 to 20 carbon atoms which may contain an ether, carbonyl or carbonyloxy group; and selected from the group consisting of:
7. An ester group-containing tertiary amine compound represented by the following general formula (1)
(R 1 OCH 2 CH 2 ) n N(CH 2 CH 2 CO 2 R 2 ) 3-n (1)
wherein n is 2; and R 1 and R 2 each independently represents a straight-chain, branched or cyclic saturated alkyl group of 1 to 20 carbon atoms which may contain an ether, carbonyl or carbonyloxy group; and selected from the group consisting of:
8. An ester group-containing tertiary amine compound selected from the group consisting of: