Acrylic compounds for sub-200 nm photoresist compositions and methods for making and using same

A method for preparing an acrylic compound of the formula (I):

• 10
• wherein R1, R2, and R3 are each independently a hydrogen atom, a fluorine atom, an alkyl group, or a fluorinated alkyl group;
• R4 is a hydroxyl group, an alkoxy group, a fluorinated alkoxy group, an acyloxy group, or a fluorine atom;
• R5, R6, R7, and R8 are each independently a fluorine atom, a fluorinated alkyl group having from 1 to 10 carbon atoms, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, or an alkyl-substituted aryl group and at least one of R5, R6, R7, and R8 is a fluorinated alkyl group having from 1 to 10 carbon atoms;
• and wherein the alkyl group comprises from 1 to 20 carbons and the alkenyl and alkynyl groups comprise from 2 to 8 carbons, the method comprising:
• combining a quantity of trifluoroacetone with a base under conditions sufficient to effect a reaction and form a cyclic trimer intermediate product;
• and
• reacting the cyclic trimer intermediate product with an acylating agent under conditions sufficient to form the acrylic compound.

A polymer comprising polymerized units of the acrylic compound having the formula (I):

• 11
• wherein R1, R2, and R3 are each independently a hydrogen atom, a fluorine atom, an alkyl group, or a fluorinated alkyl group;
• R4 is a hydroxyl group, an alkoxy group, a fluorinated alkoxy group, an acyloxy group, or a fluorine atom;
• R5, R6, R7, and R8 are each independently a fluorine atom, a fluorinated alkyl group having from 1 to 10 carbon atoms, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, or an alkyl-substituted aryl group and at least one of R5, R6, R7, and R8 is a fluorinated alkyl group having from 1 to 10 carbon atoms;
• and
• wherein the alkyl group comprises from 1 to 20 carbons and the alkenyl and alkynyl groups comprise from 2 to 8 carbons.

A sub-200 nm photoresist composition comprising:

• a polymer comprising one or more polymerized units of an acrylic compound of the formula (I):
• 12
• wherein R1, R2, and R3 are each independently a hydrogen atom, a fluorine atom, an alkyl group, or a fluorinated alkyl group;
• R4 is a hydroxyl group, an alkoxy group, a fluorinated alkoxy group, an acyloxy group, or a fluorine atom;
• R5, R6, R7, and R8 are each independently a fluorine atom, a fluorinated alkyl group having from 1 to 10 carbon atoms, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, or an alkyl-substituted aryl group and at least one of R5, R6, R7, and R8 is a fluorinated alkyl group having from 1 to 10 carbon atoms;
• and wherein the alkyl group comprises from 1 to 20 carbons and the alkenyl and alkynyl groups comprise from 2 to 8 carbons;
• and
• a photoactive component.

A polymer comprising repeating units of the following formula (II):

• 13
• wherein R1, R2, and R3 are each independently a hydrogen atom, a fluorine atom, an alkyl group, or a fluorinated alkyl group;
• R4 is a hydroxyl group, an alkoxy group, a fluorinated alkoxy group, an acyloxy group, or a fluorine atom;
• R5, R6, R7, and R8 are each independently a fluorine atom, a fluorinated alkyl group having from 1 to 10 carbon atoms, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, or an alkyl-substituted aryl group and at least one of R5, R6, R7, and R8 is a fluorinated alkyl group having from 1 to 10 carbon atoms;
• wherein the alkyl group comprises from 1 to 20 carbons and the alkenyl and alkynyl groups comprise from 2 to 8 carbons;
• and
• wherein n is a number ranging from 3 to 300.