Photoresist composition, resist-pattern forming method, polymer, and compound
A photoresist composition includes a polymer that includes a structural unit shown by the following formula (1), and a photoacid generator. R 1 in the formula (1) represents a hydrogen atom, a fluorine atom, a methyl group, or a trifluoromethyl group, Z represents a group that forms a divalent alicyclic group having 3 to 20 carbon atoms together with a carbon atom bonded to X, X represents an alkanediyl group having 1 to 6 carbon atoms, Y represents a hydrogen atom or —CR 2 R 3 (OR 4 ), and R 2 to R 4 independently represent a hydrogen atom or a monovalent hydrocarbon group, provided that R 3 and R 4 optionally bond to each other to form a cyclic ether structure together with a carbon atom bonded to R 3 and an oxygen atom bonded to R 4 .
1. A resist pattern-forming method comprising:
applying a photoresist composition to a substrate to form a resist film;
exposing the resist film by applying radiation to the resist film via a photomask;
heating the exposed resist film;
developing the heated resist film; and
rinsing and drying the developed resist film to form a resist pattern made from the photoresist composition,
wherein the photoresist composition comprises:
a polymer that includes a structural unit shown by a formula (1); and
a photoacid generator,
wherein R 1 represents a hydrogen atom, a fluorine atom, a methyl group, or a trifluoromethyl group, Z represents a group that forms a divalent monoalicyclic group having 5 to 8 carbon atoms together with a carbon atom bonded to X, X represents an alkanediyl group having 1 to 6 carbon atoms, Y represents a hydrogen atom or —CR 2 R 3 (OR 4 ), and R 2 to R 4 independently represent a hydrogen atom or a monovalent hydrocarbon group, provided that R 3 and R 4 optionally bond to each other to form a cyclic ether structure together with a carbon atom bonded to R 3 and an oxygen atom bonded to R 4 .
2. The resist pattern-forming method according to claim 1 , wherein X represents an alkanediyl group having 2 to 4 carbon atoms.
3. The resist pattern-forming method according to claim 1 , wherein Y represents —CR 2 R 3 (OR 4 ).
4. The resist pattern-forming method according to claim 1 , wherein the polymer further includes a structural unit shown by a formula (2),
wherein R 5 represents a hydrogen atom, a fluorine atom, a methyl group, or a trifluoromethyl group, R p1 represents a chain-like hydrocarbon group having 1 to 10 carbon atoms or an alicyclic group having 3 to 20 carbon atoms, and R p2 and R p3 independently represent a chain-like hydrocarbon group having 1 to 10 carbon atoms or an alicyclic group having 4 to 20 carbon atoms, provided that R p2 and R p3 optionally bond to each other to form a divalent alicyclic group having 4 to 20 carbon atoms together with a carbon atom bonded to R p2 and R p3 .
5. The resist pattern-forming method according to claim 1 , wherein the photoresist composition further comprises either or both of a compound shown by a formula (3-1) and a compound shown by a formula (3-2),
wherein R 6 to R 10 independently represent a hydrogen atom, an alkyl group, an alkoxy group, a hydroxyl group, or a halogen atom, E − and G − independently represent OH 31 , R A —COO − , R A —SO 3 − , or R A —N − —SO 2 —R B , R A represents an alkyl group, a cycloalkyl group, an aryl group, or an aralkyl group, provided that some or all of hydrogen atoms included in R A may be substituted with a substituent, and R B represents an alkyl group or an aralkyl group, provided that some or all of hydrogen atoms included in R B may be substituted with a fluorine atom.
6. A photoresist composition comprising a polymer that includes a structural unit shown by a formula (1), and a photoacid generator,
wherein R 1 represents a hydrogen atom, a fluorine atom, a methyl group, or a trifluoromethyl group, Z represents a group that forms a divalent alicyclic group having 3 to 20 carbon atoms together with a carbon atom bonded to X, X represents an alkanediyl group having 1 to 6 carbon atoms, Y represents —CR 2 R 3 (OR 4 ), and R 2 to R 4 independently represent a hydrogen atom or a monovalent hydrocarbon group, provided that R 3 and R 4 optionally bond to each other to form a cyclic ether structure together with a carbon atom bonded to R 3 and an oxygen atom bonded to R 4 .
7. The photoresist composition according to claim 6 , wherein X represents an alkanediyl group having 2 to 4 carbon atoms.
8. The photoresist composition according to claim 6 , wherein the polymer further includes a structural unit shown by a formula (2),
wherein R 5 represents a hydrogen atom, a fluorine atom, a methyl group, or a trifluoromethyl group, R p1 represents a chain-like hydrocarbon group having 1 to 10 carbon atoms or an alicyclic group having 3 to 20 carbon atoms, and R p2 and R p3 independently represent a chain-like hydrocarbon group having 1 to 10 carbon atoms or an alicyclic group having 4 to 20 carbon atoms, provided that R p2 and R p3 optionally bond to each other to form a divalent alicyclic group having 4 to 20 carbon atoms together with a carbon atom bonded to R p2 and R p3 .
9. The photoresist composition according to claim 6 , further comprising either or both of a compound shown by a formula (3-1) and a compound shown by a formula (3-2),
wherein R 6 to R 10 independently represent a hydrogen atom, an alkyl group, an alkoxy group, a hydroxyl group, or a halogen atom, E − and G − independently represent OH − , R A —COO − , R A —SO 3 − , or R A —N − —SO 2 —R B , R A represents an alkyl group, a cycloalkyl group, an aryl group, or an aralkyl group, provided that some or all of hydrogen atoms included in R A may be substituted with a substituent, and R B represents an alkyl group or an aralkyl group, provided that some or all of hydrogen atoms included in R B may be substituted with a fluorine atom.
10. A resist pattern-forming method comprising applying the photoresist composition according to claim 6 to a substrate to form a resist film, exposing the resist film by applying radiation to the resist film via a photomask, heating the exposed resist film, and developing the heated resist film.
11. A polymer comprising a structural unit shown by a formula (1),
wherein R 1 represents a hydrogen atom, a fluorine atom, a methyl group, or a trifluoromethyl group, Z represents a group that forms a divalent alicyclic group having 3 to 20 carbon atoms together with a carbon atom bonded to X, X represents an alkanediyl group having 1 to 6 carbon atoms, Y represents —CR 2 R 3 (OR 4 ), and R 2 to R 4 independently represent a hydrogen atom or a monovalent hydrocarbon group, provided that R 3 and R 4 optionally bond to each other to form a cyclic ether structure together with a carbon atom bonded to R 3 and an oxygen atom bonded to R 4 .
12. A compound shown by a formula (i),
wherein R 1 represents a hydrogen atom, a fluorine atom, a methyl group, or a trifluoromethyl group, Z represents a group that forms a divalent alicyclic group having 3 to 20 carbon atoms together with a carbon atom bonded to X, X represents an alkanediyl group having 1 to 6 carbon atoms, Y represents —CR 2 R 3 (OR 4 ), and R 2 to R 4 independently represent a hydrogen atom or a monovalent hydrocarbon group, provided that R 3 and R 4 optionally bond to each other to form a cyclic ether structure together with a carbon atom bonded to R 3 and an oxygen atom bonded to R 4 .