Chemically amplified positive-type photosensitive resin composition, photosensitive dry film, production method for photosensitive dry film, production method for patterned resist film, compound, photo-acid generator, and production method for n-organosulfonyloxy compound

A compound represented by the following formula (A1):

• wherein Rb1 is a hydrocarbon group having 1 or more and 30 or less carbon atoms;
• when the hydrocarbon group as Rb1 contains 1 or more methylene groups, at least a part of the methylene groups may be replaced with a group selected from the group consisting of —O—, —S—, —CO—, —OO—O—, —SO—, —SO2—, —CRb4Rb5—, and —NRb6—;
• when the hydrocarbon group as Rb1 contains a hydrocarbon ring, at least one of the carbon atoms constituting the hydrocarbon ring may be replaced with a heteroatom selected from the group consisting of N, O, P, S, and Se or an atomic group containing the heteroatom;
• Rb4 and Rb5 are each independently a hydrogen atom or a halogen atom, and at least one of Rb4 and Rb5 is a halogen atom;
• Rb6 is a hydrogen atom or a hydrocarbon group having 1 or more and 6 or less carbon atoms;
• Ra1 and Ra2 are each independently a hydrogen atom, an optionally substituted aliphatic hydrocarbon group having 1 or more and 20 or less carbon atoms, an optionally substituted aromatic group having 5 or more and 20 or less ring constituting atoms, or a group represented by —Ra3—Ra4;
• Ra1 and Ra2 are not simultaneously hydrogen atoms;
• when the aliphatic hydrocarbon group as Ra1 or Ra2 contains 1 or more methylene groups, at least a part of the methylene groups may be replaced with a group selected from the group consisting of —O—, —S—, —CO—, —CO—O—, —SO—, —SO2—, and —NRa5—;
• Ra5 is a hydrogen atom or a hydrocarbon group having 1 or more and 6 or less carbon atoms;
• Ra3 is a methylene group, —O—, —CO—, —CO—O—, —SO—, —SO2—, or —NRa6—;
• Ra6 is a hydrogen atom or a hydrocarbon group having 1 or more and 6 or less carbon atoms;
• Ra4 is an optionally substituted aromatic group having 5 or more and 20 or less ring constituting atoms, a perfluoroalkyl group having 1 or more and 6 or less carbon atoms, an optionally substituted aralkyl group having 7 or more and 20 or less carbon atoms, or a heteroarylalkyl group having an optionally substituted aromatic heterocyclic group having 5 or more and 20 or less ring constituting atoms;
• Q1 and Q2 are each independently a fluorine atom or a perfluoroalkyl group having 1 or more and 6 or less carbon atoms;
• and
• L is an ester bond.

A method of manufacturing a N-organosulfonyloxy compound,

• the method comprising:
• reacting a N-hydroxy compound (A′) and a sulfonyl fluoride compound (B′) in the presence of a basic compound (D′),
• wherein a silylating agent (C′) is present in the system while the N-hydroxy compound (A′) and the sulfonyl fluoride compound (B′) are reacted,
• the sulfonyl fluoride compound (B′) is represented by the following formula (bi1):
• Rbi1—SO2—F (bi1)
• wherein Rbi1 is an organic group, and
• the silylating agent (C′) is capable of converting a hydroxy group on the nitrogen atom possessed by the N-hydroxy compound (A′) into a silyloxy group represented by the following formula (ac1):
• —O—Si(Rc1)3 (ac1)
• wherein each Rc1 is independently a hydrocarbon group having 1 or more and 10 or less carbon atoms.

A method of manufacturing a N-organosulfonyloxy compound,

• the method comprising:
• silylating a N-hydroxy compound (A′) with a silylating agent (C′), and
• condensing a silylated product of the N-hydroxy compound (A′) generated in the silylation step with a sulfonyl fluoride compound (B′) in the presence of a basic compound (D′),
• wherein the sulfonyl fluoride compound (B′) is represented by the following formula (bi1):
• Rbi1—SO2—F (bi1)
• wherein Rbi1 is an organic group, and
• the silylating agent is capable of converting a hydroxy group on the nitrogen atom possessed by the N-hydroxy compound (A′) into a silyloxy group represented by the following formula (ac1):
• —O—Si(Rc1)3 (ac1)
• wherein each Rc1 is independently a hydrocarbon group having 1 or more and 10 or less carbon atoms.