Alternating copolymer, method of producing alternating copolymer, method of producing polymeric compound, and method of forming resist pattern

A method of producing an alternating copolymer, comprising:

• copolymerizing a compound represented by general formula (m0-1) shown below with a compound represented by general formula (m0-2) shown below by living radical polymerization to obtain an alternating copolymer represented by general formula (p0) shown below:
• wherein Rp01 represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms;
• Vp01 represents a single bond or a divalent linking group;
• Rp02 and Rp03 each independently represents a hydrocarbon group which may have a substituent;
• Rp02 and Rp03 may be mutually bonded to form a ring;
• Rp04 represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a halogenated alkyl group having 1 to 5 carbon atoms;
• Rp05 represents an alkyl group, an alkoxy group, a halogen atom, a halogenated alkyl group, a cyano group or a hydroxy group;
• Rp06 represents a linear or branched aliphatic hydrocarbon group;
• and m represents an integer of 0 to 4.

A method of producing a polymeric compound, comprising:

• copolymerizing a compound represented by general formula (m0-1) shown below with a compound represented by general formula (m0-2) shown below by living radical polymerization to obtain an alternating copolymer represented by general formula (p0) shown below;
• subjecting the alternating copolymer to hydrolysis to obtain a first polymeric compound precursor represented by general formula (Pre-1a) shown below;
• reacting the first polymeric compound precursor with a compound represented by general formula (Add-1) shown below to obtain a second polymeric compound precursor represented by general formula (Pre-1b-1) shown below;
• and
• subjecting the second polymeric compound precursor to hydrolysis to obtain a polymeric compound represented by general formula (p1) shown below:
• wherein Rp01 represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms;
• Vp01 represents a single bond or a divalent linking group;
• Rp02 and Rp03 each independently represents a hydrocarbon group which may have a substituent;
• Rp02 and Rp03 may be mutually bonded to form a ring;
• Rp04 represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a halogenated alkyl group having 1 to 5 carbon atoms;
• Rp05 represents an alkyl group, an alkoxy group, a halogen atom, a halogenated alkyl group, a cyano group or a hydroxy group;
• Rp06 represents a linear or branched aliphatic hydrocarbon group;
• and m represents an integer of 0 to 4;
• wherein Rp01 represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms;
• Vp01 represents a single bond or a divalent linking group;
• Rp04 represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a halogenated alkyl group having 1 to 5 carbon atoms;
• Rp05 represents an alkyl group, an alkoxy group, a halogen atom, a halogenated alkyl group, a cyano group or a hydroxy group;
• Rp06 represents a linear or branched aliphatic hydrocarbon group;
• n1 represents an integer of 0 to 4;
• Ra001, Ra002 and Ra003 each independently represents a hydrocarbon group which may have a substituent;
• Ra002 and Ra003 may be mutually bonded to form a ring;
• wherein Rp01 and Rp04 each independently represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms;
• Vp01 represents a single bond or a divalent linking group;
• Ra001, Ra002 and Ra003 each independently represents a hydrocarbon group which may have a substituent;
• Ra002 and Ra003 may be mutually bonded to form a ring;
• Rp05 represents an alkyl group, an alkoxy group, a halogen atom, a halogenated alkyl group, a cyano group or a hydroxy group;
• and n1 represents an integer of 0 to 4.

A method of producing a polymeric compound, comprising:

• copolymerizing a compound represented by general formula (m0-1) shown below with a compound represented by general formula (m0-2) shown below by living radical polymerization to obtain an alternating copolymer represented by general formula (p0) shown below;
• subjecting the alternating copolymer to hydrolysis to obtain a polymeric compound precursor represented by general formula (Pre-2a) shown below;
• and
• reacting the polymeric compound precursor with a compound represented by general formula (Add-1) shown below to obtain a polymeric compound represented by general formula (p1) shown below:
• wherein Rp01 represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms;
• Vp01 represents a single bond or a divalent linking group;
• Rp02 and Rp03 each independently represents a hydrocarbon group which may have a substituent;
• Rp02 and Rp03 may be mutually bonded to form a ring;
• Rp04 represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a halogenated alkyl group having 1 to 5 carbon atoms;
• Rp05 represents an alkyl group, an alkoxy group, a halogen atom, a halogenated alkyl group, a cyano group or a hydroxy group;
• Rp06 represents a linear or branched aliphatic hydrocarbon group;
• and m represents an integer of 0 to 4;
• wherein Rp01 represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms;
• Vp01 represents a single bond or a divalent linking group;
• Rp04 represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a halogenated alkyl group having 1 to 5 carbon atoms;
• Rp05 represents an alkyl group, an alkoxy group, a halogen atom, a halogenated alkyl group, a cyano group or a hydroxy group;
• n1 represents an integer of 0 to 4;
• Ra001, Ra002 and Ra003 each independently represents a hydrocarbon group which may have a substituent;
• Ra002 and Ra003 may be mutually bonded to form a ring.

A method of producing a polymeric compound, comprising:

• copolymerizing a compound represented by general formula (m0-1) shown below with a compound represented by general formula (m0-2) shown below by living radical polymerization to obtain an alternating copolymer represented by general formula (p0) shown below;
• subjecting the alternating copolymer to hydrolysis to obtain a first polymeric compound precursor represented by general formula (Pre-1a) shown below;
• reacting the first polymeric compound with a compound represented by general formula (Add-2) shown below to obtain a second polymeric compound precursor represented by general formula (Pre-1b-2) shown below;
• and
• subjecting the second polymeric compound precursor to hydrolysis to obtain a polymeric compound represented by general formula (p2) shown below:
• wherein Rp01 represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms;
• Vp01 represents a single bond or a divalent linking group;
• Rp02 and Rp03 each independently represents a hydrocarbon group which may have a substituent;
• Rp02 and Rp03 may be mutually bonded to form a ring;
• Rp04 represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a halogenated alkyl group having 1 to 5 carbon atoms;
• Rp05 represents an alkyl group, an alkoxy group, a halogen atom, a halogenated alkyl group, a cyano group or a hydroxy group;
• Rp06 represents a linear or branched aliphatic hydrocarbon group;
• and m represents an integer of 0 to 4;
• wherein Rp01 represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms;
• Vp01 represents a single bond or a divalent linking group;
• Rp04 represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a halogenated alkyl group having 1 to 5 carbon atoms;
• Rp05 represents an alkyl group, an alkoxy group, a halogen atom, a halogenated alkyl group, a cyano group or a hydroxy group;
• Rp06 represents a linear or branched aliphatic hydrocarbon group;
• n1 represents an integer of 0 to 4;
• Ra004 and Ra005 each independently represents a hydrogen atom or an alkyl group;
• Ra006 represents a hydrocarbon group, provided that Ra006 may be bonded to Ra004 or Ra005 to form a ring;
• and X represents a halogen atom;
• wherein Rp01 and Rp04 each independently represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms;
• Vp01 represents a single bond or a divalent linking group;
• Ra004 and Ra005 each independently represents a hydrogen atom or an alkyl group;
• Ra006 represents a hydrocarbon group, provided that Ra006 may be bonded to Ra004 or Ra005 to form a ring;
• Rp05 represents an alkyl group, an alkoxy group, a halogen atom, a halogenated alkyl group, a cyano group or a hydroxy group;
• and m represents an integer of 0 to 4.

A method of producing a polymeric compound, comprising:

• copolymerizing a compound represented by general formula (m0-1) shown below with a compound represented by general formula (m0-2) shown below by living radical polymerization to obtain an alternating copolymer represented by general formula (p0) shown below;
• subjecting the alternating copolymer to hydrolysis to obtain a polymeric compound precursor represented by general formula (Pre-2a) shown below;
• and
• reacting the polymeric compound precursor with a compound represented by general formula (Add-2) shown below to obtain a polymeric compound represented by general formula (p2) shown below:
• wherein Rp01 represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms;
• Vp01 represents a single bond or a divalent linking group;
• Rp02 and Rp03 each independently represents a hydrocarbon group which may have a substituent;
• Rp02 and Rp03 may be mutually bonded to form a ring;
• Rp04 represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a halogenated alkyl group having 1 to 5 carbon atoms;
• Rp05 represents an alkyl group, an alkoxy group, a halogen atom, a halogenated alkyl group, a cyano group or a hydroxy group;
• Rp06 represents a linear or branched aliphatic hydrocarbon group;
• and m represents an integer of 0 to 4;
• wherein Rp01 represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms;
• Vp01 represents a single bond or a divalent linking group;
• Rp04 represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a halogenated alkyl group having 1 to 5 carbon atoms;
• Rp05 represents an alkyl group, an alkoxy group, a halogen atom, a halogenated alkyl group, a cyano group or a hydroxy group;
• n1 represents an integer of 0 to 4;
• Ra004 and Ra005 each independently represents a hydrogen atom or an alkyl group;
• Ra006 represents a hydrocarbon group, provided that Ra006 may be bonded to Ra004 or Ra005 to form a ring;
• and X represents a halogen atom.