Alternating copolymer, method of producing alternating copolymer, method of producing polymeric compound, and method of forming resist pattern
An alternating copolymer including a structural unit (a0-1) represented by general formula (a0-1) and a structural unit (a0-2) represented by general formula (a0-2) in which Rp 01 represents a hydrogen atom or the like; Vp 01 represents a single bond or a divalent linking group; Rp 02 and Rp 03 each independently represents a hydrocarbon group which may have a substituent, or Rp 02 and Rp 03 are mutually bonded to form a ring; Rp 04 represents a hydrogen atom, a C1-C5 alkyl group or a C1-C5 halogenated alkyl group; Rp 05 represents an alkyl group, an alkoxy group, a halogen atom, a halogenated alkyl group, a cyano group or a hydroxy group; Rp 06 represents a linear or branched aliphatic hydrocarbon group; and m represents an integer of 0 to 4
1. An alternating copolymer comprising:
a structural unit (a0-1) represented by general formula (a0-1) shown below, and
a structural unit (a0-2) represented by general formula (a0-2) shown below:
wherein Rp 01 represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; Vp 01 represents a single bond or a divalent linking group; Rp 02 and Rp 03 each independently represents a hydrocarbon group which may have a substituent; Rp 02 and Rp 03 may be mutually bonded to form a ring; Rp 04 represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a halogenated alkyl group having 1 to 5 carbon atoms; Rp 05 represents an alkyl group, an alkoxy group, a halogen atom, a halogenated alkyl group, a cyano group or a hydroxy group; Rp 06 represents a linear or branched aliphatic hydrocarbon group; and n 1 represents an integer of 0 to 4.
2. 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 Rp 01 represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; Vp 01 represents a single bond or a divalent linking group; Rp 02 and Rp 03 each independently represents a hydrocarbon group which may have a substituent; Rp 02 and Rp 03 may be mutually bonded to form a ring; Rp 04 represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a halogenated alkyl group having 1 to 5 carbon atoms; Rp 05 represents an alkyl group, an alkoxy group, a halogen atom, a halogenated alkyl group, a cyano group or a hydroxy group; Rp 06 represents a linear or branched aliphatic hydrocarbon group; and n 1 represents an integer of 0 to 4.
3. 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 Rp 01 represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; Vp 01 represents a single bond or a divalent linking group; Rp 02 and Rp 03 each independently represents a hydrocarbon group which may have a substituent; Rp 02 and Rp 03 may be mutually bonded to form a ring; Rp 04 represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a halogenated alkyl group having 1 to 5 carbon atoms; Rp 05 represents an alkyl group, an alkoxy group, a halogen atom, a halogenated alkyl group, a cyano group or a hydroxy group; Rp 06 represents a linear or branched aliphatic hydrocarbon group; and n 1 represents an integer of 0 to 4;
wherein Rp 01 represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; Vp 01 represents a single bond or a divalent linking group; Rp 04 represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a halogenated alkyl group having 1 to 5 carbon atoms; Rp 05 represents an alkyl group, an alkoxy group, a halogen atom, a halogenated alkyl group, a cyano group or a hydroxy group; Rp 06 represents a linear or branched aliphatic hydrocarbon group; n 1 represents an integer of 0 to 4; Ra 001 , Ra 002 and Ra 003 each independently represents a hydrocarbon group which may have a substituent; Ra 002 and Ra 003 may be mutually bonded to form a ring;
wherein Rp 01 and Rp 04 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; Vp 01 represents a single bond or a divalent linking group; Ra 001 , Ra 002 and Ra 003 each independently represents a hydrocarbon group which may have a substituent; Ra 002 and Ra 003 may be mutually bonded to form a ring; Rp 05 represents an alkyl group, an alkoxy group, a halogen atom, a halogenated alkyl group, a cyano group or a hydroxy group; and n 1 represents an integer of 0 to 4.
4. A method of forming a resist pattern, comprising:
obtaining a polymeric compound (A01) represented by general formula (p1) by the method of producing a polymeric compound according to claim 3 ;
mixing the polymeric compound (A01) with an organic solvent to prepare a resist composition;
forming a resist film on a substrate using the resist composition;
exposing the resist film; and
developing the exposed resist film to form a resist pattern.
5. 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 (p 1) shown below:
wherein Rp 01 represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; Vp 01 represents a single bond or a divalent linking group; Rp 02 and Rp 03 each independently represents a hydrocarbon group which may have a substituent; Rp 02 and Rp 03 may be mutually bonded to form a ring; Rp 04 represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a halogenated alkyl group having 1 to 5 carbon atoms; Rp 05 represents an alkyl group, an alkoxy group, a halogen atom, a halogenated alkyl group, a cyano group or a hydroxy group; Rp 06 represents a linear or branched aliphatic hydrocarbon group; and n 1 represents an integer of 0 to 4;
wherein Rp 01 represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; Vp 01 represents a single bond or a divalent linking group; Rp 04 represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a halogenated alkyl group having 1 to 5 carbon atoms; Rp 05 represents an alkyl group, an alkoxy group, a halogen atom, a halogenated alkyl group, a cyano group or a hydroxy group; n 1 represents an integer of 0 to 4; Ra 001 , Ra 002 and Ra 003 each independently represents a hydrocarbon group which may have a substituent; Ra 002 and Ra 003 may be mutually bonded to form a ring.
6. A method of forming a resist pattern, comprising:
obtaining a polymeric compound (A01) represented by general formula (p1) by the method of producing a polymeric compound according to claim 5 ;
mixing the polymeric compound (A01) with an organic solvent to prepare a resist composition;
forming a resist film on a substrate using the resist composition;
exposing the resist film; and
developing the exposed resist film to form a resist pattern.
7. 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 Rp 01 represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; Vp 01 represents a single bond or a divalent linking group; Rp 02 and Rp 03 each independently represents a hydrocarbon group which may have a substituent; Rp 02 and Rp 03 may be mutually bonded to form a ring; Rp 04 represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a halogenated alkyl group having 1 to 5 carbon atoms; Rp 05 represents an alkyl group, an alkoxy group, a halogen atom, a halogenated alkyl group, a cyano group or a hydroxy group; Rp 06 represents a linear or branched aliphatic hydrocarbon group; and n 1 represents an integer of 0 to 4;
wherein Rp 01 represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; Vp 01 represents a single bond or a divalent linking group; Rp 04 represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a halogenated alkyl group having 1 to 5 carbon atoms; Rp 05 represents an alkyl group, an alkoxy group, a halogen atom, a halogenated alkyl group, a cyano group or a hydroxy group; Rp 06 represents a linear or branched aliphatic hydrocarbon group; n 1 represents an integer of 0 to 4; Ra 04 and Ra 05 each independently represents a hydrogen atom or an alkyl group; Ra 006 represents a hydrocarbon group, provided that Ra 006 may be bonded to Ra 004 or Ra 005 to form a ring; and X represents a halogen atom;
wherein Rp 01 and Rp 04 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; Vp 01 represents a single bond or a divalent linking group; Ra 004 and Ra 005 each independently represents a hydrogen atom or an alkyl group; Ram6 represents a hydrocarbon group, provided that Ra 006 may be bonded to Ra 004 or Ra 005 to form a ring; Rp 05 represents an alkyl group, an alkoxy group, a halogen atom, a halogenated alkyl group, a cyano group or a hydroxy group; and n 1 represents an integer of 0 to 4.
8. A method of forming a resist pattern, comprising:
obtaining a polymeric compound (A02) represented by general formula (p2) by the method of producing a polymeric compound according to claim 7 ;
mixing the polymeric compound (A02) with an organic solvent to prepare a resist composition;
forming a resist film on a substrate using the resist composition;
exposing the resist film; and
developing the exposed resist film to form a resist pattern.
9. 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 Rp 01 represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; Vp 01 represents a single bond or a divalent linking group; Rp 02 and Rp 03 each independently represents a hydrocarbon group which may have a substituent; Rp 02 and Rp 03 may be mutually bonded to form a ring; Rp 04 represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a halogenated alkyl group having 1 to 5 carbon atoms; Rp 05 represents an alkyl group, an alkoxy group, a halogen atom, a halogenated alkyl group, a cyano group or a hydroxy group; Rp 06 represents a linear or branched aliphatic hydrocarbon group; and n 1 represents an integer of 0 to 4;
wherein Rp 01 represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; Vp 01 represents a single bond or a divalent linking group; Rp 04 represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a halogenated alkyl group having 1 to 5 carbon atoms; Rp 05 represents an alkyl group, an alkoxy group, a halogen atom, a halogenated alkyl group, a cyano group or a hydroxy group; n 1 represents an integer of 0 to 4; Ra 004 and Ra 005 each independently represents a hydrogen atom or an alkyl group; Ra 006 represents a hydrocarbon group, provided that Ra 006 may be bonded to Ra 004 or Ra 005 to form a ring; and X represents a halogen atom.
10. A method of forming a resist pattern, comprising:
obtaining a polymeric compound (A02) represented by general formula (p2) by the method of producing a polymeric compound according to claim 9 ;
mixing the polymeric compound (A02) with an organic solvent to prepare a resist composition;
forming a resist film on a substrate using the resist composition;
exposing the resist film; and
developing the exposed resist film to form a resist pattern.