Photosensitive polymer, photoresist composition including the same, and method of fabricating semiconductor device
An extreme ultraviolet (EUV) photosensitive polymer includes a first repeating unit represented by Chemical Formula 1. (in Chemical Formula 1, R 1 is a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, a C6 to C18 aryl group, a haloaryl group, a C7 to C18 arylalkyl group, a C7 to C18 alkylaryl group, or a C6 to C18 haloaryl group, and R 2 is a direct bond, a C1 to C10 alkylene group, a C2 to C10 alkenyl group, a C2 to C10 alkynyl group, a C6 to C18 aryl group, a C7 to C18 arylalkyl group, or a C7 to C18 alkylaryl group).
1 . An extreme ultraviolet (EUV) photosensitive polymer comprising:
a first repeating unit represented by Chemical Formula 1:
wherein, in Chemical Formula 1, R 1 is a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, a C6 to C18 aryl group, a haloaryl group, a C7 to C18 arylalkyl group, a C7 to C18 alkylaryl group, or a C6 to C18 haloaryl group,
R 2 is a direct bond, a C1 to C10 alkylene group, a C1 to C10 haloalkylene group, a C2 to C10 alkenyl group, a C2 to C10 alkynyl group, a C6 to C18 aryl group, a C7 to C18 arylalkyl group, or a C7 to C18 alkylaryl group, and
the first repeating unit is 12% to 32% of a number of total repeating units;
a second repeating unit represented by Chemical Formula 2:
wherein, in Chemical Formula 2, R 3 is an acid-labile protecting group,
R 4 is a hydrogen atom, a C1 to C6 linear or branched alkyl group, a halogen atom, or a C1 to C6 linear or branched alkyl halide group, and
the second repeating unit is 25% to 65% of a number of total repeating units; and
a third repeating unit represented by Chemical Formula 3:
wherein, in Chemical Formula 3, R 5 is a hydrogen atom, a hydroxyl group, a carboxyl group, a C1 to C10 alkyl group, a C3 to C12 cycloalkyl group, or a C1 to C10 alkoxy group, and
R 6 is a hydrogen atom, a hydroxyl group, or a carboxyl group, and
the third repeating unit is 20% to 40% of a number of total repeating units.
2 . The EUV photosensitive polymer of claim 1 , wherein R 1 is a methyl group, a monofluoromethyl group, a monochloromethyl group, a difluoromethyl group, a dichloromethyl group, a trifluoromethyl group, a trichloromethyl group, an ethyl group, a monofluoroethyl group, a monochloroethyl group, a difluoroethyl group, a dichloroethyl group, a trifluoroethyl group, a trichloroethyl group, a monofluorophenyl group, a monochlorophenyl group, a difluorophenyl group, a dichlorophenyl group, a trifluorophenyl group, a trichlorophenyl group, a tetrafluorophenyl group, a tetrachlorophenyl group, a perfluorophenyl group, or a perchlorophenyl group.
3 . The EUV photosensitive polymer of claim 1 , wherein R 2 is the direct bond or the C6 to C18 aryl group.
4 . The EUV photosensitive polymer of claim 1 , wherein the first repeating unit is represented by one of Chemical Formulae 1-1 to 1-8:
5 . The EUV photosensitive polymer of claim 1 , further comprising:
a fourth repeating unit represented by Chemical Formula 4:
wherein, in Chemical Formula 4, R 7 is a C1 to C20 linear, branched, and/or cyclic saturated or unsaturated hydrocarbon group including 1 to 5 heteroatoms or including no heteroatom, and
R 8 is a hydrogen, a C1 to C3 alkyl group, a C2 to C4 alkenyl group, a C2 to C4 alkynyl group, a C1 to C3 alkoxy group, a C6 to C10 aryl group, a C3 to C7 cycloalkyl group, or a C3 to C7 cycloalkenyl group.
6 . A photoresist composition comprising:
a photosensitive polymer; and
a solvent,
wherein the photosensitive polymer comprises a first repeating unit represented by Chemical Formula 1:
wherein, in Chemical Formula 1, R 1 is a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, a C6 to C18 aryl group, a haloaryl group, a C7 to C18 arylalkyl group, a C7 to C18 alkylaryl group, or a C6 to C18 haloaryl group,
R 2 is a direct bond, a C1 to C10 alkylene group, a C2 to C10 alkenyl group, a C2 to C10 alkynyl group, a C6 to C18 aryl group, a C7 to C18 arylalkyl group, or a C7 to C18 alkylaryl group), and
the first repeating unit is 12% to 32% of a number of total repeating units
a second repeating unit represented by Chemical Formula 2:
wherein, in Chemical Formula 2, R 3 is an acid-labile protecting group,
R 4 is a hydrogen atom, a C1 to C6 linear or branched alkyl group, a halogen atom, or a C1 to C6 linear or branched alkyl halide group, and
the second repeating unit is 25% to 65% of a number of total repeating units; and
a third repeating unit represented by Chemical Formula 3:
wherein, in Chemical Formula 3, R 5 is a hydrogen atom, a hydroxyl group, a carboxyl group, a C1 to C10 alkyl group, a C3 to C12 cycloalkyl group, or a C1 to C10 alkoxy group, and
R 6 is a hydrogen atom, a hydroxyl group, or a carboxyl group, and
the third repeating unit is 20% to 40% of a number of total repeating units.
7 . The photoresist composition of claim 6 , wherein R 1 is a methyl group, a monofluoromethyl group, a monochloromethyl group, a difluoromethyl group, a dichloromethyl group, a trifluoromethyl group, a trichloromethyl group, an ethyl group, a monofluoroethyl group, a monochloroethyl group, a difluoroethyl group, a dichloroethyl group, a trifluoroethyl group, a trichloroethyl group, a monofluorophenyl group, a monochlorophenyl group, a difluorophenyl group, a dichlorophenyl group, a trifluorophenyl group, a trichlorophenyl group, a tetrafluorophenyl group, a tetrachlorophenyl group, a perfluorophenyl group, or a perchlorophenyl group.
8 . The photoresist composition of claim 6 , wherein R 2 is the direct bond, a methylene group, or the C6 to C18 aryl group.
9 . The photoresist composition of claim 6 , wherein the first repeating unit is represented by one of Chemical Chemical Formulae 1-1 to 1-8:
10 . The photoresist composition of claim 6 , further comprising: a photoacid generator (PAG).
11 . The photoresist composition of claim 10 , wherein the PAG is configured to generate an acid in response to irradiation by light having a wavelength of 13.5 nm.
12 . The photoresist composition of claim 10 , further comprising:
about 0.01 wt % to about 5 wt % of a basic quencher, based on a total weight of the photoresist composition.
13 . The photoresist composition of claim 6 , wherein R 1 is configured to dissociate from a −SO 3 group in response to irradiation by light having a wavelength of 13.5 nm.
14 . A photoresist composition comprising:
a photosensitive polymer;
a photoacid generator (PAG);
a basic quencher; and
a solvent,
wherein the photosensitive polymer comprises a random copolymer comprising a first repeating unit represented by Chemical Formula 1, a second repeating unit represented by Chemical Formula 2, and a third repeating unit represented by Chemical Formula 3:
wherein in Chemical Formulae 1 to 3, R 1 is a C1 to C10 alkyl group, a C1 to C10 haloalkyl group, a C6 to C18 aryl group, a haloaryl group, a C7 to C18 arylalkyl group, a C7 to C18 alkylaryl group, or a C6 to C18 haloaryl group,
R 2 is a direct bond, a C1 to C10 alkylene group, a C2 to C10 alkenyl group, a C2 to C10 alkynyl group, a C6 to C18 aryl group, a C7 to C18 arylalkyl group, or a C7 to C18 alkylaryl group,
R 3 is an acid-labile protecting group,
R 4 is a hydrogen atom, a C1 to C6 linear or branched alkyl group, a halogen atom, or a C1 to C6 linear or branched alkyl halide group,
R 5 is a hydrogen atom, a hydroxyl group, a carboxyl group, a C1 to C10 alkyl group, a C3 to C12 cycloalkyl group, or a C1 to C10 alkoxy group,
R 6 is a hydrogen atom, a hydroxyl group, or a carboxyl group,
the first repeating unit is 12% to 32% of a total of the first, second, and third repeating units
the second repeating unit is about 35% to about 65% of the total of the first, second, and
third repeating units, and the third repeating unit is about 20% to about 40% of the total of the first, second, and third repeating units.