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US 12,761,556 B2Granted
Polymer, photoresist compositions including the same, and pattern formation methods
AssigneeDupont Electronic Materials International, LLC
InventorsTomas Marangoni, Huan He, Joshua Kaitz, Li Cui, Yinjie Cen, Emad Aqad, Mingqi Li
Life of this patent
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Abstract
A polymer including a first repeating unit comprising an acid labile group; an anionic endgroup selected from a carboxylate group or a sulfamate group; and an organic cation.
Claims16
A polymer, comprising:
- a first repeating unit comprising an acid labile group;
- an anionic endgroup selected from a carboxylate group or a sulfamate group;
- and
- an organic cation,
- wherein the polymer is a polymerization product of a monomer comprising the acid labile group in the presence of a compound of Formulae (9a) or (9b):
- wherein, in Formulae (9a) and (9b),
- R10 to R13 are each independently hydrogen, halogen, substituted or unsubstituted C1-30 alkyl, substituted or unsubstituted C3-30 cycloalkyl, substituted or unsubstituted C3-30 heterocycloalkyl, substituted or unsubstituted C2-30 alkenyl, substituted or unsubstituted C3-30 cycloalkenyl, substituted or unsubstituted C3-30 heterocycloalkenyl, substituted or unsubstituted C6-30 aryl, substituted or unsubstituted C7-30 arylalkyl, substituted or unsubstituted C7-30 alkylaryl, substituted or unsubstituted C2-30 heteroaryl, substituted or unsubstituted C3-30 heteroarylalkyl, or substituted or unsubstituted C3-30 alkylheteroaryl;
- provided that at least one of R10 and R11 is not hydrogen, and at least one of R12 and R13 is not hydrogen;
- R10 and R11 are optionally bonded together to form a ring, and R12 and R13 are optionally bonded together to form a ring;
- X is chlorine, bromine, iodine, or cyano;
- L11 is a divalent linking group;
- A− is a carboxylate group or a sulfamate group;
- and
- M+ is an organic cation.
11 more elements
A polymer, comprising:
- a first repeating unit comprising an acid labile group;
- an anionic endgroup selected from a carboxylate group or a sulfamate group;
- and
- an organic cation,
- wherein the polymer is a polymerization product of a monomer comprising the acid labile group in the presence of a compound of Formulae (10a), (10b), or (10c):
- wherein, in Formulae (10a) to (10c),
- R14 and R19 are each independently substituted or unsubstituted C1-30 alkyl, substituted or unsubstituted C3-30 cycloalkyl, substituted or unsubstituted C3-30 heterocycloalkyl, substituted or unsubstituted C6-30 aryl, substituted or unsubstituted C7-30 arylalkyl, substituted or unsubstituted C7-30 alkylaryl, substituted or unsubstituted C2-30 heteroaryl, substituted or unsubstituted C3-30 heteroarylalkyl, or substituted or unsubstituted C3-30 alkylheteroaryl;
- R15 to R18 are each independently hydrogen, halogen, substituted or unsubstituted C1-30 alkyl, substituted or unsubstituted C3-30 cycloalkyl, substituted or unsubstituted C3-30 heterocycloalkyl, substituted or unsubstituted C6-30 aryl, substituted or unsubstituted C7-30 arylalkyl, substituted or unsubstituted C7-30 alkylaryl, substituted or unsubstituted C2-30 heteroaryl, substituted or unsubstituted C3-30 heteroarylalkyl, or substituted or unsubstituted C3-30 alkylheteroaryl;
- R20 and R21 are each independently substituted or unsubstituted C1-30 alkyl, substituted or unsubstituted C3-30 cycloalkyl, substituted or unsubstituted C3-30 heterocycloalkyl, substituted or unsubstituted C6-30 aryl, substituted or unsubstituted C7-30 arylalkyl, substituted or unsubstituted C7-30 alkylaryl, substituted or unsubstituted C2-30 heteroaryl, substituted or unsubstituted C3-30 heteroarylalkyl, or substituted or unsubstituted C3-30 alkylheteroaryl;
- L12 is a divalent linking group;
- L13 is a single bond or a divalent linking group;
- L14 is a divalent linking group;
- each A− is a carboxylate group or a sulfamate group;
- and
- each M+ is an organic cation.
12 more elements
A polymer, comprising:
- a first repeating unit comprising an acid labile group;
- an anionic endgroup selected from a carboxylate group, a sulfonate group, or a sulfamate group;
- and
- an organic cation,
- wherein the polymer is a polymerization product of a monomer comprising the acid labile group in the presence of a compound represented by at least one of Formulae (9c), (10c), or (10d):
- wherein, in Formulae (9c), (10c), and (10d),
- R22 and R23 are each independently hydrogen, halogen, substituted or unsubstituted C1-30 alkyl, substituted or unsubstituted C3-30 cycloalkyl, substituted or unsubstituted C3-30 heterocycloalkyl, substituted or unsubstituted C2-30 alkenyl, substituted or unsubstituted C3-30 cycloalkenyl, substituted or unsubstituted C3-30 heterocycloalkenyl, substituted or unsubstituted C6-30 aryl, substituted or unsubstituted C7-30 arylalkyl, substituted or unsubstituted C7-30 alkylaryl, substituted or unsubstituted C2-30 heteroaryl, substituted or unsubstituted C3-30 heteroarylalkyl, or substituted or unsubstituted C3-30 alkylheteroaryl;
- provided that at least one of R22 and R23 is not hydrogen;
- R22 and R23 are optionally bonded together to form a ring;
- R24 and R25 are each independently substituted or unsubstituted C1-30 alkyl, substituted or unsubstituted C3-30 cycloalkyl, substituted or unsubstituted C3-30 heterocycloalkyl, substituted or unsubstituted C6-30 aryl, substituted or unsubstituted C7-30 arylalkyl, substituted or unsubstituted C7-30 alkylaryl, substituted or unsubstituted C2-30 heteroaryl, substituted or unsubstituted C3-30 heteroarylalkyl, or substituted or unsubstituted C3-30 alkylheteroaryl;
- R26 to R29 are each independently hydrogen, halogen, substituted or unsubstituted C1-30 alkyl, substituted or unsubstituted C3-30 cycloalkyl, substituted or unsubstituted C3-30 heterocycloalkyl, substituted or unsubstituted C6-30 aryl, substituted or unsubstituted C7-30 arylalkyl, substituted or unsubstituted C7-30 alkylaryl, substituted or unsubstituted C2-30 heteroaryl, substituted or unsubstituted C3-30 heteroarylalkyl, or substituted or unsubstituted C3-30 alkylheteroaryl;
- X is chlorine, bromine, iodine, or cyano;
- L15 and L16 are each independently a divalent linking group;
- L17 is a single bond or a divalent linking group;
- each A− is a carboxylate group, a sulfamate group, or a sulfonate group;
- and
- each M+ is an organic cation.
14 more elements
Dependencies are inferred from the claim text.