Iodine-containing polymers for chemically amplified resist compositions

A copolymer comprising a polymerized product of a monomer having formula (I) and a photoacid generator having formula (V):

• wherein in formula (I):
• W is —(C═O)O—, —O(C═O)—, —O(SO2)—, —(SO2)O—, —NH(SO2)—, —(SO2)NH—, —NH(CO)—, —(CO)NH—, —SO2—, —SO—,
• Ra is H, F, —CN, a C1-10 alkyl group, or a C1-10 fluoroalkyl group;
• L is a linking group selected from an unsubstituted or substituted C1-20 alkylene group, an unsubstituted or substituted C3-20 cycloalkylene group, an unsubstituted or substituted C6-20 arylene group, and an unsubstituted or substituted C7-20 aralkylene group;
• represents a monocyclic or polycyclic unsubstituted or substituted C6-30 arylene group or a monocyclic or polycyclic unsubstituted or substituted C3-30 heteroarylene group, wherein “*” indicates a point of attachment to a neighboring group or atom;
• “I” represents iodine;
• X is selected from —F, —Cl, —Br, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, an unsubstituted or substituted C1-30 alkyl group, an unsubstituted or substituted C2-30 alkenyl group, an unsubstituted or substituted C2-30 alkynyl group, an unsubstituted or substituted C1-30 alkoxy group, an unsubstituted or substituted C3-30 cycloalkyl group, an unsubstituted or substituted C1-30 heterocycloalkyl group, an unsubstituted or substituted C3-30 cycloalkenyl group, an unsubstituted or substituted C1-30 heterocycloalkenyl group, an unsubstituted or substituted C6-30 aryl group, an unsubstituted or substituted C6-30 aryloxy group, an unsubstituted or substituted C6-30 arylthio group, an unsubstituted or substituted C7-30 arylalkyl group, an unsubstituted or substituted C1-30 heteroaryl group, an unsubstituted or substituted C2-30 heteroaryloxy group, an unsubstituted or substituted C2-30 heteroarylthio group, or an unsubstituted or substituted C3-30 heteroarylalkyl group,
• wherein X optionally comprises an ester group or —C(CF3)2OH;
• m is an integer of 0 or greater, provided that when m is an integer of 2 or greater, two adjacent groups X optionally form a ring;
• and
• n is an integer of 1 or greater, provided that when m is 0, n is 3 or greater,
• wherein in Formula (V):
• Ra is independently H, F, C1-10 alkyl, or C1-10 fluoroalkyl;
• Q2 is a single bond or an ester-containing or non-ester containing, fluorinated or non-fluorinated group selected from a C1-20 alkylene group, a C3-20 cycloalkylene group, a C6-20 arylene group, and a C7-20 aralkylene group;
• A is an ester-containing or non ester-containing, fluorinated or non-fluorinated group selected from a C1-20 alkylene group, a C3-20 cycloalkylene group, a C6-20 arylene group, and a C7-20 aralkylene group;
• Z is an anionic moiety comprising sulfonate, an anion of a sulfonamide, or an anion of a sulfonimide;
• and
• G+ has formula (VII), (VIII), or (IX):
• wherein
• X is I or S,
• Rh, Ri, Rj, and Rk are unsubstituted or substituted and are each independently hydroxy, nitrile, halogen, a C1-30 alkyl group, a C1-30 fluoroalkyl group, a C3-30 cycloalkyl group, a C1-30 fluorocycloalkyl group, a C1-30 alkoxy group, a C3-30 alkoxycarbonylalkyl group, a C3-30 alkoxycarbonylalkoxy group, a C3-30 cycloalkoxy group, C5-30 a cycloalkoxycarbonylalkyl group, a C5-30 cycloalkoxycarbonylalkoxy group, a C1-30 fluoroalkoxy group, a C3-30 fluoroalkoxycarbonylalkyl group, a C3-30 fluoroalkoxycarbonylalkoxy group, a C3-30 fluorocycloalkoxy group, a C5-30 fluorocycloalkoxycarbonylalkyl group, a C5-30 fluorocycloalkoxycarbonylalkoxy group, a C6-30 aryl group, a C6-30 fluoroaryl group, a C6-30 aryloxy group, a C6-30 fluoroaryloxy group, or a C2-30 acetal group comprising —O—C(R11R12)—O— (wherein R11 and R12 are each independently hydrogen or a C1-30 alkyl group), each of which is unsubstituted or substituted;
• Ar1 and Ar2 are independently C10-30 fused or singly bonded polycyclic aryl groups;
• wherein X is S or I;
• p is an integer of 2 or 3,
• wherein when X is I, p is 2, and wherein when X is S, p is 3,
• g and r are each independently an integer from 0 to 5,
• u is an integer from 0 to 1, wherein when u is 0, X is I, and wherein when u is 1, X is S, and
• s and t are each independently an integer from 0 to 4,
• wherein at least one of Rh, Ri, Rj, and Rk is an acid-cleavable group.

A monomer having formula (I):

• wherein in formula (I):
• W is —(C═O)O—, —O(C═O)—, —O(SO2)—, —(SO2)O—, —NH(SO2)—, —(SO2)NH—, —NH(CO)—, —(CO)NH—, —SO2—, or —SO—, Ra is H, F, —CN, a C1-10 alkyl group, or a C1-10 fluoroalkyl group;
• L is a linking group selected from an unsubstituted or substituted C1-20 alkylene group, an unsubstituted or substituted C3-20 cycloalkylene group, an unsubstituted or substituted C6-20 arylene group, and an unsubstituted or substituted C7-20 aralkylene group;
• represents a monocyclic or polycyclic unsubstituted or substituted C6-30 arylene group or a monocyclic or polycyclic unsubstituted or substituted C3-30 heteroarylene group, wherein “*” indicates a point of attachment to a neighboring group or atom;
• “I” represents iodine;
• X is selected from a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, an unsubstituted or substituted C2-30 alkenyl group, an unsubstituted or substituted C2-30 alkynyl group, an unsubstituted or substituted C3-30 cycloalkyl group, an unsubstituted or substituted C1-30 heterocycloalkyl group, an unsubstituted or substituted C3-30 cycloalkenyl group, an unsubstituted or substituted C1-30 heterocycloalkenyl group, an unsubstituted or substituted C6-30 aryl group, an unsubstituted or substituted C6-30 aryloxy group, an unsubstituted or substituted C6-30 arylthio group, an unsubstituted or substituted C7-30 arylalkyl group, an unsubstituted or substituted C1-30 heteroaryl group, an unsubstituted or substituted C2-30 heteroaryloxy group, an unsubstituted or substituted C2-30 heteroarylthio group, or an unsubstituted or substituted C3-30 heteroarylalkyl group,
• wherein X optionally comprises an acid-cleavable group;
• m is an integer of 1 or greater, provided that when m is an integer of 2 or greater, two adjacent groups X optionally form a ring;
• and
• n is an integer of 1 or greater.