Iodine-containing photoacid generators and compositions comprising the same

A photoacid generator compound having formula (I):

• wherein, in formula (I):
• “I” represents iodine;
• V is OR1 or C(═O)OR1, wherein R1 is independently H or a substituted or unsubstituted C1-30 hydrocarbyl group optionally comprising 1 to 5 heteroatoms selected from O, S, N, P, and F, and optionally comprising an acid-cleavable group, a polymerizable group, or a combination thereof,
• W is a single bond or a group selected from —(C═O)O—, —O(C═O)—, —O(SO2)—, —(SO2)O—, —NH(SO2)—, —(SO2)NH—, —NH(CO)—, —(CO)NH—, —SO2—, and —SO—;
• m is an integer of 0 or greater;
• n is an integer of 0 or greater;
• L is a single bond, an unsubstituted C1-20 heteroalkylene group, a substituted or unsubstituted C3-20 cycloalkylene group, a substituted or unsubstituted C3-20 heterocycloalkylene group, a substituted or unsubstituted C7-20 aralkylene group, or a group having formula —(CH2)n1—(CR2R3)n2—, wherein R2 and R3 are selected from hydrogen and fluorine, provided that at least one of R2 and R3 in each —(CR2R3)— is fluorine, n1 is an integer of 0 to 10, and n2 is an integer of 1 to 10;
• 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 each “*” indicates a point of attachment to a neighboring group or atom;
• G+ has formula (II):
• wherein, in formula (II):
• X is S or I,
• each Rc is unsubstituted or substituted, halogenated or non-halogenated and is independently a C1-30 alkyl group;
• a polycyclic or monocyclic C3-30 cycloalkyl group;
• or a polycyclic or monocyclic C4-30 aryl group,
• wherein when X is S, one of the Rc is optionally attached to one adjacent Rc to form a ring, and the photoacid generator compound having formula (I) comprises at least two iodine atoms, and
• wherein when X is I, n is an integer of 1 or greater,
• wherein when X is S, n is an integer of 0 or greater, provided the photoacid generator having formula (I) comprises at least two iodine atoms,
• z is 2 or 3, wherein when X is I, z is 2, or when X is S, z is 3;
• and
• Y is CO2.

A photoacid generator compound having formula (I):

• wherein, in formula (I):
• “I” represents iodine;
• V is OR1 or C(═O)OR1, wherein R1 is independently H or a substituted or unsubstituted C1-30 hydrocarbyl group optionally comprising 1 to 5 heteroatoms selected from O, S, N, P, and F, and optionally comprising an acid-cleavable group, a polymerizable group, or a combination thereof;
• W is a single bond or a group selected from —(C═O)O—, —O(SO2)—, —(SO2)O—, —NH(SO2)—, —(SO2)NH—, —NH(CO)—, —(CO)NH—, —SO2—, and —SO—;
• m is an integer of 0 or greater;
• L is a single bond or a group having formula —(CH2)n1—(CR2R3)n2—, wherein R2 and R3 are selected from hydrogen and fluorine, provided that at least one of R2 and R3 in each —(CR2R3)— is fluorine, n1 is an integer of 0 to 10, and n2 is an integer of 2 to 10;
• 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 each “*” indicates a point of attachment to a neighboring group or atom;
• G+ has formula (II):
• wherein, in formula (II):
• X is I,
• each Rc is unsubstituted or substituted, halogenated or non-halogenated and is independently a C1-30 alkyl group;
• a polycyclic or monocyclic C3-30 cycloalkyl group;
• or a polycyclic or monocyclic C4-30 aryl group, and
• n is an integer of 1 or greater,
• z is 2;
• and
• Y is SO3, CO2, NHSO3, or O.

A photoacid generator compound having formula (I):

• wherein, in formula (I):
• “I” represents iodine;
• V is OR1 or C(═O)OR1, wherein R1 is independently H or a substituted or unsubstituted C1-30 hydrocarbyl group optionally comprising 1 to 5 heteroatoms selected from O, S, N, P, and F, and optionally comprising an acid-cleavable group, a polymerizable group, or a combination thereof,
• W is a single bond or a group selected from —(C═O)O—, —O(C═O)—, —O(SO2)—, —(SO2)O—, —NH(SO2)—, —(SO2)NH—, —NH(CO)—, —(CO)NH—, —SO2—, and —SO—;
• m is an integer of 0 or greater;
• n is an integer of 0 or greater;
• L is a single bond, a substituted or unsubstituted C1-20 alkylene group, a substituted or unsubstituted C1-20 heteroalkylene group, a substituted or unsubstituted C3-20 cycloalkylene group, a substituted or unsubstituted C3-20 heterocycloalkylene group, a substituted or unsubstituted C6-20 arylene group, or a substituted or unsubstituted 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 each “*” indicates a point of attachment to a neighboring group or atom;
• G+ has formula (II):
• wherein, in formula (II):
• X is S or I,
• each Rc is unsubstituted or substituted, halogenated or non-halogenated and is independently a C1-30 alkyl group;
• a polycyclic or monocyclic C3-30 cycloalkyl group;
• or a polycyclic or monocyclic C4-30 aryl group,
• wherein when X is S, one of the Rc is optionally attached to one adjacent Rc to form a ring, the photoacid generator compound having formula (I) comprises at least two iodine atoms, n is an integer of 1 or greater, and G+ comprises at least one iodine,
• z is 2 or 3, wherein when X is I, z is 2, or when X is S, z is 3;
• and
• Y is SO3, CO2, NHSO3, or O,
• wherein when X is I, G+ comprises at least one iodine in addition to the positively charged iodonium cation.