Surface active additive and photoresist composition comprising same
View Patent ↗A polymer comprises the polymerized product of monomers comprising a nitrogen-containing monomer comprising formula (Ia), formula (Ib), or a combination of formulas (Ia) and (Ib), and an acid-deprotectable monomer having the formula (II): wherein a is 0 or 1, each R a is independently H, F, C 1-10 alkyl, or C 1-10 fluoroalkyl, L 1 is a straight chain or branched C 1-20 alkylene group, or a monocyclic, polycyclic, or fused polycyclic C 3-20 cycloalkylene group, each R b is independently H, C 1-10 alkyl, C 3-20 cycloalkyl, C 3-20 heterocycloalkyl, an aliphatic C 5-20 oxycarbonyl, or a C 1-30 acyl group optionally including a heteroatom substituent group, where each R b is separate or at least one R b is attached to an adjacent R b ; LN is a nitrogen-containing monocyclic, polycyclic, or fused polycyclic C 3-20 heterocycloalkylene group, and X is H, C 1-10 alkyl, aliphatic C 5-20 oxycarbonyl, or a C 1-30 acyl group optionally including a heteroatom substituent group; and each R c is independently C 1-10 alkyl, C 3-20 cycloalkyl, or C 3-20 heterocycloalkyl, wherein each R c is separate or at least one R c is attached to an adjacent R c .
1. A polymer, comprising the polymerized product of monomers comprising:
a nitrogen-containing monomer having the formula (Ic), and an acid-deprotectable monomer having the formula (II):
wherein:
each R a is independently H, F, C 1-10 alkyl, or C 1-10 fluoroalkyl;
LN is
wherein each R e is independently halogen or OR′, where R′ is H or C 1-10 alkyl, and b is an integer of 1 to 9;
each R c is independently C 1-10 alkyl, C 3-20 cycloalkyl, or C 3-20 heterocycloalkyl, wherein each R c is separate or at least one R c is attached to an adjacent R c ; and
each R d is independently C 1-10 alkyl, C 3-20 cycloalkyl, or C 3-20 heterocycloalkyl, and each R d is separate or at least one R d is attached to an adjacent R d .
2. A polymer, comprising the polymerized product of monomers comprising:
a nitrogen-containing monomer having the formula (Ic), and an acid-deprotectable monomer having the formula (II):
wherein:
each R a is independently H, F, C 1-10 alkyl, or C 1-10 fluoroalkyl;
LN is
wherein each R e is independently halogen or OR′, where R′ is H or C 1-10 alkyl, and b is an integer of 1 to 9;
each R c is independently C 1-10 alkyl, C 3-20 cycloalkyl, or C 3-20 heterocycloalkyl, wherein each R c is separate or at least one R c is attached to an adjacent R c ; and
each R d is independently C 1-10 alkyl, C 3-20 cycloalkyl, or C 3-20 heterocycloalkyl, and each R d is separate or at least one R d is attached to an adjacent R d ; and
wherein the acid deprotectable monomer of formula (II) is
or a combination comprising at least one of the foregoing, wherein each R a is independently H or C 1-4 alkyl.
3. A polymer, comprising the polymerized product of monomers comprising:
a nitrogen-containing monomer having the formula (Ic), an acid-deprotectable monomer having the formula (II), and a base-soluble monomer of formula (IV):
wherein
R a is H, F, C 1-10 alkyl, or C 1-10 fluoroalkyl,
LN is
wherein each R e is independently halogen, OR′, C 1-10 alkyl, or C 3-10 cycloalkyl, where R′ is H or C 1-10 alkyl, and b is an integer of 1 to 9;
each R c is independently C 1-10 alkyl, C 3-20 cycloalkyl, or C 3-20 heterocycloalkyl, wherein each R c is separate or at least one R c is attached to an adjacent R c ; and
each R d is independently C 1-10 alkyl, C 3-20 cycloalkyl, or C 3-20 heterocycloalkyl, and each R d is separate or at least one R d is attached to an adjacent R d ;
L 3 is a linear or branched C 1-20 alkylene, or C 3-20 cycloalkylene; and
Z is
wherein R f is a C 1-4 perfluoroalkyl group; and
c is an integer from 1 to 3.
4. The polymer of claim 3 , wherein the base-soluble monomer is:
or a combination comprising at least one of the foregoing monomers,
wherein R a is H, F, C 1-10 alkyl, or C 1-10 fluoroalkyl, and R f is a C 1-4 perfluoroalkyl group.
5. A polymer comprising the polymerized product of monomers comprising: a nitrogen-containing monomer having the formula (Ic), an acid-deprotectable monomer having the formula (II), and a surface-active monomer of formula (V):
wherein
each R a is independently H, F, C 1-10 alkyl, or C 1-10 fluoroalkyl;
LN is
wherein each R e is independently H, halogen, OR′, C 1-10 alkyl, or C 3-10 cycloalkyl, where R′ is H or C 1-10 alkyl, and b is an integer of 1 to 9;
each R c is independently C 1-10 alkyl, C 3-20 cycloalkyl, or C 3-20 heterocycloalkyl, wherein each R c is separate or at least one R c is attached to an adjacent R c ; and
each R d is independently C 1-10 alkyl, C 3-20 cycloalkyl, or C 3-20 heterocycloalkyl, and each R d is separate or at least one R d is attached to an adjacent R d ;
L 4 is an d+1 valent C 2-20 alkylene group or C 3-20 cycloalkylene group;
each R g is independently a C 1-22 alkyl or a C 1-4 fluoroalkyl, and each R g is optionally substituted with a functional group comprising an ether group, ester group, ketone group, OH group, or combination comprising at least one of the foregoing functional groups; and
d is an integer from 1 to 20.
6. The polymer of claim 5 , wherein the surface active monomer of formula (V) is
or a combination comprising at least one of the foregoing,
wherein R a is H, F, C 1-10 alkyl, or C 1-10 fluoroalkyl, and each R g is independently a C 1-4 fluoroalkyl group.