Zwitterionic photo-destroyable quenchers
A photo-destroyable quencher having Formula (I): wherein in Formula (I), groups and variables are the same as described in the specification.
1. A photo-destroyable quencher having Formula (I):
wherein
X is S or I,
each R 0 is attached to X, and is independently a C 1-30 alkyl group, a polycyclic or monocyclic C 3-30 cycloalkyl group, a polycyclic or monocyclic C 6-30 aryl group, or a combination comprising at least one of the foregoing, provided that at least one R 0 is a polycyclic or monocyclic C 6-30 aryl group;
r0 is 1 or 2, provided that when X is I, r0 is 1, and when X is S, r0 is 2, wherein when X is S, groups R 0 are optionally connected to each other so as to form a ring; and
Ar is a substituted or unsubstituted divalent C 6 -C 30 aromatic group;
L 1 and L 2 are each independently a divalent C 1 -C 30 linking group optionally comprising a heteroatom comprising O, S, N, F, or a combination comprising at least one of the foregoing heteroatoms;
M is a substituted or unsubstituted, divalent C 5 -C 30 or greater monocyclic, polycyclic, or fused polycyclic cycloaliphatic group, optionally comprising a heteroatom comprising O, S, N, F, or a combination comprising at least one of the foregoing;
Y is an oxygen-containing anionic group, provided that when X is S, Y is C(═O)O, O, or SO 2 NH; and
l 1 , l 2 , and m are each independently an integer of 0 or 1.
2. The photo-destroyable quencher according to claim 1 , wherein the compound of Formula (I) is represented by Formula (II):
wherein
each R 0 is independently a C 1-30 alkyl group, a polycyclic or monocyclic C 3-30 cycloalkyl group, a polycyclic or monocyclic C 6-30 aryl group, or a combination comprising at least one of the foregoing, provided that at least one R 0 is a polycyclic or monocyclic C 6-30 aryl group;
groups R 0 are optionally connected to each other so as to form a ring; and
Ar is a substituted or unsubstituted divalent C 6 -C 30 aromatic group;
L 1 and L 2 are each independently a divalent C 1 -C 30 linking group optionally comprising a heteroatom comprising O, S, N, F, or a combination comprising at least one of the foregoing heteroatoms;
M is a substituted or unsubstituted, divalent C 5 -C 30 or greater monocyclic, polycyclic, or fused polycyclic cycloaliphatic group, optionally comprising a heteroatom comprising O, S, N, F, or a combination comprising at least one of the foregoing;
Y is C(═O)O, O, or SO 2 NH; and
l 1 , l 2 , and m are each independently an integer of 0 or 1.
3. The photo-destroyable quencher according to claim 2 , wherein each R 0 is a polycyclic or monocyclic C 6-30 aryl group.
4. The photo-destroyable quencher according to claim 1 , wherein the photo-destroyable quencher having Formula (I) is represented by Formula (III) or Formula (IV):
wherein
K is a single bond or a divalent connecting group selected from S, O, NR (wherein R is H or a substituted or unsubstituted C 1 -C 5 alkyl group), S(═O), S(═O) 2 , C(═O), C(═O)O, OC(═O), a substituted or unsubstituted C 1 -C 5 alkylene group, or a combination thereof;
Ar is a substituted or unsubstituted divalent C 6 -C 30 aromatic group;
L 1 and L 2 are each independently a divalent C 1 -C 30 linking group optionally comprising a heteroatom comprising O, S, N, F, or a combination comprising at least one of the foregoing heteroatoms;
M is a substituted or unsubstituted, divalent C 5 -C 30 or greater monocyclic, polycyclic, or fused polycyclic cycloaliphatic group, optionally comprising a heteroatom comprising O, S, N, F, or a combination comprising at least one of the foregoing;
Y is C(═O)O, O, or SO 2 NH;
R 1 to R 4 are each independently a halogen, —CN, —OH, a C 1-10 alkyl group, a C 1-10 fluoroalkyl group, a C 1-10 alkoxy group, a C 1-10 fluoroalkoxy group, a C 3-10 cycloalkyl group, a C 3-10 fluorocycloalkyl group, a C 3-10 cycloalkoxy group, or a C 3-10 fluorocycloalkoxy group, each of which except a halogen, —CN, and —OH is substituted or unsubstituted, wherein two adjacent R 1 , two adjacent R 2 , two adjacent R 3 , or two adjacent R 4 optionally form a ring;
l 1 , l 2 , and m are each independently an integer of 0 or 1;
r 1 and r 2 are each independently an integer of 0 to 4; and
r 3 and r 4 are each independently an integer of 0 to 5.
5. The photo-destroyable quencher according to claim 1 , wherein Ar is a substituted or unsubstituted phenylene group.
6. The photo-destroyable quencher according to claim 1 , wherein when X is I, Y is C(═O)O, O, SO 2 NH, or SO 3 .
7. The photo-destroyable quencher according to claim 1 , wherein L 1 and L 2 are each independently a divalent C 1 -C 30 linking group comprising an —O—, —C(═O)—O—, —O—C(═O)—, —C(═O)—NR—, or —O—C(═O)—NR— moiety, wherein R is H or a substituted or unsubstituted C 1 -C 5 alkyl group.
8. The photo-destroyable quencher according to claim 1 , wherein M is a C 19 or less adamantyl group, a C 19 or less norbornanyl group, a C 7-20 lactone-containing group, a C 20 steroidal group, or C 20 or greater non-steroidal organic group.
9. The photo-destroyable quencher according to claim 1 , wherein
(i) l 1 is 0, l 2 is 0, and m is 0;
(ii) l 1 is 1, l 2 is 0 or 1, and m is 0; or
(iii) l 1 is 1, l 2 is 1, and m is 1.
10. The photo-destroyable quencher according to claim 1 , wherein L 2 comprises a substituted or unsubstituted C 1-30 alkylene group, a substituted or unsubstituted C 6-30 arylene group, a substituted or unsubstituted C 7-30 aralkylene group, or combination comprising at least one of the foregoing.
11. A composition comprising:
an acid-sensitive polymer;
a photoacid generator; and
the photo-destroyable quencher of claim 1 .
12. A coated substrate comprising: (a) a substrate having one or more layers to be patterned on a surface thereof; and (b) a layer of the composition of claim 11 disposed over the one or more layers to be patterned.
13. A method of making a relief image, the method comprising
coating a substrate having a layer comprising
an acid-sensitive polymer,
a photoacid generator, and
a photo-destroyable quencher having Formula (I):
wherein
X is S or I,
each R 0 is attached to X, and is independently a C 1-30 alkyl group, a polycyclic or monocyclic C 3-30 cycloalkyl group, a polycyclic or monocyclic C 6-30 aryl group, or a combination comprising at least one of the foregoing, provided that at least one R 0 is a polycyclic or monocyclic C 6-30 aryl group;
r0 is 1 or 2, provided that when X is I, r0 is 1, and when X is S, r0 is 2, wherein when X is S, groups R 0 are optionally connected to each other so as to form a ring; and
Ar is a substituted or unsubstituted divalent C 6 -C 30 aromatic group;
L 1 and L 2 are each independently a divalent C 1 -C 30 linking group optionally comprising a heteroatom comprising O, S, N, F, or a combination comprising at least one of the foregoing heteroatoms;
M is a substituted or unsubstituted, divalent C 5 -C 30 or greater monocyclic, polycyclic, or fused polycyclic cycloaliphatic group, optionally comprising a heteroatom comprising O, S, N, F, or a combination comprising at least one of the foregoing;
Y is an oxygen-containing anionic group, provided that when X is S, Y is C(═O)O, O, or SO 2 NH; and
l 1 , l 2 , and m are each independently an integer of 0 or 1,
pattern-wise exposing the composition layer to activating radiation; and
developing the exposed photoresist composition layer to provide a resist relief image.
14. A photo-destroyable quencher having Formula (II-A):
wherein
each R 0 is independently a C 1-30 alkyl group, a polycyclic or monocyclic C 3-30 cycloalkyl group, a polycyclic C 6-30 aryl group, a monocyclic C 6-30 aryl group substituted with halogen, or a combination comprising at least one of the foregoing, provided that at least one R 0 is a polycyclic C 6-30 aryl group or a monocyclic C 6-30 aryl group substituted with halogen;
groups R 0 are optionally connected to each other so as to form a ring; and
Ar is a substituted or unsubstituted divalent C 6 -C 30 aromatic group;
L 1 and L 2 are each independently a divalent C 1 -C 30 linking group optionally comprising a heteroatom comprising O, S, N, F, or a combination comprising at least one of the foregoing heteroatoms;
M is a substituted or unsubstituted, divalent C 5 -C 30 or greater monocyclic, polycyclic, or fused polycyclic cycloaliphatic group, optionally comprising a heteroatom comprising O, S, N, F, or a combination comprising at least one of the foregoing; and
l 1 , l 2 , and m are each independently an integer of 0 or 1.
15. A composition comprising:
an acid-sensitive polymer;
a photoacid generator; and
the photo-destroyable quencher of claim 14 .
16. A coated substrate comprising: (a) a substrate having one or more layers to be patterned on a surface thereof; and (b) a layer of the composition of claim 15 disposed over the one or more layers to be patterned.
17. A method of making a relief image, the method comprising coating a substrate having a layer comprising
an acid-sensitive polymer,
a photoacid generator, and
a photo-destroyable quencher having Formula (II-A):
wherein
each R 0 is independently a C 1-30 alkyl group, a polycyclic or monocyclic C 3-30 cycloalkyl group, a polycyclic C 6-30 aryl group, a monocyclic C 6-30 aryl group substituted with halogen, or a combination comprising at least one of the foregoing, provided that at least one R 0 is a polycyclic C 6-30 aryl group or a monocyclic C 6-30 aryl group substituted with halogen;
groups R 0 are optionally connected to each other so as to form a ring; and
Ar is a substituted or unsubstituted divalent C 6 -C 30 aromatic group;
L 1 and L 2 are each independently a divalent C 1 -C 30 linking group optionally comprising a heteroatom comprising O, S, N, F, or a combination comprising at least one of the foregoing heteroatoms;
M is a substituted or unsubstituted, divalent C 5 -C 30 or greater monocyclic, polycyclic, or fused polycyclic cycloaliphatic group, optionally comprising a heteroatom comprising O, S, N, F, or a combination comprising at least one of the foregoing; and
l 1 , l 2 , and m are each independently an integer of 0 or 1,
pattern-wise exposing the composition layer to activating radiation; and
developing the exposed photoresist composition layer to provide a resist relief image.