Coating composition for photoresist underlayer
A coating composition comprising a crosslinkable polyester polymer comprising an isocyanurate group and a crosslinkable group; a crosslinker; and an acid catalyst, wherein at least one of the crosslinkable polyester polymer and the crosslinker comprises an iodine-containing polymer.
1. A coating composition, comprising:
a crosslinkable polyester polymer comprising an isocyanurate group and a crosslinkable group;
a crosslinker; and
an acid catalyst;
wherein the crosslinker comprises an iodine-containing polymer.
2. The coating composition of claim 1 , wherein the crosslinkable polyester polymer comprises an iodine-containing polyester polymer derived from a compound of Formula (1):
wherein, in Formula (I),
D is a single bond, or an unsubstituted or substituted C 1-4 alkylene group;
Y is —H, —OH, —C(O)OH, —C(O)OR b , or epoxy;
R b is hydrogen, an unsubstituted or substituted C 1-10 alkyl group, an unsubstituted or substituted C 3-30 cycloalkyl group, an unsubstituted or substituted C 1-30 heterocycloalkyl group, an unsubstituted or substituted C 6-30 aryl group, an unsubstituted or substituted C 7-30 arylalkyl group, an unsubstituted or substituted C 1-30 heteroaryl group, or an unsubstituted or substituted C 3-30 heteroarylalkyl group;
I is an iodine atom;
each X is independently —F, —Cl, —Br, a hydroxyl group, a cyano group, a nitro group, an amino group, an amido 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 C 1-30 alkyl group, an unsubstituted or substituted C 2-30 alkenyl group, an unsubstituted or substituted C 2-30 alkynyl group, an unsubstituted or substituted C 1-30 alkoxy group, an unsubstituted or substituted C 3-30 cycloalkyl group, an unsubstituted or substituted C 1-30 heterocycloalkyl group, an unsubstituted or substituted C 3-30 cycloalkenyl group, an unsubstituted or substituted C 1-30 heterocycloalkenyl group, an unsubstituted or substituted C 6-30 aryl group, an unsubstituted or substituted C 6-30 aryloxy group, an unsubstituted or substituted C 6-30 arylthio group, an unsubstituted or substituted C 7-30 arylalkyl group, an unsubstituted or substituted C 1-30 heteroaryl group, an unsubstituted or substituted C 2-30 heteroaryloxy group, an unsubstituted or substituted C 2-30 heteroarylthio group, or an unsubstituted or substituted C 3-30 heteroarylalkyl group; and
m is an integer of 0 to 4; n is an integer of 1 to 3; and the sum of m and n is less than 6.
3. The coating composition of claim 2 , wherein
in Formula (1), D is a single bond and Y is —OH, —C(O)OH, or epoxy; or
the compound of Formula (1) has a structure of Formula (1a):
wherein, in Formula (1a),
R b is an unsubstituted or substituted C 1-10 alkyl group, an unsubstituted or substituted C 3-30 cycloalkyl group, an unsubstituted or substituted C 1-30 heterocycloalkyl group, an unsubstituted or substituted C 6-30 aryl group, an unsubstituted or substituted C 7-30 arylalkyl group, an unsubstituted or substituted C 1-30 heteroaryl group, or an unsubstituted or substituted C 3-30 heteroarylalkyl group; and
I, X, m, and n are the same as in claim 2 .
4. The coating composition of claim 2 , wherein the crosslinkable polyester polymer comprises an isocyanurate repeating unit derived from a monomer of Formula (2):
wherein, in Formula (2),
K, L, and M are each independently a linear or branched C 1-10 hydrocarbon group, a C 1-10 alkoxycarbonyl group, a C 1-10 alkanoyloxy group, each of which is optionally substituted with a carboxylic acid group, or a linear or branched C 1-10 hydroxyalkyl group optionally substituted with a C 1-5 alkoxycarbonyl group or a C 1-5 substituted alkoxy group,
wherein each of the C 1-10 hydrocarbon group, the C 1-10 alkoxycarbonyl group, the C 1-10 alkanoyloxy group, and the C 1-10 hydroxyalkyl group is optionally substituted with at least one of a halogen, an amino group, a thiol group, an epoxy group, an amido group, a C 1-5 alkyl group, a C 3-8 cycloalkyl group, a C 3-20 heterocycloalkyl group, a C 2-5 alkenyl group, a C 1-5 alkoxy group, a C 2-5 alkenoxy group, a C 6-10 aryl group, a C 6-10 aryloxy group, a C 7-10 alkylaryl group, or C 7-10 alkylaryloxy group, and
wherein at least one hydrogen atom of the polyester polymer is substituted with a functional group independently chosen from hydroxyl, carboxyl, thiol, amino, epoxy, alkoxy, amido, vinyl, and a combination thereof.
5. The coating composition of claim 1 , wherein the crosslinker comprises an iodine-containing poly(meth)acrylate polymer derived from a monomer of Formula (3):
wherein, in Formula (3),
R a is hydrogen, fluorine, cyano, a C 1-10 alkyl group, or a C 1-10 fluoroalkyl group;
A is an unsubstituted or substituted C 1-30 alkylene group, an unsubstituted or substituted C 3-30 cycloalkylene group, an unsubstituted or substituted C 1-30 heterocycloalkylene group, an unsubstituted or substituted C 6-30 arylene group, an unsubstituted or substituted divalent C 7-30 arylalkyl group, an unsubstituted or substituted C 1-30 heteroarylene group, or an unsubstituted or substituted divalent C 3-30 heteroarylalkyl group;
L is —O—, —O(C═O)—, —(C═O)O—, —O(SO 2 )—, —(SO 2 )O—, —NH(SO 2 )—, —(SO 2 )NH—, —NH(CO)—, —(CO)NH—, —SO 2 —, or —SO—;
I is an iodine atom;
each X is independently —F, —Cl, —Br, a hydroxyl group, a cyano group, a nitro group, an amino group, an amido 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 C 1-30 alkyl group, an unsubstituted or substituted C 2-30 alkenyl group, an unsubstituted or substituted C 2-30 alkynyl group, an unsubstituted or substituted C 1-30 alkoxy group, an unsubstituted or substituted C 3-30 cycloalkyl group, an unsubstituted or substituted C 1-30 heterocycloalkyl group, an unsubstituted or substituted C 3-30 cycloalkenyl group, an unsubstituted or substituted C 1-30 heterocycloalkenyl group, an unsubstituted or substituted C 6-30 aryl group, an unsubstituted or substituted C 6-30 aryloxy group, an unsubstituted or substituted C 6-30 arylthio group, an unsubstituted or substituted C 7-30 arylalkyl group, an unsubstituted or substituted C 1-30 heteroaryl group, an unsubstituted or substituted C 2-30 heteroaryloxy group, an unsubstituted or substituted C 2-30 heteroarylthio group, or an unsubstituted or substituted C 3-30 heteroarylalkyl group; and
m is an integer of 0 to 4; n is an integer of 1 to 3; and the sum of m and n is less than 6.
6. The coating composition of claim 5 , wherein the iodine-containing poly(meth)acrylate polymer comprises a functional group selected from hydroxyl, carboxyl, thiol, amino, epoxy, alkoxy, amido, vinyl, or a combination thereof.
7. The coating composition of claim 1 , wherein the crosslinkable group of the crosslinkable polymer comprises a functional group selected from hydroxyl, carboxyl, thiol, amino, epoxy, alkoxy, amido, vinyl, or a combination thereof.
8. The coating composition of claim 1 , further comprising a solvent.
9. A coated substrate comprising:
a layer of the coating composition of claim 8 disposed on a substrate; and
a photoresist layer disposed on the layer of the coating composition.
10. The coated substrate of claim 9 , wherein the crosslinkable polyester polymer comprises an iodine-containing polyester polymer derived from a compound of Formula (1):
wherein, in Formula (I),
D is a single bond, or an unsubstituted or substituted C 1-4 alkylene group;
Y is —H, —OH, —C(O)OH, —C(O)OR b , or epoxy;
R b is hydrogen, an unsubstituted or substituted C 1-10 alkyl group, an unsubstituted or substituted C 3-30 cycloalkyl group, an unsubstituted or substituted C 1-30 heterocycloalkyl group, an unsubstituted or substituted C 6-30 aryl group, an unsubstituted or substituted C 7-30 arylalkyl group, an unsubstituted or substituted C 1-30 heteroaryl group, or an unsubstituted or substituted C 3-30 heteroarylalkyl group;
I is an iodine atom;
each X is independently —F, —Cl, —Br, a hydroxyl group, a cyano group, a nitro group, an amino group, an amido 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 C 1-30 alkyl group, an unsubstituted or substituted C 2-30 alkenyl group, an unsubstituted or substituted C 2-30 alkynyl group, an unsubstituted or substituted C 1-30 alkoxy group, an unsubstituted or substituted C 3-30 cycloalkyl group, an unsubstituted or substituted C 1-30 heterocycloalkyl group, an unsubstituted or substituted C 3-30 cycloalkenyl group, an unsubstituted or substituted C 1-30 heterocycloalkenyl group, an unsubstituted or substituted C 6-30 aryl group, an unsubstituted or substituted C 6-30 aryloxy group, an unsubstituted or substituted C 6-30 arylthio group, an unsubstituted or substituted C 7-30 arylalkyl group, an unsubstituted or substituted C 1-30 heteroaryl group, an unsubstituted or substituted C 2-30 heteroaryloxy group, an unsubstituted or substituted C 2-30 heteroarylthio group, or an unsubstituted or substituted C 3-30 heteroarylalkyl group; and
m is an integer of 0 to 4; n is an integer of 1 to 3; and the sum of m and n is less than 6.
11. The coated substrate of claim 9 , wherein the crosslinker comprises an iodine-containing poly(meth)acrylate polymer derived from a monomer of Formula (3):
wherein, in Formula (3),
R a is hydrogen, fluorine, cyano, a C 1-10 alkyl group, or a C 1-10 fluoroalkyl group;
A is an unsubstituted or substituted C 1-30 alkylene group, an unsubstituted or substituted C 3-30 cycloalkylene group, an unsubstituted or substituted C 1-30 heterocycloalkylene group, an unsubstituted or substituted C 6-30 arylene group, an unsubstituted or substituted divalent C 7-30 arylalkyl group, an unsubstituted or substituted C 1-30 heteroarylene group, or an unsubstituted or substituted divalent C 3-30 heteroarylalkyl group;
L is —O—, —O(C═O)—, —(C═O)O—, —O(SO 2 )—, —(SO 2 )O—, —NH(SO 2 )—, —(SO 2 )NH—, —NH(CO)—, —(CO)NH—, —SO 2 —, or —SO—;
I is an iodine atom;
each X is independently —F, —Cl, —Br, a hydroxyl group, a cyano group, a nitro group, an amino group, an amido 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 C 1-30 alkyl group, an unsubstituted or substituted C 2-30 alkenyl group, an unsubstituted or substituted C 2-30 alkynyl group, an unsubstituted or substituted C 1-30 alkoxy group, an unsubstituted or substituted C 3-30 cycloalkyl group, an unsubstituted or substituted C 1-30 heterocycloalkyl group, an unsubstituted or substituted C 3-30 cycloalkenyl group, an unsubstituted or substituted C 1-30 heterocycloalkenyl group, an unsubstituted or substituted C 6-30 aryl group, an unsubstituted or substituted C 6-30 aryloxy group, an unsubstituted or substituted C 6-30 arylthio group, an unsubstituted or substituted C 7-30 arylalkyl group, an unsubstituted or substituted C 1-30 heteroaryl group, an unsubstituted or substituted C 2-30 heteroaryloxy group, an unsubstituted or substituted C 2-30 heteroarylthio group, or an unsubstituted or substituted C 3-30 heteroarylalkyl group; and
m is an integer of 0 to 4; n is an integer of 1 to 3; and the sum of m and n is less than 6.
12. The coated substrate of claim 11 , wherein the iodine-containing poly(meth)acrylate polymer comprises a functional group selected from hydroxyl, carboxyl, thiol, amino, epoxy, alkoxy, amido, vinyl, or a combination thereof.
13. The coated substrate of claim 9 , wherein the crosslinkable group of the crosslinkable polymer comprises a functional group selected from hydroxyl, carboxyl, thiol, amino, epoxy, alkoxy, amido, vinyl, or a combination thereof.
14. A method of forming an electronic device, comprising:
applying a layer of the coating composition of claim 8 on a substrate;
curing the coating composition to form an underlayer film;
applying a layer of a photoresist composition on the underlayer film to form a photoresist layer;
pattern-wise exposing the photoresist layer to radiation; and
developing the exposed photoresist layer to provide a resist relief image.
15. The method of claim 14 , wherein the crosslinkable polyester polymer comprises an iodine-containing polyester polymer derived from a compound of Formula (1):
wherein, in Formula (I),
D is a single bond, or an unsubstituted or substituted C 1-4 alkylene group;
Y is —H, —OH, —C(O)OH, —C(O)OR b , or epoxy;
R b is hydrogen, an unsubstituted or substituted C 1-10 alkyl group, an unsubstituted or substituted C 3-30 cycloalkyl group, an unsubstituted or substituted C 1-30 heterocycloalkyl group, an unsubstituted or substituted C 6-30 aryl group, an unsubstituted or substituted C 7-30 arylalkyl group, an unsubstituted or substituted C 1-30 heteroaryl group, or an unsubstituted or substituted C 3-30 heteroarylalkyl group;
I is an iodine atom;
each X is independently —F, —Cl, —Br, a hydroxyl group, a cyano group, a nitro group, an amino group, an amido 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 C 1-30 alkyl group, an unsubstituted or substituted C 2-30 alkenyl group, an unsubstituted or substituted C 2-30 alkynyl group, an unsubstituted or substituted C 1-30 alkoxy group, an unsubstituted or substituted C 3-30 cycloalkyl group, an unsubstituted or substituted C 1-30 heterocycloalkyl group, an unsubstituted or substituted C 3-30 cycloalkenyl group, an unsubstituted or substituted C 1-30 heterocycloalkenyl group, an unsubstituted or substituted C 6-30 aryl group, an unsubstituted or substituted C 6-30 aryloxy group, an unsubstituted or substituted C 6-30 arylthio group, an unsubstituted or substituted C 7-30 arylalkyl group, an unsubstituted or substituted C 1-30 heteroaryl group, an unsubstituted or substituted C 2-30 heteroaryloxy group, an unsubstituted or substituted C 2-30 heteroarylthio group, or an unsubstituted or substituted C 3-30 heteroarylalkyl group; and
m is an integer of 0 to 4; n is an integer of 1 to 3; and the sum of m and n is less than 6.
16. The method of claim 15 , wherein
in Formula (1), D is a single bond and Y is —OH, —C(O)OH, or epoxy; or
the compound of Formula (1) has a structure of Formula (1a):
wherein, in Formula (1a),
R b is an unsubstituted or substituted C 1-10 alkyl group, an unsubstituted or substituted C 3-30 cycloalkyl group, an unsubstituted or substituted C 1-30 heterocycloalkyl group, an unsubstituted or substituted C 6-30 aryl group, an unsubstituted or substituted C 7-30 arylalkyl group, an unsubstituted or substituted C 1-30 heteroaryl group, or an unsubstituted or substituted C 3-30 heteroarylalkyl group; and
I, X, m, and n are the same as in claim 15 .
17. The method of claim 15 , wherein the crosslinkable polyester polymer comprises an isocyanurate repeating unit derived from a monomer of Formula (2):
wherein, in Formula (2),
K, L, and M are each independently a linear or branched C 1-10 hydrocarbon group, a C 1-10 alkoxycarbonyl group, a C 1-10 alkanoyloxy group, each of which is optionally substituted with a carboxylic acid group, or a linear or branched C 1-10 hydroxyalkyl group optionally substituted with a C 1-5 alkoxycarbonyl group or a C 1-5 substituted alkoxy group,
wherein each of the C 1-10 hydrocarbon group, the C 1-10 alkoxycarbonyl group, the C 1-10 alkanoyloxy group, and the C 1-10 hydroxyalkyl group is optionally substituted with at least one of a halogen, an amino group, a thiol group, an epoxy group, an amido group, a C 1-5 alkyl group, a C 3-8 cycloalkyl group, a C 3-20 heterocycloalkyl group, a C 2-5 alkenyl group, a C 1-5 alkoxy group, a C 2-5 alkenoxy group, a C 6-10 aryl group, a C 6-10 aryloxy group, a C 7-10 alkylaryl group, or C 7-10 alkylaryloxy group, and
wherein at least one hydrogen atom of the polyester polymer is substituted with a functional group independently chosen from hydroxyl, carboxyl, thiol, amino, epoxy, alkoxy, amido, vinyl, and a combination thereof.
18. The method of claim 14 , wherein the crosslinker comprises an iodine-containing poly(meth)acrylate polymer derived from a monomer of Formula (3):
wherein, in Formula (3),
R a is hydrogen, fluorine, cyano, a C 1-10 alkyl group, or a C 1-10 fluoroalkyl group;
A is an unsubstituted or substituted C 1-30 alkylene group, an unsubstituted or substituted C 3-30 cycloalkylene group, an unsubstituted or substituted C 1-30 heterocycloalkylene group, an unsubstituted or substituted C 6-30 arylene group, an unsubstituted or substituted divalent C 7-30 arylalkyl group, an unsubstituted or substituted C 1-30 heteroarylene group, or an unsubstituted or substituted divalent C 3-30 heteroarylalkyl group;
L is —O—, —O(C═O)—, —(C═O)O—, —O(SO 2 )—, —(SO 2 )O—, —NH(SO 2 )—, —(SO 2 )NH—, —NH(CO)—, —(CO)NH—, —SO 2 —, or —SO—;
I is an iodine atom;
each X is independently —F, —Cl, —Br, a hydroxyl group, a cyano group, a nitro group, an amino group, an amido 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 C 1-30 alkyl group, an unsubstituted or substituted C 2-30 alkenyl group, an unsubstituted or substituted C 2-30 alkynyl group, an unsubstituted or substituted C 1-30 alkoxy group, an unsubstituted or substituted C 3-30 cycloalkyl group, an unsubstituted or substituted C 1-30 heterocycloalkyl group, an unsubstituted or substituted C 3-30 cycloalkenyl group, an unsubstituted or substituted C 1-30 heterocycloalkenyl group, an unsubstituted or substituted C 6-30 aryl group, an unsubstituted or substituted C 6-30 aryloxy group, an unsubstituted or substituted C 6-30 arylthio group, an unsubstituted or substituted C 7-30 arylalkyl group, an unsubstituted or substituted C 1-30 heteroaryl group, an unsubstituted or substituted C 2-30 heteroaryloxy group, an unsubstituted or substituted C 2-30 heteroarylthio group, or an unsubstituted or substituted C 3-30 heteroarylalkyl group; and
m is an integer of 0 to 4; n is an integer of 1 to 3; and the sum of m and n is less than 6.
19. The method of claim 18 , wherein the iodine-containing poly(meth)acrylate polymer comprises a functional group selected from hydroxyl, carboxyl, thiol, amino, epoxy, alkoxy, amido, vinyl, or a combination thereof.
20. The method of claim 14 , wherein the crosslinkable group of the crosslinkable polymer comprises a functional group selected from hydroxyl, carboxyl, thiol, amino, epoxy, alkoxy, amido, vinyl, or a combination thereof.