Coating composition for use with an overcoated photoresist
A method for forming a photoresist relief image including applying a layer of a coating composition on a substrate; and disposing a layer of a photoresist composition on the layer of the coating composition, wherein the coating composition comprises an amine-containing polymer comprising a hydrocarbon-substituted amino group and having nitrogen atoms in an amount from 3 to 47 weight percent, based on a total weight of the amine-containing polymer.
1. A method for forming a photoresist relief image, the method comprising:
applying a layer of a coating composition on a substrate; and
disposing a layer of a photoresist composition on the layer of the coating composition,
wherein the coating composition comprises an amine-containing polymer comprising a hydrocarbon-substituted amino group and having nitrogen atoms in an amount from 3 to 47 weight percent, based on a total weight of the amine-containing polymer,
wherein the amine-containing polymer comprises a repeating structural unit represented by at least one of Formulae (1) or (2):
wherein, in Formulae (1) and (2),
R 1 to R 3 are each independently hydrogen, a substituted or unsubstituted C 1-10 alkyl group, a substituted or unsubstituted C 3-10 cycloalkyl group, or a substituted or unsubstituted C 6-20 aryl group;
L 1 is a substituted or unsubstituted C 1-30 alkylene group, a substituted or unsubstituted C 2-30 alkenylene group, a substituted or unsubstituted C 1-30 heteroalkene group, a substituted or unsubstituted C 3-7 heterocycloalkylene group, a substituted or unsubstituted C 6-30 arylene group, a substituted or unsubstituted C 3-30 heteroarylene group, —O—, —C(═O)O—, —O(C═O)—, —CONR b —, or —OC(═O)NR b —;
L 2 is a single bond, a substituted or unsubstituted C 1-30 alkylene group, a substituted or unsubstituted C 2-30 alkenylene group, a substituted or unsubstituted C 1-30 heteroalkene group, a substituted or unsubstituted C 3-7 heterocycloalkylene group, a substituted or unsubstituted C 6-30 arylene group, a substituted or unsubstituted C 3-30 heteroarylene group, —(C(R c )═N—(C 2-3 )alkylene) n -, —(NR b —(C 2-3 )alkylene) n —, or —(O—(C 2-3 alkylene) n -;
X 1 is —N(R b ) 2 or a substituted or unsubstituted nitrogen-containing monocyclic, polycyclic, or fused polycyclic C 2-7 heterocycloalkyl group or C 3-30 heteroaryl group;
X 2 is —C(R c )═NR b , —N═C(R c ) 2 , —(NR b —(C 2-3 )alkylene) n -N(R b ) 2 , —(O—(C 2-3 )alkylene) n -N(R b ) 2 , or a substituted or unsubstituted nitrogen-containing monocyclic, polycyclic, or fused polycyclic C 2-7 heterocycloalkyl group or C 3-30 heteroaryl group;
each R b is independently hydrogen, a substituted or unsubstituted C 1-30 alkyl group, a substituted or unsubstituted polycyclic or monocyclic C 3-30 cycloalkyl group, or a substituted or unsubstituted polycyclic or monocyclic C 6-30 aryl group;
each R c is independently hydrogen, a halogen, a cyano group, a nitro group, an amino group, a substituted or unsubstituted C 1-30 alkyl group, a substituted or unsubstituted C 2-30 alkenyl group, a substituted or unsubstituted C 2-30 alkynyl group, a substituted or unsubstituted C 1-30 alkoxy group, a substituted or unsubstituted C 3-30 cycloalkyl group, a substituted or unsubstituted C 3-30 cycloalkenyl group, a substituted or unsubstituted C 6-30 aryl group, a substituted or unsubstituted C 6-30 aryloxy group, a substituted or unsubstituted C 6-30 arylthio group, or a substituted or unsubstituted C 7-30 arylalkyl group; and
each n is independently an integer from 1 to 20.
2. The method of claim 1 , further comprising
disposing an additional layer directly on the layer of the coating composition; and
disposing the layer of the photoresist composition directly on the additional layer,
wherein the additional layer comprises at least one of a hardmask layer, a silicon-containing layer, or organic layer.
3. The method of claim 1 , wherein in Formulae (1) and (2),
R 1 to R 3 are hydrogen;
L 1 is a C 6-30 arylene group, —C(═O)O—, or —CONR b —;
L 2 is single bond, a C 1-10 alkylene group, a C 2-10 alkenylene group, a C 1-20 heteroalkene group, a C 3-7 heterocycloalkylene group, a C 6-12 arylene group, a C 3-12 heteroarylene group, —(C(R c )═N—(C 2-3 )alkylene) n -, —(NR b —(C 2-3 )alkylene) n -, or —(O—(C 2-3 )alkylene) n -;
X 1 is a substituted or unsubstituted nitrogen-containing monocyclic C 2-7 heterocycloalkyl group or C 3-30 heteroaryl group;
X 2 is —C(R c )═NR b , —N═C(R c ) 2 , —(NR b —(C 2-3 )alkylene) n -N(R b ) 2 , —(O—(C 2-3 )alkylene n -N(R b ) 2 , or a substituted or unsubstituted nitrogen-containing monocyclic C 2-7 heterocycloalkyl group or C 3-30 heteroaryl group;
each R b is independently hydrogen, a substituted or unsubstituted C 1-10 alkyl group, a substituted or unsubstituted polycyclic or monocyclic C 3-10 cycloalkyl group, or a substituted or unsubstituted polycyclic or monocyclic C 6-12 aryl group;
each R c is independently hydrogen, a halogen, a substituted or unsubstituted C 1-10 alkyl group, a substituted or unsubstituted C 2-10 alkenyl group, a substituted or unsubstituted C 2-10 alkynyl group, a substituted or unsubstituted C 1-10 alkoxy group, a substituted or unsubstituted C 3-10 cycloalkyl group, a substituted or unsubstituted C 3-10 cycloalkenyl group, a substituted or unsubstituted C 6-12 aryl group, a substituted or unsubstituted C 6-12 aryloxy group, a substituted or unsubstituted C 6-12 arylthio group, or a substituted or unsubstituted C 7-10 arylalkyl group; and
each n is independently an integer from 1 to 5.
4. The method of claim 1 , wherein the amine-containing polymer has a weight average molecular weight from 1,000 to 100,000 grams per mole, as determined by gel permeation chromatography.
5. The method of claim 1 , wherein the coating composition further comprises a crosslinking agent.
6. The method of claim 1 , wherein the coating composition further comprises a thermal acid generator or a thermal base generator.
7. A method for forming a photoresist relief image, the method comprising:
applying a layer of a coating composition on a substrate; and
disposing a layer of a photoresist composition on the layer of the coating composition,
wherein the coating composition comprises an amine-containing polymer comprising a hydrocarbon-substituted amino group and having nitrogen atoms in an amount from 3 to 47 weight percent, based on a total weight of the amine-containing polymer,
wherein the amine-containing polymer comprises a repeating structural unit represented by at least one of Formulae (3) or (4):
wherein, in Formulae (3) and (4),
R 1 and R 2 are each independently hydrogen, a substituted or unsubstituted C 1-10 alkyl group, a substituted or unsubstituted C 3-10 cycloalkyl group, or a substituted or unsubstituted C 6-20 aryl group;
Q 2 is a substituted or unsubstituted aliphatic group, a substituted or unsubstituted cycloaliphatic group, a substituted or unsubstituted aromatic group, a substituted or unsubstituted heteroaromatic group, and combinations thereof, optionally with one or more linking moiety chosen from —O—, —N(R b )—, —COO—, —CONR b —, —CONR b —, and —OCONR b —, and wherein Q 2 is optionally a branching group connected to at least two repeat units represented by Formula (3);
Ar is a substituted or unsubstituted C 6-18 arylene group or a substituted or unsubstituted C 3-18 heteroarylene group;
X 3 is a substituted or unsubstituted nitrogen-containing monocyclic, polycyclic, or fused polycyclic C 2-7 heterocycloalkyl group or C 3-30 heteroaryl group;
R a is hydrogen or a substituted or unsubstituted C 1-30 alkyl group; and
each R b is independently hydrogen, a substituted or unsubstituted C 1-30 alkyl group, a substituted or unsubstituted polycyclic or monocyclic C 3-30 cycloalkyl group, or a substituted or unsubstituted polycyclic or monocyclic C 6-30 aryl group.
8. The method of claim 7 , wherein in Formulae (3) and (4),
R 1 and R 2 are hydrogen;
Q 2 is a substituted or unsubstituted aliphatic group, a substituted or unsubstituted cycloaliphatic group, a substituted or unsubstituted aromatic group, a substituted or unsubstituted heteroaromatic group, and combinations thereof, optionally with one or more linking moiety chosen from —O—, —N(R b )—, —COO—, —CONR b —, —CONR b —, and —OCONR b —;
Ar is a substituted or unsubstituted phenylene group;
R a is hydrogen; and
each R b is independently hydrogen, a substituted or unsubstituted C 1-10 alkyl group, a substituted or unsubstituted polycyclic or monocyclic C 3-10 cycloalkyl group, or a substituted or unsubstituted polycyclic or monocyclic C 6-12 aryl group.
9. The method of claim 7 , further comprising:
disposing an additional layer directly on the layer of the coating composition; and
disposing the layer of the photoresist composition directly on the additional layer,
wherein the additional layer comprises at least one of a hardmask layer, a silicon-containing layer, or organic layer.
10. The method of claim 7 , wherein the amine-containing polymer has a weight average molecular weight from 1,000 to 100,000 grams per mole, as determined by gel permeation chromatography.
11. The method of claim 7 , wherein the coating composition further comprises a crosslinking agent.
12. The method of claim 7 , wherein the coating composition further comprises a thermal acid generator or a thermal base generator.
13. A coating composition for use with an overcoated photoresist composition, the coating composition comprising an amine-containing polymer comprising a hydrocarbon-substituted amino group and having nitrogen atoms in an amount from 3 to 47 weight percent, based on a total weight of the amine-containing polymer,
wherein the amine-containing polymer comprises a repeating structural unit represented by at least one of Formulae (1) or (2):
wherein, in Formulae (1) and (2),
R 1 to R 3 are each independently hydrogen, a substituted or unsubstituted C 1-10 alkyl group, a substituted or unsubstituted C 3-10 cycloalkyl group, or a substituted or unsubstituted C 6-20 aryl group;
L 1 is a substituted or unsubstituted C 1-30 alkylene group, a substituted or unsubstituted C 2-30 alkenylene group, a substituted or unsubstituted C 1-30 heteroalkene group, a substituted or unsubstituted C 3-7 heterocycloalkylene group, a substituted or unsubstituted C 6-30 arylene group, a substituted or unsubstituted C 3-30 heteroarylene group, —O—, —C(═O)O—, —O(C═O)—, —CONR b —, or —OC(═O)NR b —;
L 2 is a single bond, a substituted or unsubstituted C 1-30 alkylene group, a substituted or unsubstituted C 2-30 alkenylene group, a substituted or unsubstituted C 1-30 heteroalkene group, a substituted or unsubstituted C 3-7 heterocycloalkylene group, a substituted or unsubstituted C 6-30 arylene group, a substituted or unsubstituted C 3-30 heteroarylene group, —(C(R c )═N—(C 2-3 )alkylene) n -, —(NR b —(C 2-3 )alkylene) n -, or —(O—(C 2-3 )alkylene) n -;
X 1 is —N(R b ) 2 or a substituted or unsubstituted nitrogen-containing monocyclic, polycyclic, or fused polycyclic C 2-7 heterocycloalkyl group or C 3-30 heteroaryl group;
X 2 is —C(R c )═NR b , —N═C(R c ) 2 , —(NR b —(C 2-3 )alkylene) n -N(R b ) 2 , —(O—(C 2-3 )alkylene) n -N(R b ) 2 , or a substituted or unsubstituted nitrogen-containing monocyclic, polycyclic, or fused polycyclic C 2-7 heterocycloalkyl group or C 3-30 heteroaryl group;
each R b is independently hydrogen, a substituted or unsubstituted C 1-30 alkyl group, a substituted or unsubstituted polycyclic or monocyclic C 3-30 cycloalkyl group, or a substituted or unsubstituted polycyclic or monocyclic C 6-30 aryl group;
each R c is independently hydrogen, a halogen, a cyano group, a nitro group, an amino group, a substituted or unsubstituted C 1-30 alkyl group, a substituted or unsubstituted C 2-30 alkenyl group, a substituted or unsubstituted C 2-30 alkynyl group, a substituted or unsubstituted C 1-30 alkoxy group, a substituted or unsubstituted C 3-30 cycloalkyl group, a substituted or unsubstituted C 3-30 cycloalkenyl group, a substituted or unsubstituted C 6-30 aryl group, a substituted or unsubstituted C 6-30 aryloxy group, a substituted or unsubstituted C 6-30 arylthio group, or a substituted or unsubstituted C 7-30 arylalkyl group; and
each n is independently an integer from 1 to 20.
14. A coated substrate, comprising:
a layer of the coating composition of claim 13 disposed on a substrate; and
a layer of a photoresist composition disposed on the layer of the coating composition.
15. A coating composition for use with an overcoated photoresist composition, the coating composition comprising an amine-containing polymer comprising a hydrocarbon-substituted amino group and having nitrogen atoms in an amount from 3 to 47 weight percent, based on a total weight of the amine-containing polymer,
wherein the amine-containing polymer comprises a repeating structural unit represented by at least one of Formulae (3) or (4):
wherein, in Formulae (3) and (4),
R 1 and R 2 are each independently hydrogen, a substituted or unsubstituted C 1-10 alkyl group, a substituted or unsubstituted C 3-10 cycloalkyl group, or a substituted or unsubstituted C 6-20 aryl group;
Q 2 is a substituted or unsubstituted aliphatic group, a substituted or unsubstituted cycloaliphatic group, a substituted or unsubstituted aromatic group, a substituted or unsubstituted heteroaromatic group, and combinations thereof, optionally with one or more linking moiety chosen from —O—, —N(R b )—, —COO—, —CONR b —, —CONR b —, and —OCONR b —, and wherein Q 2 is optionally a branching group connected to at least two repeat units represented by Formula (3);
Ar is a substituted or unsubstituted C 6-18 arylene group or a substituted or unsubstituted C 3-18 heteroarylene group;
X 3 is —N(R b ) 2 or a substituted or unsubstituted nitrogen-containing monocyclic, polycyclic, or fused polycyclic C 2-7 heterocycloalkyl group or C 3-30 heteroaryl group;
R a is hydrogen or a substituted or unsubstituted C 1-30 alkyl group; and
each R b is independently hydrogen, a substituted or unsubstituted C 1-30 alkyl group, a substituted or unsubstituted polycyclic or monocyclic C 3-30 cycloalkyl group, or a substituted or unsubstituted polycyclic or monocyclic C 6-30 aryl group.