Iodine-containing polymers for chemically amplified resist compositions
View Patent ↗A monomer having formula (I): wherein in formula (I), groups and variables are the same as described in the specification.
1. A monomer having formula (I):
wherein in formula (I):
W is —(C═O)O—, —O(C═O)—, —O(SO 2 )—, —(SO 2 )O—, —NH(SO 2 )—, —(SO 2 )NH—, —NH(CO)—, —(CO)NH—, —SO 2 —, —SO—,
R a is H, F, —CN, a C 1-10 alkyl group, or a C 1-10 fluoroalkyl group;
L is a linking group selected from an unsubstituted or substituted C 1-20 alkylene group, an unsubstituted or substituted C 3-20 cycloalkylene group, an unsubstituted or substituted C 6-20 arylene group, and an unsubstituted or substituted C 7-20 aralkylene group;
represents a monocyclic or polycyclic unsubstituted or substituted C 6-30 arylene group or a monocyclic or polycyclic unsubstituted or substituted C 3-30 heteroarylene group, wherein “*” indicates a point of attachment to a neighboring group or atom;
“I” represents iodine;
X is selected from —F, —Cl, —Br, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino 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,
wherein at least one X comprises an ester group or —C(CF 3 ) 2 OH;
m is an integer of 1 or greater, provided that when m is an integer of 2 or greater, two adjacent groups X optionally form a ring; and
n is an integer of 1 or greater.
2. The monomer of claim 1 , wherein
L is a C 1-20 alkylene group substituted with —F, a hydroxyl group, or a C 1-10 alkyl group;
and
n is 1, 2, or 3.
3. A copolymer comprising a polymerized product of a monomer having formula (I) and a photoacid generator having formula (V):
wherein in formula (I):
W is —(C═O)O—, —O(C═O)—, —O(SO 2 )—, —(SO 2 )O—, —NH(SO 2 )—, —(SO 2 )NH—, —NH(CO)—, —(CO)NH—, —SO 2 —, —SO—,
R a is H, F, —CN, a C 1-10 alkyl group, or a C 1-10 fluoroalkyl group;
L is a linking group selected from an unsubstituted or substituted C 1-20 alkylene group, an unsubstituted or substituted C 3-20 cycloalkylene group, an unsubstituted or substituted C 6-20 arylene group, and an unsubstituted or substituted C 7-20 aralkylene group;
represents a monocyclic or polycyclic unsubstituted or substituted C 6-30 arylene group or a monocyclic or polycyclic unsubstituted or substituted C 3-30 heteroarylene group, wherein “*” indicates a point of attachment to a neighboring group or atom;
“I” represents iodine;
X is selected from —F, —Cl, —Br, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino 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,
wherein X optionally comprises an ester group or —C(CF 3 ) 2 OH;
m is an integer of 0 or greater, provided that when m is an integer of 2 or greater, two adjacent groups X optionally form a ring; and
n is an integer of 1 or greater, provided that when m is 0, n is 3 or greater,
wherein in Formula (V):
R a is independently H, F, C 1-10 alkyl, or C 1-10 fluoroalkyl;
Q 2 is a single bond or an ester-containing or non-ester containing, fluorinated or non-fluorinated group selected from a C 1-20 alkylene group, a C 3-20 cycloalkylene group, a C 6-20 arylene group, and a C 7-20 aralkylene group;
A is an ester-containing or non ester-containing, fluorinated or non-fluorinated group selected from a C 1-20 alkylene group, a C 3-20 cycloalkylene group, a C 6-20 arylene group, and a C 7-20 aralkylene group;
Z is an anionic moiety comprising sulfonate, an anion of a sulfonamide, or an anion of a sulfonimide; and
G + has formula (VII), (VIII), or (IX):
wherein
X is I or S,
R h , R i , R j , and R k are unsubstituted or substituted and are each independently hydroxy, nitrile, halogen, a C 1-30 alkyl group, a C 1-30 fluoroalkyl group, a C 3-30 cycloalkyl group, a C 1-30 fluorocycloalkyl group, a C 1-30 alkoxy group, a C 3-30 alkoxycarbonylalkyl group, a C 3-30 alkoxycarbonylalkoxy group, a C 3-30 cycloalkoxy group, C 5-30 a cycloalkoxycarbonylalkyl group, a C 5-30 cycloalkoxycarbonylalkoxy group, a C 1-30 fluoroalkoxy group, a C 3-30 fluoroalkoxycarbonylalkyl group, a C 3-30 fluoroalkoxycarbonylalkoxy group, a C 3-30 fluorocycloalkoxy group, a C 5-30 fluorocycloalkoxycarbonylalkyl group, a C 5-30 fluorocycloalkoxycarbonylalkoxy group, a C 6-30 aryl group, a C 6-30 fluoroaryl group, a C 6-30 aryloxy group, a C 6-30 fluoroaryloxy group, or a C 2-30 acetal group comprising —O—C(R 11 R 12 )—O— (wherein R 11 and R 12 are each independently hydrogen or a C 1-30 alkyl group), each of which is unsubstituted or substituted;
Ar 1 and Ar 2 are independently C 10-30 fused or singly bonded polycyclic aryl groups;
wherein X is S or I;
p is an integer of 2 or 3,
wherein when X is I, p is 2, and wherein when X is S, p is 3,
g and r are each independently an integer from 0 to 5,
u is an integer from 0 to 1, wherein when u is 0, X is I, and wherein when u is 1, X is S, and
s and t are each independently an integer from 0 to 4,
wherein at least one of R h , R i , R j , and R k is an acid-cleavable group.
4. The copolymer of claim 3 , further comprising a polymerized product of an acid-deprotectable monomer, a base-soluble monomer, a lactone-containing monomer, or a combination thereof.
5. The copolymer of claim 4 , wherein the acid-deprotectable monomer is represented by formula (II), the base-soluble monomer is represented by formula (III), and the lactone-containing monomer is represented by formula (IV):
wherein
each R a is independently H, F, C 1-10 alkyl, or C 1-10 fluoroalkyl;
each R b is independently H, an unsubstituted or substituted C 1-20 alkyl group, an unsubstituted or substituted C 3-20 cycloalkyl group, an unsubstituted or substituted C 6-20 aryl group, or an unsubstituted or substituted C 7-20 aralkyl group, and each R b is separate or at least one R b is bonded to an adjacent R b to form a cyclic structure;
Q 1 is an ester-containing or non-ester containing group selected from an unsubstituted or substituted C 1-20 alkyl group, an unsubstituted or substituted C 3-20 cycloalkyl group, an unsubstituted or substituted C 6-20 aryl group, and an unsubstituted or substituted C 7-20 aralkyl group;
W is a base-reactive group comprising at least one selected from —C(═O)—OH; —C(CF 3 ) 2 OH; —NH—SO 2 —Y 1 where Y 1 is F or a C 1-4 perfluoroalkyl group; an aromatic —OH; and an adduct of any of the foregoing with a vinyl ether;
a is an integer of 1 to 3; and
L is a monocyclic, polycyclic, or fused polycyclic C 4-20 lactone-containing group.
6. A photoresist composition comprising a copolymer of any of claims 3 to 5 .
7. The photoresist composition of claim 6 , further comprising a non-polymerizable photoacid generator having formula G + A − ,
wherein G + has formula (VI):
wherein
X is S or I,
each R c is unsubstituted or substituted, halogenated or non-halogenated, and is independently a C 1-30 alkyl group; a polycyclic or monocyclic C 3-30 cycloalkyl group; a polycyclic or monocyclic C 4-30 aryl group, wherein when X is S, one of the R c is optionally attached to one adjacent R c by a single bond, and
z is 2 or 3, wherein when X is I, z is 2, or when X is S, z is 3; and
wherein A − is a non-polymerizable organic anion.
8. The photoresist composition of claim 7 , wherein G + has formula (VII), (VIII), or (IX):
wherein
X is I or S,
R h , R i , R j , and R k are unsubstituted or substituted and are each independently hydroxy, nitrile, halogen, a C 1-30 alkyl group, a C 1-30 fluoroalkyl group, a C 3-30 cycloalkyl group, a C 1-30 fluorocycloalkyl group, a C 1-30 alkoxy group, a C 3-30 alkoxycarbonylalkyl group, a C 3-30 alkoxycarbonylalkoxy group, a C 3-30 cycloalkoxy group, C 5-30 a cycloalkoxycarbonylalkyl group, a C 5-30 cycloalkoxycarbonylalkoxy group, a C 1-30 fluoroalkoxy group, a C 3-30 fluoroalkoxycarbonylalkyl group, a C 3-30 fluoroalkoxycarbonylalkoxy group, a C 3-30 fluorocycloalkoxy group, a C 5-30 fluorocycloalkoxycarbonylalkyl group, a C 5-30 fluorocycloalkoxycarbonylalkoxy group, a C 6-30 aryl group, a C 6-30 fluoroaryl group, a C 6-30 aryloxy group, a C 6-30 fluoroaryloxy group, or a C 2-30 acetal group comprising —O—C(R 11 R 12 )—O— (wherein R 11 and R 12 are each independently hydrogen or a C 1-30 alkyl group), each of which is unsubstituted or substituted;
Ar 1 and Ar 2 are independently C 10-30 fused or singly bonded polycyclic aryl groups;
wherein X is S or I;
p is an integer of 2 or 3,
wherein when X is I, p is 2, and wherein when X is S, p is 3,
q and r are each independently an integer from 0 to 5,
u is an integer from 0 to 1, wherein when u is 0, X is I, and wherein when u is 1, X is S, and
s and t are each independently an integer from 0 to 4.
9. A coated substrate, comprising: (a) a substrate having one or more layers to be patterned on a surface thereof; and (b) a layer of a photoresist composition of any of claims 6 to 8 over the one or more layers to be patterned.
10. A method of forming an electronic device, comprising:
(a) applying a layer of the photoresist composition of any of claims 6 to 8 over a surface of the substrate;
(b) pattern-wise exposing the photoresist composition layer to activating radiation; and
(c) developing the exposed photoresist composition layer to provide a resist relief image.
11. A monomer having formula (I):
wherein in formula (I):
W is —(C═O)O—, —O(C═O)—, —O(SO 2 )—, —(SO 2 )O—, —NH(SO 2 )—, —(SO 2 )NH—, —NH(CO)—, —(CO)NH—, —SO 2 —, or —SO—, R a is H, F, —CN, a C 1-10 alkyl group, or a C 1-10 fluoroalkyl group;
L is a linking group selected from an unsubstituted or substituted C 1-20 alkylene group, an unsubstituted or substituted C 3-20 cycloalkylene group, an unsubstituted or substituted C 6-20 arylene group, and an unsubstituted or substituted C 7-20 aralkylene group;
represents a monocyclic or polycyclic unsubstituted or substituted C 6-30 arylene group or a monocyclic or polycyclic unsubstituted or substituted C 3-30 heteroarylene group, wherein “*” indicates a point of attachment to a neighboring group or atom;
“I” represents iodine;
X is selected from a cyano group, a nitro group, an amino group, an amidino 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 2-30 alkenyl group, an unsubstituted or substituted C 2-30 alkynyl 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,
wherein X optionally comprises an acid-cleavable group;
m is an integer of 1 or greater, provided that when m is an integer of 2 or greater, two adjacent groups X optionally form a ring; and
n is an integer of 1 or greater.
12. The monomer of claim 11 , wherein
n is 1, 2, or 3.
13. The monomer of claim 11 , wherein L is a C 1-20 alkylene group substituted with —F, a hydroxyl group, or a C 1-10 alkyl group.
14. The monomer of claim 11 , wherein X comprises an acid-cleavable group.