Aryl acetate onium materials
Acid generators comprising a carbocyclic aryl or heteroaromatic group substituted with at least one acetate moiety are provided. These acid generators are particularly useful as a photoresist composition component.
1. An acid generator that comprises a structure of Formula (I):
wherein:
Z is a counter anion;
X is sulfur or iodine;
R is optionally substituted alkyl, optionally substituted heteroalkyl, or optionally substituted alicyclic;
R′ and R″ are the same or different optionally substituted heteroalkyl, optionally substituted alicyclic, optionally substituted heteroalicyclic, optionally substituted carbocyclic aryl or optionally substituted heteroaromatic, provided that if X is iodine, one of R′ and R″ is absent; and
A is an optionally substituted carbocyclic aryl or optionally substituted heteroaromatic group, and
Z − comprises a structure of Formula (II):
wherein:
Y is a sulfonate, carboxylate, sulfate, sulfamate, or the anion of a sulfonamide or sulfonimide;
R′″ is a hydrogen or non-hydrogen substituent; and
W and W′ are independently chosen from hydrogen, fluorine, cyano, optionally substituted alkyl and optionally substituted aryl, wherein two or more of W, W′ and R′″ together optionally form a ring;
provided that when W and W′ are each independently fluorine or perfluoroalkyl, Y is chosen from carboxylate, sulfate, sulfamate, or the anion of a sulfonamide or sulfonimide.
2. An acid generator of claim 1 wherein the acid generator comprises a polymerizable moiety.
3. A photoresist composition comprising one or more acid generators of claim 1 .
4. A method for providing a photoresist relief image, comprising:
a) applying a coating layer of a photoresist composition of claim 3 on a substrate; and
b) exposing the photoresist composition layer to activating radiation and developing the exposed photoresist composition coating layer.
5. The acid generator of claim 1 wherein X is sulfur.
6. The acid generator of claim 1 wherein X is iodine.
7. The acid generator of claim 1 wherein R′ and R″ are the same or different optionally substituted heteroalkyl, optionally substituted alicyclic, optionally substituted heteroalicyclic, optionally substituted carbocyclic aryl.
8. An acid generator that comprises a structure of Formula (V):
wherein:
Z is a counter anion;
R 2 is H or is a group comprising an acid-labile moiety;
each T, each T′ and each T″ are the same or different non-hydrogen substituent, wherein either of T and T″ or T and T′ are capable of joining to form a ring;
n is 0, 1, 2, 3 or 4;
n′ and n″ are each independently 0, 1, 2, 3, 4 or 5;
J represents a chemical bond, or a group capable of covalently linking B and C;
D and D′ are the same or different and are each hydrogen or a non-hydrogen substituent, and optionally taken together may form a ring; and
A, B, and C are the same or different optionally substituted carbocyclic aryl or optionally substituted heteroaromatic group.
9. A photoresist composition comprising one or more acid generators of claim 8 .
10. A method for providing a photoresist relief image, comprising:
a) applying a coating layer of a photoresist composition of claim 9 on a substrate; and
b) exposing the photoresist composition layer to activating radiation and developing the exposed photoresist composition coating layer.
11. An acid generator that comprises a structure of Formula (I):
R′—X + —A—CH 2 —C(═O)—O—R Z − (I)
wherein:
Z is a counter anion;
X is iodine;
R is a non-hydrogen substituent;
R′ is an optionally substituted heteroalkyl, optionally substituted alicyclic, optionally substituted heteroalicyclic, optionally substituted carbocyclic aryl or optionally substituted heteroaromatic; and
A is an optionally substituted carbocyclic aryl or optionally substituted heteroaromatic group.
12. A photoresist composition comprising one or more acid generators of claim 11 .
13. A method for providing a photoresist relief image, comprising:
a) applying a coating layer of a photoresist composition of claim 12 on a substrate; and
b) exposing the photoresist composition layer to activating radiation and developing the exposed photoresist composition coating layer.
14. An acid generator that comprises a structure of Formula (I):
R′—X + —A—CH 2 —C(═O)—O—R Z − (I)
wherein:
Z is a counter anion;
X is iodine;
R is optionally substituted alkyl, optionally substituted heteroalkyl, or optionally substituted alicyclic;
R′ is a substituted heteroalkyl, optionally substituted alicyclic, optionally substituted heteroalicyclic, optionally substituted carbocyclic aryl or optionally substituted heteroaromatic; and
A is an optionally substituted carbocyclic aryl or optionally substituted heteroaromatic group.
15. A photoresist composition comprising one or more acid generators of claim 14 .
16. A method for providing a photoresist relief image, comprising:
a) applying a coating layer of a photoresist composition of claim 15 on a substrate; and
b) exposing the photoresist composition layer to activating radiation and developing the exposed photoresist composition coating layer.