Photoacid generators, photoresist compositions, and pattern formation methods
View Patent ↗Photoacid generators comprising a moiety of formula (1): wherein: Ar 1 is a substituted or unsubstituted aryl group; R 1 is an alkyl or aryl group, each of which may be substituted or unsubstituted, wherein Ar 1 and R 1 are optionally connected together by a single bond or a divalent linking group to form a ring; Y is a single bond or a divalent group; and * is the point of attachment of the moiety to another atom of the photoacid generator. The photoacid generator compounds find particular use in photoresist compositions that can be used to form lithographic patterns for the formation of electronic devices.
1 . A photoacid generator, comprising a moiety of formula (1):
wherein: Ar 1 is a substituted or unsubstituted aryl group; R 1 is an alkyl or aryl group, each of which may be substituted or unsubstituted, wherein Ar 1 and R 1 are optionally connected together by a single bond or a divalent linking group to form a ring; Y is a single bond or a divalent group; and * is the point of attachment of the moiety to another atom of the photoacid generator, wherein the photoacid generator is ionic and the moiety of formula (1) is attached to a cation of the photoacid generator.
2 . The photoacid generator of claim 1 , wherein the photoacid generator is represented by formula (2-1):
wherein: Ar 1 independently represents a substituted or unsubstituted aryl group; R 1 independently represents an alkyl or aryl group, each of which may be substituted or unsubstituted, wherein Ar 1 and R 1 are optionally connected together by a single bond or a divalent linking group to form a ring; Y independently represents a single bond or a divalent group; Ar 2 independently represents a substituted or unsubstituted arylene group; X is S or I; R 2 independently represents a substituted or unsubstituted alkyl or aryl group; Z − is a counter anion;
a is an integer from 1 to the total number of available carbon atoms on Ar 2; when X is S, bis 1, 2, or 3 and c is 3; and when X is I, b is 1 or 2 and c is 2; wherein (i) two R 2 groups or (ii) an Ar 2 group and an R 2 group are optionally connected together by a single bond or a divalent linking group to form a ring.
3 . The photoacid generator of claim 2 , wherein X is S.
4 . The photoacid generator of claim 2 , wherein X is I.
5 . The photoacid generator of claim 1 , wherein Ar 1 is a substituted aryl group.
6 . The photoacid generator of claim 1 , wherein the photoacid generator is in polymeric form.
7 . A photoresist composition, comprising a photoacid generator of claim 1 and a solvent.
8 . The photoresist composition of claim 7 , wherein the photoresist composition comprises an acid-sensitive polymer.
9 . A pattern formation method, comprising:
(a) forming a photoresist layer from a photoresist composition of claim 7 on a substrate;
(b) exposing the photoresist layer to activating radiation; and
(c) developing the exposed photoresist layer to provide a resist relief image.
10 . The pattern formation method of claim 9 , wherein the photoacid generator is represented by formula (2-1):
wherein: Ar 1 independently represents a substituted or unsubstituted aryl group; R 1 independently represents an alkyl or aryl group, each of which may be substituted or unsubstituted, wherein Ar 1 and R 1 are optionally connected together by a single bond or a divalent linking group to form a ring; Y independently represents a single bond or a divalent group; Ar 2 independently represents a substituted or unsubstituted arylene group; X is S or I; R 2 independently represents a substituted or unsubstituted alkyl or aryl group; Z − is a counter anion; a is an integer from 1 to the total number of available carbon atoms on Ar 2; when X is S, bis 1, 2, or 3 and c is 3; and when X is I, b is 1 or 2 and c is 2; wherein (i) two R 2 groups or (ii) an Ar 2 group and an R 2 group are optionally connected together by a single bond or a divalent linking group to form a ring.
11 . The pattern formation method of claim 10 , wherein Ar 1 is a substituted aryl group.
12 . The pattern formation method of claim 10 , wherein Ar 1 is substituted with an iodine atom.
13 . The photoacid generator of claim 5 , wherein Ar 1 is substituted with an iodine atom.
14 . The photoresist composition of claim 7 , wherein the photoacid generator is represented by formula (2-1):
wherein: Ar 1 independently represents a substituted or unsubstituted aryl group; R 1 independently represents an alkyl or aryl group, each of which may be substituted or unsubstituted, wherein Ar 1 and R 1 are optionally connected together by a single bond or a divalent linking group to form a ring; Y independently represents a single bond or a divalent group; Ar 2 independently represents a substituted or unsubstituted arylene group; X is S or I; R 2 independently represents a substituted or unsubstituted alkyl or aryl group; Z − is a counter anion; a is an integer from 1 to the total number of available carbon atoms on Ar 2 ; when X is S, b is 1, 2, or 3 and c is 3; and when X is I, b is 1 or 2 and c is 2; wherein (i) two R 2 groups or (ii) an Ar 2 group and an R 2 group are optionally connected together by a single bond or a divalent linking group to form a ring.
15 . The photoresist composition of claim 14 , wherein X is S.
16 . The photoresist composition of claim 14 , wherein X is I.
17 . The photoresist composition of claim 14 , wherein Ar 1 is a substituted aryl group.
18 . The photoresist composition of claim 17 , wherein Ar 1 is substituted with an iodine atom.
19 . The photoresist composition of claim 7 , wherein the photoacid generator is in polymeric form.