PHOTORESIST COMPOSITIONS AND PATTERN FORMATION METHODS

1 . A photoresist composition, comprising:

an acid-sensitive polymer comprising a first repeating unit formed from a first free radical polymerizable monomer comprising an acid-decomposable group and a second repeating unit formed from a second free radical polymerizable monomer comprising a carboxylic acid group;

a compound comprising two or more enol ether groups, wherein the compound is different from the acid-sensitive polymer;

a material comprising a base-labile group;

a photoacid generator; and

a solvent.

2 . The photoresist composition of claim 1 , wherein the compound is of formula (5):

wherein: R 14 independently represents —H, C 1-4 alkyl, or C 1-4 fluoroalkyl, optionally including as part of its structure one or more groups chosen from —O—, —S—, —N(R 15 )—, —C(O)—, —C(O)O—, or —C(O)N(R 15 )—, wherein R 15 represents hydrogen or substituted or unsubstituted C 1-10 alkyl, and any two R 14 groups together optionally forming a ring; L 5 represents a linking group have a valency of d; and d is an integer from 2 to 4.

3 . The photoresist composition of claim 2 , wherein the compound is of formula (5-1):

CH 2 ═CH—O—R 17 —O—CH═CH 2   (5-1)

wherein R 17 represents C 1-10 linear alkylene, C 3-10 branched alkylene, C 3-10 cyclic alkylene, or a combination thereof, each of which may be substituted or unsubstituted.

4 . The photoresist composition of claim 1 , wherein the compound is a polymer comprising a first repeating unit comprising an enol ether group that is pendant to a polymer backbone.

5 . The photoresist composition of claim 4 , wherein the first repeating unit of the compound is formed from a vinyl aromatic monomer or a (meth)acrylate monomer.

6 . The photoresist composition of claim 1 , wherein the acid-decomposable group is a tertiary ester group of the formula —C(═O)OC(R 5 ) 3 wherein: R 5 is each independently linear C 1-20 alkyl, branched C 3-20 alkyl, monocyclic or polycyclic C 3-20 cycloalkyl, linear C 2-20 alkenyl, branched C 3-20 alkenyl, monocyclic or polycyclic C 3-20 cycloalkenyl, monocyclic or polycyclic C 6-20 aryl, or monocyclic or polycyclic C 2-20 heteroaryl, preferably linear C 1-6 alkyl, branched C 3-6 alkyl, or monocyclic or polycyclic C 3-10 cycloalkyl, each of which is substituted or unsubstituted, each R 5 optionally including as part of its structure one or more groups chosen from —O—, —S—, —N(R 6 )—, —C(O)—, —C(O)O—, or —C(O)N(R 6 )—, wherein R 6 represents hydrogen or substituted or unsubstituted C 1-10 alkyl, and any two R 5 groups together optionally forming a ring.

7 . The photoresist composition of claim 1 , wherein the first free radical polymerizable monomer and the second free radical polymerizable monomer are independently a vinyl aromatic monomer or a (meth)acrylate monomer.

8 . The photoresist composition of claim 1 , wherein the photosensitive polymer further comprises a third repeating unit comprising a lactone group.

9 . The photoresist composition of claim 1 , wherein the material comprising a base-labile group is a fluorinated polymer.

10 . A pattern formation method, comprising:

(a) applying a layer of a photoresist composition of claim 1 , on a substrate;

(b) soft-baking the photoresist composition layer;

(b) exposing the soft-baked photoresist composition layer to activating radiation;

(d) post-exposure baking the photoresist composition layer; and

(c) developing the post-exposure baked photoresist composition layer to provide a resist relief image.

11 . The method of claim 10 , wherein the compound is of formula (5):

wherein: R 14 independently represents —H, C 1-4 alkyl, or C 1-4 fluoroalkyl, optionally including as part of its structure one or more groups chosen from —O—, —S—, —N(R 15 )—, —C(O)—, —C(O)O—, or —C(O)N(R 15 )—, wherein R 15 represents hydrogen or substituted or unsubstituted C 1-10 alkyl, and any two R 14 groups together optionally forming a ring; L 5 represents a linking group have a valency of d; and d is an integer from 2 to 4.

12 . The photoresist composition of claim 11 , wherein the compound is of formula (5-1):

CH 2 ═CH—O—R 17 —O—CH═CH 2   (5-1)

wherein R 17 represents C 1-10 linear alkylene, C 3-10 branched alkylene, C 3-10 cyclic alkylene, or a combination thereof, each of which may be substituted or unsubstituted.

13 . The photoresist composition of claim 10 , wherein the compound is a polymer comprising a first repeating unit comprising an enol ether group that is pendant to a polymer backbone.

14 . The photoresist composition of claim 13 , wherein the first repeating unit of the compound is formed from a vinyl aromatic monomer or a (meth)acrylate monomer.

15 . The photoresist composition of claim 10 , wherein the acid-decomposable group is a tertiary ester group of the formula —C(═O)OC(R 5 ) 3 wherein: R 5 is each independently linear C 1-20 alkyl, branched C 3-20 alkyl, monocyclic or polycyclic C 3-20 cycloalkyl, linear C 2-20 alkenyl, branched C 3-20 alkenyl, monocyclic or polycyclic C 3-20 cycloalkenyl, monocyclic or polycyclic C 6-20 aryl, or monocyclic or polycyclic C 2-20 heteroaryl, preferably linear C 1-6 alkyl, branched C 3-6 alkyl, or monocyclic or polycyclic C 3-10 cycloalkyl, each of which is substituted or unsubstituted, each R 5 optionally including as part of its structure one or more groups chosen from —O—, —S—, —N(R 6 )—, —C(O)—, —C(O)O—, or —C(O)N(R 6 )—, wherein R 6 represents hydrogen or substituted or unsubstituted C 1-10 alkyl, and any two R 5 groups together optionally forming a ring.

16 . The photoresist composition of claim 10 , wherein the first free radical polymerizable monomer and the second free radical polymerizable monomer are independently a vinyl aromatic monomer or a (meth)acrylate monomer.

17 . The photoresist composition of claim 10 , wherein the photosensitive polymer further comprises a third repeating unit comprising a lactone group.

18 . The photoresist composition of claim 10 , wherein the material comprising a base-labile group is a fluorinated polymer.