Polymer composition, photoresist comprising the polymer composition, and coated article comprising the photoresist

1. A copolymer, comprising the polymerized product of:

a dissolution-rate controlling monomer having the formula (I), an acyclic vinyl ether of the formula (II), and a cyclic vinyl ether of the formula (III):

wherein R a is H, F, C 1-10 alkyl, or C 1-10 fluoroalkyl, provided R a is C 1-10 fluoroalkyl for at least one instance of the monomer of formula (I),

X is O or NR wherein R is H, a C 1-10 alkyl, or a C 6-10 aryl,

Z 1 is a C 1-20 alkyl, C 3-20 cycloalkyl, C 6-20 aryl, or C 7-20 aralkyl, each optionally substituted with hydroxyl, sulfonate, sulfonic acid, sulfonamide, sulfonimide, carboxylic acid, ester, carbonate, amide, or a combination thereof,

each R b is independently H or a group selected from C 1-20 alkyl, C 3-20 cycloalkyl, C 6-20 aryl, or C 7-20 aralkyl wherein each group is optionally substituted with —F, or a combination thereof, wherein two or more of the foregoing groups are optionally linked with —C(═O)—O—,

R c is a group selected from C 1-20 alkyl, C 3-20 cycloalkyl, C 6-20 aryl, or C 7-20 aralkyl wherein each R c group is optionally substituted with —F or —OH, or a combination thereof, wherein two or more of the foregoing groups are optionally linked with —O—, —S—, —NR—, or —C(═O)—O—, and

L is a linear C 1-20 alkylene, C 1-20 alkylene-C(═O)*, C 3-20 cycloalkylene, C 6-20 arylene, or C 7-20 aralkylene each optionally substituted with —F, —OH, or a combination thereof, wherein * indicates a point of attachment of the C 1-20 alkylene-C(═O) to a double bond of the cyclic vinyl ether of the formula (III), and

wherein an amount of the acyclic vinyl ether of the formula (II) is from greater than 0 mol % to 20 mol % based on the total monomer amount.

2. The copolymer of claim 1 , wherein monomer (I) is a base soluble cycloalkyl monomer of formula (I-a), a hydroxyaromatic monomer of formula (I-b), an acid-deprotectable monomer of formula (I-c), or a combination thereof:

wherein

R a is H, F, C 1-10 alkyl, or C 1-10 fluoroalkyl, provided R a is C 1-10 fluoroalkyl for at least one of monomer (I-a), (I-b), or (I-c),

is an (HO) y -substituted linear or branched C 1-20 alkylene, (HO) y -substituted C 3-20 cycloalkylene, (HO) y -substituted C 5-20 polycycloalkylene, or (HO) y -substituted fused C 6-20 polycycloalkylene, wherein

is optionally substituted with F,

is an (HO) y -substituted C 6-20 arylene, or (HO) y -substituted C 7-20 aralkylene, wherein

is optionally substituted with F,

each R d is independently C 1-20 alkyl, C 3-20 cycloalkyl, C 6-20 aryl, or C 7-20 aralkyl, and each R d is only commonly attached to a single carbon atom or at least one R d is further bonded to an adjacent R d to form a cyclic structure,

x is independently an integer of from 0 to 3, y is 0 or 1, and x+y>0.

3. The copolymer of claim 2 , wherein the base soluble cycloalkyl monomer has formula (I-a-1) and the base soluble aromatic monomer has formula (I-b-1):

wherein each R a is independently C 1-10 fluoroalkyl,

x in (I-a-1) is an integer of from 1 to 3, y is 0 or 1, and

x in (I-b-1) is an integer of from 0 to 3, y is 0 or 1, and x+y>0.

4. The copolymer of claim 2 , wherein the acid deprotectable monomer comprises:

or a combination thereof, wherein R a is C 1-6 fluoroalkyl for at least one monomer, or where a combination of monomers is used, R a is H, F, C 1-6 alkyl, or C 1-6 fluoroalkyl, provided R a is C 1-6 fluoroalkyl for at least one monomer.

5. The copolymer of claim 1 , wherein the acyclic vinyl ether of the formula (II) includes:

or a combination thereof.

6. The copolymer of claim 1 , wherein the cyclic vinyl ether of the formula (III) comprises:

or a combination thereof.

7. A photoresist composition comprising the copolymer of claim 1 , and a photoacid generator, wherein the photoacid generator is an additive or is incorporated into the copolymer.

8. 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 claim 7 over the one or more layers to be patterned.

9. A method of forming an electronic device, comprising: (a) applying a layer of a photoresist composition of claim 7 on a substrate; (b) patternwise exposing the photoresist composition layer to activating radiation; and (c) developing the exposed photoresist composition layer to provide a resist relief image.

10. The method of claim 9 , wherein the radiation is extreme-ultraviolet or e-beam radiation.