Photoacid generator, photoresist, coated substrate, and method of forming an electronic device

1. A compound having the formula (I):

wherein

each R 1 is independently H or a substituted or unsubstituted C 1-30 aliphatic group optionally bonded to an adjacent R 1 ,

each R 2 and R 3 is independently H, F, C 1-10 alkyl, C 1-10 fluoroalkyl, C 3-10 cycloalkyl or C 3-10 fluorocycloalkyl, wherein at least one R 2 and/or R 3 contains F,

L 1 , L 2 and L 3 are each independently a single bond, or a C 1-20 linking group optionally comprising a lactone group, wherein one or more of L 1 , L 2 and L 3 optionally form a ring structure wherein all structures

 form a fused acetal- or ketal-containing ring with the ring structure formed by one or more of L 1 , L 2 and L 3 , and wherein one or more of L 1 , L 2 and L 3 is optionally substituted with a polymerizable C 2-20 alpha-beta unsaturated organic group,

X is an ether, ester, carbonate, amine, amide, urea, sulfate, sulfonate, or sulfonamide-containing group,

Z + is an organic or inorganic cation, and

each a is independently an integer of 1 to 12, b is an integer of 1 to 5, each c is 1, d and r are each independently 0 or 1, and p is an integer of from 0 to 10, and q is an integer of from 1 to 10.

2. The compound of claim 1 , wherein Z + is a cation of the formula (V):

wherein each R 5 is independently substituted or unsubstituted C 1-20 alkyl, C 1-20 fluoroalkyl, C 3-20 cycloalkyl, C 3-20 fluorocycloalkyl, C 2-20 alkenyl, C 2-20 fluoroalkenyl, C 6-20 aryl, C 6-20 fluoroaryl, C 5-20 heteroaryl, C 7-20 aralkyl, C 7-20 fluoroaralkyl, C 6-20 heteroaralkyl, where each R 5 is separate or connected to the other group R 5 , and Ar is a C 5-30 aromatic-containing group.

3. The compound of claim 2 , wherein the cation is of the formulas (VI), (VII), or (VIII):

wherein

each R 5 is independently substituted or unsubstituted C 1-20 alkyl, C 1-20 fluoroalkyl, C 3-20 cycloalkyl, C 3-20 fluorocycloalkyl, C 2-20 alkenyl, C 2-20 fluoroalkenyl, C 6-20 aryl, C 6-20 fluoroaryl, C 5-20 heteroaryl, C 7-20 aralkyl, C 7-20 fluoroaralkyl, or C 6-20 heteroaralkyl, wherein each R 5 is separate or connected to the other R 5 ;

R 6 , R 7 , R 8 and R 9 are each independently H, a halogen, C 1-20 alkyl, C 1-20 fluoroalkyl, C 1-20 alkoxy, C 1-20 fluoroalkoxy, C 1-20 thioalkoxy, C 1-20 fluorothioalkoxy, C 1-20 alkoxycarbonyl, C 1-20 fluoroalkoxycarbonyl, C 1-20 thioalkoxycarbonyl, C 1-20 fluorothioalkoxycarbonyl, C 3-20 cycloalkyl, C 3-20 fluorocycloalkyl, C 3-20 cycloalkoxy, C 3-20 fluorocycloalkoxy, C 2-20 alkenyl, C 2-20 fluoroalkenyl, C 6-20 aryl, C 6-20 fluoroaryl, C 6-20 aryloxy, C 6-20 fluoroaryloxy, C 5-20 heteroaryl, C 5 - 20 heteroaryloxy, C 7-20 aralkyl, C 7-20 fluoroaralkyl, C 7-20 aralkyloxy C 7-20 fluoroaralkyloxy, or C 6-20 heteroaralkyl, or C 6-20 heteroaralkyloxy, wherein R 6 , R 7 , R 8 and R 9 are each independently unsubstituted or further substituted to include an acid-labile group, a base-labile group, or a base-soluble group, and

m is an integer of 1 to 5, n is an integer of 0 to 3, s is an integer of 0 to 4, t is an integer of 0 to 4, and e is an integer of 0 to 4.

4. The compound of claim 1 , wherein Z + is of the formula (IX), (X), (XI), or (XII):

wherein

R 10 , R 11 , R 12 and R 14 are independently H, a halogen, C 1-10 alkyl, C 1-10 fluoroalkyl, C 1-10 alkoxy, C 1-10 fluoroalkoxy, C 3-10 cycloalkyl, C 3-10 fluorocycloalkyl, C 3-10 cycloalkoxy, or C 3-10 fluorocycloalkoxy,

R 13 is H, C 1-10 alkyl, C 1-10 fluoroalkyl, C 3-10 cycloalkyl, or C 3-10 fluorocycloalkyl, and

e and f are each independently 1 or 2.

5. A photoresist composition, comprising:

an acid-sensitive polymer, and

a compound of claim 1 .

6. 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 5 over the one or more layers to be patterned.

7. A method of forming an electronic device, comprising: (a) applying a layer of a photoresist composition of claim 5 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.

8. The method of claim 7 , wherein the radiation is 193 nm or 248 nm radiation.

9. A compound having the formula (II):

wherein

each R 1 is independently H or a substituted or unsubstituted C 1-30 aliphatic group that may be bonded to an adjacent R 1 ,

each R 2 and R 3 is independently H, F, C 1-10 alkyl, C 1-10 fluoroalkyl, C 3-10 cycloalkyl or C 3-10 fluorocycloalkyl, wherein at least one R 2 and/or R 3 contains F,

L 1 , L 2 and L 3 are each independently a single bond, or a C 1-20 linking group that may comprise a lactone group, wherein one or more of L 1 , L 2 and L 3 may form a ring structure, and wherein one or more of L 1 , L 2 and L 3 may be substituted with a polymerizable C 2-20 alpha-beta unsaturated organic group,

X 1 is O,

Z + is an organic or inorganic cation,

each c, d, and r is independently 0 or 1,

p is an integer of from 0 to 10, and

q is an integer of from 1 to 10.

10. A compound having the formulas (II-a) to (II-c):

wherein

each R 1 is independently H or a substituted or unsubstituted C 1-30 aliphatic group that may be bonded to an adjacent R 1 ,

each R 2 and R 3 is independently H, F, C 1-10 alkyl, C 1-10 fluoroalkyl, C 3-10 cycloalkyl or C 3-10 fluorocycloalkyl, wherein at least one R 2 and/or R 3 contains F,

X 1 is O,

Z + is an organic or inorganic cation,

p is an integer of from 0 to 10,

q is an integer of from 1 to 10,

r is independently 0 or 1, and

R 4 in formula (II-c) is H, C 1-10 alkyl, or C 3-10 cycloalkyl.

11. A compound having the formula (III):

wherein

each R 1 is independently H or a substituted or unsubstituted C 1-30 aliphatic group that may be bonded to an adjacent R 1 ,

each R 2 and R 3 is independently H, F, C 1-10 alkyl, C 1-10 fluoroalkyl, C 3-10 cycloalkyl or C 3-10 fluorocycloalkyl, wherein at least one R 2 and/or R 3 contains F,

X 1 is O,

L 4 is a C 1-20 lactone-containing linking group,

Z + is an organic or inorganic cation,

a is independently an integer of 1 to 12,

p is an integer of from 0 to 10,

q is an integer of from 1 to 10, and

r is independently 0 or 1.

12. A compound having the formula (III-a) or (III-b):

wherein

each R 1 is independently H or a substituted or unsubstituted C 1-30 aliphatic group that may be bonded to an adjacent R 1 ,

each R 2 and R 3 is independently H, F, C 1-10 alkyl, C 1-10 fluoroalkyl, C 3-10 cycloalkyl or C 3-10 fluorocycloalkyl, wherein at least one R 2 and/or R 3 contains F,

L 5 and L 6 are independently a single bond or a C 1-10 linking group,

X is an ether, ester, carbonate, amine, amide, urea, sulfate, sulfonate, or sulfonamide-containing group,

X 1 and X 2 are independently O or NR where R is H or a C 1-6 alkyl,

p is an integer of from 0 to 10,

q is an integer of from 1 to 10,

r is independently 0 or 1,

and u is 0 or 1.