Photoresist composition, coated substrate including the photoresist composition, and method of forming electronic device

1. A photoresist composition, comprising:

an acid-sensitive polymer,

a solvent, and

a photoacid generator compound having Formula (II):

wherein:

X 1 , X 2 , X 3 and X −4 are each independently an electron-withdrawing group;

Y is a single bond or linking group;

R is hydrogen; and

M + is an organic cation,

provided that the anion of the photoacid generator compound does not simultaneously include three electron-withdrawing —S(═O) 2 -perfluoroalkyl groups.

2. The photoresist composition of claim 1 , wherein M + is an organic cation having Formula (V):

wherein,

each R 2 is independently a C 1-20 alkyl group, a C 1-20 fluoroalkyl group, a C 3-20 cycloalkyl group, a C 3-20 fluorocycloalkyl group, a C 2-20 alkenyl group, a C 2-20 fluoroalkenyl group, a C 6-20 aryl group, a C 6-20 fluoroaryl group, a C 1-20 heteroaryl group, a C 7-20 aralkyl group, a C 7-20 fluoroaralkyl group, a C 2-20 heteroaralkyl group, or a C 2-20 fluoroheteroaralkyl group, each of which is substituted or unsubstituted,

wherein each R 2 is either separate or connected to the other group R 2 via a single bond or a linking group, and

Ar is a substituted or unsubstituted C 6-30 aromatic organic group.

3. The photoresist composition of claim 1 , wherein M + is an organic cation having Formula (VI):

wherein

X is I or S;

each R 3 is independently a halogen, a C 1-10 alkyl group, a C 1-10 fluoroalkyl group, a C 1-10 alkoxy group, a C 1-10 fluoroalkoxy group, a C 3-10 cycloalkyl group, a C 3-10 fluorocycloalkyl group, a C 3-10 cycloalkoxy group, a C 3-10 fluorocycloalkoxy group, or a C 6-10 alkoxycarbonylalkyleneoxy group;

each n is an integer of 0, 1, 2, 3, 4, and 5; and

m is an integer of 2 or 3, provided that when X is I, m is 2, and where X is S, m is 3.

4. The photoresist composition of claim 1 , wherein M + is an organic cation having Formulae (VII) or (VIII):

wherein

R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 are each independently a halogen, —CN, —OH, a C 1-10 alkyl group, a C 1-10 fluoroalkyl group, a C 1-10 alkoxy group, a C 1-10 fluoroalkoxy group, a C 3-10 cycloalkyl group, a C 3-10 fluorocycloalkyl group, a C 3-10 cycloalkoxy group, or a C 3-10 fluorocycloalkoxy group, each of which except a halogen, —CN, and —OH is substituted or unsubstituted;

J is a single bond or a connecting group selected from S, O, and C═O,

p is each independently an integer of 0, 1, 2, 3, or 4;

r is an integer of 0, 1, 2, 3, 4, and 5, and

s and t are each independently an integer of 0, 1, 2, 3, and 4.

5. A coated substrate, comprising: (a) a substrate having one or more layers to be patterned on a surface thereof, and (b) a layer of the photoresist composition of claim 1 over the one or more layers to be patterned.

6. A method of forming an electronic device, comprising: (a) applying a layer of the photoresist composition of claim 1 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.

7. A photoresist composition, comprising:

an acid-sensitive polymer,

a solvent, and

a photoacid generator compound having Formula (III):

wherein:

X 5 and X 6 are each independently an electron withdrawing group selected from C(CN) 2 , C(NO 2 ) 2 , C(COR 27 ) 2 , C(CO 2 R 28 ) 2 , C(SO 2 R 29 ) 2 , and C(R f ) 2 , wherein R 27 , R 28 , and R 29 are each independently a C 1-30 aliphatic organic group, a C 6-30 aromatic organic group, or a C 1-30 heteroaromatic organic group, and wherein R f is a C 1-30 fluoroalkyl group;

Z 1 and Z 2 are each independently hydrogen, a straight chain C 1-50 alkyl group, a branched C 3-50 alkyl group, a monocyclic or polycyclic C 3-50 cycloalkyl group, a monocyclic or polycyclic C 3-50 heterocycloalkyl group; a monocyclic or polycyclic C 6-50 aryl group, a monocyclic or polycyclic C 3-20 heteroaryl group, or a combination thereof;

Y is a single bond or a linking group;

R is hydrogen; and

M + is an organic cation;

provided that the anion of the photoacid generator compound does not simultaneously include three electron-withdrawing —S(═O) 2 -perfluoroalkyl groups.

8. The photoacid generator compound of claim 7 , wherein in Formula (III):

X 5 and X 6 are each C(CN) 2 ; and

Y is a single bond.

9. The photoresist composition of claim 7 , wherein M + is an organic cation having Formula (V):

wherein,

each R 2 is independently a C 1-20 alkyl group, a C 1-20 fluoroalkyl group, a C 3-20 cycloalkyl group, a C 3-20 fluorocycloalkyl group, a C 2-20 alkenyl group, a C 2-20 fluoroalkenyl group, a C 6-20 aryl group, a C 6-20 fluoroaryl group, a C 1-20 heteroaryl group, a C 7-20 aralkyl group, a C 7-20 fluoroaralkyl group, a C 2-20 heteroaralkyl group, or a C 2-20 fluoroheteroaralkyl group, each of which is substituted or unsubstituted,

wherein each R 2 is either separate or connected to the other group R 2 via a single bond or a linking group, and

Ar is a substituted or unsubstituted C 6-30 aromatic organic group.

10. The photoresist composition of claim 7 , wherein M + is an organic cation having Formula (VI):

wherein

X is I or S;

each R 3 is independently a halogen, a C 1-10 alkyl group, a C 1-10 fluoroalkyl group, a C 1-10 alkoxy group, a C 1-10 fluoroalkoxy group, a C 3-10 cycloalkyl group, a C 3-10 fluorocycloalkyl group, a C 3-10 cycloalkoxy group, a C 3-10 fluorocycloalkoxy group, or a C 6-10 alkoxycarbonylalkyleneoxy group;

each n is an integer of 0, 1, 2, 3, 4, and 5; and

m is an integer of 2 or 3, provided that when X is I, m is 2, and where X is S, m is 3.

11. The photoresist composition of claim 7 , wherein M + is an organic cation having Formulae (VII) or (VIII):

wherein

R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 are each independently a halogen, —CN, —OH, a C 1-10 alkyl group, a C 1-10 fluoroalkyl group, a C 1-10 alkoxy group, a C 1-10 fluoroalkoxy group, a C 3-10 cycloalkyl group, a C 3-10 fluorocycloalkyl group, a C 3-10 cycloalkoxy group, or a C 3-10 fluorocycloalkoxy group, each of which except a halogen, —CN, and —OH is substituted or unsubstituted;

J is a single bond or a connecting group selected from S, O, and C═O,

p is each independently an integer of 0, 1, 2, 3, or 4;

r is an integer of 0, 1, 2, 3, 4, and 5, and

s and t are each independently an integer of 0, 1, 2, 3, and 4.