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 (I):

wherein:

each EWG is independently chosen from —CN, —NO 2 , —C(═O)R 21 , —C(═O)OR 22 , or —SO 2 R 23 , wherein R 21 , R 22 , or R 23 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;

Y is a single bond or a linking group;

R is hydrogen, a straight chain or branched C 1-20 alkyl group, a straight chain or branched C 2-20 alkenyl group, a monocyclic or polycyclic C 3-20 cycloalkyl group, a monocyclic or polycyclic C 3-20 cycloalkenyl group, a monocyclic or polycyclic C 3-20 heterocycloalkyl group; a monocyclic or polycyclic C 3-20 heterocycloalkenyl group; a monocyclic or polycyclic C 6-20 aryl group, or a monocyclic or polycyclic C 1-20 heteroaryl group, each of which except hydrogen is substituted or unsubstituted, wherein when R comprises a polymerizable group, the photoacid generator is a polymerized unit of the acid-sensitive polymer; and

M + is an organic cation.

2. 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(NO 2 ) 2 , C(COR 21 ) 2 , C(CO 2 R 22 ) 2 , C(SO 2 R 23 ) 2 , and C(R f ) 2 , wherein R 21 , R 22 , and R 23 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 -C 30 fluoroalkyl group;

Z 1 and Z 2 are each independently hydrogen, a straight chain or branched C 1-50 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 5-20 heteroaryl group, or a combination thereof, wherein groups Z 1 and Z 2 are optionally connected to each other to form a ring;

Y is a single bond or a linking group;

R is a straight chain or branched C 1-20 alkyl group, a straight chain or branched C 2-20 alkenyl group, a monocyclic or polycyclic C 3-20 cycloalkyl group, a monocyclic or polycyclic C 3-20 cycloalkenyl group, a monocyclic or polycyclic C 3-20 heterocycloalkyl group; a monocyclic or polycyclic C 3-20 heterocycloalkenyl group; a monocyclic or polycyclic C 6-20 aryl group, or a monocyclic or polycyclic C 1-20 heteroaryl group, each of which is substituted or unsubstituted, and

M + is an organic cation.

3. A photoresist composition, comprising:

an acid-sensitive polymer,

a solvent, and

a photoacid generator compound having Formula (III):

wherein in Formula (III):

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

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 C 3-50 cycloalkyl group, a polycyclic C 7-50 cycloalkyl group, a monocyclic or polycyclic C 3-50 heterocycloalkyl group; a monocyclic C 6-50 aryl group, a polycyclic C 10-50 aryl group, a monocyclic or polycyclic C 5-20 heteroaryl group, or a combination thereof;

R is a straight chain or branched C 1-20 alkyl group, a straight chain or branched C 2-20 alkenyl group, a monocyclic or polycyclic C 3-20 cycloalkyl group, a monocyclic or polycyclic C 3-20 cycloalkenyl group, a monocyclic or polycyclic C 3-20 heterocycloalkyl group; a monocyclic or polycyclic C 3-20 heterocycloalkenyl group; a monocyclic or polycyclic C 6-20 aryl group, or a monocyclic or polycyclic C 1-20 heteroaryl group, each of which is substituted or unsubstituted;

Y is a single bond or a linking group; and

M + is an organic cation.

4. The photoresist composition of claim 2 , wherein in Formula (III):

Y is a single bond.

5. A photoresist composition comprising:

an acid-sensitive polymer,

a solvent, and

a photoacid generator compound having Formula (IV):

wherein,

X 5 and X 6 are each independently an electron withdrawing group selected from 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 -C 30 fluoroalkyl group;

M + is an organic cation;

R 1 is 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 an electron-withdrawing group selected from NO 2 , CN, C(R f ) 3 or CO 2 R, wherein R f is a C 1 -C 30 fluoroalkyl group; and

k is an integer of 0, 1, 2, 3, or 4.

6. 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.

7. 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.

8. 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.

9. The photoresist composition of claim 1 , wherein R comprises a polymerizable group, and wherein the photoacid generator is a polymerized unit of the acid-sensitive polymer.

10. 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.

11. 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.

12. A photoresist composition comprising:

an acid-sensitive polymer,

a solvent, and

a photoacid generator compound having Formulae (IIa) or (IIb):

wherein:

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

Y is a single bond or a linking group;

R is hydrogen, a straight chain or branched C 1-20 alkyl group, a straight chain or branched C 2-20 alkenyl group, a monocyclic or polycyclic C 3-20 cycloalkyl group, a monocyclic or polycyclic C 3-20 cycloalkenyl group, a monocyclic or polycyclic C 3-20 heterocycloalkyl group; a monocyclic or polycyclic C 3-20 heterocycloalkenyl group; a monocyclic or polycyclic C 3-20 aryl group, or a monocyclic or polycyclic C 1-20 heteroaryl group, each of which except hydrogen is substituted or unsubstituted; and

M is an organic cation.

13. The photoresist composition of claim 12 , wherein the photoacid generator compound having Formula (II) does not contain a halogen atom.

14. The photoresist composition of claim 12 , wherein the electron-withdrawing group does not contain fluorine.

15. A photoresist composition comprising:

an acid-sensitive polymer,

a solvent, and

a photoacid generator compound represented by:

wherein M is an organic cation.

16. The photoresist composition of claim 1 , wherein the photoacid generator compound having Formula (I) does not contain a halogen atom.

17. The photoresist composition of claim 1 , wherein the electron-withdrawing group does not contain fluorine.

18. The photoresist composition of claim 2 , wherein the photoacid generator compound having Formula (III) does not contain a halogen atom.

19. The photoresist composition of claim 2 , wherein the electron-withdrawing group does not contain fluorine.

20. The photoresist composition of claim 5 , wherein the photoacid generator compound having Formula (IV) does not contain a halogen atom.

21. The photoresist composition of claim 5 , wherein the electron-withdrawing group does not contain fluorine.