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

Patent metadata

Field	Value
Publication number	US-11960206-B2
Application number	US-202218075594-A
Country	US
Kind code	B2
Filing date	Dec 6, 2022
Priority date	Dec 31, 2015
Publication date	Apr 16, 2024
Grant date	Apr 16, 2024

Abstract

A photoresist composition, including an acid-sensitive polymer and photoacid generator compound having Formula (I):

wherein, EWG, Y, R, and M + are the same as described in the specification.

First claim

The invention claimed is:

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.

Assignees

• Rohm & Haas Elect Mat
• Rohm And Hass Electronic Mat Llc

Inventors

• Aqad Emad
• Williams Iii William
• Cameron James F

Classifications

• H10P76/2041

  Photolithographic processes · CPC title

• C07C2603/74

  Adamantanes · CPC title

• C07C2602/08

  the other ring being five-membered, e.g. indane · CPC title

• G03F1/76

  Patterning of masks by imaging · CPC title

• C07C381/12

  Sulfonium compounds · CPC title