Granted Patent B2

US 12,656,679 · App. 17/749,880 · Granted Jun 16, 2026

Inventors: Li Cui (Westborough, MA); Emad Aqad (Northborough, MA); Yinjie Cen (Shrewsbury, MA); Conner A. Hoelzel (Brookline, MA); James F. Cameron (Brookline, MA); Jong Keun Park (Shrewsbury, MA); Suzanne M. Coley (Mansfield, MA); Choong-Bong Lee (Westborough, MA)

Assignee: DUPONT ELECTRONIC MATERIALS INTERNATIONAL, LLC

G03F7/0045C07C69/78C07C317/22C07C2601/08C07C2601/16

Abstract

Claims (61)

1 . A compound, represented by Formula (1):

wherein,

X is represented by one of Formulae (4) to (9):

wherein, in Formulae (4) to (9),

Ar 2, Ar 3, and Ar 5 are each independently substituted or unsubstituted C 6-30 arylene or substituted or unsubstituted C 3-30 heteroarylene;

wherein Ar 2 in Formula (4) is monocyclic;

Ar 4 is substituted or unsubstituted C 6-30 aryl or substituted or unsubstituted C 3-30 heteroaryl;

R 10 and R 11 are each independently hydrogen, substituted or unsubstituted C 1-30 alkyl, substituted or unsubstituted C 3-30 cycloalkyl, substituted or unsubstituted C 1-30 heterocycloalkyl, substituted or unsubstituted C 6-30 aryl, substituted or unsubstituted C 7-30 arylalkyl, substituted or unsubstituted C 7-30 alkylaryl, substituted or unsubstituted C 6-30 aryloxy, substituted or unsubstituted C 3-30 heteroaryl, substituted or unsubstituted C 4-30 alkylheteroaryl, substituted or unsubstituted C 4-30 heteroarylalkyl, or substituted or unsubstituted C 3-30 heteroaryloxy, and

*, * ′ and *″ each indicates a point of attachment to a respective adjacent oxygen atom;

each L 1 is independently a single bond or a divalent linking group;

each L 2 is a single bond or a linking group;

each Ar 1 is independently substituted or unsubstituted C 6-30 arylene or substituted or unsubstituted C 3-30 heteroarylene, wherein the substituted C 6-30 arylene and the substituted C 3-30 heteroarylene are each independently substituted with at least one of halogen, C 1-30 alkyl, C 1-30 alkoxy, C 4-30 cycloalkyl, C 3-30 heterocycloalkyl, C 2-30 alkenyl, C 2-30 alkynyl, C 6-30 aryl, C 7-30 arylalkyl, C 7-30 alkylaryl, C 6-30 aryloxy, C 3-30 heteroaryl, C 4-30 alkylheteroaryl, C 4-30 heteroarylalkyl, or C 3-30 heteroaryloxy;

each R 1 is independently an organic group comprising an acid-labile group;

R 2 and R 3 are each independently hydrogen, or substituted or unsubstituted C 1-30 alkyl;

R 2 and R 3 together optionally form a ring via a single bond or a divalent linking group,

wherein the ring is substituted or unsubstituted;

m is an integer greater than or equal to 1;

k is an integer from 1 to 5;

r is 2 or 3, and

wherein the compound is non-polymeric,

wherein R 1 has a structure represented by one of Formula (2a) or Formula (2b):

wherein, in Formulae (2a) and (2b),

R 4 to R 6 are each independently hydrogen, substituted or unsubstituted C 1-20 alkyl, substituted or unsubstituted C 3-20 cycloalkyl, substituted or unsubstituted C 3-20 heterocycloalkyl, substituted or unsubstituted C 2-20 alkenyl, substituted or unsubstituted C 3-20 cycloalkenyl, substituted or unsubstituted C 3-20 heterocycloalkenyl, substituted or unsubstituted C 6-20 aryl, or substituted or unsubstituted C 2-20 heteroaryl, provided that no more than one selected from R 4 to R 6 is hydrogen, and provided that if one of R 4 to R 6 is hydrogen, then at least one of the others from R 4 to R 6 substituted or unsubstituted C 6-20 aryl or substituted or unsubstituted C 3-20 heteroaryl,

each of R 4 to R 6 may optionally further include a divalent linking group as part of its structure,

R 7 and R 8 are each independently hydrogen, substituted or unsubstituted C 1-20 alkyl, substituted or unsubstituted C 3-20 cycloalkyl, substituted or unsubstituted C 3-20 heterocycloalkyl, substituted or unsubstituted C 6-20 aryl, or substituted or unsubstituted C 2-20 heteroaryl,

each of R 7 and R 8 may optionally further include a divalent linking group as part of its structure,

R 9 is substituted or unsubstituted C 1-20 alkyl, substituted or unsubstituted C 3-20 cycloalkyl, substituted or unsubstituted C 3-20 heterocycloalkyl, substituted or unsubstituted C 6-20 aryl, or substituted or unsubstituted C 3-20 heteroaryl,

R 9 optionally may further comprise a divalent linking group as part of its structure,

any two of R 4 to R 6 together optionally may form a ring via a single bond or a divalent linking group, wherein the ring is substituted or unsubstituted,

R 7 and R 8 together optionally may form a ring via a single bond or a divalent linking group, wherein the ring is substituted or unsubstituted,

any one or more of R 7 or R 8 together with Ro optionally may form a ring via a single bond or a divalent linking group, wherein the ring is substituted or unsubstituted, and

* and *′ each indicate a binding site to L 1 .

2 . The compound of claim 1 , wherein R 1 comprises an ester group.

3 . The compound of claim 1 , wherein R 1 comprises an acetal or a ketal group.

4 . The compound of claim 1 , wherein the compound comprises one or more iodine atoms.

5 . The compound of claim 1 , wherein each subunit represented by the integer r is the same.

6 . A photoresist composition, comprising:

the compound of claim 1 ; and

a solvent.

7 . 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 6 disposed over the one or more layers to be patterned.

8 . The photoresist composition of claim 6 , further comprising a polymer.

9 . The photoresist composition of claim 8 , wherein the polymer is acid-sensitive.

10 . The photoresist composition of claim 6 , further comprising a photoacid generator.

11 . A method for forming a pattern, the method comprising:

applying a layer of the photoresist composition of claim 6 on a substrate to provide a photoresist layer;

pattern-wise exposing the photoresist layer to activating radiation to provide an exposed photoresist layer; and

developing the exposed photoresist layer to provide a photoresist pattern.

12 . A method for forming a pattern, the method comprising:

applying a layer of the photoresist composition of claim 6 on a substrate to provide a photoresist composition layer;

pattern-wise exposing the photoresist composition layer to activating radiation to provide an exposed photoresist composition layer; and

developing the exposed photoresist composition layer to provide a photoresist pattern.

13 . The coated substrate of claim 7 , wherein R 1 comprises an ester group.

14 . The coated substrate of claim 7 , wherein R 1 comprises an acetal or a ketal group.

15 . The coated substrate of claim 7 , wherein the compound comprises one or more iodine atoms.

16 . The coated substrate of claim 7 , wherein each subunit represented by the integer r is the same.

17 . The compound of claim 1 , wherein X is represented by Formula (5).

18 . The compound of claim 1 , wherein X is represented by Formula (6).

19 . The compound of claim 1 , wherein X is represented by Formula (9).

20 . The compound of claim 1 , wherein X is represented by Formula (7) or (8).

Assignments (4)

Continuity (1)

References Cited (24)