Photosensitizing compound, photoresist composition including the same, and method of manufacturing integrated circuit device

Patent metadata

Field	Value
Publication number	US-12429768-B2
Application number	US-202217741753-A
Country	US
Kind code	B2
Filing date	May 11, 2022
Priority date	Aug 27, 2021
Publication date	Sep 30, 2025
Grant date	Sep 30, 2025

Abstract

A compound represented by Chemical Formula 1:

Ar 1 -L 1 -Ar 2 -L 2 -X—R 1 ,  [Chemical Formula 1]

in which Ar 1 and Ar 2 are aromatic rings or heterocyclic aromatic rings that each include at least one iodine atom and Ar 1 also includes at least one hydroxyl group, L 1 and L 2 are each a divalent linking group, X is —C(═O)O— or —S(═O) 2 —O—, and R 1 is an acid-labile protecting group. Photoresist compositions that include the compound, and methods of manufacturing an integrated circuit device by using the photoresist composition.

First claim

What is claimed is:

1. A compound comprising Chemical Formula 1:
Ar 1 -L 1 -Ar 2 -L 2 -X—R 1   [Chemical Formula 1]

wherein, in Chemical Formula 1,
Ar 1 is an organic group including:
a C6 to C30 aromatic ring, which includes at least one iodine atom and at least one hydroxyl group, or
a C6 to C30 heterocyclic aromatic ring, which includes at least one iodine atom and at least one hydroxyl group,

Ar 2 is an organic group including:
a C6 to C30 aromatic ring, which includes at least one iodine atom, or
a C6 to C30 heterocyclic aromatic ring, which includes at least one iodine atom,

L 1 and L 2 are each independently a divalent linking group, the divalent linking group including —O—, —S—, —SO—, —SO 2 —, —CO—, —O—CO—O—, —C(═O)O—, —OCO—, —CONH—, —NHCO—, —CO—, a substituted or unsubstituted C1 to C6 linear alkylene group, a substituted or unsubstituted C3 to C6 branched alkylene group, a substituted or unsubstituted C3 to C15 cycloalkylene group, a substituted or unsubstituted C2 to C6 alkenylene group, or a combination thereof,
X is —C(═O)O— or —S(═O) 2 —O—, and
R 1 is an acid-labile protecting group including a substituted t-butyl group or a substituted or unsubstituted C3 to C30 tertiary alicyclic group.

2. The compound as claimed in claim 1 , wherein:
the compound comprises Chemical Formula 2:

in Chemical Formula 2, R 1 is defined the same as R 1 that of Chemical Formula 1.

3. The compound as claimed in claim 1 , wherein, in Chemical Formula 1, R 1 is a substituted or unsubstituted C3 to C30 tertiary alicyclic group.

4. The compound as claimed in claim 1 , wherein:
a number of iodine atoms included in the compound of Chemical Formula 1 is at least 4, and
a total weight of the iodine atoms in the compound is at least 50 wt % based on a total weight of the compound.

5. The compound as claimed in claim 1 , wherein:
L 1 is —O—, and
L 2 is —C(═O)O—.

6. The compound as claimed in claim 1 , wherein the compound is a compound selected from the group consisting of Chemical Formula 2A, 2B, 2C, 2D, and 2E:

7. A photoresist composition comprising the compound as claimed in claim 1 .

8. A photoresist composition, comprising:
a compound;
a chemically amplified polymer;
a photoacid generator (PAG); and
a solvent,
wherein the compound comprises Chemical Formula 1:
Ar 1 -L 1 -Ar 2 -L 2 -X—R 1   [Chemical Formula 1]

wherein, in Chemical Formula 1,
Ar 1 is an organic group including:
a C6 to C30 aromatic ring, which includes at least one iodine atom and at least one hydroxyl group, or
a C6 to C30 heterocyclic aromatic ring, which includes at least one iodine atom and at least one hydroxyl group,

Ar 2 is an organic group including:
a C6 to C30 aromatic ring, which includes at least one iodine atom, or
a C6 to C30 heterocyclic aromatic ring, which includes at least one iodine atom,

L 1 and L 2 are each independently a divalent linking group, the divalent linking group including —O—, —S—, —SO—, —SO 2 —, —CO—, —O—CO—O—, —C(═O)O—, —OCO—, —CONH—, —NHCO—, —CO—, a substituted or unsubstituted C 1 to C 6 linear alkylene group, a substituted or unsubstituted C 3 to C 6 branched alkylene group, a substituted or unsubstituted C 3 to C15 cycloalkylene group, a substituted or unsubstituted C 2 to C 6 alkenylene group, or a combination thereof,
X is —C(═O)O— or —S(═O) 2 —O—, and
R 1 is an acid-labile protecting group including a substituted or unsubstituted t-butyl group or a substituted or unsubstituted C3 to C30 tertiary alicyclic group.

9. The photoresist composition as claimed in claim 8 , wherein:
the compound comprises Chemical Formula 2:

in Chemical Formula 2, R 1 is defined the same as R 1 that of Chemical Formula 1.

10. The photoresist composition as claimed in claim 8 , wherein, in Chemical Formula 1, R 1 is a substituted or unsubstituted C3 to C30 tertiary alicyclic group.

11. The photoresist composition as claimed in claim 8 , wherein the compound includes at least four iodine atoms.

12. The photoresist composition as claimed in claim 8 , wherein, in Chemical Formula 1:
L 1 is —O—, and
L 2 is —C(═O)O—.

13. The photoresist composition as claimed in claim 8 , wherein the compound is a compound selected from the group consisting of Chemical Formula 2A and 2B:

14. The photoresist composition as claimed in claim 8 , wherein the compound comprises Chemical Formula 2C:

15. The photoresist composition as claimed in claim 8 , wherein the compound comprises Chemical Formula 2D:

16. The photoresist composition as claimed in claim 8 , wherein the compound comprises Chemical Formula 2E:

17. A method of manufacturing an integrated circuit device, the method comprising:
forming a photoresist layer on an underlayer by using a photoresist composition including a compound, a chemically amplified polymer, a photoacid generator (PAG), and a solvent, the compound including a phenolic hydroxyl group, a plurality of iodine atoms, and an acid-labile protecting group;
generating a plurality of acids from the phenolic hydroxyl group and the PAG in a first region of the photoresist layer by exposing the first region, and deprotecting the chemically amplified polymer and the compound by the plurality of acids;
forming a photoresist pattern including an unexposed region of the photoresist layer by removing the exposed first region of the photoresist layer by using a developer; and
processing the underlayer by using the photoresist pattern.

18. The method as claimed in claim 17 , wherein:
the compound comprises Chemical Formula 1:
Ar 1 -L 1 -Ar 2 -L 2 -X—R 1   [Chemical Formula 1]

in Chemical Formula 1,
Ar 1 is an organic group including:
a C6 to C30 aromatic ring, which includes at least one iodine atom and at least one hydroxyl group, or
a C6 to C30 heterocyclic aromatic ring, which includes at least one iodine atom and at least one hydroxyl group,

Ar 2 is an organic group including:
a C6 to C30 aromatic ring, which includes at least one iodine atom, or
a C6 to C30 heterocyclic aromatic ring, which includes at least one iodine atom,

L 1 and L 2 are each independently a divalent linking group, the divalent linking group including —O—, —S—, —SO—, —SO 2 —, —CO—, —O—CO—O—, —C(═O)O—, —OCO—, —CONH—, —NHCO—, —CO—, a substituted or unsubstituted C1 to C6 linear alkylene group, a substituted or unsubstituted C3 to C6 branched alkylene group, a substituted or unsubstituted C3 to C15 cycloalkylene group, a substituted or unsubstituted C2 to C6 alkenylene group, or a combination thereof,
X is —C(═O)O— or —S(═O) 2 —O—, and
R 1 is an acid-labile protecting group including a substituted or unsubstituted t-butyl group or a substituted or unsubstituted C3 to C30 tertiary alicyclic group.

19. The method as claimed in claim 17 , wherein:
the c

Assignees

• Samsung Electronics Co Ltd

Inventors

• Song Hyun-Ji

Classifications

• C07C2601/08

  the ring being saturated · CPC title

• C07C2601/14

  The ring being saturated · CPC title

• C07C2603/74

  Adamantanes · CPC title

• C07C69/736 Primary

  the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring · CPC title

• G03F7/30

  Imagewise removal using liquid means · CPC title