Compound, photoresist composition comprising same, photoresist pattern comprising same, and method for manufacturing photoresist pattern

Patent metadata

Field	Value
Publication number	US-11680040-B2
Application number	US-201916978557-A
Country	US
Kind code	B2
Filing date	Oct 11, 2019
Priority date	Oct 11, 2018
Publication date	Jun 20, 2023
Grant date	Jun 20, 2023

Abstract

The present specification provides a compound, a photoresist composition comprising the same, a photoresist pattern comprising the same, and a method for preparing a photoresist pattern.

First claim

The invention claimed is:

1. A compound represented by Chemical Formula 1:

wherein, in the Chemical Formula 1,
p is an integer of 2 to 4;
X is S, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group or a substituted or unsubstituted alkyl group, provided that
when p is an integer of 3 or 4, X is not S;
L 1 is the same as or different from each other and each independently is a direct bond, a substituted or unsubstituted alkylene group, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group;
Rb is the same as or different from each other and each independently is a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group;
Q + is the same as or different from each other and each independently is an onium cation;
Y − is the same as or different from each other and each independently is an acid anion; and
m and n are each an integer of 1 to 10.

2. The compound of claim 1 , wherein the compound is represented by any one of Chemical Formulae 2 to 4:

in the Chemical Formulae 2 to 4,
L 1 , Rb, Y − , Q + , m and n are as defined in claim 1 ;
X 1 is S or CR 1 R 2 ;
X 2 is a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group;
X 3 is C or a substituted or unsubstituted alkyl group; and
R 1 and R 2 are the same as or different from each other, and each independently hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted amine group, a substituted or unsubstituted arylphosphine group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or adjacent groups bond to each other to form a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted aliphatic hydrocarbon ring.

3. The compound of claim 2 , wherein X 1 of the Chemical Formula 2 is S or represented by any one of Chemical Formulae 1-1 to 1-3:

in the Chemical Formulae 1-1 to 1-3,
* is a site linked to L 1 ;
R 11 to R 22 are the same as or different from each other, and each independently hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted amine group, a substituted or unsubstituted arylphosphine group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or adjacent groups bond to each other to form a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted aliphatic hydrocarbon ring;
a is an integer of 0 to 2; and
b and c are an integer of 0 to 3.

4. The compound of claim 2 , wherein X 2 of the Chemical Formula 3 is a substituted or unsubstituted phenyl group, or CR 31 , and wherein R 31 is hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

5. The compound of claim 2 , wherein X 3 of the Chemical Formula 4 is C; or a substituted or unsubstituted C 1 to C 10 alkyl group.

6. The compound of claim 1 , wherein Rb is any one of the following structural formulae:

in the structural formulae,

means a site linked to the Chemical Formula 1.

7. The compound of claim 1 , wherein Q + is an onium cation comprising an S, I, O, N, P, Cl, Br, F, As, Se, Sn, Sb, Te, or Bi element.

8. The compound of claim 1 , wherein Q + is represented by Chemical Formula 2-1:

in the Chemical Formula 2-1,
R 41 to R 43 are the same as or different from each other, and each independently hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

9. A photoresist composition comprising:
the compound of claim 1 ;
a binder resin; and
a solvent.

10. The photoresist composition of claim 9 comprising the compound in 1 parts by weight to 10 parts by weight based on 100 parts by weight of the photoresist composition.

11. A photoresist pattern comprising the photoresist composition of claim 9 .

12. A method for preparing a photoresist pattern, the method comprising:
forming a photoresist layer by coating the photoresist composition of claim 9 on a semiconductor substrate;
selectively exposing the photoresist layer; and
developing the exposed photoresist layer.

13. The method for preparing a photoresist pattern of claim 12 , wherein the selectively exposing of the photoresist layer is aligning a mask on the photoresist, and exposing an area of the photoresist layer not covered by the mask to ultraviolet rays.

14. The method for preparing a photoresist pattern of claim 12 , wherein the developing of the exposed photoresist layer is removing the exposed portion in the photoresist layer by immersing in a developing solution.

Assignees

• Lg Chemical Ltd

Inventors

• Park Hyunmin
• Lim Minyoung

Classifications

• G03F7/0045

  with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors · CPC title

• C07C381/12

  Sulfonium compounds · CPC title

• C07C2603/74

  Adamantanes · CPC title

• C07C309/12 Primary

  containing esterified hydroxy groups bound to the carbon skeleton · CPC title

• G03F7/032

  with binders · CPC title