Negative resist composition, method of forming resist pattern and complex

Patent metadata

Field	Value
Publication number	US-9499646-B2
Application number	US-201615153044-A
Country	US
Kind code	B2
Filing date	May 12, 2016
Priority date	Dec 5, 2013
Publication date	Nov 22, 2016
Grant date	Nov 22, 2016

Abstract

A negative resist composition including a complex represented by the general formula (1); and a polymerization initiator, in which M represents hafnium (Hf) or zirconium (Zr), X represents a ligand comprising a conjugate base of an acid which has an acid dissociation constant (pKa) of 3.8 or less and has a polymerizable group, Y represents a ligand having no polymerizable group, and n represents an integer of 1 to 4.

[MX n Y 4-n ]  (1)

First claim

What is claimed is:

1. A complex which is represented by the following general formula (1):
[MX n Y 4-n ]  (1)

wherein M represents hafnium or zirconium, X represents a ligand comprising a conjugate base of an acid which has an acid dissociation constant pKa of 3.8 or less and has a polymerizable group, Y represents a ligand having no polymerizable group, and n represents an integer of 1 to 4.

2. The complex according to claim 1 , wherein the acid dissociation constant pKa of the acid is 2.8 or less.

3. The complex according to claim 1 , wherein X in the formula (1) is a ligand comprising a conjugate base represented by general formula (2) shown below:
R 1 —Y 1 —SO 3 ⊖   (2)

wherein R 1 represents a polymerizable group having a group selected from groups (X-01) to (X-07) shown below, and Y 1 represents a divalent linking group or a single bond;

wherein R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms, Ar represents an aromatic hydrocarbon group, n represents an integer of 0 to 2, and * represents a valence bond.

4. The complex according to claim 1 , wherein X in the formula (1) is a ligand comprising a conjugate base selected from the group consisting of a conjugate base of 3-(methacryloyloxy)-1-propanesulfonic acid, a conjugate base of 3-(acryloyloxy)-1-propanesulfonic acid, a conjugated base of vinylsulfonic acid, and a conjugated base of styrenesulfonic acid.

5. The complex according to claim 1 , wherein X in the formula (1) is a ligand comprising a conjugate base represented by general formula (3) shown below:
R 2 —Y 2 —COO ⊖   (3)

wherein, in formula (3), R 2 represents a polymerizable group having a group selected from (X-01) to (X-07) shown below, and Y 2 represents a divalent linking group or a single bond:

wherein R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms, Ar represents an aromatic hydrocarbon group, n represents an integer of 0 to 2, and * represents a valence bond.

6. The complex according to claim 1 , wherein X in the formula (1) is a ligand comprising a conjugate base selected from the group consisting of a conjugate base of carboxymethyl methacrylate, and a conjugate base of carboxymethyl acrylate.

7. The complex according to claim 1 , wherein M represents hafnium.

8. The complex according to claim 2 , wherein M represents hafnium.

9. The complex according to claim 3 , wherein M represents hafnium.

10. The complex according to claim 4 , wherein M represents hafnium.

11. The complex according to claim 5 , wherein M represents hafnium.

12. The complex according to claim 6 , wherein M represents hafnium.

13. The complex according to claim 1 , wherein M represents zirconium.

14. The complex according to claim 2 , wherein M represents zirconium.

15. The complex according to claim 3 , wherein M represents zirconium.

16. The complex according to claim 4 , wherein M represents zirconium.

17. The complex according to claim 5 , wherein M represents zirconium.

18. The complex according to claim 6 , wherein M represents zirconium.

19. The complex according to claim 4 , wherein X in the formula (1) is a ligand comprising a conjugate base of 3-(methacryloyloxy)-1-propanesulfonic acid, and M represents hafnium.

20. The complex according to claim 6 , wherein X in the formula (1) is a ligand comprising a conjugate base of carboxymethyl methacrylate, and M represents hafnium.

Assignees

• Tokyo Ohka Kogyo Co Ltd

Inventors

• Yamashita Naoki
• Komuro Yoshitaka
• Utsumi Yoshiyuki
• Shiono Daiju

Classifications

• G03F7/004

  Photosensitive materials (G03F7/12, G03F7/14 take precedence) · CPC title

• C08F299/0464

  Metals or metal containing compounds · CPC title

• C08F4/06

  Metallic compounds other than hydrides and other than metallo-organic compounds; Boron halide or aluminium halide complexes with organic compounds containing oxygen · CPC title

• C08F4/16

  of silicon, germanium, tin, lead, titanium, zirconium or hafnium · CPC title

• C08F30/04 Primary

  containing a metal · CPC title