Negative resist composition, method of forming resist pattern, and complex

Patent metadata

Field	Value
Publication number	US-9366960-B2
Application number	US-201414558977-A
Country	US
Kind code	B2
Filing date	Dec 3, 2014
Priority date	Dec 5, 2013
Publication date	Jun 14, 2016
Grant date	Jun 14, 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 including 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 negative resist composition comprising:
a complex represented by the following general formula (1):
[MX n Y 4-n ]  (1)

wherein 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;
a polymerization initiator; and
an organic solvent.

2. A method of forming a resist pattern, comprising: forming a resist film on a substrate using the negative resist composition of claim 1 ; conducting exposure of the resist film; and developing the resist film after the exposure to form a resist pattern.

3. The negative resist composition according to claim 1 , wherein the acid dissociation constant (pKa) of the acid is 2.8 or less.

4. The negative resist composition 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 θ   (2)

wherein, in formula (2), R 1 represents a polymerizable group having a group selected from groups respectively represented by formulae (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.

5. The negative resist composition 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.

6. The negative resist composition 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 θ   (3)

wherein, in formula (3), R 2 represents a polymerizable group having a group selected from groups respectively represented by formulae (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.

7. The negative resist composition 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.

8. The negative resist composition according to claim 1 , wherein M represents hafnium (Hf).

9. The negative resist composition according to claim 1 , wherein M represents zirconium (Zr).

10. The method according to claim 2 , wherein the resist film is exposed with EB or EUV.

Assignees

• Tokyo Ohka Kogyo Co Ltd
• Tokyo Oha Kogyo Co Ltd

Inventors

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

Classifications

• G03F7/038 Primary

  Macromolecular compounds which are rendered insoluble or differentially wettable (G03F7/075 takes precedence; macromolecular azides G03F7/012; macromolecular diazonium compounds G03F7/021) · CPC title

• G03F7/2002

  with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image · CPC title

• C08G18/222

  metal compounds not provided for in groups C08G18/225 - C08G18/26 · 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