Resist material

Patent metadata

Field	Value
Publication number	US-11487204-B2
Application number	US-201816630517-A
Country	US
Kind code	B2
Filing date	Jul 3, 2018
Priority date	Jul 27, 2017
Publication date	Nov 1, 2022
Grant date	Nov 1, 2022

Abstract

To provide a resist material that can form a film with high smoothness and uniformity and has high patterning performance, such as resolution, a resist material is provided that contains a calixarene compound (A) with a molecular structure represented by the following structural formula (1) and a resin component (B);wherein R1 denotes a perfluoroalkyl group or a structural moiety with a perfluoroalkyl group; R2 denotes a hydrogen atom, a polar group, a polymerizable group, or a structural moiety with a polar group or a polymerizable group; R3 denotes a hydrogen atom, an aliphatic hydrocarbon group that optionally has a substituent, or an aryl group that optionally has a substituent; n denotes an integer in the range of 2 to 10; and * denotes a bonding point with an aromatic ring.

First claim

The invention claimed is:

1. A resist material comprising: a calixarene compound (A) with a molecular structure represented by the following structural formula (1-1) or (1-2); and a resin component (B):

wherein R 1 denotes a perfluoroalkyl group or a structural moiety with a perfluoroalkyl group represented by —X—R F , wherein R F denotes the perfluoroalkyl group and X is an alkylene group that optionally has a substituent, a (poly)alkylene ether structure, a (poly)alkylene thioether structure, a (poly)ester structure, a (poly)urethane structure, or a structural moiety composed thereof;
R 2 denotes a hydrogen atom, a polar group selected from a hydroxy group, an amino group, a carboxy group, a thiol group, a phosphate group, and an alkoxysilyl group, a polymerizable group selected from a vinyl group, a vinyloxy group, an ethynyl group, an ethynyloxy group, a (meth)acryloyl group, a (meth)acryloyloxy group, a (2-methyl)glycidyl group, a (2-methyl)glycidyloxy group, a 3-alkyloxetanylmethyl group, and a 3-alkyloxetanylmethyloxy group, or a structural moiety with the polar group or the polymerizable group; and
R 3 denotes a hydrogen atom, an aliphatic hydrocarbon group that optionally has a substituent, or an aryl group that optionally has a substituent; n denotes an integer in the range of 2 to 10.

2. The resist material according to claim 1 , wherein the resin component (B) contains as an essential component an active energy beam curing compound (B1), a resin with a novolak phenolic hydroxy group or a modified product thereof (B2), a calixarene compound other than the calixarene compound (A) or a modified product thereof (B3), a (poly)hydroxystyrene resin (B4), or another resin with a phenolic hydroxy group or a modified product thereof (B5).

3. The resist material according to claim 1 , wherein R 2 denotes the structural moiety with the polar group represented by one of the following structural formulae (3-1) to (3-7),

wherein R 4 independently denotes an alkylene group having 1 to 6 carbon atoms, and R 5 denotes an alkyl group having 1 to 3 carbon atoms.

4. The resist material according to claim 1 , wherein X is a (poly)alkylene ether chain or a (poly)alkylene thioether chain.

5. The resist material according to claim 4 , wherein X has an alkylene group having 1 to 6 carbon atoms.

6. The resist material according to claim 1 , wherein n is 4, 6, or 8.

7. The resist material according to claim 2 , wherein R 2 denotes the structural moiety with the polar group represented by one of the following structural formulae (3-1) to (3-7),

wherein R 4 independently denotes an alkylene group having 1 to 6 carbon atoms, and R 5 denotes an alkyl group having 1 to 3 carbon atoms.

8. The resist material according to claim 2 , wherein X is a (poly)alkylene ether chain or a (poly)alkylene thioether chain.

9. The resist material according to claim 8 , wherein X has an alkylene group having 1 to 6 carbon atoms.

10. The resist material according to claim 2 , wherein n is 4, 6, or 8.

11. The resist material according to claim 1 , wherein R 2 denotes a polymerizable group selected from a vinyl group, a vinyloxy group, an ethynyl group, an ethynyloxy group, a (meth)acryloyl group, a (meth)acryloyloxy group, a (2-methyl)glycidyl group, a (2-methyl)glycidyloxy group, a 3-alkyloxetanylmethyl group, and a 3-alkyloxetanylmethyloxy group, or a structural moiety with the polymerizable group.

12. The resist material according to claim 2 , wherein R 2 denotes a polymerizable group selected from a vinyl group, a vinyloxy group, an ethynyl group, an ethynyloxy group, a (meth)acryloyl group, a (meth)acryloyloxy group, a (2-methyl)glycidyl group, a (2-methyl)glycidyloxy group, a 3-alkyloxetanylmethyl group, and a 3-alkyloxetanylmethyloxy group, or a structural moiety with the polymerizable group.

Assignees

• Dainippon Ink & Chemicals

Inventors

• Imada Tomoyuki
• Yamamoto Shinya
• Miyamoto Masanori

Classifications

• C07C323/16

  the carbon skeleton containing six-membered aromatic rings · CPC title

• G03F7/0226

  characterised by the non-macromolecular additives · CPC title

• G03F7/0236

  Condensation products of carbonyl compounds and phenolic compounds, e.g. novolak resins · CPC title

• G03F7/004 Primary

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

• G03F7/091 Primary

  characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement · CPC title