Photoresist composition and photoresist film using the same

Patent metadata

Field	Value
Publication number	US-10990009-B2
Application number	US-201816481339-A
Country	US
Kind code	B2
Filing date	Nov 20, 2018
Priority date	Nov 24, 2017
Publication date	Apr 27, 2021
Grant date	Apr 27, 2021

Abstract

A photoresist composition capable of forming a pattern in which a footing phenomenon is suppressed while being highly sensitive during formation of a fine pattern on a metal surface substrate, and capable of producing a photoresist film that is excellent in chemical stability, and a photoresist film using the photoresist composition.

First claim

The invention claimed is:

1. A photoresist composition for thick films to form a photoresist pattern on a support having a metal surface,
comprising:
a first (meth)acrylic resin containing a (meth)acrylic backbone and a functional group represented by the following Chemical Formula 1 bonded to one end of the backbone, and
a second (meth)acrylic resin containing a (meth)acrylic backbone and a thiol group bonded to one end of the backbone:

wherein, in Chemical Formula 1,
Z is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkylthioxy group having 1 to 20 carbon atoms, an arylthioxy group having 6 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, or an amine group having 1 to 20 carbon atoms,
wherein the photoresist composition is capable of minimizing a footing in the bottom of the photoresist pattern.

2. The photoresist composition according to claim 1 , wherein Z is an alkylthioxy group having 10 to 20 carbon atoms.

3. The photoresist composition according to claim 1 , wherein the first (meth)acrylic resin and the second (meth)acrylic resin comprises a functional group represented by the following Chemical Formula 2 or a functional group containing a moiety derived from a polymerization initiator that is bonded to the other end of the (meth)acrylic backbone:

wherein, in Chemical Formula 2,
R is an alkylene group having 1 to 20 carbon atoms, and
X is an alkyl group having 1 to 20 carbon atoms, or a carboxyl group.

4. The photoresist composition according to claim 3 , wherein, in Chemical Formula 2, R is an alkylene group having 1 to 5 carbon atoms substituted with a methyl group or a cyano group.

5. The photoresist composition according to claim 4 , wherein, in Chemical Formula 2, R is one of functional groups represented by the following Chemical Formulas 3 to 5:

6. The photoresist composition according to claim 1 , wherein the (meth)acrylic backbone contained in the first (meth)acrylic resin includes a repeating unit represented by the following Chemical Formula 6:

wherein, in Chemical Formula 6, R 1 is an alkyl group having 4 to 10 carbon atoms,
R 2 is an alkyl group having 1 to 3 carbon atoms, or an alkyl group substituted with an alkoxy group having 3 to 10 carbon atoms,
R 3 is an aryl group having 6 to 20 carbon atoms, or a cycloalkyl group having 3 to 20 carbon atoms,
R 4 to R 7 are each independently hydrogen or a methyl group, and
a ratio of a+c:b:d=2 to 8:0.5 to 3:1 to 5.

7. The photoresist composition according to claim 1 , wherein the first (meth)acrylic resin is a polymer represented by the following Chemical Formula 7:

wherein, in Chemical Formula 7,
Z is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkylthioxy group having 1 to 20 carbon atoms, an arylthioxy group having 6 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, or an amine group having 1 to 20 carbon atoms,
R is an alkylene group having 1 to 20 carbon atoms,
X is an alkyl group having 1 to 20 carbon atoms, or a carboxyl group,
R 1 is an alkyl group having 4 to 10 carbon atoms,
R 2 is an alkyl group having 1 to 3 carbon atoms, or an alkyl group substituted with an alkoxy group having 3 to 10 carbon atoms,
R 3 is an aryl group having 6 to 20 carbon atoms, or a cycloalkyl group having 3 to 20 carbon atoms,
R 4 to R 7 are each independently hydrogen or a methyl group, and
a ratio of a+c:b:d=2 to 8:0.5 to 3:1 to 5.

8. The photoresist composition according to claim 1 , wherein the second (meth)acrylic resin is a polymer represented by the following Chemical Formula 8:

wherein, in Chemical Formula 8,
R is an alkylene group having 1 to 20 carbon atoms,
X is an alkyl group having 1 to 20 carbon atoms, or a carboxyl group,
R 1 is an alkyl group having 4 to 10 carbon atoms,
R 2 is an alkyl group having 1 to 3 carbon atoms, or an alkyl group substituted with an alkoxy group having 3 to 10 carbon atoms,
R 3 is an aryl group having 6 to 20 carbon atoms or a cycloalkyl group having 3 to 20 carbon atoms,
R 4 to R 7 are each independently hydrogen or a methyl group, and
a ratio of a+c:b:d=2 to 8:0.5 to 3:1 to 5.

9. The photoresist composition according to claim 1 , wherein an amount of the second (meth)acrylic resin is from 10 mol % to 30 mol %, based on a total amount of the first (meth)acrylic resin and the second (meth)acrylic resin.

10. The photoresist composition according to claim 1 , further comprising a hydroxystyrene resin in an amount of 1 to 90 parts by weight, based on 100 parts by weight of a sum total of the first (meth)acrylic resin and the second (meth)acrylic resin.

11. The photoresist composition according to claim 1 , further comprising at least one additive selected from the group of a photoacid generator, an acid diffusion control agent, a plasticizer, a surfactant, a photoinitiator, and a dissolution inhibitor.

12. The photoresist composition according to claim 1 , wherein the photoresist composition contains less than 0.0001% by weight of a corrosion inhibitor including a triazine thiol compound or a triazole compound.

13. A photoresist film comprising a cured product of the photoresist composition of claim 1 .

Assignees

• Lg Chemical Ltd

Inventors

• Ahn Yongsik
• Kim Yongmi
• Lim Minyoung

Classifications

• C08F2438/03

  Use of a di- or tri-thiocarbonylthio compound, e.g. di- or tri-thioester, di- or tri-thiocarbamate, or a xanthate as chain transfer agent, e.g . Reversible Addition Fragmentation chain Transfer [RAFT] or Macromolecular Design via Interchange of Xanthates [MADIX] · CPC title

• G03F7/0392

  the macromolecular compound being present in a chemically amplified positive photoresist composition · CPC title

• G03F7/004 Primary

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

• G03F7/039 Primary

  Macromolecular compounds which are photodegradable, e.g. positive electron resists (G03F7/075 takes precedence; macromolecular quinonediazides G03F7/023) · CPC title

• G03F7/0045

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