Semiconductor resist composition, and method of forming patterns using the composition

Patent metadata

Field	Value
Publication number	US-11092890-B2
Application number	US-201916712701-A
Country	US
Kind code	B2
Filing date	Dec 12, 2019
Priority date	Jul 31, 2018
Publication date	Aug 17, 2021
Grant date	Aug 17, 2021

Abstract

A semiconductor resist composition includes an organometallic compound represented by Chemical Formula 1 and a solvent:wherein, in Chemical Formula I, R1 is an aliphatic hydrocarbon group, an aromatic hydrocarbon group, or an —alkylene-O-alkyl group, and R2 to R4 are each independently selected from —ORa and —OC(═O)Rb, where Ra is not hydrogen.

First claim

What is claimed is:

1. A semiconductor resist composition, comprising
an organometallic compound represented by Chemical Formula 1, and
a solvent:

wherein, in Chemical Formula 1,
R 1 is selected from the group consisting of a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 benzyl group, and —R c —O—R d , wherein R c is a substituted or unsubstituted C1 to C20 alkylene group and Rd is a substituted or unsubstituted C1 to C20 alkyl group,
R 2 to R 4 are each independently selected from the group consisting of -OR a and —OC(═O)R b ), and at least one of R 2 to R 4 is —OC(═O)R b ,
R a is selected from the group consisting of a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, and combinations thereof, and
R b is selected from the group consisting of hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, and combinations thereof.

2. The semiconductor resist composition of claim 1 , wherein R 1 is selected from the group consisting of a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C3 to C20 alkenyl group, a substituted or unsubstituted C3 to C20 alkynyl group, and —R c —O—R d , wherein RC is a substituted or unsubstituted C1 to C20 alkylene group and R d is a substituted or unsubstituted C1 to C20 alkyl group.

3. The semiconductor resist composition of claim 1 , wherein R a is selected from the group consisting of a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C2 to C8 alkenyl group, a substituted or unsubstituted C2 to C8 alkynyl group, and a substituted or unsubstituted C6 to C30 arylalkyl group, and Rb is selected from the group consisting of hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C2 to C8 alkenyl group, a substituted or unsubstituted C2 to C8 alkynyl group, and a substituted or unsubstituted C6 to C30 arylalkyl group.

4. The semiconductor resist composition of claim 1 , wherein the organometallic compound is represented by at least one of Chemical Formula 3 to Chemical Formula 4:

wherein, in Chemical Formula 3 to Chemical Formula 4,
R 1 is selected from the group consisting of a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 benzyl group, and —R c —O—R d , wherein R c is a substituted or unsubstituted C1 to C20 alkylene group and Rd is a substituted or unsubstituted C1 to C20 alkyl group,
R 33 are each independently selected from the group consisting of a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C2 to C8 alkenyl group, a substituted or unsubstituted C2 to C8 alkynyl group, and a substituted or unsubstituted C6 to C30 arylalkyl group, and
R 22 , R 23 , R 24 , R 32 , and R 34 are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C2 to C8 alkenyl group, a substituted or unsubstituted C2 to C8 alkynyl group, and a substituted or unsubstituted C6 to C30 arylalkyl group.

5. The semiconductor resist composition of claim 4 , wherein R 1 is selected from the group consisting of a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C3 to C20 alkenyl group, a substituted or unsubstituted C3 to C20 alkynyl group, and —R c —O—R d , wherein R c is a substituted or unsubstituted C1 to C20 alkylene group and R d is a substituted or unsubstituted C1 to C20 alkyl group.

6. The semiconductor resist composition of claim 1 , wherein the composition further comprises an additive selected from the group consisting of a surfactant, a cross-linking agent, a leveling agent, and combinations thereof.

7. The semiconductor resist composition of claim 6 , wherein the surfactant is selected from the group consisting of an alkyl benzene sulfonate salt, an alkyl pyridinium salt, polyethylene glycol, a quaternary ammonium salt, and combinations thereof.

8. The semiconductor resist composition of claim 6 , wherein the cross-linking agent is a melamine-based, substituted urea-based, or a polymer-based cross-linking agent.

9. The semiconductor resist composition of claim 1 , further comprising a silane coupling agent as an adherence enhancer.

10. The semiconductor resist composition of claim 1 , wherein the organometallic compound is represented by at least one of Chemical Formula 5 to Chemical Formula 9 and Chemical Formula 13:

11. A method of forming patterns, the method comprising:
coating the semiconductor resist composition of claim 1 on an etching subject layer to form a photoresist layer;
patterning the photoresist layer to form a photoresist pattern; and
etching the etching subject layer using the photoresist pattern as an etching mask.

12. The method of claim 11 , wherein the photoresist pattern is formed using light in a wavelength of about 5 nm to about 150 nm.

13. The method of claim 11 , herein the etching subject layer is provided on a substrate.

14. The method of claim 13 , further comprising providing a resist underlayer between the substrate and the photoresist layer.

15. The method of claim 11 , further comprising:
drying the coated semiconductor resist composition at about 80° C. to about 120° C., and
curing the patterned photoresist layer at 90° C. to about 200° C.

16. The method of claim 13 , wherein the photoresist pattern has a width of about 5 nm to about 100 nm.

17. The method of claim 13 , wherein the photoresist pattern is formed using an extreme ultraviolet (EUV) light source of a wavelength of about 13.5 nm.

Assignees

• Samsung Sdi Co Ltd

Inventors

• Moon Kyung Soo
• Kim Jaehyun
• Na Yoong Hee
• Namgung Ran
• Cheon Hwansung
• Chae Seungyong

Classifications

• H10P50/69

  using masks for semiconductor materials · CPC title

• H10P14/683

  carbon-based polymeric organic materials, e.g. polyimides, poly cyclobutene or PVC · CPC title

• H10P14/68

  Organic materials, e.g. photoresists · CPC title

• H10P14/61

  using masks · CPC title

• H10P76/2042

  using lasers · CPC title