Photoresist compositions and methods of fabricating a semiconductor device

Patent metadata

Field	Value
Publication number	US-12468226-B2
Application number	US-202218056332-A
Country	US
Kind code	B2
Filing date	Nov 17, 2022
Priority date	Nov 18, 2021
Publication date	Nov 11, 2025
Grant date	Nov 11, 2025

Abstract

Photoresist compositions may include a photosensitive polymer including a first repeating unit of Chemical Formula 1; a photoacid generator (PAG); and a solvent.

First claim

What is claimed is:

1 . A photoresist composition comprising:
a photosensitive polymer; a photoacid generator (PAG); and a solvent, wherein the photosensitive polymer comprises a first repeating unit having a structure of Chemical Formula 1:

wherein R 1 is hydrogen, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 15 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or a cycloalkenyl group having 3 to 12 carbon atoms,
R 2 is an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 15 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, a cycloalkenyl group having 3 to 12 carbon atoms, or a carboxylate group having 1 to 6 carbon atoms, and
R 3 is hydrogen, an alkyl group having 1 to 3 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, an alkynyl group having 2 to 4 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, an aryl group having 6 to 10 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, or a cycloalkenyl group having 3 to 7 carbon atoms.

2 . The photoresist composition of claim 1 , wherein the photosensitive polymer further comprises a second repeating unit comprising an acid-labile protecting group.

3 . The photoresist composition of claim 2 , wherein the second repeating unit has a structure of Chemical Formula 2:

wherein R 2a is a hydrogen atom, a linear or branched alkyl group having 1 to 6 carbon atoms, a halogen atom, or a linear or branched alkyl halide having 1 to 6 carbon atoms, and
R 2b is the acid-labile protecting group.

4 . The photoresist composition of claim 2 , wherein the photosensitive polymer further comprises a third repeating unit having a structure of Chemical Formula 3:

wherein R 4a is hydrogen, a hydroxyl group, a carboxyl group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms, and
R 4b is a hydroxyl group or a carboxyl group.

5 . The photoresist composition of claim 1 , wherein in the photosensitive polymer, a number of first repeating units is about 5% to about 30% of a number of total repeating units.

6 . The photoresist composition of claim 1 , wherein R 1 is hydrogen, a methyl group, an ethyl group, or an aryl group, and
R 2 is a methyl group, an ethyl group, a propyl group, a methoxy group, an ethoxy group, a propoxy group, an aryl group, a formate group, or an acetate group.

7 . The photoresist composition of claim 1 , wherein the photosensitive polymer further comprises a fourth repeating unit having a structure of Chemical Formula 4:

wherein R 5 is hydrogen, an alkyl group having 1 to 3 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, an alkynyl group having 2 to 4 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, an aryl group having 6 to 10 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, or a cycloalkenyl group having 3 to 7 carbon atoms, and
R 6 is a linear, branched, and/or cyclic saturated or unsaturated hydrocarbon group having 1 to 20 carbon atoms and comprising 1 to 5 heteroatoms or no heteroatom.

8 . The photoresist composition of claim 7 , wherein in the photosensitive polymer, a total number of first and fourth repeating units is about 10% to about 40% of a number of total repeating units.

9 . The photoresist composition of claim 1 , wherein the PAG is capable of generating an acid in response to irradiation of light having a wavelength of 13.5 nm.

10 . The photoresist composition of claim 1 , further comprising a basic quencher in an amount of about 0.01 wt % to about 5 wt % based on a total weight of the photoresist composition.

11 . A photoresist composition comprising:
a photosensitive polymer; a photoacid generator (PAG); a basic quencher; and a solvent, wherein the photosensitive polymer is a random copolymer comprising a first repeating unit having a structure of Chemical Formula 1, a second repeating unit having a structure of Chemical Formula 2, and a third repeating unit having a structure of Chemical Formula 3:

wherein R 1 is hydrogen, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 15 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or a cycloalkenyl group having 3 to 12 carbon atoms,
R 2 is an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 15 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, a cycloalkenyl group having 3 to 12 carbon atoms, or a carboxylate group having 1 to 6 carbon atoms,
R 3 is hydrogen, an alkyl group having 1 to 3 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, an alkynyl group having 2 to 4 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, an aryl group having 6 to 10 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, or a cycloalkenyl group having 3 to 7 carbon atoms,
R 4a is hydrogen, a hydroxyl group, a carboxyl group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms, R 4b is a hydroxyl group or a carboxyl group, and
R 2a is a hydrogen atom, a linear or branched alkyl group having 1 to 6 carbon atoms, a halogen atom, or a linear or branched alkyl halide group having 1 to 6 carbon atoms, and R 2b is an acid-labile protecting group.

12 . The photoresist composition of claim 11 , wherein the first repeating unit comprises a solubility adjusting moiety, and
a repeating unit having a structure of Chemical Formula 5 or 6 is generated by reacting the solubility adjusting moiety with an acid:

13 . The photoresist composition of claim 11 , wherein in the photosensitive polymer, a number of first repeating units is about 5% to about 30% of a number of total repeating units, a number of second repeating units is about 35% to about 65% of the number of total repeating units, and a number of third repeating units is about 20% to about 40% of the number of total repeating units.

Assignees

• Samsung Electronics Co Ltd

Inventors

• Im Honggu
• Kim Sumin
• Kim Yechan
• Kim Jinjoo
• Kim Hyunwoo
• Park Sunghwan
• Park Juhyeon
• Park Jicheol
• Song Giyoung
• Hong Sukkoo

Classifications

• H10P76/2042

  using lasers · CPC title

• G03F7/0384

  with ethylenic or acetylenic bands in the main chain of the photopolymer · CPC title

• C08F212/08

  Styrene · CPC title

• C08F220/18

  with acrylic or methacrylic acids · CPC title

• C08F220/285

  and containing a polyether chain in the alcohol moiety · CPC title