Photobase generators and photoresist compositions comprising same

Patent metadata

Field	Value
Publication number	US-10274824-B2
Application number	US-201615153310-A
Country	US
Kind code	B2
Filing date	May 12, 2016
Priority date	May 15, 2015
Publication date	Apr 30, 2019
Grant date	Apr 30, 2019

Abstract

New photobase generators suitable for use in photoresists are provided that correspond to Formula (I):

X 1 —R 1 —O—C(═O)N(R 2 )R 3   (I)

wherein X 1 is an optionally substituted aromatic group; R 1 is a linker; and R 2 and R 3 are the same or different optionally substituted linear, branched or cyclic aliphatic group or an optionally substituted aromatic group, wherein at least one of R 2 and R 3 is an optionally substituted branched alkyl group having 4 or more carbon atoms.

First claim

What is claimed is:

1. A method for forming a photolithographic pattern, comprising:
(a) applying a layer of a positive-acting photoresist composition on a substrate, the photoresist composition comprising (1) a resin comprising photoacid-labile groups; (2) one or more acid generators; and (3) a photobase generator that corresponds to the following Formula (IA):
X 1 —(CYZ) n —O—C(═O)N(R 2 )R 3   (IA)

wherein X 1 is an optionally substituted aromatic group;
each Y and Z is independently hydrogen or a non-hydrogen substituent;
n is a positive integer; and
R 2 and R 3 are the same or different,
optionally substituted branched alkyl group having 4 or more carbon atoms; and
(b) patternwise exposing the photoresist composition layer to activating radiation; and
(c) developing the exposed photoresist composition layer to provide a photoresist relief image.

2. The method of claim 1 wherein X 1 is optionally substituted anthracenyl or phenyl.

3. The method of claim 1 wherein R 2 and R 3 are each independently optionally substituted branched alkyl having 6 or more carbon atoms.

4. The method of claim 1 wherein R 2 and/or R 3 are fluorinated branched alkyl having 4 or more carbon atoms.

5. The method of claim 1 wherein the photobase generator is selected from among the following:

6. The method of claim 1 wherein the substrate is a semiconductor substrate.

7. A positive-acting photoresist composition comprising:
(1) a resin comprising photoacid-labile groups;
(2) one or more acid generators; and
(3) a photobase generator that corresponds to the following Formula (IA):
X 1 —(CYZ) n —O—C(═O)N(R 2 )R 3   (IA)

wherein X 1 is an optionally substituted aromatic group;
each Y and Z is independently hydrogen or a non-hydrogen substituent;
n is a positive integer; and
R 2 and R 3 are the same or different
optionally substituted branched alkyl group having 4 or more carbon atoms.

8. The photoresist composition of claim 7 wherein X 1 is optionally substituted anthracenyl or phenyl.

9. The photoresist composition of claim 7 wherein R 2 and R 3 are each independently optionally substituted branched alkyl having 6 or more carbon atoms.

10. The photoresist composition of claim 7 wherein R 2 and/or R 3 are fluorinated branched alkyl having 4 or more carbon atoms.

11. The photoresist composition of claim 7 wherein the photobase generator is selected from among the following:

12. A positive-acting photoresist composition comprising:
(1) a resin;
(2) one or more acid generators; and
(3) a photobase generator that corresponds to the following Formula (TB):
X 1 —(CY′═CZ′) n —(CY′Z′) n′ —O—C(═O)N(R 2 )R 3   (IB)

wherein X 1 is an optionally substituted aromatic group;
each Y′ and Z′ is independently hydrogen or a non-hydrogen substituent;
n and n′ are each positive integer; and
R 2 and R 3 are the same or different optionally substituted linear, branched or cyclic aliphatic group or an optionally substituted aromatic group,
wherein at least one of R 2 and R 3 is an optionally substituted branched alkyl group having 4 or more carbon atoms.

13. A positive-acting photoresist composition comprising:
(1) a resin comprising photoacid-labile groups;
(2) one or more acid generators; and
(3) a photobase generator that corresponds to the following Formula (IA):
X 1 —(CYZ) n —O—C(═O)N(R 2 )R 3   (IA)

wherein X 1 is an optionally substituted aromatic group, wherein the aromatic group is not substituted by a NO 2 group;
each Y and Z is independently hydrogen or a non-hydrogen substituent;
n is a positive integer; and
R 2 and R 3 are the same or different optionally substituted linear, branched or cyclic aliphatic group or an optionally substituted aromatic group,
wherein at least one of R 2 and R 3 is an optionally substituted branched alkyl group having 4 or more carbon atoms, and R 2 and R 3 are not substituted by a CO 2 H group or an ester group.

14. A method for forming a photolithographic pattern, comprising:
(a) applying a layer of a photoresist composition of claim 13 on a substrate;
(b) patternwise exposing the photoresist composition layer to activating radiation; and
(c) developing the exposed photoresist composition layer to provide a photoresist relief image.

Assignees

• Rohm & Haas Elect Materials Korea Ltd

Inventors

• Jang Min-Kyung
• Ryu Eui Hyun
• Hong Chang-Young
• Kim Myung Yeol
• Lee Jung-June
• Hong Dong Je
• Kim Dong-Yong
• Lim Hae-Jin
• Ahn Jae Yun
• Jeon Ohk-Min

Classifications

• C07C271/14

  to carbon atoms of hydrocarbon radicals substituted by halogen atoms or by nitro or nitroso groups · CPC title

• C07C271/12

  to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals · CPC title

• G03F7/0045 Primary

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

• G03F7/322

  Aqueous alkaline compositions · CPC title

• G03F7/0046

  with perfluoro compounds, e.g. for dry lithography (G03F7/0048 takes precedence) · CPC title