Chemically amplified photoresist composition, photoresist pattern, and method for preparing photoresist pattern

Patent metadata

Field	Value
Publication number	US-2020233302-A1
Application number	US-201816488515-A
Country	US
Kind code	A1
Filing date	Sep 14, 2018
Priority date	Sep 15, 2017
Publication date	Jul 23, 2020
Grant date	—

Abstract

The present invention relates to a chemically amplified photoresist composition including an alkali-soluble resin and a polymeric photo-acid generator having a predetermined structure, a photoresist pattern produced from the chemically amplified photoresist composition, and a method for preparing the chemically amplified photoresist pattern.

First claim

1 . A chemically amplified photoresist composition comprising: a first alkali-soluble resin comprising a repeating unit; and
a polymeric photo-acid generator in which a photo-acid generating group is linked with a second alkali-soluble resin via a functional group containing a C 1-20 alkylene sulfide.

2 . The chemically amplified photoresist composition according to claim 1 , wherein each of the first alkali-soluble resin and the second alkali-soluble resin is at least one selected from the group of an acrylic resin, a novolac resin, and a polyhydroxystyrene resin.

3 . The chemically amplified photoresist composition according to claim 1 , wherein the second alkali-soluble resin contained in the polymeric photo-acid generator is the same as the first alkali-soluble resin or contains a repeating unit that is the same repeating unit of the first alkali-soluble resin.

4 . The chemically amplified photoresist composition according to claim 1 , wherein the composition contains 0.01 to 50 parts by weight of the polymeric photo-acid generator, based on 100 parts by weight of the first alkali-soluble resin.

5 . The chemically amplified photoresist composition according to claim 1 , wherein
the second alkali-soluble resin includes a structure derived from any one or more of monomers represented by the following Chemical Formulae 1 to 10:

wherein, in Chemical Formulae 1 to 10,
R 1 is hydrogen, a halogen, a C 1-10 alkyl, a C 3-10 cycloalkyl, or a C 2-10 alkenyl, and n1, n2, and n3 are each independently an integer of 1 to 18.

6 . The chemically amplified photoresist composition according to claim 1 , wherein
the photo-acid generating group is derived from a compound of the following Chemical Formula 11 or 12:

wherein, in Chemical Formulae 11 and 12,
R 2 to R 5 are each independently hydrogen, a halogen, a thiol, a C 1-20 alkyl, a C 3-20 cycloalkyl, a C 2-20 alkenyl, a C 1-20 alkoxy, a C 1-10 fluoroalkyl, a C 1-20 alkylthiol, or a C 2-20 alkenethiol,
at least one of R 3 to R 5 is a thiol, a C 2-20 alkenyl, or a C 2-20 alkenethiol,
R 6 is a C 1-10 alkoxy, a C 1-10 fluoroalkyl, or a C 1-10 alkylthiol,
L 1 is a substituted or unsubstituted C 1-4 alkylene containing a carbonyl linked to the nitrogen atom, and
L 2 is carbonyl or methylene.

7 . The chemically amplified photoresist composition according to claim 6 , wherein any one of the second alkali-soluble resin and the compound of Chemical Formula 11 or 12 includes a functional group containing a double bond, and the other includes a functional group containing a thiol.

8 . The chemically amplified photoresist composition according to claim 1 , wherein the photo-acid generating group is derived from any one of compounds represented by the following Chemical Formulae 13 to 15:

wherein, in Chemical Formulae 13 to 15,
R 7 and R 8 are each independently hydrogen, a halogen, a thiol, a C 1-20 alkyl, a C 3-20 cycloalkyl, a C 2-20 alkenyl, a C 1-20 alkoxy, a C 1-10 fluoroalkyl, a C 1-20 alkylthiol, or a C 2-20 alkenethiol,
at least one of R 7 and R 8 is a thiol, a C 2-20 alkenyl, or a C 2-20 alkenethiol, and
R 9 is a C 1-10 alkoxy, a C 1-10 fluoroalkyl, or a C 1-10 alkyl thiol.

9 . The chemically amplified photoresist composition according to claim 1 , wherein each of the first alkali-soluble resin and the polymeric photo-acid generator has a weight average molecular weight of 1000 to 500,000.

10 . A thick film photoresist pattern produced from the chemically amplified photoresist composition of claim 1 .

11 . A method for preparing a thick film photoresist pattern comprising the steps of: a lamination step of laminating a thick film photoresist layer comprising the chemically amplified photoresist composition of claim 1 on a support;
an exposure step of irradiating the thick film photoresist layer with radiation including an electromagnetic wave or a particle beam; and
a development step of developing the thick film photoresist layer after exposure to obtain a thick film photoresist pattern.

12 . The chemically amplified photoresist composition according to claim 5 , wherein the photo-acid generating group is derived from a compound of the following Chemical Formula 11 or 12:

wherein, in Chemical Formulae 11 and 12,
R 2 to R 5 are each independently hydrogen, a halogen, a thiol, a C 1-20 alkyl, a C 3-20 cycloalkyl, a C 2-20 alkenyl, a C 1-20 alkoxy, a C 1-10 fluoroalkyl, a C 1-20 alkylthiol, or a C 2-20 alkenethiol,
at least one of R 3 to R 5 is a thiol, a C 2-20 alkenyl, or a C 2-20 alkenethiol,
R 6 is a C 1-10 alkoxy, a C 1-10 fluoroalkyl, or a C 1-10 alkylthiol,
L 1 is a substituted or unsubstituted C 1-4 alkylene containing a carbonyl linked to the nitrogen atom, and
L 2 is carbonyl or methylene.

13 . The chemically amplified photoresist composition according to claim 12 , wherein any one of the second alkali-soluble resin and the compound of Chemical Formula 11 or 12 includes a functional group containing a double bond, and the other includes a functional group containing a thiol.

Assignees

• Lg Chemical Ltd

Inventors

• Lim Min Young
• Kim Ji Hye
• Kim Yongmi

Classifications

• C07D221/14

  Aza-phenalenes, e.g. 1,8-naphthalimide · CPC title

• G03F7/038 Primary

  Macromolecular compounds which are rendered insoluble or differentially wettable (G03F7/075 takes precedence; macromolecular azides G03F7/012; macromolecular diazonium compounds G03F7/021) · CPC title

• G03F7/039

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

• G03F7/2004

  characterised by the use of a particular light source, e.g. fluorescent lamps or deep UV light · CPC title

• G03F7/0397 Primary

  the macromolecular compound having an alicyclic moiety in a side chain · CPC title