Coating compositions for use with an overcoated photoresist

Patent metadata

Field	Value
Publication number	US-11262656-B2
Application number	US-201615088091-A
Country	US
Kind code	B2
Filing date	Mar 31, 2016
Priority date	Mar 31, 2016
Publication date	Mar 1, 2022
Grant date	Mar 1, 2022

Abstract

Organic coating compositions, particularly antireflective coating compositions for use with an overcoated photoresist, are provided that comprise that a blend of two or more resins, where one resin has epoxy groups either pendant or fused to the polymer backbone. Preferred coating compositions include: 1) a first resin that comprises one or more epoxy reactive groups; and 2) a crosslinker resin that is distinct from the first resin and comprises epoxy groups.

First claim

What is claimed is:

1. A method for forming a photoresist relief image, comprising:
a) applying on a substrate a layer of a coating composition comprising:
1) a first resin that comprises one or more epoxy reactive groups, and wherein the first resin is a polyester and comprises polyester cyanurate groups; and
2) a crosslinker resin that is distinct from the first resin and comprises epoxy groups,
wherein: i) the crosslinker resin is free of any epoxy reactive groups; or (ii) the first resin and/or crosslinker resin comprises optionally substituted phenyl groups, optionally substituted naphthyl groups or optionally substituted anthracenyl groups; and

b) applying a layer of a photoresist composition above the coating composition layer,
wherein the following 1), 2) and/or 3):
1) the crosslinker resin comprises one or more repeat units of the following Formula (1):

wherein:
R 1 is selected from the group consisting of hydrogen, halogen, and cyano;
R 2 is a linking group selected from the group consisting of —C(═O)-O-, -O-, -(CH 2 ) h -O-, and -O-CH 2 ) n - where n is a positive integer, -(CH 2 ) n - where n is a positive integer, -(optionally substituted carbocyclic aryl)-O-, -(optionally substituted carbocylic aryl)-, -O-(optionally substituted carbocyclic aryl)-, -(optionally substituted heteroaryl)-O-, -(optionally substituted heteroaryl)-, and -O-(optionally substituted heteroaryl)-,
R 2′ is selected from the group consisting of optionally substituted C 1 to C 12 linear, branched or cyclic alkyl, and optionally substituted C 6 to C 15 aryl, optionally containing heteroatoms, and wherein R 2′ comprises at least one epoxy group,
or R 2 and R 2′ are taken together to form a carbon alicyclic ring that comprises a pendant or fused epoxy group;
and/or
2) the first resin comprises a unit of the following Formula (2):

wherein in Formula (2): R 1 is selected from the group consisting of hydrogen, halogen, cyano, and optionally substituted alkyl;
R 2 is a linking group selected from the group consisting of —C(═O)-O-, -O-, -(CH 2 ) n ,-O-, and -O-(CH 2 ) n - where n is a positive integer, -(CH 2 ) n - where n is a nonnegative integer, -(optionally substituted carbocyclic aryl)-O-, -(optionally substituted carbocylic aryl)-, -O-(optionally substituted carbocyclic aryl)-, -(optionally substituted heteroaryl)-O-, -(optionally substituted heteroaryl)-, and -O-(optionally substituted heteroaryl)-,
R 3 is selected from the group consisting of hydrogen, halogen, cyano, and optionally substituted alkyl; and
R 4 is hydrogen, optionally substituted alkyl, optionally substituted carbocyclic aryl, or optionally substituted heteroaryl; and
R 6 is optionally substituted alkyl, optionally substituted cyclic alkyl, and optionally substituted carbocyclic aryl, and optionally substituted heteroaryl, wherein R 6 comprises at least one group that comprises a nucleophilic oxygen, nitrogen or sulfur group, and/or
3) the crosslinker resin is an acrylate epoxy resin.

2. The method of claim 1 wherein the first resin epoxy reactive groups comprise a hydroxy, amine and/or thio moiety and/or other nucleophilic group that comprises a nucleophilic oxygen, nitrogen or sulfur group that can react with an epoxy group of the crosslinker resin during thermal treatment of the coating composition.

3. The method of claim 1 wherein the crosslinker resin is free of any epoxy reactive groups.

4. The method of claim 1 wherein the first resin is free of any epoxy groups.

5. The method of claim 1 wherein the crosslinker resin is an acrylate epoxy resin.

6. The method of claim 1 wherein the first resin and/or crosslinker resin comprises optionally substituted phenyl groups, optionally substituted naphthyl groups or optionally substituted anthracenyl groups.

7. The method of claim 1 wherein the crosslinker resin comprises one or more repeat units of the following Formula (1):

wherein:
R 1 is selected from the group consisting of hydrogen, halogen, and cyano;
R 2 is a linking group selected from the group consisting of —C(═O)-O-, -O-, -(CH 2 ) h -O-, and -O-(CH 2 ) n - where n is a positive integer, -(CH 2 ) n - where n is a positive integer, -(optionally substituted carbocyclic aryl)-O-, -(optionally substituted carbocylic aryl)-, -O-(optionally substituted carbocyclic aryl)-, -(optionally substituted heteroaryl)-O-, -(optionally substituted heteroaryl)-, and -O-(optionally substituted heteroaryl)-,
R 2′ is selected from the group consisting of optionally substituted C 1 to C 12 linear, branched or cyclic alkyl, and optionally substituted C 6 to C 15 aryl, optionally containing heteroatoms, and wherein R 2′ comprises at least one epoxy group,
or R 2 and R 2′ are taken together to form a carbon alicyclic ring that comprises a pendant or fused epoxy group.

8. The method of claim 1 wherein the first resin comprises a unit of the following Formula (2):

wherein in Formula (2): R 1 is selected from the group consisting of hydrogen, halogen, cyano, and optionally substituted alkyl;
R 2 is a linking group selected from the group consisting of —C(═O)-O-, -O-, -(CH 2 ) n -O-, and -O-(CH 2 ) n - where n is a positive integer, -(CH 2 ) n - where n is a nonnegative integer, -(optionally substituted carbocyclic aryl)-O-, -(optionally substituted carbocylic aryl)-, -O-(optionally substituted carbocyclic aryl)-, -(optionally substituted heteroaryl)-O-, -(optionally substituted heteroaryl)-, and -O-(optionally substituted heteroaryl)-,
R 3 is selected from the group consisting of hydrogen, halogen, cyano, and optionally substituted alkyl; and
R 4 is hydrogen, optionally substituted alkyl, optionally substituted carbocyclic aryl, or optionally substituted heteroaryl; and
R 6 is optionally substituted alkyl, optionally substituted cyclic alkyl, and optionally substituted carbocyclic aryl, and optionally substituted heteroaryl, wherein R 6 comprises at least one group that comprises a nucleophilic oxygen, nitrogen or sulfur group.

9. The method of claim 8 wherein the first resin further comprises a unit of the following Formula (3):

wherein in Formula (3):
R 1 is selected from the group consisting of hydrogen, halogen, cyano, and optionally substituted alkyl;
R 2 is a linking group selected from the group consisting of —C(═O)-O-, -O-, -(CH 2 ) n ,-O-, and -O-(CH 2 ) n - where n is a positive integer, -(CH 2 ) n - where n is a nonnegative integer, -(optionally substituted carbocyclic aryl)-O-, -(optionally substituted carbocylic aryl)-, -O-(optionally substituted carbocyclic aryl)-, -(optionally substituted heteroaryl)-O-, -(optionally substituted heteroaryl)-, and -O-(optionally substituted heteroaryl)-,
R 3 is selected from the group consisting of hydrogen, halogen, cyano, and optionally substituted alkyl; and
R 4 and R 5 are independently selected from the group consisting of hydrogen, optionally substituted alkyl, optionally substituted carbocyclic aryl, and optionally substituted heteroaryl.

Assignees

• Rohm & Haas Elect Materials Korea Ltd

Inventors

• Sim Jae Hwan
• Lee Hye-Won
• Cho EunHye
• Jo Jung Kyu
• Park Jin Hong
• Ryu Eui Hyun
• Lim Jae-Bong

Classifications

• C08G63/6856 Primary

  Dicarboxylic acids and dihydroxy compounds · CPC title

• C09D163/00

  Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins · CPC title

• C08G63/6826

  Dicarboxylic acids and dihydroxy compounds · CPC title

• C09D133/10

  Homopolymers or copolymers of methacrylic acid esters · CPC title

• C09D167/02 Primary

  Polyesters derived from dicarboxylic acids and dihydroxy compounds (C09D167/06 takes precedence) · CPC title