IP Library Granted Patent US 12,242,193
Granted Patent B2
US 12,242,193 · App. 18/464,695 · Granted Mar 4, 2025

Coating compositions for use with an overcoated photoresist

Inventors: Eui-Hyun Ryu (Cheonan, KR); Jin Hong Park (Hwaseong, KR); You Rim Shin (Hwaseong, KR); Ji-Hon Kang (Hwaseong, KR); Jung-June Lee (Cheonan, KR); Jae-Bong Lim (Cheonan, KR)
Assignee: ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.
G03F7/091C08G63/6854C08G73/0644C09D5/006C09D179/04G03F7/11G03F7/16
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,242,193
App. No.
18/464,695
Granted
Mar 4, 2025
Kind
B2
Abstract

Organic coating compositions, particularly antireflective coating compositions for use with an overcoated photoresist, are provided that in a first aspect comprise a crosslinker component that comprises a structure of the following Formula (I):

Claims (37)

1. A coated substrate comprising:

a substrate having thereon:

a) a coating composition comprising:

a resin that comprises one or more glycoluril groups that have a non-hydrogen substituent at the 1 and/or 5 glycoluril ring positions, wherein the resin comprises 1) polyester linkages and/or 2) polymerized isocyanurate groups, wherein the one or more glycoluril groups are pendant glycoluril groups covalently linked to the resin; and

b) a layer of a photoresist composition above the coating composition layer.

2. The coated substrate of claim 1 , wherein the resin comprises one or more glycoluril groups of Formula (I):

wherein in Formula (I):

at least one of R 1 and R 2 is other than hydrogen or a resin linker;

each R is the same or different and independently selected from a resin linker, hydrogen, optionally substituted alkyl, optionally substituted heteroalkyl, or optionally substituted carbocyclic aryl; and

wherein at least one R group is an optionally substituted carbon alicyclic group, or an optionally substituted carbocyclic aryl group,

provided that one R is the resin linker, and the one or more glycouril groups are pendant moieties of a backbone of the resin; and

b) a layer of a photoresist composition above the coating composition layer.

3. The coated substrate of claim 2 , wherein at least one of R 1 and R 2 is optionally substituted alkyl or optionally substituted heteroalkyl.

4. The coated substrate of claim 2 , wherein the resin comprises 1) polyester linkages and/or 2) polymerized isocyanurate groups.

5. The coated substrate of claim 2 , wherein in Formula (I) one or more R groups comprise an optionally substituted carbon alicyclic group.

6. The coated substrate of claim 2 , wherein in Formula (I) one or more R groups comprise an optionally substituted heteroalkyl moiety.

7. The coated substrate of claim 2 , wherein the resin comprises a chromophore group.

8. The coated substrate of claim 2 , wherein one or more R groups comprise a carbocyclic aryl moiety.

9. The coated substrate of claim 2 , wherein the resin comprises a structure derived from formulae 1, 2, 3, 4, 5, 6, 7 or 8:

wherein in formulae 1, 2, 3, 4, 5, 6, 7 and 8, R 1 , R 2 , R 3 , and R 4 are independently selected from a resin linker, hydrogen, optionally substituted alkyl, optionally substituted heteroalkyl, or optionally substituted carbocyclic aryl, and at least one of R 1 , R 2 , R 3 , and R 4 is an optionally substituted carbon alicyclic group, or an optionally substituted carbocyclic aryl group.

10. The coated substrate of claim 2 , wherein the resin comprises a structure derived from one or more of the following:

11. A resin that comprises one or more glycoluril groups that have a non-hydrogen substituent at the 1 and/or 5 glycoluril ring positions, wherein the resin comprises 1) polyester linkages and/or 2) polymerized isocyanurate groups, wherein the one or more glycoluril groups are pendant glycoluril groups covalently linked to the resin.

12. The resin of claim 11 , wherein the resin comprises one or more glycoluril of the following Formula (I):

wherein in Formula (I):

at least one of R 1 and R 2 is other than hydrogen or a resin linker;

each R is the same or different and independently selected from a resin linker, hydrogen, optionally substituted alkyl, optionally substituted heteroalkyl, or optionally substituted carbocyclic aryl; and

wherein at least one R group is an optionally substituted carbon alicyclic group, or an optionally substituted carbocyclic aryl group;

provided that one R is the resin linker, and the one or more glycouril groups are pendant moieties of a backbone of the resin.

13. The resin of claim 12 , wherein at least one of R 1 and R 2 is optionally substituted alkyl or optionally substituted heteroalkyl.

14. The resin of claim 12 , wherein the resin comprises 1) polyester linkages and/or 2) polymerized isocyanurate groups.

15. The resin of claim 12 , wherein in Formula (I) one or more R groups comprise an optionally substituted carbon alicyclic group.

16. The resin of claim 12 , wherein in Formula (I) one or more R groups comprise an optionally substituted heteroalkyl moiety.

17. The resin of claim 12 , wherein the resin comprises a chromophore group.

18. The resin of claim 12 , wherein one or more R groups comprise a carbocyclic aryl moiety.

19. The resin of claim 12 , wherein the resin comprises a structure derived from formulae 1, 2, 3, 4, 5, 6, 7 or 8:

wherein in formulae 1, 2, 3, 4, 5, 6, 7 and 8, R 1 , R 2 , R 3 , and R 4 are independently selected from a resin linker, hydrogen, optionally substituted alkyl, optionally substituted heteroalkyl, or optionally substituted carbocyclic aryl, and at least one of R 1 , R 2 , R 3 , and R 4 is an optionally substituted carbon alicyclic group, or an optionally substituted carbocyclic aryl group.

20. The resin of claim 12 , wherein the resin comprises a structure derived from one or more of the following:

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 11, 2024
From: RYU, EUI-HYUN; PARK, JIN HONG; SHIN, YOU RIM; KANG, JI-HON; LEE, JUNG-JUNE; LIM, JAE-BONG
To: ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.
Reel/Frame 069197/0556 →
CHANGE OF NAME Recorded Oct 17, 2024
From: ROHM & HAAS ELECTRONIC MATERIALS KOREA LTD
To: DUPONT SPECIALTY MATERIALS KOREA LTD
Reel/Frame 069185/0438 →
Continuity (3)
Division 15337558 · Oct 28, 2016
Provisional Application 62249197 · Oct 31, 2015
Related Publication 20230418161A1 · Dec 28, 2023
References Cited (23)
US 5128232A · Thackeray et al. · 1992 [cited by applicant]
US 6261743B1 · Pavelchek et al. · 2001 [cited by applicant]
US 6852421B2 · Wayton et al. · 2005 [cited by applicant]
US 7691556B2 · Wu et al. · 2010 [cited by applicant]
US 7968268B2 · Wang · 2011 [cited by applicant]
US 20040067437A1 · Wayton et al. · 2004 [cited by applicant]
US 20060057501A1 · Wu et al. · 2006 [cited by applicant]
US 20070178406A1 · Vohra · 2007 [cited by examiner]
US 20100009297A1 · Yao et al. · 2010 [cited by applicant]
US 20100092894A1 · Liu et al. · 2010 [cited by applicant]
US 20110033800A1 · Zampini et al. · 2011 [cited by applicant]
US 20110033801A1 · Zampini et al. · 2011 [cited by applicant]
US 20120202155A1 · Yao et al. · 2012 [cited by applicant]
EP 0164248A2 · 1985 [cited by applicant]
EP 0783136A2 · 1997 [cited by applicant]
EP 0829766A2 · 1998 [cited by applicant]
TW 201002794A · 2010 [cited by applicant]
TW 201239047A1 · 2012 [cited by applicant]
WO 2010004378A1 · 2010 [cited by applicant]
WO 2010043946A2 · 2010 [cited by applicant]
English language summary of Japanese Office Action dated Sep. 13, 2017 in counterpart Japanese Application 2016-209997, 3 pages. [cited by applicant]
English language summary of Korean Office Action dated Feb. 23, 2018 issued in counterpart Korean Application 10-2016-0141353, 2 pages. [cited by applicant]
English language summary of Office Action issued by Taiwan Intellectual Property Office dated Nov. 28, 2017 in counterpart TW106-2(6)01205-10621204820, 3 pages. [cited by applicant]