IP Library Granted Patent US 12,234,369
Granted Patent B2
US 12,234,369 · App. 16/222,064 · Granted Feb 25, 2025

Photoresist topcoat compositions and methods of processing photoresist compositions

Inventors: Irvinder Kaur (Northborough, MA); Chunyi Wu (Shrewsbury, MA); Joshua A. Kaitz (Watertown, MA); Mingqi Li (Shrewsbury, MA); Doris Kang (Shrewsbury, MA); Xisen Hou (Lebanon, NH); Cong Liu (Shrewsbury, MA)
Assignee: DuPont Electronic Materials International, LLC
C09D133/02C09D133/06C09D133/08G03F7/0046G03F7/11G03F7/162G03F7/2041G03F7/32
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Quick Facts
Patent No.
US 12,234,369
App. No.
16/222,064
Granted
Feb 25, 2025
Kind
B2
Abstract

Photoresist topcoat compositions, comprising: a first polymer that is aqueous base soluble and is present in an amount of from 70 to 99 wt % based on total solids of the composition; a second polymer comprising a repeat unit of general formula (IV) and a repeat unit of general formula (V): wherein: R 5 independently represents H, halogen atom, C1-C3 alkyl, or C1-C3 haloalkyl; R 6 represents linear, branched or cyclic C1 to C20 fluoroalkyl; R 7 represents linear, branched or cyclic C1 to C20 fluoroalkyl; L 3 represents a multivalent linking group; and m is an integer of from 1 to 5; wherein the second polymer is free of non-fluorinated side chains; and wherein the second polymer is present in an amount of from 1 to 30 wt % based on total solids of the composition and a solvent. The invention finds particular applicability in the manufacture of semiconductor devices.

Claims (32)

1. A photoresist topcoat composition, comprising:

a first polymer that is aqueous base soluble and is present in an amount of from 70 to 99 wt % based on total solids of the composition;

a second polymer comprising a repeat unit of general formula (IV) and a repeat unit of general formula (V):

wherein: R 5 independently represents H, halogen atom, C1-C3 alkyl, or C1-C3 haloalkyl; R 6 represents linear, branched or cyclic C1 to C20 fluoroalkyl; R 7 represents linear, branched or cyclic C1 to C20 fluoroalkyl; L 3 represents a multivalent linking group; and m is an integer of from 1 to 5; wherein the second polymer is free of non-fluorinated side chains; and wherein the second polymer is present in an amount of from 1 to 30 wt % based on total solids of the composition;

a photoacid generator compound or a thermal acid generator compound; and

a solvent.

2. The photoresist topcoat composition of claim 1 , wherein L 3 represents —C(O)OCH2—.

3. The photoresist topcoat composition of claim 1 , wherein R 6 is branched.

4. The photoresist topcoat composition of claim 1 , wherein R 6 is perfluorinated.

5. The photoresist topcoat composition of claim 1 , wherein the first polymer comprises a repeat unit of general formula (I) and a repeat unit of general formula (II):

wherein: R 1 independently represents H, halogen atom, C1-C3 alkyl, or C1-C3 haloalkyl; R 2 represents optionally substituted linear, branched or cyclic C1-C20 alkyl; L 1 represents a single bond or a multivalent linking group; and n is an integer of from 1 to 5.

6. The photoresist topcoat composition of claim 1 , wherein the first polymer comprises a repeat unit of general formula (III):

wherein: R 3 is chosen from H, halogen atom, C1-C3 alkyl, or C1-C3 haloalkyl; R 4 is independently chosen from substituted or unsubstituted C1-C12 alkyl or substituted or unsubstituted C5-C18 aryl; X is a C2-C6 substituted or unsubstituted alkylene group; wherein X can optionally comprise one or more rings and together with R 4 can optionally form a ring; L 2 is a single bond or a linking group; p is an integer of from 1 to 50; and q is an integer of from 1 to 5.

7. The photoresist topcoat composition of claim 1 , wherein the solvent is an organic-based solvent.

8. A coated substrate, comprising:

a photoresist layer on a substrate; and

a topcoat layer formed from a photoresist topcoat composition of claim 1 on the photoresist layer.

9. A method of processing a photoresist composition, comprising:

(a) applying a photoresist composition over a substrate to form a photoresist layer;

(b) applying over the photoresist layer a photoresist topcoat composition of claim 1 to form a topcoat layer;

(c) exposing the topcoat layer and the photoresist layer to activating radiation; and

(d) contacting the exposed topcoat layer and photoresist layer with a developer to form a resist pattern.

10. The method of claim 9 , wherein the topcoat layer is formed by spin-coating, and the second polymer migrates to an upper surface of the topcoat layer during the spin-coating, wherein an upper surface of the topcoat layer consists essentially of the second polymer.

11. The method of claim 9 , wherein L 3 represents —C(O)OCH2—.

12. The method of claim 9 , wherein R 6 is branched.

13. The method of claim 9 , wherein R 6 is perfluorinated.

14. The method of claim 9 , wherein the first polymer comprises a repeat unit of general formula (I) and a repeat unit of general formula (II):

wherein: R 1 independently represents H, halogen atom, C1-C3 alkyl, or C1-C3 haloalkyl; R 2 represents optionally substituted linear, branched or cyclic C1-C20 alkyl; L 1 represents a single bond or a multivalent linking group; and n is an integer of from 1 to 5.

15. The method of claim 9 , wherein the first polymer comprises a repeat unit of general formula (III):

wherein: R 3 is chosen from H, halogen atom, C1-C3 alkyl, or C1-C3 haloalkyl; R 4 is independently chosen from substituted or unsubstituted C1-C12 alkyl or substituted or unsubstituted C5-C18 aryl; X is a C2-C6 substituted or unsubstituted alkylene group; wherein X can optionally comprise one or more rings and together with R 4 can optionally form a ring; L 2 is a single bond or a linking group; p is an integer of from 1 to 50; and q is an integer of from 1 to 5.

16. The method of claim 9 , wherein the solvent is an organic-based solvent.

17. The photoresist topcoat composition of claim 1 , wherein the second polymer consists of the repeat unit of general formula (IV) and the repeat unit of general formula (V).

Assignments (4)
SECURITY INTEREST Recorded Nov 3, 2025
From: QNITY ELECTRONICS, INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 073515/0243 →
SECURITY INTEREST Recorded Nov 3, 2025
From: QNITY ELECTRONICS, INC.
To: U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION, AS NOTES COLLATERAL AGENT
Reel/Frame 073517/0298 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 14, 2025
From: KAUR, IRVINDER; WU, CHUNYI; KAITZ, JOSHUA A; LI, MINGQI; KANG, DORIS; HOU, XISEN; LIU, CONG
To: ROHM AND HAAS ELECTRONIC MATERIALS LLC
Reel/Frame 069849/0229 →
CHANGE OF NAME Recorded Oct 29, 2024
From: ROHM & HAAS ELECTRONIC MATERIALS LLC
To: DUPONT ELECTRONIC MATERIALS INTERNATIONAL, LLC
Reel/Frame 069272/0383 →