IP Library Granted Patent US 10,578,969
Granted Patent B2
US 10,578,969 · App. 16/245,631 · Granted Mar 3, 2020

Photoresist topcoat compositions and methods of processing photoresist compositions

Inventors: Cong Liu (Shrewsbury, MA); Doris H. Kang (Shrewsbury, MA); Deyan Wang (Hudson, MA); Cheng-Bai Xu (Southborough, MA); Mingqi Li (Shrewsbury, MA); Irvinder Kaur (Northborough, MA)
Assignee: Rohm and Haas Electronic Materials LLC
G03F7/11B05C11/08G03F7/0005G03F7/0387G03F7/09G03F7/162G03F7/2041G03F7/38G03F7/40H01L21/0274
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Quick Facts
Patent No.
US 10,578,969
App. No.
16/245,631
Granted
Mar 3, 2020
Kind
B2
Abstract

Photoresist topcoat compositions, comprising: a first polymer comprising a first repeat unit of general formula (I) and a second repeat unit of general formula (II): wherein: R 1 independently represents H, F or optionally fluorinated C1 to C4 alkyl; R 2 represents optionally fluorinated linear, branched or cyclic C1 to C20 alkyl; L 1 represents a single bond or a multivalent linking group; and n is an integer of from 1 to 5; a second polymer comprising a first repeat unit of general formula (III) and a second repeat unit of general formula (IV): wherein: R 3 independently represents H, F or optionally fluorinated C1 to C4 alkyl; R 4 represents linear, branched or cyclic C1 to C20 alkyl; R 5 represents linear, branched or cyclic C1 to C20 fluoroalkyl; L 2 represents a single bond or a multivalent linking group; and n is an integer of from 1 to 5; and a solvent. Coated substrates coated with the described topcoat compositions and methods of processing a photoresist composition are also provided. The invention finds particular applicability in the manufacture of semiconductor devices.

Claims (29)

1. A photoresist topcoat composition, comprising:

a first polymer comprising a first repeat unit of general formula (I) and a second repeat unit of general formula (II):

wherein: R 1 independently represents H, F or optionally fluorinated C1 to C4 alkyl; R2 represents optionally fluorinated linear, branched or cyclic C1 to C20 alkyl; L 1 represents a single bond or a multivalent linking group; and n is an integer of from 1 to 5;

a second polymer comprising a first repeat unit of general formula (III) and a second repeat unit of general formula (IV), wherein the second polymer is free of carboxylic acid groups:

wherein: R 3 independently represents H, F or optionally fluorinated C1 to C4 alkyl; R 4 represents linear, branched or cyclic C1 to C20 alkyl; R 5 represents linear, branched or cyclic C1 to C20 fluoroalkyl; L 2 represents a single bond or a multivalent linking group; and n is an integer of from 1 to 5;

a third polymer comprising a first repeat unit of the general formula (II), a second repeat unit of general formula (V) and a third repeat unit of general formula (VI):

wherein: R 6 independently represents H, F, and optionally fluorinated C1 to C4 alkyl; R 7 represents linear, branched or cyclic C1 to C20 alkyl; and R 8 represents a linear, branched or cyclic C1 to C20 fluoroalkyl; and

a solvent.

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

3. The photoresist topcoat composition of claim 1 , wherein the composition comprises a solvent mixture.

4. The photoresist topcoat composition of claim 3 , wherein the solvent mixture comprises: a first organic solvent chosen from C4 to C10 monovalent alcohols; and a second organic solvent represented by general formula (VII):

wherein: R 16 and R 17 are independently chosen from C3 to C8 alkyl; and the total number of carbon atoms in R 16 and R 17 taken together is greater than 6.

5. 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.

6. The coated substrate of claim 5 , wherein L 2 represents —C(O)OCH 2 —.

7. The coated substrate of claim 5 , wherein the composition comprises a solvent mixture.

8. The coated substrate of claim 7 , wherein the solvent mixture comprises: a first organic solvent chosen from C4 to C10 monovalent alcohols; and a second organic solvent represented by general formula (VII):

wherein: R 16 and R 17 are independently chosen from C3 to C8 alkyl; and the total number of carbon atoms in R 16 and R 17 taken together is greater than 6.

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 2 represents —C(O)OCH 2 —.

12. The method of claim 9 , wherein the composition comprises a solvent mixture.

13. The method of claim 12 , wherein the solvent mixture comprises: a first organic solvent chosen from C4 to C10 monovalent alcohols; and a second organic solvent represented by general formula (VII):

wherein: R 16 and R 17 are independently chosen from C3 to C8 alkyl; and the total number of carbon atoms in R 16 and R 17 taken together is greater than 6.

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 →
CHANGE OF NAME Recorded Oct 29, 2024
From: ROHM & HAAS ELECTRONIC MATERIALS LLC
To: DUPONT ELECTRONIC MATERIALS INTERNATIONAL, LLC
Reel/Frame 069272/0383 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 26, 2020
From: LIU, CONG; WANG, DEYAN; LI, MINGQI; KING, DORIS H.; XU, CHENG BAI; KAUR, IRVINDER
To: ROHM AND HAAS ELECTRONIC MATERIALS LLC
Reel/Frame 051622/0433 →
Continuity (3)
Continuation 15730875 · Oct 12, 2017
Provisional Application 62415468 · Oct 31, 2016
Related Publication 20190235385A1 · Aug 1, 2019