IP Library Granted Patent US 11,806,830
Granted Patent B2
US 11,806,830 · App. 17/154,744 · Granted Nov 7, 2023

Formulations for chemical mechanical polishing pads and CMP pads made therewith

Inventors: Bryan E. Barton (Lincoln University, PA); Teresa Brugarolas Brufau (Philadelphia, PA)
Assignee: Rohm and Haas Electronic Materials CMP Holdings, Inc.
B24B37/24B24B37/22
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Quick Facts
Patent No.
US 11,806,830
App. No.
17/154,744
Granted
Nov 7, 2023
Kind
B2
Abstract

CMP polishing pads or layers made from a polyurethane reaction product of a reaction mixture comprising (i) a liquid aromatic isocyanate component comprising one or more aromatic diisocyanates or a linear aromatic isocyanate-terminated urethane prepolymer, and (ii) a liquid polyol component comprising a) one or more polymeric polyols, b) from 12 to 40 wt. %, based on the total weight of the liquid polyol component, of a curative mixture of one or more small chain difunctional polyols having from 2 to 9 carbon atoms, a liquid aromatic diamine, wherein the mole ratio of the total moles of hydroxyl and amino moieties in the liquid polyol, small chain difunctional polyols and liquid aromatic diamine to mole of isocyanate in the aromatic diisocyanates or linear aromatic isocyanate-terminated urethane prepolymer ranges from 1.0:1.0 to 1.15:1.0. The polishing layer is capable of forming a total texture depth, as measured by Sdr, a parameter defined by the ISO 25178 standard, upon treatment by a surface conditioning disk, in the range of from 0 to 0.4.

Claims (10)

1. A chemical mechanical planarization (CMP) polishing pad for polishing a substrate chosen from at least one of a magnetic substrate, an optical substrate and a semiconductor substrate, the CMP polishing pad comprising a polishing layer adapted for polishing the substrate, the polishing layer being a polyurethane, the polyurethane is a product of a reaction mixture comprising (i) a liquid aromatic isocyanate component comprising one or more aromatic diisocyanates or a linear aromatic isocyanate-terminated urethane prepolymer having an unreacted isocyanate (NCO) concentration of from 20 to 40 wt. %, based on the total solids weight of the liquid aromatic isocyanate component, and (ii) a liquid polyol component comprising a) one or more polymeric polyols, and b) from 12 to 40 wt. %, based on the total weight of the liquid polyol component, of a curative mixture of one or more small chain difunctional polyols having from 2 to 9 carbon atoms, and a liquid aromatic diamine which is a liquid under ambient conditions, wherein the mole ratio of liquid aromatic diamine to the total moles of small chain difunctional polyols and liquid aromatic diamine ranges from 15:85 to 50:50, and wherein the mole ratio of the total moles of hydroxyl and amino moieties in the liquid polyol, small chain difunctional polyols and liquid aromatic diamine to mole of isocyanate in the aromatic diisocyanates or linear aromatic isocyanate-terminated urethane prepolymer ranges from 1.0:1.0 to 1.1:1.0, the reaction mixture comprises 48 to 68 wt. % of hard segment materials, based on the total weight of the reaction mixture, the CMP polishing layer has a hardness in the range of from 54 Shore A (2 second) to 72 Shore D (2 second), and a density of from 0.45 to 0.99 g/mL and, yet still further wherein, the polishing layer is capable of forming a total texture depth, as measured by Sdr, a parameter defined by the ISO 25178 standard, upon treatment by a surface conditioning disk, in the range of from 0 to 0.4.

2. The CMP polishing pad as claimed in claim 1 , wherein the (i) liquid aromatic isocyanate component comprises a linear methylene diphenyl diisocyanate (MDI) prepolymer or MDI.

3. The CMP polishing pad as claimed in claim 1 , wherein the (ii) liquid polyol component comprises a) one or more polymeric polyols which is selected from the group consisting of polytetramethylene glycol (PTMEG), polypropylene glycol (PPG), a hexafunctional polyol, and mixtures thereof.

4. The CMP polishing pad as claimed in claim 1 , wherein in the b) curative mixture of the (ii) liquid polyol component, the one or more small chain difunctional polyols having from 2 to 9 carbon atoms is selected from the group consisting of ethylene glycol, 1,2-propylene glycol, 1,3-propylene glycol, 1,2-butanediol, 1,3-butanediol, 2-methyl-1,3-propanediol, 1,4-butanediol, neopentyl glycol, 1,5-pentanediol, 3-methyl-1,5-pentanediol, 1,6-hexanediol, diethylene glycol, dipropylene glycol, tripropylene glycol, and mixtures thereof.

5. The CMP polishing pad as claimed in claim 1 , wherein in the b) curative mixture, the liquid aromatic diamine is selected from the group consisting of dimethylthio-toluene diamines, diethyl toluene diamines, tert-butyl toluene diamines, chlorotoluenediamines, N,N′-dialkylaminodiphenylmethane, and mixtures thereof.

6. The CMP polishing pad as claimed in claim 1 , wherein in the b) curative mixture, the mole ratio of liquid aromatic diamine to the total moles of small chain difunctional polyols and liquid aromatic diamine ranges from 23:77 to 35:65.

7. The CMP polishing pad as claimed in claim 1 , wherein reaction mixture comprises from 58 to 63 wt. % of hard segment materials, based on the total weight of the reaction mixture.

8. The CMP polishing pad as claimed in claim 1 , wherein the CMP polishing pad contains no microelements other than those formed by gas, water or CO 2 -amine adduct.

9. The CMP polishing pad as claimed in claim 1 , wherein the polishing layer is capable of forming a total texture depth, as measured by Sdr, a parameter defined by the ISO 25178 standard, upon treatment by a surface conditioning disk, in the range of from 0 to 0.3.

10. The CMP polishing pad as claimed in claim 9 , wherein the polishing layer is capable of forming a total texture depth, as measured by Sdr, a parameter defined by the ISO 25178 standard, upon treatment by a surface conditioning disk, in the range of from 0.1 to 0.3.

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 CMP HOLDINGS INC.
To: DUPONT ELECTRONIC MATERIALS HOLDING, INC.
Reel/Frame 069274/0160 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 2, 2021
From: BARTON, BRYAN E.; BRUGAROLAS BRUFAU, TERESA
To: ROHM AND HAAS ELECTRONIC MATERIALS CMP HOLDINGS, INC.
Reel/Frame 055808/0860 →