Polishing pad employing polyamine and cyclohexanedimethanol curatives

Patent metadata

Field	Value
Publication number	US-11845156-B2
Application number	US-202016923688-A
Country	US
Kind code	B2
Filing date	Jul 8, 2020
Priority date	Jul 12, 2019
Publication date	Dec 19, 2023
Grant date	Dec 19, 2023

Abstract

A chemical-mechanical polishing pad comprising a thermosetting polyurethane polishing layer includes an isocyanate-terminated urethane prepolymer, a polyamine curative, and a cyclohexanedimethanol curative. The polyamine curative and the cyclohexanedimethanol curative are in a molar ratio of polyamine curative to cyclohexanedimethanol curative in a range from about 20:1 to about 1:1.

First claim

The invention claimed is:

1. A chemical-mechanical polishing pad comprising a thermosetting polyurethane polishing layer, the thermosetting polishing layer comprising:
an isocyanate-terminated urethane prepolymer;
a polyamine curative; and
a cyclohexanedimethanol curative;
wherein the polyamine curative and the cyclohexanedimethanol curative are in a molar ratio of polyamine curative to cyclohexanedimethanol curative in a range from about 20:1 to about 1:1.

2. The polishing pad of claim 1 , wherein the prepolymer is a reaction product of a toluene diisocyante (TDI) compound or a methylenediphenyl diisocyanate (MDI) compound and polytetramethylene ether glycol (PTMEG) or polypropylene ether glycol.

3. The polishing pad of claim 1 , wherein the prepolymer is an aromatic prepolymer selected from the group consisting of 75D prepolymers, 80D prepolymers, and mixtures thereof.

4. The polishing pad of claim 1 , wherein the polyamine curative is an aromatic diamine curative selected from the group consisting of aniline diamine compounds, toluene diamine compounds, aminobenzoate compounds, and mixtures thereof.

5. The polishing pad of claim 4 , wherein the aromatic diamine curative is selected from the group consisting of 4,4-methylenebis(2chloroaniline), dimethylthiotoluenediamine, and mixtures thereof.

6. The polishing pad of claim 1 , wherein the molar ratio of polyamine curative to cyclohexanedimethanol curative is in a range from about 10:1 to about 1.5:1.

7. The polishing pad of claim 1 , wherein the thermosetting polyurethane polishing layer comprises surface asperities and wherein the surface asperities have a ratio of a storage modulus at 25 degrees C. to a storage modulus at 75 degrees C. in a range from about 3 to about 20.

8. The polishing pad of claim 7 , wherein:
the isocyanate-terminated urethane prepolymer includes a 75D prepolymer; and
the surface asperities have a storage modulus (E′) at 25 degrees C. greater than about 500 MPa and a Shore D hardness at 25 degrees C. greater than about 60.

9. The polishing pad of claim 8 , wherein the surface asperities have a tensile toughness at 25 degrees C. greater than about 100 MPa.

10. The polishing pad of claim 7 , wherein:
the isocyanate-terminated urethane prepolymer includes an 80D prepolymer; and
the surface asperities have a storage modulus (E′) at 25 degrees C. greater than about 1000 MPa and a Shore D hardness at 25 degrees C. greater than about 70.

11. The polishing pad of claim 10 , wherein the surface asperities have a tensile toughness at 25 degrees C. greater than about 50 MPa.

12. The polishing pad of claim 1 , wherein the thermosetting polyurethane polishing layer further comprises a sufficient quantity of hollow microspheres such that the thermosetting polyurethane polishing layer has a porosity in a range from about 10 to about 50 percent.

13. The polishing pad of claim 1 , wherein:
the prepolymer is an aromatic prepolymer selected from the group consisting of 75D prepolymers, 80D prepolymers, and mixtures thereof;
the polyamine curative is an aromatic diamine curative selected from the group consisting of 4,4-methylenebis(2chloroaniline), dimethylthiotoluenediamine, and mixtures thereof; and
the molar ratio of polyamine curative to cyclohexanedimethanol curative is in a range from about 10:1 to about 1.5:1.

14. The polishing pad of claim 1 , wherein the thermosetting polyurethane polishing layer is adhered to a sub-pad.

15. A chemical-mechanical polishing pad comprising a thermosetting polyurethane polymer polishing layer, the thermosetting polishing layer comprising:
an isocyanate-terminated urethane prepolymer; and
a curative mixture comprising a polyamine curative and a cyclohexanedimethanol curative, wherein the curative mixture comprises from about 5 to about 50 mole percent of the cyclohexanedimethanol curative.

16. The polishing pad of claim 15 , wherein the prepolymer is a reaction product of a toluene diisocyante (TDI) compound or a methylenediphenyl diisocyanate (MDI) compound and polytetramethylene ether glycol (PTMEG) or polypropylene ether glycol.

17. The polishing pad of claim 15 , wherein the prepolymer is an aromatic prepolymer selected from the group consisting of 75D prepolymers, 80D prepolymers, and mixtures thereof.

18. The polishing pad of claim 15 , wherein the polyamine curative is an aromatic diamine curative selected from the group consisting of aniline diamine compounds, toluene diamine compounds, aminobenzoate compounds, and mixtures thereof.

19. The polishing pad of claim 18 , wherein the aromatic diamine curative is selected from the group consisting of 4,4-methylenebis(2chloroaniline), dimethylthiotoluenediamine, and mixtures thereof.

20. The polishing pad of claim 15 , wherein the curative mixture comprises from about 10 to about 40 weight percent of the cyclohexanedimethanol curative.

21. The polishing pad of claim 15 , wherein the curative mixture consists of the polyamine curative and the cyclohexanedimethanol curative.

22. The polishing pad of claim 15 , wherein the thermosetting polyurethane polishing layer comprises surface asperities and wherein the surface asperities have a ratio of a storage modulus at 25 degrees C. to a storage modulus at 75 degrees C. in a range from about 3 to about 20.

23. The polishing pad of claim 22 , wherein:
the isocyanate-terminated urethane prepolymer includes a 75D prepolymer; and
the surface asperities have a storage modulus (E′) at 25 degrees C. greater than about 500 MPa and a Shore D hardness at 25 degrees C. greater than about 60.

24. The polishing pad of claim 23 , wherein the surface asperities have a tensile toughness at 25 degrees C. greater than about 100 MPa.

25. The polishing pad of claim 22 , wherein:
the isocyanate-terminated urethane prepolymer includes an 80D prepolymer; and
the surface asperities have a storage modulus (E′) at 25 degrees C. greater than about 1000 MPa and a Shore D hardness at 25 degrees C. greater than about 70.

26. The polishing pad of claim 25 , wherein the surface asperities have a tensile toughness at 25 degrees C. greater than about 50 MPa.

27. The polishing pad of claim 15 , wherein the thermosetting polyurethane polishing layer further comprises a sufficient quantity of hollow microspheres such that the thermosetting polyurethane polishing layer has a porosity in a range from about 10 to about 50 percent.

28. The polishing pad of claim 15 , wherein:
the prepolymer is an aromatic prepolymer selected from the group consisting of 75D prepolymers, 80D prepolymers, and mixtures thereof;
the polyamine curative is an aromatic diamine curative selected from the group consisting of 4,4-methylenebis(2chloroaniline), dimethylthiotoluenediamine, and mixtures thereof; and
the curative mixture comprises from about 10 to about 40 weight percent of the cyclohexanedimethanol curative.

29. The polishing pad of claim 15 , wherein the thermosetting polyurethane polishing layer is adhered to a sub-pad.

Assignees

• Cabot Microelectronics Corp
• Cmc Mat Inc

Inventors

• Ma Rui
• Fu Lin
• Tsai Chen-Chih
• Lee Jaeseok
• Brosnan Sarah

Classifications

• B24B37/24 Primary

  characterised by the composition or properties of the pad materials · CPC title

• B24B37/26

  characterised by the shape of the lapping pad surface, e.g. grooved · CPC title

• B24D11/00

  Constructional features of flexible abrasive materials; Special features in the manufacture of such materials · CPC title

• B24D13/14

  acting by the front face · CPC title

• B24D3/32

  for porous or cellular structure · CPC title