IP Library Granted Patent US 12,122,013
Granted Patent B2
US 12,122,013 · App. 17/077,360 · Granted Oct 22, 2024

Composition for polishing pad and polishing pad

Inventors: Jong Wook Yun (Gyeonggi-do, KR); Jang Won Seo (Gyeonggi-do, KR); Hyeyoung Heo (Gyeonggi-do, KR); Eun Sun Joeng (Gyeonggi-do, KR)
Assignee: SK ENPULSE CO., LTD.
B24B37/24B24B37/22B24B37/26C08G18/10C08G18/72C08G18/3203C08K5/12C08K5/18
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Quick Facts
Patent No.
US 12,122,013
App. No.
17/077,360
Granted
Oct 22, 2024
Kind
B2
Abstract

The composition according to an embodiment employs a mixture of curing agents, which comprises a first curing agent containing sulfur and a second curing agent containing an ester group, whereby it is possible to control the physical properties of the polishing pad as necessary.

Claims (33)

1. A composition for a polishing pad, which comprises a urethane-based prepolymer and a mixture of curing agents, wherein the mixture of curing agents comprises a first curing agent containing sulfur and a second curing agent containing an ester group,

wherein a weight ratio of the first curing to the second curing agent is 1:0.1 to 0.9, and

wherein the content of the first curing agent is 11 parts by weight to 18 parts by weight based on 100 parts by weight of the composition, and the content of the second curing agent is 1 part by weight to 10 parts by weight based on 100 parts by weight of the composition.

2. The composition for a polishing pad of claim 1 , wherein the first curing agent comprises at least one selected from the group consisting of 3,5-dimethylthio-2,6-diaminotoluene, 2,6-bis(methylthio)-4-methyl-1,3-benzenediamine, molybdenum sulfide, niobium sulfide, talc, tantalum sulfide, and tungsten disulfide.

3. The composition for a polishing pad of claim 1 , wherein the second curing agent comprises at least one selected from the group consisting of compounds represented by the following Formulae 1 to 3:

in Formula 1, L 1 is at least one selected from a linear or branched alkylene group having 1 to 20 carbon atoms, a linear or branched heteroalkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkylene group having 5 to 30 carbon atoms, a substituted or unsubstituted arylene group having 5 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5 to 30 carbon atoms,

in Formula 2, L 2 is at least one selected from a linear or branched alkylene group having 1 to 20 carbon atoms, a linear or branched heteroalkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkylene group having 5 to 30 carbon atoms, a substituted or unsubstituted arylene group having 5 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5 to 30 carbon atoms,

R 1 and R 2 are each independently at least one selected from a linear or branched alkyl group having 1 to 20 carbon atoms, a linear or branched heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms, and

in Formula 3, R 3 is at least one selected from a linear or branched alkyl group having 1 to 20 carbon atoms, a linear or branched heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms.

4. The composition for a polishing pad of claim 3 , wherein the second curing agent comprises at least one selected from the group consisting of 1,3-propanediol bis(4-aminobenzoate) (PDPAB), 4-(4-aminobenzoyl)oxyphenyl 4-aminobenzoate, 4-(4-aminobenzoyl)oxybutyl 4-aminobenzoate, 4-[4-(4-aminobenzoyl)oxy-3-methylbutoxy]butyl 4-aminobenzoate, methylene bis-methylanthranilate (MBNA), and isobutyl 3,5-diamino-4-chlorobenzoate (BDACB).

5. The composition for a polishing pad of claim 1 , which, upon curing, has a modulus of 50 MPa to 120 MPa and an elongation of 90% to 200%,

a hardness of 50 Shore D to 60 Shore D at 30° C.,

a hardness of 50 Shore D to 58 Shore D at 50° C.,

a hardness of 40 Shore D to 55 Shore D at 70° C., and

the number of surface defects of a semiconductor substrate of 10 or less at a temperature of 50 to 60° C.

6. A composition for a polishing pad, which comprises a urethane-based prepolymer and a mixture of curing agents, wherein the mixture of curing agents comprises a first curing agent containing sulfur and a second curing agent containing an ester group,

wherein the first curing agent is a liquid curing agent containing sulfur, the second curing agent is a solid curing agent containing an ester group and two or more benzene rings, and the content of the solid curing agent is equal to, or greater than, the content of the liquid curing agent based on the weight,

wherein, upon curing, the composition has a storage modulus of 2.3×10 8 Pa or more at a temperature of 60 to 80° C., and a rate of reduction in the storage modulus with respect to a temperature change of 50° C. to 100° C. of 77% or less,

wherein the content of the liquid curing agent is 5 parts by weight to 30 parts by weight based on 100 parts by weight of the composition, and the content of the solid curing agent is 8.5 parts by weight to 35 parts by weight based on 100 parts by weight of the composition.

7. The composition for a polishing pad of claim 6 , wherein the content ratio of the solid curing agent and the liquid curing agent is 1:0.1 to 1 as a weight ratio.

8. The composition for a polishing pad of claim 6 , wherein the solid curing agent has a melting point (m.p.) of 100° C. to 150° C.

9. The composition of for a polishing pad claim 8 , wherein the solid curing agent comprises at least one selected from the group consisting of compounds represented by the following Formulae 1 and 2:

in Formula 1, L 1 is at least one selected from a linear or branched alkylene group having 1 to 20 carbon atoms, a linear or branched heteroalkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkylene group having 5 to 30 carbon atoms, a substituted or unsubstituted arylene group having 5 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5 to 30 carbon atoms,

in Formula 2, L 2 is at least one selected from a linear or branched alkylene group having 1 to 20 carbon atoms, a linear or branched heteroalkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkylene group having 5 to 30 carbon atoms, a substituted or unsubstituted arylene group having 5 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5 to 30 carbon atoms, and

R 1 and R 2 are each independently at least one selected from a linear or branched alkyl group having 1 to 20 carbon atoms, a linear or branched heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms.

10. The composition for a polishing pad of claim 9 , wherein the solid curing agent comprises at least one selected from the group consisting of 1,3-propanediol bis(4-aminobenzoate) (PDPAB), 4-(4-aminobenzoyl)oxyphenyl 4-aminobenzoate, 4-(4-aminobenzoyl)oxybutyl 4-aminobenzoate, 4-[4-(4-aminobenzoyl)oxy-3-methylbutoxy]butyl 4-aminobenzoate, and methylene bis-methylanthranilate (MBNA).

11. The composition for a polishing pad of claim 6 , which, upon curing, has a rate of change in a polishing rate with respect to a temperature change of 50° C. to 60° C. of 2% or less.

12. The composition for a polishing pad of claim 6 , wherein the liquid curing agent has a boiling point (b.p.) of 160° C. to 240° C., and the liquid curing agent comprises at least one selected from the group consisting of 3,5-dimethylthio-2,6-diaminotoluene and 2,6-bis(methylthio)-4-methyl-1,3-benzenediamine.

13. The composition for a polishing pad of claim 6 , which, upon curing, has a modulus of 63 MPa to 100 MPa and a tensile strength of 21 N/mm 2 to 23 N/mm 2 ,

a hardness of 50 Shore D to 60 Shore D at 30° C.,

a hardness of 50 Shore D to 58 Shore D at 50° C.,

a hardness of 40 Shore D to 55 Shore D at 70° C., and

a hardness difference between 30° C. and 70° C. of 5 Shore D to 15 Shore D.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 2, 2025
From: SK ENPULSE CO., LTD.
To: ENPULSE CO., LTD.
Reel/Frame 071277/0667 →
CHANGE OF NAME Recorded Feb 13, 2023
From: SKC SOLMICS CO., LTD.
To: SK ENPULSE CO., LTD.
Reel/Frame 062717/0084 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 23, 2021
From: SKC CO., LTD.
To: SKC SOLMICS CO., LTD.
Reel/Frame 055685/0677 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 22, 2020
From: YUN, JONG WOOK; SEO, JANG WON; HEO, HYEYOUNG; JOENG, EUN SUN
To: SKC CO., LTD.
Reel/Frame 054138/0619 →
Priority Claims (2)
KR 10-2019-0132512 · Oct 23, 2019 · national
KR 10-2019-0149599 · Nov 20, 2019 · national
Continuity (1)
Related Publication 20210122007A1 · Apr 29, 2021