IP Library Granted Patent US 7,563,559
Granted Patent B2
US 7,563,559 · App. 11/772,998 · Granted Jul 21, 2009

Photoresist formulation for high aspect ratio plating

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Quick Facts
Patent No.
US 7,563,559
App. No.
11/772,998
Granted
Jul 21, 2009
Kind
B2
Abstract

SU-8 photoresist compositions are modified to improve their adhesion properties by adding 1% to 6% of an adhesion promoter selected from the group consisting of glycidoxypropanetrimethoxysilane, mercaptopropyltrimethoxysilane, and aminopropyltrimethoxysilane. SU-8 photoresist compositions are modified to improve their resistance to cracking and film stress by adding 0.5% to 3% of a plasticizer selected from the group consisting of dialkylphthalates, dialkylmalonates, dialkylsebacates, dialkyladipates, and diglycidyl hexahydrophthalates. The improvements can be obtained simultaneously by adding both the adhesion promoter and the plasticizer to SU-8 photoresist compositions.

Claims (50)

1. A method of making a photoresist masking composition, the method comprising:

providing an organic solvent;

dissolving an octafunctional epoxidized novolac resin in the solvent to form a solution;

adding to the solution a plasticizer selected from the group consisting of dialkylphthalates, dialkylmalonates, dialkylsebacates, and dialkyladipates;

adding to the solution a photopolymerization initiator; and

adding to the solution an adhesion promoter selected from the group consisting of glycidoxypropanetrimethoxysilane, mercaptopropyltrimethoxysilane, and aminopropyltrimethoxysilane.

2. The method of claim 1 , wherein said plasticizer is a dialkylphthalates.

3. The method of claim 1 , wherein said plasticizer is a dialkylmalonates.

4. The method of claim 1 , wherein said plasticizer is a dialkylsebacates.

5. The method of claim 1 , wherein said plasticizer is a dialkyladipates.

6. The method of claim 1 , wherein said adhesion promoter is a glycidoxypropanetrimethoxysilane.

7. The method of claim 1 , wherein said adhesion promoter is a mercaptopropyltrimethoxysilane.

8. The method of claim 1 , wherein said adhesion promoter is a aminopropyltrimethoxysilane.

9. The method of claim 1 , wherein said octafunctional epoxidized novolac resin is of the formula:

10. The method of claim 1 , wherein said solvent is present in an amount ranging between about 15% and about 45% by weight.

11. The method of claim 1 , wherein said solvent is present in an amount ranging between about 20% and about 30% by weight.

12. The method of claim 1 , wherein said solvent is present in an amount of about 25% by weight.

13. The method of claim 1 , wherein said photopolymerization initiator is present in an amount ranging between about 3% and about 10% by weight.

14. The method of claim 1 , wherein said photopolymerization initiator is present in an amount ranging between about 5% and about 8% by weight.

15. The method of claim 1 , wherein said photopolymerization initiator is present in an amount ranging between about 6% and about 7% by weight.

16. The method of claim 1 , wherein said photopolymerization initiator is a triaryl suiphonium SbF 6 salt.

17. The method of claim 1 , wherein said plasticizer is present in an amount ranging between about 0.5% and about 3% by weight.

18. The method of claim 1 , wherein said plasticizer is present in an amount of about 2% by weight.

19. The method of claim 1 , wherein said adhesion promoter is present in an amount ranging between about 1% and about 6% by weight.

20. The method of claim 1 , wherein said adhesion promoter is present in an amount ranging between about 3% and about 4% by weight.

21. The method of claim 1 , further comprising mixing the solution to substantially achieve uniformity.

22. The method of claim 1 , wherein the steps of providing the solvent, dissolving the resin in the solvent, adding the plasticizer, adding the initiator, and adding the adhesion promoter are performed in that order.

23. The method of claim 1 , wherein the initiator is added to the solution separately from the plasticizer.

24. The method of claim 1 , wherein the solution is immediately mixed after the adhesion promoter is added.

25. The method of claim 1 , further comprising debubbling the solution.

26. A method of making a photoresist masking composition, the method comprising:

providing an organic solvent having a boiling point of between 160° C. and 260° C.;

dissolving an octafunctional epoxidized novolac resin in the solvent to form a solution;

adding to the solution a plasticizer selected from the group dialkylphthalates, dialkylmalonates, dialkylsebacates, dialkyladipates, and diglycidyl hexahydrophthalates;

adding to the solution a photopolymerization initiator; and

adding to the solution an adhesion promoter selected from the group consisting of glycidoxypropanetrimethoxysilane, mercaptopropyltrimethoxysilane, and aminopropyltrimethoxysilane.

27. The method of claim 26 , wherein said solvent has a boiling point of between 190° C. and 220° C.

28. A photoresist masking material according to claim 26 wherein said solvent has a boiling point of between 200° C. and 210° C.

29. A method of making a photoresist masking composition, the method comprising:

providing an organic solvent comprising gamma butyrolactone;

dissolving an octafunctional epoxidized novolac resin in the solvent to form a solution;

adding to the solution a plasticizer selected from the group dialkylphthalates, dialkylmalonates, dialkylsebacates, dialkyladipates, and diglycidyl hexahydrophthalates;

adding to the solution a photopolymerization initiator; and

adding to the solution an adhesion promoter selected from the group consisting of glycidoxypropanetrimethoxysilane, mercaptopropyltrimethoxysilane, and aminopropyltrimethoxysilane.

30. A method of making a photoresist masking composition, the method comprising:

providing 15% to 45% by weight of an organic solvent;

dissolving an octafunctional epoxidized novolac resin in the solvent to form a solution, the resin being 50% to 75% by weight and of the formula:

adding to the solution 0.5% to 3% by weight of a plasticizer selected from the group consisting of dialkylphthalates, dialkylmalonates, dialkylsebacates, and dialkyladipates;

adding to the solution 3% to 7% by weight a photopolymerization initiator; and

adding to the solution 1% to 6% by weight of an adhesion promoter selected from the group consisting of glycidoxypropanetrimethoxysilane, mercaptopropyltrimethoxysilane, and aminopropyltrimethoxysilane.

Assignments (2)
RELEASE OF SECURITY INTEREST Recorded Aug 7, 2025
From: HSBC BANK USA, NATIONAL ASSOCIATION
To: FORMFACTOR, INC.
Reel/Frame 072853/0001 →
SECURITY INTEREST IN UNITED STATES PATENTS AND TRADEMARKS Recorded Jul 12, 2016
From: FORMFACTOR, INC.; ASTRIA SEMICONDUCTOR HOLDINGS, INC.; CASCADE MICROTECH, INC.; MICRO-PROBE INCORPORATED
To: HSBC BANK USA, NATIONAL ASSOCIATION
Reel/Frame 039184/0280 →