IP Library Granted Patent US 7,005,233
Granted Patent B2
US 7,005,233 · App. 10/853,858 · Granted Feb 28, 2006

Photoresist formulation for high aspect ratio plating

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Quick Facts
Patent No.
US 7,005,233
App. No.
10/853,858
Granted
Feb 28, 2006
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 (54)

1. A photoresist masking material, comprising:

a) an octafunctional epoxidized novolac resin;

b) an organic solvent;

c) a photopolymerization initiator;

d) a plasticizer selected from the group consisting of dialkylphthalates, dialkylmalonates, dialkylsebacates, and dialkyladipates; and

e) an adhesion promoter selected from the group consisting of glycidoxypropanetrimethoxysilane, mercaptopropyltrimethoxysilane, and aminopropyltrimethoxysilane.

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

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

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

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

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

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

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

9. A photoresist masking material according to claim 1 wherein said octafunctional epoxidized novolac resin is of the formula:

10. A photoresist masking material according to claim 1 wherein said solvent is present in an amount ranging between about 15% and about 45% by weight.

11. A photoresist masking material according to claim 1 wherein said solvent is present in an amount ranging between about 20% and about 30% by weight.

12. A photoresist masking material according to claim 1 wherein said solvent is present in an amount of about 25% by weight.

13. A photoresist masking material according to claim 1 wherein said photopolymerization initiator is present in an amount ranging between about 3% and about 10% by weight.

14. A photoresist masking material according to claim 1 wherein said photopolymerization initiator is present in an amount ranging between about 5% and about 8% by weight.

15. A photoresist masking material according to claim 1 wherein said photopolymerization initiator is present in an amount ranging between about 6% and about 7% by weight.

16. A photoresist masking material according to claim 1 wherein said photopolymerization initiator is a triaryl sulphonium SbF 6 salt.

17. A photoresist masking material according to claim 1 wherein said plasticizer is present in an amount ranging between about 0.5% and about 3% by weight.

18. A photoresist masking material according to claim 1 wherein said plasticizer is present in an amount of about 2% by weight.

19. A photoresist masking material according to claim 1 wherein said adhesion promoter is present in an amount ranging between about 1% and about 6% by weight.

20. A photoresist masking material according to claim 1 wherein said adhesion promoter is present in an amount ranging between about 3% and about 4% by weight.

21. A photoresist masking material, comprising:

a) an octafunctional epoxidized novolac resin;

b) an organic solvent;

c) a photopolymerization initiator;

d) a plasticizer selected from the group consisting of dialkylphthalates, dialkylmalonates, dialkylsebacates, dialkyladipates, and diglycidyl hexahydrophthalates; and

e) an adhesion promoter selected from the group consisting of glycidoxypropanetrimethoxysilane, mercaptopropyltrimethoxysilane, and aminopropyltrimethoxysilane,

wherein said solvent has a boiling point of between 160° C. and 260° C.

22. A photoresist masking material according to claim 21 wherein said solvent has a boiling point of between 190° C. and 220° C.

23. A photoresist masking material according to claim 21 wherein said solvent has a boiling point of between 200° C. and 210° C.

24. A photoresist masking material, comprising:

a) an octafunctional epoxidized novolac resin;

b) an organic solvent;

c) a photopolymerization initiator;

d) a plasticizer selected from the group consisting of dialkylphthalates, dialkylmalonates, dialkylsebacates, dialkyladipates, and diglycidyl hexahydrophthalates; and

e) an adhesion promoter selected from the group consisting of glycidoxypropanetrimethoxysilane, mercaptopropyltrimethoxysilane, and aminopropyltrimethoxysilane,

herein said solvent is gamma butyrolactone.

25. A photoresist masking material, comprising:

a) 50% to 75% by weight of an octafunctional epoxidized novolac resin of the formula:

b) 15% to 45% by weight of an organic solvent;

c) 3% to 7% by weight a photopolymerization initiator;

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

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

26. A method of improving resistance to cracking and film stress of a negative photoresist masking composition comprising an octofunctional epoxidized novolac resin of the formula

an organic solvent, and a photopolymerization initiator, said method comprising:

adding to the photoresist masking composition 0.5% to 3% by weight of a plasticizer selected from the group consisting of dioctylphthalates, dialkylmalonates, dialkylsebacates, and dialkyladipates.

27. The photoresist of claim 26 , wherein said plasticizer is a dialkylphthalates.

28. The photoresist of claim 26 , wherein said plasticizer is a dialkylmalonates.

29. The photoresist of claim 26 , wherein said plasticizer is a dialkylsebacates.

30. The photoresist of claim 26 , wherein said plasticizer is a dialkyladipates.

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 →