IP Library Granted Patent US 7,238,464
Granted Patent B2
US 7,238,464 · App. 11/362,695 · Granted Jul 3, 2007

Photoresist formulation for high aspect ratio plating

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 7,238,464
App. No.
11/362,695
Granted
Jul 3, 2007
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 (60)

1. A method comprising:

providing a photoresist material, the photo resist material comprising:

an octafunctional epoxidized novolac resin;

an organic solvent;

a photopolymerization initiator;

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

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

depositing the photoresist material on a substrate;

selectively exposing the deposited photoresist material to radiated energy, one or more portions of the photoresist being hardened and one or more portions of the photoresist being unhardened; and

removing the one or more unhardened portions of the photoresist material from the substrate.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

21. The method of claim 1 , wherein:

the substrate comprises copper or a wafer; and

the radiated energy comprises optical radiation, electromagnetic radiation, ultraviolet radiation, or near ultraviolet radiation.

22. A method comprising:

providing a photoresist material, the photo resist material comprising:

an octafunctional epoxidized novolac resin;

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

a photopolymerization initiator;

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

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

depositing the photoresist material on a substrate;

selectively exposing the deposited photoresist material to radiated energy, one or more portions of the photoresist being hardened and one or more portions of the photoresist being unhardened; and

removing the one or more unhardened portions of the photoresist material from the substrate.

23. The method of claim 22 , wherein the solvent has a boiling point of between 190° C. and 220° C.

24. The method of claim 22 , wherein the solvent has a boiling point of between 200° C. and 210° C.

25. The method of claim 22 , wherein:

the substrate comprises copper or a wafer; and

the radiated energy comprises optical radiation, electromagnetic radiation, ultraviolet radiation, or near ultraviolet radiation.

26. A method comprising:

providing a photoresist material, the photo resist material comprising:

an octafunctional epoxidized novolac resin;

an organic solvent comprising gamma butyrolactone;

a photopolymerization initiator;

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

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

depositing the photoresist material on a substrate;

selectively exposing the deposited photoresist material to radiated energy, one or more portions of the photoresist being hardened and one or more portions of the photoresist being unhardened; and

removing the one or more unhardened portions of the photoresist material from the substrate.

27. The method of claim 26 , wherein:

the substrate comprises copper or a wafer; and

the radiated energy comprises optical radiation, electromagnetic radiation, ultraviolet radiation, or near ultraviolet radiation.

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 →