IP Library Granted Patent US 10,908,505
Granted Patent B2
US 10,908,505 · App. 16/101,883 · Granted Feb 2, 2021

Photoresist developer composition and manufacturing method of semiconductor package using the same

Inventors: Sang Hyun Kwon (Suwon-Si, KR); Jin Hee Hwang (Suwon-Si, KR); Seong Chan Park (Suwon-Si, KR); Young Ju Lee (Suwon-si, KR)
Assignee: SAMSUNG ELECTRONICS CO., LTD.
G03F7/327G03F7/322
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 10,908,505
App. No.
16/101,883
Granted
Feb 2, 2021
Kind
B2
Abstract

A photoresist developer composition contains: a quaternary alkyl ammonium compound; and a corrosion inhibitor. The corrosion inhibitor contains a silane-based compound and an azole-based compound A manufacturing method of a semiconductor package includes using the photoresist developer composition.

Claims (51)

1. A photoresist developer composition comprising:

2 to 4 wt % a quaternary alkyl ammonium compound;

1.5 to 3 wt % of a silane-based compound; and

0.1 to 2 wt % of an azole-based compound,

wherein a content of the silane-based compound is greater than a content of the azole-based compound.

2. The photoresist developer composition of claim 1 , wherein the quaternary alkyl ammonium compound includes tetraalkyl ammonium hydroxide.

3. The photoresist developer composition of claim 1 , wherein the silane-based compound is an alkoxy silane-based compound.

4. The photoresist developer composition of claim 3 , wherein the silane-based compound is at least one compound selected from the group consisting of compounds represented by the following [Chemical Formula 1] to [Chemical Formula 4]:

in [Chemical Formula 1],

R 1 is a substituted or unsubstituted (C 1 to C 10 ) aliphatic chain,

R 2 to R 4 are each independently a substituted or unsubstituted (C 1 to C 10 ) aliphatic chain, a substituted or unsubstituted (C 1 to C 10 ) aliphatic ring, a substituted or unsubstituted (C 6 to C 20 ) aromatic ring, or a combination thereof, and

R 5 is hydrogen, a substituted or unsubstituted (C 1 to C 10 ) aliphatic chain, a substituted or unsubstituted (C 1 to C 10 ) aliphatic ring, a substituted or unsubstituted (C 6 to C 20 ) aromatic ring, or a combination thereof,

in [Chemical Formula 2],

R 6 to R 9 are each independently a substituted or unsubstituted (C 1 to C 10 ) aliphatic chain, a substituted or unsubstituted (C 1 to C 10 ) aliphatic ring, a substituted or unsubstituted (C 6 to C 20 ) aromatic ring, or a combination thereof,

in [Chemical Formula 3],

R 10 is a substituted or unsubstituted (C 1 to C 10 ) aliphatic chain, and

R 11 to R 13 are each independently a substituted or unsubstituted (C 1 to C 10 ) aliphatic chain, a substituted or unsubstituted (C 1 to C 10 ) aliphatic ring, a substituted or unsubstituted (C 6 to C 20 ) aromatic ring, or a combination thereof, and

in [Chemical Formula 4],

R 14 and R 15 are each independently a substituted or unsubstituted (C 1 to C 10 ) aliphatic chain, a substituted or unsubstituted (C 1 to C 10 ) aliphatic ring, a substituted or unsubstituted (C 6 to C 20 ) aromatic ring, or a combination thereof.

5. The photoresist developer composition of claim 1 , wherein the azole-based compound is at least one compound selected from the group consisting of a benzotriazole-based compound, a benzothiazole-based compound, and a pyrazole-based compound.

6. The photoresist developer composition of claim 5 , wherein the azole-based compound is at least one compound selected from the group consisting of compounds represented by [Chemical Formula 5] to [Chemical Formula 8]:

in [Chemical Formula 5],

R 16 is hydrogen, a substituted or unsubstituted (C 1 to C 10 ) aliphatic chain, a substituted or unsubstituted (C 1 to C 10 ) aliphatic ring, a substituted or unsubstituted (C 6 to C 20 ) aromatic ring, or a combination thereof,

in [Chemical Formula 6],

R 17 is hydrogen, a substituted or unsubstituted (C 1 to C 10 ) aliphatic chain, a substituted or unsubstituted (C 1 to C 10 ) aliphatic ring, a substituted or unsubstituted (C 6 to C 20 ) aromatic ring, or a combination thereof,

in [Chemical Formula 7],

R 18 is hydrogen, a substituted or unsubstituted (C 1 to C 10 ) aliphatic chain, a substituted or unsubstituted (C 1 to C 10 ) aliphatic ring, a substituted or unsubstituted (C 6 to C 20 ) aromatic ring, or a combination thereof, and

in [Chemical Formula 8],

R 19 is hydrogen, a substituted or unsubstituted (C 1 to C 10 ) aliphatic chain, a substituted or unsubstituted (C 1 to C 10 ) aliphatic ring, a substituted or unsubstituted (C 6 to C 20 ) aromatic ring, or a combination thereof.

7. The photoresist developer composition of claim 1 , further comprising a solvent.

8. The photoresist developer composition of claim 7 , wherein the solvent is contained in a content of 0.5 to 3 wt %.

9. The photoresist developer composition of claim 7 , wherein the solvent includes at least one selected from the group consisting of N-methyl-2-pyrrolidone and isopropyl alcohol.

10. The photoresist developer composition of claim 1 , further comprising a surfactant.

11. The photoresist developer composition of claim 10 , wherein the surfactant is contained in a content of 0.01 to 1 wt %.

12. The photoresist developer composition of claim 10 , wherein the surfactant is polyalkylene glycol alkyl ether.

13. The photoresist developer composition of claim 12 , wherein the surfactant is a compound represented by the following [Chemical Formula 9]:

R 20 OR 21 n OR 22   [Chemical Formula 9]

in [Chemical Formula 9],

R 20 to R 22 are each independently a substituted or unsubstituted (C 1 to C 10 ) aliphatic chain, and

n is an integer of 10 to 30.

14. The photoresist developer composition of claim 1 , wherein a pH of the photoresist developer composition is 12 to 14.

15. The photoresist developer composition of claim 1 , wherein the azole-based compound is at least one compound represented by the following [Chemical Formula 5]:

wherein, in [Chemical Formula 5], R 16 is hydrogen, a substituted or unsubstituted (C 1 to C 10 ) aliphatic chain, a substituted or unsubstituted (C 1 to C 10 ) aliphatic ring, a substituted or unsubstituted (C 6 to C 20 ) aromatic ring, or a combination thereof.

16. The photoresist developer composition of claim 1 , wherein the silane-based compound is represented by the following [Chemical Formula 2]:

wherein, in [Chemical Formula 2], R 6 to R 9 are each independently a substituted or unsubstituted (C 1 to C 10 ) aliphatic chain, a substituted or unsubstituted (C 1 to C 10 ) aliphatic ring, a substituted or unsubstituted (C 6 to C 20 ) aromatic ring, or a combination thereof.

17. The photoresist developer composition of claim 15 , wherein the silane-based compound is represented by the following [Chemical Formula 2]:

wherein, in [Chemical Formula 2], R 6 to R 9 are each independently a substituted or unsubstituted (C 1 to C 10 ) aliphatic chain, a substituted or unsubstituted (C 1 to C 10 ) aliphatic ring, a substituted or unsubstituted (C 6 to C 20 ) aromatic ring, or a combination thereof.

18. A manufacturing method of a semiconductor package, the manufacturing method comprising:

preparing a semiconductor chip having an active surface on which connection pads are disposed and an inactive surface opposing the active surface;

forming a photoresist on the active surface of the semiconductor chip and exposing the photoresist; and

developing the photoresist by applying the photoresist developer composition according to claim 1 to the exposed photoresist.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 3, 2019
From: SAMSUNG ELECTRO-MECHANICS CO., LTD.
To: SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 049350/0756 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 13, 2018
From: KWON, SANG HYUN; HWANG, JIN HEE; PARK, SEONG CHAN; LEE, YOUNG JU
To: SAMSUNG ELECTRO-MECHANICS CO., LTD.
Reel/Frame 046627/0555 →
Priority Claims (1)
KR 10-2018-0000412 · Jan 2, 2018 · national
Continuity (1)
Related Publication 20190204746A1 · Jul 4, 2019