IP Library Granted Patent US 7,238,653
Granted Patent B2
US 7,238,653 · App. 10/723,029 · Granted Jul 3, 2007

Cleaning solution for photoresist and method for forming pattern using the same

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Quick Facts
Patent No.
US 7,238,653
App. No.
10/723,029
Granted
Jul 3, 2007
Kind
B2
Abstract

Cleaning solutions for photoresist are disclosed which are useful for cleaning a semiconductor substrate in the last step of development when photoresist patterns are formed. Also, methods for forming photoresist patterns using the same are disclosed. The disclosed cleaning solution comprises H 2 O as a solution, a surfactant which is phosphate-alcoholamine salt represented by Formula 1, and an alcohol compound. The disclosed cleaning solution has lower surface tension than that of distilled water which has been used for conventional cleaning solutions, thereby improving resistance to photoresist pattern collapse and stabilizing the photoresist pattern formation. wherein R, x, y, z, a and b are as defined in the specification.

Claims (47)

1. A cleaning solution for photoresist patterns comprising:

H 2 O as a solvent; and

a compound represented by following Formula 1 as a surfactant:

wherein

R is C 2 -C 20 alkyl or C 6 -C 25 alkyl aryl;

x, y and z individually are an integer ranging from 0 to 10;

a is 2 or 3; and

b is an integer ranging from 2 to 50.

2. The cleaning solution according to claim 1 , wherein the b is an integer ranging from 6 to 11.

3. The cleaning solution according to claim 1 , further comprising an alcohol.

4. The cleaning solution according to claim 1 , wherein the compound of Formula 1 is present in an amount ranging from 0.001 to 2 wt % based on the total weight of said solution.

5. The cleaning solution according to claim 3 wherein the alcohol is present in an amount ranging from 0 to 20 wt % based on the total weight of said solution.

6. The cleaning solution according to claim 1 wherein the compound of Formula 1 is represented by Formula 2 or Formula 3:

wherein

R is C 2 -C 20 alkyl or C 6 -C 25 alkyl aryl;

x, y and z individually are an integer ranging from 0 to 10; and

n is an integer ranging from 1 to 49.

7. The cleaning solution according claim 6 , wherein the compound of Formula 2 is present in an amount ranging from 0.001 to 2 wt % based on the total weight of said solution, and the alcohol is present in an amount ranging from 0 to 20 wt % based on the total weight of said solution.

8. The cleaning solution according to claim 6 , wherein the compound of Formula 3 is present in an amount ranging from 0.001 to 2 wt % based on the total weight of said solution, and the alcohol is present in an amount ranging from 0 to 10 wt % based on the total weight of said solution.

9. The cleaning solution according to claim 7 , wherein the compound of Formula 2 is present in an amount ranging from 0.01 to 1 wt % based on the total weight of said solution, and the alcohol is present in an amount ranging from 0.01 to 10 wt % based on the total weight of said solution.

10. The cleaning solution according to claim 8 , wherein the compound of Formula 3 is present in an amount ranging from 0.001 to 1 wt % based on the total weight of said solution, and the alcohol is present in an amount ranging from 0.001 to 5 wt % based on the total weight of said solution.

11. The cleaning solution according to claim 6 , wherein R is selected from the group consisting of octyl, octyl phenyl, nonyl, nonyl phenyl, decyl, decyl phenyl, undecyl, undecyl phenyl, dodoecyl and dodecyl phenyl, and n is an integer ranging from 5 to 10.

12. The cleaning solution according to claim 3 , wherein the alcohol is selected from the group consisting of C 1 -C 10 alkyl alcohol, C 1 -C 10 alkoxyalkyl alcohol, and mixtures thereof.

13. The cleaning solution according to claim 12 , wherein the C 1 -C 10 alkyl alcohol is selected from the group consisting of methanol, ethanol, propanol, isopropanol, n-butanol, sec-butanol, t-butanol, 1-pentanol, 2-pentanol, 3-pentanol, 2,2-dimethyl-1-propanol and mixtures thereof.

14. The cleaning solution according to claim 12 , wherein the C 1 -C 10 alkoxyalkyl alcohol is selected from the group consisting of 2-methoxyethanol, 2-(2-methoxyethoxy)ethanol, 1-methox-2-propanol, 3-methoxy-1,2-propandiol and mixtures thereof.

15. The cleaning solution according to claim 1 , wherein the solution is selected from the group consisting of

mixture comprising the compound of Formula 2 as a surfactant wherein R is nonyl; x, y and z are 1, respectively; and n is 7, methanol as an alcohol and water as a solvent;

mixture comprising the compound of Formula 2 as a surfactant wherein R is octyl; x, y and z are 1, respectively; and n is 7, methanol as an alcohol and water as a solvent;

mixture comprising the compound of Formula 2 as a surfactant wherein R is dodecyl; x, y and z are 0, respectively; and n is 7, isopropanol as an alcohol and water as a solvent;

mixture comprising the compound of Formula 2 as a surfactant wherein R is octyl phenyl; x, y and z are 1, respectively; and n is 3, isopropanol as an alcohol and water as a solvent;

mixture comprising the compound of Formula 3 as a surfactant wherein R is nonyl; x, y and z are 1, respectively; and n is 7, methanol as an alcohol and water as a solvent;

mixture comprising the compound of Formula 3 as a surfactant wherein R is octyl; x, y and z are 1, respectively; and n is 7, methanol as an alcohol and water as a solvent;

mixture comprising the compound of Formula 3 as a surfactant wherein R is dodecyl; x, y and z are 0, respectively; and n is 7, isopropanol as an alcohol and water as a solvent; and

mixture comprising the compound of Formula 3 as a surfactant wherein R is octyl phenyl; x, y and z are 1, respectively; and n is 3, isopropanol as an alcohol and water as a solvent.

16. The cleaning solution according to claim 15 , wherein the surfactant of Formula 2 is present in an amount ranging from 0.001 to 2 wt % based on the total weight of said mixture, and the alcohol is present in an amount ranging from 0 to 20 wt % based on the total weight of said mixture.

17. The cleaning solution according to claim 15 , wherein the surfactant of Formula 3 is present in an amount ranging from 0.001 to 2 wt % based on the total weight of said mixture, and the alcohol is present in an amount ranging from 0 to 10 wt % based on the total weight of said mixture.

18. The cleaning solution according to claim 16 , wherein the surfactant of Formula 2 is present in an amount ranging from 0.01 to 1 wt % based on the total weight of said mixture, and the alcohol is present in an amount ranging from 0.01 to 10 wt % based on the total weight of said mixture.

19. The cleaning solution according to claim 17 , wherein the surfactant of Formula 3 is present in an amount ranging from 0.001 to 1 wt % based on the total weight of said mixture, and the alcohol is present in an amount ranging from 0.001 to 5 wt % based on the total weight of said mixture.

20. A method for forming a photoresist pattern, comprising:

(a) preparing a semiconductor substrate on which an underlying layer is formed;

(b) coating a photoresist on the underlying layer to form a photoresist film;

(c) exposing the photoresist film to light;

(d) developing the exposed photoresist film; and

(e) cleaning the resulting structure using the cleaning solution of claim 1 .

21. The method according to claim 20 , further comprising soft baking step before part (c) or post baking step after part (c).

22. The method according to claim 20 , wherein the source of the light is selected from the group consisting of KrF (248 nm), ArF (193 nm), VUV (157 nm), EUV (13 nm), E-beam, X-ray and ion-beam.

23. A semiconductor device manufactured by the method of claim 20 .

Assignments (4)
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE IS HYNIX SEMICONDUCTOR INC. NOT HYNIX-SEMICONDUCTOR INC. THERE IS NO HYPHEN IN THE NAME. PREVIOUSLY RECORDED ON REEL 67328 FRAME 814. ASSIGNOR(S) HEREBY CONFIRMS THE CHANGE OF NAME. Recorded May 14, 2024
From: HYNIX SEMICONDUCTOR INC.
To: SK HYNIX INC.
Reel/Frame 067412/0482 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 9, 2024
From: SK HYNIX INC.
To: MIMIRIP LLC
Reel/Frame 067369/0832 →
CHANGE OF NAME Recorded May 6, 2024
From: HYNIX-SEMICONDUCTOR INC.
To: SK HYNIX INC.
Reel/Frame 067328/0814 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 8, 2004
From: LEE, GEUN SU; BOK, CHEOL KYU; HWANG, YOUNG SUN; LEE, SUNG KOO; MOON, SEUNG CHAN; SHIN, KI SOO
To: HYNIX SEMICONDUCTOR INC.
Reel/Frame 015046/0052 →