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

• US 7,238,653 B2
• Filed: 11/26/2003
• Issued: 07/03/2007
• Est. Priority Date: 03/10/2003
• Status: Active Grant

• Current Assignee: MIMIRIP LLC (Ideahub, Inc.)
• Original Assignee: Hynix Semiconductor Incorporated (SK Hynix Inc.)
• Inventors: Moon, Seung Chan, Hwang, Young Sun, Shin, Ki Soo, Lee, Sung Koo, Bok, Cheol Kyu, Lee, Geun Su
• Primary Examiner(s): WEBB, GREGORY E
• Application Number:
  US10/723,029
• Publication Number:
  US 20040180293A1
• Time in Patent Office: 1,315 Days
• Field of Search: None
• US Class Current: 510/175
• CPC Class Codes: C11D 1/345 Phosphates or phosphites
• CPC Class Codes: C11D 2111/22 Electronic devices, e.g. PCBs or semiconductors
• CPC Class Codes: C11D 3/30 Amines; Substituted amines ; Quaternized amines
• CPC Class Codes: G03F 7/322 Aqueous alkaline compositions

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 H₂O 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

1. A cleaning solution for photoresist patterns comprising:

H₂O as a solvent; and

a compound represented by following Formula 1 as a surfactant;

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:

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 C₁-C₁₀ alkyl alcohol, C₁-C₁₀ alkoxyalkyl alcohol, and mixtures thereof.

13. The cleaning solution according to claim 12, wherein the C₁-C₁₀ 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 C₁-C₁₀ 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.