Photoresist polymer and photoresist composition containing the same

• US 7,279,256 B2
• Filed: 05/09/2005
• Issued: 10/09/2007
• Est. Priority Date: 07/30/2004
• Status: Expired due to Fees

• Current Assignee: Hynix Semiconductor Incorporated (SK Hynix Inc.)
• Original Assignee: Hynix Semiconductor Incorporated (SK Hynix Inc.)
• Inventors: Son, Min Seok
• Primary Examiner(s): Chu; John S.
• Application Number:
  US11/124,762
• Publication Number:
  US 20060022297A1
• Time in Patent Office: 883 Days
• Field of Search: 430/18, 430/20.1, 430/326, 430/330, 430/905, 430/910
• US Class Current: 430/18
• CPC Class Codes: C08F 220/1804 C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
• CPC Class Codes: C08F 222/06 Maleic anhydride
• CPC Class Codes: C08F 230/085 the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes
• CPC Class Codes: C08F 232/08 having condensed rings coumarone-indene polymers C08F244/00
• CPC Class Codes: G03F 7/0395 the macromolecular compound having a backbone with alicyclic moieties
• CPC Class Codes: G03F 7/0758 with silicon- containing groups in the side chains
• CPC Class Codes: H01L 21/0274 Photolithographic processes
• CPC Class Codes: Y10S 430/106 Binder containing
• CPC Class Codes: Y10S 430/111 Polymer of unsaturated acid or ester

Abstract

Photoresist polymers and photoresist compositions are disclosed. A photoresist polymer comprising a polymerization repeating unit represented by Formula I is less sensitive to change in the amount of energy due to its higher active energy than that of a conventional photoresist polymer. As a result, a phenomenon where the portion of the pattern for the storage electrode contact region that receives relatively large amount of light becomes too thin is avoided when the device isolation film pattern is formed, and wherein pattern collapse caused by a high aspect ratio due to high etching resistance is prevented or avoided.

wherein

R₁–R₁₀, a, b, c and d are as defined in the description.

Claims

1. A photoresist polymer comprising a polymerization repeating unit represented by Formula 1:

2. The photoresist polymer according to claim 1, wherein the polymer has a molecular weight ranging from 1,500 to 4,000.

3. The photoresist polymer according to claim 1, wherein the polymerization repeating unit represented by Formula 1 is represented by Formula 1a:

4. A photoresist composition comprising the photoresist polymer described in claim 1, a photoacid generator and an organic solvent.

5. The photoresist composition according to claim 4, wherein the photoacid generator is one or more compounds selected from the group consisting of phthalimidotrifluoromethane sulfonate, dinitrobenzyltosylate, n-decyl disulfone, naphthylimido trifluoromethane sulfonate, diphenyl iodide hexafluorophosphate, diphenyl iodide hexafluoroarsenate, diphenyl iodide hexafluoroantimonate, diphenyl p-methoxyphenylsulfonium triflate, diphenyl p-toluenylsulfonium triflate, diphenyl p-isobutylphenylsulfonium triflate, diphenyl p-t-butylphenylsulfonium triflate, triphenylsulfonium hexafluorophosphate, triphenylsulfonium hexafluoroarsenate, triphenylsulfonium hexafluoroantimonate, triphenylsulfonium triflate, dibutylnaphthylsulfonium triflate, and mixtures thereof.

6. The photoresist composition according to claim 4, wherein the photoacid generator is present in an amount ranging from 0.01 wt % to 5 wt % based on the photoresist polymer.

7. The photoresist composition according to claim 4, wherein the organic solvent is selected from the group consisting of diethyleneglycoldiethylether, methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, propyleneglycol methyletheracetate, cyclohexanone, 2-heptanone, ethyl lactate and mixtures thereof.

8. The photoresist composition according to claim 4, wherein the organic solvent is present in an amount ranging from 100 wt % to 1,500 wt % based on the photoresist polymer.

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

(a) forming a photoresist film by coating the photoresist composition of claim 4 on an underlying layer;

(b) soft-baking the photoresist film;

(c) exposing the baked photoresist film to light;

(d) post-baking the exposed photoresist film; and

(e) developing the resulting structure to obtain a photoresist pattern.

10. The method according to claim 9, wherein the soft baking process of step (b) is performed at a temperature ranging from 80°

C. to 150°

C.

11. The method according to claim 9, wherein the light of step (c) is selected from the group consisting of I-line (365 nm), KrF (248 nm), ArF (193 nm), F₂ (157 nm), EUV (13 nm), E-beam, X-ray and ion beam.

12. The method according to claim 9, wherein the exposing process of step (c) is performed at an exposure energy ranging from 1 mJ/cm² to 100 mJ/cm².

13. The method according to claim 9, wherein the post baking process of step (d) is performed at a temperature ranging from 90°

C. to 200°

C.

14. A semiconductor device manufactured using the method of claim 9.

15. A semiconductor device manufactured using the method of claim 10.

16. A semiconductor device manufactured using the method of claim 11.

17. A semiconductor device manufactured using the method of claim 12.

18. A semiconductor device manufactured using the method of claim 13.

19. A photoresist composition comprising the photoresist polymer of claim 2, a photoacid generator and an organic solvent.

20. The photoresist composition of claim 19, wherein the photoacid generator is one or more compounds selected from the group consisting of phthalimidotrifluoromethane sulfonate, dinitrobenzyltosylate, n-decyl disulfone, naphthylimido trifluoromethane sulfonate, diphenyl iodide hexafluorophosphate, diphenyl iodide hexafluoroarsenate, diphenyl iodide hexafluoroantimonate, diphenyl p-methoxyphenylsulfonium triflate, diphenyl p-toluenylsulfonium triflate, diphenyl p-isobutylphenylsulfonium triflate, diphenyl p-t-butylphenylsulfonium triflate, triphenylsulfonium hexafluorophosphate, triphenylsulfonium hexafluoroarsenate, triphenylsulfonium hexafluoroantimonate, triphenylsulfonium triflate, dibutylnaphthylsulfonium triflate, and mixtures thereof, and

 

wherein the organic solvent is selected from the group consisting of diethyleneglycoldiethylether, methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, propyleneglycol methyletheracetate, cyclohexanone, 2-heptanone, ethyl lactate and mixtures thereof.