Claims
- 1. A photosensitive polymer comprising a copolymer of alkyl vinyl ether and maleic anhydride, represented by the following structure:
- 2. The photosensitive polymer according to claim 1, wherein R2 is one of a methyl group, an ethyl group, a 2-hydroxy ethyl group, an n-butyl group and an iso-butyl group.
- 3. The photosensitive polymer according to claim 1, wherein R3 is one of a methoxy group and an ethoxy group.
- 4. The photosensitive polymer according to claim 1, wherein the weight average molecular weight of the polymer is in the range of 3,000 to 100,000.
- 5. A photosensitive terpolymer comprising:
(a) a copolymer of alkyl vinyl ether and maleic anhydride, represented by the following structure: 43wherein X is one of a linear alkyl vinyl ether and a cyclic alkyl vinyl ether, which are respectively represented by the structures 44wherein y is one of the integer values 1 through 4, R1 is one of a hydrogen atom and a methyl group, R2 is a C1 to C20 hydrocarbon and R3 is one of a hydrogen atom, a C1 to C3 alkyl group and an alkoxy group; and (b) a comonomer having an acid-labile substituent or a polar functional group.
- 6. The photosensitive terpolymer according to claim 5, wherein R2 is one of a methyl group, an ethyl group, a 2-hydroxy ethyl group, an n-butyl group and an iso-butyl group.
- 7. The photosensitive terpolymer according to claim 6, wherein R3 is one of a methoxy group and an ethoxy group.
- 8. The photosensitive terpolymer according to claim 5, wherein the comonomer includes an acrylate derivative, a methacrylate derivative, a fumarate derivative, a styrene derivative or norbornene derivative.
- 9. The photosensitive terpolymer according to claim 5, wherein the comonomer has an alicyclic hydrocarbon group as the substituent.
- 10. The photosensitive terpolymer according to claim 5, wherein the comonomer is an acrylate or methacrylate derivative and the photosensitive terpolymer is represented by the following formula and has the weight average molecular weight of the polymer is in the range of 3,000 to 100,000:
- 11. The photosensitive terpolymer according to claim 10, wherein R5 is a t-butyl group.
- 12. The photosensitive terpolymer according to claim 10, wherein R5 is an acid-labile alicyclic hydrocarbon group.
- 13. The photosensitive terpolymer according to claim 12, wherein R5 is one of a 2-methyl-2-norbornyl group, a 2-ethyl-2-norbornyl group, a 2-methyl-2-isobornyl group, a 2-ethyl-2-isobornyl group, a 8-methyl-8-tricyclo[5.2.1.02.6]decanyl group, a 8-ethyl-8-tricyclo[5.2.1.02.6]decanyl group, a 2-methyl-2-adamantyl group, a 2-ethyl-2-adamantyl group, a 2-methyl-2-fenchyl group and a 2-ethyl-2-fenchyl group.
- 14. The photosensitive terpolymer according to claim 5, wherein the comonomer is a norbornene derivative and the photosensitive terpolymer is represented by the following formula and has the weight average molecular weight of the polymer is in the range of 3,000 to 100,000:
- 15. The photosensitive terpolymer according to claim 14, wherein R6 is a t-butyl group.
- 16. The photosensitive terpolymer according to claim 14, wherein R6 is an acid-labile alicyclic hydrocarbon group.
- 17. The photosensitive terpolymer according to claim 16, wherein R6 is one of a 2-methyl-2-norbornyl group, a 2-ethyl-2-norbornyl group, a 2-methyl-2-isobornyl group, a 2-ethyl-2-isobornyl group, a 8-methyl-8-tricyclo[5.2.1.02.6]decanyl group, a 8-ethyl-8-tricyclo[5.2.1.02.6]decanyl group, a 2-methyl-2-adamantyl group, a 2-ethyl-2-adamantyl group, a 2-methyl-2-fenchyl group and a 2-ethyl-2-fenchyl group.
- 18. A photosensitive polymer comprising:
(a) a copolymer of alkyl vinyl ether and maleic anhydride, represented by the following structure: 47wherein X is one of a linear alkyl vinyl ether and a cyclic alkyl vinyl ether, which are respectively represented by the structures 48wherein y is one of the integer values 1 through 4, R1 is one of a hydrogen atom and a methyl group, R2 is a C1 to C20 hydrocarbon, and R3 is one of a hydrogen atom, a C1 to C3 alkyl group and an alkoxy group; and (b) at least two comonomers consisting of acrylate, methacrylate or norbornene derivatives having an acid-labile substituent or a polar functional group.
- 19. The photosensitive polymer according to claim 18, wherein R2 is one of a methyl group, an ethyl group, a 2-hydroxy ethyl group, an n-butyl group and an iso-butyl group.
- 20. The photosensitive polymer according to claim 18, wherein R3 is one of a methoxy group and an ethoxy group.
- 21. A photosensitive polymer represented by the following structure:
- 22. The photosensitive polymer according to claim 21, wherein R4 and R5 independantly are C1 to C25 aliphatic hydrocarbon having at least one substituent selected from the group consisting of hydrogen atom, hydroxyl, carboxylic anhydride and —COO(R7).
- 23. The photosensitive polymer according to claim 21, wherein R7 is a t-butyl group.
- 24. The photosensitive polymer according to claim 21, wherein R7 is an acid-labile alicyclic hydrocarbon group.
- 25. The photosensitive polymer according to claim 21, wherein R7 is one of a 2-methyl-2-norbornyl group, a 2-ethyl-2-norbornyl group, a 2-methyl-2-isobornyl group, a 2-ethyl-2-isobornyl group, a 8-methyl-8-tricyclo[5.2.1.02.6]decanyl group, a 8-ethyl-8-tricyclo[5.2.1.02.6]decanyl group, a 2-methyl-2-adamantyl group, a 2-ethyl-2-adamantyl group, a 2-methyl-2-fenchyl group and a 2-ethyl-2-fenchyl group.
- 26. A resist composition comprising:
(a) a photosensitive polymer comprising a copolymer of alkyl vinyl ether and maleic anhydride, represented by the following structure: 51wherein X is one of a linear alkyl vinyl ether and a cyclic alkyl vinyl ether, which are respectively represented by the structures 52wherein y is one of the integer values 1 through 4, R1 is one of a hydrogen atom and a methyl group, R2 is a C1 to C20 hydrocarbon, and R3 is one of a hydrogen atom, a C1 to C3 alkyl group and an alkoxy group; and (b) a photoacid generator (PAG).
- 27. The resist composition according to claim 26, wherein R2 is one of a methyl group, an ethyl group, a 2-hydroxy ethyl group, an n-butyl group and an iso-butyl group.
- 28. The resist composition according to claim 26, wherein R3 is one of a methoxy group and an ethoxy group.
- 29. The resist composition according to claim 26, wherein the weight average molecular weight of the polymer is in the range of 3,000 to 100,000.
- 30. The resist composition according to claim 26, wherein the PAG is contained in an amount of 0.5 to 20% by weight based on the weight of the photosensitive polymer.
- 31. The resist composition according to claim 26, wherein the PAG is selected from the group consisting of triarylsulfonium salts, diaryliodonium salts, sulfonates or mixtures thereof.
- 32. The resist composition according to claim 31, wherein the PAG is selected from the group consisting of triphenylsulfonium triflate, triphenylsulfonium antimonate, diphenyliodonium triflate, diphenyliodonium antimonate, methoxydiphenyliodonium triflate, di-t-butyldiphenyliodonium triflate, 2,6-dinitrobenzyl sulfonates, pyrogallol tris(alkylslulfonates), N-hydroxysuccinimide triflate, norbornene-dicarboximide-triflate, triphenylsulfonium nonaflate, diphenyliodonium nonaflate, methoxydiphenyliodonium nonaflate, di-t-butyldiphenyliodonium nonaflate, N-hydroxysuccinimide nonaflate, norbornene-dicarboximide-nonaflate, triphenysulfonium perfluorooctanesulfonate (PFOS), diphenyliodonium PFOS, methoxydiphenyliodonium PFOS, di-t-butyldiphenyliodonium triflate, N-hydroxysuccinimide PFOS, and norbornene-dicarboximide PFOS, or mixtures thereof.
- 33. The resist composition according to claim 26, further comprising an organic base.
- 34. The resist composition according to claim 33, wherein the organic base is contained in an amount of 0.5 to 50 mol % based on the concentration of the PAG.
- 35. The resist composition according to claim 33, wherein the organic base is a compound comprising tertiary amine alone or in a mixture of at least two kinds thereof.
- 36. The resist composition according to claim 35, wherein the organic base is triethylamine, triisobutylamine, trioctylamine, triisodecylamine, triethanolamine, N,N-dimethyl-1-naphthylamines, N-cyclohexyl pyrrolidinone, N-cyclopentyl pyrrolidinone, N-pentyl pyrrolidinone, N-hexyl pyrrolidinone, N-allyl caprolactam, N-ethyl caprolactam, N-butyl caprolactam, N-propyl caprolactam, N-butyl valerolactam, N-isobutyl valerolactam, and N-secondary butyl valerolactam, or a mixture thereof.
- 37. A resist composition comprising:
(a) a photosensitive polymer; and (b) a photoacid generator (PAG), the photosensitive polymer comprising (a-1) a copolymer of alkyl vinyl ether and maleic anhydride and (a-2) a comonomer having an acid-labile substituent or a polar functional group, the copolymer being represented by the following structure: 53wherein X is one of a linear alkyl vinyl ether and a cyclic alkyl vinyl ether, which are respectively represented by the structures 54wherein y is one of the integer values 1 through 4, R1 is a hydrogen atom or a methyl group, R2 is a C1 to C20-hydrocarbon, and R3 is one of a hydrogen atom, a C1 to C3 alkyl group and an alkoxy group.
- 38. The resist composition according to claim 37, wherein R2 is one of a methyl group, an ethyl group, a 2-hydroxy ethyl group, an n-butyl group and an iso-butyl group.
- 39. The resist composition according to claim 37, wherein R3 is a methoxy group and an ethoxy group.
- 40. The resist composition according to claim 37, wherein the comonomer includes an acrylate derivative, a methacrylate derivative, a fumarate derivative, a styrene derivative or norbornene derivative.
- 41. The resist composition according to claim 37, wherein the comonomer has an alicyclic hydrocarbon group as the substituent.
- 42. The resist composition according to claim 37, wherein the PAG is contained in an amount of 0.5 to 20% by weight based on the weight of the photosensitive polymer.
- 43. The resist composition according to claim 37, wherein the PAG is selected from the group consisting of triarylsulfonium salts, diaryliodonium salts, sulfonates or mixtures thereof.
- 44. The resist composition according to claim 43, wherein the PAG is selected from the group consisting of triphenylsulfonium triflate, triphenylsulfonium antimonate, diphenyliodonium triflate, diphenyliodonium antimonate, methoxydiphenyliodonium triflate, di-t-butyldiphenyliodonium triflate, 2,6-dinitrobenzyl sulfonates, pyrogallol tris(alkylslulfonates), N-hydroxysuccinimide triflate, norbornene-dicarboximide-triflate, triphenylsulfonium nonaflate, diphenyliodonium nonaflate, methoxydiphenyliodonium nonaflate, di-t-butydiphenyliodonium nonaflate, N-hydroxysuccinimide nonaflate, norbornene-dicarboximide-nonaflate, triphenysulfonium perfluorooctanesulfonate (PFOS), diphenyliodonium PFOS, methoxydiphenyliodonium PFOS, di-t-butyldiphenyliodonium triflate, N-hydroxysuccinimide PFOS, and norbornene-dicarboximide PFOS, or mixtures thereof.
- 45. The resist composition according to claim 37, further comprising an organic base.
- 46. The resist composition according to claim 45, wherein the organic base is contained in an amount of 0.5 to 50 mol % based on the concentration of the PAG.
- 47. The resist composition according to claim 45, wherein the organic base is a compound comprising tertiary amine alone or in a mixture of at least two kinds thereof.
- 48. The resist composition according to claim 47, wherein the organic base is triethylamine, triisobutylamine, trioctylamine, triisodecylamine, triethanolamine, N,N-dimethyl-1-naphthylamines, N-cyclohexyl pyrrolidinone, N-cyclopentyl pyrrolidinone, N-pentyl pyrrolidinone, N-hexyl pyrrolidinone, N-allyl caprolactam, N-ethyl caprolactam, N-butyl caprolactam, N-propyl caprolactam, N-butyl valerolactam, N-isobutyl valerolactam, and N-secondary butyl valerolactam, or a mixture thereof.
Priority Claims (2)
Number |
Date |
Country |
Kind |
00-2489 |
Jan 2000 |
KR |
|
00-20603 |
Apr 2000 |
KR |
|
CROSS-REFERENCE TO RELATED APPLICATIONS
[0001] This is a continuation-in-part (CIP) of U.S. non-provisional application Ser. No. 09/576,053, filed May 23, 2000; and this is a counterpart of and claims priority to U.S. provisional application No. 60/198,761, filed Apr. 21, 2000; Korean patent application no. 00-2489, filed Jan. 19, 2000; and Korean patent application no. 00-20603, filed Apr. 19, 2000; the contents of each of which are incorporated herein by reference for all purposes.
Provisional Applications (1)
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Number |
Date |
Country |
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60198761 |
Apr 2000 |
US |
Divisions (1)
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Number |
Date |
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Parent |
09764150 |
Jan 2001 |
US |
Child |
10704977 |
Nov 2003 |
US |
Continuation in Parts (1)
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Number |
Date |
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Parent |
09576053 |
May 2000 |
US |
Child |
09764150 |
Jan 2001 |
US |