Claims
- 1. A method for forming a photoresist relief image, comprising:
(a) applying a photoresist composition on a substrate, the photoresist comprising a resin and a photoactive component, the resin comprising aromatic groups and electronegative groups; (b) exposing the photoresist to activating radiation and developing the exposed photoresist layer.
- 2. The method of claim 1 wherein the photoresist is exposed with radiation having a wavelength of less than about 200 nm.
- 3. The method of claim 1 wherein the photoresist is exposed with radiation having a wavelength of less than about 170 nm.
- 4. The method of claim 1 wherein the photoresist is exposed with radiation having a wavelength of less than about 160 nm.
- 5. The method of claim 1 wherein the photoresist is exposed with radiation having a wavelength about 157 nm.
- 6. The method of claim 1 wherein the photoresist is exposed with radiation having a wavelength of less than about 300 nm.
- 7. The method of any one of claims 1 through 6 wherein the resin comprises phenolic units.
- 8. The method of any one of claims 1 through 7 wherein the resin is a novolak polymer.
- 9. The method of any one of claims 1 through 7 wherein the resin comprises polymerized vinylphenol units.
- 10. The method of any one of claims 1 through 9 wherein the resin comprises halogen, halogenated alkyl, nitro, nitrile, cyano, sulfinyl, or sulfonyl groups.
- 11. The method of any one of claims 1 through 9 wherein the resin comprises fluorine.
- 12. The method of any one of claims 1 through 11 wherein the polymer comprises acrylate units.
- 13. The method of any one of claims 1 through 12 wherein the photoresist is a chemically amplified positive resist.
- 14. The method of any one of claims 1 through 12 wherein the photoresist is a negative resist.
- 15. A method for forming a photoresist relief image, comprising:
(a) applying a photoresist composition on a substrate, the photoresist comprising one or more photoacid generators and a halogenated aromatic polymer; (b) exposing the photoresist to radiation having a wavelength of about 170 nm or less and developing the exposed photoresist layer.
- 16. The method of claim 15 wherein the polymer is fluorinated.
- 17. The method of claim 15 or 16 wherein the polymer is a novolak.
- 18. The method of claim 15 or 16 wherein the polymer comprises polymerized vinylphenol units.
- 19. The method of any one of claims 15 through 18 wherein the photoresist is exposed to radiation having a wavelength of about 157 nm.
- 20. A photoresist composition comprising a photoactive component and a resin component that comprises a polymer comprising:
1) a polymer backbone comprising a plurality of carbon-carbon bond units, 2) a first electronegative group capable of withdrawing electrons from the polymer backbone; and optionally 3) a second electronegative group.
- 21. The photoresist of claim 20 wherein the polymer is a terpolymer.
- 22. The photoresist of claim 20 or 21 wherein the polymer comprises polymerized norbornene or ethylene units.
- 23. The photoresist of any one of claims 19 through 22 wherein the polymer comprises a first polymerized norbornene repeat unit, and a second polymerized norbornene repeat unit, the first and second norbornene units being different.
- 24. The photoresist of claim 23 wherein the first norbornene repeat comprises the first electronegative group, and the second norbornene repeat unit comprises the second electronegative group.
- 25. The photoresist of any one of claims 19 through 23 wherein the polymer comprises a first polymerized ethylene repeat unit, and a second polymerized ethylene repeat unit, the first and second ethylene units being different.
- 26. The photoresist of claim 25 wherein the first ethylene repeat unit comprises the first electronegative group, and the second ethylene repeat unit comprises the second electronegative group.
- 27. The photoresist of any one of claims 20 through 26 wherein the polymer further comprises an acid labile group.
- 28. The photoresist of claim 27 wherein the acid labile group is bound to a phenolic unit.
- 29. The photoresist of claim 27 wherein the acid labile group is bound to the polymer backbone.
- 30. The photoresist of claim 29 wherein the acid labile group is bound to a carbon atom substituted by the second electronegative group.
- 31. The photoresist of any one of claims 27 through 30 wherein the acid labile group is an ester, acetal, ketal, formal, or ether.
- 32. The photoresist of any one of claims 27 through 31 wherein the acid labile group comprises t-butyl, 2,2,-dimethyl-3,-methylpropyl, 1,1,2-trimethylpropyl, 1,1,2,2-tetramethylpropyl, tetrahydropyranyl, ethoxypropyl, ethyl-2-trimethylsilanyl, 2-oxa-bicylco[2.2.1] hept-6-yl (exoisomer), or 7-thia-bicyclo[2.2.1]hept-2-yl (endoisomer)
- 33. The photoresist of any one of claims 27 through 32 wherein the first electronegative group is one of halogen, nitrile or carboxyl.
- 34. The photoresist of claim 27 through 32 wherein the halogen is fluorine.
- 35. The photoresist of any one of claims 27 through 32 wherein the first electronegative group comprises fluorinated alkyl, fluorinated alkyl alcohol, perfluoroalkyl, or perfluoroalkylene.
- 36. The photoresist of any one of claims 27 through 32 wherein the first electronegative group comprises trifluoromethyl, difluoromethyl, monofluoromethyl, pentafluoroethyl, tetrafluoroethyl, trifluoroethyl, difluoroethyl, monofluoroethyl, difluorohydroxymethyl, monofluorohydroxymethyl, tetrafluorohydroxyethyl, trifluorohydroxyethyl, difluorohydroxyethyl, monofluorohydroxyethyl, hexafluorohydroxyisopropyl, pentafluorohydroxyisopropyl, tetrafluorohydroxyisopropyl, trifluorohydroxyisopropyl, difluorohydroxyisopropyl, monofluorohydroxy-tert-butyl, difluorohydroxy-tert-butyl, trifluorohydroxy-tert-butyl, tetrafluorohydroxy-tert-butyl, pentafluorohydroxy-tert-butyl, hexafluorohydroxy-tert-butyl, septafluorohydroxy-t-butyl, octafluorohydroxy-t-butyl, difluorooxymethyl, monofluorooxymethyl, tetrafluorooxyethyl, trifluorooxyethyl, difluorooxyethyl, monofluorooxyethyl, hexafluorooxyisopropyl, pentafluorooxyisopropyl, tetrafluorooxyisopropyl, trifluorooxyisopropyl, difluorooxyisopropyl, or monofluorooxyisopropyl group.
- 36. The photoresist of claim 35 wherein the acid labile group is bound to the carbon atom attached to the acrylonitrile group.
- 37. The photoresist of any one of claims 20 through 36 wherein the polymer comprises units of the following formula:
- 38. A positive chemically-amplified photoresist composition comprising one or more photoacid generator compounds and a fluorinated novolak resin or a fluorinated resin comprising polymerized vinyl phenol units.
- 39. The photoresist of claim 38 wherein the polymer is a novolak.
- 40. The photoresist of claim 38 wherein the polymer comprises polymerized vinylphenol units.
- 41. A photoresist composition comprising a photoactive component and a resin binder comprising a polymer that comprises repeat units of:
1) a group comprising a polymer backbone comprising a first phenolic ring substituted with hydrogen or at least one first electronegative group, the backbone further comprising at least one methylene unit optionally substituted with at least one second electronegative group, 2) a group comprising a second phenolic ring substituted with hydrogen or at least one third electronegative group, 3) a group comprising a third phenolic ring substituted with hydrogen or at least one fourth electronegative group, wherein,
each of the electronegative groups is the same or different, and each of the phenolic rings is the same or different.
- 42. The photoresist composition of claim 41 wherein the group comprising the second phenolic ring feature comprises a methylene unit optionally substituted with a fifth electronegative group the same or different from the first, second, third or fourth electronegative groups.
- 43. The photoresist of claim 41 or 42 wherein the second phenolic ring feature comprises a further electronegative group.
- 44. The photoresist of any one claims 41 through 43 wherein the third phenolic ring feature comprises a further electronegative group.
- 45. The photoresist composition of any one claims 41 through 45 wherein the polymer comprises a polymerized cresol formaldehyde (novolak) unit.
- 46. The photoresist composition of any one of claims 41 through 46 wherein the polymer comprises a trifluoromethylphenol unit.
- 47. The photoresist composition of any one of claims 41 through 46 wherein the polymer comprises a polymerized optionally substituted styrene unit.
- 48. The photoresist of any one of claim 42 through 48 wherein the polymer comprises a first substituted novolak repeat unit, a substituted second novolak repeat unit and a third substituted novolak repeat unit, each of the first, second and third substituted novolak units being different.
- 49. A photoresist comprising a polymer, the polymer comprising units of the following formula:
- 50. A photoresist of claim 49 wherein the polymer comprises novolak units.
- 51. A photoresist of claim 49 wherein the polymer comprises polymerized vinylphenol units.
- 52. A photoresist of claim 49 wherein the polymer is a novolak or a poly(vinylphenol).
- 53. The photoresist of any one of claims 20 through 52 wherein the polymer comprises an acid-labile repeat unit separate from a phenolic unit.
- 54. The photoresist of any one of claims 20 through 53 wherein the polymer is a terpolymer, tetrapolymer, or pentapolymer.
- 55. The photoresist of any one of claims 20 through 54 wherein the photoresist comprises at least two distinct polymers.
- 56. The photoresist of claim 55 wherein one of the two distinct polymers comprises aromatic units and the other polymer is substantially free of aromatic groups.
- 57. A method of forming a photoresist relief image, comprising:
(a) applying a coating layer of a photoresist of any one of claims 20 through 56 on a substrate; and (b) exposing and developing the photoresist layer to yield a relief image.
- 58. The method of claim 57 wherein the photoresist layer is exposed with radiation having a wavelength of less than about 200 nm.
- 59. The method of claim 57 wherein the photoresist layer is exposed with radiation having a wavelength of less than about 170 nm.
- 60. The method of claim 57 wherein the photoresist layer is exposed with radiation having a wavelength of about 157 nm.
- 61. The method of claim 57 wherein the photoresist layer is exposed with radiation having a wavelength of less than about 300 nm.
- 62. An article of manufacture comprising a substrate having thereon a photoresist of any one of claims 20 through 56.
- 63. An article of claim 62 wherein the substrate is a microelectronic wafer or an optical-electronic substrate.
- 64. A method for producing a halogenated phenolic polymer comprising oxidizing a polymer and then halogenating the polymer.
- 65. A method of claim 64 wherein the polymer is not halogenated prior to oxidation.
- 66. A method of claim 64 or 65 wherein the polymer is fluorinated.
- 67. A method of any one of claims 64 through 66 wherein the polymer is a novolak polymer.
- 68. A method of any one of claims 64 through 66 wherein the polymer comprises polymerized vinylphenol units.
- 69. A photoresist composition comprising one or more photoacid generator compounds and a halogenated polymer obtainable by steps comprising oxidizing a polymer and then halogenating the polymer.
- 70. A photoresist of claim 69 wherein the polymer is not halogenated prior to oxidation.
- 71. A photoresist of claim 69 or 70 wherein the polymer is fluorinated.
- 72. A photoresist of any one of claims 69 through 71 wherein the polymer is a novolak polymer.
- 73. A photoresist of any one of claims 69 through 71 wherein the polymer comprises polymerized vinylphenol units.
Parent Case Info
[0001] This application claims the benefit of U.S. provisional application No. 60/231,274 filed Sep. 8, 2000, and U.S. provisional application number 60/253,118, filed Nov. 27, 2000, both incorporated herein by reference.
Provisional Applications (2)
|
Number |
Date |
Country |
|
60231274 |
Sep 2000 |
US |
|
60253118 |
Nov 2000 |
US |