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US 9,957,339 B2Granted
Copolymer and associated layered article, and device-forming method
AssigneesRohm and Haas Electronic Materials LLC, The University of Queensland
InventorsJames W. Thackeray, Ke Du, Peter Trefonas, III, Idriss Blakey, Andrew Keith Whittaker
Life of this patent
Estimating the term…
Abstract
A copolymer is prepared by the polymerization of monomers that include an ultraviolet absorbing monomer, and a base-solubility-enhancing monomer. The copolymer is useful for forming a topcoat layer for electron beam and extreme ultraviolet lithographies. Also described are a layered article including the topcoat layer, and an associated method of forming an electronic device.
Claims8
A copolymer,
- wherein the copolymer comprises the polymerization product of monomers comprising:
- an out-of-band absorbing monomer comprising an unsubstituted or substituted C6-C18 aryl group that is free of fluorine, an unsubstituted or substituted C2-C17 heteroaryl group, a C5-C12 dienone group, or a combination thereof;
- and
- a base-solubility-enhancing monomer selected from the group consisting of (meth)acrylate esters of poly(ethylene oxide)s, (meth)acrylate esters of poly(propylene oxide)s, base-labile (meth)acrylate esters, (meth)acrylate esters substituted with a group having a pKa of 2 to 12, and combinations thereof;
- wherein the out-of-band absorbing monomer comprising an unsubstituted or substituted C6-C18 aryl group that is free of fluorine has the structure
- wherein
- R1 is hydrogen or methyl,
- n is 0, 1, 2, 3, or 4, and
- Ar1 is an unsubstituted or substituted C6-C18 aryl group that is free of fluorine;
- wherein a film cast from the copolymer has an extinction coefficient, k, of 0.1 to 0.5 at a wavelength in the range of 150 to 400 nanometers;
- and
- wherein the copolymer has a dispersity (Mw/Mn) of 1.05 to 1.2.
9 more elements
A copolymer,
- wherein the copolymer comprises the polymerization product of monomers comprising:
- an out-of-band absorbing monomer having the structure
- wherein R1 is hydrogen or methyl, n is 0, 1, 2, 3, or 4, and Ar1 is an unsubstituted or substituted C6-C18 aryl group that is free of fluorine;
- and
- a base-solubility-enhancing monomer comprising a (meth)acrylate ester of a poly(ethylene oxide) and a (meth)acrylate ester substituted with a 1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propyl group;
- wherein the monomers comprise, based on the total moles of monomer,
- 30 to 50 mole percent of the out-of-band absorbing monomer, 30 to 50 mole percent of the (meth)acrylate ester of a poly(ethylene oxide), and
- 10 to 30 mole percent of the (meth)acrylate ester substituted with a 1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propyl group;
- wherein the copolymer has a dispersity (Mw/Mn) of 1.05 to 1.2;
- and
- wherein a film cast from the copolymer has an extinction coefficient, k, of 0.1 to 0.5 at a wavelength in the range of 150 to 400 nanometers.
8 more elements
A copolymer,
- wherein the copolymer comprises the polymerization product of monomers comprising:
- an out-of-band absorbing monomer comprising an unsubstituted or substituted C6-C18 aryl group that is free of fluorine, an unsubstituted or substituted C2-C17 heteroaryl group, a C5-C12 dienone group, or a combination thereof;
- and
- a base-solubility-enhancing monomer selected from the group consisting of (meth)acrylate esters of poly(ethylene oxide)s, (meth)acrylate esters of poly(propylene oxide)s, base-labile (meth)acrylate esters, (meth)acrylate esters substituted with a group having a pKa of 2 to 12, and combinations thereof;
- wherein the base-solubility-enhancing monomer comprises a (meth)acrylate ester of a poly(ethylene oxide) and a (meth)acrylate ester substituted with a 1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propyl group;
- wherein a film cast from the copolymer has an extinction coefficient, k, of 0.1 to 0.5 at a wavelength in the range of 150 to 400 nanometers;
- and
- wherein the copolymer has a dispersity (Mw/Mn) of 1.05 to 1.2.
5 more elements
Dependencies are inferred from the claim text.