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US 7,405,028 B2Granted
Polymers based on cinnamic acid as a bottom antireflective coating for 157 NM photolithography
AssigneeInfineon Technologies AG
InventorChristoph Hohle
Life of this patent
Estimating the term…
Abstract
A bottom antireflective coating for photolithography at 157 nm or less, where the bottom antireflective coating includes a crosslinkable polymer which contains cinnamic acid derivatives.
Claims18
A bottom antireflective coating for photolithography using wavelengths of 157 nm or less, the coating being formed from a polymer comprising cinnamic acid derivatives of at least one of the following formulas I-III:
- wherein:
- R1 comprises at least one of H, halogen, and a straight or branched alkyl chain including 1-10 carbon atoms;
- R2 for the compounds of formulas (I) and (II) comprises one or more substituents at one or more of the 1, 2, 3, 4 and 5 positions on the phenyl ring, the one or more substituents being independent of each other and each substituent comprising at least one of H, a straight or branched alkyl chain including 1-4 carbon atoms, a halogen, NO2, NH2 and OH;
- R2 for the compound of formula (III) comprises one or more substituents at one or more of the 1, 2, 3, 4 and 5 positions on the phenyl ring, the one or more substituents being independent of each other and each substituent comprising at least one of a straight or branched alkyl chain including 2-4 carbon atoms, a halogen, NO2, NH2 and OH;
- R3 comprises
- m is an integer of 1-10,000;
- n is an integer of 1-10,000;
- o is an integer of 1-10;
- R4 comprises a carboxyl protective group, a straight or branched alkyl group including 1-4 carbon atoms, or a group cleavable by a nucleophilic reagent or acid;
- and
- X comprises a reactive anchor group selected from the group consisting of acid anhydride, epoxide and ketene when R2 includes at least one of a straight or branched alkyl chain including 1-4 carbon atoms, Cl, Br, I, NO2, NH2 and OH, and X comprises a reactive anchor group selected from the group consisting of epoxide and ketene when R2 includes at least one of H, a straight or branched alkyl chain including 1-4 carbon atoms, F, Cl, Br, I, NO2, NH2 and OH;
- wherein no cinnamic derivative of the crosslinkable polymer has any of the following formulas:
9 more elements
A formulation for the production of a bottom antireflective coating for photolithography using wavelengths of not more than 157 nm, comprising a polymer, a solvent and a stabilizer wherein the polymer comprises cinnamic acid derivatives of at least one of the following formulas I-III:
- wherein:
- R1 comprises at least one of H, halogen, and a straight or branched alkyl chain including 1-10 carbon atoms;
- R2 for the compounds of formulas (I) and (II) comprises one or more substituents at one or more of the 1, 2, 3, 4 and 5 positions on the phenyl ring, the one or more substituents being independent of each other and each substituent comprising at least one of H, a straight or branched alkyl chain including 1-4 carbon atoms, a halogen, NO2, NH2 and OH;
- R2 for the compound of formula (III) comprises one or more substituents at one or more of the 1, 2, 3, 4 and 5 positions on the phenyl ring, the one or more substituents being independent of each other and each substituent comprising at least one of a straight or branched alkyl chain including 2-4 carbon atoms, a halogen, NO2, NH2 and OH;
- R3 comprises
- m is an integer of 1-10,000;
- n is an integer of 1-10,000;
- o is an integer of 1-10;
- R4 comprises a carboxyl protective group, a straight or branched alkyl group including 1-4 carbon atoms, or a group cleavable by a nucleophilic reagent or acid;
- and
- X comprises a reactive anchor group selected from the group consisting of acid anhydride, epoxide and ketene when R2 includes at least one of a straight or branched alkyl chain including 1-4 carbon atoms, Cl, Br, I, NO2, NH2 and OH, and X comprises a reactive anchor group selected from the group consisting of epoxide and ketene when R2 includes at least one of H, a straight or branched alkyl chain including 1-4 carbon atoms, F, Cl, Br, I, NO2, NH2 and OH;
- wherein no cinnamic derivative of the crosslinkable polymer has any of the following formulas:
9 more elements
A process for conducting photolithography using wavelengths of 157 nm or less, comprising the step of using a polymer for the production of a bottom antireflective coating for the photolithography process, wherein the polymer comprises cinnamic acid derivatives of at least one of the following formulas I-III:
- wherein:
- R1 comprises at least one of H, halogen, and a straight or branched alkyl chain including 1-10 carbon atoms;
- R2 for the compounds of formulas (I) and (II) comprises one or more substituents at one or more of the 1, 2, 3, 4 and 5 positions on the phenyl ring, the one or more substituents being independent of each other and each substituent comprising at least one of H, a straight or branched alkyl chain including 1-4 carbon atoms, a halogen, NO2, NH2 and OH;
- R2 for the compound of formula (III) comprises one or more substituents at one or more of the 1, 2, 3, 4 and 5 positions on the phenyl ring, the one or more substituents being independent of each other and each substituent comprising at least one of a straight or branched alkyl chain including 2-4 carbon atoms, a halogen, NO2, NH2 and OH;
- R3 comprises
- m is an integer of 1-10,000;
- n is an integer of 1-10,000;
- o is an integer of 1-10;
- R4 comprises a carboxyl protective group, a straight or branched alkyl group including 1-4 carbon atoms, or a group cleavable by a nucleophilic reagent or acid;
- and
- X comprises a reactive anchor group selected from the group consisting of acid anhydride, epoxide and ketene when R2 includes at least one of a straight or branched alkyl chain including 1-4 carbon atoms, Cl, Br, I, NO2, NH2 and OH, and X comprises a reactive anchor group selected from the group consisting of epoxide and ketene when R2 includes at least one of H, a straight or branched alkyl chain including 1-4 carbon atoms, F, Cl, Br, I, NO2, NH2 and OH;
- wherein no cinnamic derivative of the crosslinkable polymer has any of the following formulas:
9 more elements
A composition comprising a crosslinkable polymer including cinnamic acid derivatives of at least one of the following formulas I-III:
- wherein:
- R1 comprises at least one of H, halogen, and a straight or branched alkyl chain including 1-10 carbon atoms;
- R2 for the compounds of formulas (I) and (II) comprises one or more substituents at one or more of the 1, 2, 3, 4 and 5 positions on the phenyl ring, the one or more substituents being independent of each other and each substituent comprising at least one of H, a straight or branched alkyl chain including 1-4 carbon atoms, a halogen, NO2, NH2 and OH;
- R2 for the compound of formula (III) comprises one or more substituents at one or more of the 1, 2, 3, 4 and 5 positions on the phenyl ring, the one or more substituents being independent of each other and each substituent comprising at least one of a straight or branched alkyl chain including 2-4 carbon atoms, a halogen, NO2, NH2 and OH;
- R3 comprises
- m is an integer of 1-10,000;
- n is an integer of 1-10,000;
- o is an integer of 1-10;
- R4 comprises a carboxyl protective group, a straight or branched alkyl group including 1-4 carbon atoms, or a group cleavable by a nucleophilic reagent or acid;
- X comprises a reactive anchor group selected from the group consisting of acid anhydride, epoxide and ketene when R2 includes at least one of a straight or branched alkyl chain including 1-4 carbon atoms, Cl, Br, I, NO2, NH2 and OH, and X comprises a reactive anchor group selected from the group consisting of epoxide and ketene when R2 includes at least one of H, a straight or branched alkyl chain including 1-4 carbon atoms, F, Cl, Br, I, NO2, NH2 and OH;
- and
- wherein no cinnamic derivative of the crosslinkable polymer has any of the following formulas:
9 more elements
Dependencies are inferred from the claim text.