Fused cyclooctyne compounds and their use in metal-free click reactions
US-2015125892-A1 · May 7, 2015 · US
US9773673B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-9773673-B2 |
| Application number | US-201615148622-A |
| Country | US |
| Kind code | B2 |
| Filing date | May 6, 2016 |
| Priority date | Aug 24, 2015 |
| Publication date | Sep 26, 2017 |
| Grant date | Sep 26, 2017 |
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A composition for manufacturing a semiconductor device includes at least one carbon-based compound that includes at least one of an alkyne group and an azide group, and a solvent. A method of manufacturing a semiconductor device includes forming a feature layer on a substrate, coating the feature layer with a composition including alkyne and azide, forming a carbon-containing layer including a triazole compound by performing a heat treatment on the coated composition, forming a photoresist film on the carbon-containing layer, forming photoresist patterns by exposing and developing the photoresist film, and patterning the carbon-containing layer and the feature layer using the photoresist patterns.
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What is claimed is: 1. A composition for manufacturing a semiconductor device, the composition comprising: at least one carbon-based compound including at least one of an alkyne group and an azide group; and a solvent; wherein the at least one carbon-based compound comprises a first compound including alkyne and a second compound including azide. 2. The composition of claim 1 , wherein the first compound is expressed by the following Formula (1): R 1 ≡R 2 , Formula (1) wherein R 1 is a C1-C50 aliphatic hydrocarbon group or a C6-C50 aromatic hydrocarbon group, and R 2 is a hydrogen atom, a C1-C50 aliphatic hydrocarbon group, or a C6-C50 aromatic hydrocarbon group; and the second compound is expressed by the following Formula (2): N 3 —R 3 , Formula (2) wherein R 3 is a C1-C50 aliphatic hydrocarbon group or a C6-C50 aromatic hydrocarbon group. 3. The composition of claim 1 , wherein the first compound is expressed by the following Formula (1-1): wherein R 4 includes at least one of a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 heteroalkyl group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C2-C20 heteroalkenyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 heteroaryl group, a substituted or unsubstituted C2-C20 alkynyl group, and a substituted or unsubstituted C2-C20 heteroalkynyl group, each of R 5 and R 6 independently includes a hydrogen atom, a halogen atom, a hydroxyl group, an alkoxy group, a nitro group, a cyano group, an amino group, an azido group, an amidino group, a hydrazino group, a hydrazono group, a carbonyl group, a carbamyl group, a thiol group, an ester group, a carboxyl group, a carboxyl group salt, a sulfonic acid group, a sulfonic acid group salt, a phosphoric acid, a phosphate, substituted or unsubstituted C1-C40 alkyl, substituted or unsubstituted C1-C40 alkoxy, substituted or unsubstituted C7-C40 aryl, substituted or unsubstituted C6-C40 aryloxy, substituted or unsubstituted C2-C40 alkenyl, substituted or unsubstituted C1-C40 alkylamino, substituted or unsubstituted C6-C40 arylamino, substituted or unsubstituted C3-C20 alkylsilyl, substituted or unsubstituted C8-C40 aryl silyl, substituted or unsubstituted C7-C40 ketoaryl, substituted or unsubstituted C7-C40 ketoheteroaryl, substituted or unsubstituted C1-C40 haloalkyl, a C1-C40 fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, and a fused heteroaromatic ring, and m is an integer from 1 to 10. 4. The composition of claim 1 , wherein the second compound is expressed by the following Formula (2-1): wherein R 7 includes at least one of a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 heteroalkyl group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C2-C20 heteroalkenyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 heteroaryl group, a substituted or unsubstituted C2-C20 alkynyl group, and a substituted or unsubstituted C2-C20 heteroalkynyl group, each of R 8 and R 9 independently includes at least one of a hydrogen atom, a halogen atom, a hydroxyl group, an alkoxy group, a nitro group, a cyano group, an amino group, an azido group, an amidino group, a hydrazino group, a hydrazono group, a carbonyl group, a carbamyl group, a thiol group, an ester group, a carboxyl group, a carboxyl group salt, a sulfonic acid group, a sulfonic acid group salt, a phosphoric acid, a phosphate, substituted or unsubstituted C1-C40 alkyl, substituted or unsubstituted C1-C40 alkoxy, substituted or unsubstituted C7-C40 aryl, substituted or unsubstituted C6-C40 aryloxy, substituted or unsubstituted C2-C40 alkenyl, substituted or unsubstituted C1-C40 alkylamino, substituted or unsubstituted C6-C40 arylamino, substituted or unsubstituted C3-C20 alkylsilyl, substituted or unsubstituted C8-C40 aryl silyl, substituted or unsubstituted C7-C40 ketoaryl, substituted or unsubstituted C7-C40 ketoheteroaryl, substituted or unsubstituted C1-C40 haloalkyl, a C1-C40 fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, and a fused heteroaromatic ring, and n is an integer from 1 to 10. 5. The composition of claim 1 , wherein the at least one carbon-based compound further comprises a third compound having a structure that is different from a structure of at least one of the first and second compounds. 6. The composition of claim 1 , wherein the first compound is expressed by the following Formula (1-3): where R 11 includes at least one of a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 heteroalkyl group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C2-C20 heteroalkenyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 heteroaryl group, a substituted or unsubstituted C2-C20 alkynyl group, and a substituted or unsubstituted C2-C20 heteroalkynyl group, and each of R 12 , R 13 , R 14 , and R 15 independently includes at least one of a hydrogen atom, substituted or unsubstituted C1-C40 alkyl, substituted or unsubstituted C1-C40 alkoxy, substituted or unsubstituted C7-C40 aryl, substituted or unsubstituted C6-C40 aryloxy, substituted or unsubstituted C2-C40 alkenyl, substituted or unsubstituted C1-C40 alkylamino, substituted or unsubstituted C6-C40 arylamino, substituted or unsubstituted C3-C20 alkylsilyl, substituted or unsubstituted C8-C40 aryl silyl, substituted or unsubstituted C7-C40 ketoaryl, substituted or unsubstituted C7-C40 ketoheteroaryl, substituted or unsubstituted C1-C40 haloalkyl, a C1-C40 fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, and a fused heteroaromatic ring. 7. The composition of claim 1 , wherein the second compound is expressed by the following Formula (2-3): wherein R 16 is a C1-C50 aliphatic hydrocarbon group or a C6-C50 aromatic hydrocarbon group, and each of R 17 , R 18 , R 19 , and R 20 independently includes at least one of a hydrogen atom, substituted or unsubstituted C1-C40 alkyl, substituted or unsubstituted C1-C40 alkoxy, substituted or unsubstituted C7-C40 aryl, substituted or unsubstituted C6-C40 aryloxy, substituted or unsubstituted C2-C40 alkenyl, substituted or unsubstituted C1-C40 alkylamino, substituted or unsubstituted C6-C40 arylamino, substituted or unsubstituted C3-C20 alkylsilyl, substituted or unsubstituted C8-C40 aryl silyl, substituted or unsubstituted C7-C40 ketoaryl, substituted or unsubstituted C7-C40 ketoheteroaryl, substituted or unsubstituted C1-C40 haloalkyl, a C1-C40 fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, and a fused heteroaromatic ring. 8. A composition for manufacturing a semiconductor device, the composition comprising: at least one carbon-based compound including at least one of an alkyne group and an azide group; and a solvent; wherein the at least one carbon-based compound comprises a fourth compound including alkyne and azide. 9. A composition for manufacturing a semiconductor device, the composition comprising: at least one carbon-based compound incl
using an anti-reflective coating · CPC title
characterised by their composition, e.g. multilayer masks · CPC title
characterised by the processes involved to create the masks · CPC title
Electricity · mapped topic
Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors · CPC title
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