Hardmask composition, hardmask layer, and method of forming patterns
US-2024377746-A1 · Nov 14, 2024 · US
US9400429B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-9400429-B2 |
| Application number | US-201514642857-A |
| Country | US |
| Kind code | B2 |
| Filing date | Mar 10, 2015 |
| Priority date | Sep 10, 2012 |
| Publication date | Jul 26, 2016 |
| Grant date | Jul 26, 2016 |
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A composition for forming a resist underlayer film is provided, which contains: a calixarene-based compound obtained from a calixarene by substituting at least a part of hydrogen atoms each on phenolic hydroxyl groups comprised in the calixarene, with a monovalent organic group having 1 to 30 carbon atoms; and an organic solvent. The monovalent organic group preferably includes a crosslinkable group. A part of hydrogen atoms each on phenolic hydroxyl groups of the calixarene-based compound is preferably substituted. The ratio of the number of substituted phenolic hydroxyl groups to the number of unsubstituted phenolic hydroxyl groups in the calixarene-based compound is preferably no less than 30/70 and no greater than 99/1.
Opening claim text (preview).
The invention claimed is: 1. A composition comprising: a calixarene-based compound obtained from a calixarene by substituting at least a part of hydrogen atoms on phenolic hydroxyl groups comprised in the calixarene, with a monovalent organic group, the monovalent organic group comprising 1 to 30 carbon atoms and a crosslinkable group; and an organic solvent, wherein the calixarene-based compound is represented by formula (4), wherein in the formula (4), R represents a hydrogen atom, a monovalent organic group having 1 to 30 carbon atoms, or a monovalent organic group comprising 1 to 30 carbon atoms and a crosslinkable group; n is 2 or 3; Y represents a hydrocarbon group having 1 to 10 carbon atoms; q is an integer of 0 to 7; p is an integer of 1 to 3, wherein a sum of p and q is no less than 1 and no greater than 8; k is 0 or 1; and X represents a substituted or unsubstituted hydrocarbon group having 1 to 30 carbon atoms and a valency of 2, wherein a plurality of Rs are identical or different, a plurality of Xs are identical or different, a plurality of “k” s are identical or different, a plurality of “p” s are identical or different, and a plurality of “q”s are identical or different, and wherein in a case where Y is present in a plurality of number, a plurality of Ys are identical or different, wherein in a case where R is the monovalent organic group comprising 1 to 30 carbon atoms and the crosslinkable group, the crosslinkable group is a group comprising a polymerizable carbon-carbon triple bond; an epoxy group; an alkoxymethyl group; a formyl group; an acetyl group; a dialkylaminomethyl group; a dimethylolaminomethyl group, a group represented by formula (a), a group represented by formula (b), or a group represented by formula (c): wherein R a and R a′ each independently represent a single bond or an alkanediyl group having 1 to 10 carbon atoms; R a″ represents a single bond, an alkanediyl group, a hydroxyalkanediyloxy group or (R″O) i ; R″ represents an alkanediyl group; “i” is an integer of 1 to 10; R b″ represents a hydrogen atom; and R b , R b′ , R c , R c′ , R c″ , R d , R d′ and R d″ each independently represent a hydrogen atom or a monovalent hydrocarbon group. 2. The composition according to claim 1 , wherein a part of hydrogen atoms on phenolic hydroxyl groups of the calixarene-based compound is substituted. 3. The composition according to claim 2 , wherein a ratio of the number of substituted phenolic hydroxyl groups to the number of unsubstituted phenolic hydroxyl groups in the calixarene-based compound is no less than 30/70 and no greater than 99/1. 4. The composition according to claim 1 , wherein a molecular weight of the calixarene-based compound is no less than 500 and no greater than 3,000. 5. The composition according to claim 1 , wherein the organic solvent comprises a polyhydric alcohol partial ether acetate solvent, a ketone solvent, a carboxylic acid ester solvent, or a mixed solvent thereof. 6. The composition according to claim 1 , further comprising a resin other than a resin corresponding to the calixarene-based compound. 7. The composition according to claim 6 , wherein the resin comprises a crosslinkable group. 8. The composition according to claim 6 , wherein the resin comprises a novolak resin, a resol resin, a styrene resin, an acenaphthylene resin, a polyarylene resin or a mixture thereof. 9. The composition according to claim 6 , wherein a weight average molecular weight of the resin is no less than 2,000 and no greater than 8,000. 10. The composition according to claim 6 , wherein a content of the resin with respect to 100 parts by mass of the calixarene-based compound is no less than 5 parts by mass and no greater than 1,000 parts by mass. 11. A pattern-forming method comprising in a following order of: applying the composition according to claim 1 directly or indirectly on a substrate to provide a resist underlayer film; forming a resist pattern directly or indirectly on the resist underlayer film; forming a pattern on the substrate through dry etching of the resist underlayer film, the substrate, or both the resist underlayer film and the substrate using the resist pattern as a mask; and removing the resist underlayer film remaining on the substrate using a basic solution, wherein the method further comprises subjecting the resist underlayer film to heating or an acid treatment before removing the resist underlayer film. 12. The pattern-forming method according to claim 11 , wherein the substrate is stepped. 13. The pattern-forming method according to claim 11 , wherein the substrate comprises a plurality of kinds of trenches. 14. The pattern-forming method according to claim 13 , wherein the plurality of kinds of trenches differ from one another in terms of an aspect ratio. 15. The pattern-forming method according to claim 14 , wherein a ratio of a maximum value of the aspect ratio to a minimum value of the aspect ratio of the plurality of kinds of trenches is no less than 10. 16. The pattern-forming method according to claim 11 , further comprising after providing the resist underlayer film and before forming the resist pattern: providing an intermediate layer directly or indirectly on the resist underlayer film, wherein the intermediate layer is further dry etched in forming the substrate pattern.
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