Monomer, hardmask composition including monomer, and method for forming pattern by using hardmask composition
US-9556094-B2 · Jan 31, 2017 · US
US9857686B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-9857686-B2 |
| Application number | US-201615178982-A |
| Country | US |
| Kind code | B2 |
| Filing date | Jun 10, 2016 |
| Priority date | Jul 13, 2015 |
| Publication date | Jan 2, 2018 |
| Grant date | Jan 2, 2018 |
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The present invention provides a composition for forming a resist underlayer film, containing an organic solvent and either or both of a compound shown by the following general formula (1) and a condensate of the compound. There can be provided a composition for forming a resist underlayer film that is capable of forming an underlayer film, especially for use in a three-layer resist process, that can reduce reflectance, has high pattern-bend resistance, and prevents line fall and wiggling after etching of a high aspect line especially thinner than 60 nm, and a patterning process using the same.
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What is claimed is: 1. A composition for forming a resist underlayer film, comprising an organic solvent and either or both of a compound shown by the following general formula (1) and a condensate of the compound, wherein R 1 , R 3 , R 5 , and R 7 represent Z 1 , a diglycidylamino group, or a dipropargylamino group; R 2 , R 4 , R 6 , and R 8 represent Z 2 , a glycidyl group, a diglycidylamino group, or a dipropargylamino group; X represents a group shown by the following formula (1-1); n1 to n8 are each a number satisfying 0≦n1≦4, 0≦n2≦4, 0≦n3≦4, 0≦n4≦4, 0≦n5≦4, 0≦n6≦4, 0≦n7≦4, 0≦n8≦4, 0≦n1+n2≦4, 0≦n3+n4≦4, 0≦n5+n6≦4, 0≦n7+n8≦4, and 1≦n1+n2+n3+n4+n5+n6+n7+n8≦16, where Z 1 represents an alkyl group having 1 to 20 carbon atoms, an alkenyl group or alkynyl group having 2 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms, and Z 2 represents Z 1 , a hydrogen atom, or a hydroxyaryl group having 6 to 14 carbon atoms, wherein * represents a binding site with R p where p represents 2, 4, 6, or 8. 2. The composition for forming a resist underlayer film according to claim 1 , wherein the condensate is obtained by a reaction of one or more compounds shown by the general formula (1) with one or more compounds selected from a compound shown by the following general formula (2-1), a compound shown by the following general formula (2-2), trioxane, paraformaldehyde, and fluorenone, Y 1 —CHO (2-1) wherein Y 1 represents a hydrogen atom or a monovalent organic group having 1 to 30 carbon atoms and optionally containing a substituent, R 9 —CH 2 —Y 2 —CH 2 —R 9 (2-2) wherein Y 2 represents an aromatic group having 6 or more carbon atoms and optionally containing a substituent; R 9 represents an alkoxy group or alkanoyloxy group having 1 to 6 carbon atoms, or a halogen atom. 3. The composition for forming a resist underlayer film according to claim 1 , wherein the condensate is obtained by a reaction with one or more compounds selected from compounds shown by the following general formulae (3-1), (3-2), (3-3), (3-4), and (3-5), wherein R 11 and R 13 represent Z 1 , where Z 1 is as defined above, an amino group, a diglycidylamino group, or a dipropargylamino group; R 12 and R 14 represent Z 2 , where Z 2 is as defined above, a glycidyl group, a diglycidylamino group, or a dipropargylamino group; a single bond contained in R 11 to R 14 may be substituted by a double bond, a triple bond, an ether group, a carbonyl group, or a carbonyloxy group; a hydrogen atom contained in R 11 to R 14 may be substituted by a fluorine atom, a chlorine atom, or a hydroxyl group; two substituents selected from R 11 , R 12 , R 13 , and R 14 may be bonded intramolecularly to form a cyclic substituent; X 1 represents a group shown by the following formula (3-6); and n11 to n14 are each a number satisfying 0≦n11≦4, 0≦n12≦4, 0≦n13≦4, 0≦n14≦4, 0≦n11+n12≦4, 0≦n13+n14≦4, and 1≦n11+n12+n13+n14≦8, wherein R 15 represents a fluorine atom, a chlorine atom, Z 1 , where Z 1 is as defined above, a diglycidylamino group, or a dipropargylamino group; R 16 represents Z 2 , where Z 2 is as defined above, a glycidyl group, a diglycidylamino group, or a dipropargylamino group; a single bond contained in R 15 and R 16 may be substituted by a double bond, a triple bond, an ether group, a carbonyl group, or a carbonyloxy group; a hydrogen atom contained in R 15 and R 16 may be substituted by a fluorine atom, a chlorine atom, or a hydroxyl group; two substituents selected from R 15 and R 16 may be bonded intramolecularly to form a cyclic substituent; X 1 represents a group shown by the following formula (3-6); and n15 and n16 are each a number satisfying 0≦n15≦6, 0≦n16≦6, and 1≦n15+n16≦6, wherein R 17 , R 19 , R 21 , and R 23 represent Z 1 , where Z 1 is as defined above, a diglycidylamino group, or a dipropargylamino group; R 18 and R 22 represent Z 2 , where Z 2 is as defined above, a glycidyl group, a glycidyloxyethyl group, a diglycidylamino group, or a dipropargylamino group; R 20 and R 24 represent Z 2 , where Z 2 is as defined above, a glycidyl group, a diglycidylamino group, or a dipropargylamino group; a single bond contained in R 17 to R 24 may be substituted by a double bond, a triple bond, an ether group, a carbonyl group, or a carbonyloxy group; a hydrogen atom contained in R 17 to R 24 may be substituted by a fluorine atom, a chlorine atom, or a hydroxyl group; X 1 represents a group shown by the following formula (3-6); and n17 to n24 are each a number satisfying 0≦n17≦4, 0≦n18≦4, 0≦n19≦3, 0≦n20≦3, 0≦n21≦4, 0≦n22≦4, 0≦n23≦3, 0≦n24≦3, 0≦n17+n18≦4, 0≦n19+n20≦3, 0≦n21+n22≦4, 0≦n23+n24≦3, 1≦n17+n18+n19+n20≦7, and 1≦n21+n22+n23+n24≦7, wherein R 25 and R 27 represent Z 1 , where Z 1 is as defined above, a diglycidylamino group, or a dipropargylamino group; R 26 and R 28 represent Z 2 , where Z 2 is as defined above, a glycidyl group, a glycidyloxyethyl group, a diglycidylamino group, or a dipropargylamino group; a single bond contained in R 25 to R 28 may be substituted by a double bond, a triple bond, an ether group, a carbonyl group, or a carbonyloxy group; a hydrogen atom contained in R 25 to R 28 may be substituted by a fluorine atom, a chlorine atom, or a hydroxyl group; X 1 represents a group shown by the following formula (3-6); and n25 to n28 are each a number satisfying 0≦n25≦5, 0≦n26≦5, 0≦n27≦5, 0≦n28≦5, 1≦n25+n26≦5, and 1≦n27+n28≦5, wherein R 29 and R 31 represent Z 1 , where Z 1 is as defined above, a diglycidylamino group, or a dipropargylamino group; R 30 , R 32 , and R 33 represent Z 2 , where Z 2 is as defined above, a glycidyl group, a diglycidylamino group, or a dipropargylamino group; a single bond contained in R 29 to R 33 may be substituted by a double bond, a triple bond, an ether group, a carbonyl group, or a carbonyloxy group; a hydrogen atom contained in R 29 to R 33 may be substituted by a fluorine atom, a chlorine atom, or a hydroxyl group; X 1 represents a group shown by the following formula (3-6); and n29 to n32 are each a number satisfying 0≦n29≦4, 0≦n30≦4, 0≦n31≦4, 0≦n32≦4, 0≦n29+n30≦4, and 0≦n31+n32≦4, wherein * represents a binding site with R q where q represents 12, 14, 16, 18, 20, 22, 24, 26, 28, 30, or 32. 4. The composition for forming a resist underlayer film according to claim 2 , wherein the condensate is obtained by a reaction with one or more compounds selected from compounds shown by the following general formulae (3-1), (3-2), (3-3), (3-4), and (3-5), wherein R 11 and R 13 represent Z 1 , where Z 1 is as defined above, an amino group, a diglycidylamino group, or a dipropargylamino group; R 12 and R 14 represent Z 2 , where Z 2 is as defined above, a glycidyl group, a diglycidylamino group, or a dipropargylamino group; a single bond contained in R 11 to R 14 may be substituted by
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