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US 12,663,718 B2Granted
Resist underlayer film-forming composition
AssigneeNissan Chemical Corporation
InventorsHirokazu Nishimaki, Makoto Nakajima, Keisuke Hashimoto
Life of this patent
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Abstract
The composition of the present invention contains a polymer to which there is attached a group represented by the following formula (1): (wherein each of Rx, Sy, and Sz represents a hydrogen atom or a monovalent organic group; each of Ry and Rz represents a single bond or a divalent organic group; each of ring Ary and ring Arz represents a C4 to C20 cyclic alkyl group or a C6 to C30 aryl group, and ring Ary and ring Arz may be linked together to form a new ring structure therebetween; ny is an integer of 0 to the maximum number corresponding to allowable substitution to ring Ary; nz is an integer of 0 to the maximum number corresponding to allowable substitution to ring Arz; and * is a polymer bonding site).
Claims8
A resist underlayer film-forming composition containing a polymer, wherein the polymer is a novolak resin having a structure in which an addition unit having a group represented by the following formula (1) is bound to any of the rings of a formed novolak resin:
- wherein
- each Rx represents a monovalent organic group that has 2 to 20 carbon atoms and optionally includes at least one of a nitrogen atom, an oxygen atom, and a sulfur atom, and comprises a cyclic skeleton having from 2 to 5 and 7 to 20 carbon atoms, a linear-chain skeleton, or a branched-chain skeleton;
- each of Sy and Sz represents a hydrogen atom or a monovalent organic group that has 2 to 20 carbon atoms and optionally includes at least one of a nitrogen atom, an oxygen atom, and a sulfur atom, and comprises a cyclic skeleton having from 2 to 5 and 7 to 20 carbon atoms, a linear-chain skeleton, or a branched-chain skeleton;
- each of Ry and Rz represents a single bond or a divalent organic group;
- each of ring Ary and ring Arz represents a C4 to C20 cyclic alkyl group or a C6 to C30 aryl group, and ring Ary and ring Arz may be linked together to form a new ring structure therebetween;
- ny is an integer of 0 to the maximum number corresponding to allowable substitution to ring Ary;
- nz is an integer of 0 to the maximum number corresponding to allowable substitution to ring Arz;
- and
- * is a novolak resin bonding site;
- and
- wherein
- the polymer includes at least one of a unit represented by the following formula (1a) and a unit represented by the following formula (1b):
- wherein
- each of AU represents a group represented by formula (1);
- each of R1 represents a halogen group, a nitro group, an amino group, a hydroxyl group, a glycidyl ether group, an aromatic hydrocarbyl group, a C1 to C10 alkyl group, or a C2 to C10 alkenyl group and may include at least one of an ether group, a ketone group, and an ester group;
- each of R2 represents a hydrogen atom or a heterocyclic group;
- each of R3 represents a hydrogen atom, an aromatic hydrocarbyl group, a heterocyclic group, a C1 to C10 alkyl group, or a C2 to C10 alkenyl group, wherein each of the aromatic hydrocarbyl group and the heterocyclic group of R2 and R3 may have at least one substituent selected from among the group consisting of a halogen group, a nitro group, an amino group, a formyl group, a carboxyl group, an alkyl carboxylate ester group, a hydroxyl group, a C1 to C10 alkyl group, a C1 to C10 alkoxy group, and a C6 to C40 aryl group;
- provided that R2 and R3 are not both a hydrogen atom;
- R2 and R3 may be linked together to form a ring structure;
- each ring Ar1 represents a benzene ring, a naphthalene ring, or an anthracene ring;
- ring Ar2 is a heterocyclic ring;
- each n is an integer of ≥1;
- each n1 is an integer of ≥0;
- and
- each n+n1 is an integer of 1 to the maximum number corresponding to allowable substitution to ring Ar1;
- wherein
- when R3 represents an aromatic hydrocarbyl group or R2 represents a heterocyclic group, the polymer is a novolak resin that is produced through polymerization by use of, as raw materials, an aldehyde and/or a ketone, and at least one member of a bisphenol, an amine, and a heterocyclic compound, in which
- the aldehyde is selected from the group consisting of an aromatic aldehyde, and a heterocyclic aldehyde;
- and the aromatic aldehyde is selected the group consisting of 1-pyrenecarboxyaldehyde, naphthaldehyde, anthracenecarboxyaldehyde, anisaldehyde, terephthaldehyde, anthrylaldehyde, phenanthrylaldehyde, salicylaldehyde, phenylacetaldehyde, 3-phenylpropionaldehyde, tolylaldehyde, (N,N-dimethylamino)benzaldehyde, and acetoxybenzaldehyde;
- the heterocyclic aldehyde is selected the group consisting of furfural, pyridinecarboxyaldehyde, and thiophenecarboxyaldehyde;
- the aromatic ketone is selected the group consisting of diphenyl ketone, phenyl naphthyl ketone, dinaphthyl ketone, phenyl tolyl ketone, ditolyl ketone, and 9-fluorenone;
- and
- the bisphenol is selected from the group consisting of 1,3-bis[2-(4-hydroxyphenyl)-2-propyl]benzene, 2-phenylindole, 1-phenyl-2-naphthylamine, and 1,4-bis[2-(4-hydroxyphenyl)-2-propyl]benzene.
30 more elements
A resist underlayer film-forming composition containing a polymer, wherein the polymer is a novolak resin having a structure in which a formed novolak resin includes a unit represented by the following formula (1a-1) and/or a unit represented by the following formula (1a-2), and an addition unit having a group represented by the following formula (1) is bound to any of the rings of the formed novolak resin:
- wherein
- each Rx represents a monovalent organic group that has 2 to 20 carbon atoms and optionally includes at least one of a nitrogen atom, an oxygen atom, and a sulfur atom, and comprises a cyclic skeleton having from 2 to 5 and 7 to 20 carbon atoms, a linear-chain skeleton, or a branched-chain skeleton;
- each of Sy and Sz represents a hydrogen atom or a monovalent organic group that has 2 to 20 carbon atoms and optionally includes at least one of a nitrogen atom, an oxygen atom, and a sulfur atom, and comprises a cyclic skeleton having from 2 to 5 and 7 to 20 carbon atoms, a linear-chain skeleton, or a branched-chain skeleton;
- each of Ry and Rz represents a single bond or a divalent organic group;
- each of ring Ary and ring Arz represents a C4 to C20 cyclic alkyl group or a C6 to C30 aryl group, and ring Ary and ring Arz may be linked together to form a new ring structure therebetween;
- ny is an integer of 0 to the maximum number corresponding to allowable substitution to ring Ary;
- nz is an integer of 0 to the maximum number corresponding to allowable substitution to ring Arz;
- and
- * is a novolak resin bonding site;
- wherein
- each of AU represents a group represented by formula (1);
- each of R1 represents a halogen group, a nitro group, an amino group, an aromatic hydrocarbyl group, a C1 to C10 alkyl group, or a C2 to C6 alkenyl group;
- each of R2 represents an aromatic hydrocarbyl group or a heterocyclic group;
- each of R3 represents a hydrogen atom, a phenyl group, or a naphthyl group;
- when each of R2 and R3 is a phenyl group, they may be linked together to form a fluorene ring;
- each of R4 represents a hydrogen atom, an acetal group, an acyl group, a glycidyl group, a C1 to C10 alkyl group, or a C2 to C6 alkenyl group;
- ring Ar1 is a benzene ring;
- each of X is a benzene ring, and two —C(CH3)2— groups bonding to the benzene ring are in m- or p-relation;
- each of n1 is 0 or 1;
- the sum na+nb is independently an integer of ≥1;
- and
- each of the sum na+n1 and the sum nb+n1 is an integer of 0 to the maximum number corresponding to allowable substitution to ring Ar1;
- and
- the unit represented by the formula (1a-1) and/or a unit represented by the following formula (1a-2) is selected from the group consisting of the following (in which the group represented by formula (1) is omitted, and the polymer that includes the unit represented by the formula (1a-1) and/or a unit represented by the formula (1a-2) is formed through bonding of the group represented by the formula (1) to any of the rings of the following):
21 more elements
A resist underlayer film-forming composition containing a polymer, wherein the polymer is a novolak resin having a structure in which a formed novolak resin includes a polymer represented by the following formula (1a-3), and an addition unit having a group represented by the following formula (1) is bound to any of the rings of the formed novolak resin:
- wherein
- each of Rx, Sy, and Sz represents a hydrogen atom or a monovalent organic group that has 2 to 20 carbon atoms and optionally includes at least one of a nitrogen atom, an oxygen atom, and a sulfur atom, and comprises a cyclic skeleton having from 2 to 5 and 7 to 20 carbon atoms, a linear-chain skeleton, or a branched-chain skeleton;
- each of Ry and Rz represents a single bond or a divalent organic group;
- each of ring Ary and ring Arz represents a C4 to C20 cyclic alkyl group or a C6 to C30 aryl group, and ring Ary and ring Arz may be linked together to form a new ring structure therebetween;
- ny is an integer of 0 to the maximum number corresponding to allowable substitution to ring Ary;
- nz is an integer of 0 to the maximum number corresponding to allowable substitution to ring Arz;
- and
- * is a novolak resin bonding site;
- wherein
- each of AU represents a group represented by formula (1);
- each of R1 represents a halogen group, a nitro group, an amino group, a hydroxyl group, a C6 to C40 aromatic hydrocarbyl group, a C1 to C10 alkyl group, or a C2 to C10 alkenyl group, and may include at least one of an ether group, a ketone group, and an ester group;
- R2 represents a heterocyclic group or a C6 to C40 aromatic hydrocarbyl group, and the heterocyclic group or the aromatic hydrocarbyl group may have at least one substituent selected from among a halogen group, a nitro group, an amino group, a formyl group, a carboxyl group, a hydroxyl group, a C1 to C10 alkyl group, a C1 to C10 alkoxy group, and a C6 to C40 aryl group;
- R3 represents a hydrogen atom, a heterocyclic group, a C6 to C40 aromatic hydrocarbyl group, a C1 to C10 alkyl group, or a C2 to C10 alkenyl group, and the heterocyclic group, the aromatic hydrocarbyl group, the alkyl group, or the alkenyl group may have at least one substituent selected from among a halogen group, a nitro group, an amino group, and a hydroxyl group;
- R2 and R3 may be linked together to form a ring structure;
- R5 represents at least one member selected from among a hydrogen atom, a C1 to C10 alkyl group, a C2 to C10 alkenyl group, and a C6 to C40 aryl group and may include at least one of an ether group, a ketone group, and an ester group;
- each of ring Ar1 represents a benzene ring or a naphthalene ring;
- each of n1 is an integer of 0 to 3;
- the sum na+nb is independently an integer of ≥1;
- and
- each of the sum na+n1 and the sum nb+n1 is an integer of 0 to the maximum number corresponding to allowable substitution to ring Ar1.
17 more elements
A resist underlayer film-forming composition containing a polymer, wherein the polymer is a novolak resin having a structure in which a formed novolak resin includes a polymer represented by the following formula (1b-1), and an addition unit having a group represented by the following formula (1) is bound to any of the rings of the formed novolak resin:
- wherein
- each of Rx, Sy, and Sz represents a hydrogen atom or a monovalent organic group that has 2 to 20 carbon atoms and optionally includes at least one of a nitrogen atom, an oxygen atom, and a sulfur atom, and comprises a cyclic skeleton having from 2 to 5 and 7 to 20 carbon atoms, a linear-chain skeleton, or a branched-chain skeleton;
- each of Ry and Rz represents a single bond or a divalent organic group;
- each of ring Ary and ring Arz represents a C4 to C20 cyclic alkyl group or a C6 to C30 aryl group, and ring Ary and ring Arz may be linked together to form a new ring structure therebetween;
- ny is an integer of 0 to the maximum number corresponding to allowable substitution to ring Ary;
- nz is an integer of 0 to the maximum number corresponding to allowable substitution to ring Arz;
- and
- * is a novolak resin bonding site;
- wherein
- each of AU represents a group represented by formula (1);
- each of R1 represents a halogen group, a nitro group, an amino group, a hydroxyl group, a C6 to C40 aromatic hydrocarbyl group, a C1 to C10 alkyl group, or a C2 to C10 alkenyl group, and may include at least one of an ether group, a ketone group, and an ester group;
- R2 represents a hydrogen atom, a heterocyclic group, or a C6 to C40 aromatic hydrocarbyl group;
- the heterocyclic group or the aromatic hydrocarbyl group may have at least one substituent selected from among a halogen group, a nitro group, an amino group, a formyl group, a carboxyl group, an alkyl carboxylate ester group, a phenyl group, a hydroxyl group, a C1 to C10 alkoxy group, and a C6 to C40 aryl group;
- R3 represents a hydrogen atom, a heterocyclic group, a C6 to C40 aromatic hydrocarbyl group, or a C1 to C10 alkyl group;
- R2 and R3 may be linked together to form a ring structure;
- ring Ar1 represents a benzene ring, a naphthalene ring, or an anthracene ring;
- R5 represents at least one member selected from among a hydrogen atom, a C1 to C10 alkyl group, a C2 to C10 alkenyl group, and a C6 to C40 aryl group and may include at least one of an ether group, a ketone group, and an ester group;
- the sum na+nb is independently an integer of ≥1;
- each of n1 and n3 is an integer of ≥0;
- each of the sum na+n1 and the sum nb+n1 is an integer of 0 to the maximum number corresponding to allowable substitution to ring Ar1;
- and
- n3 is an integer of 0 to the maximum number corresponding to allowable substitution to the R1-bound heterocyclic ring.
19 more elements
Dependencies are inferred from the claim text.