Resist underlayer film-forming composition
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 R x , S y , and S z represents a hydrogen atom or a monovalent organic group; each of R y and R z represents a single bond or a divalent organic group; each of ring Ar y and ring Ar z represents a C4 to C20 cyclic alkyl group or a C6 to C30 aryl group, and ring Ar y and ring Ar z may be linked together to form a new ring structure therebetween; n y is an integer of 0 to the maximum number corresponding to allowable substitution to ring Ar y ; n z is an integer of 0 to the maximum number corresponding to allowable substitution to ring Ar z ; and * is a polymer bonding site).
1 . 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 R x 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 S y and S z 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 R y and R z represents a single bond or a divalent organic group;
each of ring Ar y and ring Ar z represents a C4 to C20 cyclic alkyl group or a C6 to C30 aryl group, and ring Ar y and ring Ar z may be linked together to form a new ring structure therebetween;
n y is an integer of 0 to the maximum number corresponding to allowable substitution to ring Ar y ;
n z is an integer of 0 to the maximum number corresponding to allowable substitution to ring Ar z ; 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 R 1 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 R 2 represents a hydrogen atom or a heterocyclic group;
each of R 3 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 R 2 and R 3 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 R 2 and R 3 are not both a hydrogen atom;
R 2 and R 3 may be linked together to form a ring structure;
each ring Ar 1 represents a benzene ring, a naphthalene ring, or an anthracene ring;
ring Ar 2 is a heterocyclic ring;
each n is an integer of ≥1;
each n 1 is an integer of ≥0; and
each n+n 1 is an integer of 1 to the maximum number corresponding to allowable substitution to ring Ar 1 ;
wherein
when R 3 represents an aromatic hydrocarbyl group or R 2 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.
2 . The resist underlayer film-forming composition according to claim 1 , wherein at least one of ring Ar y and ring Ar z includes a C6 to C30 aryl group.
3 . The resist underlayer film-forming composition according to claim 1 , wherein the polymer is a novolak resin having a structure in which the addition unit has a group represented by the following formulas (1-3), (1-10) to (1-12), and (1-14) bound to any of the rings of the formed novolak resin:
Wherein * is a novolak resin bonding site.
4 . 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 R x 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 S y and S z 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 R y and R z represents a single bond or a divalent organic group;
each of ring Ar y and ring Ar z represents a C4 to C20 cyclic alkyl group or a C6 to C30 aryl group, and ring Ar y and ring Ar z may be linked together to form a new ring structure therebetween;
n y is an integer of 0 to the maximum number corresponding to allowable substitution to ring Ar y ;
n z is an integer of 0 to the maximum number corresponding to allowable substitution to ring Ar z ; and
* is a novolak resin bonding site;
wherein
each of AU represents a group represented by formula (1);
each of R 1 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 R 2 represents an aromatic hydrocarbyl group or a heterocyclic group;
each of R 3 represents a hydrogen atom, a phenyl group, or a naphthyl group;
when each of R 2 and R 3 is a phenyl group, they may be linked together to form a fluorene ring;
each of R 4 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 Ar 1 is a benzene ring;
each of X is a benzene ring, and two —C(CH 3 ) 2 — groups bonding to the benzene ring are in m- or p-relation;
each of n 1 is 0 or 1;
the sum n a +n b is independently an integer of ≥1; and
each of the sum n a +n 1 and the sum n b +n 1 is an integer of 0 to the maximum number corresponding to allowable substitution to ring Ar 1 ; 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):
5 . 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 R x , S y , and S z 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 R y and R z represents a single bond or a divalent organic group;
each of ring Ar y and ring Ar z represents a C4 to C20 cyclic alkyl group or a C6 to C30 aryl group, and ring Ar y and ring Ar z may be linked together to form a new ring structure therebetween;
n y is an integer of 0 to the maximum number corresponding to allowable substitution to ring Ar y ;
n z is an integer of 0 to the maximum number corresponding to allowable substitution to ring Ar z ; and
* is a novolak resin bonding site;
wherein
each of AU represents a group represented by formula (1);
each of R 1 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;
R 2 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;
R 3 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;
R 2 and R 3 may be linked together to form a ring structure;
R 5 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 Ar 1 represents a benzene ring or a naphthalene ring;
each of n 1 is an integer of 0 to 3;
the sum n a +n b is independently an integer of ≥1; and
each of the sum n a +n 1 and the sum n b +n 1 is an integer of 0 to the maximum number corresponding to allowable substitution to ring Ar 1 .
6 . 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 R x , S y , and S z 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 R y and R z represents a single bond or a divalent organic group;
each of ring Ar y and ring Ar z represents a C4 to C20 cyclic alkyl group or a C6 to C30 aryl group, and ring Ar y and ring Ar z may be linked together to form a new ring structure therebetween;
n y is an integer of 0 to the maximum number corresponding to allowable substitution to ring Ar y ;
n z is an integer of 0 to the maximum number corresponding to allowable substitution to ring Ar z ; and
* is a novolak resin bonding site;
wherein
each of AU represents a group represented by formula (1);
each of R 1 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;
R 2 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;
R 3 represents a hydrogen atom, a heterocyclic group, a C6 to C40 aromatic hydrocarbyl group, or a C1 to C10 alkyl group;
R 2 and R 3 may be linked together to form a ring structure;
ring Ar 1 represents a benzene ring, a naphthalene ring, or an anthracene ring;
R 5 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 n a +n b is independently an integer of ≥1;
each of n 1 and n 3 is an integer of ≥0;
each of the sum n a +n 1 and the sum n b +n 1 is an integer of 0 to the maximum number corresponding to allowable substitution to ring Ar 1 ; and
n 3 is an integer of 0 to the maximum number corresponding to allowable substitution to the R 1 -bound heterocyclic ring.
7 . The method for producing a patterned substrate, the method comprising
a step of forming a resist underlayer film on a substrate by use of the resist underlayer film-forming composition as recited in claim 1 ;
a step of forming a specific hard mask on the resist underlayer film;
a step of forming a photoresist film on the hard mask;
a step of forming a resist pattern through light exposure to and development of the photoresist film;
a step of forming a mask pattern by etching the hard mask through the resist pattern;
a step of forming a resist underlayer pattern by etching the resist underlayer film through the mask pattern; and
a step of processing the substrate through the resist underlayer pattern.
8 . The method for producing a semiconductor device, the method comprising
a step of applying, onto a substrate, the resist underlayer film-forming composition as recited in claim 1 ;
a step of etching the resist underlayer film through a specific pattern to form a patterned resist underlayer film, and
a step of processing the substrate through the patterned resist underlayer film.