IP Library Granted Patent US 12663718
Granted Patent B2
US 12663718 · App. 17/261,253 · Granted Jun 23, 2026

Resist underlayer film-forming composition

Inventors: Hirokazu Nishimaki (Toyama, JP); Makoto Nakajima (Toyama, JP); Keisuke Hashimoto (Toyama, JP)
Assignee: NISSAN CHEMICAL CORPORATION
G03F7/11C08G8/04C08G12/08C08G12/26H10P76/2041
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Quick Facts
Patent No.
US 12663718
App. No.
17/261,253
Granted
Jun 23, 2026
Kind
B2
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 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).

Claims (105)

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.