US 12,631,964 B2 · Resist underlayer film-forming composition

Abstract

A composition for forming a resist underlayer film includes: (A) a cross-linking compound that is represented by formula (I); and (D) a solvent. [In formula (I), m is an integer from 1 to 30, T is a single bond, a saturated hydrocarbon group, an aromatic group, or an unsaturated cyclic hydrocarbon group, G1, G2, G3, G4, G5, and G6 are each independently (i) or (ii), the n's are each independently an integer from 1 to 8, the n R's are each independently a hydrogen atom, an aliphatic hydrocarbon group, or an alicyclic hydrocarbon group, the A's are each independently an aryl group that may be interrupted by an alkylene group, and Z1, Z2, Z3, Z4, Z5, and Z6 are each independently an alkyl group, an aryl group, a hydroxy group, an epoxy group, or a hydrogen atom.]

A resist underlayer film, which is a cured product of a coating film formed of a resist underlayer film-forming composition,

wherein the resist underlayer film has a thickness of from 0.001 μm to 10 μm, and
wherein the resist underlayer film-forming composition comprises a crosslinkable compound (A) represented by the following formula (3), a film material (B) capable of crosslinking reaction with the crosslinkable compound (A), an acid catalyst (C), and a solvent (D),
T-Vi Formula (3)
wherein,
V is represented by
i is an integer of 2 to 6,
each of i quantity of R is independently a hydrogen atom;
or an alkyl group which may be interrupted by an oxygen atom, a nitrogen atom, or a carbonyl group;
each of i quantity of n is independently an integer of 1 to 8,
each of i quantity of A is independently a C6-C18 aryl group which may be interrupted by an alkylene group,
each of i quantity of Z is independently an alkyl group interrupted by an oxygen atom, a nitrogen atom, or a carbonyl group;
or an aryl group which may be interrupted by an oxygen atom, a nitrogen atom, or a carbonyl group and may be substituted with a hydroxy group, a halogen atom, a carboxyl group, a nitro group, a cyano group, a methylenedioxy group, an acetoxy group, a methylthio group, an amino group, a C1-C9 alkoxy group, an alkyl group, an alkenyl group, or an alkynyl group;
and
T is a single bond;
an i-valent saturated hydrocarbon group which may be interrupted by an aromatic ring;
or an i-valent aromatic group which may be interrupted by an oxygen atom or an alkylene group and may be substituted with an alkyl group or an alkenyl group;
wherein the film material (B) is at least one member selected from the group consisting of the following polymers:
(a) a novolac resin represented by one or two or more repeating structural units represented by (1a), (1b), and (1c):
wherein two R1s each independently represent an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an aromatic hydrocarbon group, a halogen atom, a nitro group, or an amino group;
two R2s each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an acetal group, an acyl group, or a glycidyl group;
R3 represents an aromatic hydrocarbon group which may have a substituent;
R4 represents a hydrogen atom, a phenyl group, or a naphthyl group;
when R3 and R4 bonded to the same carbon atom each represent a phenyl group, R3 and R4 may be bonded to each other to form a fluorene ring;
and in formula (1b), groups represented by two R3s and atoms or groups represented by two R4s may be different from each other;
two ks each independently represent 0 or 1;
m0 represents an integer of 3 to 500;
each of n0, n1, and n2 represents an integer of 2 to 500;
p represents an integer of 3 to 500;
X represents a single bond or a heteroatom;
and
two Qs each independently represent a structural unit represented by the following formula (2):
wherein two R1s, two R2s, two R3s, two R4s, two ks, n1, n2, and X are as defined in formula (1b);
and two Q1s each independently represent a structural unit represented by formula (2);
(b) a polymer having a unit structure represented by formula A:
wherein each of R1 and R2 is selected from the group consisting of a hydrogen atom, a halogen group, a nitro group, an amino group, a hydroxy group, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an aryl group having 6 to 40 carbon atoms, and a combination thereof, in which the alkyl group, the alkenyl group, or the aryl group represents a group which may have an ether bond, a ketone bond, or an ester bond,
R3 is selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an aryl group having 6 to 40 carbon atoms, and a combination thereof, in which the alkyl group, the alkenyl group, or the aryl group represents a group which may have an ether bond, a ketone bond, or an ester bond,
R4 represents an aryl group having 6 to 40 carbon atoms or a heterocyclic group which may be substituted with a halogen group, a nitro group, an amino group, or a hydroxy group,
R5 represents a hydrogen atom, or an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 40 carbon atoms, or a heterocyclic group which may be substituted with a halogen group, a nitro group, an amino group, or a hydroxy group,
R4 and R5 may be combined to form a ring together with a carbon atom to which they bond, and
each of n1 and n2 is an integer of 1 to 3;
(c) a polymer having a unit structure composed of a reaction product of a fused heterocyclic compound and a bicyclic compound;
(d) a polymer having a unit structure represented by formula B:
wherein A is a hydroxy group-substituted phenylene group derived from polyhydroxybenzene, and B is a monovalent fused aromatic hydrocarbon ring group in which 2 to 4 benzene rings are fused;
(e) a polymer having a unit structure represented by formula C:
wherein each of Ar1 and Ar2 represents a benzene ring or a naphthalene ring;
each of R1 and R2 is a substituent of a hydrogen atom on the benzene ring or the naphthalene ring and is selected from the group consisting of a halogen group, a nitro group, an amino group, a hydroxy group, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an aryl group having 6 to 40 carbon atoms, and a combination thereof, in which each of the alkyl group, the alkenyl group, and the aryl group represents an organic group which may have an ether bond, a ketone bond, or an ester bond,
R3 is selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an aryl group having 6 to 40 carbon atoms, and a combination thereof, in which each of the alkyl group, the alkenyl group, and the aryl group represents an organic group which may have an ether bond, a ketone bond, or an ester bond,
R4 is selected from the group consisting of an aryl group having 6 to 40 carbon atoms and a heterocyclic group, in which each of the aryl group and the heterocyclic group represents an organic group which may be substituted with a halogen group, a nitro group, an amino group, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 40 carbon atoms, a formyl group, a carboxyl group, or a hydroxyl group,
R5 is selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 40 carbon atoms, and a heterocyclic group, in which each of the alkyl group, the aryl group, and the heterocyclic group represents an organic group which may be substituted with a halogen group, a nitro group, an amino group, or a hydroxyl group,
R4 and R5 may be combined to form a ring together with a carbon atom to which they bond, and
each of n1 and n2 is an integer of 0 to 3;
(f) a polymer having a unit structure represented by formula D:
wherein R1, R2, and R3 are substituents of hydrogen atoms of rings and are each independently a halogen group, a nitro group, an amino group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an aryl group having 6 to 40 carbon atoms, or a combination thereof which may have an ether bond, a ketone bond, or an ester bond;
R4 is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an aryl group having 6 to 40 carbon atoms, or a combination thereof which may have an ether bond, a ketone bond, or an ester bond;
R5 is a hydrogen atom, or an aryl group having 6 to 40 carbon atoms or a heterocyclic group which may be substituted with a halogen group, a nitro group, an amino group, a formyl group, a carboxyl group, a carboxylic acid alkyl ester group, a phenyl group, an alkoxy group having 1 to 10 carbon atoms, or a hydroxyl group;
R6 is a hydrogen atom, or an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 40 carbon atoms, or a heterocyclic group which may be substituted with a halogen group, a nitro group, an amino group, a formyl group, a carboxyl group, a carboxylic acid alkyl ester group, or a hydroxyl group;
and R5 and R6 may be combined to form a ring together with a carbon atom to which they bond;
each of the ring A and the ring B represents a benzene ring, a naphthalene ring, or an anthracene ring;
and
each of n1, n2, and n3 is an integer of 0 or more and up to a maximum number of substituents capable of being substituted for the ring;
(g) a polymer having a unit structure represented by formula E:
wherein R1 to R4 each independently represent a hydrogen atom or a methyl group;
and
X1 represents a divalent organic group having at least one arylene group which may be substituted with an alkyl group, an amino group, or a hydroxyl group;
(h) a novolac resin having a unit structure represented by formula:
wherein A represents a divalent group derived from aniline, diphenylamine, phenylnaphthylamine, hydroxydiphenylamine, carbazole, phenol, N,N′-diphenylethylenediamine, N,N′-diphenyl-1,4-phenylenediamine, or a polynuclear phenol selected from the group consisting of dihydroxybenzene, trihydroxybenzene, hydroxynaphthalene, dihydroxynaphthalene, trihydroxynaphthalene, tris(4-hydroxyphenyl)methane, tris(4-hydroxyphenyl)ethane, 2,2′-biphenol, and 1,1,2,2-tetrakis(4-hydroxyphenyl)ethane;
b1 represents an alkyl group having 1 to 16 carbon;
and
b2 represents a hydrogen atom or an alkyl group having 1 to 9 carbon atoms;
and
(i) a polymer having a repeating structural unit represented by formulas G and/or H:
wherein two R1s each independently represent an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an aromatic hydrocarbon group, a halogen atom, a nitro group, or an amino group;
two R2s each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an acetal group, an acyl group, or a glycidyl group;
R3 represents an aromatic hydrocarbon group or a heterocyclic group which may have a substituent;
when R3 and R4 bonded to the same carbon atom each represent a phenyl group, R3 and R4 may be bonded to each other to form a fluorene ring;
two ks each independently represent 0 or 1;
m represents an integer of 3 to 500;
p represents an integer of 3 to 500;
X represents a benzene ring;
and
two —C(CH3)2-groups bonded to the benzene ring have a meta-position or para-position relationship.

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Resist underlayer film-forming composition

Life of this patent

Resist underlayer film-forming composition

Life of this patent

Abstract

Claims10