Resist underlayer film-forming composition
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, G 1 , G 2 , G 3 , G 4 , G 5 , and G 6 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 Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , and Z 6 are each independently an alkyl group, an aryl group, a hydroxy group, an epoxy group, or a hydrogen atom.]
1 . 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-V i 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 C 6 -C 18 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 C 1 -C 9 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 R 1 s 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 R 2 s 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;
R 3 represents an aromatic hydrocarbon group which may have a substituent;
R 4 represents a hydrogen atom, a phenyl group, or a naphthyl group;
when R 3 and R 4 bonded to the same carbon atom each represent a phenyl group, R 3 and R 4 may be bonded to each other to form a fluorene ring; and in formula (1b), groups represented by two R 3 s and atoms or groups represented by two R 4 s may be different from each other;
two ks each independently represent 0 or 1;
m 0 represents an integer of 3 to 500;
each of n 0 , n 1 , and n 2 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 R 1 s, two R 2 s, two R 3 s, two R 4 s, two ks, n 1 , n 2 , and X are as defined in formula (1b); and two Q 1 s each independently represent a structural unit represented by formula (2);
(b) a polymer having a unit structure represented by formula A:
wherein each of R 1 and R 2 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,
R 3 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,
R 4 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,
R 5 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,
R 4 and R 5 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 Ar 1 and Ar 2 represents a benzene ring or a naphthalene ring; each of R 1 and R 2 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,
R 3 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,
R 4 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,
R 5 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,
R 4 and R 5 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 R 1 , R 2 , and R 3 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;
R 4 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;
R 5 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;
R 6 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 R 5 and R 6 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 R 1 to R 4 each independently represent a hydrogen atom or a methyl group; and
X 1 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;
b 1 represents an alkyl group having 1 to 16 carbon; and
b 2 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 R 1 s 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 R 2 s 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;
R 3 represents an aromatic hydrocarbon group or a heterocyclic group which may have a substituent;
when R 3 and R 4 bonded to the same carbon atom each represent a phenyl group, R 3 and R 4 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(CH 3 ) 2 -groups bonded to the benzene ring have a meta-position or para-position relationship.
2 . The resist underlayer film-forming composition according to claim 1 , wherein each of A is independently a C 6 aryl group which may be interrupted by an alkylene group.
3 . The resist underlayer film-forming composition according to claim 1 , wherein Zs are each independently an aryl group which may be interrupted by an alkyl group, 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 C 1 -C 9 alkoxy group, an alkyl group, an alkenyl group, or an alkynyl group.
4 . A method of manufacturing a patterned substrate, comprising:
applying and curing a resist underlayer film-forming composition on a semiconductor substrate to form a resist underlayer film, wherein the resist underlayer film has a thickness of from 0.001 μm to 10 μm;
applying and baking a resist on the resist underlayer film to form a resist film;
exposing the resist underlayer film and the semiconductor substrate coated with the resist; and
developing the exposed resist film to perform patterning,
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-V i 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 C 6 -C 18 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 C 1 -C 9 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 R 1 s 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 R 2 s 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;
R 3 represents an aromatic hydrocarbon group which may have a substituent;
R 4 represents a hydrogen atom, a phenyl group, or a naphthyl group;
when R 3 and R 4 bonded to the same carbon atom each represent a phenyl group, R 3 and R 4 may be bonded to each other to form a fluorene ring; and in formula (1b), groups represented by two R 3 s and atoms or groups represented by two R 4 s may be different from each other;
two ks each independently represent 0 or 1;
m 0 represents an integer of 3 to 500;
each of n 0 , n 1 , and n 2 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 R 1 s, two R 2 s, two R 3 s, two R 4 s, two ks, n 1 , n 2 , and X are as defined in formula (1b); and two Q 1 s each independently represent a structural unit represented by formula (2);
(b) a polymer having a unit structure represented by formula A:
wherein each of R 1 and R 2 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,
R 3 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,
R 4 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,
R 5 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,
R 4 and R 5 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 Ar 1 and Ar 2 represents a benzene ring or a naphthalene ring; each of R 1 and R 2 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,
R 3 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,
R 4 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,
R 5 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,
R 4 and R 5 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 R 1 , R 2 , and R 3 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;
R 4 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;
R 5 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;
R 6 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 R 5 and R 6 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 R 1 to R 4 each independently represent a hydrogen atom or a methyl group; and
X 1 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;
b 1 represents an alkyl group having 1 to 16 carbon; and
b 2 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 R 1 s 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 R 2 s 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;
R 3 represents an aromatic hydrocarbon group or a heterocyclic group which may have a substituent;
R 4 represents a hydrogen atom, a phenyl group, or a naphthyl group;
when R 3 and R 4 bonded to the same carbon atom each represent a phenyl group, R 3 and R 4 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(CH 3 ) 2 -groups bonded to the benzene ring have a meta-position or para-position relationship.
5 . The method of manufacturing a patterned substrate according to claim 4 , wherein the curing is performed by baking.
6 . The method of manufacturing a patterned substrate according to claim 4 , wherein the curing is performed by baking followed by irradiation with ultraviolet rays.
7 . A method of manufacturing a semiconductor device, comprising:
forming a resist underlayer film using a resist underlayer film-forming composition on a semiconductor substrate, wherein the resist underlayer film has a thickness of from 0.001 μm to 10 μm;
forming a resist film on the resist underlayer film;
forming a resist pattern by irradiation with light or an electron beam and development;
etching the underlayer film through the resist pattern; and
processing the semiconductor substrate using the patterned underlayer film,
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-V i 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 C 6 -C 18 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 C 1 -C 9 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 R 1 s 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 R 2 s 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;
R 3 represents an aromatic hydrocarbon group which may have a substituent;
R 4 represents a hydrogen atom, a phenyl group, or a naphthyl group;
when R 3 and R 4 bonded to the same carbon atom each represent a phenyl group, R 3 and R 4 may be bonded to each other to form a fluorene ring; and in formula (1b), groups represented by two R 3 s and atoms or groups represented by two R 4 s may be different from each other;
two ks each independently represent 0 or 1;
m 0 represents an integer of 3 to 500;
each of n 0 , n 1 , and n 2 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 R 1 s, two R 2 s, two R 3 s, two R 4 s, two ks, n 1 , n 2 , and X are as defined in formula (1b); and two Q 1 s each independently represent a structural unit represented by formula (2);
(b) a polymer having a unit structure represented by formula A:
wherein each of R 1 and R 2 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,
R 3 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,
R 4 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,
R 5 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,
R 4 and R 5 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 Ar 1 and Ar 2 represents a benzene ring or a naphthalene ring; each of R 1 and R 2 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,
R 3 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,
R 4 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,
R 5 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,
R 4 and R 5 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 R 1 , R 2 , and R 3 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;
R 4 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;
R 5 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;
R 6 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 R 5 and R 6 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 R 1 to R 4 each independently represent a hydrogen atom or a methyl group; and
X 1 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;
b 1 represents an alkyl group having 1 to 16 carbon; and
b 2 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 R 1 s 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 R 2 s 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;
R 3 represents an aromatic hydrocarbon group or a heterocyclic group which may have a substituent;
R 4 represents a hydrogen atom, a phenyl group, or a naphthyl group;
when R 3 and R 4 bonded to the same carbon atom each represent a phenyl group, R 3 and R 4 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(CH 3 ) 2 -groups bonded to the benzene ring have a meta-position or para-position relationship.
8 . A compound selected from the group consisting of the following formulas (1-21) to (1-25):
wherein each of m is independently an integer of 1 to 20, and each of r is independently an integer of 0 to 5.
9 . A compound selected from the group consisting of the following formulas (1-1)-(1-7):
10 . A compound selected from the group consisting of the following formulas (1-8)-(1-11) and (1-13):
wherein, s represents an integer of 0 to 3,