Composition for film formation, film, resist underlayer film-forming method, production method of patterned substrate, and compound
The composition for film formation includes a compound including a group of the formula (1) and a solvent. In the formula (1), R 1 to R 4 each independently represent a hydrogen atom, a monovalent organic group having 1 to 20 carbon atoms, or R 1 to R 4 taken together represent a cyclic structure having 3 to 20 ring atoms together with the carbon atom or a carbon chain to which R 1 to R 4 bond. Ar 1 represents a group obtained by removing (n+3) hydrogen atoms from an aromatic ring of an arene having 6 to 20 carbon atoms. n is an integer of 0 to 9. R 5 represents a hydroxy group, a halogen atom, a nitro group, or a monovalent organic group having 1 to 20 carbon atoms.
1. A composition for film formation comprising:
an aromatic ring-containing compound represented by formula (i); and
a solvent:
wherein in the formula (i),
R 1 and R 2 each independently represent a monovalent organic group having 1 to 20 carbon atoms, R 3 and R 4 each independently represent a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms, and optionally at least part of R 1 to R 4 taken together represent a cyclic structure having 3 to 20 ring atoms together with the carbon atom or a carbon chain to which the at least part of R 1 to R 4 bond,
Ar 1 represents a group obtained by removing (n+3) hydrogen atoms from an aromatic ring of an arene having 6 to 20 carbon atoms,
n is an integer of 0 to 9,
m is an integer of 2 to 6,
R 5 represents a hydroxy group, a halogen atom, a nitro group, or a monovalent organic group having 1 to 20 carbon atoms, and optionally in a case in which R 5 is present in a plurality of number, two or more of the plurality of R 5 s taken together represent a cyclic structure having 6 to 20 ring atoms together with an atomic chain to which the two or more of the plurality of R 5 s bond,
a plurality of R 1 s are identical or different, a plurality of R 2 s are identical or different, a plurality of R 3 s are identical or different, a plurality of R 4 s are identical or different, and in the case in which R 5 is present in a plurality of number, the plurality of R 5 s are identical or different, and
R 6 represents at least one selected from the group consisting of a group represented by formula (2-1), a group represented by formula (2-2), a group represented by formula (2-3), a group represented by formula (2-4), and a group represented by formula (2-5):
wherein in the formulae (2-1) to (2-5), * denotes a binding site to the carbon atom in the aromatic ring of Ar 1 in the formula (i),
in the formula (2-1), R A represents a hydroxy group, a halogen atom, a nitro group, or a monovalent organic group having 1 to 20 carbon atoms; n1 is an integer of 0 to 4, wherein in a case in which n1 is 2 or greater, a plurality of R A s are identical or different; and m1 is an integer of 2 to 6, wherein n1+m1≤6,
in the formula (2-2), R B represents a hydroxy group, a halogen atom, a nitro group, or a monovalent organic group having 1 to 20 carbon atoms; n2 is an integer of 0 or 1; and m2 is an integer of 2 or 3, wherein n2+m2≤3,
in the formula (2-3), R C represents a hydrogen atom, a hydroxy group, a halogen atom, a nitro group, or a monovalent organic group having 1 to 20 carbon atoms; n3 is an integer of 0 to 2, wherein in a case in which n3 is 2, a plurality of R C s are identical or different; and m3 is an integer of 2 to 4, wherein n3+m3=4,
in the formula (2-4), R D1 and R D2 each independently represent a hydroxy group, a halogen atom, a nitro group, or a monovalent organic group having 1 to 20 carbon atoms; and n4a and n4b are each independently an integer of 0 to 4, wherein in a case in which n4a is 2 or greater, a plurality of R D1 s are identical or different, and in a case in which n4b is 2 or greater, a plurality of R D2 s are identical or different, and
in the formula (2-5), R E1 to R E3 each independently represent a hydroxy group, a halogen atom, a nitro group, or a monovalent organic group having 1 to 20 carbon atoms; and n5a, n5b and n5c are each independently an integer of 0 to 4, wherein in a case in which n5a is 2 or greater, a plurality of R E1 s are identical or different, in a case in which n5b is 2 or greater, a plurality of R E2 s are identical or different, and in a case in which n5c is 2 or greater, a plurality of R E3 s are identical or different.
2. The composition for film formation according to claim 1 , wherein the aromatic ring-containing compound has a molecular weight of no less than 300 and no greater than 3,000.
3. The composition for film formation according to claim 1 , wherein R 1 and R 2 in the formula (i) each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.
4. The composition for film formation according to claim 1 , wherein R 3 in the formula (i) represents a hydrogen atom.
5. The composition for film formation according to claim 1 , wherein the arene which Ar 1 in the formula (i) is derived from is benzene or naphthalene.
6. The composition for film formation according to claim 1 , wherein a content of the compound in the composition is no less than 1% by mass and no greater than 50% by mass.
7. The composition for film formation according to claim 1 , wherein the composition is suitable for formation of a resist underlayer film.
8. A resist underlayer film-forming method comprising:
applying the composition for film formation according to claim 1 directly or indirectly on an upper face side of a substrate to form a film on the upper face side of the substrate; and
heating the film to form a resist underlayer film.
9. A compound represented by formula (i):
wherein in the formula (i),
R 1 to and R 2 each independently represent a monovalent organic group having 1 to 20 carbon atoms, R 3 and R 4 each independently represent a hydrogen atom, or a monovalent organic group having 1 to 20 carbon atoms, and optionally at least part of R 1 to R 4 taken together represent a cyclic structure having 3 to 20 ring atoms together with the carbon atom or a carbon chain to which the at least part of R 1 to R 4 bond,
Ar 1 represents a group obtained by removing (n+3) hydrogen atoms from an aromatic ring of an arene having 6 to 20 carbon atoms,
n is an integer of 0 to 9,
m is an integer of 2 to 6,
R 5 represents a hydroxy group, a halogen atom, a nitro group, or a monovalent organic group having 1 to 20 carbon atoms, and optionally in a case in which R 5 is present in a plurality of number, two or more of the plurality of R 5 s taken together represent a cyclic structure having 6 to 20 ring atoms together with an atomic chain to which the two or more of the plurality of R 5 s bond,
a plurality of R 1 s are identical or different, a plurality of R 2 s are identical or different, a plurality of R 3 s are identical or different, a plurality of R 4 s are identical or different, and in the case in which R 5 is present in a plurality of number, the plurality of R 5 s are identical or different, and
R 6 represents at least one selected from the group consisting of a group represented by formula (2-1), a group represented by formula (2-2), a group represented by formula (2-3), a group represented by formula (2-4), and a group represented by formula (2-5):
wherein in the formulae (2-1) to (2-5), * denotes a binding site to the carbon atom in the aromatic ring of Ar 1 in the formula (i),
in the formula (2-1), R A represents a hydroxy group, a halogen atom, a nitro group, or a monovalent organic group having 1 to 20 carbon atoms; n1 is an integer of 0 to 4, wherein in a case in which n1 is 2 or greater, a plurality of R A s are identical or different; and m1 is an integer of 2 to 6, wherein n1+m1≤6,
in the formula (2-2), R B represents a hydroxy group, a halogen atom, a nitro group, or a monovalent organic group having 1 to 20 carbon atoms; n2 is an integer of 0 or 1; and m2 is an integer of 2 or 3, wherein n2+m2≤3,
in the formula (2-3), R C represents a hydrogen atom, a hydroxy group, a halogen atom, a nitro group, or a monovalent organic group having 1 to 20 carbon atoms; n3 is an integer of 0 to 2, wherein in a case in which n3 is 2, a plurality of R C s are identical or different; and m3 is an integer of 2 to 4, wherein n3+m3=4,
in the formula (2-4), R D1 and R D2 each independently represent a hydroxy group, a halogen atom, a nitro group, or a monovalent organic group having 1 to 20 carbon atoms; and n4a and n4b are each independently an integer of 0 to 4, wherein in a case in which n4a is 2 or greater, a plurality of R D1 s are identical or different, and in a case in which n4b is 2 or greater, a plurality of R D2 s are identical or different, and
in the formula (2-5), R E1 to R E3 each independently represent a hydroxy group, a halogen atom, a nitro group, or a monovalent organic group having 1 to 20 carbon atoms; and n5a, n5b and n5c are each independently an integer of 0 to 4, wherein in a case in which n5a is 2 or greater, a plurality of R E1 s are identical or different, in a case in which n5b is 2 or greater, a plurality of R E2 s are identical or different, and in a case in which n5c is 2 or greater, a plurality of R E3 s are identical or different.
10. The compound according to claim 9 , wherein the compound has a molecular weight of no less than 300 and no greater than 3,000.
11. The composition for film formation according to claim 1 , wherein the aromatic ring-containing compound has a molecular weight of no less than 300 and no greater than 3,000, R 1 and R 2 in the formula (i) each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, R 3 in the formula (i) represents a hydrogen atom, and the arene which Ar 1 in the formula (i) is derived from is benzene or naphthalene.
12. A production method of a patterned substrate comprising:
applying the composition for film formation according to claim 1 directly or indirectly on an upper face side of a substrate to form a film on the upper face side of the substrate;
heating the film to form a resist underlayer film;
forming a resist pattern directly or indirectly on an upper face side of the resist underlayer film; and
etching the substrate using the resist pattern as a mask.
13. The production method of a patterned substrate according to claim 12 , wherein the aromatic ring-containing compound has a molecular weight of no less than 300 and no greater than 3,000.
14. The production method of a patterned substrate according to claim 12 , wherein R 1 and R 2 in the formula (i) each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.
15. The production method of a patterned substrate according to claim 12 , wherein R 3 in the formula (i) represents a hydrogen atom.
16. The production method of a patterned substrate according to claim 12 , wherein the arene which Ar 1 in the formula (i) is derived from is benzene or naphthalene.
17. The compound according to claim 9 , wherein R 1 and R 2 in the formula (i) each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.
18. The compound according to claim 9 , wherein R 3 in the formula (i) represents a hydrogen atom.
19. The compound according to claim 9 , wherein the arene which Ar 1 in the formula (i) is derived from is benzene or naphthalene.