Polyimide precursor composition, photosensitive resin composition, cured film, method for producing cured film, a semiconductor device, and method for producing polyimide precursor composition
A photosensitive resin composition using a polyimide precursor composition, a cured film, a method for producing a cured film, a semiconductor device, and a method for producing a polyimide precursor composition are provided. In the polyimide precursor composition, the molar ratio of repeating units represented by General Formula (1-2) among structural isomers of the polyimide precursor is 60% to 90% by mole. In General Formula (1-2), A 1 and A 2 each independently represents an oxygen atom or NH, R 111 and R 112 each independently represents a single bond or a divalent organic group, and R 113 and R 114 each independently represents a hydrogen atom or a monovalent organic group.
1. A polyimide precursor composition comprising:
a polyimide precursor including repeating units represented by General Formula (1-1),
wherein the molar ratio of repeating units represented by General Formula (1-2) among the structural isomers of the polyimide precursor is 60% to 90% by mole,
in General Formulae (1-1) and (1-2), A 1 and A 2 each independently represents an oxygen atom or NH, R 111 and R 112 each independently represents a single bond or a divalent organic group, and R 113 and R 114 each independently represents a hydrogen atom or a monovalent organic group,
wherein the weight-average molecular weight/number-average molecular weight which is the dispersity of the polyimide precursor is 2.0 to 4.0.
2. The polyimide precursor composition according to claim 1 ,
wherein at least one of R 113 or R 114 contains a polymerizable group.
3. The polyimide precursor composition according to claim 1 ,
wherein both of R 113 and R 114 contain a polymerizable group.
4. The polyimide precursor composition according to claim 1 ,
wherein at least one of A 1 or A 2 is an oxygen atom.
5. The polyimide precursor composition according to claim 1 ,
wherein R 112 is a single bond, or a group selected from a hydrocarbon group having 1 to 10 carbon atoms, —O—, —C(═O)—, —S—, —S(═O) 2 —, —NHCO—, and a combination thereof.
6. The polyimide precursor composition according to claim 1 ,
wherein the weight-average molecular weight of the polyimide precursor is 1,000 to 100,000.
7. A photosensitive resin composition comprising:
the polyimide precursor composition according to claim 1 ; and
a curable compound.
8. The photosensitive resin composition according to claim 7 ,
wherein the curable compound includes a compound having an ethylenically unsaturated bond.
9. The photosensitive resin composition according to claim 7 ,
wherein the curable compound includes a compound having two or more ethylenically unsaturated groups.
10. The photosensitive resin composition according to claim 7 ,
wherein the curable compound is at least one compound selected from a compound having at least one of a hydroxymethyl group, an alkoxymethyl group, and an acyloxymethyl group, an epoxy compound, an oxetane compound, and a benzoxazine compound.
11. The photosensitive resin composition according to claim 7 , further comprising:
at least one kind of thermal base generator selected from an acidic compound which generates a base upon heating to 40° C. or higher and an ammonium salt having an anion with a pKal of 0 to 4 and an ammonium cation.
12. The photosensitive resin composition according to claim 11 ,
wherein the acidic compound is a compound which generates a base upon heating to 120° C. to 200° C.
13. The photosensitive resin composition according to claim 11 ,
wherein the acidic compound is an ammonium salt.
14. The photosensitive resin composition according to claim 11 ,
wherein the acidic compound is a salt of an ammonium cation and a carboxylate anion.
15. The photosensitive resin composition according to claim 11 ,
wherein the ammonium salt having an anion with a pKal of 0 to 4 and an ammonium cation is an acidic compound.
16. The photosensitive resin composition according to claim 11 ,
wherein the anion contained in the ammonium salt is a carboxylate anion.
17. The photosensitive resin composition according to claim 7 , further comprising:
a photoradical polymerization initiator.
18. The photosensitive resin composition according to claim 7 , further comprising:
a photo-acid generator.
19. A cured film formed by curing the photosensitive resin composition according to claim 7 .
20. A semiconductor device comprising:
the cured film according to claim 19 .
21. A method for producing a cured film, comprising:
applying the photosensitive resin composition according to claim 7 onto a substrate; and
curing the photosensitive resin composition applied onto the substrate.
22. A method for producing a polyimide precursor composition, comprising:
reacting a compound represented by General Formula (P) with a compound represented by General Formula (Q) to produce a diester or a diamide; and
reacting the diester or the diamide with a compound represented by General Formula (R),
wherein the reaction for producing the diester or the diamide is carried out at 40° C. to 80° C. for 3 to 10 hours,
in General Formula (P), R 112 represents a single bond or a divalent organic group;
HA 3 -R 115 General Formula (Q)
in General Formula (Q), A 3 's each independently represent an oxygen atom or NH, and R 115 represents a monovalent organic group; and
H 2 N—R 111 —NH 2 General Formula (R)
in General Formula (R), R 111 represents a divalent organic group,
wherein the polyimide precursor composition comprises a polyimide precursor including repeating units represented by General Formula (1-1), and
the molar ratio of repeating units represented by General Formula (1-2) among the structural isomers of the polyimide precursor is 60% to 90% by mole,
in General Formulae (1-1) and (1-2), A 1 and A 2 each independently represents an oxygen atom or NH, R 111 and R 112 each independently represents a single bond or a divalent organic group, and R 113 and R 114 each independently represents a hydrogen atom or a monovalent organic group.