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US 2024/0176240 A1Published application
Photosensitive resin composition, production method for polyimide cured film using same, and polyimide cured film
AssigneeAsahi Kasei Kabushiki Kaisha
InventorsSatoshi SHIBUI, Suzuka MATSUMOTO
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Abstract
Provided is photosensitive resin composition that has low dielectric characteristics, low water vapor permeability, and good chemical resistance and can form a cured relief pattern at high resolution. This photosensitive resin composition includes 100 parts by mass of a polyimide precursor resin, 0.5-10 parts by mass of a photopolymerization initiator, and 50-500 parts by mass of a solvent. The polyimide precursor resin includes at least one terminal structure selected from the group consisting of general formulas (1)-(3). The total value for the aliphatic hydrocarbon group concentration T of the polyimide precursor resin is 4-35 wt %.
Claims18
A photosensitive resin composition comprising:
- (A) 100 parts by mass of a polyimide precursor resin;
- (B) 0.5 to 10 parts by mass of a photopolymerization initiator;
- and
- (C) 50 to 500 parts by mass of a solvent;
- wherein the polyimide precursor resin (A) comprises at least one terminal structure selected from the group consisting of the following general formulas (1) to (3):
- wherein W is a divalent to trivalent organic group, R1 to R3 are each independently a hydrogen atom or a monovalent organic group having 1 to 3 carbon atoms, mi is a group represented by an integer of 1 to 2, m2 is a group represented by an integer of 2 to 10, and * means bonding to the main chain of the resin, and
- wherein, in polyimide of a polyimide cured film obtained by heating and curing the photosensitive resin composition at 350° C., aliphatic hydrocarbon group concentration T, which is the ratio of the total molecular weight of aliphatic hydrocarbon groups to the molecular weight of repeating units including structures derived from tetracarboxylic dianhydride and a diamine compound, is 4 wt % to 35 wt %;
- or
- a photosensitive resin composition comprising:
- (A) 100 parts by mass of a polyimide precursor resin;
- (B) 0.5 to 10 parts by mass of a photosensitive agent and
- (C) 100 to 300 parts by mass of a solvent;
- wherein, in polyimide of a polyimide cured film obtained by heating and curing the photosensitive resin composition at 350° C., aliphatic hydrocarbon group concentration T which is the ratio of the total molecular weight of aliphatic hydrocarbon groups to the molecular weight of repeating units including structures derived from tetracarboxylic dianhydride and a diamine compound, and photosensitive group concentration S which is the ratio of the total molecular weight of photosensitive groups to the molecular weight of repeating units in the polyimide precursor resin (A) satisfy the following formula (1):
- −77≤4T−3S≤44 (1)
- and wherein the polyimide precursor resin (A) has the other reactive unsaturated bonds which are polymerized by heat or light at the resin end, and are different from the reactive unsaturated bond side chain included in the repeating units.
12 more elements
(canceled)
A photosensitive resin composition comprising:
- (A) 100 parts by mass of a polyimide precursor resin;
- (B) 0.5 to 10 parts by mass of a photopolymerization initiator;
- and
- (C) 50 to 500 parts by mass of a solvent;
- wherein the polyimide precursor resin (A) includes a terminal structure derived from tetracarboxylic dianhydride or diamine at the end of the main chain, and
- wherein, in 1H-NMR, when a peak area of an amide group derived from the main chain structure is 1.0, an end-capping value, which indicates an end-capping ratio, is 0.02 or more when the terminal structure is derived from tetracarboxylic dianhydride, or 0.06 or more when the terminal structure is derived from diamine.
3 more elements
(canceled)
A polyimide cured film which has a dielectric loss tangent of 3.0×10−3 to 1.3×10−2 as measured at a frequency of 40 GHz by the perturbation type split cylinder resonator method, and satisfies the following formula (2):
- 3.0<tan δ40×WVTR<10.0 (2)
- wherein tan δ40 represents the dielectric loss tangent as measured at a frequency of 40 GHz by the perturbation type split cylinder resonator method, and WVTR represents the moisture permeability of a 10 μm thick polyimide cured film.
A method for producing a photosensitive resin composition, the photosensitive resin composition comprising:
- (A) 100 parts by mass of a polyimide precursor resin;
- (B) 0.5 to 10 parts by mass of a photopolymerization initiator;
- and
- (C) 50 to 500 parts by mass of a solvent;
- wherein the method comprises synthesizing the polyimide precursor resin (A) and mixing the polyimide precursor resin (A), the photopolymerization initiator (B) and the solvent (C) to obtain a photosensitive resin composition, wherein
- the synthesizing comprises the following:
- monomer preparation by obtaining an acid component monomer and/or a diamine monomer having a second compound introducing portion by (i) and/or (ii):
- (i) reacting tetracarboxylic dianhydride with a first compound having a reactive substituent which reacts with heat or light to generate a first compound introducing portion and carboxyl groups, reacting with a second compound having a reactive substituent that reacts with heat or light, which is different from the first compound, or reacting tetracarboxylic dianhydride with a second compound having a reactive substituent which reacts with heat or light to generate a second compound introducing portion and carboxyl groups, and then reacting with a first compound having a reactive substituent which reacts with heat or light, which is different from the second compound, to obtain an acid component monomer having a second compound introducing portion, and/or
- (ii) reacting a diamine compound with a second compound having a reactive substituent which reacts with heat or light to obtain a diamine monomer having a second compound introducing portion;
- and
- polymerization by synthesizing a polyimide precursor by subjecting an acid component monomer and/or a diamine monomer having a second compound introducing portion, tetracarboxylic dianhydride and a diamine compound to a condensation reaction, and
- wherein the polyimide precursor resin (A) has a reactive substituent derived from the second compound at the main chain end;
- or
- a method for producing a polyimide precursor resin, the method comprising the following:
- monomer preparation by obtaining an acid component monomer and/or a diamine monomer having a second compound introducing portion by (i) and/or (ii):
- (i) reacting tetracarboxylic dianhydride with a first compound having a reactive substituent which reacts with heat or light to generate a first compound introducing portion and carboxyl groups, reacting with a second compound having a reactive substituent which reacts with heat or light, which is different from the first compound, or reacting tetracarboxylic dianhydride with a second compound having a reactive substituent which reacts with heat or light to generate a second compound introducing portion and carboxyl groups, and then reacting with a first compound having a reactive substituent which reacts with heat or light, which is different from the second compound, to obtain an acid component monomer having a second compound introducing portion, and/or
- (ii) reacting a diamine compound with a second compound having a reactive substituent which reacts with heat or light to obtain a diamine monomer having a second compound introducing portion;
- and
- polymerization by synthesizing a polyimide precursor by subjecting an acid component monomer and/or a diamine monomer having a second compound introducing portion, tetracarboxylic dianhydride and a diamine compound to a condensation reaction, and
- wherein the polyimide precursor resin has a reactive substituent derived from the second compound at the main chain end.
17 more elements
(canceled)
Dependencies are inferred from the claim text.