WO2024143211A1 - Élément ainsi que procédé de fabrication de celui-ci, composition de résine photosensible, et élément semi-conducteur - Google Patents

Élément ainsi que procédé de fabrication de celui-ci, composition de résine photosensible, et élément semi-conducteur Download PDF

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Publication number
WO2024143211A1
WO2024143211A1 PCT/JP2023/046201 JP2023046201W WO2024143211A1 WO 2024143211 A1 WO2024143211 A1 WO 2024143211A1 JP 2023046201 W JP2023046201 W JP 2023046201W WO 2024143211 A1 WO2024143211 A1 WO 2024143211A1
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group
pattern
substrate
formula
insulating pattern
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PCT/JP2023/046201
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English (en)
Japanese (ja)
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雄大 山川
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富士フイルム株式会社
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  • SAP Semi Additive Process
  • Damascene method a method in which a resist is formed in advance on non-circuit areas, the circuit areas are formed by plating, the resist is then removed to form wiring, and the spaces between the wiring are then filled with an insulating material.
  • FIG. 1 is a schematic cross-sectional view showing an example of a first member of the present invention.
  • FIG. 2 is an enlarged view of a part of the schematic cross-sectional view of the first member of the present invention shown in FIG. 1 .
  • FIG. 2 is a schematic cross-sectional view showing an example of a second member of the present invention.
  • 4A to 4C are process explanatory diagrams each showing, in cross section, a process of a method for producing a first member according to an embodiment of the present invention.
  • 5A to 5C are process explanatory views each showing, in schematic cross-sectional views, a process (part) of a method for producing a second member according to an embodiment of the present invention.
  • FIG. 5 is a process explanatory diagram showing a schematic cross-sectional view of a process (part) of a method for producing a second member according to an embodiment of the present invention (continuation of FIG. 5 ).
  • a numerical range expressed using the symbol "to” means a range that includes the numerical values before and after "to” as the lower limit and upper limit, respectively.
  • the term “process” includes not only an independent process but also a process that cannot be clearly distinguished from other processes, so long as the process can achieve its intended effect.
  • groups (atomic groups) when there is no indication of whether they are substituted or unsubstituted, the term encompasses both unsubstituted groups (atomic groups) and substituted groups (atomic groups).
  • an "alkyl group” encompasses not only alkyl groups that have no substituents (unsubstituted alkyl groups) but also alkyl groups that have substituents (substituted alkyl groups).
  • exposure includes not only exposure using light but also exposure using particle beams such as electron beams and ion beams. Examples of light used for exposure include the bright line spectrum of a mercury lamp, far ultraviolet light represented by an excimer laser, extreme ultraviolet light (EUV light), X-rays, electron beams, and other actinic rays or radiation.
  • a third layer or element may be interposed between the reference layer and the other layer, and the reference layer does not need to be in contact with the other layer.
  • the direction in which the layers are stacked on the substrate is referred to as "upper", or, in the case of a resin composition layer, the direction from the substrate to the resin composition layer is referred to as “upper”, and the opposite direction is referred to as "lower”. Note that such a vertical direction is set for the convenience of this specification, and in an actual embodiment, the "upper” direction in this specification may be different from the vertical upward direction.
  • the composition may contain, as each component contained in the composition, two or more compounds corresponding to that component.
  • the content of each component in the composition means the total content of all compounds corresponding to that component.
  • the temperature is 23° C.
  • the pressure is 101,325 Pa (1 atm)
  • the relative humidity is 50% RH.
  • combinations of preferred aspects are more preferred aspects.
  • Patent Document 1 describes or suggests that the conductive pattern includes a conductive pattern whose area on the surface opposite the substrate is larger than the area of the conductive pattern at a position 500 nm deep from the surface.
  • the first member of the present invention will now be described in detail.
  • the first member of the present invention has a substrate, an insulating pattern disposed on the substrate, and a conductive pattern present between the insulating patterns.
  • the substrate is not particularly limited, and may be a semiconductor production substrate such as silicon, silicon nitride, polysilicon, silicon oxide, or amorphous silicon, quartz, glass, an optical film, a ceramic material, a deposition film, a magnetic film, a reflective film, a metal substrate such as Ni, Cu, Cr, or Fe, paper, a SOG (Spin On Glass), a TFT (thin film transistor) array substrate, or an electrode plate for a plasma display panel (PDP).
  • the substrate may have a layer such as an adhesion layer or an oxide layer made of hexamethyldisilazane (HMDS), a sealant (epoxy molding compound: EMC), or the like, provided on the surface.
  • HMDS hexamethyldisilazane
  • EMC epoxy molding compound
  • the substrate may be in the form of a wafer or a panel.
  • a semiconductor substrate is particularly preferred, and a silicon substrate (silicon wafer) is more preferred.
  • the substrate may have an electronic circuit region including an electronic circuit.
  • the electronic circuit may have an element such as a semiconductor.
  • the electronic circuit is preferably electrically connected to the conductive pattern.
  • the insulating pattern preferably comprises polyimide or polybenzoxazole, and more preferably comprises polyimide.
  • the content of polyimide or polybenzoxazole (when two or more types are contained, the total content of these) is preferably 20 to 99.5 mass %, more preferably 30 to 99 mass %, further preferably 40 to 98 mass %, and particularly preferably 50 to 97 mass %, based on the total mass of the insulating pattern.
  • the cyclization rate (imidization rate) of the polyimide is preferably 70% or more, more preferably 80% or more, and even more preferably 90% or more.
  • the upper limit of the cyclization rate is not particularly limited, and may be 100% or less.
  • the alloy may contain elements other than those exemplified above.
  • the copper alloy may contain silicon atoms to form a Corson alloy.
  • oxygen that is inevitably dissolved, organic residues of raw material compounds mixed during precipitation, etc. may be present.
  • the conductive pattern may be a wiring terminal including a plurality of different members. Of these, the conductive pattern is preferably a pattern made of copper.
  • the substrate in the second member may be the same as the substrate in the first member described above, and the preferred embodiments are also the same.
  • the indentation elastic modulus of the first insulating pattern is not particularly limited, but is preferably 6.0 GPa or less, more preferably 4.0 to 6.0 GPa, and even more preferably 4.5 to 5.5 GPa.
  • the indentation elastic modulus can be measured by a nanoindentation test.
  • the second insulating pattern preferably contains polyimide or polybenzoxazole, and more preferably contains polyimide.
  • the content of polyimide or polybenzoxazole (when two or more types are contained, the total content of these) is preferably 20 to 99.5 mass %, more preferably 30 to 99 mass %, even more preferably 40 to 98 mass %, and particularly preferably 50 to 97 mass %, relative to the total mass of the second insulating pattern.
  • the cyclization rate (imidization rate) of the polyimide is preferably 70% or more, more preferably 80% or more, and even more preferably 90% or more.
  • the upper limit of the cyclization rate is not particularly limited, and may be 100% or less.
  • the coating method can be appropriately selected depending on the shape of the substrate, and if the substrate is a circular substrate such as a wafer, spin coating, spray coating, inkjet, etc. are preferred, and if the substrate is a rectangular substrate, slit coating, spray coating, inkjet, etc. are preferred.
  • the spin coating method for example, it can be applied for about 10 seconds to 3 minutes at a rotation speed of 500 to 3,500 rpm.
  • a coating film formed by applying the coating material to a temporary support in advance using the above-mentioned application method may be transferred onto the substrate.
  • the transfer method the production methods described in paragraphs 0023 and 0036 to 0051 of JP-A No.
  • the heating rate in the post-exposure heating step is preferably from 1 to 12° C./min, more preferably from 2 to 10° C./min, and even more preferably from 3 to 10° C./min, from the temperature at the start of heating to the maximum heating temperature.
  • the rate of temperature rise may be appropriately changed during heating.
  • the heating means in the post-exposure baking step is not particularly limited, and a known hot plate, oven, infrared heater, etc. can be used. It is also preferable that the heating be performed in an atmosphere of low oxygen concentration by flowing an inert gas such as nitrogen, helium, or argon.
  • examples of basic compounds that the alkaline aqueous solution may contain include inorganic alkalis, primary amines, secondary amines, tertiary amines, and quaternary ammonium salts.
  • the compounds described in paragraph 0387 of WO 2021/112189 can be used as the organic solvent.
  • the organic solvent examples include methanol, ethanol, propanol, isopropanol, butanol, pentanol, octanol, diethylene glycol, propylene glycol, methyl isobutyl carbinol, and triethylene glycol
  • examples of amides that are suitable include N-methylpyrrolidone, N-ethylpyrrolidone, and dimethylformamide.
  • a method of supplying the developer through a straight nozzle or a method of continuously supplying the developer through a spray nozzle is preferred, and from the viewpoint of the permeability of the developer into the image areas, a method of supplying the developer through a spray nozzle is more preferred.
  • a process may be adopted in which the developer is continuously supplied through a straight nozzle, the substrate is spun to remove the developer from the substrate, and after spin drying, the developer is continuously supplied again through a straight nozzle, and the substrate is spun to remove the developer from the substrate. This process may be repeated multiple times.
  • Methods of supplying the developer in the development step include a step in which the developer is continuously supplied to the substrate, a step in which the developer is kept substantially stationary on the substrate, a step in which the developer is vibrated by ultrasonic waves or the like on the substrate, and a combination of these steps.
  • the organic solvent preferably accounts for 50% by mass or more, more preferably 70% by mass or more, and even more preferably 90% by mass or more, based on the total mass of the rinse solution. Furthermore, the organic solvent may account for 100% by mass, based on the total mass of the rinse solution.
  • the method of supplying the rinse liquid is not particularly limited as long as it can form a desired pattern, and examples of the method include a method of immersing the substrate in the rinse liquid, a method of supplying the rinse liquid to the substrate by puddling, a method of supplying the rinse liquid to the substrate by showering, and a method of continuously supplying the rinse liquid onto the substrate by means of a straight nozzle or the like.
  • the rinse liquid may be supplied using a shower nozzle, a straight nozzle, a spray nozzle, etc., and the method of continuously supplying the rinse liquid using a spray nozzle is preferred, while from the viewpoint of the permeability of the rinse liquid into the image areas, the method of supplying the rinse liquid using a spray nozzle is more preferred.
  • the type of nozzle and examples include a straight nozzle, a shower nozzle, a spray nozzle, etc.
  • the rinsing time is preferably 10 seconds to 10 minutes, and more preferably 20 seconds to 5 minutes.
  • the temperature of the rinsing liquid during rinsing is not particularly specified, but is preferably 10 to 45°C, and more preferably 18°C to 30°C.
  • the development step may include a step of contacting the pattern with a processing liquid after treatment with a developer or after washing the pattern with a rinse liquid. Also, a method may be employed in which the processing liquid is supplied before the developer or rinse liquid in contact with the pattern is completely dried.
  • the treatment liquid includes a treatment liquid containing at least one of water and an organic solvent, and at least one of a basic compound and a base generator.
  • Preferred aspects of the organic solvent, and at least one of the basic compound and the base generator are the same as the preferred aspects of the organic solvent, and at least one of the basic compound and the base generator used in the above-mentioned rinse solution.
  • the method of supplying the processing liquid to the pattern can be the same as the above-mentioned method of supplying the rinsing liquid, and the preferred embodiments are also the same.
  • the content of the basic compound or base generator in the treatment liquid is preferably 10% by mass or less, more preferably 5% by mass or less, based on the total mass of the treatment liquid.
  • the lower limit of the content is not particularly limited, but is preferably, for example, 0.1% by mass or more.
  • the content of the basic compound or base generator is preferably 70 to 100 mass % based on the total solid content of the treatment liquid.
  • the treatment liquid may contain only one kind of at least one of the basic compound and the base generator, or may contain two or more kinds.
  • the total amount thereof is preferably within the above range.
  • the pattern obtained by the development step (if a rinsing step is performed, the pattern after rinsing) may be subjected to a heating step in which the pattern obtained by the development step is heated.
  • the first member manufacturing method of the present invention may include a heating step of heating the pattern obtained in the development step.
  • the heating step may be carried out after the conductive layer forming step described below or after the polishing step described below, so long as it is carried out after the developing step, and the timing of carrying out the heating step is not particularly limited.
  • the method for producing the first member of the present invention may include a heating step of heating a pattern obtained by another method without performing a development step, or a film obtained in the film formation step.
  • the resin such as the polyimide precursor is cyclized to become a resin such as a polyimide. Furthermore, crosslinking of unreacted crosslinkable groups in the specific resin or in the crosslinking agent other than the specific resin also proceeds.
  • the heating temperature (maximum heating temperature) in the heating step is preferably 50 to 450°C, more preferably 150 to 350°C, further preferably 150 to 250°C, even more preferably 160 to 250°C, and particularly preferably 160 to 230°C.
  • the heating step is preferably a step in which the cyclization reaction of the polyimide precursor is promoted within the pattern by the action of the base generated from the base generator through heating.
  • the heating step is preferably performed at a temperature rise rate of 1 to 12° C./min from the starting temperature to the maximum heating temperature.
  • the temperature rise rate is more preferably 2 to 10° C./min, and even more preferably 3 to 10° C./min.
  • the temperature is increased from the starting temperature to the maximum heating temperature at a rate of preferably 1 to 8° C./sec, more preferably 2 to 7° C./sec, and even more preferably 3 to 6° C./sec.
  • the temperature at the start of heating is preferably 20°C to 150°C, more preferably 20°C to 130°C, and even more preferably 25°C to 120°C.
  • the temperature at the start of heating refers to the temperature at which the process of heating to the maximum heating temperature begins.
  • the resin composition of the present invention when applied to a substrate and then dried, it is the temperature of the film (layer) after drying, and it is preferable to raise the temperature from a temperature 30 to 200°C lower than the boiling point of the solvent contained in the resin composition.
  • the heating time (heating time at the maximum heating temperature) is preferably 5 to 360 minutes, more preferably 10 to 300 minutes, and even more preferably 15 to 240 minutes.
  • Heating may be performed at two or more heating temperatures.
  • a process may be performed in which the temperature is increased from 25°C to 150°C at 5°C/min, held at 150°C for 60 minutes, increased from 150°C to 230°C at 5°C/min, and held at 230°C for 120 minutes.
  • Such a pretreatment process can improve the properties of the film.
  • the pretreatment process is preferably performed for a short time of about 10 seconds to 2 hours, more preferably 15 seconds to 30 minutes.
  • the pretreatment process may be performed in two or more steps, for example, a first pretreatment process may be performed in the range of 100 to 150°C, and then a second pretreatment process may be performed in the range of 150 to 230°C. Furthermore, after heating, the material may be cooled, and in this case, the cooling rate is preferably 1 to 5° C./min.
  • the heating step is preferably performed in an atmosphere with a low oxygen concentration by flowing an inert gas such as nitrogen, helium, or argon, or by performing the heating step under reduced pressure, etc.
  • the oxygen concentration is preferably 50 ppm (volume ratio) or less, and more preferably 20 ppm (volume ratio) or less.
  • the heating means in the heating step is not particularly limited, but examples thereof include a hot plate, an infrared oven, an electric heating oven, a hot air oven, and an infrared oven.
  • the pattern obtained by the development step (if a rinsing step is performed, the pattern after rinsing) may be subjected to a post-development exposure step in which the pattern after the development step is exposed to light instead of or in addition to the heating step. That is, the method for producing the first member of the present invention may include a post-development exposure step of exposing the pattern obtained by the development step. The method for producing the first member of the present invention may include a heating step and a post-development exposure step, or may include only one of the heating step and the post-development exposure step.
  • the post-development exposure step for example, a reaction in which cyclization of a polyimide precursor or the like proceeds due to exposure of a photobase generator to light, or a reaction in which elimination of an acid-decomposable group proceeds due to exposure of a photoacid generator to light, can be promoted.
  • the post-development exposure step it is sufficient that at least a part of the pattern obtained in the development step is exposed, but it is preferable that the entire pattern is exposed.
  • the exposure dose in the post-development exposure step is preferably 50 to 20,000 mJ/cm 2 , and more preferably 100 to 15,000 mJ/cm 2 , calculated as exposure energy at a wavelength to which the photosensitive compound has sensitivity.
  • the post-development exposure step can be carried out, for example, using the light source in the exposure step described above, and it is preferable to use broadband light.
  • the method for forming a first member of the present invention includes a conductive layer forming step of forming a conductive layer on the insulating patterns and in areas between the insulating patterns of a substrate on which insulating patterns have been formed, to obtain member A.
  • the conductive layer can be formed by plating, applying a conductive paste, or the like.
  • the maximum thickness of the conductive layer formed in the conductive layer forming step is not particularly limited, but is preferably 500 to 10,000 nm, and more preferably 1,000 to 5,000 nm.
  • the conductive layer formation process can be carried out, for example, by electrolytic copper plating.
  • the conductive layer formed in the conductive layer forming step is present in the regions between the insulating patterns and on top of the insulating patterns, filling the regions between the insulating patterns and covering the insulating patterns. It is not necessary that all of the regions between the insulating patterns are filled with the conductive layer, and for example, the conductive layer may be formed along the inner walls (side and bottom surfaces) of these regions. In such an embodiment, the regions not filled with the conductive layer can be removed by polishing in a polishing step described later, or the surface of the member can be flattened by polishing after forming a barrier layer described later.
  • the seed layer is formed by, for example, sputtering.
  • a seed layer can be formed by using a metal such as titanium or chromium as a sputtering target and introducing oxygen, nitrogen, or the like as a reactive gas. This can be performed by a known method. In addition, other known methods for forming a seed layer may also be used.
  • the thickness of the seed layer is preferably from 20 to 400 nm, more preferably from 30 to 300 nm, and further preferably from 40 to 250 nm.
  • the seed layer may be formed of two or more layers. When the seed layer is formed of two or more layers, it is preferable that the thickness of each layer is within the above range. For example, after forming a seed layer of titanium, chromium, nickel or the like as a first layer, a seed layer of a metal used for a conductive layer, such as copper, may be formed as a second layer by plating or the like.
  • the first method of producing a member of the present invention includes a polishing step of polishing member A to obtain a member having the conductive pattern and insulating pattern exposed on the surface.
  • the polishing step is a step of polishing member A to obtain a member in which the conductive pattern and the insulating pattern are exposed.
  • the polishing step removes the surface of the conductive layer to form a conductive pattern.
  • a seed layer is formed on the insulating pattern by the above-mentioned method, it is preferable that the seed layer on the insulating pattern is also removed.
  • the polishing may be performed by physical polishing such as cutting, mechanical polishing, grinding, plasma treatment, laser ablation, or the like, or is preferably performed by chemical polishing such as CMP (Chemical Mechanical Polishing), and is more preferably performed by CMP.
  • the slurry used in the above-mentioned CMP is not particularly limited, but can be silica slurry, ceria slurry, alumina slurry, titania slurry, zirconia slurry, germania slurry, manganese oxide slurry, diamond slurry, etc.
  • the size of the particles of the slurry is not particularly limited, but from the viewpoint of scratch prevention, the average particle size is preferably 1000 nm or less, more preferably 500 nm or less, and even more preferably 200 nm or less.
  • the lower limit of the particle size of the slurry is not particularly limited, but from the viewpoint of polishing rate, it is preferably 10 nm or more.
  • these methods may be combined, for example, by performing CMP after cutting.
  • silica slurries include, for example, NP6220, NP6502, NP6504, NP6610, NP6605, NP8020H, NP8020, NP8030, NP8040, NP8040W, and EG1103 (all manufactured by Nitta DuPont).
  • the content of particles such as silica, ceria, and alumina in the slurry is not particularly limited, but from the viewpoint of suppressing scratches and the like, the content is preferably 0.01 to 80 mass %, more preferably 0.1 to 70 mass %, and even more preferably 0.2 to 60 mass %, based on the total mass of the slurry.
  • the content of each component in the slurry is described as the content of each component when the slurry is used for polishing.
  • the content is the content in the diluted composition.
  • two kinds of particles having different materials or two kinds of particles having different particle diameters may be used in combination. In these cases, it is preferable that the total content of the particles contained falls within the above numerical range.
  • the slurry also preferably contains an oxidizing agent, which acts on the surface of the insulating pattern, making the insulating pattern easier to remove, and is believed to increase the etching rate.
  • an oxidizing agent include hydrogen peroxide, peroxides, nitrates, iodates, periodates, hypochlorites, chlorites, chlorates, perchlorates, persulfates, dichromates, permanganates, ozone water, silver (II) salts, and iron (III) salts.
  • pH buffers include sodium hydroxide, potassium hydroxide, lithium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, trisodium phosphate, tripotassium phosphate, disodium phosphate, dipotassium phosphate, sodium borate, potassium borate, sodium tetraborate (borax), potassium tetraborate, sodium o-hydroxybenzoate (sodium salicylate), potassium o-hydroxybenzoate, sodium 5-sulfo-2-hydroxybenzoate (sodium 5-sulfosalicylate), potassium 5-sulfo-2-hydroxybenzoate (potassium 5-sulfosalicylate), and ammonium hydroxide.
  • Other examples include amino acids and amino acid derivatives such as glycine, alanine, and N-methylglycine, and organic acids such as butyric acid and glycolic acid. However, usable pH buffers are not limited to these.
  • the amount of pH adjuster added is not particularly limited as long as it is an amount capable of adjusting the pH of the slurry to a target value, and the compound and the amount added may be appropriately adjusted depending on the purpose.
  • the pH can be selected arbitrarily, but in some cases it may be preferable to adjust the pH to the alkaline side, for example, pH 8 to 14, in terms of the polishing rate, etc. It is also possible to prepare a slurry at a low pH, and the optimum pH can be appropriately selected taking into consideration the polishing rate and the antiseptic properties of the adjacent metal.
  • the slurry also preferably contains a corrosion inhibitor.
  • a corrosion inhibitor for example, it is possible to suppress corrosion of metal (for example, copper) in the conductive pattern.
  • Corrosion inhibitors include heteroaromatic ring compounds.
  • As the corrosion inhibitor a compound that forms a passivation film on the metal surface to be polished is preferred.
  • a “heteroaromatic ring compound” is a compound having a ring structure containing one or more heteroatoms as ring members.
  • a nitrogen atom, a sulfur atom, an oxygen atom, a selenium atom, a tellurium atom, a phosphorus atom, a silicon atom or a boron atom is preferable, a nitrogen atom, a sulfur atom, an oxygen atom or a selenium atom is more preferable, a nitrogen atom, a sulfur atom or an oxygen atom is particularly preferable, and a nitrogen atom or a sulfur atom is most preferable.
  • the heteroaromatic ring compound is not particularly limited, but examples thereof include the compounds described in paragraphs 0027 to 0035 of JP-A-2009-224695.
  • the above slurry may contain various known additives depending on the purpose.
  • known additives include, but are not limited to, surfactants, solvents, and chelating agents.
  • polishing may be performed in two stages. Specifically, a method includes a first polishing step in which the conductive layer is removed by polishing down to the surface of the seed layer to expose the seed layer, and then a second polishing step in which the seed layer is removed to expose the insulating pattern.
  • the method for producing the first member of the present invention preferably further comprises, after the polishing step, a barrier layer forming step of forming a barrier layer present on the conductive pattern.
  • a barrier layer is formed on the exposed surface of the conductive pattern exposed by the polishing process.
  • the material constituting the barrier layer is not particularly limited, and known materials can be used, such as SiN 2 , TiN, a cobalt compound, and nickel.
  • the method for forming the barrier layer is not particularly limited, and any known method can be used, and the barrier layer can be formed by electroless plating or the like.
  • the thickness of the barrier layer is not particularly limited, but is preferably from 50 to 500 nm, more preferably from 100 to 400 nm, and even more preferably from 150 to 300 nm.
  • FIG. 4 is a process explanatory diagram showing, in schematic cross-sectional views, the process of the method for producing the first member according to one embodiment of the present invention.
  • 4A shows a state in which insulating patterns 102 are formed on a substrate 100.
  • the insulating patterns 102 have regions 103 between the insulating patterns.
  • a method for producing a member according to a second aspect of the present invention is a method for producing a member comprising a substrate, a first insulating pattern present on the substrate, a second insulating pattern present on at least a portion of a surface of the first insulating pattern, and a conductive pattern providing electrical conductivity between a region between the first insulating pattern and a region between the second insulating pattern, the method comprising steps A to C, and including, as the conductive pattern, a conductive pattern whose area on a surface opposite the substrate is larger than the area of the conductive pattern at a position 500 nm deep from the surface.
  • the method for producing the second member of the present invention includes a preparation step (step A) of preparing a member A including the first insulating pattern and the second insulating pattern.
  • the member A may be manufactured by a known method, or may be obtained by means of purchase or the like. A manufacturing method for manufacturing the member A will be described below.
  • the method for producing the member A preferably includes a first film formation step of applying a photosensitive resin composition (a composition for forming a first insulating pattern) to a substrate to form a film, a first exposure step of selectively exposing the film formed by the first film formation step, a first development step of developing the film exposed by the first exposure step with a developer to form a first insulating pattern, a second film formation step of applying a photosensitive resin composition (a composition for forming a second insulating pattern) to the first insulating pattern to form a film, a second exposure step of selectively exposing the film formed by the second film formation step, and a second development step of developing the film exposed by the second exposure step with a developer to form a second insulating pattern.
  • a photosensitive resin composition a composition for forming a first insulating pattern
  • the manufacturing method of component A may form a first insulating pattern by etching or the like instead of the first exposure step and the first development step, and may form a second insulating pattern by etching or the like instead of the second exposure step and the second development step.
  • first insulating pattern by etching or the like instead of the first exposure step and the first development step
  • second insulating pattern by etching or the like instead of the second exposure step and the second development step.
  • the method for producing a cured product of the present invention preferably includes a first film-forming step of applying a photosensitive resin composition to a substrate to form a film.
  • the substrate in the first film-forming step is as described above.
  • the resin composition can be applied by the same means as in the film formation step in the first method of manufacturing the component of the present invention described above, and the preferred embodiments are also the same.
  • the method for producing the member A preferably includes a second film-forming step of applying a photosensitive resin composition to the first insulating pattern to form a film.
  • the second film-forming step can be carried out in the same manner as the first film-forming step described above, except that the photosensitive resin composition is applied to the first insulating pattern instead of the substrate, and the preferred aspects are also the same.
  • the seed layer formation process can be performed in the same manner as the seed layer formation process in the first component manufacturing method of the present invention described above, and the preferred embodiments are also the same.
  • FIG. 5( e ) shows a state in which a line-and-space pattern (space portion) 22 is formed in film 20 so that the space portion is located over the hole pattern in film 10, forming a second insulating pattern before curing, and then heating changes the first insulating pattern before curing to first insulating pattern 16, and the second insulating pattern before curing to second insulating pattern 26.
  • the member shown in FIG. 5( e ) corresponds to an example of member A in process A.
  • R 115 include tetracarboxylic acid residues remaining after removal of anhydride groups from tetracarboxylic dianhydride.
  • the polyimide precursor may contain only one type of tetracarboxylic dianhydride residue or two or more types of tetracarboxylic dianhydride residues as the structure corresponding to R 115 .
  • the tetracarboxylic dianhydride is preferably represented by the following formula (O).
  • R 115 represents a tetravalent organic group.
  • the preferred range of R 115 is the same as that of R 115 in formula (2), and the preferred range is also the same.
  • the polyimide precursor has fluorine atoms in its structure.
  • the fluorine atom content in the polyimide precursor is preferably 10% by mass or more, and 20% by mass or less.
  • the polyimide preferably has an ethylenically unsaturated bond.
  • the polyimide may have an ethylenically unsaturated bond at the end of the main chain or in a side chain, but preferably in the side chain.
  • the ethylenically unsaturated bond is preferably radically polymerizable.
  • the ethylenically unsaturated bond is preferably contained in R 132 or R 131 in the repeating unit represented by formula (4) described below, and more preferably contained in R 132 or R 131 as a group having an ethylenically unsaturated bond.
  • the amount of ethylenically unsaturated bonds relative to the total mass of the polyimide is preferably 0.0001 to 0.1 mol/g, and more preferably 0.0005 to 0.05 mol/g.
  • the polyimide may have a polarity conversion group such as an acid-decomposable group.
  • the acid-decomposable group in the polyimide is the same as the acid-decomposable group described in R 113 and R 114 in the above formula (2), and preferred embodiments are also the same.
  • the polarity conversion group is contained, for example, in R 131 and R 132 in the repeating unit represented by formula (4) described later, or at the terminal of the polyimide.
  • R 132 may be a tetracarboxylic acid residue remaining after removal of the anhydride group from a tetracarboxylic dianhydride.
  • a specific example is R 115 in the formula (2) of the polyimide precursor. From the viewpoint of the strength of the organic film, R 132 is preferably an aromatic diamine residue having 1 to 4 aromatic rings.
  • the polyimide preferably contains a repeating unit represented by the following formula (4-3) as the repeating unit represented by formula (4).
  • formula (4-3) X1 represents an organic group having 4 or more carbon atoms, Y1 represents an organic group having 4 or more carbon atoms, and each R1 independently represents a structure represented by the following formula (R-1), m represents an integer of 0 to 4, and n represents an integer of 1 or more.
  • R-1 L 1 represents a linking group having a valence of a2+1, A 1 represents a polymerizable group, a2 represents an integer of 1 or more, and * represents a bonding site with X 1 or Y 1 in formula (4-3).
  • R X2 and R X3 are bonded to form a ring structure
  • the structure formed by bonding R X2 and R X3 is preferably a single bond, -O- or -CR 2 -, more preferably -O- or -CR 2 -, and even more preferably -O-.
  • R represents a hydrogen atom or a monovalent organic group, preferably a hydrogen atom, an alkyl group or an aryl group, and more preferably a hydrogen atom.
  • X 1 is a group containing a structure in which two or more hydrogen atoms have been removed from a structure represented by formula (V-1)
  • X 1 is preferably a group represented by the following formula (V-1-1).
  • * represents a bonding site with four carbonyl groups to which X 1 in formula (4-3) is bonded
  • n1 represents an integer of 0 to 5, and is also preferably an integer of 1 to 5.
  • the hydrogen atoms in the following structure may be further substituted with known substituents such as a hydroxy group and a hydrocarbon group.
  • m in the above formula (4-3) is an integer of 1 to 4, it is preferable that m hydrogen atoms are substituted with R 1 in formula (4-3).
  • X 1 is a group containing a structure obtained by removing two or more hydrogen atoms from a structure represented by formula (V-2), X 1 is preferably a group represented by the following formula (V-2-1) or formula (V-2-2), and from the viewpoint of lowering the amine value in the resin, it is preferably a group represented by formula (V-2-2).
  • L X1 represents a single bond or -O-, and * represents a bonding site with the four carbonyl groups to which X 1 in formula (4-3) is bonded.
  • R X1 are as described above.
  • the hydrogen atoms in these structures may be further substituted with known substituents such as a hydroxy group and a hydrocarbon group.
  • m in the above formula (4-3) is an integer of 1 to 4, it is preferable that m hydrogen atoms are substituted with R 1 in formula (4-3).
  • X 1 is a group containing a structure in which two or more hydrogen atoms have been removed from a structure represented by formula (V-4), X 1 is preferably a group represented by formula (V-4-1) below.
  • * represents a bonding site with four carbonyl groups to which X 1 in formula (4-3) is bonded, and n1 represents an integer of 0 to 5.
  • the hydrogen atoms in the structure below may be further substituted with known substituents such as a hydroxy group and a hydrocarbon group.
  • m in the above formula (4-3) is an integer of 1 to 4, it is preferable that m hydrogen atoms are substituted with R 1 in formula (4-3).
  • R N is preferably a hydrogen atom, an alkyl group or an aryl group, and more preferably a hydrogen atom.
  • the preferred aspects of R N are as described above.
  • R N represents a hydrogen atom or a monovalent organic group
  • * represents a bonding site with a carbon atom.
  • X1 does not contain an ester bond in the structure.
  • X 1 does not contain an imide structure, a urethane bond, a urea bond, or an amide bond, and it is more preferable that X 1 does not contain an imide structure, a urethane bond, a urea bond, an amide bond, or an ester bond.
  • Y 1 is preferably a group containing a structure in which two or more hydrogen atoms have been removed from a structure represented by any one of formulas (V-1) to (V-4) above.
  • Y 1 is a group containing a structure obtained by removing two or more hydrogen atoms from a structure represented by formula (V-3), Y 1 is preferably a group represented by formula (V-3-3) or formula (V-3-4) below, and from the viewpoint of decreasing the dielectric constant, etc., it is preferably a group represented by formula (V-3-3).
  • * represents a bonding site with the two nitrogen atoms to which Y 1 in formula (4-3) is bonded.
  • R X2 and R X3 are as described above.
  • n are substituted with R 1 in formula (4-3). n has the same meaning as n in formula (4-3).
  • the hydrogen atoms in these structures may be further substituted with known substituents such as a hydroxy group and a hydrocarbon group.
  • Y 1 is a group containing a structure obtained by removing two or more hydrogen atoms from a structure represented by formula (V-4), Y 1 is preferably a group represented by formula (V-4-2) below.
  • * represents a bonding site with the two nitrogen atoms to which Y 1 in formula (4-3) is bonded
  • n1 represents an integer of 0 to 5.
  • An embodiment in which n1 is 0 is also one of the preferred embodiments of the present invention.
  • n are substituted with R 1 in formula (4-3).
  • n has the same meaning as n in formula (4-3).
  • the hydrogen atoms in the structure below may be further substituted with known substituents such as a hydroxy group and a hydrocarbon group.
  • Y 1 may be a group in which n hydrogen atoms have been removed from the group represented by R 131 in the above formula (4).
  • Y1 does not contain an imide structure in the structure. It is also preferred that Y1 does not contain a urethane bond, a urea bond or an amide bond in the structure. Furthermore, it is preferable that Y1 does not contain an ester bond in the structure.
  • Y1 does not contain an imide structure, a urethane bond, a urea bond, or an amide bond, and it is more preferable that Y1 does not contain an imide structure, a urethane bond, a urea bond, an amide bond, or an ester bond.
  • X 1 and Y 1 in formula (4-3) each include a structure in which two or more hydrogen atoms have been removed from a structure represented by any one of formulas (V-1) to (V-4) above.
  • n is preferably 1 or 2, and more preferably 2.
  • the polyimide has fluorine atoms in its structure.
  • the content of fluorine atoms in the polyimide is preferably 10% by mass or more, and more preferably 20% by mass or less.
  • the polyimide may be copolymerized with an aliphatic group having a siloxane structure.
  • diamine components include bis(3-aminopropyl)tetramethyldisiloxane and bis(p-aminophenyl)octamethylpentasiloxane.
  • the main chain ends of the polyimide are blocked with a terminal blocking agent such as a monoamine, an acid anhydride, a monocarboxylic acid, a monoacid chloride compound, or a monoactive ester compound.
  • a terminal blocking agent such as a monoamine, an acid anhydride, a monocarboxylic acid, a monoacid chloride compound, or a monoactive ester compound.
  • monoamine compounds include aniline, 2-ethynylaniline, 3-ethynylaniline, 4-ethynylaniline, 5-amino-8-hydroxyquinoline, 1-hydroxy-7-aminonaphthalene, 1-hydroxy-6-aminonaphthalene, 1-hydroxy-5-aminonaphthalene, 1-hydroxy-4-aminonaphthalene, 2-hydroxy-7-aminonaphthalene, 2-hydroxy-6-aminonaphthalene, 2-hydroxy-5-aminonaphthalene, 1-carboxy-7-aminonaphthalene, 1-carboxy-6-aminonaphthalene, 1-carboxy -5-aminonaphthalene, 2-carboxy-7-aminonaphthalene, 2-carboxy-6-aminonaphthalene, 2-carboxy-5-aminonaphthalene, 2-aminobenzoic acid, 3-aminobenzoic acid, 4-amino
  • the imidization rate of the polyimide (also referred to as the "ring closure rate") is preferably 70% or more, more preferably 80% or more, and even more preferably 90% or more. There is no particular upper limit to the imidization rate, and it is sufficient if it is 100% or less.
  • the imidization rate is measured, for example, by the following method. The infrared absorption spectrum of the polyimide is measured to determine the peak intensity P1 near 1377 cm ⁇ 1 , which is an absorption peak derived from the imide structure. Next, the polyimide is heat-treated at 350° C.
  • the weight average molecular weight (Mw) of the polyimide is preferably 5,000 to 100,000, more preferably 10,000 to 50,000, and even more preferably 15,000 to 40,000. By making the weight average molecular weight 5,000 or more, the folding resistance of the film after curing can be improved. In order to obtain an organic film having excellent mechanical properties (e.g., breaking elongation), the weight average molecular weight is particularly preferably 15,000 or more.
  • the number average molecular weight (Mn) of the polyimide is preferably from 2,000 to 40,000, more preferably from 3,000 to 30,000, and even more preferably from 4,000 to 20,000.
  • the polyimide preferably has a molecular weight dispersity of 1.5 or more, more preferably 1.8 or more, and even more preferably 2.0 or more.
  • the upper limit of the polyimide molecular weight dispersity is not particularly limited, but is, for example, preferably 7.0 or less, more preferably 6.5 or less, and even more preferably 6.0 or less.
  • the weight average molecular weight, number average molecular weight, and dispersity of at least one polyimide are within the above ranges. It is also preferable that the weight average molecular weight, number average molecular weight, and dispersity calculated by treating the multiple polyimides as one resin are each within the above ranges.
  • the polybenzoxazole precursor used in the present invention is not particularly limited with respect to its structure, but preferably contains a repeating unit represented by the following formula (3).
  • R 121 represents a divalent organic group
  • R 122 represents a tetravalent organic group
  • R 123 and R 124 each independently represent a hydrogen atom or a monovalent organic group.
  • R 123 and R 124 have the same definition as R 113 in formula (2), and the preferred range is also the same. That is, it is preferable that at least one of them is a polymerizable group.
  • R 121 represents a divalent organic group.
  • the divalent organic group is preferably a group containing at least one of an aliphatic group and an aromatic group.
  • the aliphatic group is preferably a linear aliphatic group.
  • R 121 is preferably a dicarboxylic acid residue. Only one type of dicarboxylic acid residue may be used, or two or more types may be used.
  • dicarboxylic acid residue a dicarboxylic acid residue containing an aliphatic group and a dicarboxylic acid residue containing an aromatic group are preferred, and a dicarboxylic acid residue containing an aromatic group is more preferred.
  • the dicarboxylic acid containing an aliphatic group is preferably a dicarboxylic acid containing a linear or branched (preferably linear) aliphatic group, and more preferably a dicarboxylic acid consisting of a linear or branched (preferably linear) aliphatic group and two -COOH groups.
  • suberic acid dodecafluorosuberic acid, azelaic acid, sebacic acid, hexadecafluorosebacic acid, 1,9-nonanedioic acid, dodecanedioic acid, tridecanedioic acid, tetradecanedioic acid, pentadecanedioic acid, hexadecanedioic acid, heptadecanedioic acid, octadecanedioic acid, nonadecanedioic acid, eicosanediacid, heneicosanediacid, docosanediacid, tricosanediacid, tetracosanediacid, pentacosanediacid, hexacosanediacid, heptacosanediacid, octacosanediacid, nonacosanediacid, triacontanedioic acid, hentri
  • Z is a hydrocarbon group having 1 to 6 carbon atoms, and n is an integer from 1 to 6.
  • dicarboxylic acids containing an aromatic group the following dicarboxylic acids having an aromatic group are preferred, and the following dicarboxylic acids consisting of a group having an aromatic group and two -COOH groups are more preferred.
  • dicarboxylic acids containing aromatic groups include 4,4'-carbonyldibenzoic acid, 4,4'-dicarboxydiphenyl ether, and terephthalic acid.
  • R 122 represents a tetravalent organic group.
  • the tetravalent organic group has the same meaning as R 115 in formula (2) above, and the preferred range is also the same.
  • R 122 is preferably a group derived from a bisaminophenol derivative.
  • Examples of the group derived from a bisaminophenol derivative include 3,3'-diamino-4,4'-dihydroxybiphenyl, 4,4'-diamino-3,3'-dihydroxybiphenyl, 3,3'-diamino-4,4'-dihydroxydiphenyl sulfone, 4,4'-diamino-3,3'-dihydroxydiphenyl sulfone, bis-(3-amino-4-hydroxyphenyl)methane, 2,2-bis(3-amino-4-hydroxyphenyl)propane, 2,2-bis-(3-amino-4-hydroxyphenyl)hexafluoropropane, 2,2-bis-(4-amino bis-(4-amino-3-hydroxyphenyl)hexafluoropropane, bis-(4-amino-3-hydroxyphenyl)methane, 2,2-bis-(4-amino-3-hydroxyphenyl)me
  • the following bisaminophenol derivatives having aromatic groups are preferred.
  • X1 represents -O-, -S-, -C( CF3 ) 2- , -CH2- , -SO2- or -NHCO-, and * and # each represent a bonding site with another structure.
  • R represents a hydrogen atom or a monovalent substituent, preferably a hydrogen atom or a hydrocarbon group, and more preferably a hydrogen atom or an alkyl group. It is also preferable that R122 represents a structure represented by the above formula.
  • R 122 is a structure represented by the above formula, of the total of four * and #, it is preferable that any two are bonding sites with the nitrogen atom to which R 122 in formula (3) is bonded, and the other two are bonding sites with the oxygen atom to which R 122 in formula (3) is bonded, and the two * are bonding sites with the oxygen atom to which R 122 in formula (3) is bonded, and the two # are bonding sites with the nitrogen atom to which R 122 in formula (3) is bonded, or it is more preferable that the two * are bonding sites with the nitrogen atom to which R 122 in formula (3) is bonded, and the two # are bonding sites with the oxygen atom to which R 122 in formula (3) is bonded, and it is even more preferable that the two * are bonding sites with the oxygen atom to which R 122 in formula (3) is bonded, and the two # are bonding sites with the nitrogen atom to which R 122 in formula (3) is bonded.
  • the bisaminophenol derivative is also preferably a compound represented by the formula (As).
  • R 1 is a hydrogen atom, alkylene, substituted alkylene, -O-, -S-, -SO 2 -, -CO-, -NHCO-, a single bond, or an organic group selected from the group represented by the following formula (A-sc).
  • R 2 is any one of a hydrogen atom, an alkyl group, an alkoxy group, an acyloxy group, and a cyclic alkyl group, and may be the same or different.
  • R 3 is any one of a hydrogen atom, a linear or branched alkyl group, an alkoxy group, an acyloxy group, and a cyclic alkyl group, and may be the same or different.
  • R 2 is an alkyl group and R 3 is an alkyl group, since this can maintain the effects of high transparency to i-line and a high cyclization rate when cured at a low temperature.
  • Z has an a-structure and a b-structure
  • R 1s is a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms
  • R 2s is a hydrocarbon group having 1 to 10 carbon atoms
  • at least one of R 3s , R 4s , R 5s , and R 6s is an aromatic group
  • the remaining are a hydrogen atom or an organic group having 1 to 30 carbon atoms, which may be the same or different.
  • Polymerization of the a-structure and the b-structure may be block polymerization or random polymerization.
  • the mol % of the Z portion is 5 to 95 mol % for the a-structure, 95 to 5 mol % for the b-structure, and a+b is 100 mol %.
  • preferred Z includes those in which R 5s and R 6s in the b structure are phenyl groups.
  • the molecular weight of the structure represented by formula (SL) is preferably 400 to 4,000, more preferably 500 to 3,000.
  • the diamine residue represented by formula (SL) is contained as another type of repeating unit, it is also preferable to further contain a tetracarboxylic acid residue remaining after removal of the anhydride group from the tetracarboxylic dianhydride as a repeating unit.
  • a tetracarboxylic acid residue include the examples of R 115 in formula (2).
  • R 134 represents a tetravalent organic group.
  • the tetravalent organic group include the examples of R 122 in the formula (3) of the polybenzoxazole precursor, and preferred examples are the same as those of R 122 .
  • the four bonds of the tetravalent organic group exemplified as R 122 bond to the nitrogen atom and oxygen atom in the above formula (X) to form a condensed ring.
  • R 134 is the following organic group, the following structure is formed.
  • * represents the bonding site with the nitrogen atom or oxygen atom in formula (X), respectively.
  • the oxazolization rate of the polybenzoxazole is preferably 85% or more, more preferably 90% or more.
  • the upper limit is not particularly limited, and may be 100%.
  • the oxazolization rate of 85% or more the film shrinkage due to ring closure that occurs when the film is oxazolized by heating is reduced, and the occurrence of warpage can be more effectively suppressed.
  • the oxazole ratio is measured, for example, by the following method.
  • the infrared absorption spectrum of the polybenzoxazole is measured, and the peak intensity Q1 at about 1650 cm ⁇ 1 , which is an absorption peak derived from the amide structure of the precursor, is determined.
  • R 117 is exemplified by a linear or branched aliphatic group, a cyclic aliphatic group, and an aromatic group, a heteroaromatic group, or a group in which two or more of these are linked by a single bond or a linking group.
  • a linear aliphatic group having 2 to 20 carbon atoms, a branched aliphatic group having 3 to 20 carbon atoms, a cyclic aliphatic group having 3 to 20 carbon atoms, an aromatic group having 6 to 20 carbon atoms, or a group in which two or more of these are combined by a single bond or a linking group is preferred, and an aromatic group having 6 to 20 carbon atoms, or a group in which two or more aromatic groups having 6 to 20 carbon atoms are combined by a single bond or a linking group is more preferred.
  • the acid value of the polyamideimide is preferably from 2 to 35 mgKOH/g, more preferably from 3 to 30 mgKOH/g, and even more preferably from 5 to 20 mgKOH/g.
  • the acid value is measured by a known method, for example, the method described in JIS K 0070:1992.
  • examples of the acid group contained in the polyamideimide include the same groups as the acid groups in the above-mentioned polyimides, and the preferred embodiments are also the same.
  • carboxylic acid chloride examples include acetyl chloride, acrylic acid chloride, propionyl chloride, methacrylic acid chloride, pivaloyl chloride, cyclohexanecarbonyl chloride, 2-ethylhexanoyl chloride, cinnamoyl chloride, 1-adamantanecarbonyl chloride, heptafluorobutyryl chloride, stearic acid chloride, and benzoyl chloride.
  • radical crosslinking agents include unsaturated carboxylic acids (e.g., acrylic acid, methacrylic acid, itaconic acid, crotonic acid, isocrotonic acid, maleic acid, etc.) and their esters and amides, preferably esters of unsaturated carboxylic acids and polyhydric alcohol compounds, and amides of unsaturated carboxylic acids and polyvalent amine compounds.
  • unsaturated carboxylic acids e.g., acrylic acid, methacrylic acid, itaconic acid, crotonic acid, isocrotonic acid, maleic acid, etc.
  • esters and amides preferably esters of unsaturated carboxylic acids and polyhydric alcohol compounds
  • amides of unsaturated carboxylic acids and polyvalent amine compounds amides of unsaturated carboxylic acids and polyvalent amine compounds.
  • addition reaction products of unsaturated carboxylic acid esters or amides having nucleophilic substituents such as hydroxyl groups, amino groups, and sul
  • the radical crosslinking agent is preferably dipentaerythritol triacrylate (commercially available products include KAYARAD D-330 (manufactured by Nippon Kayaku Co., Ltd.)), dipentaerythritol tetraacrylate (commercially available products include KAYARAD D-320 (manufactured by Nippon Kayaku Co., Ltd.) and A-TMMT (manufactured by Shin-Nakamura Chemical Co., Ltd.)), dipentaerythritol penta(meth)acrylate (commercially available products include KAYARAD D-310 (manufactured by Nippon Kayaku Co., Ltd.)), dipentaerythritol hexa(meth)acrylate (commercially available products include KAYARAD DPHA (manufactured by Nippon Kayaku Co., Ltd.) and A-DPH (manufactured by Shin-Nakamura Chemical Co., Ltd.)), and structures in
  • the acid value of the radical crosslinking agent having an acid group is preferably 0.1 to 300 mgKOH/g, more preferably 1 to 100 mgKOH/g. If the acid value of the radical crosslinking agent is within the above range, the agent has excellent handling properties during manufacturing and developability. In addition, the agent has good polymerizability. The acid value is measured in accordance with the description of JIS K 0070:1992.
  • the crosslinking agent U may have only one urea bond or one urethane bond, may have one or more urea bonds and one or more urethane bonds, may have no urethane bonds but two or more urea bonds, or may have no urea bonds but two or more urethane bonds.
  • the total number of urea bonds and urethane bonds in the crosslinking agent U is 1 or more, preferably 1 to 10, more preferably 1 to 4, and even more preferably 1 or 2.
  • the radical polymerizable group in the crosslinking agent U is not particularly limited, and examples thereof include a vinyl group, an allyl group, a (meth)acryloyl group, a (meth)acryloxy group, a (meth)acrylamide group, a vinylphenyl group, and a maleimide group. Of these, a (meth)acryloxy group, a (meth)acrylamide group, a vinylphenyl group, or a maleimide group is preferred, and a (meth)acryloxy group is more preferred.
  • the crosslinking agent U has two or more radically polymerizable groups, the structures of the respective radically polymerizable groups may be the same or different.
  • the alkyleneoxy group may be contained as a polyalkyleneoxy group in the crosslinking agent U.
  • the number of repetitions of the alkyleneoxy group is preferably 2 to 10, and more preferably 2 to 6.
  • crosslinking agent U has an amide group
  • the crosslinking agent U is such that at least one selected from the group consisting of the hydroxy group, alkyleneoxy group, amide group and cyano group and at least one radical polymerizable group contained in the crosslinking agent U are linked via a linking group containing a urea bond or a urethane bond (hereinafter, also referred to as "linking group L2-1").
  • the crosslinking agent U preferably contains an aromatic group.
  • the aromatic group is preferably directly bonded to a urea bond or a urethane bond contained in the crosslinking agent U.
  • the crosslinking agent U contains two or more urea bonds or urethane bonds, it is preferable that one of the urea bonds or urethane bonds is directly bonded to the aromatic group.
  • the aromatic group may be an aromatic hydrocarbon group or an aromatic heterocyclic group, or may have a structure in which these form a condensed ring, but is preferably an aromatic hydrocarbon group.
  • the "number of atoms (linking chain length) between a urea bond or a urethane bond and a polymerizable group” refers to the chain of atoms on the path connecting two atoms or groups of atoms to be linked that links these objects with the shortest length (minimum number of atoms).
  • the number of atoms (linking chain length) between the urea bond and the radical polymerizable group (methacryloyloxy group) is 2.
  • the molecular weight of the crosslinking agent U is preferably 100-2,000, more preferably 150-1500, and even more preferably 200-900.
  • the method for producing the crosslinking agent U is not particularly limited, but it can be obtained, for example, by reacting a compound having a radical polymerizable compound and an isocyanate group with a compound having at least one of a hydroxy group or an amino group.
  • a difunctional methacrylate or acrylate for the resin composition.
  • the compounds include triethylene glycol diacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, tetraethylene glycol diacrylate, PEG (polyethylene glycol) 200 diacrylate, PEG 200 dimethacrylate, PEG 600 diacrylate, PEG 600 dimethacrylate, polytetraethylene glycol diacrylate, polytetraethylene glycol dimethacrylate, dipropylene glycol diacrylate, tripropylene glycol diacrylate, neopentyl glycol diacrylate, neopentyl glycol dimethacrylate, 3-methyl-1,5-pentanediol diacrylate, 1,6-hexyl ...
  • EO ethylene oxide
  • PO propylene oxide
  • PO propylene oxide
  • PO propylene oxide
  • PEG200 diacrylate refers to polyethylene glycol diacrylate having a formula weight of about 200 for the polyethylene glycol chain.
  • a monofunctional radical crosslinking agent can be preferably used as the radical crosslinking agent.
  • the monofunctional radical crosslinking agent a compound having a boiling point of 100° C. or more under normal pressure is also preferred in order to suppress volatilization before exposure.
  • the difunctional or higher radical crosslinking agent include allyl compounds such as diallyl phthalate and triallyl trimellitate.
  • the radical crosslinking agent may be used alone or in combination of two or more. When two or more types are used in combination, it is preferable that the total amount is within the above range.
  • the resin composition of the present invention also preferably contains another crosslinking agent different from the above-mentioned radical crosslinking agent.
  • the other crosslinking agent refers to a crosslinking agent other than the above-mentioned radical crosslinking agent, and is preferably a compound having, in its molecule, a plurality of groups that promote a reaction to form a covalent bond with another compound in the composition or a reaction product thereof upon exposure to light by a photoacid generator or a photobase generator, and is preferably a compound having, in its molecule, a plurality of groups that promote, by the action of an acid or a base, a reaction to form a covalent bond with another compound in the composition or a reaction product thereof.
  • crosslinking agents include compounds having a structure in which an amino group-containing compound such as melamine, glycoluril, urea, alkylene urea, or benzoguanamine is reacted with formaldehyde or formaldehyde and alcohol, and the hydrogen atom of the amino group is replaced with an acyloxymethyl group, a methylol group, an ethylol group, or an alkoxymethyl group.
  • the method for producing these compounds is not particularly limited, and any compound having the same structure as the compound produced by the above method may be used.
  • the methylol groups of these compounds may be self-condensed to produce an oligomer.
  • a crosslinking agent using melamine is called a melamine-based crosslinking agent
  • a crosslinking agent using glycoluril, urea or alkylene urea is called a urea-based crosslinking agent
  • a crosslinking agent using alkylene urea is called an alkylene urea-based crosslinking agent
  • a crosslinking agent using benzoguanamine is called a benzoguanamine-based crosslinking agent.
  • the resin composition of the present invention preferably contains at least one compound selected from the group consisting of urea-based crosslinking agents and melamine-based crosslinking agents, and more preferably contains at least one compound selected from the group consisting of glycoluril-based crosslinking agents and melamine-based crosslinking agents described below.
  • R 100 represents an alkyl group or an acyl group.
  • R 101 and R 102 each independently represent a monovalent organic group and may be bonded to each other to form a ring.
  • Examples of compounds in which an alkoxymethyl group or an acyloxymethyl group is directly substituted on an aromatic group include compounds represented by the following general formula:
  • X represents a single bond or a divalent organic group
  • each of R104 independently represents an alkyl group or an acyl group
  • R103 represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, an aralkyl group, or a group that decomposes by the action of an acid to produce an alkali-soluble group (for example, a group that is eliminated by the action of an acid, a group represented by -C( R4 ) 2COOR5 (each of R4 independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and R5 represents a group that is eliminated by the action of an acid)).
  • R 5 in a group that decomposes under the action of an acid to generate an alkali-soluble group, a group that is eliminated by the action of an acid, and a group represented by -C(R 4 ) 2 COOR 5 include -C(R 36 )(R 37 )(R 38 ), -C(R 36 )(R 37 )(OR 39 ), -C(R 01 )(R 02 )(OR 39 ), etc.
  • R 36 to R 39 each independently represent an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, or an alkenyl group, and R 36 and R 37 may be bonded to each other to form a ring.
  • the alkyl group is preferably an alkyl group having 1 to 10 carbon atoms, and more preferably an alkyl group having 1 to 5 carbon atoms.
  • the alkyl group may be either linear or branched.
  • the above cycloalkyl group is preferably a cycloalkyl group having 3 to 12 carbon atoms, and more preferably a cycloalkyl group having 3 to 8 carbon atoms.
  • the cycloalkyl group may be a monocyclic structure or a polycyclic structure such as a condensed ring.
  • the aryl group is preferably an aromatic hydrocarbon group having 6 to 30 carbon atoms, and more preferably a phenyl group.
  • the above aralkyl group is preferably an aralkyl group having 7 to 20 carbon atoms, and more preferably an aralkyl group having 7 to 16 carbon atoms.
  • the above aralkyl group is intended to be an aryl group substituted with an alkyl group, and preferred embodiments of these alkyl and aryl groups are the same as those of the alkyl and aryl groups.
  • the alkenyl group is preferably an alkenyl group having 3 to 20 carbon atoms, and more preferably an alkenyl group having 3 to 16 carbon atoms. These groups may further have known substituents.
  • R 01 and R 02 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, or an alkenyl group.
  • the group that decomposes under the action of an acid to generate an alkali-soluble group, or the group that is eliminated under the action of an acid is preferably a tertiary alkyl ester group, an acetal group, a cumyl ester group, an enol ester group, etc. More preferably, it is a tertiary alkyl ester group or an acetal group.
  • a compound having at least one group selected from the group consisting of an acyloxymethyl group, a methylol group, an ethylol group, and an alkoxymethyl group a compound having at least one group selected from the group consisting of a urea bond and a urethane bond is also preferred.
  • the preferred aspects of the above compounds are the same as the preferred aspects of the crosslinker U, except that the polymerizable group is not a radically polymerizable group but is at least one group selected from the group consisting of an acyloxymethyl group, a methylol group, an ethylol group, and an alkoxymethyl group.
  • Specific examples of compounds having at least one group selected from the group consisting of an acyloxymethyl group, a methylol group, and an ethylol group include the following structures.
  • Compounds having an acyloxymethyl group include compounds in which the alkoxymethyl group in the following compounds has been changed to an acyloxymethyl group.
  • Compounds having an alkoxymethyl group or acyloxymethyl in the molecule include, but are not limited to, the following compounds.
  • urea-based crosslinking agents include glycoluril-based crosslinking agents such as monohydroxymethylated glycoluril, dihydroxymethylated glycoluril, trihydroxymethylated glycoluril, tetrahydroxymethylated glycoluril, monomethoxymethylated glycoluril, dimethoxymethylated glycoluril, trimethoxymethylated glycoluril, tetramethoxymethylated glycoluril, monoethoxymethylated glycoluril, diethoxymethylated glycoluril, triethoxymethylated glycoluril, tetraethoxymethylated glycoluril, monopropoxymethylated glycoluril, dipropoxymethylated glycoluril, tripropoxymethylated glycoluril, tetrapropoxymethylated glycoluril, monobutoxymethylated glycoluril, dibutoxymethylated glycoluril, tributoxymethylated glycoluril, and tetrabutoxymethylated glycoluril; Urea-based crosslinking agents such as
  • Such compounds include benzenedimethanol, bis(hydroxymethyl)cresol, bis(hydroxymethyl)dimethoxybenzene, bis(hydroxymethyl)diphenyl ether, bis(hydroxymethyl)benzophenone, hydroxymethylphenyl hydroxymethylbenzoate, bis(hydroxymethyl)biphenyl, dimethylbis(hydroxymethyl)biphenyl, bis(methoxymethyl)benzene, bis(methoxymethyl)cresol, bis(methoxymethyl)dimethoxybenzene, bis(methoxymethyl)diphenyl ether, bis(methoxymethyl)benzophenone, methoxymethylphenyl methoxymethylbenzoate, bis(methoxymethyl)biphenyl, dimethylbis(methoxymethyl)biphenyl, 4,4',4''-ethylidene tris[2,6-bis(methoxymethyl)phenol], 5,5'-[2,2,2-trifluoro-1-(trifluoromethyl)ethylidene]bis
  • crosslinking agents may be commercially available, and suitable commercially available products include 46DMOC, 46DMOEP (both manufactured by Asahi Organic Chemicals Co., Ltd.), DML-PC, DML-PEP, DML-OC, DML-OEP, DML-34X, DML-PTBP, DML-PCHP, DML-OCHP, DML-PFP, DML-PSBP, DML-POP, DML-MBOC, DML-MBPC, DML-MTrisPC, DML-BisOC-Z, DML-BisOCHP-Z, DML-BPC, DMLBisOC-P, DMOM-PC, DMOM-PTBP, DMOM-MBPC, TriML-P, and TriML-35XL.
  • 46DMOC 46DMOEP (both manufactured by Asahi Organic Chemicals Co., Ltd.)
  • DML-PC DML-PEP
  • DML-OC DML-OEP
  • DML-34X DML-PTBP
  • the resin composition of the present invention also preferably contains, as another crosslinking agent, at least one compound selected from the group consisting of epoxy compounds, oxetane compounds, and benzoxazine compounds.
  • the epoxy compound is preferably a compound having two or more epoxy groups in one molecule.
  • the epoxy group undergoes a crosslinking reaction at 200° C. or less, and does not undergo a dehydration reaction due to the crosslinking, so that film shrinkage is unlikely to occur. Therefore, the inclusion of the epoxy compound is effective in curing the resin composition at low temperatures and suppressing warping.
  • the epoxy compound preferably contains a polyethylene oxide group. This further reduces the elastic modulus and suppresses warping.
  • a polyethylene oxide group refers to a group having 2 or more repeating ethylene oxide units, and the number of repeating units is preferably 2 to 15.
  • epoxy compounds include, but are not limited to, bisphenol A type epoxy resins; bisphenol F type epoxy resins; alkylene glycol type epoxy resins or polyhydric alcohol hydrocarbon type epoxy resins such as propylene glycol diglycidyl ether, neopentyl glycol diglycidyl ether, ethylene glycol diglycidyl ether, butylene glycol diglycidyl ether, hexamethylene glycol diglycidyl ether, trimethylolpropane triglycidyl ether; polyalkylene glycol type epoxy resins such as polypropylene glycol diglycidyl ether; and epoxy group-containing silicones such as polymethyl(glycidyloxypropyl)siloxane.
  • bisphenol A type epoxy resins bisphenol F type epoxy resins
  • alkylene glycol type epoxy resins or polyhydric alcohol hydrocarbon type epoxy resins such as propylene glycol diglycidyl ether, neopentyl glycol diglycid
  • n is an integer from 1 to 5
  • m is an integer from 1 to 20.
  • n 1 to 2 and m is 3 to 7 in order to achieve both heat resistance and improved elongation.
  • --Oxetane compound compound having an oxetanyl group
  • the oxetane compound include compounds having two or more oxetane rings in one molecule, 3-ethyl-3-hydroxymethyloxetane, 1,4-bis ⁇ [(3-ethyl-3-oxetanyl)methoxy]methyl ⁇ benzene, 3-ethyl-3-(2-ethylhexylmethyl)oxetane, 1,4-benzenedicarboxylic acid-bis[(3-ethyl-3-oxetanyl)methyl]ester, etc.
  • Specific examples include the Aron Oxetane series (e.g., OXT-121, OXT-221) manufactured by Toagosei Co., Ltd., which may be used alone or in combination of two or more kinds.
  • -Benzoxazine compound compound having a benzoxazolyl group
  • Benzoxazine compounds are preferred because they undergo a crosslinking reaction derived from a ring-opening addition reaction, so that no degassing occurs during curing, and further, they reduce thermal shrinkage and suppress the occurrence of warping.
  • benzoxazine compounds include P-d type benzoxazine, F-a type benzoxazine (all trade names, manufactured by Shikoku Kasei Corporation), benzoxazine adducts of polyhydroxystyrene resins, and phenol novolac type dihydrobenzoxazine compounds. These may be used alone or in a mixture of two or more types.
  • Omnirad 907, Omnirad 369, Omnirad 369E, Omnirad 379EG (all manufactured by IGM Resins B.V.), IRGACURE 907, IRGACURE 369, and IRGACURE 379 (all manufactured by BASF) can be used.
  • photoacid generators examples include quinone diazide compounds, oxime sulfonate compounds, organic halide compounds, organic borate compounds, disulfone compounds, and onium salt compounds. From the viewpoints of sensitivity and storage stability, organic halogen compounds, oxime sulfonate compounds, and onium salt compounds are preferred, and from the viewpoints of the mechanical properties of the film to be formed, oxime esters are preferred.
  • Rb 3 is an alkyl group (having 1 to 24 carbon atoms, preferably 2 to 18 carbon atoms, and more preferably 3 to 12 carbon atoms), an aryl group (having 6 to 22 carbon atoms, preferably 6 to 18 carbon atoms, and more preferably 6 to 10 carbon atoms), an alkenyl group (having 2 to 24 carbon atoms, preferably 2 to 12 carbon atoms, and more preferably 2 to 6 carbon atoms), an arylalkyl group (having 7 to 23 carbon atoms, preferably 7 to 19 carbon atoms, and more preferably 7 to 12 carbon atoms), an arylalkenyl group (having 8 to 24 carbon atoms, preferably 8 to 20 carbon atoms, and more preferably 8 to 16 carbon atoms), an alkoxyl group (having 1 to 24 carbon atoms, preferably 2 to 18 carbon atoms, and more preferably 3 to 12 carbon atoms), an aryloxy group (having 6 to 22 carbon
  • R N1 and R N2 each independently represent a monovalent organic group
  • R C1 represents a hydrogen atom or a protecting group
  • L represents a divalent linking group
  • aliphatic hydrocarbon groups preferably having 1 to 24 carbon atoms, more preferably having 1 to 12 carbon atoms, and even more preferably having 1 to 10 carbon atoms
  • aromatic hydrocarbon groups preferably having 6 to 22 carbon atoms, more preferably having 6 to 18 carbon atoms, and even more preferably having 6 to 10 carbon atoms
  • R N1 and R N2 the basicity of the generated base is high, and this is preferable.
  • linear alkyl groups having an oxygen atom in the chain include an alkyloxyalkyl group, and preferred examples include a methyloxymethyl (MOM) group and an ethyloxyethyl (EE) group.
  • cyclic alkyl groups having an oxygen atom in the chain include an epoxy group, a glycidyl group, an oxetanyl group, a tetrahydrofuranyl group, and a tetrahydropyranyl (THP) group.
  • the divalent linking group constituting L is not particularly limited, but is preferably a hydrocarbon group, more preferably an aliphatic hydrocarbon group.
  • the hydrocarbon group may have a substituent, and may have an atom other than carbon atom in the hydrocarbon chain.
  • the divalent aliphatic hydrocarbon group preferably has 1 to 12 carbon atoms, more preferably 2 to 6 carbon atoms, and even more preferably 2 to 4 carbon atoms.
  • the divalent aromatic hydrocarbon group preferably has 6 to 22 carbon atoms, more preferably 6 to 18 carbon atoms, and even more preferably 6 to 10 carbon atoms.
  • Groups containing a combination of a divalent aliphatic hydrocarbon group and a divalent aromatic hydrocarbon group e.g., arylene alkyl groups
  • the linking group L is preferably a straight-chain or branched chain alkylene group, a cyclic alkylene group, a group containing a combination of a chain alkylene group and a cyclic alkylene group, an alkylene group having an oxygen atom in the chain, a straight-chain or branched chain alkenylene group, a cyclic alkenylene group, an arylene group, or an arylene alkylene group.
  • the linear or branched chain alkylene group preferably has 1 to 12 carbon atoms, more preferably 2 to 6 carbon atoms, and even more preferably 2 to 4 carbon atoms.
  • the cyclic alkylene group preferably has 3 to 12 carbon atoms, and more preferably has 3 to 6 carbon atoms.
  • the group containing a combination of a chain alkylene group and a cyclic alkylene group preferably has 4 to 24 carbon atoms, more preferably 4 to 12 carbon atoms, and even more preferably 4 to 6 carbon atoms.
  • the alkylene group having an oxygen atom in the chain may be linear or cyclic, and may be linear or branched.
  • the alkylene group having an oxygen atom in the chain preferably has 1 to 12 carbon atoms, more preferably 1 to 6 carbon atoms, and even more preferably 1 to 3 carbon atoms.
  • the linear or branched chain alkenylene group preferably has 2 to 12 carbon atoms, more preferably 2 to 6, and still more preferably 2 to 3.
  • the linear or branched chain alkenylene group preferably has 1 to 10 C ⁇ C bonds, more preferably 1 to 6, and still more preferably 1 to 3.
  • the cyclic alkenylene group preferably has 3 to 12 carbon atoms, and more preferably has 3 to 6 carbon atoms.
  • the cyclic alkenylene group preferably has 1 to 6 C ⁇ C bonds, and more preferably has 1 to 4 C ⁇ C bonds, and even more preferably has 1 or 2 C ⁇ C bonds.
  • the arylene group preferably has 6 to 22 carbon atoms, more preferably has 6 to 18 carbon atoms, and further preferably has 6 to 10 carbon atoms.
  • the arylene alkylene group preferably has 7 to 23 carbon atoms, more preferably has 7 to 19 carbon atoms, and further preferably has 7 to 11 carbon atoms.
  • Base generators include, but are not limited to, the following compounds:
  • the molecular weight of the nonionic base generator is preferably 800 or less, more preferably 600 or less, and even more preferably 500 or less.
  • the lower limit is preferably 100 or more, more preferably 200 or more, and even more preferably 300 or more.
  • Specific preferred compounds for the ionic base generator include, for example, the compounds described in paragraphs 0148 to 0163 of WO 2018/038002.
  • ammonium salts include, but are not limited to, the following compounds:
  • iminium salts include, but are not limited to, the following compounds:
  • the base generator is preferably an amine in which the amino group is protected by a t-butoxycarbonyl group, from the viewpoints of storage stability and generating a base by deprotection during curing.
  • Amine compounds protected by a t-butoxycarbonyl group include, for example, ethanolamine, 3-amino-1-propanol, 1-amino-2-propanol, 2-amino-1-propanol, 4-amino-1-butanol, 2-amino-1-butanol, 1-amino-2-butanol, 3-amino-2,2-dimethyl-1-propanol, 4-amino-2-methyl-1-butanol, valinol, 3-amino-1,2-propanediol, 2-amino-1,3-propanediol, Diol, tyramine, norephedrine, 2-amino-1-phenyl-1,3-propanediol, 2-aminocyclohexanol, 4-aminocyclohexanol, 4-aminocyclohexaneethanol, 4-(2-aminoethyl)cyclohexanol, N-
  • the resin composition of the present invention preferably contains a solvent.
  • the solvent may be any known solvent.
  • the solvent is preferably an organic solvent.
  • Examples of the organic solvent include compounds such as esters, ethers, ketones, cyclic hydrocarbons, sulfoxides, amides, ureas, and alcohols.
  • Esters for example, ethyl acetate, n-butyl acetate, isobutyl acetate, hexyl acetate, amyl formate, isoamyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl lactate, ethyl lactate, ⁇ -butyrolactone, ⁇ -caprolactone, ⁇ -valerolactone, ⁇ -valerolactone, alkyloxyacetates (for example, methyl alkyloxyacetate, ethyl alkyloxyacetate, butyl alkyloxyacetate (for example, methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, etc.)), 3-alkyloxypropionic acid alkyl esters (for example,
  • alkyloxypropionic acid alkyl esters include alkyl esters (e.g., methyl 2-alkyloxypropionate, ethyl 2-alkyloxypropionate, propyl 2-alkyloxypropionate, etc.
  • Suitable examples of ethers include ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol ethyl methyl ether, diethylene glycol butyl methyl ether, triethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, tetrahydrofuran, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol dimethyl ether, propylene glycol dimethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether, ethylene glycol monobutyl ether acetate, di
  • ketones include methyl ethyl ketone, cyclohexanone, cyclopentanone, 2-heptanone, 3-heptanone, 3-methylcyclohexanone, levoglucosenone, and dihydrolevoglucosenone.
  • cyclic hydrocarbons include aromatic hydrocarbons such as toluene, xylene, and anisole, and cyclic terpenes such as limonene.
  • dimethyl sulfoxide is preferred.
  • amides include N-methyl-2-pyrrolidone, N-ethyl-2-pyrrolidone, N-cyclohexyl-2-pyrrolidone, N,N-dimethylacetamide, N,N-dimethylformamide, N,N-dimethylisobutyramide, 3-methoxy-N,N-dimethylpropionamide, 3-butoxy-N,N-dimethylpropionamide, N-formylmorpholine, and N-acetylmorpholine.
  • ureas include N,N,N',N'-tetramethylurea and 1,3-dimethyl-2-imidazolidinone.
  • Alcohols include methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, benzyl alcohol, ethylene glycol monomethyl ether, 1-methoxy-2-propanol, 2-ethoxyethanol, diethylene glycol monoethyl ether, diethylene glycol monohexyl ether, triethylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monomethyl ether, polyethylene glycol monomethyl ether, polypropylene glycol, tetraethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monobenzyl ether, ethylene glycol monophenyl ether, methylphenyl carbinol, n-amyl alcohol, methylamyl alcohol, and diacetone alcohol.
  • An embodiment in which toluene is further added to these combined solvents in an amount of about 1 to 10% by mass based on the total mass of the solvent is also one of the preferred embodiments of the present invention.
  • an embodiment containing ⁇ -valerolactone as a solvent is one of the preferred embodiments of the present invention.
  • the content of ⁇ -valerolactone relative to the total mass of the solvent is preferably 50% by mass or more, more preferably 60% by mass or more, and even more preferably 70% by mass or more.
  • the upper limit of the content is not particularly limited and may be 100% by mass.
  • the content may be determined in consideration of the solubility of components such as a specific resin contained in the resin composition, etc.
  • the solvent preferably contains 60 to 90% by mass of ⁇ -valerolactone and 10 to 40% by mass of dimethyl sulfoxide, more preferably 70 to 90% by mass of ⁇ -valerolactone and 10 to 30% by mass of dimethyl sulfoxide, and even more preferably 75 to 85% by mass of ⁇ -valerolactone and 15 to 25% by mass of dimethyl sulfoxide, relative to the total mass of the solvent.
  • the second insulating pattern forming composition contains a solvent containing a carbonyl group as the solvent.
  • the solvent containing a carbonyl group includes the above-mentioned esters or ketones, and among these, a cyclic ester compound or a cyclic ketone compound is preferred, and it is preferable to include ⁇ -butyrolactone or cyclopentanone.
  • the solvent preferably contains at least one solvent selected from the group consisting of ⁇ -butyrolactone, PGMEA, and cyclopentanone.
  • the content of the solvent is preferably an amount that results in a total solids concentration of the resin composition of the present invention of 5 to 80 mass%, more preferably an amount that results in a total solids concentration of 5 to 75 mass%, even more preferably an amount that results in a total solids concentration of 10 to 70 mass%, and even more preferably an amount that results in a total solids concentration of 20 to 70 mass%.
  • the content of the solvent may be adjusted according to the desired thickness of the coating film and the coating method. When two or more types of solvents are contained, the total amount is preferably within the above range.
  • the resin composition of the present invention preferably contains a metal adhesion improver from the viewpoint of improving adhesion to metal materials used in electrodes, wiring, etc.
  • the metal adhesion improver include a silane coupling agent having an alkoxysilyl group, an aluminum-based adhesion aid, a titanium-based adhesion aid, a compound having a sulfonamide structure, a compound having a thiourea structure, a phosphoric acid derivative compound, a ⁇ -ketoester compound, an amino compound, and the like.
  • silane coupling agent examples include the compounds described in paragraph 0316 of International Publication No. 2021/112189 and the compounds described in paragraphs 0067 to 0078 of JP-A-2018-173573, the contents of which are incorporated herein.
  • Me represents a methyl group
  • Et represents an ethyl group.
  • R includes a structure derived from a blocking agent in a blocked isocyanate group.
  • the blocking agent may be selected according to the desorption temperature, and examples thereof include alcohol compounds, phenol compounds, pyrazole compounds, triazole compounds, lactam compounds, and active methylene compounds.
  • examples thereof include alcohol compounds, phenol compounds, pyrazole compounds, triazole compounds, lactam compounds, and active methylene compounds.
  • caprolactam and the like are preferred.
  • Commercially available products of such compounds include X-12-1293 (manufactured by Shin-Etsu Chemical Co., Ltd.).
  • silane coupling agents include, for example, vinyltrimethoxysilane, vinyltriethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-glycidoxypropyltriethoxysilane, p-styryltrimethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropyltriethoxysilane, 3-acryloxypropyltrimethoxysilane, N-2- (aminoethyl)-3-aminopropylmethyldimethoxysilane, N-2-(aminoethyl
  • an oligomer type compound having a plurality of alkoxysilyl groups can also be used as the silane coupling agent.
  • examples of such oligomer-type compounds include compounds containing a repeating unit represented by the following formula (S-1).
  • R 1 S1 represents a monovalent organic group
  • R 1 S2 represents a hydrogen atom, a hydroxyl group or an alkoxy group
  • n represents an integer of 0 to 2.
  • R S1 is preferably a structure containing a polymerizable group.
  • Examples of the polymerizable group include a group having an ethylenically unsaturated bond, an epoxy group, an oxetanyl group, a benzoxazolyl group, a blocked isocyanate group, and an amino group.
  • Examples of the group having an ethylenically unsaturated bond include a vinyl group, an allyl group, an isoallyl group, a 2-methylallyl group, a group having an aromatic ring directly bonded to a vinyl group (e.g., a vinylphenyl group), a (meth)acrylamide group, and a (meth)acryloyloxy group.
  • R S2 is preferably an alkoxy group, more preferably a methoxy group or an ethoxy group.
  • n represents an integer of 0 to 2, and is preferably 1.
  • n is 1 or 2 in at least one, more preferably that n is 1 or 2 in at least two, and further preferably that n is 1 in at least two.
  • oligomer type compounds commercially available products can be used, and an example of a commercially available product is KR-513 (manufactured by Shin-Etsu Chemical Co., Ltd.).
  • Aluminum-based adhesion promoter examples include aluminum tris(ethylacetoacetate), aluminum tris(acetylacetonate), and ethylacetoacetate aluminum diisopropylate.
  • the resin composition of the present invention preferably further contains a migration inhibitor.
  • a migration inhibitor for example, when the resin composition is applied to a metal layer (or metal wiring) to form a film, migration of metal ions derived from the metal layer (or metal wiring) into the film can be effectively suppressed.
  • the migration inhibitor examples include compounds having a heterocycle (pyrrole ring, furan ring, thiophene ring, imidazole ring, oxazole ring, thiazole ring, pyrazole ring, isoxazole ring, isothiazole ring, tetrazole ring, pyridine ring, pyridazine ring, pyrimidine ring, pyrazine ring, piperidine ring, piperazine ring, morpholine ring, 2H-pyran ring and 6H-pyran ring, triazine ring), thioureas and compounds having a sulfanyl group, hindered phenol compounds, salicylic acid derivative compounds, and hydrazide derivative compounds.
  • a heterocycle pyrrole ring, furan ring, thiophene ring, imidazole ring, oxazole ring, thiazole ring, pyrazole ring
  • Other migration inhibitors that can be used include the rust inhibitors described in paragraph 0094 of JP 2013-015701 A, the compounds described in paragraphs 0073 to 0076 of JP 2009-283711 A, the compounds described in paragraph 0052 of JP 2011-059656 A, the compounds described in paragraphs 0114, 0116, and 0118 of JP 2012-194520 A, and the compounds described in paragraph 0166 of WO 2015/199219 A, the contents of which are incorporated herein by reference.
  • migration inhibitors include the following compounds:
  • the content of the migration inhibitor is preferably 0.01 to 5.0 mass %, more preferably 0.05 to 2.0 mass %, and even more preferably 0.1 to 1.0 mass %, based on the total solid content of the resin composition.
  • the migration inhibitor may be one type or two or more types. When two or more types of migration inhibitors are used, it is preferable that the total is within the above range.
  • the resin composition of the present invention preferably contains a polymerization inhibitor, such as a phenolic compound, a quinone compound, an amino compound, an N-oxyl free radical compound, a nitro compound, a nitroso compound, a heteroaromatic ring compound, or a metal compound.
  • a polymerization inhibitor such as a phenolic compound, a quinone compound, an amino compound, an N-oxyl free radical compound, a nitro compound, a nitroso compound, a heteroaromatic ring compound, or a metal compound.
  • the content of the polymerization inhibitor is preferably 0.01 to 20 mass % relative to the total solid content of the resin composition, more preferably 0.02 to 15 mass %, and even more preferably 0.05 to 10 mass %.
  • the resin composition of the present invention also preferably contains a compound (light absorber) whose absorbance at the exposure wavelength decreases upon exposure.
  • Whether or not a certain compound a contained in a resin composition corresponds to a light absorbent can be determined by the following method. First, a solution of compound a is prepared at the same concentration as that contained in the resin composition, and the molar absorption coefficient of compound a at the wavelength of the exposure light (mol -1 ⁇ L ⁇ cm -1 , also called "molar absorption coefficient 1") is measured. The measurement is carried out quickly so as to reduce the influence of changes such as a decrease in the molar absorption coefficient of compound a.
  • the resin composition contains a solvent
  • that solvent is used as the solvent in the solution
  • N-methyl-2-pyrrolidone is used.
  • the solution of compound a is irradiated with exposure light, with the cumulative exposure dose being 500 mJ per mole of compound a.
  • the molar absorption coefficient (mol ⁇ 1 ⁇ L ⁇ cm ⁇ 1 , also referred to as “molar absorption coefficient 2”) of compound a at the wavelength of the exposure light is measured using the solution of compound a after exposure. From the above molar absorption coefficient 1 and molar absorption coefficient 2, the attenuation rate (%) is calculated based on the following formula.
  • Attenuation rate (%) 1 - molar extinction coefficient 2 / molar extinction coefficient 1 x 100
  • the attenuation rate is preferably 10% or more, and more preferably 20% or more. There is no particular lower limit to the attenuation rate, so long as it is 0% or more.
  • the wavelength of the exposure light may be any wavelength that exposes the photosensitive film.
  • the wavelength of the exposure light is preferably a wavelength to which the photopolymerization initiator contained in the resin composition has sensitivity.
  • the photopolymerization initiator has sensitivity to a certain wavelength, meaning that the photopolymerization initiator generates a polymerization initiating species when exposed to light of a certain wavelength.
  • the wavelength of the exposure light in terms of its light source, may include (1) semiconductor laser (wavelengths 830 nm, 532 nm, 488 nm, 405 nm, 375 nm, 355 nm, etc.), (2) metal halide lamp, (3) high-pressure mercury lamp, g-line (wavelength 436 nm), h-line (wavelength 405 nm), i-line (wavelength 365 nm), broad (three wavelengths of g, h, and i-lines), (4) excimer laser, KrF excimer laser (wavelength 248 nm), ArF excimer laser (wavelength 193 nm), F2 excimer laser (wavelength 157 nm), (5) extreme ultraviolet light; EUV (wavelength 13.6 nm), (6) electron
  • the wavelength of the exposure light may be selected from those to which the photopolymerization initiator has sensitivity, and preferably, h-line (wavelength 405 nm) or i-line (wavelength 365 nm), more preferably i-line (wavelength 365 nm).
  • surfactant various surfactants such as a fluorine-based surfactant, a silicone-based surfactant, a hydrocarbon-based surfactant, etc.
  • the surfactant may be a nonionic surfactant, a cationic surfactant, or an anionic surfactant.
  • the fluorine content in the fluorosurfactant is preferably 3 to 40 mass%, more preferably 5 to 30 mass%, and particularly preferably 7 to 25 mass%. Fluorine surfactants with a fluorine content within this range are effective in terms of uniformity of the coating film thickness and liquid saving, and also have good solubility in the composition.
  • a higher fatty acid derivative such as behenic acid or behenic acid amide may be added to the resin composition of the present invention, and the higher fatty acid derivative may be unevenly distributed on the surface of the resin composition of the present invention during drying after application.
  • the average particle size of the inorganic particles is preferably from 0.01 to 2.0 ⁇ m, more preferably from 0.02 to 1.5 ⁇ m, even more preferably from 0.03 to 1.0 ⁇ m, and particularly preferably from 0.04 to 0.5 ⁇ m.
  • the above average particle size of the inorganic particles is the primary particle size and also the volume average particle size.
  • the volume average particle size can be measured by a dynamic light scattering method using, for example, a Nanotrac WAVE II EX-150 (manufactured by Nikkiso Co., Ltd.). When the above measurements are difficult, the measurements can also be made by centrifugal sedimentation light transmission method, X-ray transmission method, or laser diffraction/scattering method.
  • titanium bis(triethanolamine) diisopropoxide titanium di(n-butoxide) bis(2,4-pentanedionate), titanium diisopropoxide bis(2,4-pentanedionate), titanium diisopropoxide bis(tetramethylheptanedionate), titanium diisopropoxide bis(ethylacetoacetate), etc.
  • Titanocene compounds For example, pentamethylcyclopentadienyltitanium trimethoxide, bis( ⁇ 5-2,4-cyclopentadiene-1-yl)bis(2,6-difluorophenyl)titanium, bis( ⁇ 5-2,4-cyclopentadiene-1-yl)bis(2,6-difluoro-3-(1H-pyrrol-1-yl)phenyl)titanium, and the like.
  • Monoalkoxytitanium compounds For example, titanium tris(dioctylphosphate) isopropoxide, titanium tris(dodecylbenzenesulfonate) isopropoxide, etc.
  • the organic titanium compound is preferably at least one compound selected from the group consisting of I) titanium chelate compounds, II) tetraalkoxytitanium compounds, and III) titanocene compounds.
  • titanium diisopropoxide bis(ethylacetoacetate), titanium tetra(n-butoxide), and bis( ⁇ 5-2,4-cyclopentadiene-1-yl)bis(2,6-difluoro-3-(1H-pyrrol-1-yl)phenyl)titanium are preferred.
  • an organic titanium compound When an organic titanium compound is included, its content is preferably 0.05 to 10 parts by mass, and more preferably 0.1 to 2 parts by mass, per 100 parts by mass of the specific resin. If the content is 0.05 parts by mass or more, the heat resistance and chemical resistance of the resulting cured pattern will be better, and if it is 10 parts by mass or less, the storage stability of the composition will be superior.
  • antioxidant By including an antioxidant as an additive, it is possible to improve the elongation properties of the cured film and the adhesion to the metal material.
  • examples of the antioxidant include phenol compounds, phosphite compounds, and thioether compounds. Specific examples of the antioxidant include the compounds described in paragraphs 0348 to 0357 of WO 2021/112189, the contents of which are incorporated herein by reference.
  • the anti-aggregating agents may be used alone or in combination of two or more.
  • the content of the anti-aggregation agent is preferably 0.01 mass % or more and 10 mass % or less, and more preferably 0.02 mass % or more and 5 mass % or less, relative to the total solid mass of the resin composition.
  • phenolic compounds examples include Bis-Z, BisP-EZ, TekP-4HBPA, TrisP-HAP, TrisP-PA, BisOCHP-Z, BisP-MZ, BisP-PZ, BisP-IPZ, BisOCP-IPZ, BisP-CP, BisRS-2P, BisRS-3P, BisP-OCHP, methylenetris-FR-CR, BisRS-26X (all trade names, manufactured by Honshu Chemical Industry Co., Ltd.), BIP-PC, BIR-PC, BIR-PTBP, and BIR-BIPC-F (all trade names, manufactured by Asahi Organic Chemicals Co., Ltd.).
  • the phenol-based compounds may be used alone or in combination of two or more.
  • the content of the phenol-based compound is preferably 0.01 mass % or more and 30 mass % or less, and more preferably 0.02 mass % or more and 20 mass % or less, relative to the total solid mass of the resin composition.
  • Examples of the other polymer compounds include siloxane resins, (meth)acrylic polymers copolymerized with (meth)acrylic acid, novolac resins, resol resins, polyhydroxystyrene resins, and copolymers thereof.
  • the other polymer compounds may be modified by introducing a crosslinking group such as a methylol group, an alkoxymethyl group, or an epoxy group.
  • the metal content of the resin composition of the present invention is preferably less than 5 ppm by mass (parts per million), more preferably less than 1 ppm by mass, and even more preferably less than 0.5 ppm by mass.
  • metals include sodium, potassium, magnesium, calcium, iron, copper, chromium, nickel, etc., but metals contained as complexes of organic compounds and metals are excluded. When multiple metals are contained, it is preferable that the total of these metals is within the above range.
  • methods for reducing metal impurities unintentionally contained in the resin composition of the present invention include selecting raw materials with a low metal content as the raw materials constituting the resin composition of the present invention, filtering the raw materials constituting the resin composition of the present invention, lining the inside of the apparatus with polytetrafluoroethylene or the like and performing distillation under conditions that suppress contamination as much as possible, etc.
  • the content of halogen atoms is preferably less than 500 mass ppm, more preferably less than 300 mass ppm, and even more preferably less than 200 mass ppm from the viewpoint of wiring corrosion.
  • those present in the form of halogen ions are preferably less than 5 mass ppm, more preferably less than 1 mass ppm, and even more preferably less than 0.5 mass ppm.
  • Halogen atoms include chlorine atoms and bromine atoms.It is preferable that the total of chlorine atoms and bromine atoms, or chlorine ions and bromine ions, is within the above range.
  • a preferred method for adjusting the content of halogen atoms is ion exchange treatment.
  • a conventionally known container can be used as the container for the resin composition of the present invention.
  • the container it is also preferable to use a multi-layer bottle whose inner wall is made of six types of six layers of resin, or a bottle with a seven-layer structure of six types of resin, in order to prevent impurities from being mixed into the raw materials or the resin composition of the present invention.
  • An example of such a container is the container described in JP 2015-123351 A.
  • the shape of the cured product can be selected according to the application, such as forming a protective film on the wall surface, forming a via hole for conduction, adjusting impedance, electrostatic capacitance or internal stress, and imparting a heat dissipation function.
  • the film thickness of the cured product (film made of the cured product) is preferably 0.5 ⁇ m or more and 150 ⁇ m or less.
  • the shrinkage percentage of the resin composition of the present invention when cured is preferably 50% or less, more preferably 45% or less, and even more preferably 40% or less.
  • the imidization reaction rate of the cured product of the resin composition of the present invention is preferably 70% or more, more preferably 80% or more, and even more preferably 90% or more. If it is 70% or more, the cured product may have excellent mechanical properties.
  • the elongation at break of the cured product of the resin composition of the present invention is preferably 30% or more, more preferably 40% or more, and even more preferably 50% or more.
  • the glass transition temperature (Tg) of the cured product of the resin composition of the present invention is preferably 180° C. or higher, more preferably 210° C. or higher, and even more preferably 230° C. or higher.
  • the resin composition of the present invention can be prepared by mixing the above-mentioned components.
  • the mixing method is not particularly limited, and can be a conventionally known method. Examples of the mixing method include mixing with a stirring blade, mixing with a planetary stirrer, mixing with a ball mill, and mixing by rotating a tank.
  • the temperature during mixing is preferably from 10 to 30°C, more preferably from 15 to 25°C.
  • the filter pore size is, for example, preferably 5 ⁇ m or less, more preferably 1 ⁇ m or less, even more preferably 0.5 ⁇ m or less, and even more preferably 0.1 ⁇ m or less.
  • the material of the filter is preferably polytetrafluoroethylene, polyethylene, or nylon. When the material of the filter is polyethylene, it is more preferable that it is HDPE (high density polyethylene).
  • the filter may be used after being washed in advance with an organic solvent. In the filter filtration process, multiple types of filters may be connected in series or parallel.
  • filters with different pore sizes or materials may be used in combination.
  • a connection mode an HDPE filter with a pore size of 1 ⁇ m as the first stage and an HDPE filter with a pore size of 0.2 ⁇ m as the second stage may be connected in series.
  • various materials may be filtered multiple times. When filtration is performed multiple times, circulation filtration may be performed. Filtration may also be performed under pressure.
  • the pressure to be applied is, for example, preferably 0.01 MPa or more and 1.0 MPa or less, more preferably 0.03 MPa or more and 0.9 MPa or less, even more preferably 0.05 MPa or more and 0.7 MPa or less, and even more preferably 0.05 MPa or more and 0.5 MPa or less.
  • impurity removal treatment using an adsorbent may be performed. Filter filtration and impurity removal treatment using an adsorbent may be combined.
  • the adsorbent a known adsorbent may be used.
  • inorganic adsorbents such as silica gel and zeolite, and organic adsorbents such as activated carbon may be used.
  • the resin composition filled in the bottle may be subjected to a degassing step by placing it under reduced pressure.
  • ⁇ resin ⁇ A-1 to A-10 Compounds having the following structure CA-1: Divinylbenzene/p-hydroxystyrene/styrene copolymer
  • the precipitate formed in the reaction mixture was removed by filtration to obtain a reaction liquid.
  • the reaction solution obtained was added to 3 L of ethyl alcohol to produce a precipitate consisting of a crude resin.
  • the produced crude resin was filtered and dissolved in 1.5 L of tetrahydrofuran to obtain a crude resin solution.
  • the crude resin solution obtained was dropped into 28 L of water to precipitate the resin, and the resulting precipitate was filtered and then dried in vacuum to obtain powdered resin A-1. It was confirmed by 1 H-NMR that the structure of resin A-1 was the structure represented by the above formula (A-5).
  • the subscripts in parentheses represent the content ratio (mol %) of the repeating unit.
  • the imidizable portion is imidized according to the above-mentioned imidization rate. These are the same in the following resins A-5 to A-9.
  • the weight average molecular weight (Mw) and imidization rate (%) of Resin A-5 are shown in the above table.
  • the weight average molecular weight (Mw) and imidization rate (%) of resin A-10 are also shown in the above table.
  • the subscripts of the repeating units represent the molar ratio of each repeating unit, b and d form a repeating unit with a or c, and a and c form a repeating unit with b or d or are bonded to e.
  • D-1 DPHA (dipentaerythritol hexaacrylate)
  • D-2 Compound having the following structure (OXT-121 (XDO), manufactured by Toagosei Co., Ltd.)
  • D-3 Compound having the following structure
  • G-1 Compound having the following structure
  • G-2 4-hydroxy-TEMPO free radical (Tokyo Chemical Industry Co., Ltd.)
  • G-3 Compound having the following structure
  • H-1 Compound having the following structure
  • H-2 8-azaadenine
  • M-1 N-phenyldiethanolamine (Tokyo Chemical Industry Co., Ltd.)
  • M-2 The following compound
  • the resin composition layer on the silicon wafer was exposed using an i-line stepper (Canon: FPR-3000i5) at the exposure amount shown in the "i-line exposure amount (mJ/cm 2 )" column of the table, and at the focus position shown in the "Focus ( ⁇ m)" column of the table (the surface of the resin composition layer opposite the silicon wafer is set to 0 ⁇ m, the inward direction of the resin composition layer is set to +, and the outward direction of the resin composition is set to -) through a mask formed with 1:1 line and space with a line width of 0.5 to 3.0 ⁇ m in increments of 0.05 ⁇ m.
  • the layer was heated as PEB (Post Exposure Bake) at the temperature and time shown in the "PEB (°C/min)” column of the table. Thereafter, the resist pattern was developed using the developer shown in the "Developer” column in the table for the time shown in the "Development Time (s)” column in the table, and then rinsed for 30 seconds with the rinse solution shown in the "Rinsing Solution” column in the table, to obtain a precursor pattern of an insulating pattern.
  • PEB Post Exposure Bake
  • Step C Plating CMP
  • the conductive layer formed in step B was polished using a CMP (Chemical Mechanical Polishing) machine manufactured by Fujikoshi Machinery Co., Ltd., using the slurry shown in the "Slurry used” column of "Step C” in the table, at the time and pressure shown in the "Polishing time (min.)” and “Polishing pressure (psi)” columns of “Step C” in the table, thereby exposing the Ti layer formed as a seed layer on the surface and the conductive pattern formed in the area between the insulating patterns.
  • 1 psi is 6.895 kPa.
  • Step D Barrier Metal CMP
  • a CMP (Chemical Mechanical Polishing) tool manufactured by Fujikoshi Machinery Co., Ltd. was used to polish the surface of the substrate 10 using the slurry shown in the "Slurry used” column of “Step D” in the table for the time shown in the "Polishing time (min.)” column of “Step D” in the table, until the second insulating pattern and the conductive pattern were exposed and flat.
  • Step E Post-polishing cure
  • Step F Formation of Surface Barrier Metal
  • a barrier metal layer having a thickness shown in the "Thickness (nm)” column of "Process F” in the table was formed on the surface of the conductive pattern using the material shown in the "Material type” column of "Process F” in the table.

Abstract

L'invention concerne un élément, un procédé de fabrication dudit élément, une composition de résine photosensible mettant en œuvre ledit procédé de fabrication d'élément, et un élément semi-conducteur contenant ledit élément. Plus précisément, l'invention concerne un élément qui possède un substrat, un motif d'isolation disposé sur ledit substrat, et un motif de conduction présent entre les motifs dudit motif d'isolation. Dans une direction perpendiculaire à la surface du substrat, la différence entre la valeur maximale et la valeur minimale de la distance depuis la surface du substrat jusqu'à la surface dudit motif de conduction côté opposé au substrat, est inférieure ou égale à ５００ｎｍ. Pour le motif de conduction, l'aire de sa surface côté opposé au substrat, est supérieure à son aire en une position à ５００ｎｍ de profondeur depuis ladite surface.
PCT/JP2023/046201 2022-12-28 2023-12-22 Élément ainsi que procédé de fabrication de celui-ci, composition de résine photosensible, et élément semi-conducteur WO2024143211A1 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP2022-212214 2022-12-28

Publications (1)

Publication Number Publication Date
WO2024143211A1 true WO2024143211A1 (fr) 2024-07-04

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