WO2021167077A1 - 感光性樹脂組成物の製造方法 - Google Patents
感光性樹脂組成物の製造方法 Download PDFInfo
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- WO2021167077A1 WO2021167077A1 PCT/JP2021/006410 JP2021006410W WO2021167077A1 WO 2021167077 A1 WO2021167077 A1 WO 2021167077A1 JP 2021006410 W JP2021006410 W JP 2021006410W WO 2021167077 A1 WO2021167077 A1 WO 2021167077A1
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/42—Polyamides containing atoms other than carbon, hydrogen, oxygen, and nitrogen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/36—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino acids, polyamines and polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
- C08G69/28—Preparatory processes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/40—Polyamides containing oxygen in the form of ether groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/22—Polybenzoxazoles
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/20—Exposure; Apparatus therefor
- G03F7/22—Exposing sequentially with the same light pattern different positions of the same surface
Definitions
- the present invention relates to a method for producing a photosensitive resin composition.
- a polyamide resin having a specific structure has been preferably used as a surface protective film or an interlayer insulating film of a semiconductor element because of its high heat resistance, electrical characteristics, and mechanical characteristics.
- a polyamide resin when such a polyamide resin is used as a protective film or an interlayer insulating film for a semiconductor element, it is common to dissolve the polyamide resin in an organic solvent and use it as a varnish from the viewpoint of improving process efficiency. It was a target.
- Patent Document 1 a photosensitive resin composition in which a polyimide precursor or a polybenzoxazole precursor and a polar solvent having a specific structure are combined is disclosed, and N-methyl- in the photosensitive resin composition is disclosed. It is disclosed that by adjusting the content of 2-pyrrolidone to 0.1% by mass or less, a resin composition that does not gel over time and satisfies the sensitivity and mechanical properties can be obtained.
- Patent Document 1 from the viewpoint of reducing the burden on the environment, an appropriate solvent or the like is selected in order to reduce the content of N-methyl-2-pyrrolidone in the resin composition.
- this N-methyl-2-pyrrolidone is used as a so-called synthetic solvent.
- an operation of washing the organic layer is performed in order to reduce N-methyl-2-pyrrolidone after the reaction. Such an operation causes the process to become complicated, and there is a concern that N-methyl-2-pyrrolidone may remain when the scale is increased.
- the present invention provides a production method for stably obtaining a photosensitive resin composition having a reduced burden on the environment.
- a method for producing a photosensitive resin composition containing a precursor having an amide bond having a repeating unit represented by the following general formula (1) is A step of activating the carboxylic acid compound represented by the following general formula (2) to obtain a carboxylic acid activated product, and The step of reacting the carboxylic acid activated product with an amine compound represented by the following general formula (3) to obtain a precursor having the amide bond is included.
- a photosensitive resin composition, wherein at least one of the steps of obtaining a carboxylic acid activated product and the step of obtaining a precursor having an amide bond is carried out in a solvent containing a heterocyclic compound having a carbonyl group. Manufacturing method is provided.
- R 1 is a hydroxyl group, —OR 3 , an alkyl group, an acyloxy group, or a cycloalkyl group, and when they have a plurality of groups, they are the same.
- R 2 is a hydroxyl group, a carboxyl group, -OR 3 or -COO-R 3 , and when a plurality of them are present, they may be the same or different.
- R 3 in 1 and R 2 is an organic group having 1 to 15 carbon atoms.
- R 1 has no hydroxyl group
- at least one of R 2 is a carboxyl group.
- R 2 has no carboxyl group, it is a carboxyl group.
- At least one of R 1 is a hydroxyl group.
- M is an integer of 0 to 8 and n is an integer of 0 to 8.
- the method is A step of activating the carboxylic acid compound represented by the following general formula (2) to obtain a carboxylic acid activated product, and The step of reacting the carboxylic acid activated product with an amine compound represented by the following general formula (3) to obtain a precursor having the amide bond is included.
- a photosensitive resin composition wherein at least one of the steps of obtaining a carboxylic acid activated product and the step of obtaining a precursor having an amide bond is carried out in a solvent containing a heterocyclic compound having a carbonyl group. Manufacturing method.
- R 1 is a hydroxyl group, —OR 3 , an alkyl group, an acyloxy group, or a cycloalkyl group, and when they have a plurality of groups, they are the same.
- R 2 is a hydroxyl group, a carboxyl group, -OR 3 or -COO-R 3 , and when a plurality of them are present, they may be the same or different.
- R 3 in 1 and R 2 is an organic group having 1 to 15 carbon atoms.
- R 1 has no hydroxyl group
- at least one of R 2 is a carboxyl group.
- R 2 has no carboxyl group, it is a carboxyl group.
- At least one of R 1 is a hydroxyl group.
- M is an integer of 0 to 8 and n is an integer of 0 to 8.
- the precursor having an amide bond in the present embodiment has a structure represented by the above general formula (1) (hereinafter, this precursor is also referred to as "polyamide resin").
- this precursor is also referred to as "polyamide resin"
- R 1 and R 2 a group in which the hydroxyl group and the carboxyl group are protected by the protecting group R 3 can be used in adjusting the solubility of the polyamide resin in an alkaline aqueous solution.
- -OR 3 as R 1 and -OR 3 and -COO-R 3 as R 2 can be used.
- Examples of such an organic group having 1 to 15 carbon atoms as R 3 include a formyl group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tertiary butyl group, a tertiary butoxycarbonyl group, a phenyl group and a benzyl group. Examples thereof include a tetrahydrofuranyl group and a tetrahydropyranyl group.
- the organic group as X in the general formula (1) is not particularly limited, but is, for example, an aromatic group having a structure such as a benzene ring, a naphthalene ring and a bisphenol structure; a structure such as a pyrrole ring and a furan ring. Heterocyclic organic group consisting of; siloxane group and the like can be mentioned. More specifically, the one represented by the following formula (12) is preferable. These may be used alone or in combination of two or more, if necessary.
- R 5 is a single bond, an alkyl group, one selected from an alkyl ester group and a halogen atom They may be the same or different, respectively.
- R 6 indicates one selected from a hydrogen atom, an alkyl group, an alkyl ester group and a halogen atom.
- U is an integer of 0 to 4. 7 to R 10 are monovalent or divalent organic groups, respectively.
- the substituents R 1 of X in the general formula (1) is omitted.
- Z is an alkylene group, a substituted alkylene group, -O-, -S-, -SO 2 -,-.
- R 11 is one selected from an alkyl group, an alkoxy group, an acyloxy group and a cycloalkyl group, and when there are a plurality of R 11 , they may be the same or different.
- V is an integer of 0 or more and 3 or less. Is.
- -CH 2- , -CH (CH 3 )-, and -C (CH 3 ) 2- are more well-balanced resins that have sufficient solubility not only in alkaline aqueous solutions but also in solvents. It is preferable because a film can be obtained.
- Y in the above general formula (1) is an organic group, and examples of such an organic group include the same as the above X.
- an aromatic group having a structure such as a benzene ring, a naphthalene ring and a bisphenol structure
- a heterocyclic organic group having a structure such as a pyrrole ring, a pyridine ring and a furan ring
- a siloxane group and the like can be mentioned, and more specifically.
- Those represented by the following formula (15) can be preferably mentioned. These may be used alone or in combination of two or more.
- R 13 is an alkyl group, an alkyl ester group, an alkyl ether. It indicates one selected from a group, a benzyl ether group and a halogen atom, which may be the same or different, respectively.
- R 14 indicates one selected from a hydrogen atom, an alkyl group, an alkyl ester group and a halogen atom.
- w is an integer of 0 or more and 2 or less.
- R 15 to R 18 are monovalent or divalent organic groups, respectively. In the above formula (15), the substituent R 2 of Y in the general formula (1) is omitted. )
- Particularly preferable among the groups represented by these formulas (15), include those represented by the following formula (16).
- the structure may include a meta position and a para position, respectively.
- R 19 is an alkyl group, an alkyl ester group, an alkyl ether group, a benzyl ether group and a halogen atom. Represents one selected, which may be the same or different.
- R 20 indicates one selected from a hydrogen atom or an organic group having 1 or more and 15 or less carbon atoms, even if a part is substituted. Good.
- X is an integer greater than or equal to 0 and less than or equal to 2.
- the precursor having the above-mentioned amide bond is produced through the following steps.
- Step 1 A step of activating the carboxylic acid compound represented by the general formula (2) to obtain a carboxylic acid activated product.
- Step 2 A step of allowing an amine compound represented by the general formula (3) to act on a carboxylic acid activated product to obtain a precursor having an amide bond. That is, in the present embodiment, the carboxylic acid compound represented by the general formula (2) is appropriately molecularly converted and then condensed with the amine compound represented by the general formula (3) to have a desired amide bond. It is for obtaining a precursor.
- Step 1 the carboxylic acid compound represented by the general formula (2) is activated to obtain a carboxylic acid activated product. That is, in this step, the reactivity of the carboxylic acid compound represented by the general formula (2) with the amine compound is improved by activating the provided carboxyl group.
- this step is an embodiment in which a carboxylic acid compound represented by the general formula (2) is halogenated to obtain an acid halide. That is, the carboxylic acid compound represented by the general formula (2) is subjected to any one of a fluorination treatment, a chlorination treatment, a bromination treatment and an iodide treatment to obtain an acid fluoride (acid). It is converted to one of fluoride), acid acidate (acid chloride), acid bromide (acid bromide), and acid iodide (acid iodide). Of these, in view of the availability of the reactant to be used and the like, chlorination treatment can be mentioned as a preferable embodiment.
- reactant used in the fluorination treatment known ones can be adopted, for example, alkali metal fluorides such as fluorine, potassium fluoride and lithium fluoride, and alkaline earth metal fluorides such as calcium fluoride. Quadruple ammonium fluorides such as isomers and tetrabutylammonium fluoride can be adopted.
- reactant used in the chlorination treatment known ones can be adopted, and for example, chlorine, thionyl chloride, oxalyl chloride, phosphorus trichloride and the like can be adopted.
- reactant used in the bromination treatment known ones can be adopted, and for example, bromine and aluminum tribromide can be adopted.
- reactant used in the iodination treatment known ones can be adopted, for example, alkali metal iodide such as iodine and potassium iodide, and [bis (trifluoroacetoxy) iodo] benzene should be adopted. Can be done.
- the conditions for using these reactants are arbitrary depending on the reactants adopted, but 90% or more of the carboxylic acid compound represented by the general formula (2) can be converted into an acid halide. It is preferable to adopt the conditions that can be achieved.
- step 1 there is an embodiment in which an ester compound is obtained by reacting a carboxylic acid compound represented by the general formula (2) with a compound having a hydroxyl group.
- the compound having a hydroxyl group a known alcohol compound can be adopted, and a compound such as methanol, ethanol, isopropanol, n-butanol, t-butyl alcohol, n-pentanol and the like can be adopted. Further, as the compound having this hydroxyl group, for example, 1-hydroxybenzotriazole or a derivative of this 1-hydroxybenzotriazole can also be used.
- ester compound When obtaining this ester compound, a condensing agent such as dicyclohexylcarbodiimide, which is used in ordinary ester synthesis, can be used.
- an acid catalyst such as hydrochloric acid, sulfuric acid, benzenesulfonic acid, or toluenesulfonic acid is added, and the mixture is heated to remove water generated from the alcohol compound and the carboxylic acid compound while advancing the reaction to promote esterification.
- the above ester compound can be obtained.
- the conditions for esterification are arbitrary depending on the reactants used, etc., but the conditions capable of converting 90% or more of the carboxylic acid compound represented by the general formula (2) into an ester compound are adopted. Is preferable.
- Step 2 Subsequently, the amine compound represented by the general formula (3) is allowed to act on the carboxylic acid activated product (acid halide or ester compound) obtained in step 1 to obtain a precursor having an amide bond.
- the temperature and time conditions for conversion to the precursor having an amide bond can be appropriately set according to the type of the carboxylic acid activator or the amine compound. Further, a known catalyst can be appropriately added from the viewpoint of accelerating the reaction.
- solvent In the method for producing a photosensitive resin composition of the present embodiment, at least one of the above steps 1 and 2 is carried out in a solvent containing a heterocyclic compound having a carbonyl group.
- the reactivity of the monomer molecule differs between the solvent having a heterocyclic compound having a carbonyl group and the solvent composed of a conventional acyclic compound.
- an acid anhydride endcap compound for terminating the reaction is reacted with the terminal amide group.
- the reaction of the end cap compound of the acid anhydride with the terminal amide group is appropriately controlled, and the reaction rate at the terminal is increased. improves.
- the heterocyclic compound having a carbonyl group has high solubility in a precursor having an amide bond and other resin components, and has an appropriate polarity. Therefore, in the above-mentioned step 1 or step 2, the heterocyclic compound has an appropriate polarity.
- the reaction can proceed smoothly. Further, in the steps 1 and 2, the same solvent may be used or different solvents may be used, but the same solvent is preferable from the viewpoint of improving productivity and reaction efficiency.
- heterocyclic compound having a carbonyl group examples include a 4-membered ring, a 5-membered ring, a 6-membered ring, a 7-membered ring, and the like, and among them, a 5-membered ring is preferable.
- These heterocyclic compounds having a carbonyl group may be partially substituted with a hydrocarbon group such as a methyl group, an ethyl group or a propyl group.
- examples of the heterocyclic compound having a carbonyl group include a compound containing a nitrogen atom in addition to the heterocycle (hereinafter, referred to as “carbonyl group-containing heterocyclic compound (i) having a nitrogen atom”).
- the photosensitive resin composition of the present embodiment better reactivity can be obtained by using the above-mentioned carbonyl group-containing heterocyclic compound (i) having a nitrogen atom, and the opening residue can be removed by appropriate solubility. Can be reduced.
- the heterocycle in the 5-membered heterocycle having the above carbonyl group is preferably one or more selected from furan, pyrrole, imidazole, oxazole, thiazole, and pyrazole, and the reaction is preferable. From the viewpoint of improving efficiency, it is more preferable to use one or more selected from pyrrole, imidazole, oxazole, thiazole, and pyrazole. Moreover, you may combine different kinds of heterocycles.
- examples of the furan having a carbonyl group include ⁇ -butyrolactone
- examples of the pyrrole having a carbonyl group include N-ethyl-2-pyrrolidone, as the imidazole having a carbonyl group.
- examples of the oxazole having a carbonyl group include 3-methyl-2-oxazolidone.
- N-ethyl-2-pyrrolidone, 3-methyl-2-oxazolidone and the like can be mentioned as an example of the above-mentioned carbonyl group-containing heterocyclic compound (i) having a nitrogen atom.
- solvent of this embodiment different kinds of solvents may be used in combination.
- a heterocyclic compound having a different type of carbonyl group may be used in combination, or a carbonyl group-containing heterocyclic compound (i) having a different type of the above nitrogen atom may be used in combination, or a heterocycle having a carbonyl group.
- a solvent other than the compound may be used.
- a compound usually used as a solvent can also be used in combination.
- a known solvent can be used as the solvent to be used in combination, but from the viewpoint of promoting reactivity and obtaining good solubility, a complex having no carbonyl group but containing a nitrogen atom in addition to the heterocycle. It is preferable to use a ring compound (iii) and a compound having a nitrogen atom and a carbonyl group (iii).
- the carbonyl group-containing heterocyclic compound (i) having the above-mentioned nitrogen atom and the above-mentioned carbonyl group-free but containing a nitrogen atom other than the heterocycle are contained.
- the heterocyclic compound (ii) may be used in combination, or the above-mentioned carbonyl group-containing heterocyclic compound (i) having a nitrogen atom and the compound having a nitrogen atom and a carbonyl group (iii) may be used in combination.
- the mixing ratio is preferably 1 to 40 parts by weight, preferably 1 to 40 parts by weight of the compound other than the heterocyclic compound having the carbonyl group with respect to 100 parts by weight of the heterocyclic compound having the carbonyl group of the present embodiment. More preferably, 1 to 30 parts by weight.
- such compounds include 2,6-lutidine, N, N-dimethylacetamide, 3-methoxy-N, N-dimethylpropionamide, dimethylsulfoxide, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, and diethylene glycol dibutyl ether.
- Propylene Glycol Monomethyl Ether Dipropylene Glycol Monomethyl Ether, Propylene Glycol Monomethyl Ether Acetate, Methyl Lactate, Ethyl Lactate, Butyl Lactate, Methyl-1,3-butylene Glycol Acetate, 1,3-butylene Glycol-3-monomethyl Ether, Pyrbin Examples thereof include methyl acid, ethyl pyruvate and methyl-3-methoxypropionate.
- step 1 or step 2 the above-mentioned heterocyclic compound having a carbonyl group is used as a solvent, but N-methyl-2-pyrrolidone is used as long as the object of the invention is not impaired. Can be included in this solvent.
- the content of N-methyl-2-pyrrolidone is preferably 80% by mass or less, more preferably 60% by mass or less, still more preferably 40% by mass or less, and 20% by mass, based on the whole solvent. It is particularly preferably 1% by mass or less, and particularly preferably 5% by mass or less. Furthermore, it is particularly preferred that N-methyl-2-pyrrolidone is substantially free of the solvent.
- this "substantially not contained” is used for the purpose of excluding the mode of intentionally adding N-methyl-2-pyrrolidone to this solvent, and in the manufacturing process, this N- Aspects in which contamination with methyl-2-pyrrolidone is unavoidable are acceptable.
- both the above-mentioned steps 1 and 2 are carried out in a solvent containing a heterocyclic compound having a carbonyl group. This makes it possible to simplify the process, and in some cases, it is possible to perform both step 1 and step 2 in one pot.
- a precursor having an amide bond is obtained at the stage where the above-mentioned step 2 is completed.
- the photosensitive resin composition can be obtained by substituting the solvent used in step 2 with another solvent, using the solvent used in step 2 as it is, or diluting it separately. ..
- various components used as the photosensitive resin composition can be blended.
- the alkali-soluble resin a component other than the precursor having the above-mentioned amide bond can be used in combination.
- examples of such an alkali-soluble resin include an acrylic resin such as a phenol resin, a phenol aralkyl resin, a hydroxystyrene resin, a methacrylic acid resin, and a methacrylic acid ester resin, and a cyclic olefin resin.
- the photosensitive resin composition is used as a so-called positive type, for example, a photosensitive diazoquinone compound, a diaryliodonium salt, an onium salt such as a triarylsulfonium salt or a sulfonium-borate salt, a 2-nitrobenzyl ester compound, N- A photoacid generator such as an iminosulfonate compound, an imidesulfonate compound, a 2,6-bis (trichloromethyl) -1,3,5-triazine compound, or a dihydropyridine compound can be blended.
- additives such as antioxidants, fillers, surfactants, photopolymerization initiators, end sealants and sensitizers may be added as needed. The amount of these added is arbitrary.
- the photosensitive resin composition obtained by the present embodiment can be cured to give a resin film.
- the obtained resin film can form, for example, a protective film, an interlayer film, or a permanent film such as a dam material. As a result, it is possible to improve the durability and the like of the electronic device provided with the resin film as a permanent film.
- the electronic device 100 shown in FIG. 1 is, for example, a semiconductor chip.
- a semiconductor package can be obtained by mounting the electronic device 100 on the wiring board via the bump 52.
- the electronic device 100 includes a semiconductor substrate provided with a semiconductor element such as a transistor, and a multilayer wiring layer provided on the semiconductor substrate (not shown).
- the uppermost layer of the multilayer wiring layer is provided with an interlayer insulating film 30 and an uppermost layer wiring 34 provided on the interlayer insulating film 30.
- the top layer wiring 34 is made of, for example, Al.
- a passivation film 32 is provided on the interlayer insulating film 30 and on the uppermost layer wiring 34. A part of the passivation film 32 is provided with an opening in which the uppermost layer wiring 34 is exposed.
- a rewiring layer 40 is provided on the passivation film 32.
- the rewiring layer 40 includes an insulating layer 42 provided on the passivation film 32, a rewiring 46 provided on the insulating layer 42, and an insulating layer 44 provided on the insulating layer 42 and the rewiring 46.
- the insulating layer 42 is formed with an opening for connecting to the uppermost layer wiring 34.
- the rewiring 46 is formed on the insulating layer 42 and in the openings provided in the insulating layer 42, and is connected to the uppermost layer wiring 34.
- the insulating layer 44 is provided with an opening for connecting to the rewiring 46.
- one or more of the passivation film 32, the insulating layer 42, and the insulating layer 44 can be composed of, for example, a resin film formed by curing the above-mentioned photosensitive resin composition.
- a coating film formed of a photosensitive resin material is exposed to ultraviolet rays, developed for patterning, and then heat-cured to form a passivation film 32, an insulating layer 42, or an insulating layer 44. It is formed.
- a bump 52 is formed in the opening provided in the insulating layer 44, for example, via a UBM (Under Bump Metallurgy) layer 50.
- the electronic device 100 is connected to a wiring board or the like via, for example, a bump 52.
- Example 1 In the procedure shown below, the solvent 1 was used in the proportion shown in Table 1 to obtain a precursor having an amide bond. Specifically, it is as follows. Moreover, the weight average molecular weight (Mw) and the number average molecular weight (Mn) of the obtained precursor having an amide bond were measured, and the results are shown in Table 1. Diphenyl ether-4,4'-dicarboxylic acid 258.2 g (1 mol) and 1-hydroxybenzotriazole 270.3 g (2 mol) were dissolved in solvent 1 (1500 g) and then dicyclohexyl dissolved in solvent 1 (412 g).
- thermometer and a stirrer were used to add 40.87 g (0.083 mol) of the obtained dicarboxylic acid derivative and 36.63 g (0.1 mol) of 2,2-bis (3-amino-4-hydroxyphenyl) hexafluoropropane.
- a four-port separable flask equipped with a raw material input port and a dry nitrogen gas introduction tube, and solvent 1 (180.8 g) was added to dissolve the flask. Then, while flowing nitrogen, the temperature was raised to 75 ° C. using an oil bath, and the reaction was carried out at 75 ° C. for 12 hours.
- the obtained precursor having an amide bond had the repeating unit (A-1) shown below.
- the precursor having an amide bond obtained above was dissolved again in solvent 1 and a photoacid generator was added to obtain a photosensitive resin composition.
- the photoacid generator was adjusted to be 15 parts by mass with respect to 100 parts by mass of the precursor having an amide bond
- the solvent 1 was adjusted to 100 parts by mass of the precursor (A-1) having an amide bond. It was adjusted to be 120 parts by mass.
- Examples 2 to 12 A precursor having an amide bond was obtained in the same manner as in Example 1 except that the solvent 1 used in Example 1 was changed to solvents 1 to 6 at the ratios shown in Table 1, and Mn and Mw thereof were respectively. I asked. Further, after that, the same operation as in Example 1 was carried out to obtain a photosensitive resin composition.
- solvents 1 to 6 are as follows.
- Solvent 1 N-ethyl-2-pyrrolidone solvent 2: 3-methyl-2-oxazolidone solvent 3: 3-methoxy-N, N-dimethylpropionamide solvent 4: ⁇ -butyrolactone solvent 5: 2,6-lutidine solvent 6 : Dimethyl sulfoxide
- a precursor having a desired amide bond was obtained by using a specific solvent. Further, by producing a photosensitive resin composition from this precursor, it was possible to stably obtain a photosensitive resin composition having a reduced burden on the environment.
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Abstract
Description
しかしながら、特許文献1の合成例1等として記載されている樹脂を作製する段階においては、このN-メチル-2-ピロリドンがいわゆる合成溶媒として用いられている。また、このような事情もあり、反応後にN-メチル-2-ピロリドンを低減するための、有機層の洗浄を行う操作がなされている。
このような操作はプロセスの煩雑化を招き、また、スケールアップを行った際ではN-メチル-2-ピロリドンが残存してしまうことが懸念される。
下記一般式(1)により示される繰り返し単位を有するアミド結合を有する前駆体を含む感光性樹脂組成物の製造方法であって、
当該方法は、
下記一般式(2)で表されるカルボン酸化合物を活性化し、カルボン酸活性化物を得る工程と、
前記カルボン酸活性化物に対して、下記一般式(3)で表されるアミン化合物を作用させ、前記アミド結合を有する前駆体を得る工程と、を含み、
カルボン酸活性化物を得る前記工程と、アミド結合を有する前駆体を得る前記工程の少なくとも一方は、カルボニル基を有する複素環化合物を含む溶媒中で行われることを特徴とする、感光性樹脂組成物の製造方法が提供される。
本実施形態に係る感光性樹脂組成物の製造方法は以下に示されるものである。
下記一般式(1)により示される繰り返し単位を有するアミド結合を有する前駆体を含む感光性樹脂組成物の製造方法であって、
当該方法は、
下記一般式(2)で表されるカルボン酸化合物を活性化し、カルボン酸活性化物を得る工程と、
前記カルボン酸活性化物に対して、下記一般式(3)で表されるアミン化合物を作用させ、前記アミド結合を有する前駆体を得る工程と、を含み、
カルボン酸活性化物を得る前記工程と、アミド結合を有する前駆体を得る前記工程の少なくとも一方は、カルボニル基を有する複素環化合物を含む溶媒中で行われることを特徴とする、感光性樹脂組成物の製造方法。
まず、本実施形態の製造方法において製造される感光性樹脂組成物に含まれるアミド結合を有する前駆体について説明する。
なお、上記式(12)において、上記一般式(1)におけるXの置換基R1は省略している。)
なお、上記式(15)において、上記一般式(1)におけるYの置換基R2は省略している。)
下記式(16)中のテトラカルボン酸二無水物由来の構造については、一般式(1)におけるC=O基に結合する位置が両方メタ位であるもの、両方パラ位であるものを挙げているが、メタ位とパラ位をそれぞれ含む構造でもよい。
(工程1)一般式(2)で表されるカルボン酸化合物を活性化し、カルボン酸活性化物を得る工程。
(工程2)カルボン酸活性化物に対して、一般式(3)で表されるアミン化合物を作用させ、アミド結合を有する前駆体を得る工程。
すなわち、本実施形態においては、一般式(2)で表されるカルボン酸化合物を適切に分子変換した上で、一般式(3)で表されるアミン化合物と縮合し、所望のアミド結合を有する前駆体を得るものである。
本工程においては、一般式(2)で表されるカルボン酸化合物を活性化し、カルボン酸活性化物を得る。
すなわち、本工程では、一般式(2)で表されるカルボン酸化合物について、備えられるカルボキシル基を活性化することにより、アミン化合物との反応性を向上させる。
すなわち、一般式(2)で表されるカルボン酸化合物に対して、フッ素化処理、塩素化処理、臭素化処理、ヨウ素化処理のいずれかを行うことにより、カルボン酸化合物を酸フッ化物(酸フルオリド)、酸塩化物(酸クロリド)、酸臭化物(酸ブロミド)、酸ヨウ化物(酸ヨージド)のいずれかへと変換する。
これらのうち、用いる反応剤の入手容易性等を鑑み、塩素化処理を行うことを好ましい態様として挙げることができる。
塩素化処理を行う際に用いる反応剤としては、公知のものを採用することができ、たとえば塩素、塩化チオニル、オキザリルクロリド、三塩化リン等を採用することができる。
臭素化処理を行う際に用いる反応剤としては、公知のものを採用することができ、たとえば臭素および三臭化アルミニウムを採用することができる。
ヨウ素化処理を行う際に用いる反応剤としては、公知のものを採用することができ、たとえばヨウ素、ヨウ化カリウム等のアルカリ金属ヨウ化物、[ビス(トリフルオロアセトキシ)ヨード]ベンゼンを採用することができる。
これらの反応剤を用いる際の条件は、採用される反応剤に応じて任意であるが、一般式(2)で表されるカルボン酸化合物の90%以上を酸ハロゲン化物へと変換することのできる条件を採用することが好ましい。
また、この水酸基を有する化合物としては、たとえば、1-ヒドロキシベンゾトリアゾールまたはこの1-ヒドロキシベンゾトリアゾールの誘導体等も用いることができる。
その他、塩酸、硫酸、ベンゼンスルホン酸、トルエンスルホン酸等の酸触媒を加えた上で、加熱し、アルコール化合物とカルボン酸化合物から発生する水を除去させつつ反応を進行させ、エステル化を進めて、上記のエステル化合物を得ることができる。
エステル化の条件は、採用される反応剤等に応じて任意であるが、一般式(2)で表されるカルボン酸化合物の90%以上をエステル化合物へと変換することのできる条件を採用することが好ましい。
続いて、工程1で得られたカルボン酸活性化物(酸ハロゲン化物あるいはエステル化合物)に対して、一般式(3)で表されるアミン化合物を作用させ、アミド結合を有する前駆体を得る。
また、反応を促進させる観点から適宜公知の触媒を加えることもできる。
本実施形態の感光性樹脂組成物の製造方法においては、上述の工程1および工程2の少なくとも一方は、カルボニル基を有する複素環化合物を含む溶媒中で行われる。
また、カルボニル基を有する5員環の複素環を有する溶媒を使用した場合、感光性樹脂のモノマー分子同士の反応性も同様に適度に制御され、分子量を増加しやすくできると考えられる。
なかでも、カルボニル基を有する複素環化合物として、5員環の複素環を選択したとき、かかる作用効果が顕著に得られる。
また、工程1および工程2において、同じ溶媒を用いてもよく、異なる溶媒を用いてもよいが、生産性・反応効率を向上させる観点から、同じ溶媒であることが好ましい。
また、カルボニル基を有する複素環化合物としては、当該複素環以外にさらに窒素原子を含む化合物(以下、「窒素原子を有するカルボニル基含有複素環化合物(i)」とする。)が挙げられる。本実施形態の感光性樹脂組成物は、上記の窒素原子を有するカルボニル基含有複素環化合物(i)を用いることで、より良好な反応性が得られ、適度な溶解性により、開口部残渣を低減できる。
なかでも、N-エチル-2-ピロリドン、3-メチル-2-オキサゾリドン等は、上記の窒素原子を有するカルボニル基含有複素環化合物(i)の一例として、挙げられる。
なお、感光性樹脂の分子量が増加する観点及び感光性樹脂のエンドキャップとの反応性が促進される観点から、γ-ブチロラクトンまたは3-メチル-2-オキサゾリドンの少なくとも一方を選択することが好ましい。
併用される溶媒としては、公知の溶媒を用いることができるが、反応性が促進され、良好な溶解性を得る観点から、カルボニル基を有さないが、当該複素環以外に窒素原子を含む複素環化合物(ii)、および、窒素原子およびカルボニル基を有する化合物(iii)を用いることが好適である。
また、良好な溶解性を保持する観点から、例えば、上記の窒素原子を有するカルボニル基含有複素環化合物(i)と、上記のカルボニル基を有さないが、当該複素環以外に窒素原子を含む複素環化合物(ii)とを併用すること、または、上記の窒素原子を有するカルボニル基含有複素環化合物(i)と、窒素原子およびカルボニル基を有する化合物(iii)とを併用してもよい。
このN-メチル-2-ピロリドンの含有量は溶媒全体に対して80質量%以下であることが好ましく、60質量%以下であることがより好ましく、40質量%以下であることがさらに好ましく、20質量%以下であることが殊更に好ましく、5質量%以下であることが特に好ましい。さらに、N-メチル-2-ピロリドンは溶媒に対して実質的に含まれていないことがとりわけ好ましい。
なお、この「実質的に含まれていない」とは、この溶媒に対してN-メチル-2-ピロリドンを意図的に添加する態様を排除する趣旨で用いており、製造プロセス上、このN-メチル-2-ピロリドンの混入を避けることが不可避である態様は許容するものである。
これによりプロセスの簡略化が可能となり、また、場合によっては、工程1と工程2の双方についてワンポットで行うことも可能となる。
これに対し、工程2で用いた溶媒を他の溶媒で置換するか、または、工程2で用いた溶媒をそのまま用いる、あるいはこれを別途希釈することにより、感光性樹脂組成物を得ることができる。
本実施形態では、上述した成分以外にも、感光性樹脂組成物として用いられる各種成分を配合することができる。
例えば、アルカリ可溶性樹脂として、前述のアミド結合を有する前駆体以外の成分を併用することができる。
このようなアルカリ可溶性樹脂としては、フェノール樹脂、フェノールアラルキル樹脂、ヒドロキシスチレン樹脂、メタクリル酸樹脂、メタクリル酸エステル樹脂等のアクリル系樹脂、環状オレフィン系樹脂等が挙げられる。
また、感光性樹脂組成物をいわゆるポジ型として用いる場合には、たとえば感光性ジアゾキノン化合物、ジアリールヨードニウム塩、トリアリールスルホニウム塩もしくはスルホニウム・ボレート塩などのオニウム塩、2-ニトロベンジルエステル化合物、N-イミノスルホネート化合物、イミドスルホネート化合物、2,6-ビス(トリクロロメチル)-1,3,5-トリアジン化合物、またはジヒドロピリジン化合物等の光酸発生剤を配合することができる。
その他、必要に応じて酸化防止剤、フィラー、界面活性剤、光重合開始剤、末端封止剤および増感剤等の添加物を添加してもよい。
なお、これらを添加する量は任意である。
本実施形態によって得られる感光性樹脂組成物は硬化することにより樹脂膜を与えることができる。得られる樹脂膜は、たとえば保護膜、層間膜、またはダム材等の永久膜を構成することができる。これにより、当該樹脂膜を永久膜として備える電子装置について、耐久性等の向上を図ることができる。
図1に示す電子装置100は、たとえば半導体チップである。この場合、たとえば電子装置100を、バンプ52を介して配線基板上に搭載することにより半導体パッケージが得られる。電子装置100は、トランジスタ等の半導体素子が設けられた半導体基板と、半導体基板上に設けられた多層配線層と、を備えている(図示せず)。多層配線層のうち最上層には、層間絶縁膜30と、層間絶縁膜30上に設けられた最上層配線34が設けられている。最上層配線34は、たとえばAlにより構成される。また、層間絶縁膜30上および最上層配線34上には、パッシベーション膜32が設けられている。パッシベーション膜32の一部には、最上層配線34が露出する開口が設けられている。
本実施形態においては、パッシベーション膜32、絶縁層42および絶縁層44のうちの一つ以上を、たとえば上述の感光性樹脂組成物を硬化することにより形成される樹脂膜により構成することができる。この場合、たとえば感光性樹脂材料により形成される塗布膜に対し紫外線を露光し、現像を行うことによりパターニングした後、これを加熱硬化することにより、パッシベーション膜32、絶縁層42または絶縁層44が形成される。
以下に示す手順で、表1に示される割合で溶媒1を用いて、アミド結合を有する前駆体を得た。具体的には、以下の通りである。また、得られたアミド結合を有する前駆体の重量平均分子量(Mw)、数平均分子量(Mn)を測定し、結果を表1に示した。
ジフェニルエーテル-4,4'-ジカルボン酸258.2g(1モル)と1-ヒドロキシベンゾトリアゾール270.3g(2モル)とを溶媒1(1500g)に溶解した後、溶媒1(412g)に溶解したジシクロヘキシルカルボジイミド412.7g(2モル)を内温0~5℃に保ちながら2時間かけて滴下した。滴下終了後、内温を室温に戻し更に12時間撹拌して反応させた。反応終了後、析出したジシクロヘキシルカルボジウレアを濾過によって取り除き、得られた濾液に純水4000gを滴下し、結晶を析出させた。この結晶を濾過によって採取し、イソプロピルアルコール8000mlを用いて洗浄した後、真空乾燥し、ジカルボン酸誘導体467gを得た。
得られたジカルボン酸誘導体40.87g(0.083モル)と、2,2-ビス(3-アミノ-4-ヒドロキシフェニル)ヘキサフルオロプロパン36.63g(0.1モル)とを温度計、攪拌機、原料投入口、乾燥窒素ガス導入管を備えた4つ口のセパラブルフラスコに入れ、溶媒1(180.8g)を加えて溶解させた。その後窒素を流しながら、オイルバスを用いて75℃まで昇温し、75℃にて12時間反応させた。次に、溶媒1(13.0g)に溶解させた3,6-エンドメチレン-1,2,3,6-テトラヒドロフタル酸無水物5.58g(0.034モル)を加え、さらに3時間攪拌した後、室温まで冷却し反応を終了した。
次に、反応混合物をろ過した後、反応混合物を水/イソプロピルアルコール=3/1の溶液に投入、沈殿物を濾集し水で充分洗浄した後、真空下で乾燥し、一般式(A-1)の繰り返し単位をもつアミド結合を有する前駆体(300~400℃で加熱すると脱水閉環し、ポリベンゾオキサゾールとなる樹脂)を得た。
実施例1で用いた溶媒1を、表1に示される割合で溶媒1~6に変更した以外は、実施例1と同様にして、アミド結合を有する前駆体を得、そのMn、Mwをそれぞれ求めた。
さらに、その後、実施例1と同様の操作を行い、感光性樹脂組成物を得た。
溶媒1:N-エチル-2-ピロリドン
溶媒2:3-メチル-2-オキサゾリドン
溶媒3:3-メトキシ-N,N-ジメチルプロピオンアミド
溶媒4:γ-ブチロラクトン
溶媒5:2,6-ルチジン
溶媒6:ジメチルスルホキシド
30 層間絶縁膜
32 パッシベーション膜
34 最上層配線
40 再配線層
42 絶縁層
44 絶縁層
46 再配線
50 UBM層
52 バンプ
Claims (7)
- 下記一般式(1)により示される繰り返し単位を有するアミド結合を有する前駆体を含む感光性樹脂組成物の製造方法であって、
当該方法は、
下記一般式(2)で表されるカルボン酸化合物を活性化し、カルボン酸活性化物を得る工程と、
前記カルボン酸活性化物に対して、下記一般式(3)で表されるアミン化合物を作用させ、前記アミド結合を有する前駆体を得る工程と、を含み、
カルボン酸活性化物を得る前記工程と、アミド結合を有する前駆体を得る前記工程の少なくとも一方は、カルボニル基を有する複素環化合物を含む溶媒中で行われることを特徴とする、感光性樹脂組成物の製造方法。
- 請求項1に記載の感光性樹脂組成物の製造方法であって、
カルボン酸活性化物を得る前記工程は、一般式(2)で表される前記カルボン酸化合物に対して、ハロゲン化処理をし、酸ハロゲン化物を得るものである、感光性樹脂組成物の製造方法。 - 請求項2に記載の感光性樹脂組成物の製造方法であって、
前記ハロゲン化処理は塩素化処理である、感光性樹脂組成物の製造方法。 - 請求項1に記載の感光性樹脂組成物の製造方法であって、
カルボン酸活性化物を得る前記工程は、一般式(2)で表されるカルボン酸化合物を、水酸基を有する化合物と反応させて、エステル化合物を得ることで行われる、感光性樹脂組成物の製造方法。 - 請求項4に記載の感光性樹脂組成物の製造方法であって、
水酸基を有する前記化合物は、1-ヒドロキシベンゾトリアゾールまたは1-ヒドロキシベンゾトリアゾール誘導体である、感光性樹脂組成物の製造方法。 - 請求項1ないし5のいずれか一項に記載の感光性樹脂組成物の製造方法であって、
カルボン酸活性化物を得る前記工程と、アミド結合を有する前駆体を得る前記工程の双方が、前記カルボニル基を有する複素環化合物を含む溶媒中で行われることを特徴とする、感光性樹脂組成物の製造方法。 - 請求項1ないし6のいずれか一項に記載の感光性樹脂組成物の製造方法であって、
前記カルボニル基を有する前記複素環は、フラン、ピロール、イミダゾール、オキサゾール、チアゾール、およびピラゾールの中から選ばれる1種または2種以上である、感光性樹脂組成物の製造方法。
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