WO2007100078A1 - スクリーン印刷用感光性インク組成物及びそれを用いたポジ型レリーフパターンの形成方法 - Google Patents
スクリーン印刷用感光性インク組成物及びそれを用いたポジ型レリーフパターンの形成方法 Download PDFInfo
- Publication number
- WO2007100078A1 WO2007100078A1 PCT/JP2007/054007 JP2007054007W WO2007100078A1 WO 2007100078 A1 WO2007100078 A1 WO 2007100078A1 JP 2007054007 W JP2007054007 W JP 2007054007W WO 2007100078 A1 WO2007100078 A1 WO 2007100078A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- diamine
- group
- polyimide
- bis
- composition according
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 39
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- 239000004642 Polyimide Substances 0.000 claims abstract description 88
- 150000004985 diamines Chemical class 0.000 claims abstract description 85
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 26
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 24
- 150000004984 aromatic diamines Chemical class 0.000 claims abstract description 8
- 239000003960 organic solvent Substances 0.000 claims abstract description 8
- -1 1-hydroxy 2,4 diaminobenzene 3,3 'dihydroxybenzidine Chemical compound 0.000 claims description 31
- 239000002904 solvent Substances 0.000 claims description 30
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 9
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Classifications
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/22—Secondary treatment of printed circuits
- H05K3/28—Applying non-metallic protective coatings
- H05K3/285—Permanent coating compositions
- H05K3/287—Photosensitive compositions
-
- 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
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- 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
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1057—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain
- C08G73/106—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain containing silicon
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/10—Block- or graft-copolymers containing polysiloxane sequences
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/22—Secondary treatment of printed circuits
- H05K3/28—Applying non-metallic protective coatings
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/452—Block-or graft-polymers containing polysiloxane sequences containing nitrogen-containing sequences
- C08G77/455—Block-or graft-polymers containing polysiloxane sequences containing nitrogen-containing sequences containing polyamide, polyesteramide or polyimide sequences
Definitions
- the present invention relates to a photosensitive ink composition for screen printing and a method for forming a positive relief pattern using the same.
- FPC, TAB, COF, and other flexible wiring boards have been manufactured as follows. First, a photosensitive film is laminated on “polyimide film Z adhesive Z copper foil” or a photosensitive resin is applied and dried, then exposed and developed to produce a laminate having a desired circuit pattern. Next, a thermosetting paste is generally applied and cured on the surface of the formed copper circuit pattern by an insulating protective film (covered film) or screen printing.
- a flexible printed wiring board protected with an insulating protective film is first drilled at a desired position on a cover lay film, such as a polyimide film with an adhesive on one side.
- a method of laminating a cover lay film with an opening on a flexible wiring board by heat lamination or pressing is common.
- Flexible printed wiring boards are made of polyester resin film, polyimide resin resin to protect the circuit. It is common to cover the surface with a film, etc. When the circuit width is 80 m or less and the distance between the circuits is 80 m or less, it is difficult to completely embed the adhesive in the irregularities between the circuits. is there.
- FCCLs flexible wiring boards
- circuit patterns are formed after holes and windows are formed in the joints between circuit terminals and parts in the coverlay film.
- the method of aligning with the above circuit has the problem of poor yield due to the limitations of workability and position accuracy.
- a predetermined cover lay film is formed by a method such as laser etching or plasma etching.
- a second method of drilling holes only at the position but the position accuracy is very good, but it has the drawbacks that it takes time to drill holes and the equipment and operating costs are high.
- a method of laminating using a photosensitive resin composition as a cover lay film a method of directly applying polyimide ink by screen printing, or a photosensitive film for photoresist.
- a method using a photosensitive cover lay film produced from a fat composition is known.
- a high concentration solution of polyamic acid partially imidized is applied to a substrate through a template, and the coating applied on the substrate is applied.
- a method for completely imidizing a membrane is known (Patent Document 1).
- the formed coating must be treated at a high temperature of 240 to 350 ° C in order to imidize it.
- large shrinkage of the formed polyimide resin is a major problem of workability, and it is difficult to form a dense patterned protective layer on a semiconductor wafer. It is difficult.
- Patent Document 1 and Patent Document 2 describe polyimides as pastes using a resin that is soluble in non-nitrogen-containing polar solvents and has low warpage and flexibility.
- Siloxane pastes are disclosed. Since these polyimide siloxane pastes have a low elastic modulus, they use diam having an expensive dimethylsiloxane bond as a starting material and are inferior in economic efficiency.
- PCT Posturesure Cooker Treatment resistance also decreases. is there.
- Patent Documents 3 and 4 disclose a solution composition of soluble polyimide siloxane and epoxy resin.
- This solution composition has the problem of poor chemical resistance due to the solvent solubility of polyimide. In addition, it dries quickly when screen printing, resulting in clogging of the screen mesh, resulting in marked pattern formation. There was also a practical problem that became difficult.
- Patent Document 5 discloses a soluble polyimide composition using diamine having a 10 mol% dimethylsiloxane bond. The coating film after drying in this composition is excellent in chemical resistance, heat resistance, adhesion to substrates and adhesive sheets, but is required to be improved in flexibility and warpage.
- Example 1 and 2 of Patent Document 6 a soluble polyimide composition using diamine having 33 mol% dimethylsiloxane bond is disclosed.
- Example 4 a soluble polyimide composition using diamine having 50 mol% dimethylsiloxane bond is disclosed. It has been. These have low warpage, chemical resistance, heat resistance, flexibility, and excellent adhesion to substrates and adhesive sheets after drying. In particular, printing workability is inferior.
- Pattern formation in a polyimide coating film for photoresist is performed by applying a polyamic acid precursor to a substrate and dissolving a photosensitive part (positive type) or a non-photosensitive part (negative type) by ultraviolet light exposure and development. Furthermore, a so-called photosensitive polyimide method, which is performed by imidizing the remaining polyamic acid, is known. However, the formed film is 240-3 for imidization. It is necessary to perform high-temperature treatment at 50 ° C.
- polyimide composition for example, dimerization by actinic radiation or a polymerizable carbon-carbon double bond and amino group or a quaternized salt thereof are added to polyamic acid.
- Compositions see Patent Document 7 or compositions obtained by adding acrylamide to polyamic acid (see Patent Document 8) are known.
- compositions obtained by adding a specific oxime compound and a sensitizer to a carbon-carbon double bond group-containing polyimide precursor is also known as a typical composition (see Patent Documents 9 to 5). These compositions have negative photosensitivity in which exposed portions remain after development, and all of them have been properly evaluated and utilized.
- a photosensitive polyimide composition comprising a composition in which polyimide is mixed with a photoinitiator, an imidation reaction with at least one acid dianhydride and at least one diamine is performed.
- a photosensitive polyimide composition (see Patent Document 12) characterized in that it contains a polyimide having a carboxyl group in the side chain and contains an aminoacrylamide compound as a reaction component with the carboxyl group.
- Patent Document 12 discloses a soluble polyimide composition using diamine having 1 to 10 mol% dimethylsiloxane bond.
- an organic polar solvent mainly composed of N-methyl 2-pyrrolidone, N, N-dimethylacetamide or N, N-dimethylformamide, acid dianhydride and diamine are present in the presence of a catalyst.
- printing work is particularly useful for developing printing ink applications that may cause problems such as whitening during printing and clogging of screen plates. Inferior.
- Patent Document 13 The applicant of the present application has previously filed a patent application for a photosensitive resin composition containing a block copolymerized polyimide (Patent Document 13).
- Patent Document 13 is excellent as an ink for screen printing.
- a photosensitive resin composition that exhibits excellent performance should be disclosed and suggested.
- Patent Document 1 Japanese Patent Application Laid-Open No. 7-304950
- Patent Document 2 JP-A-8-333455
- Patent Document 3 Japanese Patent Laid-Open No. 4-298093
- Patent Document 4 JP-A-6-157875
- Patent Document 5 Japanese Patent Laid-Open No. 2003-113338
- Patent Document 6 Japanese Patent Laid-Open No. 2003-119285
- Patent Document 7 Japanese Patent Publication No.59-52822
- Patent Document 8 JP-A-3-170555
- Patent Document 9 JP-A-61-118423
- Patent Document 10 Japanese Patent Laid-Open No. 62-184056
- Patent Document 11 Japanese Patent Laid-Open No. 62-273259
- Patent Document 12 Japanese Unexamined Patent Publication No. 2003-345007
- Patent Document 13 International Publication Gazette W099 / 19771
- An object of the present invention is to provide a film excellent in insulation, heat resistance, low warpage, low elasticity, and adhesion to a substrate when used as an ink for screen printing, and It is an object of the present invention to provide a photosensitive ink having excellent printing workability, which is less likely to cause defects such as screen clogging, blurring, blurring and chipping even after repeated screen printing.
- the present invention is a block containing, as a diamine component, a diamine having a siloxane bond in the molecular skeleton and an aromatic diamine having a hydroxyl group and a Z or carboxyl group in the ortho position relative to the amino group.
- the present inventors have found that a photosensitive polyimide resin composition containing a copolymerized polyimide as a resin component exhibits excellent printing workability when used as an ink for screen printing.
- the present invention provides a photosensitive ink composition for screen printing in which 100 parts by weight of an organic solvent-soluble block copolymerized polyimide and a photoacid generator 1 to: LOO parts by weight are dissolved in an organic solvent.
- the block copolymerized polyimide includes, as at least a part of a diamine component, a diamine having a siloxane bond in a molecular skeleton, and an aromatic having a hydroxyl group and a Z or carboxyl group in an ortho position with respect to an amino group.
- a photosensitive ink composition for screen printing comprising diam.
- the present invention provides a positive relief pattern in which the composition of the present invention is applied onto a substrate by screen printing, the active light source is irradiated in a pattern, and the irradiated portion is removed with an alkaline developer.
- a forming method is provided. The invention's effect
- the present invention it is possible to provide a film having excellent insulating properties, heat resistance, low warpage, low elasticity, and adhesion to a substrate, and clogging of the screen even when repeated screen printing is performed.
- a photosensitive ink excellent in printing workability that does not easily cause defects such as bleeding, blurring, and chipping has been provided.
- the block copolymerized polyimide used as the resin component in the photosensitive ink composition for screen printing of the present invention is a siloxane in the molecular skeleton (that is, in the main chain) as a part of the diamine component.
- a diamine having a bond hereinafter sometimes referred to as a “siloxane bond-containing diamine”.
- “comprising diamine” means that it contains a unit derived from the diamine obtained by polycondensation of the diamine with tetracarboxylic dianhydride. The amino group of diamine is used for an imide bond.
- siloxane bond-containing diamines include diamines having the structures represented by the following general formulas (I) and (IV).
- R, R, R and R are each independently an alkyl group or a cycloalkyl group.
- n ′ represents an integer of 1 to 30, preferably an integer of 1 to 20, and p in the formula (II) represents an integer of 1 to 4.
- R, R, R, and R are each independently an alkyl group having 1 to 6 carbon atoms.
- preferred are methyl group, ether group, propyl group, isopropyl group, butyl group, isobutyl group, benzyl group, hexyl group, cyclohexyl group, phenyl group, tolyl group, xylyl group.
- siloxane bond-containing diamines can be used as a mixture that can be used alone or in combination of two or more kinds.
- Commercially available products may be used as the siloxane bond-containing diamine, for example, those sold by Shin-Etsu Chemical Co., Ltd., Toray Dow Coung Co., and Chisso Corp. can be used as they are.
- KF-8010 manufactured by Shin-Etsu Chemical Co., Ltd. (amino group equivalent of about 450, in formula (I), R, R, R, R are methyl groups, 1 and m are 3
- R is a methyl group, 1 and m are 3), respectively.
- the content of the above siloxane bond-containing diamine in the block copolymerized polyimide is not particularly limited. Force All diamine components in the block copolymerized polyimide 15 to 85% by weight is preferable, and 35 to 80% by weight is more preferable.
- the siloxane bond-containing diamine is less than 15% by weight, the elongation rate of the polyimide ink coating film for screen printing is inferior and it is difficult to obtain sufficient flexibility.
- the block copolymerized polyimide used as the resin component is also an aromatic diamine (hereinafter referred to as "hydroxyl group") having a hydroxyl group and a Z or carboxyl group in the ortho position with respect to the amino group as a part of the diamine component.
- Z-carboxyl group-containing diamine a aromatic diamine
- each of the two amino groups of diamine has a hydroxyl group and a Z or carboxyl group at the ortho position, but the V group has a hydroxyl group and an ortho position relative to one of the amino groups. What is necessary is just to have Z or a carboxyl group.
- the hydroxyl group-Z carboxyl group-containing diamine is preferably a diamine containing two benzene rings in which an amino group and a hydroxyl group or a carboxyl group are bonded.
- hydroxyl group / carboxyl group-containing diamine examples include 2,2-bis (3-amino-4-hydroxyphenyl) propane, 1-hydroxy-1,2,4-diaminobenzene, 3, 3, -dihydroxybenzidine.
- 5 to 20% by weight is preferable with respect to all diamine components in the block copolymerized polyimide, and more preferably 7 to 15% by weight.
- the content of the hydroxyl group, Z carboxyl group-containing diamine is less than 5% by weight, the photosensitivity tends to decrease, and when it exceeds 20% by weight, film loss tends to occur.
- the block copolymerized polyimide may further contain one or more diamines other than these as a diamine component in addition to the above-mentioned siloxane bond-containing diamine and hydroxyl group Z force ruboxyl group-containing diamine.
- a diamine an aromatic diamine is usually used in order to improve the heat resistance of the polyimide, the adhesion to the conductor wire, and the degree of polymerization.
- aromatic diamines 9, 9'-bis (4-aminophenol) fluorene, m-phenol dirangeamine, p-phenylene diamine, 2, 4 diaminotoluene, 4, 4'-diamino-3, 3 ' Dimethyl-1,1'-biphenyl, 3,4'diaminodiphenyl ether, 4,4'-diaminodiphenyl ether, 3,3'-diaminodiphenylsulfone, 4,4'-diaminodiphenylsulfone, 4,4'-diaminodiphenyl- Rusulfide, 2,2 bis (4-aminophenol) propane, 2,2 bis (4-aminophenol) hexafluoropropane, 1,3 bis (3-aminophenoxy) benzene, 1,3 bis (4 aminophenoxy) Benzene, 1,4 bis (4-aminophenoxy) benzene, 4,4'-bis (4 aminophenoxy)
- aromatic tetracarboxylic dianhydride is usually used as the heat resistance of polyimide and compatibility with siloxane bond-containing diamine.
- 3, 3 ', 4, 4' biphenyltetracarboxylic dianhydride p-fere from the viewpoint of heat resistance of polyimide, adhesion of conductor wire, compatibility of diamine bond-containing diamine, polymerization rate Renbis (trimellitic acid monoester anhydride), ethylene glycol-bis-trimellitic anhydride ester), bis (3,4-dicarboxyphenyl) ether dianhydride, 3, 3 ', 4, 4' One benzophenone tetracarboxylic dianhydride and 3,3 ′, 4,4′-biphenylsulfone tetracarboxylic dianhydride are particularly preferred.
- These exemplified tetracarboxylic dianhydrides may be used alone or in combination of two or more.
- the block copolymerized polyimide may contain three or more blocks, but since the manufacturing process is complicated and the cost is increased, it is preferable that the block copolymer polyimide also has two blocking forces! /.
- the siloxane bond-containing diamine may be contained in two or more blocks in the block copolymerized polyimide.
- the inclusion of the siloxane bond-containing diamine in only one block has the viewpoint of printing workability.
- the diamine component in the one block can only be one type or two or more types of diamine bond-containing diamine! /, May! /, And one or more types of hydroxyl group Z carboxyl It may contain a group-containing diamine and Z or one or more other diamines described above.
- the hydroxyl group Z carboxyl group-containing diamine may be contained in two or more blocks, but may be contained in only one block.
- hydroxyl group Z carboxyl group-containing diamine When one type or two or more types of hydroxyl group Z carboxyl group-containing diamine is contained in one block, it may be contained in the same block as the siloxane bond-containing diamine, or may be contained in another block. When included in another block, the block may consist of only one kind or two or more kinds of hydroxyl group Z carboxyl group-containing diamine.
- Such a block copolymerized polyimide dehydrates and condenses one or more tetracarboxylic dianhydrides and one or more diamines in the presence of an acid catalyst composed of ratatones and a base.
- the polyimide obtained by the first-stage polycondensation step and the polyimide obtained by the first-stage polycondensation step are further mixed with one or two or more tetracarboxylic acid diacids in the presence of an acid catalyst consisting of rataton and basic force It is preferably produced by at least a two-stage polycondensation step including a second-stage polycondensation step in which a water product and one or more diamines are dehydrated and condensed.
- the two-stage polycondensation step preferably includes the above siloxane bond together with one or more tetracarboxylic dianhydrides and one or two or more hydroxyl groups Z carboxyl group-containing diamine.
- Diamine is heated and polycondensed in an organic polar solvent at 150-220 ° C in the presence of an acid catalyst to obtain a polyimide oligomer.
- the tetracarboxylic dianhydride component and Z or siloxane in the molecular skeleton are added to the oligomer. Without a bond, it can be obtained by polycondensation and chain extension of a diamine component.
- the first and second steps described above may be reversed, and as described above, only one or two or more siloxane bond-containing diamines are added as the diamine component in either step. Alternatively, only one or more diamine bond-containing diamines and one or more other diamines described above may be added. In addition, one or two or more kinds of hydroxyl group-Z carboxyl group-containing diamine may be added at either stage or at both stages.
- the molar ratio of the first stage diamine to tetracarboxylic dianhydride is 0.5 to 2.0, and the molar ratio of total diamine to total tetracarboxylic dianhydride is 0.95 to : L 05 is more preferable, and 0.98 to 1.02 is more preferable.
- a one-component base catalyst or a mixed catalyst composed of ratatones or acidic compounds and a base can be used.
- the one-component base catalyst include tertiary amines such as triethylamine and tributylamine, pyridine derivatives such as pyridine, 2-picoline and 2,3-lutidine, 1,4-dimethylbiperazine, Examples thereof include N-methylmorpholine.
- the mixed catalyst include a mixture of a rataton such as j8-petit-mouthed rataton or ⁇ -valerolataton, or an acidic compound such as crotonic acid or oxalic acid, and the basic compound described above.
- the mixing ratio of the acid and base of the acid-base catalyst is 1: 1 to 5 (molar equivalent), preferably 1: 1 to 2.
- Preferred catalysts are latatone and base or crotonic acid and basic force. This is a two-component composite catalyst.
- Preferred bases for latatones are ⁇ -valerolatataton, and pyridine or ⁇ -methylmorpholine is preferred.
- the mixing ratio of latatane or crotonic acid and base is 1: 1-5 (molar equivalent), preferably 1: 1-2.
- the amount of the one-component or mixed catalyst used is 1 to 100 to 1 to 5 mol, preferably 1 to 50 to 1 to 10 mol, based on the total tetracarboxylic dianhydride (total of the first and second stages).
- an organic solvent is used, and an organic polar solvent is preferably used.
- the organic polar solvent is preferably a rataton solvent such as ⁇ -ptyllactone, a benzoate solvent or an ether solvent, which is preferably used as the solvent for the ink composition of the present invention. It is desirable to use a solvent whose vapor pressure at room temperature is 3 mmHg or less, more preferably ImmHg or less, in order to take into account the screen plate making, clogging, and the like.
- the benzoate solvent examples include methyl benzoate, benzoate ether, butyl benzoate, and examples of the ether solvent include triethylene glycol dimethyl ether and tetraethylene glycol dimethyl ether.
- a solvent which can be azeotropically distilled off with water.
- examples of such a solvent include aromatic compounds such as benzene, alkylbenzenes such as toluene and xylene, and alkoxybenzenes such as methoxybenzene.
- the reaction conditions for the first stage are 150 to 220 ° C and the reaction time is not particularly limited, but is usually about 0.5 to 3 hours.
- the generated water is preferably continuously removed from the system by azeotropic distillation.
- tetracarboxylic dianhydride component and diamine component used as the tetracarboxylic dianhydride component and diamine component used. These may be the same as or different from those used in the first stage, but preferably at least the diamine component is not the same as the diamine component used in the first stage (same as the first stage). May contain different diamine components, but may contain different diamine components).
- the force described in the examples Add a predetermined amount of tetracarboxylic dianhydride, diamine compound and solvent used in the second stage, and react at 150-220 ° C as in the first stage. .
- the generated water is continuously removed from the system by azeotropy. If water no longer forms, remove it completely. If it is not completely distilled off at this time, it is not preferable because it volatilizes during printing and causes a change in viscosity and contamination of the environmental atmosphere.
- the reaction time is not particularly limited, but is usually about 3 to 8 hours.
- the polymerization reaction can be monitored by viscosity measurement and Z or GPC measurement. .
- the weight average molecular weight of the polyimide is preferably 20,000 to 200,000, more preferably 30,000 to 50,000.
- an aromatic amine such as aniline anhydride such as phthalic anhydride as a terminal terminator.
- a solvent-soluble block copolymerized polyimide can be obtained.
- the solid concentration at this time is preferably 10 to 50% by weight, more preferably 20 to 35% by weight.
- a ketone solvent can be used.
- ketone solvents include methyl ethyl ketone, methyl propyl ketone, methyl isopropyl ketone, methyl butyl ketone, methyl isobutyl ketone, methyl n-hexyl ketone, jetyl ketone, diisopropyl ketone, diisobutyl ketone, cyclopentanone, cyclohexanone, methylcyclohexanone, Examples include acetylacetone, diacetone alcohol, cyclohexene-1-one and the like.
- the block copolymerized polyimide obtained as described above usually has the following characteristics.
- Solder resistance 260 ° C, 60 seconds or more (JIS—C6471 9.3)
- Alkali resistance Less than 1% weight loss after immersion in 5% caustic soda for 30 minutes.
- the ink composition of the present invention contains a photoacid generator together with the above-mentioned block copolymerized polyimide.
- Photoacid generators are compounds that generate acid when irradiated with light, and various products are commercially available.
- Preferred photoacid generators include naphthoquinone diazide photoacid generators and oxonaphthalenediazide photoacid generators.
- a naphthoquinone diazide photoacid generator is a diazide compound having a naphthoquinone skeleton, and is a compound that generates an acid when irradiated with light.
- naphthoquinonediazide photoacid generators include low molecular weight aromatic hydroxy compound esters such as 1,2-naphthoquinone-2-diazido 5-sulfonic acid and 1,2-naphthoquinone-2-diazido 4-sulfonic acid, such as 2 1,4,4-trihydroxybenzophenone, 1,3,5 trihydroxybenzene, 2 and 4-methylphenol, esters of 4,4'-hydroxy-propane and the like are preferably used.
- An oxonaphthalenediide photoacid generator is a diazide compound having an oxonaphthalene skeleton, and is a compound that generates an acid when irradiated with light.
- Oxonaphthalene diazide photoacid generator is a low molecular weight aromatic hydroxy compound ester such as 6-diazo 5,6 dihydro-5 oxonaphthalene 1-sulfonic acid, such as 2,3,4 trihydroxybenzophenone, 1 3,5 -trihydroxybenzene, 2 and 4-methyl-phenol, esters of 4,4, -hydroxy-propane, etc. are preferably used.
- the photoacid generator may be added immediately before using the ink composition.
- the block copolymer polyimide obtained by the above method is added with a photoacid generator as it is without removing the solvent, or further with necessary solvents, additives and the like.
- the photosensitive ink composition for screen printing of the present invention can be used.
- the blending amount of the naphthoquinonediazide photoacid generator is 1 to: LOO parts by weight, preferably 2 to 30 parts by weight with respect to 100 parts by weight of the block copolymerized polyimide. Compounding amount is outside this range This lowers the sensitivity or increases the restrictions on the development process.
- composition of the present invention is added with a sensitizer such as Michler's ketone, 4,4, -jetylaminobenzofenone, 3,3,1 carborubis (jetylaminocoumarin),
- a sensitizer such as Michler's ketone, 4,4, -jetylaminobenzofenone, 3,3,1 carborubis (jetylaminocoumarin)
- the addition amount is set to 0.1 to 20% by weight, more preferably 0.2 to 10% by weight with respect to the block copolymerized polyimide.
- composition of the present invention comprises an alkaline developer, preferably (1) sodium carbonate after light irradiation.
- a positive type image is formed by developing with a developing solution containing 2 wt%).
- a positive acid image is formed by adding a photoacid generator to novolak rosin and irradiating it with light, followed by development with an alkaline aqueous solution.
- the novolak resin has a low molecular weight of 10,000 or less, and it is explained that the solubility in an alkaline aqueous solution is promoted by the interaction of the hydroxyl group of the novolak resin and the carboxylic acid of the photoacid generator. Has been.
- the block copolymerized polyimide contained in the composition of the present invention is a high molecular weight polymer having a polystyrene-equivalent weight average molecular weight of 20,000 or more as described above for use as an insulating film. When the weight average molecular weight is 20,000 or less, a strong insulating film is not formed. High molecular weight polymers do not dissolve easily in alkaline solutions.
- the block copolymerized polyimide is irradiated with light in the presence of a photoacid generator, the hydroxyl group or carboxyl group promotes solubility by interaction with the indenecarboxylic acid generated in the exposed area by light irradiation, and is thus alkaline. It dissolves in a solution and forms a positive image.
- the method of using the photosensitive ink composition of the present invention includes, for example, a silicon wafer, a copper substrate, a metal substrate, a ceramic substrate, an overcoat material, a rigid substrate, FPC, TAB, and COF, a flexible wiring board, It is applied by screen printing on devices around semiconductors such as multilayer circuit boards and multilayer circuit-embedded film substrates, and various electronic components.
- the screen printing method is a well-known printing method in which ink is passed through a screen on which a pattern is formed using a squeegee or the like.
- the desired pattern Selectively irradiate actinic radiation to the shape.
- actinic radiation X-rays, electron beams, ultraviolet rays, visible rays and the like that can be used have a wavelength in the range of 200 to 500 nm.
- a relief pattern is obtained by dissolving and removing the irradiated portion with a developer. After development, most of the unexposed part of the solvent can be dried by heating at 220 ° C. or less to form a coating film made of polyimide resin.
- the film thickness of this coating film is not particularly limited, but it is preferably 4-30 ⁇ m, more preferably 6-20 ⁇ m from the viewpoint of circuit characteristics, etc. 10-15 ⁇ m Particularly preferred is m.
- an alkaline developer or an alkaline aqueous solution can be used as the developer.
- the alkaline developer is a developer obtained by dissolving a basic compound in a solvent of 30% by weight or more.
- the organic solvent include polar solvents such as N-methyl-2-pyrrolidone, N, ⁇ ′-dimethylformamide, ⁇ , N ′ dimethylacetamide, dimethyl sulfoxide, and ⁇ -butyrolataton.
- organic solvents such as alcohols such as methanol and ethanol; aromatic hydrocarbon compounds such as toluene and xylene; ketones such as acetone and methylethyl ketone; ethers such as tetrahydrofuran and dioxazine; A mixture of water can be used.
- the alkaline aqueous solution is a developer obtained by dissolving a basic compound in a solution containing 70% or more of water.
- the additive solvent component other than water for the purpose of improving the development speed include ⁇ -methylpyrrolidone, ⁇ , ⁇ , -dimethylformamide, ⁇ , ⁇ , -dimethylacetamide, dimethyl sulfoxide, y butyrolatathone, etc.
- Aprotic polar solvents such as methanol, ethanol and isopropyl alcohol; ketones such as acetone, methyl ethyl ketone and cyclopentanone; esters such as methyl acetate and methyl lactate; ethers such as tetrahydrofuran and dioxazine Diols such as ethylene glycol and diethylene glycol; cellosolves such as ethylene glycol monomonomethyl ether and propylene glycol monomethyl ether;
- Examples of basic compounds include alkali metals and quaternary ammonium hydroxides, carbonates, bicarbonates, kaates, phosphates, pyrophosphates, Acetate, amine salt and the like are used. Specific examples thereof include sodium hydroxide, lithium hydroxide, potassium hydroxide, ammonium hydroxide, trimethylbenzyl ammonium hydroxide, tetramethyl ammonium. Powers such as umhydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, sodium silicate, sodium phosphate, sodium pyrophosphate, sodium acetate, monoethanolamine, jetanolamine, triethanolamine, choline, etc. It is not something.
- the amount of the basic compound used is usually 0.1 to 20 parts by weight, preferably 0.5 to 10 parts by weight per 100 parts by weight of the solvent (organic solvent or water or a mixture thereof). . If the amount used is too small, the developability tends to decrease and the development time tends to be long. If the amount is too large, the basic compound does not completely dissolve, resulting in a non-uniform solution, or the alkali concentration is too high. Since the solubility with respect to imide is too strong, surface roughness of the unexposed area may occur. Further, it is desirable to use the basic compound in such a ratio that the pH of the developer is usually 10.0 or higher, preferably 11.0-13.5.
- the pH of the developer is less than 10.0, the development speed tends to decrease. If it exceeds 13.5, the solubility in polyimide is too strong, causing swelling of the unexposed areas and surface roughness. It becomes difficult to form a pattern with a good shape with a small difference in solubility between the exposed and unexposed areas.
- the developing method various methods such as spraying, paddle, dipping, ultrasonic dipping, etc. can be employed.
- the development speed is also affected by the temperature of the developer. Therefore, it is desirable to check the various conditions such as the pH of the developer, the solution temperature, or the development method in advance to set the optimum conditions.
- a relief pattern formed by development is generally washed with a rinsing solution to remove the developer.
- the rinsing liquid include methanol, ethanol, isopropanol, water and the like, and these can be used alone or in combination.
- water alone or a mixed liquid of water and alcohols is particularly preferable.
- the amount of alcohol added is usually 5 to 30 parts by weight, preferably 10 to 20 parts by weight per 100 parts by weight of water.
- the photosensitive polyimide ink composition for printing according to the present invention provides a superior titasotropy when the printing is performed.
- Add known fillers and thixotropic agents It is also possible.
- As the filler an insulating inorganic filler, a resin-coated inorganic filler, or a resin filler can be used.
- Insulating inorganic fillers include, for example, silica gel and silica (average particle 0.001-0. 2 m), and examples of inorganic fillers coated with resin include PMMAZ polyethylene and silica Z polyethylene. .
- the resin filler examples include fine particles of epoxy resin having an average particle size of 0.05 m to 50 m, melamine polyphosphate, melem, melamine cyanurate, maleimide resin, polyurethane resin, polyimide, polyamide, and triazine compound. Etc. can be illustrated.
- the filler is preferably fine particles having an average particle size of 0.001 m to 10 m.
- the amount of filler is preferably 3 to 10 parts by weight of filler for 95 to 80 parts by weight of polyimide.
- additives such as known antifoaming agents and leveling agents can be added.
- the leveling agent for example, it is also preferable to contain about 10 ppm to about 2% by weight of a surfactant component, thereby suppressing foaming and flattening the coating film.
- a surfactant component Preferably, it is non-ionic without ionic impurities.
- Suitable surfactants include, for example, 3M “FC-430”, BYK Chemi “BYK-051”, Nippon Yuka Y-5187, A-1310, SS-2801-2805.
- defoaming agent “BYK-A501” from BW Kemi, and “DC-1400” from Dowko Jung Co.
- silicone-based defoaming agent SAG-30, FZ-328, FZ-2191 from Nippon Yuker, FZ-5609, KS-603 manufactured by Shin-Etsu Chemical Co., Ltd.
- This polyimide was poured into methanol and powdered for thermal analysis.
- the glass transition temperature (Tg) was 169.5 ° C, and the decomposition start temperature was 430.1 ° C.
- ODPA62. 04 8 200 mmol —22—161 8 (amino group equivalent 800) 160. OOg (100 mmol), ⁇ -northallate 3.00 g (30 mmol), pyridine 4.75 g (60 mmol) ⁇ -Buchiguchi Lataton 301g, Methyl benzoate 201g, Toluene 60g was stirred at room temperature under nitrogen atmosphere for 30 minutes at 180rpm, then heated to 180 ° C and stirred for 2 hours. The azeotropic component of toluene water was removed.
- MBAA 3, 3′-dicarboxy-4,4′-diaminodiphenylmethane
- APB 29.23 g (100 mmol) 119 g of ⁇ -butyral rataton
- 80 g of methyl benzoate and 60 g of toluene were added, and the mixture was reacted at 180 ° C. and 180 rpm for 5 hours.
- a polyimide solution having a concentration of 30% was obtained.
- the molecular weight, glass transition point, and thermal decomposition start temperature were measured.
- ODPA46. 53 8 150 mimoles —22—161 eight (amino group equivalent 800) 80.
- OOg 50 mmol
- APBS 7.01 g (25 mmol)
- TME G-100 ethylene glycol-bis-trimellitic anhydride ester
- First-stage reaction was carried out in the same manner as in Synthesis Example 1, using 3.OOg (30 mmol), 4.74 g (60 mmol) of pyridine, 147 g of ⁇ -butyrolatamine, and 147 g of methyl benzoate.
- the copolymer polyimide resin component is 15 g.
- 4-Trihydroxybenzophenone and 6-Diazo 5, 6-Dihydro 5-oxo naphthalene 1-Sulphonic acid ester Toyo Gosei Chemical Co., Ltd. product: 4NT-300
- Polyimide 15% by weight based on resin KS-603 (1 to 3% by weight based on polyimide resin) manufactured by Shin-Etsu Chemical Co., Ltd. was added as a defoaming agent.
- the amount of photosensitizer and defoamer is the amount of added calories (parts by weight) relative to 100 parts by weight of polyimide resin solids.
- Printing was performed using a MT-550TVC screen printing machine manufactured by Microtech, using a test solid mask from PI Research Laboratory.
- the printing plate used in the evaluation is a test printing screen (165 mesh 3D stainless steel, emulsion thickness 15 ⁇ m) frame size (200 mm x 250 mm) from PI Research Laboratory. Degree 50 ⁇ : LOOmmZmin, gap (clearance) 1.5mm 2.0mm, squeegee printing pressure was printed under the setting of 0.1 to 0.2 MPa, and the characteristics of the following items were evaluated.
- This evaluation evaluates whether printing can be performed 100 times continuously without changing the film thickness.
- the solid pattern is continuously printed, the 10th shot from the start of printing, and after that, 100 shots are taken every 10 shots, dried to the same conditions as above, and the same shape as above was observed visually and with an optical microscope. did.
- These results are shown in Table 5.
- the continuous circle shot indicates a good film shape
- the X mark indicates a poor film shape.
- printing was stopped when the film shape deteriorated remarkably.
- Example 1 ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ Example 3 ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ Example 5 ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ Example 7 ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ Example 9 ⁇ ⁇ ⁇ ⁇ O ⁇ O ⁇ o
- Example 1 1 ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ Example 13 ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ Example 15 ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇
- the photosensitive polyimide ink for printing of the present invention was excellent in film shape and continuous printability.
- the ink composition for screen printing of the present invention is used for forming a protective layer on a flexible wiring board and a circuit board used for an operation panel of various electronic devices in the electronics field, forming an insulating layer on a laminated board, and a semiconductor device. Used for film formation on electronic parts for protection, insulation and adhesion of silicon wafers, semiconductor chips, semiconductor device peripherals, semiconductor chip disposal substrates, heat sinks, lead pins, semiconductors themselves, etc. Suitable as a photosensitive ink.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Manufacturing & Machinery (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
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KR1020087022095A KR101419314B1 (ko) | 2006-03-03 | 2007-03-02 | 스크린 인쇄용 감광성 잉크 조성물 및 그것을 사용한 포지티브형 릴리프 패턴의 형성 방법 |
EP20070737655 EP2011842B1 (en) | 2006-03-03 | 2007-03-02 | Photosensitive ink composition for screen printing and method of forming positive relief pattern with use thereof |
JP2008502856A JP5006310B2 (ja) | 2006-03-03 | 2007-03-02 | スクリーン印刷用感光性インク組成物及びそれを用いたポジ型レリーフパターンの形成方法 |
US12/224,593 US20090186295A1 (en) | 2006-03-03 | 2007-03-02 | Photosensitive Ink Composition for Screen Printing and Method of Forming Positive Relief Pattern with Use Thereof |
CN2007800075970A CN101395234B (zh) | 2006-03-03 | 2007-03-02 | 丝网印刷用感光性油墨组合物和使用其的正型浮雕图案的形成方法 |
US13/007,373 US8349537B2 (en) | 2006-03-03 | 2011-01-14 | Photosensitive ink composition for screen printing and method of forming positive relief pattern with use thereof |
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JP2006057273 | 2006-03-03 | ||
JP2006-057273 | 2006-03-03 |
Related Child Applications (2)
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US12/224,593 A-371-Of-International US20090186295A1 (en) | 2006-03-03 | 2007-03-02 | Photosensitive Ink Composition for Screen Printing and Method of Forming Positive Relief Pattern with Use Thereof |
US13/007,373 Continuation US8349537B2 (en) | 2006-03-03 | 2011-01-14 | Photosensitive ink composition for screen printing and method of forming positive relief pattern with use thereof |
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WO2007100078A1 true WO2007100078A1 (ja) | 2007-09-07 |
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PCT/JP2007/054007 WO2007100078A1 (ja) | 2006-03-03 | 2007-03-02 | スクリーン印刷用感光性インク組成物及びそれを用いたポジ型レリーフパターンの形成方法 |
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US (2) | US20090186295A1 (ja) |
EP (1) | EP2011842B1 (ja) |
JP (1) | JP5006310B2 (ja) |
KR (1) | KR101419314B1 (ja) |
CN (1) | CN101395234B (ja) |
WO (1) | WO2007100078A1 (ja) |
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WO2010071100A1 (ja) * | 2008-12-15 | 2010-06-24 | 東洋紡績株式会社 | ポジ型感光性ポリイミド樹脂組成物 |
JP2012153890A (ja) * | 2012-02-09 | 2012-08-16 | Jnc Corp | インクジェット用インクおよび当該インクにより得られる硬化膜形成方法 |
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US8349537B2 (en) | 2013-01-08 |
US20110111351A1 (en) | 2011-05-12 |
US20090186295A1 (en) | 2009-07-23 |
JPWO2007100078A1 (ja) | 2009-07-23 |
CN101395234B (zh) | 2012-08-22 |
KR20080100258A (ko) | 2008-11-14 |
EP2011842A1 (en) | 2009-01-07 |
KR101419314B1 (ko) | 2014-07-14 |
JP5006310B2 (ja) | 2012-08-22 |
EP2011842A4 (en) | 2011-07-20 |
CN101395234A (zh) | 2009-03-25 |
EP2011842B1 (en) | 2014-02-26 |
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