WO2017217292A1 - 感光性樹脂組成物、感光性シート、硬化膜、素子、有機el表示装置、半導体電子部品、半導体装置および有機el表示装置の製造方法 - Google Patents
感光性樹脂組成物、感光性シート、硬化膜、素子、有機el表示装置、半導体電子部品、半導体装置および有機el表示装置の製造方法 Download PDFInfo
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- WO2017217292A1 WO2017217292A1 PCT/JP2017/021093 JP2017021093W WO2017217292A1 WO 2017217292 A1 WO2017217292 A1 WO 2017217292A1 JP 2017021093 W JP2017021093 W JP 2017021093W WO 2017217292 A1 WO2017217292 A1 WO 2017217292A1
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- Prior art keywords
- resin composition
- photosensitive resin
- film
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- photosensitive
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- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical group 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229910001936 tantalum oxide Inorganic materials 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 1
- 238000000411 transmission spectrum Methods 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 235000013799 ultramarine blue Nutrition 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
- YKSGNOMLAIJTLT-UHFFFAOYSA-N violanthrone Chemical class C12=C3C4=CC=C2C2=CC=CC=C2C(=O)C1=CC=C3C1=CC=C2C(=O)C3=CC=CC=C3C3=CC=C4C1=C32 YKSGNOMLAIJTLT-UHFFFAOYSA-N 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- 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
- C08G73/1046—Polyimides containing oxygen in the form of ether bonds in the main chain
-
- 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
-
- 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
-
- 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
- G03F7/022—Quinonediazides
- G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
-
- 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
- G03F7/16—Coating processes; Apparatus therefor
- G03F7/168—Finishing the coated layer, e.g. drying, baking, soaking
-
- 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
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/22—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of auxiliary dielectric or reflective layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/10—OLED displays
- H10K59/12—Active-matrix OLED [AMOLED] displays
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/40—Thermal treatment, e.g. annealing in the presence of a solvent vapour
Definitions
- the present invention relates to a photosensitive resin composition. Specifically, a surface protective film and an interlayer insulating film of a semiconductor element, an insulating film of an organic electroluminescence (hereinafter referred to as EL) element, a driving thin film transistor (Thin Film Transistor: hereinafter referred to as TFT) for a display device using the organic EL element.
- EL organic electroluminescence
- TFT driving thin film transistor
- the present invention relates to a photosensitive resin composition suitable for applications such as a flattening film on a substrate, a wiring protective insulating film on a circuit board, an on-chip microlens for a solid-state imaging device, and a flattening film for various displays and solid-state imaging devices.
- heat-resistant resins such as polyimide and polybenzoxazole have excellent heat resistance and electrical insulation
- photosensitive resin compositions containing these heat-resistant resins are used as surface protective films for semiconductor elements such as LSI, It is used for an interlayer insulating film, an insulating layer of an organic electric field element and an organic EL display element, a planarizing film of a TFT substrate for a display device, and the like.
- a polyimide resin using a tetracarboxylic acid anhydride having a fluorine atom such as a hexafluoropropyl group forms a cured film having a brittle cured film and excellent bending resistance. There were cases where it was difficult to do.
- a polyimide resin using a tetracarboxylic acid anhydride having an ester group structure as described in Patent Document 5 is excellent in bending resistance, but sometimes has insufficient sensitivity.
- an object of the present invention is to provide a highly sensitive photosensitive resin composition having a high residual film ratio after development and high bending resistance in a cured film.
- the present invention comprises (a) an alkali-soluble resin and (b) a photosensitive compound, wherein the (a) alkali-soluble resin has 95 to 100 mol% of the structural unit represented by the general formula (1), (A) A photosensitive resin composition having an organic group derived from a monomeramine or an acid anhydride at at least one end of a polymer molecular chain in the alkali-soluble resin.
- R 1 is a divalent organic group.
- R 2 and R 3 each independently represent hydrogen or an organic group having 1 to 20 carbon atoms.
- X 1 and X 2 are each Independently represents a linear or branched alkylene group having 2 to 20 carbon atoms, 1,3-phenylene group or 1,4-phenylene group, wherein R 1 , X 1 and X 2 are each in a plurality of repeating units; M and n are each an integer from 0 to 100,000, and m + n ⁇ 3.
- the resin of the present invention is an alkali-soluble resin selected from an alkali-soluble polyimide having a structural unit represented by the above general formula (1), a polyimide precursor, or a copolymer thereof.
- a photosensitive resin composition having an alkali-soluble resin is preferably used in the production of an organic EL display device.
- the polyimide precursor for example, it is obtained by reacting tetracarboxylic acid, corresponding tetracarboxylic dianhydride or tetracarboxylic diester dichloride and the like with diamine, corresponding diisocyanate compound or trimethylsilylated diamine, and the like. And having a tetracarboxylic acid and / or its derivative residue and a diamine and / or its derivative residue.
- the polyimide precursor include polyamic acid, polyamic acid ester, polyamic acid amide, and polyisoimide.
- polyimide examples include those obtained by dehydrating and ring-closing the above polyamic acid, polyamic acid ester, polyamic acid amide, or polyisoimide by heating or a reaction using an acid or a base. And / or a derivative residue thereof and a diamine and / or a derivative residue thereof.
- an ester group-containing tetracarboxylic dianhydride is used.
- a cured film having high solvent solubility and flexibility can be obtained by making free rotation of the polymer main chain easier than a rigid polyimide having only an imide structure.
- the ester group-containing tetracarboxylic dianhydride is not particularly limited, and commercially available products and those obtained by a conventionally known production method can also be used.
- X 1 and X 2 in the general formula (1) are a linear or branched alkylene group having 1 to 20 carbon atoms, a 1,3-phenylene group, or a 1,4-phenylene group, preferably a carbon number 2 to 20 linear or branched alkylene groups. Since the alkylene group can take various conformations, the flexibility of the cured film can be further increased by having the alkylene group in the molecular chain of the resin. From the viewpoint of improving the heat resistance of the resin, it is preferably a linear or branched alkylene group having 2 to 6 carbon atoms, more preferably a linear or branched alkylene group having 2 to 4 carbon atoms. In particular, ethylene group.
- X 1 and X 2 in the general formula (1) are an ethylene group, a propylene group, or a butylene group. As described above, more preferably an ethylene group.
- X 1 and X 2 are ethylene groups, a cured film having a particularly excellent balance between heat resistance and flexibility can be provided.
- ester group-containing tetracarboxylic dianhydrides include 1,2-ethylenebis (anhydrotrimellitate), 1,3-propylenebis (anhydrotrimellitate), and 1,4-tetramethylene.
- 1,2-ethylenebis (anhydrotrimellitate) is preferably used because it is particularly excellent in the balance between heat resistance and flexibility.
- the (a) alkali-soluble resin used in the present invention has 95 to 100 mol% of the structural unit represented by the general formula (1), so that the solubility in an organic solvent is improved and the flexibility of the resin composition is increased. Can be improved.
- the structural unit is a repeating unit and represents a structure represented by the repeating numbers m and n, respectively, and the structure represented by the repeating numbers m and n may be random or block.
- the alkali-soluble resin having 95 to 100 mol% of the structural unit represented by the general formula (1) is an ester group-containing tetracarboxylic acid diester based on 100 mol% of the diamine component in accordance with a known method for producing a polyimide precursor described later. It can be obtained by using 95 to 100 mol% of anhydride.
- A By having 95 mol% or more of the structural units represented by the general formula (1) in the alkali-soluble resin, it is possible to provide a resin having excellent flexibility and high bending resistance.
- X 1 and X 2 are each a linear or branched alkylene group having 2 to 20 carbon atoms, a 1,3-phenylene group, or a 1,4-phenylene group. Since it exhibits hydrophobicity, a resin having a high residual film ratio after development can be provided. In particular, when (a) the alkali-soluble resin contains 95 mol% or more of the structural unit represented by the general formula (1), a resin having a high residual film ratio after development can be provided.
- alkali-soluble resin used for this invention contains the structure derived from other acid dianhydrides in addition to ester group containing tetracarboxylic dianhydride in the range which does not reduce the above-mentioned characteristic. Also good.
- acid dianhydrides include pyromellitic dianhydride, 3,3 ′, 4,4′-biphenyltetracarboxylic dianhydride, and 2,3,3 ′, 4′-biphenyl.
- Tetracarboxylic dianhydride 2,2 ′, 3,3′-biphenyltetracarboxylic dianhydride, 3,3 ′, 4,4′-benzophenonetetracarboxylic dianhydride, 2,2 ′, 3, 3′-benzophenone tetracarboxylic dianhydride, 2,2-bis (3,4-dicarboxyphenyl) propane dianhydride, 2,2-bis (2,3-dicarboxyphenyl) propane dianhydride, 1 , 1-bis (3,4-dicarboxyphenyl) ethane dianhydride, 1,1-bis (2,3-dicarboxyphenyl) ethane dianhydride, bis (3,4-dicarboxyphenyl) methane dianhydride Bis (2,3-dicar Xylphenyl) methane dianhydride, bis (3,4-dicarboxyphenyl) ether dianhydride, 1,2,5,6-naphthalenete
- R 10 represents an oxygen atom, C (CF 3 ) 2 , or C (CH 3 ) 2.
- R 11 and R 12 represent a hydrogen atom or a hydroxyl group.
- the (a) alkali-soluble resin of the present invention preferably has a fluorine atom.
- R 1 is a structure derived from diamine.
- R 1 is preferably an organic group having a fluorine atom. By having fluorine atoms, water repellency is imparted to the surface of the film during alkali development, and soaking in from the surface can be suppressed. A photosensitive resin film having a high rate is obtained.
- an organic group having a fluorine atom is 100 mole% the total amount of R 1, preferably at least 30 mol%.
- Such a structure is introduced by using 30 mol% or more of a fluorine atom-containing monomer among the monomer components for introducing R 1 .
- the monomer containing fluorine atoms is preferably 90 mol% or less.
- diamine having a fluorine atom examples include bis (3-amino-4-hydroxyphenyl) hexafluoropropane, 2,2′-bis (trifluoromethyl) -4,4′-diaminobiphenyl, 2, Aromatic diamines such as 2′-bis (trifluoromethyl) -5,5′-dihydroxybenzidine, and a part of hydrogen atoms of these aromatic rings are substituted with alkyl groups having 1 to 10 carbon atoms or fluoroalkyl groups, And compounds substituted with a halogen atom.
- the resin having the structure represented by the general formula (1) is preferably a resin including a structure derived from these compounds.
- (a) alkali-soluble resin of this invention has a phenolic hydroxyl group.
- R 1 is preferably an organic group having a phenolic hydroxyl group.
- the phenolic hydroxyl group can be appropriately dissolved in an alkali developer, and can interact with the photosensitizer to suppress the solubility of the unexposed area, thereby improving the remaining film ratio and increasing the sensitivity.
- the phenolic hydroxyl group also contributes to the reaction with the cross-linking agent, and thus is preferable in that high mechanical properties and chemical resistance can be obtained.
- the organic group having a phenolic hydroxyl group is preferably 30 mol% or more when the total amount of R 1 is 100 mol%.
- Such a structure is introduced by using 30 mol% or more of a monomer containing a phenolic hydroxyl group among the monomer components for introducing R 1 . More preferably, it is 50 mol% or more.
- the monomer containing a phenolic hydroxyl group is preferably 90 mol% or less.
- diamine having a phenolic hydroxyl group examples include bis (3-amino-4-hydroxyphenyl) hexafluoropropane, bis (3-amino-4-hydroxyphenyl) sulfone, and bis (3-amino-4-hydroxy).
- Compounds substituted with alkyl groups, fluoroalkyl groups, halogen atoms, etc. Door can be.
- the resin having the structure represented by the general formula (1) is preferably a resin including a structure derived from these compounds.
- R 1 in the general formula (1) of the present invention may have a structure derived from other diamines in addition to the diamines described above.
- diamines include “Jephamine” (registered trademark) KH-511, "Jephamine” ED-600, “Jephamine” ED-900, and “Jephamine” ED as aliphatic diamines containing polyethylene oxide groups. -2003, “Jeffamine” EDR-148, “Jeffamine” EDR-176, polyoxypropylene diamine D-200, D-400, D-2000, D-4000 (above trade names, manufactured by HUNTSMAN Co., Ltd.) And so on.
- the use of aliphatic alkyl diamines is preferable because flexibility is imparted and the elongation at break is improved, and the elastic modulus is lowered to suppress the warpage of the wafer.
- the residue derived from the aliphatic alkyl diamine in all diamine residues is preferably 10 mol% or more, and from the viewpoint of improving heat resistance, it is preferably 50 mol% or less.
- an aliphatic group having a siloxane structure may be included within a range in which the heat resistance is not lowered, and adhesion to the substrate can be improved.
- bis (3-aminopropyl) tetramethyldisiloxane, bis (p-aminophenyl) octamethylpentasiloxane and the like are copolymerized in an amount of 1 to 15 mol%.
- Still other diamines include bis (3-amino-4-hydroxyphenyl) hexafluoropropane, bis (3-amino-4-hydroxyphenyl) sulfone, bis (3-amino-4-hydroxyphenyl) propane, bis (3 -Amino-4-hydroxyphenyl) methylene, bis (3-amino-4-hydroxyphenyl) ether, bis (3-amino-4-hydroxy) biphenyl, bis (3-amino-4-hydroxyphenyl) fluorene, 2, Hydroxyl group-containing diamines such as 2'-bis (trifluoromethyl) -5,5'-dihydroxybenzidine, sulfonic acid-containing diamines such as 3-sulfonic acid-4,4'-diaminodiphenyl ether, and thiols such as dimercaptophenylenediamine Group-containing diamine, 3,4'-diamino Phenyl ether, 4,4'-diaminodipheny
- Examples thereof include an alkyl group, a fluoroalkyl group, a compound substituted with a halogen atom, and alicyclic diamines such as cyclohexyldiamine and methylenebiscyclohexylamine. These diamines can be used as they are or as the corresponding diisocyanate compounds and trimethylsilylated diamines. Moreover, you may use combining these 2 or more types of diamine components. From the viewpoint of improving heat resistance, it is preferable to use an aromatic diamine in an amount of 50 mol% or more of the total diamine.
- R 13 represents an oxygen atom, C (CF 3 ) 2 or C (CH 3 ) 2.
- R 14 and R 15 each independently represents a hydrogen atom or a hydroxyl group.
- the resin having a structure represented by the general formula (1) of the present invention can contain a sulfonic acid group, a thiol group, and the like. By using a resin having moderately sulfonic acid groups and thiol groups, a photosensitive resin composition having moderate alkali solubility is obtained.
- Alkali-soluble resin used in the photosensitive resin composition of the present invention has an organic group derived from a monoamine or acid anhydride at at least one terminal of a polymer molecular chain.
- monoamine or acid anhydride is a terminal blocking agent.
- a terminal sealing agent By using a terminal sealing agent, it becomes easy to adjust the photosensitive resin composition to an appropriate viscosity. Further, it is possible to suppress hydrolysis of the resin by the acid terminal, and to suppress the deterioration of the quinonediazide compound, which is a photosensitizer by the amine terminal, when the positive photosensitive resin composition is obtained.
- the terminal blocking agent preferably has a hydroxyl group, a carboxyl group or a sulfonic acid group as a substituent, and more preferably a hydroxyl group from the viewpoint of improving heat resistance.
- the terminal blocking agent has a hydroxyl group, a carboxyl group, or a sulfonic acid group as a substituent, the solubility of the resulting resin in an alkaline aqueous solution can be improved, and a highly sensitive resin can be provided.
- the resin has a hydroxyl group, a carboxyl group or a sulfonic acid group at the terminal, when it is made a positive photosensitive resin composition, the unexposed portion is hardly soluble by interacting with the quinonediazide compound through a hydrogen bond.
- a resin having a high residual film ratio after development can be provided.
- the monoamine used for terminal blocker is not particularly limited, a compound represented by the following general formula (2) is preferred for the following reasons.
- a compound represented by the following general formula (2) is preferred for the following reasons.
- a hydroxyl group a carboxyl group or a sulfonic acid group
- moderate solubility in an alkali developer can be obtained, and when a positive photosensitive resin composition is obtained, a quinonediazide compound By interacting with each other through a hydrogen bond, the unexposed portion becomes slightly soluble, and a resin having a high residual film ratio after development can be provided.
- the phenolic hydroxyl group also contributes to the reaction with the cross-linking agent, and thus is preferable in that high mechanical properties and chemical resistance can be obtained.
- R 4 represents a saturated hydrocarbon group having 1 to 6 carbon atoms, and r represents 0 or 1.
- a and B may be the same or different, and may be a hydroxyl group, a carboxyl group or Represents a sulfonic acid group, and s and t each represents 0 or 1, and s + t ⁇ 1 from the viewpoint of improving the solubility of the resulting resin in an aqueous alkali solution.
- Preferred examples of the monoamine represented by the general formula (2) include 2-aminophenol, 3-aminophenol (MAP), 2-amino-m-cresol, 2-amino-p-cresol, 3-amino-o -Cresol, 4-amino-o-cresol, 4-amino-m-cresol, 5-amino-o-cresol, 6-amino-m-cresol, 4-amino-2,3-xylenol, 4-amino-3 , 5-xylenol, 6-amino-2,4-xylenol, 2-amino-4-ethylphenol, 3-amino-4-ethylphenol, 2-amino-4-tert-butylphenol, 2-amino-4-phenyl Phenol, 4-amino-2,6-diphenylphenol, 4-aminosalicylic acid, 5-aminosalicylic acid, 6-aminosalicylic acid, 2 Aminobenzoic acid, 3-aminobenzoic acid, 4-
- the introduction ratio of the monoamine used as the end-capping agent is preferably 10 to 100 mol%, more preferably 40 to 80 mol% with respect to 100 mol% of the structural unit represented by the general formula (1).
- the solubility of the resulting resin in an organic solvent is improved, and the viscosity when a photosensitive resin composition is made using the obtained resin is appropriately adjusted. can do.
- it is preferably 100 mol% or less, more preferably 80 mol% or less, and even more preferably 70 mol% or less.
- the acid anhydride used for terminal blocker is not particularly limited, it has an acid anhydride or a crosslinkable group having a cyclic structure from the viewpoint of heat resistance of the cured film of the photosensitive resin composition using the obtained resin.
- Acid anhydrides are preferred. Examples include phthalic anhydride, maleic anhydride (MA), nadic anhydride, cyclohexanedicarboxylic anhydride, 3-hydroxyphthalic anhydride and the like.
- the introduction ratio of the acid anhydride used as the terminal blocking agent is preferably 10 to 100 mol%, more preferably 50 to 100 mol% with respect to 100 mol% of the structural unit represented by the general formula (1).
- the solubility of the resulting resin in an organic solvent is improved, and the viscosity when a photosensitive resin composition is made using the obtained resin is appropriately adjusted. can do.
- 100 mol% or less is preferable and 90 mol% or less is more preferable from a viewpoint of the solubility with respect to the aqueous alkali solution of the resin obtained, and the mechanical strength of a cured film.
- the end-capping agent introduced into the resin can be easily detected by the following method.
- a resin having a terminal blocking agent introduced therein is dissolved in an acidic solution and decomposed into an amine component and an acid component, which are constituent units of the resin, and this is measured by gas chromatography (GC) or NMR measurement.
- GC gas chromatography
- NMR nuclear magnetic resonance
- m and n represent the number of repeating structural units of the resin and represent a range of 0 to 100,000, where m + n ⁇ 3.
- m + n is preferably 10 or more.
- m + n is 200,000 or less, preferably 1,000 or less, more preferably 100 or less, from the viewpoint of solubility of the resulting photosensitive resin composition containing a resin in an alkaline developer.
- m / n> 1 from the viewpoint of reducing the shrinkage rate during curing.
- m / n> 2 more preferably m / n> 4.
- the weight average molecular weight of the resin having the structural unit represented by the general formula (1) is preferably 3,000 to 80,000 in terms of polystyrene by gel permeation chromatography, and more preferably 8,000 to 50,000. It is.
- the (a) alkali-soluble resin of the present invention can be produced according to a known method for producing a polyimide precursor.
- a method for producing a polyimide precursor for example, (I) a method of reacting an ester group-containing tetracarboxylic dianhydride with a diamine compound having an R 1 group and a monoamine which is a terminal blocking agent under low temperature conditions, (II) an ester group-containing tetracarboxylic acid bis A method of reacting in the presence of a diamine compound having an R 1 group, a monoamine which is a terminal blocking agent, and a condensing agent after obtaining a diester by an anhydride and an alcohol, (III) an ester group-containing tetracarboxylic dianhydride Examples include a method in which a diester is obtained with alcohol and then the remaining two carboxyl groups are acid chlorideed and reacted with a diamine compound having an R 1 group and a monoamine which is a
- the resin polymerized by the above method is preferably put into a large amount of water or a methanol / water mixture, precipitated, filtered, dried and isolated.
- This precipitation operation unreacted monomers and oligomer components such as dimers and trimers are removed, and film properties after thermosetting are improved.
- after imidating the polyimide precursor and ring-closing polyimide after obtaining said polyimide precursor, it can synthesize
- a diamine compound having an R 1 group is dissolved in a polymerization solvent.
- an ester group-containing tetracarboxylic dianhydride which is substantially equimolar with the diamine compound, is gradually added.
- the mixture is stirred at ⁇ 20 to 100 ° C., preferably 10 to 50 ° C. for 0.5 to 100 hours, more preferably 2 to 24 hours.
- the end-capping agent may be added after the addition of tetracarboxylic dianhydride and stirred at a predetermined temperature for a predetermined time, and then the end-capping agent may be gradually added, or may be reacted at once. .
- the polymerization solvent is not particularly limited as long as it can dissolve the raw material monomers tetracarboxylic dianhydride and diamine.
- the polymerization solvent is preferably used in an amount of 100 to 1900 parts by weight, more preferably 150 to 950 parts by
- the photosensitive resin composition of the present invention may contain (a) an alkali-soluble resin other than the alkali-soluble resin.
- examples thereof include resins introduced with a crosslinking group such as a group or an epoxy group, and copolymers thereof.
- Such a resin is soluble in an aqueous alkali solution such as tetramethylammonium hydroxide, choline, triethylamine, dimethylaminopyridine, monoethanolamine, diethylaminoethanol, sodium hydroxide, potassium hydroxide, sodium carbonate.
- an aqueous alkali solution such as tetramethylammonium hydroxide, choline, triethylamine, dimethylaminopyridine, monoethanolamine, diethylaminoethanol, sodium hydroxide, potassium hydroxide, sodium carbonate.
- the (a) alkali-soluble resin of the present invention is preferably 30% by mass or more.
- the photosensitive resin composition of the present invention contains (b) a photosensitive compound.
- the photosensitive compound include (b1) a photoacid generator and (b2) a photopolymerization initiator.
- a photoacid generator is a compound that generates acid when irradiated with light and gives the property of increasing the solubility of the light-irradiated part in an alkaline aqueous solution
- (b2) a photopolymerization initiator is an exposure. Refers to a compound that generates a radical through bond cleavage and / or reaction.
- (B1) By containing a photoacid generator, acid is generated in the light irradiation part, the solubility of the light irradiation part in the alkaline aqueous solution is increased, and a positive relief pattern in which the light irradiation part dissolves can be obtained. it can.
- (b1) by containing a photoacid generator and an epoxy compound or a thermal cross-linking agent described later, the acid generated in the light irradiation part promotes the cross-linking reaction of the epoxy compound and the heat cross-linking agent, and the light irradiation part is insolubilized. A negative relief pattern can be obtained.
- (b2) by containing a photopolymerization initiator and a radical polymerizable compound described later, radical polymerization proceeds, and the exposed portion of the film of the resin composition is insolubilized in an alkali developer, so that the negative type is obtained.
- the pattern can be formed.
- Examples of the photoacid generator include quinonediazide compounds, sulfonium salts, phosphonium salts, diazonium salts, and iodonium salts.
- the quinonediazide compound includes a polyhydroxy compound in which a sulfonic acid of quinonediazide is bonded with an ester, a polyamino compound in which a sulfonic acid of quinonediazide is bonded to a sulfonamide, and a sulfonic acid of quinonediazide in an ester bond and / or sulfone.
- Examples include amide-bonded ones. It is preferable that 50 mol% or more of the total functional groups of these polyhydroxy compounds and polyamino compounds are substituted with quinonediazide.
- quinonediazide is preferably a 5-naphthoquinonediazidesulfonyl group or a 4-naphthoquinonediazidesulfonyl group.
- the 4-naphthoquinonediazide sulfonyl ester compound has absorption in the i-line region of a mercury lamp and is suitable for i-line exposure.
- the 5-naphthoquinonediazide sulfonyl ester compound has an absorption extending to the g-line region of a mercury lamp and is suitable for g-line exposure.
- it may contain a naphthoquinone diazide sulfonyl ester compound having a 4-naphthoquinone diazide sulfonyl group and a 5-naphthoquinone diazide sulfonyl group in the same molecule, or a 4-naphthoquinone diazide sulfonyl ester compound and a 5-naphthoquinone diazide sulfonyl ester compound. You may contain.
- the naphthoquinonediazide compound can be synthesized by an esterification reaction between a compound having a phenolic hydroxyl group and a quinonediazidesulfonic acid compound, and can be synthesized by a known method. By using these naphthoquinonediazide compounds, resolution, sensitivity, and remaining film ratio are further improved.
- sulfonium salts Of the photoacid generators, sulfonium salts, phosphonium salts, and diazonium salts are preferable because they moderately stabilize the acid component generated by exposure. Of these, sulfonium salts are preferred. Furthermore, it can also contain a sensitizer etc. as needed.
- the content of the (b1) photoacid generator is preferably 0.01 to 50 parts by mass with respect to (a) 100 parts by mass of the alkali-soluble resin from the viewpoint of increasing sensitivity.
- the quinonediazide compound is preferably 3 to 40 parts by mass.
- the total amount of sulfonium salt, phosphonium salt and diazonium salt is preferably 0.5 to 20 parts by mass.
- photopolymerization initiator examples include benzyl ketal photopolymerization initiators, ⁇ -hydroxyketone photopolymerization initiators, ⁇ -aminoketone photopolymerization initiators, acylphosphine oxide photopolymerization initiators, and oxime esters.
- Photopolymerization initiator acridine photopolymerization initiator, titanocene photopolymerization initiator, benzophenone photopolymerization initiator, acetophenone photopolymerization initiator, aromatic ketoester photopolymerization initiator or benzoate photopolymerization initiator
- ⁇ -hydroxyketone photopolymerization initiator, ⁇ -aminoketone photopolymerization initiator, acylphosphine oxide photopolymerization initiator, oxime ester photopolymerization initiator, acridine -Based photopolymerization initiator or benzophenone-based photopolymerization initiator is more preferable, ⁇ -aminoketone-based photopolymerization initiator More preferred are an agent, an acylphosphine oxide photopolymerization initiator, and an oxime ester photopolymerization initiator.
- Examples of the benzyl ketal photopolymerization initiator include 2,2-dimethoxy-1,2-diphenylethane-1-one.
- Examples of ⁇ -hydroxyketone photopolymerization initiators include 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one and 2-hydroxy-2-methyl-1-phenylpropane-1. -One, 1-hydroxycyclohexyl phenyl ketone, 1- [4- (2-hydroxyethoxy) phenyl] -2-hydroxy-2-methylpropan-1-one or 2-hydroxy-1- [4- [4- ( 2-hydroxy-2-methylpropionyl) benzyl] phenyl] -2-methylpropan-1-one.
- Examples of the ⁇ -aminoketone photopolymerization initiator include 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1- (4 -Morpholinophenyl) -butan-1-one, 2-dimethylamino-2- (4-methylbenzyl) -1- (4-morpholinophenyl) -butan-1-one or 3,6-bis (2-methyl- 2-morpholinopropionyl) -9-octyl-9H-carbazole.
- acylphosphine oxide photopolymerization initiator examples include 2,4,6-trimethylbenzoyl-diphenylphosphine oxide, bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide, or bis (2,6-dimethoxybenzoyl). )-(2,4,4-trimethylpentyl) phosphine oxide.
- oxime ester photopolymerization initiator examples include 1-phenylpropane-1,2-dione-2- (O-ethoxycarbonyl) oxime, 1-phenylbutane-1,2-dione-2- (O-methoxy).
- Examples of the acridine photopolymerization initiator include 1,7-bis (acridin-9-yl) -n-heptane.
- titanocene photopolymerization initiators include bis ( ⁇ 5-2,4-cyclopentadien-1-yl) -bis [2,6-difluoro) -3- (1H-pyrrol-1-yl) phenyl] titanium. (IV) or bis ( ⁇ 5-3-methyl-2,4-cyclopentadien-1-yl) -bis (2,6-difluorophenyl) titanium (IV).
- benzophenone photopolymerization initiator examples include benzophenone, 4,4′-bis (dimethylamino) benzophenone, 4,4′-bis (diethylamino) benzophenone, 4-phenylbenzophenone, 4,4-dichlorobenzophenone, 4- Examples include hydroxybenzophenone, alkylated benzophenone, 3,3 ′, 4,4′-tetrakis (t-butylperoxycarbonyl) benzophenone, 4-methylbenzophenone, dibenzyl ketone or fluorenone.
- acetophenone photopolymerization initiator examples include 2,2-diethoxyacetophenone, 2,3-diethoxyacetophenone, 4-t-butyldichloroacetophenone, benzalacetophenone, and 4-azidobenzalacetophenone.
- aromatic ketoester photopolymerization initiator examples include methyl 2-phenyl-2-oxyacetate.
- benzoate photopolymerization initiator examples include ethyl 4-dimethylaminobenzoate, 4-dimethylaminobenzoic acid (2-ethyl) hexyl, ethyl 4-diethylaminobenzoate, or methyl 2-benzoylbenzoate.
- the content of the (b2) photopolymerization initiator is 0.1 parts by mass or more when the total of (a) the alkali-soluble resin and the later-described (d) radical polymerizable compound is 100 parts by mass.
- Is preferably 0.5 parts by mass or more, more preferably 0.7 parts by mass or more, and particularly preferably 1 part by mass or more.
- the sensitivity at the time of exposure can be improved as content is in the said range.
- the content is preferably 25 parts by mass or less, more preferably 20 parts by mass or less, further preferably 17 parts by mass or less, and particularly preferably 15 parts by mass or less.
- the photosensitive resin composition of the present invention contains (c) a solvent.
- a solvent ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol ethyl methyl ether and other ethers, ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, Esters such as ethyl acetate, butyl acetate, methyl lactate, ethyl lactate, butyl lactate, alcohols such as ethanol, isopropanol, butanol, pentanol, 3-methyl-2-butanol, 3-methyl-3-methoxybutanol, methyl ethyl ketone , Methyl isobutyl ketone, methyl amyl ketone, diisobutyl ketone,
- the content of the solvent (c) is preferably 50 parts by mass or more, more preferably 100 parts by mass or more, and preferably 2000 parts by mass or less, more preferably 100 parts by mass of the (a) alkali-soluble resin. Is 1500 parts by mass or less.
- the photosensitive resin composition of the present invention may further contain (d) a radical polymerizable compound.
- the radical polymerizable compound refers to a compound having a plurality of ethylenically unsaturated double bond groups in the molecule.
- (b) radical polymerization of the radical polymerizable compound proceeds by the radical generated from the photopolymerization initiator (b2), and the exposed portion of the film of the resin composition is insolubilized in the alkali developer. Thus, a negative pattern can be formed.
- a compound having a (meth) acrylic group that facilitates radical polymerization is preferable. From the viewpoint of improving the sensitivity during exposure and improving the hardness of the cured film, a compound having two or more (meth) acryl groups in the molecule is more preferable.
- the double bond equivalent of the radical polymerizable compound is preferably from 80 to 400 g / mol from the viewpoint of improving sensitivity during exposure and improving the hardness of the cured film.
- Examples of the radically polymerizable compound (d) include diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, trimethylolpropane di ( (Meth) acrylate, trimethylolpropane tri (meth) acrylate, ethoxylated trimethylolpropane di (meth) acrylate, ethoxylated trimethylolpropane tri (meth) acrylate, ditrimethylolpropane tri (meth) acrylate, ditrimethylolpropane tetra (meta) ) Acrylate, 1,3-butanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, 1,4-butanediol di (meth) acrylate 1,6-hexanediol di (
- trimethylolpropane tri (meth) acrylate ditrimethylolpropane tri (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, pentaerythritol tri (meth) acrylate, Pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, tripentaerythritol hepta (meth) acrylate, tripentaerythritol octa (meth) acrylate, 2,2-bis [ 4- (3- (meth) acryloxy-2-hydroxypropoxy) phenyl] propane, 1,3,5-tris ((meth) acryloxyethyl) isocyanuric acid, 1,3-bis ( ( (meth) acryloxyethyl) isocyanuric acid, 1,
- these acid-modified products Or an ethylene oxide modified product is more preferable.
- a compound obtained by subjecting a compound having two or more glycidoxy groups in the molecule and an unsaturated carboxylic acid having an ethylenically unsaturated double bond group to a ring-opening addition reaction Also preferred are compounds obtained by reacting polybasic acid carboxylic acids or polybasic carboxylic acid anhydrides.
- the content of the (d) radical polymerizable compound is preferably 15 parts by mass or more and 20 parts by mass when the total of (a) the alkali-soluble resin and (d) the radical polymerizable compound is 100 parts by mass. Part or more is more preferable, 25 parts by weight or more is more preferable, and 30 parts by weight or more is particularly preferable.
- the content is preferably 65 parts by mass or less, more preferably 60 parts by mass or less, further preferably 55 parts by mass or less, and particularly preferably 50 parts by mass or less.
- the heat resistance of the cured film can be improved, and a low taper pattern shape can be obtained. By setting the pattern shape to a low taper, driving stability of the completed organic EL panel can be enhanced.
- the photosensitive resin composition of the present invention can further contain (e) a thermal crosslinking agent.
- the thermal crosslinking agent refers to a compound having in the molecule at least two thermally reactive functional groups such as an alkoxymethyl group, a methylol group, an epoxy group, and an oxetanyl group.
- the thermal cross-linking agent can cross-link (a) the alkali-soluble resin or other additive components, and can increase the heat resistance, chemical resistance and hardness of the heat-cured film.
- Preferred examples of the compound having at least two alkoxymethyl groups or methylol groups include, for example, 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, DML-BisOC-P, DMOM- PC, DMOM-PTBP, DMOM-MBPC, TriML-P, TriML-35XL, TML-HQ, TML-BP, TML-pp-BPF, TML-BPE, TML-BPA, TML-BPAF, TML-BPAP, TMOM- BP, TMOM- PE, TMOM-BPA, TMOM-BPAF, TMOM-BPAP, H
- Epicoat (registered trademark) 807, “Epicoat” 828, “Epicoat” 1002, “Epicoat” 1750, “Epicoat” have two epoxy groups in one molecule.
- VG3101L (trade name, manufactured by Printec Co., Ltd.), “Tepic” (registered trademark) S, “Tepic” G, “Tepic” P (above trade names, Nissan Chemical Co., Ltd.) have three or more epoxy groups.
- the content of the thermal crosslinking agent is preferably 5 parts by mass or more with respect to 100 parts by mass of the (a) alkali-soluble resin, because the crosslinking density increases and chemical resistance is improved. Further, when it is 10 parts by mass or more, higher mechanical properties can be obtained. On the other hand, from the viewpoint of storage stability and mechanical strength of the composition, it is preferably 50 parts by mass or less, more preferably 40 parts by mass or less, and further preferably 30 parts by mass or less.
- the photosensitive resin composition of the present invention may further contain (f) a colorant.
- the colorant is a compound that absorbs light of a specific wavelength, and particularly, a compound that colors by absorbing light having a wavelength of visible light (380 to 780 nm).
- a film obtained from the resin composition can be colored, and light transmitted through the resin composition film or light reflected from the resin composition film can be obtained in a desired manner. Coloring can be imparted to the color. In addition, light having a wavelength absorbed by the colorant (f) can be imparted from light transmitted through the resin composition film or reflected from the resin composition film.
- Examples of the colorant include compounds that absorb light having a wavelength of visible light and are colored white, red, orange, yellow, green, blue, or purple. By combining two or more colors, the toning property of toning the light transmitted through the resin composition film of the resin composition or the light reflected from the resin composition film to the desired color coordinates Can be improved.
- the (f) colorant is preferably a (f1) pigment and / or (f2) dye described later.
- the (f) colorant is preferably a colorant other than (f3) black agent and / or (f4) black.
- the black agent means a compound that is colored black by absorbing light having a wavelength of visible light, and may be a pigment or a dye.
- (F3) As the black agent, from the viewpoint of light shielding properties, a compound that absorbs light of all wavelengths of visible light and is colored black is preferable. Also preferred is a mixture of two or more compounds selected from white, red, orange, yellow, green, blue or purple. By combining these two or more colors, it is possible to artificially color black and improve the light-shielding property.
- the (f3) black agent preferably contains one or more selected from a black pigment, a black dye and a dye mixture of two or more colors, from the viewpoint of light shielding properties. It is more preferable to contain a black pigment.
- a colorant other than black refers to a compound that is colored by absorbing light having a wavelength of visible light. That is, the above-mentioned colorants that are colored white, red, orange, yellow, green, blue, or purple, excluding black.
- the film of the resin composition can be provided with light-shielding properties, coloring properties, and toning properties.
- the colorant other than (f4) black preferably contains a pigment other than black and / or a dye other than black, and has a light-shielding property and heat resistance or weather resistance. From this viewpoint, it is more preferable to contain a pigment other than black.
- the content ratio of the colorant (f) in the solid content of the photosensitive resin composition of the present invention excluding the solvent is preferably 5% by mass or more, more preferably 10% by mass or more, and further preferably 15% by mass or more.
- the content ratio is preferably 70% by mass or less, more preferably 65% by mass or less, and further preferably 60% by mass or less.
- the colorant (f) preferably contains (f1) a pigment.
- the (f) colorant contains the (f1) pigment, it is preferable to contain the (f1) pigment as the colorant other than the (f3) black agent and / or (f4) black.
- (F1) Pigment refers to a compound that colors an object by (f1) pigment being physically adsorbed on the surface of the object or (f1) pigment interacting with the surface of the object. Generally, it is insoluble in solvents. Further, (f1) coloring with a pigment is highly concealed, and fading due to ultraviolet rays or the like is difficult.
- (F1) By containing the pigment, it can be colored in a color with excellent concealability, and the light shielding properties and weather resistance of the film of the resin composition can be improved.
- the number average particle size of the pigment is preferably 1 to 1,000 nm, more preferably 5 to 500 nm, and still more preferably 10 to 200 nm.
- the number average particle diameter of the (f1) pigment is within the above range, the light shielding property of the film of the resin composition and the dispersion stability of the (f1) pigment can be improved.
- the number average particle size of the pigment is a sub-micron particle size distribution measuring device (N4-PLUS; manufactured by Beckman Coulter, Inc.) or a zeta potential / particle size / molecular weight measuring device (Zeta Sizer Nano ZSP; It can be determined by measuring laser scattering (dynamic light scattering method) due to the Brownian motion of the (f1) pigment in the solution using Sysmex Corporation. Moreover, the number average particle diameter of the (f1) pigment in the cured film obtained from a resin composition can be calculated
- Examples of the pigment include organic pigments and inorganic pigments.
- an organic pigment By adding an organic pigment, it is possible to impart colorability or toning to the film of the resin composition.
- it since it is an organic substance, it adjusts the transmission spectrum or absorption spectrum of the film of the resin composition, such as transmitting or blocking light of a desired specific wavelength by chemical structure change or functional conversion, thereby improving toning properties. be able to.
- organic pigments examples include phthalocyanine pigments, anthraquinone pigments, quinacridone pigments, pyranthrone pigments, dioxazine pigments, thioindigo pigments, diketopyrrolopyrrole pigments, quinophthalone pigments, selenium pigments, indoline pigments, Isoindoline pigment, isoindolinone pigment, benzofuranone pigment, perylene pigment, aniline pigment, azo pigment, azomethine pigment, condensed azo pigment, carbon black, metal complex pigment, lake pigment, toner pigment or A fluorescent pigment is mentioned.
- anthraquinone pigments from the viewpoint of heat resistance, anthraquinone pigments, quinacridone pigments, pyranthrone pigments, diketopyrrolopyrrole pigments, benzofuranone pigments, perylene pigments, condensed azo pigments and carbon black are preferred.
- phthalocyanine pigment examples include copper phthalocyanine compounds, halogenated copper phthalocyanine compounds, and metal-free phthalocyanine compounds.
- anthraquinone pigment examples include aminoanthraquinone compounds, diaminoanthraquinone compounds, anthrapyrimidine compounds, flavantron compounds, anthanthrone compounds, indanthrone compounds, pyranthrone compounds, and violanthrone compounds.
- azo pigments examples include disazo compounds and polyazo compounds.
- the film of the resin composition can be provided with colorability or toning.
- the heat resistance and weather resistance of the film of the resin composition can be improved.
- inorganic pigments include titanium oxide, barium carbonate, zirconium oxide, zinc white, zinc sulfide, white lead, calcium carbonate, barium sulfate, white carbon, alumina white, silicon dioxide, kaolin clay, talc, bentonite, brown rice, molybdenum.
- the (f1) pigment is preferably a benzofuranone-based black pigment and / or a perylene-based black pigment.
- the content ratio of the (f1) pigment in the solid content of the photosensitive resin composition of the present invention excluding the solvent is preferably 5% by mass or more, more preferably 10% by mass or more, and further preferably 15% by mass or more.
- the content ratio is preferably 70% by mass or less, more preferably 65% by mass or less, and further preferably 60% by mass or less.
- the (f) colorant preferably contains (f2) a dye.
- the (f2) dye is contained as the colorant other than the (f3) black agent and / or (f4) black.
- (F2) Dye is a compound that colors an object by substitution of a substituent such as an ionic group or a hydroxy group in the dye on the surface structure of the object by chemical adsorption or strong interaction. In general, it is soluble in solvents and the like. In addition, (f2) coloring with a dye has high coloring power and high coloring efficiency because each molecule is adsorbed to an object.
- the dye examples include a direct dye, a reactive dye, a sulfur dye, a vat dye, a sulfur dye, an acid dye, a metal-containing dye, a metal-containing acid dye, a basic dye, a mordant dye, an acid mordant dye, and a disperse dye. , Cationic dyes or fluorescent whitening dyes.
- anthraquinone dyes As dyes, anthraquinone dyes, azo dyes, azine dyes, phthalocyanine dyes, methine dyes, oxazine dyes, quinoline dyes, indigo dyes, indigoid dyes, carbonium dyes, selenium dyes Perinone dyes, perylene dyes, triarylmethane dyes or xanthene dyes.
- Anthraquinone dyes, azo dyes, azine dyes, methine dyes, triarylmethane dyes, and xanthene dyes are preferable from the viewpoints of solubility in solvents and heat resistance described below.
- the film of the resin composition can be imparted with coloring or toning.
- the content ratio of the (f2) dye in the solid content of the photosensitive resin composition of the present invention excluding the solvent is preferably 0.01% by mass or more, more preferably 0.05% by mass or more, and 0.1% by mass. The above is more preferable. When the content ratio is within the above range, the colorability or toning property can be improved. On the other hand, the content ratio is preferably 50% by mass or less, more preferably 45% by mass or less, and further preferably 40% by mass or less. When the content ratio is within the above range, the heat resistance of the cured film can be improved.
- the photosensitive resin composition of the present invention may further contain (g) a dispersant.
- the dispersant is the aforementioned (f1) surface affinity group that interacts with the surface of the pigment or disperse dye, and (f1) the dispersion stabilization structure that improves the dispersion stability of the pigment or disperse dye.
- the compound which has. examples include a polymer chain and / or a substituent having an electrostatic charge.
- (G) By containing a dispersing agent, when a resin composition contains (f1) a pigment or a disperse dye, those dispersion stability can be improved and the resolution after image development can be improved. .
- (f1) pigment is crushed to a number average particle size of 1 ⁇ m or less, the surface area of (f1) pigment particles increases, and (f1) aggregation of pigment particles tends to occur.
- (f1) a pigment is contained, the surface of the crushed (f1) pigment interacts with the surface affinity group of (g) the dispersant, and (g) a dispersion-stabilized structure of the dispersant. Due to the steric hindrance and / or electrostatic repulsion caused by (f1), the aggregation of pigment particles can be inhibited and the dispersion stability can be improved.
- Examples of the (g) dispersant having a surface affinity group include (g) a dispersant having only an amine value, (g) a dispersant having an amine value and an acid value, and (g) a dispersant having only an acid value. Or (g) a dispersant having neither an amine value nor an acid value. (F1) From the viewpoint of improving the dispersion stability of the pigment particles, (g) a dispersant having only an amine value, and (g) a dispersant having an amine value and an acid value are preferred.
- the dispersant having a surface affinity group preferably has a structure in which an amino group and / or an acid group, which is a surface affinity group, forms a salt with an acid and / or a base.
- Examples of the dispersant having only the amine value (g) include “DISPERBYK” (registered trademark) -108, -109, -160, -161, -162, -163, -164, and -164. -166, -167, -168, -182, -184, -184, -185, -2000, -2008, -2009, -2022, -2050, --2055, -2150 -2155, -2163, -2164, or -2061, "BYK” (registered trademark) -9075, -9077, -LP-N6919, -LP-N21116 or -LP-N21324 ( As mentioned above, all are manufactured by Big Chemie Japan Co., Ltd.), “EFKA” (registered trademark) 4015, 4020, 4046, 4047, 4050, 4055, 4055, 4060, 4080, 4300, 4330, 4340, 4340, 4400, 4401, 4402,
- dispersant (g) having an amine value and an acid value examples include “ANTI-TERRA” (registered trademark) -U100 or -204, “DISPERBYK” (registered trademark) -106, -140, and -142.
- Examples of the dispersant having only the acid value (g) include “DISPERBYK” (registered trademark) -102, -110, -111, -118, -170, -171, -174, and the like. -2060 or -2096, “BYK” (registered trademark) -P104, -P105 or -220S (all of which are manufactured by Big Chemie Japan Co., Ltd.) or "SOLPERSE” (registered trademark) 3000, 16000, 17000, 18000, 21000, 26000, 28000, 36000, 36600, 38600, 41000, 41090, 53095, or 55000 (all of which are manufactured by Lubrizol).
- Dispersing agents having neither amine value nor acid value include, for example, “DISPERBYK” (registered trademark) -103, -2152, -2200, or -192 (all of which are the same as Big Chemie Japan ( Or "SOLSPERSE” (registered trademark) 27000, 54000 or X300 (all of which are manufactured by Lubrizol).
- the amine value of the dispersant is preferably 5 mgKOH / g or more, more preferably 8 mgKOH / g or more, and even more preferably 10 mgKOH or more.
- (f1) pigment dispersion stability can be improved.
- the amine value is preferably 150 mgKOH / g or less, more preferably 120 mgKOH / g or less, and even more preferably 100 mgKOH / g or less.
- the storage stability of the resin composition can be improved.
- the amine value here means (g) the mass of potassium hydroxide equivalent to the acid reacting with 1 g of the dispersant, and the unit is mgKOH / g.
- G After neutralizing 1 g of the dispersant with an acid, it can be determined by titrating with an aqueous potassium hydroxide solution. From the value of the amine value, the amine equivalent (unit: g / mol) which is the resin mass per mol of amino groups can be calculated, and (g) the number of amino groups in the dispersant can be determined.
- the acid value of the dispersant is preferably 5 mgKOH / g or more, more preferably 8 mgKOH / g or more, and even more preferably 10 mgKOH or more.
- (f1) pigment dispersion stability can be improved.
- the acid value is preferably 200 mgKOH / g or less, more preferably 170 mgKOH / g or less, and even more preferably 150 mgKOH / g or less.
- the storage stability of the resin composition can be improved.
- the acid value means (g) the mass of potassium hydroxide that reacts with 1 g of the dispersant, and the unit is mgKOH / g.
- G It can obtain
- Examples of the dispersant having a polymer chain (g) include acrylic resin dispersants, polyoxyalkylene ether dispersants, polyester dispersants, polyurethane dispersants, polyol dispersants, polyethyleneimine dispersants or polyallylamine dispersants.
- a dispersing agent is mentioned. From the viewpoint of pattern processability with an alkali developer, an acrylic resin dispersant, a polyoxyalkylene ether dispersant, a polyester dispersant, a polyurethane dispersant, or a polyol dispersant is preferred.
- the content ratio of the (g) dispersant in the photosensitive resin composition of the present invention is (f1 )
- the total of pigment and / or (f2) dye and (g) dispersant is 100% by mass, 1% by mass or more is preferable, 5% by mass or more is more preferable, and 10% by mass or more is more preferable.
- the content ratio is within the above range, (f1) the dispersion stability of the pigment and / or disperse dye can be improved, and the resolution after development can be improved.
- the content ratio is preferably 60% by mass or less, more preferably 55% by mass or less, and further preferably 50% by mass or less. When the content ratio is within the above range, the heat resistance of the cured film can be improved.
- the photosensitive resin composition of the present invention may further contain a sensitizer.
- a sensitizer is a compound that absorbs energy from exposure, generates excited triplet electrons by internal conversion and intersystem crossing, and can undergo energy transfer to the photopolymerization initiator (b2) described above.
- Sensitivity during exposure can be improved by containing a sensitizer. This is because (b2) the photopolymerization initiator or the like has no absorption, the sensitizer absorbs light having a long wavelength, and the energy is transferred from the sensitizer to (b2) the photopolymerization initiator or the like. Thus, it is presumed that the photoreaction efficiency can be improved.
- a thioxanthone sensitizer is preferable.
- the thioxanthone sensitizer include thioxanthone, 2-methylthioxanthone, 2-chlorothioxanthone, 2-isopropylthioxanthone, 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, or 2,4-dichlorothioxanthone.
- the content of the sensitizer in the photosensitive resin composition of the present invention is 0.01 parts by mass or more when the total of (a) the alkali-soluble resin and (d) the radical polymerizable compound is 100 parts by mass.
- 0.1 part by mass or more is more preferable, 0.5 part by mass or more is more preferable, and 1 part by mass or more is particularly preferable.
- the sensitivity at the time of exposure can be improved as content is in the said range.
- the content is preferably 15 parts by mass or less, more preferably 13 parts by mass or less, further preferably 10 parts by mass or less, and particularly preferably 8 parts by mass or less. When the content is within the above range, the resolution after development can be improved and a low taper pattern shape can be obtained.
- the photosensitive resin composition of the present invention may further contain a chain transfer agent.
- the chain transfer agent refers to a compound that can receive a radical from a polymer growth end of a polymer chain obtained by radical polymerization at the time of exposure and can undergo radical transfer to another polymer chain.
- the sensitivity at the time of exposure can be improved by containing a chain transfer agent.
- a chain transfer agent This is presumed to be because radicals generated by exposure undergo radical crosslinking to the deep part of the film by radical transfer to other polymer chains by the chain transfer agent.
- the resin composition contains (f3) a black agent as the colorant (f) described above
- light from exposure is absorbed by the (f3) black agent, so that the light does not reach the deep part of the film.
- radical crosslinking is carried out to the deep part of the film by radical transfer by the chain transfer agent, so that the sensitivity during exposure can be improved.
- a low taper pattern shape can be obtained by including a chain transfer agent.
- a chain transfer agent the molecular weight of the polymer chain obtained by radical polymerization at the time of exposure can be controlled by radical transfer by a chain transfer agent. That is, by containing a chain transfer agent, formation of a remarkable high molecular weight polymer chain due to excessive radical polymerization during exposure is inhibited, and an increase in the softening point of the resulting film is suppressed. Therefore, it is considered that the pattern reflow property at the time of thermosetting is improved and a low taper pattern shape is obtained.
- a thiol chain transfer agent As the chain transfer agent, a thiol chain transfer agent is preferable.
- the thiol chain transfer agent include ⁇ -mercaptopropionic acid, methyl ⁇ -mercaptopropionate, ethyl ⁇ -mercaptopropionate, 2-ethylhexyl ⁇ -mercaptopropionate, n-octyl ⁇ -mercaptopropionate, ⁇ - Methoxybutyl mercaptopropionate, stearyl ⁇ -mercaptopropionate, isononyl ⁇ -mercaptopropionate, ⁇ -mercaptobutanoic acid, methyl ⁇ -mercaptobutanoate, ethyl ⁇ -mercaptobutanoate, 2-ethylhexyl ⁇ -mercaptobutanoate, ⁇ -N-octyl mercaptobutanoate, methoxybutyl ⁇ -mercaptobut
- the content of the chain transfer agent in the photosensitive resin composition of the present invention is 0.01 parts by mass or more when the total of (a) alkali-soluble resin and (d) radical polymerizable compound is 100 parts by mass.
- 0.1 part by mass or more is more preferable, 0.5 part by mass or more is more preferable, and 1 part by mass or more is particularly preferable.
- the content is preferably 15 parts by mass or less, more preferably 13 parts by mass or less, further preferably 10 parts by mass or less, and particularly preferably 8 parts by mass or less.
- the content is within the above range, the resolution after development and the heat resistance of the cured film can be improved.
- the photosensitive resin composition of the present invention may further contain a polymerization inhibitor.
- a polymerization inhibitor is a radical that stops radical polymerization by capturing radicals generated during exposure or radicals at the polymer growth end of polymer chains obtained by radical polymerization during exposure and holding them as stable radicals. A possible compound.
- a phenol polymerization inhibitor is preferable.
- phenol polymerization inhibitors include 4-methoxyphenol, 1,4-hydroquinone, 1,4-benzoquinone, 2-t-butyl-4-methoxyphenol, 3-t-butyl-4-methoxyphenol, 4 -T-butylcatechol, 2,6-di-t-butyl-4-methylphenol, 2,5-di-t-butyl-1,4-hydroquinone or 2,5-di-t-amyl-1,4 -Hydroquinone or "IRGANOX" (registered trademark) 1010, 1035, 1076, 1098, 1135, 1330, 1726, 1425, 1520, 245, 259, 3114, 565 or 295 (All are manufactured by BASF).
- the content of the polymerization inhibitor in the photosensitive resin composition of the present invention is 0.01 parts by mass or more when the total of (a) alkali-soluble resin and (d) radical polymerizable compound is 100 parts by mass.
- 0.03 parts by mass or more is more preferable, 0.05 parts by mass or more is more preferable, and 0.1 parts by mass or more is particularly preferable.
- the content is within the above range, the resolution after development and the heat resistance of the cured film can be improved.
- the content is preferably 10 parts by mass or less, more preferably 8 parts by mass or less, further preferably 5 parts by mass or less, and particularly preferably 3 parts by mass or less. The sensitivity at the time of exposure can be improved as content is in the said range.
- the photosensitive resin composition used in the present invention may contain an adhesion improving agent.
- adhesion improvers vinyltrimethoxysilane, vinyltriethoxysilane, epoxycyclohexylethyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, p-styryltrimethoxysilane, Silane coupling agents such as 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, titanium chelating agents, aluminum chelating agents, aromatic amine compounds and alkoxy groups Examples thereof include compounds obtained by reacting silicon compounds.
- adhesion improving agents By containing these adhesion improving agents, adhesion to an underlying substrate such as a silicon wafer, ITO, SiO 2 , or silicon nitride can be enhanced when developing a photosensitive resin film. Further, resistance to oxygen plasma and UV ozone treatment used for cleaning or the like can be increased.
- the content of the adhesion improving agent is preferably 0.1 parts by mass or more and 10 parts by mass or less with respect to 100 parts by mass of the (a) alkali-soluble resin.
- the photosensitive resin composition used in the present invention may contain a surfactant for the purpose of improving the wettability with the substrate or improving the film thickness uniformity of the coating film, if necessary.
- a surfactant for the purpose of improving the wettability with the substrate or improving the film thickness uniformity of the coating film, if necessary.
- commercially available compounds can be used. Specifically, as the silicone surfactant, SH series, SD series, ST series of Toray Dow Corning Silicone, “BYK” series of Big Chemie Japan, Shin-Etsu Silicone's KP Series, Nippon Oil & Fats 'Disform Series, TOSHIBA Silicone's TSF Series, etc. are listed.
- Fluorosurfactants include Dainippon Ink Industries'"MegaFac (registered trademark)” series, Examples include Sumitomo 3M's Florad series, Asahi Glass's “Surflon (registered trademark)” series, “Asahi Guard (registered trademark)” series, Shin-Akita Kasei's EF series, and Omninova Solution's Polyfox series. , Acrylic and / or methacrylic polymerization
- the surface active agent comprising, Kyoeisha Chemical Co. Poly flow series, manufactured by Kusumoto Chemicals, Inc. "DISPARLON (registered trademark)” series, and the like, but each available from companies, but are not limited to.
- the content of the surfactant is preferably 0.001 part by mass or more and 1 part by mass or less with respect to (a) 100 parts by mass of the alkali-soluble resin.
- the photosensitive resin composition used by this invention may contain the compound which has a phenolic hydroxyl group for the purpose of supplementing the alkali developability of the photosensitive resin composition as needed.
- Examples of the compound having a phenolic hydroxyl group include Bis-Z, BisOC-Z, BisOPP-Z, BisP-CP, Bis26X-Z, BisOTBP-Z, BisOCHP-Z, BisOCR-CP, BisP-MZ, BisP-EZ.
- the resulting photosensitive resin composition hardly dissolves in an alkali developer before exposure, and easily dissolves in an alkali developer upon exposure. Less film loss and easy development in a short time. Therefore, the sensitivity is easily improved.
- the content of the compound having such a phenolic hydroxyl group is preferably 1 part by mass or more and 20 parts by mass or less with respect to 100 parts by mass of (a) the alkali-soluble resin.
- the photosensitive resin composition used in the present invention may contain inorganic particles for the purpose of improving the relative dielectric constant of the cured film, improving the hardness, and reducing the thermal expansion coefficient.
- inorganic particles for the purpose of improving the relative dielectric constant of the cured film, improving the hardness, and reducing the thermal expansion coefficient.
- Preferable specific examples include silicon oxide, titanium oxide, barium titanate, barium sulfate, barium oxide, zirconium oxide, hafnium oxide, tantalum oxide, tungsten oxide, yttrium oxide, alumina, talc and the like.
- the primary particle diameter of these inorganic particles is preferably 100 nm or less, more preferably 60 nm or less.
- the particle size of each inorganic particle was measured with a scanning electron microscope (a scanning electron microscope manufactured by JEOL Ltd., JSM-6301NF).
- the primary particle diameter of the inorganic particles used in the present invention can be calculated by measuring the diameters of 100 particles randomly selected from a scanning electron micrograph and calculating the arithmetic average thereof.
- the content of the inorganic particles is preferably 5 parts by mass or more and 500 parts by mass or less with respect to (a) 100 parts by mass of the alkali-soluble resin.
- the photosensitive resin composition used in the present invention may contain a thermal acid generator.
- the thermal acid generator generates an acid by heating and accelerates the crosslinking reaction of the thermal crosslinking agent.
- Cyclization can be promoted and the mechanical properties of the cured film can be further improved.
- the thermal decomposition starting temperature of the thermal acid generator used in the present invention is preferably 50 ° C. to 270 ° C., more preferably 250 ° C. or less.
- no acid is generated during drying (pre-baking: about 70 to 140 ° C.) after applying the photosensitive resin composition of the present invention to the substrate, and final heating (curing: about: It is preferable to select one that generates an acid at the time of 100 to 400 ° C., since a decrease in sensitivity during development can be suppressed.
- the acid generated from the thermal acid generator used in the present invention is preferably a strong acid.
- a strong acid for example, p-toluenesulfonic acid, arylsulfonic acid such as benzenesulfonic acid, methanesulfonic acid, ethanesulfonic acid, propanesulfonic acid, butanesulfonic acid
- Alkyl sulfonic acids such as haloalkyl sulfonic acids such as trifluoromethyl sulfonic acid are preferred.
- salts such as onium salts or as covalently bonded compounds such as imidosulfonates. Two or more of these may be contained.
- the content of the thermal acid generator used in the present invention is preferably 0.01 parts by mass or more and 10 parts by mass or less with respect to 100 parts by mass of the (a) alkali-soluble resin.
- the photosensitive resin composition used for the cured film of the present invention preferably contains (i) one or more compounds selected from the group consisting of cyclic amides, cyclic ureas, and derivatives thereof. That is, the cured film of the present invention preferably contains (i) one or more compounds selected from the group consisting of cyclic amides, cyclic ureas, and derivatives thereof.
- the compound (i) functions as an acid gas quencher, It is estimated that deterioration and pixel shrinkage can be suppressed, and sufficient long-term reliability as an organic EL device can be given.
- One or more compounds selected from the group consisting of cyclic amides, cyclic ureas and derivatives thereof preferably have a structure represented by the following general formula (11), and contain two or more of these May be.
- u represents an integer of 1 to 4
- Y represents CH or a nitrogen atom.
- R 18 and R 19 each independently represents a hydrogen atom or an organic group having 1 to 20 carbon atoms.
- One or more compounds selected from the group consisting of cyclic amides, cyclic ureas, and derivatives thereof preferably have a boiling point of 210 ° C. or higher from the viewpoint of easily remaining in the film after heat treatment. Moreover, it is preferable that a boiling point is 400 degrees C or less from a viewpoint of suppressing the nonuniformity at the time of application
- cyclic amide, cyclic urea and derivatives thereof include 2-pyrrolidone, N-methyl-2-pyrrolidone (NMP), N-ethyl-2-pyrrolidone, N-propyl-2-pyrrolidone, N-isopropyl- 2-pyrrolidone, N-butyl-2-pyrrolidone, N- (t-butyl) -2-pyrrolidone, N-pentyl-2-pyrrolidone, N-cyclohexyl-2-pyrrolidone, N-methoxypropyl-2-pyrrolidone, N -Ethoxyethyl-2-pyrrolidone, N-methoxybutyl-2-pyrrolidone, N- (2-hydroxyethyl) -2-pyrrolidone, N-phenyl-2-pyrrolidone, N-vinyl-2-pyrrolidone, N, N ' -Dimethylpropylene urea
- N-cyclohexyl-2-pyrrolidone (boiling point: 154 ° C./7 mmHg, converted to normal pressure boiling point: 305 ° C.)
- N- (2-hydroxyethyl) -2-pyrrolidone (boiling point: 175 ° C./10 mmHg, normal (Pressure boiling point conversion: 313 ° C.) is preferable because it has a high boiling point and tends to remain in the film after heat treatment.
- the total content of one or more compounds selected from the group consisting of cyclic amides, cyclic ureas and derivatives thereof is 0.005% by mass or more and 5% by mass or less in 100% by mass of the cured film. Is preferred.
- the addition amount of a compound (i) becomes like this.
- it is 0.1 mass part or more with respect to 100 mass parts of (a) alkali-soluble resin, More preferably, it is 1 mass part. It is above, Preferably it is 15 mass parts or less, More preferably, it is 10 mass parts or less.
- the long-term reliability of an excellent organic EL device can be improved by setting the amount of compound (i) to be 0.1 parts by mass or more, and patterning can be performed with excellent sensitivity by setting it to 15 parts by mass or less. Can do.
- the manufacturing method of the photosensitive resin composition of this invention is demonstrated.
- the above components (a) to (c) and, if necessary, a thermal cross-linking agent, an adhesion improver, a surfactant, a compound having a phenolic hydroxyl group, inorganic particles, a thermal acid generator, and the like are dissolved to obtain a photosensitive material.
- Resin composition can be obtained.
- the dissolution method include stirring and heating. In the case of heating, the heating temperature is preferably set in a range that does not impair the performance of the photosensitive resin composition, and is usually room temperature to 80 ° C.
- each component is not particularly limited, and for example, there is a method of sequentially dissolving compounds having low solubility.
- components that tend to generate bubbles when stirring and dissolving such as surfactants and some adhesion improvers, by dissolving other components and adding them last, poor dissolution of other components due to the generation of bubbles Can be prevented.
- the obtained photosensitive resin composition is preferably filtered using a filtration filter to remove dust and particles.
- a filtration filter to remove dust and particles.
- the filter pore diameter include, but are not limited to, 0.5 ⁇ m, 0.2 ⁇ m, 0.1 ⁇ m, 0.07 ⁇ m, 0.05 ⁇ m, and 0.02 ⁇ m.
- the material for the filter include polypropylene (PP), polyethylene (PE), nylon (NY), polytetrafluoroethylene (PTFE), and polyethylene and nylon are preferable.
- the obtained cured film can be suitably used as a gate insulating layer or an interlayer insulating layer of a thin film transistor.
- a method for producing a cured film using the photosensitive resin composition of the present invention includes a step of coating the photosensitive resin composition on a substrate to form a photosensitive resin film, a step of drying the photosensitive resin film, It includes a step of exposing the photosensitive resin film, a step of developing the exposed photosensitive resin film, and a step of heat curing. Details of each step will be described below.
- the photosensitive resin composition of the present invention is applied by a spin coating method, a slit coating method, a dip coating method, a spray coating method, a printing method, or the like to obtain a coating film of the photosensitive resin composition.
- the slit coat method is preferably used.
- the slit coating method can be applied with a small amount of coating liquid, and is advantageous for cost reduction.
- the amount of coating solution required for the slit coating method is, for example, about 1/5 to 1/10 as compared with the spin coating method.
- coating The thing marketed from the some manufacturer can be used. Specifically, Dainippon Screen Mfg. Co., Ltd.
- the coating speed is generally in the range of 10 mm / second to 400 mm / second.
- the film thickness of the coating film varies depending on the solid content concentration, viscosity, etc. of the photosensitive resin composition, but is usually applied so that the film thickness after drying is 0.1 to 10 ⁇ m, preferably 0.3 to 5 ⁇ m.
- the substrate on which the photosensitive resin composition is applied may be pretreated with the above-described adhesion improving agent in advance.
- a solution in which 0.5 to 20% by mass of an adhesion improver is dissolved in a solvent such as isopropanol, ethanol, methanol, water, tetrahydrofuran, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, diethyl adipate, or the like is used.
- a method of treating the substrate surface examples include spin coating, slit die coating, bar coating, dip coating, spray coating, and steam treatment.
- the substrate on which the coating film is formed is dried under reduced pressure.
- a substrate on which a coating film is formed is placed on proxy pins arranged in a vacuum chamber, and the inside of the vacuum chamber is decompressed and dried under reduced pressure.
- the proxy pin height is preferably about 2 to 20 mm, more preferably 2 to 10 mm.
- the vacuum drying speed depends on the vacuum chamber volume, the vacuum pump capacity, the pipe diameter between the chamber and the pump, etc., for example, under conditions where the pressure in the vacuum chamber is reduced to 40 Pa after 60 seconds in the absence of a coating substrate. Set and used.
- the general vacuum drying time is often about 30 to 100 seconds, and the ultimate pressure in the vacuum chamber at the end of the vacuum drying is usually 100 Pa or less with the coated substrate. By setting the ultimate pressure to 100 Pa or less, the coating film surface can be brought into a dry state without stickiness, whereby surface contamination and generation of particles can be suppressed in subsequent substrate transport.
- the coating film is generally dried by heating. This process is also called pre-baking. Drying uses a hot plate, oven, infrared rays and the like. When a hot plate is used, the coating film is heated directly on the plate or on a jig such as a proxy pin installed on the plate.
- a hot plate there is a metal material such as aluminum or stainless steel, or a synthetic resin such as polyimide resin or “Teflon (registered trademark)”. Any material can be used as long as it has heat resistance. .
- the height of the proxy pin varies depending on the size of the substrate, the type of coating film, the purpose of heating, etc., but is preferably about 0.1 to 10 mm.
- the heating temperature varies depending on the type and purpose of the coating film, and it is preferably performed in the range of 50 ° C. to 180 ° C. for 1 minute to several hours.
- Exposure is performed by irradiating actinic radiation on a photosensitive resin film through a mask having a desired pattern.
- actinic radiation there are ultraviolet rays, visible rays, electron beams, X-rays and the like.
- i rays 365 nm
- h rays 405 nm
- g rays 436 nm
- a desired pattern is formed by removing an exposed portion in the case of a positive type and a non-exposed portion in the case of a negative type using a developer.
- a developer in both positive and negative types, tetramethylammonium hydroxide, diethanolamine, diethylaminoethanol, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, triethylamine, diethylamine, methylamine, dimethylamine, An aqueous solution of a compound exhibiting alkalinity such as dimethylaminoethyl acetate, dimethylaminoethanol, dimethylaminoethyl methacrylate, cyclohexylamine, ethylenediamine, and hexamethylenediamine is preferred.
- these alkaline aqueous solutions may contain polar solvents such as N-methyl-2-pyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, ⁇ -butyrolactone, dimethylacrylamide, methanol, ethanol, Alcohols such as isopropanol, esters such as ethyl lactate and propylene glycol monomethyl ether acetate, ketones such as cyclopentanone, cyclohexanone, isobutyl ketone, and methyl isobutyl ketone may be added singly or in combination. Good. As a developing method, methods such as spraying, paddle, dipping, and ultrasonic waves are possible.
- polar solvents such as N-methyl-2-pyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, ⁇ -butyrolactone, dimethylacrylamide, methanol
- alcohols such as ethanol and isopropyl alcohol
- esters such as ethyl lactate and propylene glycol monomethyl ether acetate may be added to distilled water for rinsing treatment.
- heat curing is performed. Since components having low heat resistance can be removed by heat curing, heat resistance and chemical resistance can be improved.
- the photosensitive resin composition of the present invention contains an alkali-soluble resin selected from a polyimide precursor and a polybenzoxazole precursor, a copolymer thereof, or a copolymer of polyimide with them, heating When an imide ring or an oxazole ring can be formed by curing, heat resistance and chemical resistance can be improved, and when it contains a compound having at least two alkoxymethyl groups, methylol groups, epoxy groups, or oxytanyl groups The thermal crosslinking reaction can be advanced by heat curing, and the heat resistance and chemical resistance can be improved.
- This heat curing is carried out for 5 minutes to 5 hours by selecting the temperature and raising the temperature stepwise, or selecting a certain temperature range and continuously raising the temperature.
- heat treatment is performed at 150 ° C. and 250 ° C. for 30 minutes each.
- a method such as linearly raising the temperature from room temperature to 300 ° C. over 2 hours can be mentioned.
- the heat curing conditions in the present invention are preferably 300 ° C. or higher and more preferably 350 ° C. or higher in terms of reducing the amount of outgas generated from the cured film.
- 500 degrees C or less is preferable at the point which gives sufficient film toughness to a cured film, and 450 degrees C or less is more preferable.
- the photosensitive sheet is defined as a sheet obtained by applying a photosensitive resin composition on a peelable substrate and drying it.
- seat formed from the photosensitive resin composition of this invention when it has a protective film in the said photosensitive sheet
- a photosensitive resin film is obtained.
- the photosensitive sheet can be obtained by applying and drying the photosensitive resin composition of the present invention on a support film composed of polyethylene terephthalate or the like which is a peelable substrate.
- the thermocompression bonding can be performed by a heat press process, a heat laminating process, a heat vacuum laminating process, or the like.
- the bonding temperature is preferably 40 ° C. or higher from the viewpoint of adhesion to the substrate and embedding. Further, when the photosensitive sheet has photosensitivity, the bonding temperature is preferably 140 ° C. or lower in order to prevent the photosensitive sheet from being cured at the time of bonding and reducing the resolution of pattern formation in the exposure / development process.
- the photosensitive resin film obtained by laminating the photosensitive sheet to the substrate follows the steps of exposing the photosensitive resin film, developing the exposed photosensitive resin film, and heating and curing. Thus, a cured film can be formed.
- the cured film obtained by curing the photosensitive resin composition or photosensitive sheet of the present invention can be used for electronic components such as organic EL display devices, semiconductor devices, and multilayer wiring boards.
- electronic components such as organic EL display devices, semiconductor devices, and multilayer wiring boards.
- Examples of the electronic device having a surface protective film, an interlayer insulating film, or the like on which the cured film of the present invention is disposed include MRAM having low heat resistance. That is, the cured film of the present invention is suitable for a surface protective film of MRAM.
- MRAM Metal-organic random access memory
- polymer memory Polymer® Ferroelectric RAM: PFRAM
- phase change memory Phase Change® RAM: PCRAM, or Ovonics® Unified Memory: OUM
- the cured film of the present invention is also suitable for these surface protective films.
- a display device including a first electrode formed on a substrate and a second electrode provided to face the first electrode, specifically, for example, an LCD, an ECD, an ELD, an organic electroluminescent element It can be used for an insulating layer of the display device (organic electroluminescence device) used.
- an organic EL display device will be described as an example.
- the organic EL display device of the present invention has a drive circuit, a planarizing layer, a first electrode, an insulating layer, a light emitting layer, and a second electrode on a substrate, and the planarizing layer and / or the insulating layer is cured according to the present invention. It consists of a membrane. Taking an active matrix display device as an example, it has a TFT on a substrate such as a glass or a resin film, and a wiring located on a side portion of the TFT and connected to the TFT, and covers the unevenness thereon. Thus, the planarization layer is provided, and the display element is provided on the planarization layer.
- the substrate having the above drive circuit is an organic EL display device made of a resin film.
- the cured film obtained by curing the photosensitive resin composition or the photosensitive sheet of the present invention is used as an insulating layer or a flattening layer of such a flexible display, it is particularly preferably used because of excellent flexibility.
- polyimide is particularly preferable as the resin film.
- FIG. 1 shows a cross-sectional view of an example of a TFT substrate.
- bottom-gate or top-gate TFTs (thin film transistors) 1 are provided in a matrix, and the insulating layer 3 is formed so as to cover the TFTs 1.
- a wiring 2 connected to the TFT 1 is provided on the insulating layer 3.
- a planarizing layer 4 is provided on the insulating layer 3 so as to bury the wiring 2.
- a contact hole 7 reaching the wiring 2 is provided in the planarization layer 4.
- An ITO (transparent electrode) 5 is formed on the planarizing layer 4 while being connected to the wiring 2 via the contact hole 7.
- ITO5 becomes an electrode of a display element (for example, organic EL element).
- the organic EL element may be a top emission type that emits emitted light from the side opposite to the substrate 6 or a bottom emission type that extracts light from the substrate 6 side. In this manner, an active matrix organic EL display device in which each organic EL element is connected with the TFT 1 for driving the organic EL element is obtained.
- the insulating layer 3, the planarizing layer 4, and / or the insulating layer 8 are a step of forming a photosensitive resin film made of the resin composition or resin sheet of the present invention, a step of exposing the photosensitive resin film, It can form by the process of developing the exposed photosensitive resin film, and the process of heat-processing the developed photosensitive resin film.
- An organic EL display device can be obtained from the manufacturing method having these steps.
- the photosensitive resin composition of the present invention is also suitably used for a fan-out wafer level package (fan-out WLP).
- the fan-out WLP is provided with an extended portion using a sealing resin such as epoxy resin around the semiconductor chip, rewiring from the electrode on the semiconductor chip to the extended portion, and mounting a solder ball on the extended portion.
- a sealing resin such as epoxy resin around the semiconductor chip
- This is a semiconductor package that secures the necessary number of terminals.
- wiring is installed so as to straddle the boundary line formed by the main surface of the semiconductor chip and the main surface of the sealing resin.
- an interlayer insulating film is formed on a base material composed of two or more kinds of materials such as a semiconductor chip provided with metal wiring and a sealing resin, and wiring is formed on the interlayer insulating film.
- a base material composed of two or more kinds of materials such as a semiconductor chip provided with metal wiring and a sealing resin
- wiring is formed on the interlayer insulating film.
- a semiconductor package of a type in which a semiconductor chip is embedded in a recess formed in a glass epoxy resin substrate wiring is installed so as to straddle the boundary line between the main surface of the semiconductor chip and the main surface of the printed circuit board.
- an interlayer insulating film is formed on a substrate composed of two or more materials, and wiring is formed on the interlayer insulating film.
- the cured film formed by curing the photosensitive resin composition of the present invention has high adhesion to a semiconductor chip provided with metal wiring, and also has high adhesion to an epoxy resin or the like and a sealing resin. It is suitably used as an interlayer insulating film provided on a substrate composed of more than one kind of material.
- TMAH tetramethylammonium
- the prepared pre-baked film was subjected to a sensitivity measurement gray scale mask (MDRM MODEL 4000-5-FS; manufactured by Opto-Line International).
- MDRM MODEL 4000-5-FS sensitivity measurement gray scale mask
- the PI film substrate having the prepared cured film was cut into 50 mm length ⁇ 10 mm width.
- the PI film substrate was held for 30 seconds in a state where the PI film substrate was bent at 180 ° on a line of 25 mm in length with the surface of the cured film facing outside.
- the folded PI film substrate is opened, and using a FPD inspection microscope (MX-61L; manufactured by Olympus Corporation), the bent portion on the 25 mm vertical line of the cured film surface is observed, and the appearance of the cured film surface is observed. Changes were evaluated. The case where there was no peeling of the cured film from the PI film substrate and there was no change in appearance such as cracks or deformation on the surface of the cured film was regarded as acceptable (A), and the others were regarded as unacceptable (B).
- FIG. 1 is a schematic view of a manufacturing procedure of an organic EL display device.
- an ITO transparent conductive film 10 nm was formed on the entire surface of a 38 mm mm ⁇ 46 mm non-alkali glass substrate 9 by sputtering and etched as the first electrode 10.
- an auxiliary electrode 11 for taking out the second electrode was also formed.
- the obtained substrate was subjected to ultrasonic cleaning with Semico Clean 56 (trade name, manufactured by Furuuchi Chemical Co., Ltd.) for 10 minutes, and then washed with ultrapure water.
- Semico Clean 56 trade name, manufactured by Furuuchi Chemical Co., Ltd.
- the photosensitive resin composition shown in Table 5 was applied to the entire surface of the substrate by spin coating, and prebaked on a hot plate at 120 ° C. for 2 minutes. This film was exposed to UV through a photomask and then developed with a 2.38 mass% TMAH aqueous solution to dissolve unnecessary portions and rinsed with pure water.
- the obtained resin pattern was heat-treated at 250 ° C. for 1 hour under a nitrogen atmosphere using a high-temperature inert gas oven (INH-9CD-S; manufactured by Koyo Thermo System Co., Ltd.).
- openings having a width of 70 ⁇ m and a length of 260 ⁇ m are arranged with a pitch of 155 ⁇ m in the width direction and a pitch of 465 ⁇ m in the length direction, and the insulating layer 12 having a shape in which each opening exposes the first electrode is formed on the substrate. It was limited to the effective area. In this way, an insulating layer having an insulating layer aperture ratio of 25% was formed in the effective area of the substrate having a square of 16 mm on one side. The thickness of the insulating layer was about 1.0 ⁇ m.
- an organic EL layer 13 including a light emitting layer was formed by a vacuum deposition method.
- the degree of vacuum at the time of vapor deposition was 1 ⁇ 10 ⁇ 3 Pa or less, and the substrate was rotated with respect to the vapor deposition source during the vapor deposition.
- 10 nm of the compound (HT-1) was deposited as a hole injection layer, and 50 nm of the compound (HT-2) was deposited as a hole transport layer.
- a compound (GH-1) as a host material and a compound (GD-1) as a dopant material were deposited on the light emitting layer in a thickness of 40 nm so that the doping concentration was 10%.
- the compound (ET-1) and the compound (LiQ) as an electron transporting material were laminated at a volume ratio of 1: 1 to a thickness of 40 nm.
- the structure of the compound used in the organic EL layer is shown below.
- a cap-shaped glass plate is sealed by bonding with an epoxy resin adhesive in a low-humidity nitrogen atmosphere, and a top emission type organic EL that is a square with a side of 5 mm on one substrate.
- the film thickness said here is a display value in a crystal oscillation type film thickness monitor.
- the produced organic EL display device was placed on a hot plate heated to 80 ° C. with the light emitting surface facing upward, and irradiated with UV light having a wavelength of 365 nm and an illuminance of 0.6 mW / cm 2 .
- UV light having a wavelength of 365 nm and an illuminance of 0.6 mW / cm 2 .
- the area ratio of the light emitting portion to the area of the light emitting pixel was measured. did. If the pixel light emission area ratio after 1000 hours by this evaluation method is 80% or more, it can be said that long-term reliability is excellent, and 90% or more is more preferable.
- Example 1 Under a dry nitrogen stream, 15.11 g (0.025 mol) of the hydroxyl group-containing diamine compound ( ⁇ ) obtained in Synthesis Example 1; 3.66 g (0.01 mol) of BAHF; 0.62 g (0.0025 mol) of SiDA Dissolved in 200 g of NMP. TMEG 20.51g (0.05mol) was added with NMP50g here, and it stirred at 40 degreeC for 1 hour. Thereafter, 2.73 g (0.025 mol) of MAP was added as a terminal blocking agent, and the mixture was stirred at 40 ° C. for 1 hour.
- Example 2 3.66 g (0.01 mol) of BAHF was 3.62 g (0.01 mol) of BIS-AT-AF, and 2.73 g (0.025 mol) of MAP was used as an end-capping agent to 4.13 g (0.025 mol) of ABP.
- a polyamic acid ester resin (B) was obtained in the same manner as in Example 1.
- Example 3 Under a dry nitrogen stream, 15.56 g (0.0425 mol) of BAHF and 0.62 g (0.0025 mol) of SiDA were dissolved in 100 g of NMP. TMEG 20.51g (0.05mol) was added with NMP10g here, and it was made to react at 60 degreeC for 1 hour. Thereafter, 1.09 g (0.01 mol) of MAP was added as a terminal blocking agent, and stirring was further continued at 60 ° C. for 1 hour. Subsequently, it stirred at 180 degreeC for 4 hours, and after completion
- TMEG 20.51g (0.05mol) was added with NMP10g here, and it was made to react at 60 degreeC for 1 hour. There
- BAHF 15.56 g (0.0425 mol) is 10.98 g (0.03 mol)
- MAP 1.09 g (0.01 mol) is ABP 1.65 g (0.01 mol)
- hydroxyl group-containing diamine compound ( ⁇ ) 6 A closed ring polyimide resin (D) was obtained in the same manner as in Example 3 except that .05 g (0.01 mol) was added.
- Example 5 Under a dry nitrogen stream, 11.9 g (0.0325 mol) of BAHF, 5.43 g (0.015 mol) of BIS-AT-AF, and 0.62 g (0.003 mol) of SiDA were dissolved in 100 g of NMP. TMEG 15.39g (0.0375mol) was added here with NMP10g, and it was made to react at 60 degreeC for 1 hour. Thereafter, 2.45 g (0.025 mol) of MA was added as a terminal blocking agent, and stirring was further continued at 60 ° C. for 1 hour. Subsequently, it stirred at 180 degreeC for 4 hours, and after completion
- E closed ring polyimide resin
- Example 7 Instead of 15.56 g (0.0425 mol) of BAHF, 7.64 g (0.02 mol) of BIS-AT-AF, 4.0 g (0.02 mol) of DAE, and 1.64 g (0.01 mol) of MAP A closed ring polyimide resin (G) was obtained in the same manner as in Example 3 except that the amount was 0.015 mol).
- Example 8 Under a dry nitrogen stream, 13.21 g (0.0375 mol) of 2,2′-bis (trifluoromethyl) -5,5′-dihydroxybenzidine (TFM-DHB) and 0.62 g (0.0025 mol) of SiDA were added to NMP. Dissolved in 200 g. TMEG 20.51g (0.05mol) was added with NMP50g here, and it stirred at 60 degreeC for 1 hour. Thereafter, 2.73 g (0.025 mol) of MAP was added as a terminal blocking agent, and stirring was further continued at 60 ° C. for 1 hour.
- TMP-DHB 2,2′-bis (trifluoromethyl) -5,5′-dihydroxybenzidine
- Example 9 A closed ring polyimide resin (I) was prepared in the same manner as in Example 3 except that 15.56 g (0.0425 mol) of BAHF was changed to 10.07 g (0.0275 mol) and 3.0 g (0.015 mol) of DAE was added. Obtained.
- Example 10 10 g of the resin (C), 3.0 g of the quinonediazide compound (b1-3) and 1.0 g of the crosslinking agent VG-3101L (e-3) were added to 50 g of GBL to obtain a varnish C2 of a positive photosensitive resin composition. Using the obtained varnish C2, as described above, sensitivity evaluation, residual film ratio evaluation, bending property evaluation, and long-term reliability evaluation of the organic EL display device were performed. The evaluation results are shown in Table 2.
- Example 11 10 g of resin (D), 3.0 g of quinonediazide compound (b1-3), 1.0 g of an alkoxymethyl group-containing thermal crosslinking agent (e-1) and 1.0 g of phenol compound BisP-AF (h-1) are added to 50 g of GBL.
- a varnish D2 of a positive photosensitive resin composition was obtained.
- evaluation of sensitivity evaluation, remaining film rate evaluation, bendability, and long-term reliability evaluation of an organic EL display device was performed using the obtained varnish D2. The evaluation results are shown in Table 2.
- Example 12 10 g of the resin (G), 3.0 g of the quinonediazide compound (b1-1) and 1.0 g of the crosslinking agent VG-3101L (e-3) were added to 50 g of GBL to obtain a varnish G2 of a positive photosensitive resin composition. As described above, the obtained varnish G2 was used for sensitivity evaluation, residual film rate evaluation, bendability evaluation, and long-term reliability evaluation of the organic EL display device. The evaluation results are shown in Table 2.
- the film thickness of the obtained cured film was measured, and 1 ⁇ 5 cm was cut out and was adsorbed and trapped by the purge and trap method.
- the collected cured film was heated at 400 ° C. for 60 minutes using helium as a purge gas, and the desorbed components were collected in an adsorption tube.
- the collected components were thermally desorbed using a thermal desorption apparatus at a primary desorption condition of 260 ° C. for 15 minutes, a secondary adsorption desorption condition of ⁇ 27 ° C. and 320 ° C.
- a GC-MS apparatus 7890 / GC-MS analysis was performed using 5975C (manufactured by Agilent) under the conditions of column temperature: 40 to 300 ° C., carrier gas: helium (1.5 mL / min), scan range: m / Z 29 to 600.
- the amount of gas generation was calculated by preparing a calibration curve by GC-MS analysis of NMP under the same conditions as above. The obtained value ( ⁇ g) was divided by an area of 5 cm 2 to obtain ⁇ g / cm 2 . The value was divided by 100 times the specific gravity of the alkali-soluble resin (a) multiplied by the film thickness, and the total content of NMP in the cured film was calculated to be 0.5% by mass.
- ⁇ Preparation Example 1> As a resin, 138.0 g of a 30% by mass MBA solution of the resin (C) obtained in Example 3 was used as a dispersant, 13.8 g of S-20000, 685.4 g of MBA as a solvent, and 685.4 g of a colorant. , 82.8 g of Bk-S0100CF were weighed and mixed, and stirred for 20 minutes using a high-speed disperser (Homodisper 2.5 type; manufactured by Primix Co., Ltd.) to obtain a preliminary dispersion.
- a high-speed disperser Homodisper 2.5 type; manufactured by Primix Co., Ltd.
- Ultra Apex Mill (UAM-015; Kotobuki Kogyo Co., Ltd.) comprising a centrifugal separator filled with 75% 0.30 mm ⁇ zirconia pulverized balls (YTZ; manufactured by Tosoh Corporation) as ceramic beads for pigment dispersion
- YTZ zirconia pulverized balls
- the number average particle diameter of the pigment in the obtained pigment dispersion was 100 nm.
- Preparation Example 2 A pigment dispersion (Bk-2) was obtained in the same manner as in Preparation Example 1, except that the resin (M) was used instead of the resin (C).
- Example 14 Under a yellow light, 0.25 g of NCI-831 was weighed, 10.0 g of MBA was added, and dissolved by stirring. Next, 3.5 g of a 30% by mass MBA solution of the resin (A) obtained in Example 1 and 1.5 g of an 80% by mass MBA solution of DPHA were added and stirred to prepare a mixed solution as a uniform solution. Obtained. Next, 16.67 g of the pigment dispersion (Bk-1) obtained in Preparation Example 1 was weighed, and the prepared liquid obtained above was added thereto and stirred to obtain a uniform solution. Then, the obtained solution was filtered with a 0.45 ⁇ m ⁇ filter to obtain a varnish BA of a negative photosensitive resin composition. As described above, the obtained varnish BA was used for sensitivity evaluation, residual film ratio evaluation, bendability evaluation, and long-term reliability evaluation of an organic EL display device. The composition is shown in Table 3, and the evaluation results are shown in Table 4.
- Examples 15 to 17 and Comparative Examples 7 to 11 In the same manner as in Example 14, varnishes BB to BN of the photosensitive resin composition were prepared with the compositions shown in Table 3. Using each of the obtained compositions, in the same manner as in Example 14, evaluation of sensitivity, evaluation of the remaining film rate, evaluation of bendability, and long-term reliability of the organic EL display device were performed. The evaluation results are shown in Table 4.
- Tables 3 and 4 show the compositions and evaluation results for Examples 14 to 17 and Comparative Examples 7 to 11, respectively.
- TFT Thin Film Transistor
- Wiring 3 TFT insulating layer 4: Planarizing layer 5: ITO (transparent electrode) 6: Substrate 7: Contact hole 8: Insulating layer 9: Glass substrate 10: First electrode (non-transparent electrode) 11: Auxiliary electrode 12: Insulating layer 13: Organic EL layer 14: Second electrode (transparent electrode)
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Abstract
Description
本発明の樹脂は、上記一般式(1)で表される構造単位を有するアルカリ可溶性ポリイミドもしくはポリイミド前駆体またはそれらの共重合体から選ばれるアルカリ可溶性樹脂である。
本発明の(a)アルカリ可溶性樹脂は、フッ素原子を有することが好ましい。一般式(1)中、R1は、ジアミンに由来する構造である。一般式(1)中において、R1が、フッ素原子を有する有機基であることが好ましい。フッ素原子を有することにより、アルカリ現像の際に膜の表面に撥水性が付与され、表面からのしみこみを抑えることができるため、未露光部のタックや加工パターンに現像残渣のない、高残膜率の感光性樹脂膜が得られる。
また、本発明の一般式(1)で表される構造を有する樹脂は、スルホン酸基、チオール基などを含むことができる。スルホン酸基、チオール基を適度に有する樹脂を用いることで、適度なアルカリ可溶性を有する感光性樹脂組成物となる。
上記一般式(2)で表されるモノアミンの好ましい例として、2-アミノフェノール、3-アミノフェノール(MAP)、2-アミノ-m-クレゾール、2-アミノ-p-クレゾール、3-アミノ-o-クレゾール、4-アミノ-o-クレゾール、4-アミノ-m-クレゾール、5-アミノ-o-クレゾール、6-アミノ-m-クレゾール、4-アミノ-2,3-キシレノール、4-アミノ-3,5-キシレノール、6-アミノ-2,4-キシレノール、2-アミノ-4-エチルフェノール、3-アミノ-4-エチルフェノール、2-アミノ-4-tert-ブチルフェノール、2-アミノ-4-フェニルフェノール、4-アミノ-2,6-ジフェニルフェノール、4-アミノサリチル酸、5-アミノサリチル酸、6-アミノサリチル酸、2-アミノ安息香酸、3-アミノ安息香酸、4-アミノ安息香酸、2-アミノ-m-トルエン酸、3-アミノ-o-トルエン酸、3-アミノ-p-トルエン酸、4-アミノ-m-トルエン酸、6-アミノ-o-トルエン酸、6-アミノ-m-トルエン酸、3-アミノベンゼンスルホン酸、4-アミノベンゼンスルホン酸、4-アミノトルエン-3-スルホン酸などを挙げることができる。これらを2種以上用いてもよく、それ以外の末端封止剤を併用しても良い。
本発明の感光性樹脂組成物は(b)感光性化合物を含有する。感光性化合物としては、(b1)光酸発生剤や、(b2)光重合開始剤が挙げられる。(b1)光酸発生剤は、光照射されることにより酸が発生し、光照射部のアルカリ水溶液に対する溶解性が増大する特性を与える化合物であり、(b2)光重合開始剤とは、露光によって結合開裂および/または反応してラジカルを発生する化合物をいう。
本発明の感光性樹脂組成物は、(c)溶剤を含有する。溶剤としては、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、ジエチレングリコールジメチルエーテル、ジエチレングリコールエチルメチルエーテルなどのエーテル類、エチレングリコールモノメチルエーテルアセテート、プロピレングリコールモノメチルエーテルアセテート、酢酸エチル、酢酸ブチル、乳酸メチル、乳酸エチル、乳酸ブチルなどのエステル類、エタノール、イソプロパノール、ブタノール、ペンタノール、3-メチル-2-ブタノール、3-メチル-3-メトキシブタノールなどのアルコール類、メチルエチルケトン、メチルイソブチルケトン、メチルアミルケトン、ジイソブチルケトン、シクロペンタノン、ジアセトンアルコールなどのケトン類、N-メチル-2-ピロリドン、γ-ブチロラクトン、N,N-ジメチルホルムアミド、N,N-ジメチルアセトアミド、ジメチルスルホキシド、1,3-ジメチル-2-イミダゾリジノンなどの極性の非プロトン性溶媒、トルエン、キシレンなどの芳香族炭化水素類などが挙げられる。これらを2種以上含有してもよい。(c)溶剤の含有量は、(a)アルカリ可溶性樹脂100質量部に対して、好ましくは50質量部以上、より好ましくは100質量部以上であり、また、好ましくは2000質量部以下、より好ましくは1500質量部以下である。
本発明の感光性樹脂組成物は、さらに、(d)ラジカル重合性化合物を含有してもよい。
本発明の感光性樹脂組成物は、さらに(e)熱架橋剤を含有することができる。熱架橋剤とは、アルコキシメチル基、メチロール基、エポキシ基、オキセタニル基をはじめとする熱反応性の官能基を分子内に少なくとも2つ有する化合物を指す。熱架橋剤は(a)アルカリ可溶性樹脂またはその他添加成分を架橋し、熱硬化後の膜の耐熱性、耐薬品性および硬度を高めることができる。
本発明の感光性樹脂組成物は、さらに、(f)着色剤を含有してもよい。
また、前記(f)着色剤は、(f3)黒色剤および/または(f4)黒色以外の着色剤であることが好ましい。
本発明の感光性樹脂組成物は、前記(f)着色剤が、(f1)顔料を含有することが好ましい。前記(f)着色剤が、(f1)顔料を含有する態様としては、前記(f3)黒色剤および/または(f4)黒色以外の着色剤として、(f1)顔料を含有することが好ましい。
本発明の感光性樹脂組成物としては、前記(f)着色剤が、(f2)染料を含有することが好ましい。前記(f)着色剤が、(f2)染料を含有する態様としては、前記(f3)黒色剤および/または(f4)黒色以外の着色剤として、(f2)染料を含有することが好ましい。
本発明の感光性樹脂組成物は、さらに、(g)分散剤を含有してもよい。
本発明の感光性樹脂組成物は、さらに、増感剤を含有してもよい。
本発明の感光性樹脂組成物は、さらに、連鎖移動剤を含有してもよい。
本発明の感光性樹脂組成物は、さらに、重合禁止剤を含有してもよい。
本発明で用いられる感光性樹脂組成物は、密着改良剤を含有してもよい。密着改良剤としては、ビニルトリメトキシシラン、ビニルトリエトキシシラン、エポキシシクロヘキシルエチルトリメトキシシラン、3-グリシドキシプロピルトリメトキシシラン、3-グリシドキシプロピルトリエトキシシラン、p-スチリルトリメトキシシラン、3-アミノプロピルトリメトキシシラン、3-アミノプロピルトリエトキシシラン、N-フェニル-3-アミノプロピルトリメトキシシランなどのシランカップリング剤、チタンキレート剤、アルミキレート剤、芳香族アミン化合物とアルコキシ基含有ケイ素化合物を反応させて得られる化合物などが挙げられる。これらを2種以上含有してもよい。これらの密着改良剤を含有することにより、感光性樹脂膜を現像する場合などに、シリコンウエハ、ITO、SiO2、窒化ケイ素などの下地基材との密着性を高めることができる。また、洗浄などに用いられる酸素プラズマ、UVオゾン処理に対する耐性を高めることができる。密着改良剤の含有量は、(a)アルカリ可溶性樹脂100質量部に対して0.1質量部以上10質量部以下が好ましい。
本発明で用いられる感光性樹脂組成物は、必要に応じて基板との濡れ性を向上させたり、塗布膜の膜厚均一性を向上させたりする目的で界面活性剤を含有してもよい。界面活性剤は市販の化合物を用いることができ、具体的にはシリコーン系界面活性剤としては、東レダウコーニングシリコーン社のSHシリーズ、SDシリーズ、STシリーズ、ビックケミー・ジャパン社の“BYK”シリーズ、信越シリコーン社のKPシリーズ、日本油脂社のディスフォームシリーズ、東芝シリコーン社のTSFシリーズなどが挙げられ、フッ素系界面活性剤としては、大日本インキ工業社の“メガファック(登録商標)”シリーズ、住友スリーエム社のフロラードシリーズ、旭硝子社の“サーフロン(登録商標)”シリーズ、“アサヒガード(登録商標)”シリーズ、新秋田化成社のEFシリーズ、オムノヴァ・ソルーション社のポリフォックスシリーズなどが挙げられ、アクリル系および/またはメタクリル系の重合物からなる界面活性剤としては、共栄社化学社のポリフローシリーズ、楠本化成社の“ディスパロン(登録商標)”シリーズなどが挙げられ、それぞれ各社から入手できるが、これらに限定されない。
本発明で用いられる感光性樹脂組成物は、必要に応じて感光性樹脂組成物のアルカリ現像性を補う目的で、フェノール性水酸基を有する化合物を含有してもよい。フェノール性水酸基を有する化合物としては、例えば、Bis-Z、BisOC-Z、BisOPP-Z、BisP-CP、Bis26X-Z、BisOTBP-Z、BisOCHP-Z、BisOCR-CP、BisP-MZ、BisP-EZ、Bis26X-CP、BisP-PZ、BisP-IPZ、BisCRIPZ、BisOCP-IPZ、BisOIPP-CP、Bis26X-IPZ、BisOTBP-CP、TekP-4HBPA(テトラキスP-DO-BPA)、TrisPHAP、TrisP-PA、TrisP-PHBA、TrisP-SA、TrisOCR-PA、BisOFP-Z、BisRS-2P、BisPG-26X、BisRS-3P、BisOC-OCHP、BisPC-OCHP、Bis25X-OCHP、Bis26X-OCHP、BisOCHP-OC、Bis236T-OCHP、メチレントリス-FR-CR、BisRS-26X、BisRS-OCHP、(以上、商品名、本州化学工業(株)から入手できる)、BIR-OC、BIP-PCBIR-PC、BIR-PTBP、BIR-PCHP、BIP-BIOC-F、4PC、BIR-BIPC-F、TEP-BIP-A(以上、商品名、旭有機材工業(株)から入手できる)、1,4-ジヒドロキシナフタレン、1,5-ジヒドロキシナフタレン、1,6-ジヒドロキシナフタレン、1,7-ジヒドロキシナフタレン、2,3-ジヒドロキシナフタレン、2,6-ジヒドロキシナフタレン、2,7-ジヒドロキシナフタレン、2,4-ジヒドロキシキノリン、2,6-ジヒドロキシキノリン、2,3-ジヒドロキシキノキサリン、アントラセン-1,2,10-トリオール、アントラセン-1,8,9-トリオール、8-キノリノールなどが挙げられる。これらのフェノール性水酸基を有する化合物を含有することで、得られる感光性樹脂組成物は、露光前はアルカリ現像液にほとんど溶解せず、露光すると容易にアルカリ現像液に溶解するために、現像による膜減りが少なく、かつ短時間で現像が容易になる。そのため、感度が向上しやすくなる。
また、本発明で用いられる感光性樹脂組成物は、硬化膜の比誘電率向上、硬度向上、熱線膨張係数の低減などの目的で無機粒子を含んでもよい。好ましい具体例としては酸化珪素、酸化チタン、チタン酸バリウム、硫酸バリウム、酸化バリウム、酸化ジルコニウム、酸化ハフニウム、酸化タンタル、酸化タングステン、酸化イットリウム、アルミナ、タルクなどが挙げられる。特に硬化膜の比誘電率を向上させる目的においては、比誘電率(εr)が20以上である酸化チタン(εr=115)、酸化ジルコニウム(εr=30)、チタン酸バリウム(εr=400)又は酸化ハフニウム(εr=25)が特に好ましい例として挙げられるが、これらに限定されない。これら無機粒子の一次粒子径は100nm以下、より好ましくは60nm以下が好ましい。無機粒子の個々の粒子径は、走査型電子顕微鏡(日本電子(株)社製走査型電子顕微鏡、JSM-6301NF)にて測長した。本発明に用いられる無機粒子の一次粒子径は、走査型電子顕微鏡写真から無作為に選んだ100個の粒子の直径を測長し、その算術平均を求めることにより算出できる。
本発明で用いられる感光性樹脂組成物は、熱酸発生剤を含有してもよい。熱酸発生剤は、加熱により酸を発生し、熱架橋剤の架橋反応を促進する他、(a)アルカリ可溶性樹脂に未閉環のイミド環構造、オキサゾール環構造を有している場合はこれらの環化を促進し、硬化膜の機械特性をより向上させることができる。
本発明の硬化膜に用いられる感光性樹脂組成物は、(i)環状アミド、環状ウレアおよびそれらの誘導体からなる群より選択される1種以上の化合物を含有することが好ましい。すなわち、本発明の硬化膜は、(i)環状アミド、環状ウレアおよびそれらの誘導体からなる群より選択される1種以上の化合物を含有することが好ましい。硬化膜に(i)環状アミド、環状ウレアおよびそれらの誘導体からなる群より選択される1種以上の化合物を含有することで、該化合物(i)が酸性ガスのクエンチャーとして働き、発光輝度の低下や画素シュリンクを抑制し、有機EL装置として十分な長期信頼性を与えることが可能となるものと推定している。
(i)環状アミド、環状ウレアおよびそれらの誘導体からなる群より選択される1種以上の化合物は、加熱処理後に膜中に残存させやすくする観点から、沸点が210℃以上であることが好ましい。また塗布時のムラを抑制するという観点から、沸点は400℃以下であることが好ましい。常圧で沸点が測定できない場合は、沸点換算表を用いて常圧での沸点に換算することができる。
次に、本発明の感光性樹脂組成物の製造方法について説明する。例えば、前記(a)~(c)成分と、必要により、熱架橋剤、密着改良剤、界面活性剤、フェノール性水酸基を有する化合物、無機粒子、熱酸発生剤などを溶解させることにより、感光性樹脂組成物を得ることができる。溶解方法としては、撹拌や加熱が挙げられる。加熱する場合、加熱温度は感光性樹脂組成物の性能を損なわない範囲で設定することが好ましく、通常、室温~80℃である。また、各成分の溶解順序は特に限定されず、例えば、溶解性の低い化合物から順次溶解させる方法がある。また、界面活性剤や一部の密着改良剤など、撹拌溶解時に気泡を発生しやすい成分については、他の成分を溶解してから最後に添加することで、気泡の発生による他成分の溶解不良を防ぐことができる。
次に、本発明の感光性樹脂組成物を用いた硬化膜の製造方法について詳しく説明する。得られた硬化膜は薄膜トランジスタのゲート絶縁層または層間絶縁層として好適に用いることができる。
本発明の有機EL表示装置は、基板上に、駆動回路、平坦化層、第1電極、絶縁層、発光層および第2電極を有し、平坦化層および/または絶縁層が本発明の硬化膜からなる。アクティブマトリックス型の表示装置を例に挙げると、ガラスや樹脂フィルムなどの基板上に、TFTと、TFTの側方部に位置しTFTと接続された配線とを有し、その上に凹凸を覆うようにして平坦化層を有し、さらに平坦化層上に表示素子が設けられている。表示素子と配線とは、平坦化層に形成されたコンタクトホールを介して接続される。特に、近年有機EL表示装置のフレキシブル化が主流になっており、前述の駆動回路を有する基板が樹脂フィルムからなる有機EL表示装置であることが好ましい。本発明の感光性樹脂組成物または感光性シートを硬化した硬化膜をそのようなフレキシブルディスプレイの絶縁層、平坦化層として用いると、柔軟性に優れるため特に好ましく用いられる。本発明の感光性樹脂組成物または感光性シートを硬化した硬化膜との密着性を向上させる観点から、樹脂フィルムとしてはポリイミドが特に好ましい。
大日本スクリーン製造(株)製ラムダエースSTM-602を使用し、プリベーク後、現像後、キュア後の膜厚を、ポリイミドを対象に屈折率1.629として測定した。
ゼータ電位・粒子径・分子量測定装置(ゼータサイザーナノZSP;シスメックス(株)製)を用い、希釈溶媒としてPGMEAを用いて、顔料分散液を1.0×10-5~40体積%の濃度に希釈し、希釈溶媒の屈折率をPGMEAに、測定対象の屈折率を1.8に設定して、波長633nmのレーザー光を照射して顔料分散液中の顔料の数平均粒子径を測定した。
実施例および比較例で作製した感光性樹脂組成物(ワニス)を8インチシリコンウエハ上に回転塗布し、次いで、120℃のホットプレート(東京エレクトロン(株)製の塗布現像装置Act-8使用)で3分間ベークし、厚さ2.5μmのプリベーク膜を作製した。この膜を、i線ステッパー(NIKON NSR i9)を用いて0~1000mJ/cm2の露光量にて10mJ/cm2ステップで露光した。露光後、2.38質量%のテトラメチルアンモニウム(TMAH)水溶液(三菱ガス化学(株)製、ELM-D)で90秒間現像し、ついで純水でリンスして、10μmの孤立パターンを有する現像膜Aを得た。
実施例および比較例で作製した感光性樹脂組成物(ワニス)を、ITO基板上にスピンコーター(MS-A100;ミカサ(株)製)を用いて任意の回転数でスピンコーティングにより塗布した後、ホットプレート(SCW-636;大日本スクリーン製造(株)製)を用いて100℃で120秒間プリベークし、膜厚約2.0μmのプリベーク膜を作製した。作製したプリベーク膜を、両面アライメント片面露光装置(マスクアライナー PEM-6M;ユニオン光学(株)製)を用いて、感度測定用のグレースケールマスク(MDRM MODEL 4000-5-FS;Opto-Line International製)を介して、超高圧水銀灯のi線(波長365nm)、h線(波長405nm)及びg線(波長436nm)でパターニング露光した。露光後、フォトリソ用小型現像装置(AD-2000;滝沢産業(株)製)を用いて、2.38質量%TMAH水溶液で60秒間現像し、水で30秒間リンスして、10μmの孤立パターンを有する現像膜を作製した。
プリベーク膜に対する現像膜の膜厚の割合を残膜率とし(残膜率=(現像膜の膜厚)/(プリベーク膜の膜厚)×100)、80%以上を合格とした。
PIフィルム基板上に、ワニスをスピンコーター(MS-A100;ミカサ(株)製)を用いて任意の回転数でスピンコーティングにより塗布した後、ホットプレート(SCW-636;大日本スクリーン製造(株)製)を用いて120℃で120秒間プリベークし、膜厚約3.0μmのプリベーク膜を作製した。このプリベーク膜を高温イナートガスオーブン(INH-9CD-S;光洋サーモシステム(株)製)を用いて、酸素濃度20ppm以下で5℃/分で250℃まで昇温し、250℃で1時間加熱処理を行い、組成物の硬化膜を作製した。
図1に有機機EL表示装置の作製手順の概略図を示す。まず、38mmmm×46mmの無アルカリガラス基板9に、ITO透明導電膜10nmをスパッタ法により基板全面に形成し、第一電極10としてエッチングした。また同時に、第二電極を取り出すための補助電極11も形成した。得られた基板をセミコクリーン56(商品名、フルウチ化学(株)製)で10分間超音波洗浄してから、超純水で洗浄した。次にこの基板全面に、表5に示す感光性樹脂組成物をスピンコート法により塗布し、120℃のホットプレート上で2分間プリベークした。この膜にフォトマスクを介してUV露光した後、2.38質量%TMAH水溶液で現像し、不要な部分を溶解させ、純水でリンスした。得られた樹脂パターンを、高温イナートガスオーブン(INH-9CD-S;光洋サーモシステム(株)製)を用いて窒素雰囲気下250℃で1時間加熱処理した。このようにして、幅70μm、長さ260μmの開口部が幅方向にピッチ155μm、長さ方向にピッチ465μmで配置され、それぞれの開口部が第一電極を露出せしめる形状の絶縁層12を、基板有効エリアに限定して形成した。このようにして、1辺が16mmの四角形である基板有効エリアに絶縁層開口率25%の絶縁層を形成した。絶縁層の厚さは約1.0μmであった。
6FDA:4,4’-ヘキサフルオロイソプロピリデンジフタル酸二無水物
ABP:2-アミノ-4-tert-ブチルフェノール
BAHF: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
Bk-S0100CF:“IRGAPHOR”(登録商標) BLACK S0100CF(BASF製;一次粒子径40~80nmのベンゾフラノン系黒色顔料)
BIS-AT-AF:2,2-ビス(3-アミノ-4-メチルフェニル)ヘキサフルオロプロパン
CBDA:シクロブタンテトラカルボン酸二無水物
DAE:4,4’-ジアミノジフェニルエーテル
DFA:N、N-ジメチルホルムアミドジメチルアセタール
DPHA:“KAYARAD”(登録商標) DPHA(日本化薬(株)製;ジペンタエリスリトールヘキサアクリレート)
MA:無水マレイン酸
MAP:3-アミノフェノール;メタアミノフェノール
MBA:3-メトキシ-n-ブチルアセテート
NCI-831:“アデカアークルズ”(登録商標)NCI-831((株)ADEKA製;1-(9-エチル-6-ニトロ-9H-カルバゾール-3-イル)-1-[2-メチル-4-(1-メトキシプロパン-2-イルオキシ)フェニル]メタノン-1-(O-アセチル)オキシム)
NMP:N-メチル-2-ピロリドン
S-20000:“SOLSPERSE”(登録商標) 20000(Lubrizol製;ポリエーテル系分散剤)
SiDA:1,1,3,3-テトラメチル-1,3-ビス(3-アミノプロピル)ジシロキサン
TFM-DHB:2,2’-ビス(トリフルオロメチル)-5,5’-ジヒドロキシベンジジン
TMEG: 1,2-エチレンビス(アンヒドロトリメリテ-ト)。
BAHF18.3g(0.05モル)をアセトン100mL、プロピレンオキシド17.4g(0.3モル)に溶解させ、-15℃に冷却した。ここに3-ニトロベンゾイルクロリド20.4g(0.11モル)をアセトン100mLに溶解させた溶液を滴下した。滴下終了後、-15℃で4時間反応させ、その後室温に戻した。析出した白色固体をろ別し、50℃で真空乾燥した。
乾燥窒素気流下、TrisP-PA(商品名、本州化学工業(株)製)21.22g(0.05モル)と5-ナフトキノンジアジドスルホニル酸クロリド26.86g(0.10モル)、4-ナフトキノンジアジドスルホニル酸クロリド13.43g(0.05モル)を1,4-ジオキサン50gに溶解させ、室温にした。ここに、1,4-ジオキサン50gと混合したトリエチルアミン15.18gを、系内が35℃以上にならないように滴下した。滴下後30℃で2時間撹拌した。トリエチルアミン塩を濾過し、ろ液を水に投入した。その後、析出した沈殿をろ過で集めた。この沈殿を真空乾燥機で乾燥させ、下記式で表されるキノンジアジド化合物(b1-1)を得た。
乾燥窒素気流下、TrisP-HAP(商品名、本州化学工業(株)製)15.31g(0.05モル)と5-ナフトキノンジアジドスルホニル酸クロリド40.28g(0.15モル)を1,4-ジオキサン450gに溶解させ、室温にした。1,4-ジオキサン50gと混合したトリエチルアミン15.18gを用い、合成例2と同様にして下記式で表されるキノンジアジド化合物(b1-2)を得た。
乾燥窒素気流下、TekP-4HBPA(商品名、本州化学工業(株)製)28.83g(0.05モル)と5-ナフトキノンジアジドスルホニル酸クロリド13.43g(0.125モル)を1,4-ジオキサン450gに溶解させ、室温にした。1,4-ジオキサン50gと混合したトリエチルアミン20.24gを用い、合成例2と同様にして下記式で表されるキノンジアジド化合物(b1-3)を得た。
乾燥窒素気流下、合成例1で得られたヒドロキシル基含有ジアミン化合物(α)15.11g(0.025モル)、BAHF3.66g(0.01モル)、SiDA0.62g(0.0025モル)をNMP200gに溶解させた。ここにTMEG20.51g(0.05モル)をNMP50gとともに加えて、40℃で1時間撹拌した。その後、末端封止剤としてMAP2.73g(0.025モル)を加え、40℃で1時間撹拌した。その後、DFA11.9g(0.1モル)をNMP5gで希釈した溶液を10分かけて滴下し、滴下後、40℃で1時間撹拌を続けた。撹拌終了後、溶液を水2Lに投入して、固体の沈殿をろ過で集めた。さらに水2Lで3回洗浄を行い、集めたポリマー固体を50℃の真空乾燥機で72時間乾燥しポリアミド酸エステル樹脂(A)を得た。
BAHF3.66g(0.01モル)をBIS-AT-AF3.62g(0.01モル)、末端封止剤としてMAP2.73g(0.025モル)をABP4.13g(0.025モル)とした意外は実施例1と同様にしてポリアミド酸エステル樹脂(B)を得た。
乾燥窒素気流下、BAHF15.56g(0.0425モル)、SiDA0.62g(0.0025モル)をNMP 100gに溶解させた。ここにTMEG20.51g(0.05モル)をNMP10gとともに加えて、60℃で1時間反応させた。その後、末端封止剤としてMAP1.09g(0.01モル)を加え、さらに60℃で1時間撹拌を続けた。次いで180℃で4時間撹拌し、撹拌終了後、溶液を水2Lに投入して白色沈殿を得た。この沈殿を濾過で集めて、水で3回洗浄した後、50℃の真空乾燥機で72時間乾燥し既閉環ポリイミド樹脂(C)の粉末を得た。
BAHF15.56g(0.0425モル)を10.98g(0.03モル)、MAP1.09g(0.01モル)をABP1.65g(0.01モル)とし、ヒドロキシル基含有ジアミン化合物(α)6.05g(0.01モル)を加えた以外は実施例3と同様にして既閉環ポリイミド樹脂(D)を得た。
乾燥窒素気流下、BAHF11.9g(0.0325モル)、BIS-AT-AF5.43g(0.015モル)、SiDA0.62g(0.003モル)をNMP 100gに溶解させた。ここにTMEG15.39g(0.0375モル)をNMP10gとともに加えて、60℃で1時間反応させた。その後、末端封止剤としてMA2.45g(0.025モル)を加え、さらに60℃で1時間撹拌を続けた。次いで180℃で4時間撹拌し、撹拌終了後、溶液を水2Lに投入して白色沈殿を得た。この沈殿を濾過で集めて、水で3回洗浄した後、50℃の真空乾燥機で72時間乾燥し既閉環ポリイミド樹脂(E)を得た。
BAHF11.9g(0.0325モル)を8.24g(0.0225モル)、MA2.45g(0.025モル)を4.9g(0.05モル)、TMEG15.39g(0.0375モル)を10.26g(0.025モル)とし、BIS-AT-AF5.43g(0.015モル)の代わりにヒドロキシル基含有ジアミン化合物(α)15.11g(0.025モル)を加えた以外は実施例5と同様にして既閉環ポリイミド樹脂(F)を得た。
BAHF15.56g(0.0425モル)の代わりにBIS-AT-AF7.25g(0.02モル)とDAE4.0g(0.02モル)、MAP1.09g(0.01モル)を1.64g(0.015モル)とした以外は実施例3と同様にして既閉環ポリイミド樹脂(G)を得た。
乾燥窒素気流下、2,2’-ビス(トリフルオロメチル)-5,5’-ジヒドロキシベンジジン(TFM-DHB)13.21g(0.0375モル)、SiDA0.62g(0.0025モル)をNMP 200gに溶解させた。ここにTMEG20.51g(0.05モル)をNMP50gとともに加えて、60℃で1時間撹拌した。その後、末端封止剤としてMAP2.73g(0.025モル)を加え、さらに60℃で1時間撹拌を続けた。次いで180℃で4時間撹拌し、撹拌終了後、溶液を水2Lに投入して白色沈殿を得た。この沈殿を濾過で集めて、水で3回洗浄した後、50℃の真空乾燥機で72時間乾燥し既閉環ポリイミド樹脂(H)の粉末を得た。
BAHF15.56g(0.0425モル)を10.07g(0.0275モル)とし、DAE3.0g(0.015モル)を加えた以外は実施例3と同様にして既閉環ポリイミド樹脂(I)を得た。
樹脂(C)10g、キノンジアジド化合物(b1-3)3.0g、架橋剤VG-3101L(e-3)1.0gをGBL50gに加えてポジ型感光性樹脂組成物のワニスC2を得た。得られたワニスC2を用いて前記のように、感度評価、残膜率評価、折り曲げ性の評価、有機EL表示装置の長期信頼性評価を行った。評価結果を表2に示す。
樹脂(D)10g、キノンジアジド化合物(b1-3)3.0g、アルコキシメチル基含有熱架橋剤(e-1)1.0g、フェノール化合物BisP-AF(h-1)1.0gをGBL50gに加えてポジ型感光性樹脂組成物のワニスD2を得た。得られたワニスD2を用いて前記のように、感度評価、残膜率評価、折り曲げ性、有機EL表示装置の長期信頼性評価の評価を行った。評価結果を表2に示す。
樹脂(G)10g、キノンジアジド化合物(b1-1)3.0g、架橋剤VG-3101L(e-3)1.0gをGBL50gに加えてポジ型感光性樹脂組成物のワニスG2を得た。得られたワニスG2を用いて前記のように、感度評価、残膜率評価、折り曲げ性の評価、有機EL表示装置の長期信頼性評価を行った。評価結果を表2に示す。
樹脂(A)10g、キノンジアジド化合物(b1-1)3.0g、アルコキシメチル基含有熱架橋剤(e-1)1.0g、環状アミド化合物であるN-メチル-2-ピロリドン(NMP)0.5gをGBL 50gに加えてポジ型感光性樹脂組成物のワニスA2を得た。得られたワニスA2を用いて前記のように、感度評価、残膜率評価、折り曲げ性の評価、有機EL表示装置の長期信頼性評価を行った。評価結果を表2に示す。
乾燥窒素気流下、合成例1で得られたヒドロキシル基含有ジアミン化合物(α)15.11g(0.025モル)、BAHF3.66g(0.01モル)、SiDA0.62g(0.0025モル)をNMP200gに溶解させた。ここにTMEG10.26g(0.025モル)と6FDA11.11g(0.025モル)をNMP50gとともに加えて、40℃で1時間撹拌した。その後、末端封止剤としてMAP2.73g(0.025モル)を加え、40℃で1時間撹拌した。その後、DFA11.9g(0.1モル)をNMP5gで希釈した溶液を10分かけて滴下し、滴下後、40℃で1時間撹拌を続けた。撹拌終了後、溶液を水2Lに投入して、固体の沈殿をろ過で集めた。さらに水2Lで3回洗浄を行い、集めたポリマー固体を50℃の真空乾燥機で72時間乾燥しポリアミド酸エステル樹脂(J)を得た。
乾燥窒素気流下、BAHF10.07g(0.0275モル)、BIS-AT-AF7.25g(0.02モル)、SiDA0.62g(0.0025モル)をNMP200gに溶解させた。ここにTMEG14.36g(0.035モル)とCBDA2.94g(0.015モル)をNMP50gとともに加えて、40℃で1時間撹拌した。その後、DFA11.9g(0.1モル)をNMP5gで希釈した溶液を10分かけて滴下し、滴下後、40℃で1時間撹拌を続けた。末端封止剤は用いなかった。撹拌終了後、溶液を水2Lに投入して、固体の沈殿をろ過で集めた。さらに水2Lで3回洗浄を行い、集めたポリマー固体を50℃の真空乾燥機で72時間乾燥しポリアミド酸エステル樹脂(K)を得た。
乾燥窒素気流下、BAHF13.73g(0.0375モル)、BIS-AT-AF3.62g(0.01モル)、SiDA0.62g(0.0025モル)をNMP 100gに溶解させた。ここに6FDA22.21g(0.05モル)をNMP10gとともに加えて、60℃で1時間反応させた。次いで180℃で4時間撹拌した。末端封止剤は用いなかった。撹拌終了後、溶液を水2Lに投入して白色沈殿を得た。この沈殿を濾過で集めて、水で3回洗浄した後、50℃の真空乾燥機で72時間乾燥し既閉環ポリイミド樹脂(L)の粉末を得た。
乾燥窒素気流下、BAHF14.64g(0.04モル)、SiDA0.62g(0.0025モル)をNMP 100gに溶解させた。ここにTMEG8.21g(0.02モル)と6FDA13.33g(0.03モル)をNMP10gとともに加えて、60℃で1時間反応させた。その後、末端封止剤としてMAP1.64g(0.015モル)を加え、さらに60℃で1時間撹拌を続けた。次いで180℃で4時間撹拌し、撹拌終了後、溶液を水2Lに投入して白色沈殿を得た。この沈殿を濾過で集めて、水で3回洗浄した後、50℃の真空乾燥機で72時間乾燥し既閉環ポリイミド樹脂(M)の粉末を得た。
乾燥窒素気流下、合成例1で得られたヒドロキシル基含有ジアミン化合物(α)6.05g(0.01モル)、BAHF10.07g(0.0275モル)、SiDA0.62g(0.0025モル)をNMP 100gに溶解させた。ここにCBDA9.81g(0.05モル)をNMP10gとともに加えて、60℃で1時間反応させた。その後、末端封止剤としてMAP2.18g(0.02モル)を加え、さらに60℃で1時間撹拌を続けた。次いで180℃で4時間撹拌し、撹拌終了後、溶液を水2Lに投入して白色沈殿を得た。この沈殿を濾過で集めて、水で3回洗浄した後、50℃の真空乾燥機で72時間乾燥し既閉環ポリイミド樹脂(N)の粉末を得た。
乾燥窒素気流下、BAHF17.39g(0.0475モル)SiDA0.62g(0.0025モル)をNMP200gに溶解させた。ここにTMEG20.51g(0.05モル)をNMP50gとともに加えて、40℃で1時間撹拌した。その後、DFA11.9g(0.1モル)をNMP5gで希釈した溶液を10分かけて滴下し、滴下後、40℃で1時間撹拌を続けた。末端封止剤は用いなかった。撹拌終了後、溶液を水2Lに投入して、固体の沈殿をろ過で集めた。さらに水2Lで3回洗浄を行い、集めたポリマー固体を50℃の真空乾燥機で72時間乾燥しポリアミド酸エステル樹脂(O)を得た。
樹脂として、実施例3で得られた樹脂(C)の30質量%のMBA溶液を138.0g、分散剤として、S-20000を13.8g、溶剤として、MBAを685.4g、着色剤として、Bk-S0100CF82.8gを秤量して混合し、高速分散機(ホモディスパー 2.5型;プライミクス(株)製)を用いて20分攪拌し、予備分散液を得た。顔料分散用のセラミックビーズとして、0.30mmφのジルコニア粉砕ボール(YTZ;東ソー(株)製)が75%充填された遠心分離セパレータを具備する、ウルトラアペックスミル(UAM-015;寿工業(株)製)に、得られた予備分散液を供給し、ローター周速7.0m/sで3時間処理して、固形分濃度15質量%、着色剤/樹脂/分散剤=60/30/10(質量比)の顔料分散液(Bk-1)を得た。得られた顔料分散液中の顔料の数平均粒子径は100nmであった。
樹脂(C)の代わりに樹脂(M)を用いた以外は調製例1と同様にして顔料分散液(Bk-2)を得た。
黄色灯下、NCI-831を0.25g秤量し、MBAを10.0g添加し、攪拌して溶解させた。次に、実施例1で得られた樹脂(A)の30質量%のMBA溶液を3.5g、DPHAの80質量%のMBA溶液を1.5g添加して攪拌し、均一溶液として調合液を得た。次に、調製例1で得られた顔料分散液(Bk-1)を16.67g秤量し、ここに、上記で得られた調合液を添加して攪拌し、均一溶液とした。その後、得られた溶液を0.45μmφのフィルターでろ過し、ネガ型感光性樹脂組成物のワニスBAを得た。得られたワニスBAを用いて前記のように、感度評価、残膜率評価、折り曲げ性の評価、有機EL表示装置の長期信頼性評価を行った。組成を表3に、評価結果を表4に示す。
実施例14と同様に、感光性樹脂組成物のワニスBB~BNを表3に記載の組成にて調製した。得られた各組成物を用いて、実施例14と同様に、感度評価、残膜率評価、折り曲げ性の評価、有機EL表示装置の長期信頼性評価を行った。評価結果を表4に示す。
2:配線
3:TFT絶縁層
4:平坦化層
5:ITO(透明電極)
6:基板
7:コンタクトホール
8:絶縁層
9:ガラス基板
10:第一電極(非透明電極)
11:補助電極
12:絶縁層
13:有機EL層
14:第二電極(透明電極)
Claims (21)
- (a)アルカリ可溶性樹脂、(b)感光性化合物を含有し、
前記(a)アルカリ可溶性樹脂が、一般式(1)で表される構造を繰り返し単位として95~100モル%有し、前記(a)アルカリ可溶性樹脂におけるポリマー分子鎖の少なくとも一方の末端にモノアミンまたは酸無水物に由来する有機基を有する感光性樹脂組成物。
- 前記一般式(1)におけるX1およびX2が、エチレン基、プロピレン基、またはブチレン基である、請求項1に記載の感光性樹脂組成物。
- 前記(a)アルカリ可溶性樹脂が、モノアミンまたは酸無水物に由来する有機基を、一般式(1)で表される構造単位100モル%に対して10~100モル%有する、請求項1または2に記載の感光性樹脂組成物。
- 前記(b)感光性化合物が、(b1)光酸発生剤である、請求項1~4のいずれかに記載の感光性樹脂組成物。
- 前記(b)感光性化合物が、(b2)光重合開始剤であり、さらに(d)ラジカル重合性化合物を含有する、請求項1~4のいずれかに記載の感光性樹脂組成物。
- さらに(e)熱架橋剤を含有する、請求項1~6のいずれかに記載の感光性樹脂組成物。
- さらに(f)着色剤を含有する、請求項1~7のいずれかに記載の感光性樹脂組成物。
- 前記(f)着色剤が、(f3)黒色剤および/または(f4)黒色以外の着色剤である、請求項8に記載の感光性樹脂組成物。
- 前記(f)着色剤が、(f1)顔料または(f2)染料である、請求項8または9に記載の感光性樹脂組成物。
- 請求項1~10のいずれかに記載の感光性樹脂組成物からなる感光性シート。
- 請求項1~10のいずれかに記載の感光性樹脂組成物の硬化物からなる硬化膜。
- 請求項11に記載の感光性シートの硬化物からなる硬化膜。
- (i)環状アミド、環状ウレアおよびそれらの誘導体からなる群より選択される1種以上の化合物を含む請求項12または13に記載の硬化膜。
- 硬化膜中における前記(i)環状アミド、環状ウレアおよびそれらの誘導体からなる群より選択される1種以上の化合物の総含有量が0.005質量%以上5質量%以下である請求項10に記載の硬化膜。
- 請求項12~15のいずれかに記載の硬化膜を具備する素子。
- 駆動回路を有する基板上に、請求項12~15のいずれかに記載の硬化膜からなる平坦化層および/または第1電極上の絶縁層を具備する有機EL表示装置。
- 前記駆動回路を有する基板が樹脂フィルムからなる請求項17に記載の有機EL表示装置。
- 請求項12~15のいずれかに記載の硬化膜からなる再配線間の層間絶縁膜を具備する半導体電子部品。
- 請求項12~15のいずれかに記載の硬化膜からなる再配線間の層間絶縁膜を具備する半導体装置。
- 請求項1~11のいずれかに記載の感光性樹脂組成物を基板に塗布し、または請求項11に記載の感光性シートを基板にラミネートし、感光性樹脂膜を形成する工程、前記感光性樹脂膜を乾燥する工程、乾燥した感光性樹脂膜を露光する工程、露光した感光性樹脂膜を現像する工程および現像した感光性樹脂膜を加熱処理する工程を含む有機EL表示装置の製造方法。
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JP2020066651A (ja) * | 2018-10-22 | 2020-04-30 | 東レ株式会社 | 樹脂組成物、樹脂シート、硬化膜、硬化膜の製造方法、半導体装置および表示装置 |
JP2020154247A (ja) * | 2019-03-22 | 2020-09-24 | 太陽ホールディングス株式会社 | 感光性樹脂組成物、ドライフィルム、硬化物、及び、電子部品 |
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CN115678005A (zh) * | 2021-07-13 | 2023-02-03 | 上海邃铸科技有限公司 | 聚合物、树脂组合物、树脂膜以及半导体器件和发光器件 |
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JP7106863B2 (ja) | 2022-07-27 |
TW201821481A (zh) | 2018-06-16 |
KR20190020016A (ko) | 2019-02-27 |
JPWO2017217292A1 (ja) | 2019-04-04 |
TWI734795B (zh) | 2021-08-01 |
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