CN117693714A - Photosensitive composition, photosensitive element, and method for producing wiring board - Google Patents
Photosensitive composition, photosensitive element, and method for producing wiring board Download PDFInfo
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- CN117693714A CN117693714A CN202280049825.5A CN202280049825A CN117693714A CN 117693714 A CN117693714 A CN 117693714A CN 202280049825 A CN202280049825 A CN 202280049825A CN 117693714 A CN117693714 A CN 117693714A
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- photosensitive
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- photosensitive composition
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- 239000001099 ammonium carbonate Substances 0.000 description 1
- 235000011162 ammonium carbonates Nutrition 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000010009 beating Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000011889 copper foil Substances 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001723 curing Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000007607 die coating method Methods 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- UQGFMSUEHSUPRD-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound [Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 UQGFMSUEHSUPRD-UHFFFAOYSA-N 0.000 description 1
- 238000007772 electroless plating Methods 0.000 description 1
- 238000009713 electroplating Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000007756 gravure coating Methods 0.000 description 1
- 239000001046 green dye Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000012216 imaging agent Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229940107698 malachite green Drugs 0.000 description 1
- FDZZZRQASAIRJF-UHFFFAOYSA-M malachite green Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](C)C)C=C1 FDZZZRQASAIRJF-UHFFFAOYSA-M 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 238000011417 postcuring Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000007261 regionalization Effects 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000011182 sodium carbonates Nutrition 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- 229940048086 sodium pyrophosphate Drugs 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- RYCLIXPGLDDLTM-UHFFFAOYSA-J tetrapotassium;phosphonato phosphate Chemical compound [K+].[K+].[K+].[K+].[O-]P([O-])(=O)OP([O-])([O-])=O RYCLIXPGLDDLTM-UHFFFAOYSA-J 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 1
Classifications
-
- 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
-
- 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/02—Apparatus or processes for manufacturing printed circuits in which the conductive material is applied to the surface of the insulating support and is thereafter removed from such areas of the surface which are not intended for current conducting or shielding
- H05K3/06—Apparatus or processes for manufacturing printed circuits in which the conductive material is applied to the surface of the insulating support and is thereafter removed from such areas of the surface which are not intended for current conducting or shielding the conductive material being removed chemically or electrolytically, e.g. by photo-etch process
- H05K3/061—Etching masks
- H05K3/064—Photoresists
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Materials For Photolithography (AREA)
- Polymerisation Methods In General (AREA)
- Manufacturing Of Printed Circuit Boards (AREA)
- Manufacturing Of Printed Wiring (AREA)
- Laminated Bodies (AREA)
Abstract
A photosensitive composition comprising: a photopolymerizable compound; hexaarylbiimidazole compounds; and a compound represented by the following formula (1), wherein R 1 、R 2 And R is 3 Each independently represents an alkyl group having 5 or less carbon atoms, R 4 Represents a halogen atom, an alkyl group or an alkoxy group, and m and n each independently represent an integer of 0 or more.
Description
Cross Reference to Related Applications
The present application claims priority from PCT application PCT/CN2021/106686 filed on 7/16 of 2021, the entire contents of which are incorporated herein by reference.
Technical Field
The invention relates to a photosensitive composition, a photosensitive element and a method for manufacturing a wiring board.
Background
In wiring board production, a resist pattern is formed to obtain a desired wiring pattern. Photosensitive compositions are widely used for resist patterning. In recent years, MSAP (modified half addition method) has been attracting attention as a promising method for forming fine wiring patterns. This method requires a higher accuracy of the formed resist pattern than the conventional method in order to obtain a fine wiring pattern.
In the photosensitive composition, a photosensitizer is generally used in addition to the photopolymerizable compound and the photopolymerization initiator. In such a photosensitive composition, for example, a hexaarylbiimidazole compound is used as a photopolymerization initiator. For example, 9, 10-Dibutoxyanthracene (DBA) is a known photosensitizer (for example, see patent document 1).
CITATION LIST
Patent literature
Patent document 1: WO 2007/123062
Disclosure of Invention
Technical problem
According to the studies of the inventors, when the hexaarylbiimidazole compound in patent document 1 is used as a photopolymerization initiator, there is room for further study in selecting a photosensitizer. Specifically, the photosensitive composition is generally used in the form of a photosensitive element sandwiched between polymer films, and according to the investigation of the inventors, when DBA is contained in the photosensitive composition in addition to the hexaarylbisimidazole compound, DBA migrates into the polymer film, and a problem (migration) may occur in that a desired pattern shape cannot be formed when a resist pattern is formed. This problem occurs particularly when the polymer film is a polyethylene film.
An object of one aspect of the present invention is to provide a photosensitive composition capable of inhibiting migration of a photosensitizer to a polyethylene film.
Solution to the problem
The inventors found that migration of the photosensitizer to the polyethylene film can be suppressed by selecting a specific compound as the photosensitizer and using it together with the hexaarylbisimidazole compound, as compared with the case where DBA is used as the photosensitizer.
The invention comprises the following aspects:
[1] a photosensitive composition comprising: a photopolymerizable compound; hexaarylbiimidazole compounds; and a compound represented by the following formula (1):
wherein R is 1 、R 2 And R is 3 Each independently represents an alkyl group having 5 or less carbon atoms, R 4 Represents a halogen atom, an alkyl group or an alkoxy group, and m and n each independently represent an integer of 0 or more.
[2]According to [1]]The photosensitive composition, wherein R in formula (1) 1 、R 2 And R is 3 The alkyl groups represented have 2 or more carbon atoms.
[3] The photosensitive composition according to [1] or [2], wherein m and n in the formula (1) are 0.
[4] The photosensitive composition according to [1] or [2], wherein m in the formula (1) is 1 and n is 0.
[5] The photosensitive composition according to [1] or [2], wherein m in the formula (1) is 0 and n is 1.
[6] The photosensitive composition according to [1] or [2], wherein m in the formula (1) is 0 and n is 2.
[7] The photosensitive composition according to [1] or [2], wherein the compound represented by the formula (1) is a compound represented by the following formula (6):
wherein R is 1 And R is 2 Respectively with R in formula (1) 1 And R is 2 Identical, R 4 Represents a halogen atom.
[8] The photosensitive composition according to [7], wherein the halogen atom is a chlorine atom.
[9] A photosensitive element, comprising: a support body; and a photosensitive layer provided on the support, the photosensitive layer comprising the photosensitive composition of any one of [1] to [8 ].
[10] A method of manufacturing a wiring board, comprising: disposing a photosensitive layer comprising the photosensitive composition of any one of [1] to [8] on a substrate; photo-curing a portion of the photosensitive layer; removing the uncured portion of the photosensitive layer to form a resist pattern; and forming a wiring layer on a portion of the substrate where the resist pattern is not formed.
The beneficial effects of the invention are that
The present invention can provide a photosensitive composition capable of inhibiting migration of a photosensitive agent to a polyethylene film. Another aspect of the present invention can provide a photosensitive composition having excellent sensitivity (particularly sensitivity when a low-illuminance light source is used). Another aspect of the present invention may provide a photosensitive composition having excellent adhesion to a substrate.
Drawings
Fig. 1 is a schematic cross-sectional view of a photosensitive element according to an embodiment.
Fig. 2 is a schematic diagram of a wiring board manufacturing method according to an embodiment.
Detailed Description
Embodiments of the present invention will be described in detail below. The term "process" in the present specification means not only an independent process but also a process that successfully realizes the intended operation of the process and is not clearly distinguishable from other processes. The use of the term "to a numerical range refers to a range that includes the numerical values before" to "and after" to "as the minimum and maximum values of the range. The term "layer" refers to a structure formed on a partial surface of a certain object when viewed in plan view, in addition to a structure formed on the entire surface of the certain object when viewed in plan view. The term "(meth) acrylic" refers to at least one of "acrylic" and the corresponding "methacrylic". The same applies to other similar expressions such as (meth) acryl.
In this specification, with respect to the content of each component in the composition in this specification, when the composition contains a plurality of substances to constitute the component, the total content of all the substances in the composition is referred to unless otherwise specified. In the present specification, the term "solid component" refers to a nonvolatile component in the photosensitive composition, excluding volatile substances (e.g., water or solvents). More specifically, the term "solid component" refers to any component which is not a solvent and does not volatilize, but remains after drying the photosensitive composition described below, and includes substances which are liquid, syrup-like or waxy at room temperature (25 ℃).
< photosensitive composition >
One embodiment of the present invention is a photosensitive composition comprising a photopolymerizable compound, a hexaarylbiimidazole compound, and a compound represented by the following formula (1):
wherein R is 1 、R 2 And R is 3 Each independently represents an alkyl group having 5 or less carbon atoms, R 4 Represents a halogen atom, an alkyl group or an alkoxy group, and m and n each independently represent an integer of 0 or more.
The photosensitive composition contains one or more photopolymerizable compounds. The photopolymerizable compound may be a compound which is polymerized by light, and may be, for example, a compound having an ethylenically unsaturated bond or a compound having a (meth) acryloyl group.
From the viewpoint of further improving the alkali developability, resolution, and post-curing release property, the photopolymerizable compound may contain a bisphenol a (meth) acrylate compound. Examples of bisphenol a (meth) acrylate compounds include 2, 2-bis (4- ((meth) acryloxypolyethoxy) phenyl) propane (e.g., 2-bis (4- ((meth) acryloxypentaethoxy) phenyl) propane), 2-bis (4- ((meth) acryloxypolypropoxy) phenyl) propane, 2-bis (4- ((meth) acryloxypolybutoxy) phenyl) propane, and 2, 2-bis (4- ((meth) acryloxypolyethoxypropoxy) phenyl) propane. From the standpoint of further improving the solubility and peelability, the photopolymerizable compound may contain 2, 2-bis (4- ((meth) acryloxypolyethoxy) phenyl) propane (e.g., 2-bis (4- ((meth) acryloxypentaethoxy) phenyl) propane.
From the viewpoint of further improving the resolution of the resist pattern, the content of the bisphenol a (meth) acrylate compound may be 20 mass% or more, or 40 mass% or more, and 100 mass% or less, or 95 mass% or less, or 90 mass% or less with respect to the total content of the photopolymerizable compounds.
From the viewpoint of further suitably improving the resolution and flexibility, the photopolymerizable compound may contain an α, β -unsaturated ester compound obtained by reacting a polyol with an α, β -unsaturated carboxylic acid. Examples of the α, β -unsaturated ester compounds include polyalkylene glycol di (meth) acrylates such as polyethylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, and EO-modified polypropylene glycol, trimethylolpropane di (meth) acrylate, trimethylolpropane tri (meth) acrylate, EO-modified trimethylolpropane tri (meth) acrylate, PO-modified trimethylolpropane tri (meth) acrylate, EO-PO-modified trimethylolpropane tri (meth) acrylate, tetramethylolmethane tri (meth) acrylate, and tetramethylolmethane tetra (meth) acrylate.
From the viewpoint of improving flexibility, the content of the α, β -unsaturated ester compound may be 20 mass% or more, or 30 mass% or more with respect to the total content of the photopolymerizable compounds; from the viewpoint of further improving the resolution, it may be 70 mass% or less, or 60 mass% or less.
The photopolymerizable compound may include a phthalate compound, an alkyl (meth) acrylate, a nonylphenol polyethylene oxy acrylate, a photopolymerizable compound (oxetane compound or the like) having at least one cationically polymerizable cyclic ether group in the molecule, and the like. The photopolymerizable compound may include a phthalic acid-based compound from the viewpoint of further suitably improving resolution, adhesion, resist shape, and release characteristics after curing.
The phthalate compound may be, for example, a compound having a phthalic acid structure and a (meth) acryloyl group. Such compounds may be, for example, gamma-chloro-beta-hydroxypropyl-beta '- (meth) acryloyloxyethyl phthalate (also known as 3-chloro-2-hydroxypropyl-2- (meth) acryloyloxyethyl phthalate), beta-hydroxyethyl-beta' - (meth) acryloyloxyethyl phthalate, or beta-hydroxypropyl-beta '- (meth) acryloyloxyethyl phthalate, preferably gamma-chloro-beta-hydroxypropyl-beta' - (meth) acryloyloxyethyl phthalate.
When the photopolymerizable compound contains a phthalate compound, the content of the phthalate compound may be 1 mass% or more, 3 mass% or more, or 5 mass% or more and 30 mass% or less, 25 mass% or less, or 20 mass% or less with respect to the total content of the photopolymerizable compound from the viewpoint of further suitably improving the resolution, adhesion, resist shape, and post-cure peeling property of the photopolymerizable compound.
From the viewpoint of further improving sensitivity and resolution, the content of the photopolymerizable compound may be 3 mass% or more, 10 mass% or more, or 25 mass% or more with respect to the total content of solid components in the photosensitive composition; from the viewpoint of excellent film forming property, the content of the photopolymerizable compound may be 70 mass% or less, 60 mass% or less, or 50 mass% or less.
The hexaarylbiimidazole compound is a compound useful as a photopolymerization initiator. The hexaarylbisimidazole compound has a structure represented by the following formula (a):
wherein Aryl represents Aryl. The six aryl groups may be the same or different from each other.
Aryl groups may be, for example, substituted or unsubstituted phenyl groups. For example, a substituted phenyl group may be a group in which one or two or more hydrogen atoms in the phenyl group are substituted with a halogen atom, an alkyl group or an alkoxy group. The halogen atom may be, for example, a chlorine atom. For example, the number of carbon atoms of the alkyl group may be 1 or more, or may be 4 or less. The alkyl group may be, for example, methyl. The number of carbon atoms of the alkoxy group may be 1 or more, or may be 4 or less. The alkoxy group may be, for example, methoxy.
For example, the hexaarylbiimidazole compound may be 2,2 '-bis (2-chlorophenyl) -4,4',5 '-tetraphenyl-1, 2' -biimidazole, 2 '-bis (4-methoxyphenyl) -4,4',5 '-tetraphenyl-1, 2' -biimidazole, or the like, preferably 2,2 '-bis (2-chlorophenyl) -4,4',5 '-tetraphenyl-1, 2' -biimidazole.
From the viewpoint of further improving the sensitivity and the adhesion, the content of the hexaarylbiimidazole compound may be 0.1 mass% or more, 0.5 mass% or more, 1 mass% or more, and 20 mass% or less, 10 mass% or less, 5 mass% or less (relative to the total solid content of the photosensitive composition).
The compound represented by the above formula (1) is a compound capable of functioning as a photosensitizer. In the above formula (1), R 1 、R 2 And R is 3 The alkyl groups represented may be straight or branched. The number of carbon atoms of the alkyl group may be 1 or more, or 2 or more, and 4 or less, or 3 or less, or 2. When m is an integer of 2 or more, a plurality of R 3 May be the same or different from each other.
In formula (1), R 4 The halogen atom represented may be, for example, a chlorine atom or a bromine atom. R is R 4 The alkyl groups represented may be straight or branched. The number of carbon atoms of the alkyl group may be 1 or more, may be 5 or less, 4 or less, 3 or less, 2 or less, or may be 1 or 2. R is R 4 The alkoxy groups represented may be straight or branched. The number of carbon atoms of the alkoxy group may be 1 or more, or may be 5 or less. When n is an integer of 2 or more, a plurality of R 4 May be the same or different from each other. From the viewpoint of improving sensitivity of the photosensitive composition to both low-illuminance light sources and high-illuminance light sources, R 4 Preferably a halogen atom, more preferably a chlorine atom.
In formula (1), m may be an integer of 1 or more, or may be an integer of 3 or less, 2 or less, 1 or less; n may be an integer of 1 or more, or may be an integer of 3 or less, 2 or less.
In one embodiment, m and n may be 0. That is, in one embodiment, the compound represented by formula (1) may be a compound represented by the following formula (2):
wherein R is 1 And R is 2 Respectively with R in formula (1) 1 And R is 2 The same applies.
In one embodiment, m may be 1 and n may be 0. That is, in one embodiment, the compound represented by the formula (1) may be a compound represented by the following formula (3) or a compound represented by the following formula (4):
wherein R is 1 、R 2 And R is 3 Respectively with R in formula (1) 1 、R 2 And R is 3 The same applies.
In one embodiment, m may be 0 and n may be 1. That is, in one embodiment, the compound represented by the formula (1) may be a compound represented by the following formula (5) or a compound represented by the following formula (6):
wherein R is 1 、R 2 And R is 4 Respectively with R in formula (1) 1 、R 2 And R is 4 The same applies.
In one embodiment, m may be 0 and n may be 2. That is, in one embodiment, the compound represented by the formula (1) may be a compound represented by the following formula (7) or a compound represented by the following formula (8):
wherein R is 1 、R 2 And R is 4 Respectively with R in formula (1) 1 、R 2 And R is 4 The same applies.
From the viewpoint of further improving sensitivity, the content of the compound represented by the formula (1) may be, for example, 0.01 mass% or more, preferably 0.05 mass% or more, more preferably 0.1 mass% or more, even more preferably 0.3 mass% or more, relative to the total solid content of the photosensitive composition. From the viewpoint of further improving the accuracy of pattern formation, the content of the compound represented by formula (1) is, for example, 10 mass% or less, preferably 5 mass% or less, more preferably 3 mass% or less, still more preferably 2 mass% or less, and particularly preferably 1 mass% or less, relative to the total solid content of the photosensitive composition.
The photosensitive composition may further contain a resin (binder resin). The resin may be an alkali-soluble resin from the viewpoint of being able to be suitably developed with an alkali.
Examples of the resin include acrylic resins. For example, the acrylic resin may contain (meth) acrylic acid as a monomer unit, and may further contain (meth) acrylic acid ester. Examples of the (meth) acrylic acid ester include alkyl (meth) acrylate, cycloalkyl (meth) acrylate, and aryl (meth) acrylate.
From the viewpoint of further improving the solubility and the adhesive force, the acrylic resin may further contain styrene or a styrene derivative as a monomer unit. The styrene derivative may be, for example, vinyl toluene, alpha-methyl styrene, or the like. The acrylic resin preferably contains (meth) acrylic acid, (meth) acrylic acid ester and styrene or a styrene derivative as monomer units.
The content of (meth) acrylic acid may be, for example, 5 mass% or more, 10 mass% or more, or 20 mass% or more, and may also be 80 mass% or less, 60 mass% or less, or 50 mass% or less, with respect to the total amount of monomer units constituting the acrylic resin. The content of the (meth) acrylic acid ester may be, for example, 5 mass% or more, 10 mass% or more, or 20 mass% or more, or 80 mass% or less, 60 mass% or less, or 50 mass% or less with respect to the total amount of monomer units constituting the acrylic resin. The content of styrene and a styrene derivative may be, for example, 5 mass% or more, 10 mass% or more, or 20 mass% or more, and may also be 65 mass% or less, 55 mass% or less, or 50 mass% or less, with respect to the total amount of monomer units constituting the acrylic resin.
From the viewpoint of favorable developability, the acid value of the resin may be 100mgKOH/g or more, 120mgKOH/g or more, 140mgKOH/g or more, 150mgKOH/g or more; from the viewpoint of improving the adhesion (developer resistance) of the cured product of the photosensitive composition, the acid value of the resin may be 250mgKOH/g or less, 240mgKOH/g or less, 230mgKOH/g or less. The acid value of the resin may be adjusted by the content of the monomer units constituting the resin (for example, the content of (meth) acrylic acid).
The weight average molecular weight (Mw) of the resin may be 10000 or more, 20000 or more, or 25000 or more from the viewpoint of excellent adhesion (developer resistance) of the cured product of the photosensitive composition, and 100000 or less, 80000 or less, or 60000 or less from the viewpoint of suitability for development. The dispersity (Mw/Mn) of the resin may be, for example, 1.0 or more, or 1.5 or more, and may be 3.0 or less, or 2.5 or less from the viewpoint of further improving the adhesion and resolution.
The weight average molecular weight and dispersity can be measured by methods such as Gel Permeation Chromatography (GPC) and drawing a calibration curve using standard polystyrene. More specifically, the measurement may be performed under the conditions described in the examples section. When a compound having a low molecular weight is measured, if it is difficult to measure its weight average molecular weight by the above method, the molecular weight of the compound may be measured by other methods and then the average value is calculated to determine the weight average molecular weight of the compound.
From the viewpoint of excellent film forming property, the resin content may be 20 mass% or more, 30 mass% or more, or 40 mass% or more with respect to the total solid content of the photosensitive composition; from the viewpoint of further excellent sensitivity and resolution, the resin content may be 90 mass% or less, 80 mass% or less, or 65 mass% or less.
From the viewpoint of excellent film forming property, the content of the resin may be 30 parts by mass or more, 35 parts by mass or more, or 40 parts by mass or more with respect to 100 parts by mass of the total amount of the resin and the photopolymerizable compound; from the viewpoint of further improving sensitivity and resolution, the content of the resin may be 70 parts by mass or less, 65 parts by mass or less, or 60 parts by mass or less.
The photosensitive composition may further contain one or more additional components in addition to the above components. Examples of such additional ingredients include hydrogen donors (such as bis [4- (dimethylamino) phenyl ] methane, bis [4- (diethylamino) phenyl ] methane, leuco crystal violet and N-phenylglycine), dyes (such as malachite green), tribromophenyl sulfone, photochromic agents, agents for preventing thermochromic phenomena, plasticizers (such as p-toluenesulfonamide), pigments, fillers, defoamers, flame retardants, stabilizers, adhesion promoters, leveling agents, release promoters, antioxidants, fragrances, imaging agents and thermal crosslinking agents. The content of the additional component may be 0.005% by mass or more, or 0.01% by mass or more, or 20% by mass or less with respect to the total solid content of the photosensitive composition.
From the viewpoint of controlling the viscosity, the photosensitive composition may further contain one or more organic solvents. Examples of the organic solvent include methanol, ethanol, acetone, methyl ethyl ketone, methyl cellosolve, ethyl cellosolve, toluene, N-dimethylformamide, and propylene glycol monomethyl ether. The content of the organic solvent may be 40% or more, or 70% or less relative to the total content of the photosensitive composition.
The photosensitive composition can be suitably used for resist patterning, and is particularly suitable for use in a method for producing a wiring board described below.
< photosensitive element >
Fig. 1 is a schematic cross-sectional view of a photosensitive element according to an embodiment. As shown in fig. 1, the photosensitive element 1 includes a support 2, a photosensitive layer 3 provided on the support 2, and a protective layer 4 provided on the opposite side of the photosensitive layer 3 from the support 2.
The support 2 and the protective layer 4 may each be composed of a polymer film having heat resistance and solvent resistance; for example, it may be composed of a polyester film (such as a polyethylene terephthalate film) or a polyolefin film (such as a polyethylene film or a polypropylene film). The support 2 and the protective layer 4 may be hydrocarbon polymer films other than polyolefin. The density of the hydrocarbon polymer film including polyolefin may be low, for example, the density may be 1.014g/cm or less. The support 2 and the protective layer 4 may each be a stretched film obtained by stretching a low-density hydrocarbon polymer film. The kind of the polymer film constituting the protective layer 4 may be the same as or different from the kind of the polymer film constituting the support 2.
These polymer films are commercially available, for example, polyethylene terephthalate films of the PS product series (e.g., PS-25) produced by Teijin Limited, polyethylene films of NF-15 produced by Tamapoly Co., ltd., oji Paper Co., ltd., polypropylene films (e.g., alpha MA-410 and E-200C) produced by Ltd., and polypropylene films produced by Shin-Etsu Film Co., ltd.
The thickness of the support 2 may be 1 μm or more, or 5 μm or more from the viewpoint of suppressing possible damage to the support 2 when the support 2 is peeled off from the photosensitive layer 3; the thickness of the support 2 may be 100 μm or less, or 50 μm or less, or 30 μm or less from the viewpoint of proper exposure through the support 2.
The thickness of the protective layer 4 may be 1 μm or more, 5 μm or more, or 15 μm or more from the viewpoint of suppressing damage that may be caused to the protective layer 4 when the protective layer 4 is peeled off to laminate the photosensitive layer 3 and the support 2 with the substrate; from the viewpoint of improving productivity, it may be 100 μm or less, 50 μm or less, or 30 μm or less.
The photosensitive layer 3 is composed of the photosensitive composition. The thickness of the photosensitive layer 3 after drying (or after volatilizing the organic solvent when the photosensitive composition contains the organic solvent) may be 1 μm or more, or 5 μm or more from the viewpoint of ease of application and improvement of productivity; from the viewpoint of further improving the adhesion and resolution, it may also be 100 μm or less, or 50 μm or less, or 40 μm or less.
For example, the photosensitive element 1 can be obtained as follows. First, the photosensitive layer 3 is formed on the support 2. The photosensitive layer 3 may be formed as follows: for example, a photosensitive composition containing an organic solvent is coated to form a coating layer, and the formed coating layer is dried. Subsequently, a protective layer 4 is formed on the side of the photosensitive layer 3 opposite to the support 2.
The coating layer may be formed using, for example, a known method such as roll coating, unfilled wheel coating, gravure coating, air knife coating, die coating, or bar coating. The drying of the coating layer is performed, for example, in such a manner that the amount of the organic solvent remaining in the photosensitive layer 3 becomes 2 mass% or less. More specifically, for example, drying is carried out at a temperature of 70℃to 150℃for about 5 minutes to 30 minutes.
In another embodiment, the photosensitive element may not include a protective layer, and may further include additional layers such as a buffer layer, an adhesive layer, a light absorbing layer, and a gas barrier layer.
For example, the photosensitive element 1 may be a photosensitive element sheet or a photosensitive element roll, that is, a photosensitive element roll wound around a core. When the photosensitive element 1 is such a photosensitive element roll, the support 2 is preferably located outside. The winding core is made of, for example, polyethylene, polypropylene, polystyrene, polyvinyl chloride or acrylonitrile-butadiene-styrene copolymer. From the viewpoint of protecting the end face, one end face spacer may be provided on the end face of the photosensitive element roll, and from the viewpoint of avoiding edge fusion, a moisture-proof end face spacer may be provided. For example, the photosensitive element 1 may be covered with a black sheet having low moisture permeability.
The photosensitive element 1 can be suitably used for resist patterning, and is particularly suitable for use in a wiring board manufacturing method described below. Since the photosensitive element 1 can suppress permeation of the photosensitive agent into the polyethylene film as compared with the conventional photosensitive element, at least one of the support 2 and the protective layer 4 may be formed of the polyethylene film or may be formed of a hydrocarbon polymer film having a low density or a stretched film thereof.
< method for producing Wiring Board >
Fig. 2 is a schematic diagram showing a method of manufacturing a wiring board (also referred to as a printed wiring board) according to an embodiment. In this method, as shown in fig. 2 (a), a substrate (for example, a substrate on which a circuit is to be formed) is prepared, wherein the substrate has an insulating layer 11 and a conductor layer 12 formed on the insulating layer 11. The conductor layer 12 may be, for example, a metallic copper layer.
Subsequently, as shown in fig. 2 (b), a photosensitive layer 13 is formed on the substrate (conductor layer 12). In this step, the photosensitive composition or the photosensitive element 1 is used to form a photosensitive layer 13 composed of the photosensitive composition on a substrate (conductor layer 12). For example, the photosensitive layer 13 is formed by coating a photosensitive composition on a substrate and drying the photosensitive composition. Alternatively, the protective layer 4 is removed from the photosensitive element 1, and then the photosensitive layer 3 of the photosensitive element 1 is heated to be thermally bonded to the substrate, thereby forming the photosensitive layer 13. In the thermocompression bonding process, at least one of the photosensitive layer 3 and the substrate may be heated at a temperature of, for example, 70 ℃ to 130 ℃. The pressure applied during thermocompression bonding may be, for example, 0.1MPa to 1.0MPa.
Subsequently, as shown in fig. 2 (c), a mask 14 is placed on the photosensitive layer 13, and active rays 15 are applied thereto. Thus, other areas except for the area where the mask 14 is placed are exposed to light, thereby photo-curing the photosensitive layer 13. The light source of the active radiation 15 may be an ultraviolet light source or a visible light source, such as a carbon arc lamp, a mercury vapor arc lamp, a high-pressure mercury lamp, a xenon lamp, a gas laser (e.g., an argon laser), a solid-state laser (e.g., a YAG laser), or a semiconductor laser.
In another embodiment, a direct image exposure method such as an LDI exposure method or a DLP exposure method may be used instead of the mask 14. In this case, the active radiation 15 may be applied in a desired pattern such that only a portion of the photosensitive layer 13 is exposed to light.
Subsequently, as shown in fig. 2 (d), the region (uncured portion) other than the photo-cured portion formed by exposure is removed from the substrate by development, thereby forming a resist pattern 16 composed of the photo-cured portion (cured product of the photosensitive layer). The developing method may be wet developing or dry developing, for example, wet developing is preferable.
Wet development is performed by using a developer which can be applied to the photosensitive composition, and by dipping, using a paddle, spraying, brushing, beating, wiping, dipping, shaking, or the like. The developer is appropriately selected according to the components of the photosensitive composition, and may be an alkaline developer or an organic solvent developer.
The alkaline developer may be an aqueous solution containing a base such as: alkali metal hydroxides such as lithium, sodium or potassium hydroxide; alkali metal carbonates, such as lithium, sodium, potassium or ammonium carbonates or bicarbonates; alkali metal phosphates such as potassium dihydrogen phosphate or sodium dihydrogen phosphate; alkali metal pyrophosphates, such as sodium pyrophosphate or potassium pyrophosphate; borax; sodium metasilicate; tetramethyl ammonium hydroxide; ethanolamine; ethylenediamine; diethylenetriamine; 2-amino-2-hydroxymethyl-1, 3-propanediol; 1, 3-diamino-2-propanol; or morpholine.
For example, the alkaline developer may be a sodium carbonate aqueous solution of 0.1 to 5 mass%, a potassium carbonate aqueous solution of 0.1 to 5 mass%, a sodium hydroxide aqueous solution of 0.1 to 5 mass%, or a sodium tetraborate aqueous solution of 0.1 to 5 mass%. For example, the pH of the alkaline developer is 9 to 11.
For example, the alkaline developer may further contain a surfactant, an antifoaming agent, and/or an organic solvent. Examples of the organic solvent include acetone, ethyl acetate, alkoxyethanol having a C1 to C4 alkoxy group, ethanol, isopropanol, butanol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, and diethylene glycol monobutyl ether. The content of the organic solvent may be 2 to 90 mass% of the total amount of the alkaline developer.
The organic solvent developer may contain an organic solvent such as 1, 1-trichloroethane, N-methylpyrrolidone, N-dimethylformamide, cyclohexanone, methyl isobutyl ketone or gamma-butyrolactone. The organic solvent developer may further contain 1 to 20% by mass of water.
In this step, the product after removal of the unexposed portion may be heated at a temperature of 60℃to 250℃or, if necessary, 0.2J/cm 2 To 10J/cm 2 Further exposure to further cure the resist pattern 16.
Subsequently, as shown in fig. 2 (e), a plating treatment or the like is performed on a portion of the conductor layer 12 where the resist pattern 16 is not formed, thereby forming the wiring layer 17 at the portion. The kind of material constituting the wiring layer 17 may be the same as or different from that of the conductor layer 12. For example, the wiring layer 17 may be a metallic copper layer. The plating treatment may be one or both of an electrolytic plating treatment and an electroless plating treatment.
Subsequently, as shown in fig. 2 (f), the resist pattern 16 is removed, and a portion of the conductor layer 12 corresponding to the position of the resist pattern 16 is removed. Thus, a wiring board 18 composed of the substrate and the wiring layer 17 formed on the substrate is obtained.
The resist pattern 16 may be removed by, for example, using an aqueous solution of strong alkali and developing by dipping or spraying. For example, the aqueous alkali solution may be 1 to 10% by mass of an aqueous sodium hydroxide solution or 1 to 10% by mass of an aqueous potassium hydroxide solution.
The conductor layer 12 may be removed by an etching process. The etching liquid may be appropriately selected according to the type of the conductor layer 12, and may be, for example, a copper chloride solution, an iron chloride solution, an alkaline etching liquid, or a hydrogen peroxide etching liquid.
Examples
The present invention will be described in further detail by examples. These examples are in no way limiting to the scope of the invention.
[ Compound (1-1): synthesis of 9, 10-dipropyloxyanthracene ]
9, 10-anthraquinone (3.00 g,14.42 mmol), zn (9.43 g,144.23 mmol), K 2 CO 3 (19.93 g,144.23 mmol) and THF (60.0 mL) were placed in a 100mL container equipped with a stirrer and a nitrogen inlet tubeA reflux condenser, a dropping funnel and a thermometer. Propionic anhydride (17.5 mL,144.23 mmol) was added and stirred for 5 hours.
After the reaction is completed, zn and K are removed by filtration 2 CO 3 0.1M HCl was added, followed by dichloroethane (30 mL) and the mixture was stirred and the organic layer was collected. After washing the collected organic layer with water and brine, the organic layer was collected again and anhydrous MgSO was added 4 。
Subsequently, the anhydrous MgSO was removed by filtration 4 After drying under reduced pressure, the remaining solid was washed three times with hexane (30 mL) and diethyl ether (30 mL) each to obtain a compound (1-1) represented by the following formula (1-1): 9, 10-dipropyloxyanthracene.
[ Compound (1-2): synthesis of 9, 10-diacetoxy-anthracene
Compound (1-2) represented by the following formula (1-2) was synthesized by the same method as compound (1-1) except that propionic anhydride was changed to acetic anhydride: 9, 10-diacetoxy-anthracene.
[ Compound (1-3): synthesis of 2-bromo-9, 10-dipropyloxyanthracene
Compound (1-3) represented by the following formula (1-3) was synthesized by the same method as compound (1-1) except that 9, 10-anthraquinone was changed to 2-bromo-9, 10-anthraquinone: 2-bromo-9, 10-dipropyloxyanthracene.
[ Compound (1-4): synthesis of 2, 3-dimethyl-9, 10-dipropyloxyanthracene
Compound (1-4) represented by the following formula (1-4) was synthesized by the same method as compound (1-1) except that 9, 10-anthraquinone was changed to 2, 3-dimethyl-9, 10-anthraquinone: 2, 3-dimethyl-9, 10-dipropyloxyanthracene.
[ Compound (1-5): synthesis of 2-ethyl-9, 10-dipropyloxyanthracene
Compound (1-5) represented by the following formula (1-5) was synthesized by the same method as compound (1-1) except that 9, 10-anthraquinone was changed to 2-ethyl-9, 10-anthraquinone: 2-ethyl-9, 10-dipropyloxyanthracene.
[ Compound (1-6): 2,9,10 Synthesis of tripropionylxanthene
Compound (1-6) represented by the following formula (1-6) was synthesized by the same method as compound (1-1) except that 9, 10-anthraquinone was changed to 2-hydroxy-9, 10-anthraquinone: 2,9,10-Tripropionyloxy-anthracene.
[ Compound (1-7): synthesis of 2-chloro-9, 10-dipropyloxyanthracene
Compound (1-7) represented by the following formula (1-7) was synthesized by the same method as compound (1-1) except that 9, 10-anthraquinone was changed to 2-chloro-9, 10-anthraquinone: 2-chloro-9, 10-dipropyloxyanthracene.
UVS-581 (trade name, manufactured by Kawasaki Kasei Chemicals Ltd.) was used as the compound (1-8): 9, 10-Dioctanoyloxy anthracene (a compound represented by the following formula (1-8)).
UVS-1331 (trade name, manufactured by Kawasaki Kasei Chemicals Ltd.) was used as the compound (1-9): 9, 10-dibutoxyanthracene (DBA, a compound represented by the following formula (1-9)).
[ Synthesis of acrylic resin ]
Into a 1000mL three-necked flask equipped with a stirrer, a nitrogen inlet pipe, a reflux condenser, a dropping funnel and a thermometer were charged 96g of propylene glycol monomethyl ether (MFG) and 64g of toluene, and the temperature was raised to 80℃under a nitrogen atmosphere. To the flask, a mixture of 36g of methacrylic acid, 48g of styrene, 36g of benzyl methacrylate (mass ratio: 30/40/30) and 9g of Azobisisobutyronitrile (AIBN) was added dropwise over 3 hours, a mixture of 6g of MFG, 4g of toluene and 0.20g of AIBN was added dropwise over 2 hours, and then 6g of MFG and 4g of toluene were added dropwise to conduct a reaction. The reaction solution was heated to 95 ℃, stirred for 1.5 hours, and then cooled to room temperature to obtain an alkali-soluble acrylic resin solution. The nonvolatile content (solid content) of the solution was 40 mass%.
[ preparation of photosensitive composition ]
Example 1
A mixture of 25 parts by mass of 2, 2-bis (4- (methacryloxypentaethoxy) phenyl) propane (FA-321M (trade name), produced by Showa Denko Materials co., ltd.), 10 parts by mass of polyalkylene glycol di (meth) acrylate (FA-023M (trade name), produced by Showa Denko Materials co., ltd.) and 5 parts by mass of 2-hydroxy-3-chloropropyl-2-methacryloxyethyl phthalate (FA-MECH (trade name), produced by Showa Denko Materials co., ltd.), 3.7 parts by mass of 2,2 '-bis (2-chlorophenyl) -4,4',5 '-tetraphenyl-1, 2' -bisimidazole (produced by Hampford, also referred to as "photopolymerization initiator (a-1)"), 0.7 parts by mass of compound (1-1) as a photosensitizer, 60 parts by mass of a soluble acrylic resin (binder resin) synthesized by the above procedure, 0.5 parts by mass of crystal as a hydrogen donor (ltd.), and 3.7 parts by weight of a leuco dye (ltd.) was produced by 35, produced by ltd.) as a photopolymerization initiator, whereby green dye (ltd.35.84.tdwas obtained.
(examples 2 to 7 and comparative examples 1 and 2)
A photosensitive composition was obtained in the same manner as in example 1 except that any one of the compounds (1-2) to (1-9) shown in table 1 was used as a photosensitive agent instead of the compound (1-1).
Comparative example 3
A photosensitive composition was obtained in the same manner as in example 1 except that 2-hydroxy-2-methyl-1-phenyl-1-propanone (also referred to as "photopolymerization initiator (a-2)") was used instead of the photopolymerization initiator (a-1) as a photopolymerization initiator, and that compound (1-2) was used instead of compound (1-1) as a photosensitizer.
[ preparation of photosensitive element ]
The photosensitive composition was coated on a polyethylene terephthalate (PET) film (manufactured by Teijin Film Solutions co., ltd., under the trade name "G2J") (support) having a thickness of 16 μm, and then dried in a hot air convection dryer at 75 ℃ and 125 ℃ in this order, to form a photosensitive layer having a thickness of 25 μm. A polyethylene film (manufactured by tamopoy co., ltd., product name "NF-15") (protective layer) was adhered to the photosensitive layer to obtain a photosensitive element in which a support, photosensitive layer, and protective layer were laminated in this order.
[ evaluation of migration of photosensitizer to polyethylene film ]
The photosensitive element obtained above was packaged with a black sheet, left in a yellow light environment for 24 hours, and then the polyethylene film was peeled off from the photosensitive element. For the peeled polyethylene film, absorbance Abs (sample) at 405nm wavelength was measured using an ultraviolet-visible spectrophotometer (manufactured by Shimadzu Corporation (UV-1800)). Further, in the same manner as described above, absorbance Abs (see) at 405nm was measured for the same polyethylene film (new) used in the production of the photosensitive element. Based on the measured absorbance, the presence or absence of migration was evaluated according to the following criteria:
no migration: abs (sample) -Abs (reference) <0.01
There is a migration: abs (sample) -Abs (reference) was 0.01 or more.
[ preparation of laminate ]
Copper clad laminates (trade name "MCL-E-67", manufactured by Showa Denko Materials co., ltd.) in which copper foil (thickness: 35 μm) was laminated on both sides of a glass fiber-reinforced epoxy resin layer were washed with water, acid-washed (pickled), washed with water and blow-dried with air. The copper clad laminate was then heated to 80 ℃ and the photosensitive element was laminated to the copper surface of the copper clad laminate. While removing the protective layer, lamination was performed at a roll speed of 1.0m/min under a substrate pressure of 0.4MPa using a heat roll at 110 ℃. Thus, a laminate in which the copper-clad laminate, the photosensitive layer, and the support were laminated in this order was obtained.
[ sensitivity evaluation ]
(evaluation Using Low-illuminance light Source)
A41-stage stepwise exposure meter (manufactured by Showa Denko Materials Co., ltd.) was placed on the support of the resulting laminate, and an exposure wavelength of 405nm was set at 100mJ/cm using a direct drawing exposure machine (manufactured by Via Mechanics Co., ltd. (DE-1 UH)), and the laminate was exposed to light at a wavelength of light of one hundred thousand meters per minute 2 Exposure is performed.
Next, the photosensitive layer was developed with a 1 mass% aqueous sodium carbonate solution at 30 ℃, and the development time at which the residual film became zero was measured. The development treatment was performed for a time 2 times the measured development time, and then the number of steps (ST steps) of the step exposure meter remaining on the substrate was evaluated. The greater the ST order, the higher the sensitivity. The results are shown in Table 1. Table 1 shows the relative values at an ST level of 1.0 for comparative example 2.
(evaluation Using high illuminance light Source)
Except that a direct drawing exposure machine (produced by Orbotech (Fine 8), exposure wavelength: 405 nm) was used as an exposure machine at 40100mJ/cm 2 The method of evaluating sensitivity is the same as that of using a low-illuminance light source except that exposure is performed.
[ evaluation of adhesion ]
A direct drawing exposure machine (manufactured by Via Mechanics co., ltd. (DE-1 UH), exposure wavelength: 405 nm) was used to draw a pattern on the laminated support with an exposure amount corresponding to ST order = 16 orders. After the development treatment, in the resist pattern in which the blank portion (unexposed portion) is completely removed and the line portion (exposed portion) is formed without meandering or defects, the dimension n (μm) of the line portion in the independent pattern in which the line portion (μm)/blank portion (μm) =n (μm)/400 (μm) is the smallest is measured. The smaller the size, the stronger the adhesion. The results are shown in Table 1.
[ absorbance of photosensitive element ]
The polyethylene film was peeled off from the obtained photosensitive element, and absorbance at 405nm was measured using an ultraviolet-visible spectrophotometer (produced by Shimadzu Corporation (UV-1800)). The results are shown in Table 1.
TABLE 1
As can be seen from table 1, in the case of using a hexaarylbiimidazole compound as a photopolymerization initiator, migration to a polyethylene film occurs when DBA or the like is used as a photosensitizer (comparative examples 1 and 2), whereas migration to a polyethylene film is suppressed when a compound represented by formula (1) is used as a photosensitizer (examples 1 to 7). On the other hand, when a compound other than the hexaarylbiimidazole compound is used as the photopolymerization initiator and the compound represented by the formula (1) is used as the photosensitizer (comparative example 3), although migration to the polyethylene film is suppressed, the sensitivity (particularly, the sensitivity when a low-illuminance light source is used) is lower than that when the hexaarylbiimidazole compound is used as the photopolymerization initiator and the compound represented by the formula (1) is used as the photosensitizer (examples 1 to 7). In addition, the photosensitive compositions (examples 1 to 7) containing the combination of the hexaarylbiimidazole compound and the compound represented by formula (1) also have good adhesion to the substrate.
List of reference numerals
1: a photosensitive element; 2: a support body; 3. 13: a photosensitive layer; 4: a protective layer; 16: a resist pattern; 17: a wiring layer; 18: and a wiring board.
Claims (10)
1. A photosensitive composition comprising:
a photopolymerizable compound;
hexaarylbiimidazole compounds; and
a compound represented by the following formula (1):
wherein R is 1 、R 2 And R is 3 Each independently represents an alkyl group having 5 or less carbon atoms, R 4 Represents a halogen atom, an alkyl group or an alkoxy group, and m and n each independently represent an integer of 0 or more.
2. The photosensitive composition according to claim 1, wherein R in formula (1) 1 、R 2 And R is 3 The alkyl groups represented have 2 or more carbon atoms.
3. The photosensitive composition according to claim 1 or 2, wherein m and n in formula (1) are 0.
4. The photosensitive composition according to claim 1 or 2, wherein m in formula (1) is 1 and n is 0.
5. The photosensitive composition according to claim 1 or 2, wherein m in formula (1) is 0 and n is 1.
6. The photosensitive composition according to claim 1 or 2, wherein m in formula (1) is 0 and n is 2.
7. The photosensitive composition according to claim 1 or 2, wherein the compound represented by formula (1) is a compound represented by the following formula (6):
wherein R is 1 And R is 2 Respectively with R in formula (1) 1 And R is 2 Identical, R 4 Represents a halogen atom.
8. The photosensitive composition according to claim 7, wherein the halogen atom is a chlorine atom.
9. A photosensitive element, comprising:
a support body; and
a photosensitive layer disposed on the support,
the photosensitive layer contains the photosensitive composition according to claim 1 or 2.
10. A method of manufacturing a wiring board, comprising:
disposing a photosensitive layer comprising the photosensitive composition of claim 1 or 2 on a substrate;
photo-curing a portion of the photosensitive layer;
removing the uncured portion of the photosensitive layer to form a resist pattern; and
a wiring layer is formed on a portion of the substrate where the resist pattern is not formed.
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| CNPCT/CN2021/106686 | 2021-07-16 | ||
| PCT/CN2021/106686 WO2023283915A1 (en) | 2021-07-16 | 2021-07-16 | Photosensitive composition, photosensitive element, and method of producing wiring board |
| PCT/CN2022/104595 WO2023284643A1 (en) | 2021-07-16 | 2022-07-08 | Photosensitive composition, photosensitive element, and method of producing wiring board |
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| CN117693714A true CN117693714A (en) | 2024-03-12 |
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| JP (1) | JP2024526665A (en) |
| KR (1) | KR20240035832A (en) |
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| JP5594510B2 (en) * | 2009-08-21 | 2014-09-24 | 川崎化成工業株式会社 | 9,10-bis (substituted carbonyloxy) anthracene compound and photo radical polymerization initiator containing the same. |
| JP6160805B2 (en) * | 2012-11-20 | 2017-07-12 | 川崎化成工業株式会社 | Radical polymerization sensitizer. |
| WO2014109303A1 (en) * | 2013-01-11 | 2014-07-17 | 川崎化成工業株式会社 | Anthracene compound and use thereof as photopolymerization sensitizer |
| JP2018115256A (en) * | 2017-01-18 | 2018-07-26 | 川崎化成工業株式会社 | Photopolymerization sensitizer having migration resistance |
| JP2020016821A (en) * | 2018-07-27 | 2020-01-30 | 東洋インキＳｃホールディングス株式会社 | Color filter coloring composition and color filter |
| CN111752097A (en) * | 2019-03-29 | 2020-10-09 | 常州强力电子新材料股份有限公司 | Self-luminous photosensitive resin composition, color filter and image display device |
| JP7297499B2 (en) * | 2019-04-04 | 2023-06-26 | 東京応化工業株式会社 | Photosensitive resin composition, method for producing patterned cured film, and patterned cured film |
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2021
- 2021-07-16 WO PCT/CN2021/106686 patent/WO2023283915A1/en active Application Filing
-
2022
- 2022-07-08 CN CN202280049825.5A patent/CN117693714A/en active Pending
- 2022-07-08 WO PCT/CN2022/104595 patent/WO2023284643A1/en active Application Filing
- 2022-07-08 JP JP2024500515A patent/JP2024526665A/en active Pending
- 2022-07-08 KR KR1020247004722A patent/KR20240035832A/en unknown
- 2022-07-14 TW TW111126430A patent/TW202309656A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2023283915A1 (en) | 2023-01-19 |
| WO2023284643A1 (en) | 2023-01-19 |
| KR20240035832A (en) | 2024-03-18 |
| JP2024526665A (en) | 2024-07-19 |
| TW202309656A (en) | 2023-03-01 |
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