JP4756112B2 - 感光性樹脂組成物、これを用いた感光性エレメント、レジストパターンの形成方法、及びプリント配線板の製造方法 - Google Patents
感光性樹脂組成物、これを用いた感光性エレメント、レジストパターンの形成方法、及びプリント配線板の製造方法 Download PDFInfo
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- JP4756112B2 JP4756112B2 JP2011505289A JP2011505289A JP4756112B2 JP 4756112 B2 JP4756112 B2 JP 4756112B2 JP 2011505289 A JP2011505289 A JP 2011505289A JP 2011505289 A JP2011505289 A JP 2011505289A JP 4756112 B2 JP4756112 B2 JP 4756112B2
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- 239000011342 resin composition Substances 0.000 title claims description 121
- 238000000034 method Methods 0.000 title claims description 53
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- -1 pyrazine compound Chemical class 0.000 claims description 71
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 60
- 238000007747 plating Methods 0.000 claims description 60
- 150000001875 compounds Chemical class 0.000 claims description 59
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
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- 239000011230 binding agent Substances 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Natural products C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 18
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 17
- 238000011161 development Methods 0.000 claims description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 17
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 15
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- 125000003118 aryl group Chemical group 0.000 claims description 14
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- 125000002950 monocyclic group Chemical group 0.000 claims description 7
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- 238000000862 absorption spectrum Methods 0.000 description 6
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000005227 gel permeation chromatography Methods 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
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- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- OAZWDJGLIYNYMU-UHFFFAOYSA-N Leucocrystal Violet Chemical compound C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 OAZWDJGLIYNYMU-UHFFFAOYSA-N 0.000 description 4
- NPKSPKHJBVJUKB-UHFFFAOYSA-N N-phenylglycine Chemical compound OC(=O)CNC1=CC=CC=C1 NPKSPKHJBVJUKB-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- ISAOCJYIOMOJEB-UHFFFAOYSA-N desyl alcohol Natural products C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 238000003384 imaging method Methods 0.000 description 4
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- 239000004065 semiconductor Substances 0.000 description 4
- 150000003673 urethanes Chemical class 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- HSTOKWSFWGCZMH-UHFFFAOYSA-N 3,3'-diaminobenzidine Chemical compound C1=C(N)C(N)=CC=C1C1=CC=C(N)C(N)=C1 HSTOKWSFWGCZMH-UHFFFAOYSA-N 0.000 description 3
- 241000251468 Actinopterygii Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
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- 229910000365 copper sulfate Inorganic materials 0.000 description 3
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 3
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- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- 125000005259 triarylamine group Chemical group 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- FLFWJIBUZQARMD-UHFFFAOYSA-N 2-mercapto-1,3-benzoxazole Chemical compound C1=CC=C2OC(S)=NC2=C1 FLFWJIBUZQARMD-UHFFFAOYSA-N 0.000 description 2
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- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
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- 230000001737 promoting effect Effects 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical compound OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 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
- DFIWJEVKLWMZBI-UHFFFAOYSA-M sodium;dihydrogen phosphate;phosphoric acid Chemical compound [Na+].OP(O)(O)=O.OP(O)([O-])=O DFIWJEVKLWMZBI-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 150000001629 stilbenes Chemical class 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 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
- 150000003557 thiazoles Chemical class 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 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
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 150000007964 xanthones Chemical class 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
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/42—Benzopyrazines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/04—Acids; Metal salts or ammonium salts thereof
- C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
-
- 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
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- 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
-
- 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
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- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Materials For Photolithography (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
まず、本実施形態に係る感光性樹脂組成物について説明する。本実施形態の感光性樹脂組成物は、(A)バインダポリマー、(B)光重合性化合物及び(C)光重合開始剤を含有する。
次に、本実施形態に係る感光性樹脂組成物層及び感光性エレメントについて説明する。図1は、感光性エレメントの一例を示す模式断面図である。感光性エレメント1は、支持フィルム2、感光性樹脂組成物層3、及び場合により保護フィルム4が、この順に積層された積層体である。
上記感光性樹脂組成物を用いて、レジストパターンを形成することができる。本実施形態に係るレジストパターンの形成方法は、(i)上記感光性樹脂組成物からなる感光性樹脂組成物層を基板上に積層する積層工程と、(ii)感光性樹脂組成物層の所定部分に活性光線を照射する露光工程と、(iii)感光性樹脂組成物層の上記所定部分以外の部分を基板上から除去することにより、基板上に、感光性樹脂組成物の硬化物からなるレジストパターンを形成する現像工程と、を有する。
まず、感光性樹脂組成物からなる感光性樹脂組成物層を基板上に積層する。基板としては、絶縁層と該絶縁層上に形成された導体層とを備えた基板(回路形成用基板)を用いることができる。
次に、基板上の感光性樹脂組成物層の所定部分に活性光線を照射してその所定部分に露光し、硬化させる。この際、感光性樹脂組成物層上に存在する支持フィルムが活性光線に対して透過性を有する場合には、支持フィルムを通して活性光線を照射することができるが、支持フィルムが活性光線に対して遮光性を有する場合には、支持フィルムを除去した後に感光性樹脂組成物層に活性光線を照射する。
さらに、感光性樹脂組成物層の上記所定部分以外の部分を基板上から除去することにより、基板上に、感光性樹脂組成物の硬化物からなるレジストパターンを形成する。感光性樹脂組成物層上に支持フィルムが存在している場合には、支持フィルムを除去してから、上記所定部分(露光部分)以外の部分(未露光部分)の除去(現像)を行う。現像方法には、ウェット現像とドライ現像とがあるが、ウェット現像が広く用いられている。
上記方法によりレジストパターンが形成された基板をエッチング又はめっきすることにより、プリント配線板を製造することができる。基板のエッチング又はめっきは、形成されたレジストパターンをマスクとして、基板の導体層等に対して行われる。
[感光性樹脂組成物の溶液の調製]
下記表1及び表2に示す成分を、同表に示す配合量で混合することにより、実施例1〜13及び比較例1の感光性樹脂組成物の溶液を調製した。なお、表1及び表2に示す(A)成分の配合量は、不揮発分の質量(固形分量)である。下記表1及び表2に示す各成分の詳細については、以下のとおりである。
[バインダーポリマー(A−1)の合成]
重合性単量体(モノマー)であるメタクリル酸150g、メタクリル酸ベンジルエステル125g、メタクリル酸メチル25g及びスチレン200g(質量比30/25/5/40)と、アゾビスイソブチロニトリル9.0gとを混合して得た溶液を「溶液a」とした。
(GPC条件)
ポンプ:日立 L−6000型[(株)日立製作所製]
カラム:Gelpack GL−R420 + Gelpack GL−R430 + Gelpack GL−R440(計3本)(以上、日立化成工業(株)製、商品名)
溶離液:テトラヒドロフラン
測定温度:40℃
流量:2.05mL/分
検出器:日立 L−3300型RI[(株)日立製作所製]
TMPT21E:トリメチロールプロパンポリオキシエチレンエーテルトリメタクリレート(日立化成工業社製、商品名)
FA−321M:2,2−ビス(4−(メタクリロキシペンタエトキシ)フェニル)プロパン)(日立化成工業社製、商品名)
FA−024M:上記式(6)で表される化合物において、R20及びR21=メチル基、m3=6(平均値)、n2+n3=12(平均値)である化合物)(日立化成工業社製、商品名)
M−114:4−ノルマルノニルフェノキシオクタエチレングリコールアクリレート(東亞合成(株)製、商品名)
BPE−100;2,2−ビス(4−(メタクリロキシポリエトキシ)フェニル)プロパン)(1分子中に含まれるエチレンオキシド鎖の平均が2.6モル)(新中村化学社製、商品名)
[光重合開始剤(C−1)の合成]
エタノール20mL、3,3’,4,4’−ビフェニルテトラアミン2mmol及び3,3’−ジメトキシベンジル4mmolをフラスコに加えて混合し、フラスコ内の空気を窒素置換した後、混合物を80℃で12時間還流した。室温まで冷却し、200mLの水を加えた後、減圧濾過により、生成物(C−1)を得た。
3,3’−ジメトキシベンジルに換えて4,4’−ジメトキシベンジルを用いた他は上記(C−1)と同様にして、下記式(14)で表される構造の化合物を得た。
3,3’,4,4’−ビフェニルテトラアミン2mmol及び3,3’−ジメトキシベンジル4mmolの代わりに、2,3−ジアミノナフタレン2mmol及び3,3’−ジメトキシベンジル2mmolを用いた他は上記(C−1)と同様にして、下記式(11)で表される構造の化合物を得た。
3,3’,4,4’−ビフェニルテトラアミン2mmol及び3,3’−ジメトキシベンジル4mmolの代わりに、2,3−ジアミノナフタレン2mmol及び4,4’−ジメトキシベンジル2mmolを用いた他は上記(C−1)と同様にして、下記式(12)で表される構造の化合物を得た。
(C−1)、(C−2)、(C−3)及び(C−4)以外の光重合開始剤を以下に示す。
BCIM:2,2’−ビス(2−クロロフェニル)−4,4’,5,5’−テトラフェニルビスイミダゾール(Hampford社製、商品名)
TPS:α,α,α−トリブロモメチルフェニルスルホン
以下のようにして、生成物(C−1)、(C−2)、(C−3)の紫外可視吸収スペクトルの測定を行った。
実施例1で作製した生成物(C−1)を含むフィルム、及び実施例8で作製した生成物(C−3)を含むフィルムを用い、島津社製紫外可視分光光度計UV2550を用い、各サンプルフィルムの紫外可視吸収スペクトルを測定した。得られた結果を図4に示す。
また、生成物(C−1)、(C−2)をクロロホルム中、1×10-5mol/Lとなるよう秤取り、石英セルに入れ、島津社製紫外可視分光光度計UV2550を用い、各サンプル溶液の紫外可視吸収スペクトルを測定した。得られた結果を図5に示す。
LCV:ロイコクリスタルバイオレット
NPG:N−フェニルグリシン(R17=水素原子)
(D−1):2−メルカプトベンゾオキサゾール
ニッカフローMC:7−ジエチルアミノ−4−メチルクマリン(日本化学工業所社製、商品名)
DBA:9,10−ジブトキシアントラセン(川崎化成工業社製、商品名)
(E−1):1−フェニル−3−(4−イソプロピルスチリル)−5−(4−イソプロピルフェニル)ピラゾリン(日本化学工業所社製)
上記実施例1〜13及び比較例1の感光性樹脂組成物の溶液を、それぞれ厚さ16μmのポリエチレンテレフタレートフィルム(帝人(株)製、製品名「HTF−01」)上に均一に塗布し、70℃及び110℃の熱風対流式乾燥器で乾燥して、乾燥後の膜厚が40μmである感光性樹脂組成物層を形成した。この感光性樹脂組成物層上に保護フィルム(タマポリ(株)製、製品名「NF−15」)を貼り合わせ、ポリエチレンテレフタレートフィルム(支持フィルム)と、感光性樹脂組成物層と、保護フィルムとが順に積層された実施例1〜13及び比較例1の感光性エレメントを得た。
ガラスエポキシ材と、その両面に形成された銅箔(厚さ35μm)とからなる銅張積層板(日立化成工業(株)製、製品名MCL−E−67)の銅表面を、#600相当のブラシを持つ研磨機(三啓(株)製)を用いて研磨し、水洗後、空気流で乾燥させた。この銅張積層板(以下、「基板」という。)を加熱して80℃に昇温させた後、実施例1〜13及び比較例1の感光性エレメントを、基板の銅表面にラミネート(積層)した。ラミネートは、保護フィルムを除去しながら、各感光性エレメントの感光性樹脂組成物層が基板の銅表面に密着するようにして、温度120℃、ラミネート圧力4kgf/cm2の条件下で行った。このようにして、基板の銅表面上に感光性樹脂組成物層及びポリエチレンテレフタレートフィルムが積層された積層基板を得た。
得られた積層基板を放冷し、23℃になった時点で、積層基板のポリエチレンテレフタレートフィルム上に、濃度領域0.00〜2.00、濃度ステップ0.05、タブレットの大きさ20mm×187mm、各ステップの大きさが3mm×12mmである41段ステップタブレットを有するフォトツールを密着させた。波長405nmの青紫色レーザダイオードを光源とする日立ビアメカニクス社製直描機「DE−1AH」(商品名)を使用して、所定のエネルギー量(露光量)でフォトツール及びポリエチレンテレフタレートフィルムを介して感光性樹脂組成物層に対して露光を行った。なお、照度の測定は、405nm対応プローブを適用した紫外線照度計(ウシオ電機(株)製、商品名「UIT−150」)を用いて行った。
ライン幅(L)/スペース幅(S)(以下、「L/S」と記す。)が5/5〜30/30(単位:μm)である描画パターンを用いて、41段ステップタブレットの残存段数が20段となるエネルギー量で上記積層基板の感光性樹脂組成物層に対して露光(描画)を行った。露光後、上記感度の評価と同様の現像処理を行った。
上記解像性及び密着性の評価で得られたレジストパターンの形成された積層基板を硫酸銅/硫酸水溶液のめっき液に浸漬し、全電流値2Aで15分間電解銅めっきを行った。得られためっき銅厚は約15μmであった。めっき後の積層基板に、50℃の3質量%水酸化ナトリウム水溶液をスプレーし、レジストを基板から剥離除去した。光学顕微鏡を用いて剥離後の積層基板を観察し、めっきパターン(銅配線)間における硬化膜の剥離残りの有無を調べた。結果を表3及び表4に示す。
上記剥離特性の評価により得られた剥離後の積層基板を、光学顕微鏡を用いて観察し、めっきパターンが断線又は短絡することなく形成された最も小さいめっき幅によりめっき形成性を評価した。この数値が小さいほどめっき形成性が良好であることを意味する。結果を表3及び表4に示す。
各感光性エレメントを40cm×50cmの大きさに切り出し、保護フィルムを除去してステップタブレットが20段となる露光量で感光性樹脂組成物層に対して露光を行い、ポリエチレンテレフタレートフィルムを剥離し硬化膜を得た。この硬化膜を硫酸銅/硫酸水溶液のめっき液1Lに3日間浸漬した。ハルセル試験浴槽(山本鍍金試験機社製)を用いて上記銅張積層板(基板)に全電流値2Aで15分間電解銅めっきを行った。
Claims (11)
- バインダポリマーと、エチレン性不飽和結合を有する光重合性化合物と、下記式(1)、(2)、又は(3)で表される構造を有する化合物からなる群より選択される少なくとも1種のピラジン化合物と、を含有する感光性樹脂組成物。
- 前記ピラジン化合物が、前記式(1)で表される構造を有する化合物である請求項1に記載の感光性樹脂組成物。
- 前記ピラジン化合物の極大吸収波長が、350〜410nmの範囲内である請求項1又は2に記載の感光性樹脂組成物。
- 前記バインダポリマーが、(メタ)アクリル酸と、スチレン又はスチレン誘導体とを共重合成分として含む請求項1〜3のいずれか一項に記載の感光性樹脂組成物。
- 水素供与性化合物を更に含有する請求項1〜5のいずれか一項に記載の感光性樹脂組成物。
- 支持体と、該支持体上に形成された請求項1〜7のいずれか一項に記載の感光性樹脂組成物からなる感光性樹脂組成物層と、を備える感光性エレメント。
- 請求項1〜7のいずれか一項に記載の感光性樹脂組成物からなる感光性樹脂組成物層を基板上に積層する積層工程と、
前記感光性樹脂組成物層の所定部分に活性光線を照射する露光工程と、
前記感光性樹脂組成物層の前記所定部分以外の部分を前記基板上から除去することにより、前記基板上に、前記感光性樹脂組成物の硬化物からなるレジストパターンを形成する現像工程と、を含むレジストパターンの形成方法。 - 前記活性光線の波長が390〜410nmである、請求項9に記載のレジストパターンの形成方法。
- 請求項9又は10に記載の方法によりレジストパターンが形成された基板をエッチング又はめっきする工程を含む、プリント配線板の製造方法。
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