KR20190111791A - Photosensitive Resin Composition - Google Patents
Photosensitive Resin Composition Download PDFInfo
- Publication number
- KR20190111791A KR20190111791A KR1020190031104A KR20190031104A KR20190111791A KR 20190111791 A KR20190111791 A KR 20190111791A KR 1020190031104 A KR1020190031104 A KR 1020190031104A KR 20190031104 A KR20190031104 A KR 20190031104A KR 20190111791 A KR20190111791 A KR 20190111791A
- Authority
- KR
- South Korea
- Prior art keywords
- photosensitive resin
- resin composition
- acid
- carboxyl group
- compound
- Prior art date
Links
- 239000011342 resin composition Substances 0.000 title claims abstract description 61
- -1 aliphatic urea compound Chemical class 0.000 claims abstract description 61
- 229920005989 resin Polymers 0.000 claims abstract description 48
- 239000011347 resin Substances 0.000 claims abstract description 48
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 45
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- 239000004202 carbamide Substances 0.000 claims abstract description 28
- 239000004593 Epoxy Substances 0.000 claims abstract description 26
- 239000003085 diluting agent Substances 0.000 claims description 17
- 239000000463 material Substances 0.000 claims description 11
- FLFWJIBUZQARMD-UHFFFAOYSA-N 2-mercapto-1,3-benzoxazole Chemical compound C1=CC=C2OC(S)=NC2=C1 FLFWJIBUZQARMD-UHFFFAOYSA-N 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 238000000016 photochemical curing Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 10
- 239000000126 substance Substances 0.000 abstract description 10
- 238000003860 storage Methods 0.000 abstract description 7
- 239000003999 initiator Substances 0.000 abstract description 4
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- 239000010408 film Substances 0.000 description 48
- 238000000576 coating method Methods 0.000 description 27
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- 239000003086 colorant Substances 0.000 description 18
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 14
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 13
- 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 12
- 238000011156 evaluation Methods 0.000 description 12
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
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- 238000000034 method Methods 0.000 description 10
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- 239000003063 flame retardant Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
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- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 7
- 230000035945 sensitivity Effects 0.000 description 7
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- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
- 238000013329 compounding Methods 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229920001187 thermosetting polymer Polymers 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 3
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 238000007259 addition reaction Methods 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 239000002518 antifoaming agent Substances 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000013039 cover film Substances 0.000 description 3
- 229930003836 cresol Natural products 0.000 description 3
- UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000004898 kneading Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
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- 239000010936 titanium Substances 0.000 description 3
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- DPZSNGJNFHWQDC-ARJAWSKDSA-N (z)-2,3-diaminobut-2-enedinitrile Chemical compound N#CC(/N)=C(/N)C#N DPZSNGJNFHWQDC-ARJAWSKDSA-N 0.000 description 2
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-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
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 2
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- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- 229920002799 BoPET Polymers 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
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- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 206010034972 Photosensitivity reaction Diseases 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
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- 150000008065 acid anhydrides Chemical class 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
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- 150000001298 alcohols Chemical class 0.000 description 2
- LFYJSSARVMHQJB-QIXNEVBVSA-N bakuchiol Chemical compound CC(C)=CCC[C@@](C)(C=C)\C=C\C1=CC=C(O)C=C1 LFYJSSARVMHQJB-QIXNEVBVSA-N 0.000 description 2
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- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
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- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 2
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- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- PMUPSYZVABJEKC-UHFFFAOYSA-N 1-methylcyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1(C)CCCCC1C(O)=O PMUPSYZVABJEKC-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
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- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical class C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- VRRIVXLVXXAHJA-UHFFFAOYSA-N tris(2,3,4-tribromophenyl) phosphate Chemical compound BrC1=C(Br)C(Br)=CC=C1OP(=O)(OC=1C(=C(Br)C(Br)=CC=1)Br)OC1=CC=C(Br)C(Br)=C1Br VRRIVXLVXXAHJA-UHFFFAOYSA-N 0.000 description 1
- MHEGXVLDEDJADA-UHFFFAOYSA-N tris(2,3,4-trimethylphenyl) phosphate Chemical compound CC1=C(C)C(C)=CC=C1OP(=O)(OC=1C(=C(C)C(C)=CC=1)C)OC1=CC=C(C)C(C)=C1C MHEGXVLDEDJADA-UHFFFAOYSA-N 0.000 description 1
- LRSNDFOWYYKLHB-UHFFFAOYSA-N tris(2,3-dibromophenyl) phosphate Chemical compound BrC1=CC=CC(OP(=O)(OC=2C(=C(Br)C=CC=2)Br)OC=2C(=C(Br)C=CC=2)Br)=C1Br LRSNDFOWYYKLHB-UHFFFAOYSA-N 0.000 description 1
- JZZBTMVTLBHJHL-UHFFFAOYSA-N tris(2,3-dichloropropyl) phosphate Chemical compound ClCC(Cl)COP(=O)(OCC(Cl)CCl)OCC(Cl)CCl JZZBTMVTLBHJHL-UHFFFAOYSA-N 0.000 description 1
- WTLBZVNBAKMVDP-UHFFFAOYSA-N tris(2-butoxyethyl) phosphate Chemical compound CCCCOCCOP(=O)(OCCOCCCC)OCCOCCCC WTLBZVNBAKMVDP-UHFFFAOYSA-N 0.000 description 1
- HQUQLFOMPYWACS-UHFFFAOYSA-N tris(2-chloroethyl) phosphate Chemical compound ClCCOP(=O)(OCCCl)OCCCl HQUQLFOMPYWACS-UHFFFAOYSA-N 0.000 description 1
- GTRSAMFYSUBAGN-UHFFFAOYSA-N tris(2-chloropropyl) phosphate Chemical compound CC(Cl)COP(=O)(OCC(C)Cl)OCC(C)Cl GTRSAMFYSUBAGN-UHFFFAOYSA-N 0.000 description 1
- LIPMRGQQBZJCTM-UHFFFAOYSA-N tris(2-propan-2-ylphenyl) phosphate Chemical compound CC(C)C1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C(C)C)OC1=CC=CC=C1C(C)C LIPMRGQQBZJCTM-UHFFFAOYSA-N 0.000 description 1
- SPUXJWDKFVXXBI-UHFFFAOYSA-N tris(2-tert-butylphenyl) phosphate Chemical compound CC(C)(C)C1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C(C)(C)C)OC1=CC=CC=C1C(C)(C)C SPUXJWDKFVXXBI-UHFFFAOYSA-N 0.000 description 1
- LKOCAGKMEUHYBV-UHFFFAOYSA-N tris(3-bromo-3-chloropropyl) phosphate Chemical compound ClC(Br)CCOP(=O)(OCCC(Cl)Br)OCCC(Cl)Br LKOCAGKMEUHYBV-UHFFFAOYSA-N 0.000 description 1
- GXZLXDRFEDHOAU-UHFFFAOYSA-N tris(4-phenylphenyl) phosphate Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1OP(OC=1C=CC(=CC=1)C=1C=CC=CC=1)(=O)OC(C=C1)=CC=C1C1=CC=CC=C1 GXZLXDRFEDHOAU-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 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
-
- 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
- G03F7/0048—Photosensitive materials characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/22—Secondary treatment of printed circuits
- H05K3/28—Applying non-metallic protective coatings
- H05K3/285—Permanent coating compositions
- H05K3/287—Photosensitive compositions
Abstract
Description
본 발명은, 피복 재료, 예를 들면, 절연 피복 재료에 적절한 감광성 수지 조성물, 감광성 수지 조성물을 필름에 도포한 도막을 포함한 드라이 필름 및 감광성 수지 조성물을 경화시킨 경화물을 피복한 프린트 배선판에 관한 것이다.This invention relates to the printed wiring board which coat | covered the photosensitive resin composition suitable for a coating material, for example, an insulating coating material, the dry film containing the coating film which apply | coated the photosensitive resin composition to the film, and the hardened | cured material which hardened the photosensitive resin composition. .
기판 상에는 도체(예를 들면, 동박)의 도체 회로 패턴이 형성되고, 상기 회로 패턴의 납땜 랜드에 전자 부품을 납땜에 의해 탑재하고, 그 납땜 랜드를 제외한 회로 부분은, 보호막으로서의 절연 피막인 솔더 레지스트막으로 피복된다. 상기 절연 피막으로서, 카복실기 함유 감광성 수지와 광중합 개시제를 함유하는 감광성 수지 조성물의 경화막이 사용된다.The conductor circuit pattern of a conductor (for example, copper foil) is formed on a board | substrate, the electronic component is mounted in the soldering land of the said circuit pattern by soldering, and the circuit part except this soldering land is the soldering resist which is an insulating film as a protective film. Covered with a membrane. As said insulating film, the cured film of the photosensitive resin composition containing a carboxyl group-containing photosensitive resin and a photoinitiator is used.
카복실기 함유 감광성 수지와 광중합 개시제를 함유하는 감광성 수지 조성물로서, (A) 분자 중에 카복실기와 에틸렌성 불포화 이중 결합을 가지는 우레탄 수지, (B) 광중합 개시제, 및 (C) 열경화성 성분으로서의 블록이소시아네이트를 함유하는 것을 특징으로 하는 광경화성·열경화성 수지 조성물이 제안되어 있다(특허문헌 1). 또한, 특허문헌 1의 광경화성·열경화성 수지 조성물에서는, 보존 안정성이 우수하여, 1액형으로 조성할 수 있는 것이 기재되어 있다.A photosensitive resin composition containing a carboxyl group-containing photosensitive resin and a photopolymerization initiator, comprising (A) a urethane resin having a carboxyl group and an ethylenically unsaturated double bond in the molecule, (B) a photopolymerization initiator, and (C) a block isocyanate as a thermosetting component Photocurable thermosetting resin composition characterized by the above-mentioned is proposed (patent document 1). Moreover, in the photocurable thermosetting resin composition of patent document 1, it is excellent in storage stability, and it can describe that it can be formed in 1-component type.
한편, 카복실기 함유 감광성 수지를 함유하는 감광성 수지 조성물에, 한층 더 에폭시 화합물이 포함되는 경우가 있다. 카복실기 함유 감광성 수지와 에폭시 화합물이 공존하면, 감광성 수지 조성물의 보존 중에, 카복실기 함유 감광성 수지와 에폭시 화합물의 반응이 진행된다. 따라서, 특허문헌 1의 광경화성·열경화성 수지 조성물에서는, 1액형으로 조성하면, 포트 라이프에 문제가 있어, 보존 안정성에 개선의 여지가 있었다. 또한, 감광성 수지 조성물을 2액형으로 하고, 카복실기 함유 감광성 수지를 함유하는 성분과 에폭시 화합물을 함유하는 성분을 따로 보관하면, 관리가 번잡하고, 또한, 감광성 수지 조성물의 도공 작업이 복잡하게 되어 버린다.On the other hand, an epoxy compound may be further contained in the photosensitive resin composition containing a carboxyl group-containing photosensitive resin. When a carboxyl group-containing photosensitive resin and an epoxy compound coexist, reaction of a carboxyl group-containing photosensitive resin and an epoxy compound advances during storage of the photosensitive resin composition. Therefore, in the photocurable and thermosetting resin composition of patent document 1, when it consists of 1-component type, there existed a problem in pot life, and there existed room for improvement in storage stability. In addition, when the photosensitive resin composition is made into a two-part type and the component containing the carboxyl group-containing photosensitive resin and the component containing the epoxy compound are separately stored, management is complicated and the coating work of the photosensitive resin composition becomes complicated. .
또한, 특허문헌 1에서는, 솔더 레지스트막의 기본 특성인, 무기산이나 알코올류 등에 대한 내성, 즉, 내약품성에 개선의 여지가 있었다.Moreover, in patent document 1, there existed room for improvement in resistance to inorganic acids, alcohols, etc., ie, chemical resistance, which are the basic characteristics of a soldering resist film.
상기 사정을 감안하여, 본 발명의 목적은, 내약품성을 얻으면서, 1액형으로 조성해도, 보존 중에 카복실기 함유 감광성 수지와 에폭시 화합물과의 반응이 진행되어 버리는 것을 방지하여, 우수한 포트 라이프를 가지는 감광성 수지 조성물을 제공하는 것이다.In view of the above circumstances, an object of the present invention, while obtaining a chemical resistance, even if the composition is formed in a one-component type, it is possible to prevent the reaction between the carboxyl group-containing photosensitive resin and the epoxy compound during storage and to have an excellent pot life. It is providing a photosensitive resin composition.
본 발명의 양태는, (A) 카복실기 함유 감광성 수지와, (B) 광중합 개시제와, (C) 에폭시 화합물과, (D) 지방족계 우레아 화합물을 함유하는 것을 특징으로 하는 감광성 수지 조성물이다.The aspect of this invention is a photosensitive resin composition containing (A) carboxyl group-containing photosensitive resin, (B) photoinitiator, (C) epoxy compound, and (D) aliphatic urea compound.
본 발명의 양태는, 상기 (D) 지방족계 우레아 화합물이, 하기 일반식(1)In the aspect of the present invention, the (D) aliphatic urea compound is represented by the following general formula (1)
[화 1][Tue 1]
(식 중, R1, R2, R3, R4, R5, R6, R7는, 각각, 독립적으로, 탄소수 1~20개의 포화 지방족 탄화수소기, 또는 적어도 1개의 에틸렌성 불포화기를 가지는 탄소수 2~20개의 불포화 지방족 탄화수소기를 의미한다.)로 나타내는 화합물인 것을 특징으로 하는 감광성 수지 조성물이다.(In formula, R <1> , R <2> , R <3> , R <4> , R <5> , R <6> , R <7> respectively independently has a C1-C20 saturated aliphatic hydrocarbon group or at least 1 ethylenically unsaturated group. It is a compound represented by C2-C20 unsaturated aliphatic hydrocarbon group.) It is a photosensitive resin composition characterized by the above-mentioned.
본 발명의 양태는, 상기 R1, R2, R3, R4, R5, R6, R7는, 각각, 독립적으로, 탄소수 1~5개의 포화 지방족 탄화수소기인 것을 특징으로 하는 감광성 수지 조성물이다.In the aspect of the present invention, the R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 each independently represent a C 1-5 saturated aliphatic hydrocarbon group, wherein the photosensitive resin composition to be.
본 발명의 양태는, 상기 R1, R2, R3, R4, R5, R6, R7는, 각각 메틸기인 것을 특징으로 하는 감광성 수지 조성물이다.The aspect of this invention is said photosensitive resin composition characterized by said R <1> , R <2> , R <3> , R <4> , R <5> , R <6> , and R <7> each being a methyl group.
본 발명의 양태는, 상기 (A) 카복실기 함유 감광성 수지 100 질량부에 대해, 상기 (D) 지방족계 우레아 화합물이, 10 질량부 이상 및 30 질량부 이하로 함유되는 것을 특징으로 하는 감광성 수지 조성물이다.The aspect of this invention contains the said (D) aliphatic urea compound in 10 mass parts or more and 30 mass parts or less with respect to 100 mass parts of said (A) carboxyl group-containing photosensitive resin, The photosensitive resin composition characterized by the above-mentioned. to be.
본 발명의 양태는, (E) 반응성 희석제를 더 함유하는 것을 특징으로 하는 감광성 수지 조성물이다.The aspect of this invention is a photosensitive resin composition containing (E) reactive diluent further.
본 발명의 양태는, 머캅토벤즈옥사졸 및/또는 머캅토벤즈옥사졸 유도체를 더 함유하는 것을 특징으로 하는 감광성 수지 조성물이다.The aspect of this invention is a photosensitive resin composition which further contains a mercaptobenzoxazole and / or a mercaptobenzoxazole derivative.
본 발명의 양태는, 상기 감광성 수지 조성물의 광경화물이다.An aspect of the present invention is a photocured product of the photosensitive resin composition.
본 발명의 양태는, 상기 감광성 수지 조성물을 포함한 드라이 필름이다.The aspect of this invention is a dry film containing the said photosensitive resin composition.
본 발명의 양태는, 상기 광경화물을 포함한 프린트 배선판이다.The aspect of this invention is a printed wiring board containing the said photocured material.
본 발명의 양태에 따르면, 카복실기 함유 감광성 수지와 에폭시 화합물을 함유하는 감광성 수지 조성물에, 지방족계 우레아 화합물이 배합됨으로써, 감광성 수지 조성물을 1액형으로 해도, 보존 중에 카복실기 함유 감광성 수지와 에폭시 화합물과의 반응이 진행되어 버리는 것을 방지하여, 우수한 포트 라이프를 얻을 수 있으며, 또한, 내약품성을 얻을 수도 있다.According to the aspect of this invention, when an aliphatic urea compound is mix | blended with the photosensitive resin composition containing a carboxyl group-containing photosensitive resin and an epoxy compound, even if the photosensitive resin composition is 1-pack type, carboxyl group-containing photosensitive resin and an epoxy compound are preserve | saved during storage. The reaction with can be prevented from progressing, excellent pot life can be obtained, and chemical resistance can also be obtained.
본 발명의 양태에 따르면, 지방족계 우레아 화합물이, 일반식(1)로 나타내는 화합물이라는 점에서, 포트 라이프를 한층 더 향상시킬 수 있다.According to the aspect of this invention, since an aliphatic urea compound is a compound represented by General formula (1), pot life can be improved further.
본 발명의 양태에 따르면, 카복실기 함유 감광성 수지 100 질량부에 대해, 지방족계 우레아 화합물이, 10 질량부 이상 및 30 질량부 이하 함유함으로써, 포트 라이프를 한층 더 향상시킬 수 있다.According to an aspect of the present invention, the pot life can be further improved by containing 10 parts by mass or more and 30 parts by mass or less of the aliphatic urea compound with respect to 100 parts by mass of the carboxyl group-containing photosensitive resin.
이어서, 본 발명의 감광성 수지 조성물에 대해서, 이하에 설명한다. 본 발명의 감광성 수지 조성물은, (A) 카복실기 함유 감광성 수지와, (B) 광중합 개시제와, (C) 에폭시 화합물과, (D) 지방족계 우레아 화합물을 함유한다.Next, the photosensitive resin composition of this invention is demonstrated below. The photosensitive resin composition of this invention contains (A) carboxyl group-containing photosensitive resin, (B) photoinitiator, (C) epoxy compound, and (D) aliphatic urea compound.
(A) (A) 카복실기Carboxyl group 함유 감광성 수지 Containing photosensitive resin
카복실기 함유 감광성 수지는, 특별히 한정되지 않고, 예를 들면, 1분자 중에, 감광성의 불포화 이중 결합을 1개 이상, 바람직하게는 2개 이상 가지는 수지를 들 수 있다. 카복실기 함유 감광성 수지로서, 예를 들면, 1분자 중에 에폭시기를 2개 이상 가지는 다관능 에폭시 수지의 에폭시기 중 적어도 일부에, 아크릴산이나 메타크릴산(이하, 「(메타)아크릴산」이라고 하는 경우가 있다.) 등의 래디컬 중합성 불포화 모노카복실산을 반응시키고, 에폭시(메타)아크릴레이트 등의 래디컬 중합성 불포화 모노카복실산화 에폭시 수지를 얻고, 생성한 수산기에 다염기산 또는 그 무수물을 반응시켜 얻을 수 있는, 다염기산 변성 에폭시(메타)아크릴레이트 등의 다염기산 변성 래디컬 중합성 불포화 모노카복실산화 에폭시 수지를 들 수 있다.The carboxyl group-containing photosensitive resin is not particularly limited, and for example, a resin having one or more, preferably two or more, photosensitive unsaturated double bonds in one molecule may be mentioned. As carboxyl group-containing photosensitive resin, acrylic acid and methacrylic acid (henceforth "(meth) acrylic acid") may be called at least one part of the epoxy group of the polyfunctional epoxy resin which has two or more epoxy groups in 1 molecule, for example. A polybasic acid obtained by reacting a radical polymerizable unsaturated monocarboxylic acid such as.), Obtaining a radical polymerizable unsaturated monocarboxylic acid epoxy resin such as epoxy (meth) acrylate, and reacting the resulting hydroxyl group with a polybasic acid or an anhydride thereof. Polybasic acid modified radically polymerizable unsaturated monocarboxylic acid epoxy resins, such as a modified epoxy (meth) acrylate, are mentioned.
상기 다관능성 에폭시 수지는, 2관능 이상의 에폭시 수지면, 특별히 한정되지 않고, 어느 화학 구조에서도 사용할 수 있다. 다관능성 에폭시 수지의 에폭시 당량은, 특별히 한정되지 않지만, 그 상한값은, 3000g/eq가 바람직하고, 1000g/eq가 보다 바람직하고, 500g/eq가 특히 바람직하다. 한편, 다관능성 에폭시 수지의 에폭시 당량의 하한값은, 100g/eq가 바람직하고, 200g/eq가 특히 바람직하다.The polyfunctional epoxy resin is not particularly limited as long as it is a bifunctional or higher epoxy resin, and can be used in any chemical structure. Although the epoxy equivalent of a polyfunctional epoxy resin is not specifically limited, 3000 g / eq is preferable, as for the upper limit, 1000 g / eq is more preferable, 500 g / eq is especially preferable. On the other hand, 100 g / eq is preferable and, as for the minimum of the epoxy equivalent of a polyfunctional epoxy resin, 200 g / eq is especially preferable.
다관능성 에폭시 수지에는, 예를 들면, 비페닐아랄킬형 에폭시 수지, 페닐아랄킬형 에폭시 수지, 비페닐형 에폭시 수지, 나프탈렌형 에폭시 수지, 디시클로펜타디엔형 에폭시 수지, ε-카프로락톤 변성 에폭시 수지, 비스페놀 A형 에폭시 수지, 비스페놀 F형 에폭시 수지, 페놀 노볼락형 에폭시 수지, о-크레졸 노볼락형 등의 크레졸 노볼락형 에폭시 수지, 비스페놀 A 노볼락형 에폭시 수지, 고리형 지방족 에폭시 수지, 글리시딜에스테르형 에폭시 수지, 글리시딜아민형 에폭시 수지, 복소환식 에폭시 수지, 비스페놀 변성 노볼락형 에폭시 수지 등을 들 수 있다. 또한, 이들 수지에 Br, Cl 등의 할로겐 원자를 도입한 것을 사용해도 좋다. 이들 에폭시 수지는 단독으로 사용해도 좋고, 또한 2종 이상을 병용해도 좋다.Examples of the polyfunctional epoxy resin include biphenyl aralkyl type epoxy resins, phenyl aralkyl type epoxy resins, biphenyl type epoxy resins, naphthalene type epoxy resins, dicyclopentadiene type epoxy resins, and ε-caprolactone modified epoxy resins. Bisphenol A type epoxy resin, bisphenol F type epoxy resin, phenol novolak type epoxy resin, cresol novolak type epoxy resin such as о-cresol novolak type, bisphenol A novolak type epoxy resin, cyclic aliphatic epoxy resin, glycy A diester type epoxy resin, a glycidyl amine type epoxy resin, a heterocyclic epoxy resin, a bisphenol modified novolak-type epoxy resin, etc. are mentioned. Moreover, you may use what introduce | transduced halogen atoms, such as Br and Cl, into these resin. These epoxy resins may be used independently and may use 2 or more types together.
래디컬 중합성 불포화 모노카복실산은, 특별히 한정되지 않고, 예를 들면, (메타)아크릴산, 크로톤산, 계피산(신남산) 등을 들 수 있으며, 이 중, 입수 용이성의 점에서, (메타)아크릴산이 바람직하다. 이들 래디컬 중합성 불포화 모노카복실산은 단독으로 사용해도 좋고, 또한 2종 이상을 병용해도 좋다.Radical polymerizable unsaturated monocarboxylic acid is not specifically limited, For example, (meth) acrylic acid, crotonic acid, cinnamic acid (cinnamic acid), etc. are mentioned, Among these, from the point of availability, (meth) acrylic acid is desirable. These radically polymerizable unsaturated monocarboxylic acids may be used independently and may use 2 or more types together.
에폭시 수지와 래디컬 중합성 불포화 모노카복실산과의 반응 방법은, 특별히 한정되지 않고, 예를 들면, 에폭시 수지와 래디컬 중합성 불포화 모노카복실산을 적당한 희석제(예를 들면, 유기용제) 중에서 가열함으로써 반응시킬 수 있다.The reaction method of an epoxy resin and radically polymerizable unsaturated monocarboxylic acid is not specifically limited, For example, it can react by heating an epoxy resin and radically polymerizable unsaturated monocarboxylic acid in a suitable diluent (for example, organic solvent). have.
다염기산 또는 다염기산 무수물은, 상기 에폭시 수지와 래디컬 중합성 불포화 모노카복실산과의 반응에 의해 생성한 수산기에 반응하여, 감광성 수지에 유리(遊離)된 카복실기를 도입하기 위한 것이다. 감광성 수지에 유리된 카복실기가 도입됨으로써, 알칼리 현상성이 부여된다. 다염기산 또는 그 무수물은, 특별히 한정되지 않고, 포화, 불포화 모두 사용 가능하다. 다염기산에는, 예를 들면, 숙신산, 말레산, 아디프산, 구연산, 프탈산, 프탈산 유도체(예를 들면, 테트라히드로프탈산, 3-메틸테트라히드로프탈산, 4-메틸테트라히드로프탈산, 3-에틸테트라히드로프탈산, 4-에틸테트라히드로프탈산, 헥사히드로프탈산, 3-메틸헥사히드로프탈산, 4-메틸헥사히드로프탈산, 3-에틸헥사히드로프탈산, 4-에틸헥사히드로프탈산, 메틸테트라히드로프탈산, 메틸헥사히드로프탈산, 엔드메틸렌테트라히드로프탈산, 메틸엔드메틸렌테트라히드로프탈산), 트리멜리트산, 피로멜리트산 및 디글리콜산 등을 들 수 있다. 또한, 다염기산 무수물로서는, 이들 다염기산의 무수물을 들 수 있다. 이들 화합물은 단독으로 사용해도 좋고, 2종 이상을 병용해도 좋다.The polybasic acid or polybasic acid anhydride reacts with the hydroxyl group produced by the reaction of the epoxy resin with the radical polymerizable unsaturated monocarboxylic acid to introduce a free carboxyl group into the photosensitive resin. Alkali developability is provided by introducing a carboxyl group liberated in the photosensitive resin. The polybasic acid or its anhydride is not particularly limited, and both saturated and unsaturated compounds can be used. Examples of the polybasic acid include succinic acid, maleic acid, adipic acid, citric acid, phthalic acid, and phthalic acid derivatives (for example, tetrahydrophthalic acid, 3-methyltetrahydrophthalic acid, 4-methyltetrahydrophthalic acid, and 3-ethyltetrahydro). Phthalic acid, 4-ethyltetrahydrophthalic acid, hexahydrophthalic acid, 3-methylhexahydrophthalic acid, 4-methylhexahydrophthalic acid, 3-ethylhexahydrophthalic acid, 4-ethylhexahydrophthalic acid, methyltetrahydrophthalic acid, methylhexahydrophthalic acid , Endmethylenetetrahydrophthalic acid, methylendmethylenetetrahydrophthalic acid), trimellitic acid, pyromellitic acid, diglycolic acid, and the like. Moreover, as polybasic acid anhydride, anhydrides of these polybasic acids are mentioned. These compounds may be used independently and may use 2 or more types together.
본 발명에 있어서, 상기 다염기산 변성 래디컬 중합성 불포화 모노카복실산화 에폭시 수지도 카복실기 함유 감광성 수지로서 사용할 수 있지만, 필요에 따라, 상기 다염기산 변성 래디컬 중합성 불포화 모노카복실산화 에폭시 수지의 카복실기에, 1개 이상의 래디컬 중합성 불포화기와 에폭시기를 가지는 글리시딜 화합물을 반응시키고, 측쇄에 래디컬 중합성 불포화기를 한층 더 도입하여, 감광성을 보다 향상시킨 카복실기 함유 감광성 수지도 좋다.In the present invention, the polybasic acid-modified radically polymerizable unsaturated monocarboxylic acid-epoxy resin can also be used as the carboxyl group-containing photosensitive resin, but if necessary, one of the carboxyl groups of the polybasic acid-modified radically polymerizable unsaturated monocarboxylic acid-epoxy resin The carboxyl group-containing photosensitive resin which made the radically polymerizable unsaturated group and the glycidyl compound which have an epoxy group react, introduce | transduces a radically polymerizable unsaturated group further in the side chain, and improved the photosensitivity further may be sufficient.
상기 감광성을 보다 향상시킨 카복실기 함유 감광성 수지는, 상기 글리시딜 화합물의 반응에 의해, 래디컬 중합성 불포화기가, 다염기산 변성 래디컬 중합성 불포화 모노카복실산화 에폭시 수지 골격의 측쇄에 결합하기 때문에, 광중합 반응성, 즉, 광경화성이 보다 향상되고, 보다 우수한 감광 특성을 가진다. 1개 이상의 래디컬 중합성 불포화기와 에폭시기를 가지는 화합물로서는, 예를 들면, 글리시딜아크릴레이트, 글리시딜메타크릴레이트, 아릴글리시딜에테르, 펜타에리쓰리톨트리아크릴레이트모노글리시딜에테르, ,펜타에리쓰리톨트리메타아크릴레이트모노글리시딜에테르 등을 들 수 있다. 상기 1개 이상의 래디컬 중합성 불포화기와 에폭시기를 갖는 화합물은, 단독으로 사용해도 좋고, 2종 이상을 병용해도 좋다.Since the radical polymerizable unsaturated group couple | bonds with the side chain of polybasic acid-modified radically polymerizable unsaturated monocarboxylic acid-ized epoxy resin frame | skeleton by reaction of the said glycidyl compound, the said carboxyl group-containing photosensitive resin which improved the said photosensitivity is photopolymerization reactivity That is, photocurability is further improved and it has more excellent photosensitive characteristic. As a compound which has one or more radically polymerizable unsaturated group and an epoxy group, For example, glycidyl acrylate, glycidyl methacrylate, aryl glycidyl ether, pentaerythritol triacrylate monoglycidyl ether, And pentaerythritol trimethacrylate monoglycidyl ether and the like. The compound which has the said 1 or more radically polymerizable unsaturated group and an epoxy group may be used independently, and may use 2 or more types together.
카복실기 함유 감광성 수지의 산가는, 특별히 한정되지 않지만, 그 하한값은, 확실한 알칼리 현상성을 얻는다는 점에서, 30mgKOH/g가 바람직하고, 40mgKOH/g가 특히 바람직하다. 한편, 카복실기 함유 감광성 수지의 산가의 상한값은, 알칼리 현상액에 의한 노광부의 용해 방지의 점에서, 200mgKOH/g가 바람직하고, 경화물의 내습성과 절연성의 저하 방지의 점에서, 150mgKOH/g가 특히 바람직하다.Although the acid value of carboxyl group-containing photosensitive resin is not specifically limited, 30 mgKOH / g is preferable and 40 mgKOH / g is especially preferable at the point that the lower limit acquires reliable alkali developability. On the other hand, as for the upper limit of the acid value of carboxyl group-containing photosensitive resin, 200 mgKOH / g is preferable at the point of the prevention of the dissolution of the exposure part by alkaline developing solution, and 150 mgKOH / g is especially preferable at the point of preventing the fall of moisture resistance and insulation of hardened | cured material. Do.
또한, 카복실기 함유 감광성 수지의 질량 평균 분자량은, 특별히 한정되지 않지만, 그 하한값은, 경화물의 강인성(强靭性) 및 지촉건조성의 점에서, 6000이 바람직하고, 7000이 특히 바람직하다. 한편, 카복실기 함유 감광성 수지의 질량 평균 분자량의 상한값은, 알칼리 현상성의 저하를 확실히 방지한다는 점에서, 200000이 바람직하고, 50000이 특히 바람직하다.In addition, although the mass average molecular weight of a carboxyl group-containing photosensitive resin is not specifically limited, 6000 is preferable and 7000 are especially preferable at the point of the toughness and dryness of hardened | cured material. On the other hand, 200000 is preferable and 50000 is especially preferable at the point which the upper limit of the mass mean molecular weight of carboxyl group-containing photosensitive resin prevents fall of alkali developability.
카복실기 함유 감광성 수지는, 상기 각 원재료를 이용해 상기 반응에서 합성해도 좋고, 출시되어 있는 카복실기 함유 감광성 수지를 사용해도 좋다. 출시되어 있는 카복실기 함유 감광성 수지로서는, 예를 들면, 「SP-4621」(쇼와덴코(주)), 「ZAR-2000」, 「ZFR-1122」, 「FLX-2089」, 「ZCR-1569H」(이상, 니혼카야쿠(주)), 「사이크로머 P(ACA) Z-250」(다이셀·올넥스(주)) 등을 들 수 있다. 또한, 이들 카복실기 함유 감광성 수지는, 단독으로 사용해도 좋고, 2종 이상을 병용해도 좋다.Carboxyl group containing photosensitive resin may be synthesize | combined by the said reaction using each said raw material, and carboxyl group containing photosensitive resin currently marketed may be used. As a carboxyl group-containing photosensitive resin on the market, for example, "SP-4621" (Showa Denko Co., Ltd.), "ZAR-2000", "ZFR-1122", "FLX-2089", "ZCR-1569H", for example. (Nippon Kayaku Co., Ltd.), "Cyclomer P (ACA) Z-250" (Diecel Allnex Co., Ltd.), etc. are mentioned above. In addition, these carboxyl group-containing photosensitive resin may be used independently and may use 2 or more types together.
(B) (B) 광중합Photopolymerization 개시제Initiator
광중합 개시제는, 특별히 한정되지 않고, 모두 사용할 수 있다. 광중합 개시제로서는, 예를 들면, 1, 2-옥탄디온, 1-[4-(페닐티오)-2-(O-벤조일옥심)], 에타논1-[9-에틸-6-(2-메틸벤조일)-9H-카바졸-3-일]-1-(0-아세틸옥심), 2-(아세틸옥시이미노메틸)티오크산텐-9-온, 1, 8-옥탄디온, 1, 8-비스[9-에틸-6-니트로-9H-카바졸-3-일]-, 1, 8-비스(O-아세틸옥심), 1, 8-옥탄디온, 1, 8-비스[9-(2-에틸헥실)-6-니트로-9H-카바졸-3-일]-, 1, 8-비스(O-아세틸옥심), (Z)-(9-에틸-6-니트로-9H-카바졸-3-일)(4-((1-메톡시프로판-2-일)옥시)-2-메틸페닐)메타논O-아세틸옥심 등의 옥심 에스테르계 광중합 개시제, 페닐비스(2, 4, 6-트리메틸벤조일)포스핀옥사이드, 벤조인, 벤조인메틸에테르, 벤조인에틸에테르, 벤조인이소프로필에테르, 벤조인n부틸에테르, 벤조인이소부틸에테르, 아세토페논, 디메틸아미노아세토페논, 2, 2디메톡시2페닐아세토페논, 2, 2디에톡시2페닐아세토페논, 1-벤질-1-(디메틸아미노)프로필-4-모르폴리노페닐케톤, 2-메틸-4'-(메틸티오)-2-모르폴리노프로피오페논, 2-벤질-2-디메틸아미노-1-(4-모르폴리노페닐)-부탄온-1, 2히드록시2메틸1페닐프로판1온, 1히드록시시클로헥실페닐케톤, 4(2히드록시에톡시)페닐2히드록시2프로필)케톤, 벤조페논, p페닐벤조페논, 4, 4'비스(디에틸 아미노)벤조페논, 디클로로벤조페논, 2메틸안트라퀴논, 2에틸안트라퀴논, 23급-부틸안트라퀴논, 2아미노안트라퀴논, 2메틸티오크산톤, 2에틸티오크산톤, 2클로로티오크산톤, 2,4디메틸티오크산톤, 2,4디에틸티오크산톤, 벤질디메틸케탈, 아세토페논디메틸케탈, P디메틸아미노벤조산에틸에스테르 등을 들 수 있다. 이들 화합물은, 단독으로 사용해도 좋고, 2종 이상을 병용해도 좋다. 광중합 개시제의 함유량은, 특별히 한정되지 않지만, 카복실기 함유 감광성 수지 100 질량부(고형분, 이하 동일.)에 대해서, 1.0~10 질량부가 바람직하고, 2.0~8.0 질량부가 특히 바람직하다.A photoinitiator is not specifically limited, All can be used. As a photoinitiator, it is 1, 2-octanedione, 1- [4- (phenylthio) -2- (O-benzoyl oxime)], ethanone 1- [9-ethyl-6- (2-methyl, for example). Benzoyl) -9H-carbazol-3-yl] -1- (0-acetyloxime), 2- (acetyloxyiminomethyl) thioxanthene-9-one, 1, 8-octanedione, 1, 8-bis [9-ethyl-6-nitro-9H-carbazol-3-yl]-, 1, 8-bis (O-acetyloxime), 1, 8-octanedione, 1, 8-bis [9- (2- Ethylhexyl) -6-nitro-9H-carbazol-3-yl]-, 1, 8-bis (O-acetyloxime), (Z)-(9-ethyl-6-nitro-9H-carbazole-3 -Yl) (4-((1-methoxypropan-2-yl) oxy) -2-methylphenyl) methanone oxime ester photoinitiators such as O-acetyl oxime, phenylbis (2, 4, 6-trimethylbenzoyl Phosphine oxide, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin n butyl ether, benzoin isobutyl ether, acetophenone, dimethylaminoacetophenone, 2, 2 dimethoxy 2 Phenylacetophenone, 2, 2 diethoxy 2 Nylacetophenone, 1-benzyl-1- (dimethylamino) propyl-4-morpholinophenylketone, 2-methyl-4 '-(methylthio) -2-morpholinopropiophenone, 2-benzyl-2 -Dimethylamino-1- (4-morpholinophenyl) -butanone-1,2hydroxy2methyl1phenylpropane1-one, 1hydroxycyclohexylphenylketone, 4 (2hydroxyethoxy) phenyl2hydride Hydroxy2propyl) ketone, benzophenone, pphenylbenzophenone, 4,4'bis (diethyl amino) benzophenone, dichlorobenzophenone, 2methylanthraquinone, 2ethylanthraquinone, 23-butylanthraquinone, 2 Aminoanthraquinone, 2methyl thioxanthone, 2 ethyl thioxanthone, 2chloro thioxanthone, 2,4 dimethyl thioxanthone, 2,4 diethyl thioxanthone, benzyl dimethyl ketal, acetophenone dimethyl ketal, Pdimethyl Aminobenzoic acid ethyl ester etc. are mentioned. These compounds may be used independently and may use 2 or more types together. Although content of a photoinitiator is not specifically limited, 1.0-10 mass parts is preferable with respect to 100 mass parts (solid content, the same below) of carboxyl group-containing photosensitive resin, and 2.0-8.0 mass parts is especially preferable.
(C) 에폭시 화합물(C) epoxy compound
에폭시 화합물은, 감광성 수지 조성물의 광경화물의 가교 밀도를 올리고, 충분한 기계적 강도를 가지는 경화 도막을 얻기 위한 것이다. 에폭시 화합물로서는, 예를 들면, 에폭시 수지를 들 수 있다. 에폭시 수지로서는, 예를 들면, 비페닐형 에폭시 수지, 비페닐아랄킬형 에폭시 수지, 비스페놀 A형 에폭시 수지, 테트라메틸비스페놀 F형 에폭시 수지 등의 비스페놀 F형 에폭시 수지, 페놀노볼락형 에폭시 수지, 크레졸노볼락형 에폭시 수지, 디시클로펜타디엔형 에폭시 수지, 아다만탄형 에폭시 수지를 들 수 있다. 이들 중, 포트 라이프를 한층 더 향상시킨다는 점에서, 비스페놀 A형 에폭시 수지, 비페닐형 에폭시 수지, 테트라메틸비스페놀 F형 에폭시 수지가 바람직하고, 비페닐형 에폭시 수지, 테트라메틸비스페놀 F형 에폭시 수지가 특히 바람직하다. 이들 화합물은 단독으로 사용해도 좋고, 2종 이상을 병용해도 좋다.An epoxy compound is for raising the crosslinking density of the photocured material of the photosensitive resin composition, and obtaining a cured coating film which has sufficient mechanical strength. As an epoxy compound, an epoxy resin is mentioned, for example. As an epoxy resin, For example, bisphenol F-type epoxy resins, such as a biphenyl type epoxy resin, a biphenyl aralkyl type epoxy resin, a bisphenol A type epoxy resin, and a tetramethyl bisphenol F type epoxy resin, a phenol novolak type epoxy resin, and a cresol A novolak-type epoxy resin, a dicyclopentadiene type epoxy resin, and an adamantane type epoxy resin are mentioned. Among them, bisphenol A type epoxy resins, biphenyl type epoxy resins, and tetramethyl bisphenol F type epoxy resins are preferable, and biphenyl type epoxy resins and tetramethyl bisphenol F type epoxy resins are preferred. Particularly preferred. These compounds may be used independently and may use 2 or more types together.
에폭시 화합물의 함유량은, 특별히 한정되지 않고, 충분한 기계적 강도의 광경화물을 확실히 얻는다는 점에서, 카복실기 함유 감광성 수지 100 질량부에 대해서, 10~150 질량부가 바람직하고, 30~80 질량부가 특히 바람직하다.Content of an epoxy compound is not specifically limited, 10-150 mass parts is preferable with respect to 100 mass parts of carboxyl group-containing photosensitive resin from the point which reliably obtains the photocured material of sufficient mechanical strength, and 30-80 mass parts is especially preferable. Do.
(D) (D) 지방족계Aliphatic 우레아Urea 화합물 compound
카복실기 함유 감광성 수지와 에폭시 화합물을 함유하는 본 발명의 감광성 수지 조성물에 지방족계 우레아 화합물이 배합됨으로써, 감광성 수지 조성물을 1액형으로 해도, 상온(25℃)에서의 보존 중에 카복실기 함유 감광성 수지와 에폭시 화합물과의 반응이 진행되어 버리는 것을 방지하여, 상온에서도 우수한 포트 라이프를 얻을 수 있다. 따라서, 상온에서의 취급 가능 시간을 장기화할 수 있으므로, 본 발명의 감광성 수지 조성물의 도공 작업 등에 있어서의 취급성이 향상된다. 또한, 본 발명의 감광성 수지 조성물에 지방족계 우레아 화합물이 배합됨으로써, 감광성 수지 조성물의 광경화물의 내약품성도 얻을 수도 있다.When an aliphatic urea compound is blended with the photosensitive resin composition of the present invention containing a carboxyl group-containing photosensitive resin and an epoxy compound, the carboxyl group-containing photosensitive resin may be stored at room temperature (25 ° C.) even when the photosensitive resin composition is a one-component type. The reaction with an epoxy compound is prevented from advancing, and the pot life excellent in normal temperature can be obtained. Therefore, since the handleable time at normal temperature can be prolonged, the handleability in coating work etc. of the photosensitive resin composition of this invention improves. Moreover, the chemical-resistance of the photocured material of the photosensitive resin composition can also be obtained by mix | blending an aliphatic urea compound with the photosensitive resin composition of this invention.
지방족계 우레아 화합물은, 그 화학 구조 중에 방향고리를 갖지 않는, 지방족 우레아 화합물이다. 지방족계 우레아 화합물로서는, 하기 일반식(1)An aliphatic urea compound is an aliphatic urea compound which does not have an aromatic ring in the chemical structure. As an aliphatic urea compound, following General formula (1)
[화 2][Tue 2]
(식 중, R1, R2, R3, R4, R5, R6, R7는, 각각, 독립적으로, 탄소수 1~20개의 포화 지방족 탄화수소기, 또는 적어도 1개의 에틸렌성 불포화기를 가지는 탄소수 2~20개의 불포화 지방족 탄화수소기를 의미한다.)로 나타내는 화합물을 들 수 있다.(In formula, R <1> , R <2> , R <3> , R <4> , R <5> , R <6> , R <7> respectively independently has a C1-C20 saturated aliphatic hydrocarbon group or at least 1 ethylenically unsaturated group. And a C2-C20 unsaturated aliphatic hydrocarbon group.
이들 중, 포트 라이프를 한층 더 향상시키는 점에서, R1, R2, R3, R4, R5, R6, R7가, 각각, 독립적으로, 탄소수 1~5개의 포화 지방족 탄화수소기인 일반식(1)의 지방족계 우레아 화합물이 보다 바람직하고, R1, R2, R3, R4, R5, R6, R7가, 각각, 독립적으로, 탄소수 1~3개의 포화 지방족 탄화수소기인 일반식(1)의 지방족계 우레아 화합물이 한층 더 바람직하고, R1, R2, R3, R4, R5, R6, R7가, 모두 메틸기인 일반식(1)의 지방족계 우레아 화합물이 특히 바람직하다. R1, R2, R3, R4, R5, R6, R7가, 모두 메틸기인 일반식(1)의 지방족계 우레아 화합물은, N'-[3-[[[(디메틸아미노)카보닐]아미노]메틸]-3, 5, 5-트리메틸시클로헥실]-N, N-디메틸우레아다.Among these, in general, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 each independently represent a saturated aliphatic hydrocarbon group having 1 to 5 carbon atoms in terms of further improving the pot life. The aliphatic urea compound of formula (1) is more preferable, and R <1> , R <2> , R <3> , R <4> , R <5> , R <6> , R <7> is respectively independently a C1-C3 saturated aliphatic hydrocarbon group. The aliphatic urea compound of the general formula (1) is more preferable, and the aliphatic urea of the general formula (1) in which R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 are all methyl groups Particular preference is given to compounds. The aliphatic urea compound of the general formula (1) wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 are all methyl groups is N '-[3-[[[(dimethylamino) Carbonyl] amino] methyl] -3, 5, 5-trimethylcyclohexyl] -N, N-dimethylurea.
지방족계 우레아 화합물의 함유량은, 특별히 한정되지 않지만, 그 하한값은, 포트 라이프를 한층 더 향상시키는 점에서, 카복실기 함유 감광성 수지 100 질량부에 대해서 5.0 질량부가 바람직하고, 10 질량부가 보다 바람직하고, 15 질량부가 특히 바람직하다. 한편, 지방족계 우레아 화합물의 함유량의 상한값은, 우수한 감도를 확실히 얻는다는 점에서, 카복실기 함유 감광성 수지 100 질량부에 대해서 50 질량부가 바람직하고, 30 질량부가 보다 바람직하고, 25 질량부가 특히 바람직하다.Although content of an aliphatic urea compound is not specifically limited, Since the lower limit further improves a pot life, 5.0 mass parts is preferable with respect to 100 mass parts of carboxyl group-containing photosensitive resin, 10 mass parts is more preferable, 15 mass parts is especially preferable. On the other hand, 50 mass parts is preferable with respect to 100 mass parts of carboxyl group-containing photosensitive resin from the point that the upper limit of content of an aliphatic urea compound ensures the outstanding sensitivity, 30 mass parts is more preferable, 25 mass parts is especially preferable. .
본 발명의 감광성 수지 조성물에서는, 상기 (A) 성분~(D) 성분뿐만 아니라, 필요에 따라, 한층 더 (E) 반응성 희석제를 배합해도 좋다. 반응성 희석제란, 예를 들면, 광중합성 모노머이며, 1분자당 적어도 1개, 바람직하게는 2개 이상의 중합성 이중 결합을 가지는 화합물이다. 반응성 희석제는, 감광성 수지 조성물의 광경화를 충분히 하고, 광경화물의 내산성, 내열성, 내알칼리성 등의 향상에 기여한다.In the photosensitive resin composition of this invention, not only said (A) component-(D) component but you may mix | blend a (E) reactive diluent further as needed. The reactive diluent is, for example, a photopolymerizable monomer and is a compound having at least one, preferably two or more polymerizable double bonds per molecule. The reactive diluent sufficiently cures the photosensitive resin composition and contributes to the improvement of acid resistance, heat resistance, alkali resistance and the like of the photocured product.
반응성 희석제로서는, 예를 들면, 단관능의 (메타)아크릴레이트모노머, 2관능 이상의 (메타)아크릴레이트모노머를 들 수 있다. 구체적인 예로서는, (메타)아크릴산 2-히드록시에틸, 페녹시에틸(메타)아크릴레이트, 디에틸렌글리콜모노(메타)아크릴레이트, 2히드록시3페녹시프로필(메타)아크릴레이트, 카프로락톤변성(메타)아크릴레이트, 1, 4부탄디올디(메타)아크릴레이트, 1, 6헥산디올디(메타)아크릴레이트, 네오펜틸글리콜디(메타)아크릴레이트, 디에틸렌글리콜디(메타)아크릴레이트, 네오펜틸글리콜아디페이트디(메타)아크릴레이트, 히드록시피발산네오펜틸글리콜디(메타)아크릴레이트, 디시클로펜타닐디(메타)아크릴레이트, 에틸렌옥사이드변성인산디(메타)아크릴레이트, 아릴화시클로헥실디(메타)아크릴레이트, 이소시아누레이트디(메타)아크릴레이트, 트리메틸올프로판트리(메타)아크릴레이트, 디트리메틸올프로판테트라(메타)아크릴레이트, 디펜타에리쓰리톨트리(메타)아크릴레이트, 펜타에리쓰리톨트리(메타)아크릴레이트, 프로필렌옥사이드변성트리메틸올프로판트리(메타)아크릴레이트, 트리스(아크릴옥시에틸)이소시아누레이트, 프로피온산변성디펜타에리쓰리톨펜타(메타)아크릴레이트, 디펜타에리쓰리톨헥사(메타)아크릴레이트 등을 들 수 있다. 이들은 단독으로 사용해도 좋고, 2종 이상을 병용해도 좋다.As a reactive diluent, a monofunctional (meth) acrylate monomer and bifunctional or more (meth) acrylate monomer are mentioned, for example. As specific examples, 2-hydroxyethyl (meth) acrylate, phenoxyethyl (meth) acrylate, diethylene glycol mono (meth) acrylate, 2hydroxy3-phenoxypropyl (meth) acrylate, and caprolactone-modified (meth) ) Acrylate, 1, 4 butanediol di (meth) acrylate, 1, 6 hexanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, neopentyl glycol Adipate di (meth) acrylate, hydroxypivalate neopentylglycol di (meth) acrylate, dicyclopentanyldi (meth) acrylate, ethylene oxide modified phosphoric acid di (meth) acrylate, arylated cyclohexyldi ( Meta) acrylate, isocyanurate di (meth) acrylate, trimethylolpropane tri (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, dipentaerythritol Li (meth) acrylate, pentaerythritol tri (meth) acrylate, propylene oxide modified trimethylolpropane tri (meth) acrylate, tris (acryloxyethyl) isocyanurate, propionic acid modified dipentaerythritol penta (Meth) acrylate, dipentaerythritol hexa (meth) acrylate, etc. are mentioned. These may be used independently and may use 2 or more types together.
반응성 희석제의 함유량은, 특별히 한정되지 않지만, 카복실기 함유 감광성 수지 100 질량부에 대해서, 5.0~100 질량부가 바람직하고, 10~50 질량부가 특히 바람직하다.Although content of a reactive diluent is not specifically limited, 5.0-100 mass parts is preferable with respect to 100 mass parts of carboxyl group-containing photosensitive resin, and 10-50 mass parts is especially preferable.
본 발명의 감광성 수지 조성물에는, 상기 (A)~(E) 성분 외에, 한층 더 필요에 따라, 다른 성분, 예를 들면, 각종 첨가제, 착색제, 난연제, 비반응성 희석제 등을, 적절하게 배합해도 좋다.In addition to the above-mentioned (A)-(E) components, you may mix | blend another component, for example, various additives, a coloring agent, a flame retardant, a non-reactive diluent, etc. suitably to the photosensitive resin composition of this invention suitably. .
각종 첨가제에는, 실리콘계, 탄화수소계 및 아크릴계 등의 소포제, 머캅토벤즈옥사졸 및 그 유도체, 디시안디아미드(DICY) 및 그 유도체, 멜라민 및 그 유도체, 삼플루오르화붕소-아민 컴플렉스, 유기산 히드라지드, 디아미노말레오니트릴(DAMN) 및 그 유도체, 구아나민 및 그 유도체, 아민이미드(AI) 및 폴리아민 등의 경화 촉매, 탈크, 황산바륨, 소수성 실리카, 알루미나, 수산화 알루미늄, 마이카 등의 체질 안료 등을 들 수 있다. 경화 촉매를 배합하는 경우, 상기 각종 경화 촉매 중, 감광성 수지 조성물의 광경화물에 염산(HCl) 내성을 보다 확실히 부여하는 점에서 머캅토벤즈옥사졸 및 그 유도체가 바람직하다.Various additives include antifoaming agents such as silicones, hydrocarbons and acrylics, mercaptobenzoxazoles and derivatives thereof, dicyandiamide (DICY) and derivatives thereof, melamine and derivatives thereof, boron trifluoride-amine complex, organic acid hydrazide, Curing catalysts such as diaminomaleonitrile (DAMN) and derivatives thereof, guanamine and derivatives thereof, amineimide (AI) and polyamines, and sieving pigments such as talc, barium sulfate, hydrophobic silica, alumina, aluminum hydroxide, mica, etc. Can be mentioned. When mix | blending a curing catalyst, mercaptobenzoxazole and its derivative (s) are preferable at the point which provides hydrochloric acid (HCl) tolerance more reliably to the photocured material of the photosensitive resin composition among the said various curing catalysts.
착색제는, 안료, 색소 등, 특별히 한정되지 않고, 또한, 백색 착색제, 청색 착색제, 녹색 착색제, 황색 착색제, 자색 착색제, 흑색 착색제, 등색 착색제 등, 어느 색채의 착색제도 사용 가능하다. 상기 착색제에는, 예를 들면, 백색 착색제인 산화 티탄, 흑색 착색제인 카본 블랙 등의 무기계 착색제나, 녹색 착색제인 프탈로시아닌 그린 및 청색 착색제인 프탈로시아닌 블루나 리오놀 블루 등의 프탈로시아닌계, 안트라퀴논계, 등색 착색제인 크로모프탈 오렌지 등의 디케토피롤로피롤계 등의 유기계 착색제 등을 들 수 있다.A coloring agent is not specifically limited, such as a pigment and a pigment | dye, Moreover, coloring agents of any color, such as a white coloring agent, a blue coloring agent, a green coloring agent, a yellow coloring agent, a purple coloring agent, a black coloring agent, and an orange coloring agent, can be used. Examples of the colorant include inorganic colorants such as titanium oxide as a white colorant and carbon black as a black colorant, phthalocyanine based phthalocyanine blue and ionol blue as phthalocyanine green and blue colorant as a green colorant, anthraquinone series, and orange. And organic colorants such as diketopyrrolopyrrole such as chromophthal orange which is a colorant.
난연제는, 본 발명의 감광성 수지 조성물의 광경화물에 난소성을 부여하기 위한 것이다. 난연제로서는, 예를 들면, 인계의 난연제를 들 수 있다. 인계의 난연제로서는, 예를 들면, 트리스(클로로에틸)포스페이트, 트리스(2, 3-디클로로프로필)포스페이트, 트리스(2-클로로프로필)포스페이트, 트리스(2, 3-브로모프로필)포스페이트, 트리스(브로모클로로프로필)포스페이트, 2, 3-디브로모프로필-2, 3-클로로프로필포스페이트, 트리스(트리브로모페닐)포스페이트, 트리스(디브로모페닐)포스페이트, 트리스(트리브로모네오펜틸)포스페이트 등의 함할로겐계인산에스테르; 트리메틸포스페이트, 트리에틸포스페이트, 트리부틸포스페이트, 트리옥틸포스페이트, 트리부톡시에틸포스페이트 등의 비할로겐계 지방족 인산 에스테르; 트리페닐포스페이트, 크레질디페닐포스페이트, 디크레질페닐포스페이트, 트리크레질포스페이트, 트리크실레닐포스페이트, 크실레닐디페닐포스페이트, 트리스(이소프로필페닐)포스페이트, 이소프로필페닐디페닐포스페이트, 디이소프로필페닐페닐포스페이트, 트리스(트리메틸 페닐)포스페이트, 트리스(t-부틸페닐)포스페이트, 히드록시페닐디페닐포스페이트, 옥틸디페닐포스페이트 등의 비할로겐계 방향족 인산 에스테르; 트리스디에틸포스핀산알루미늄, 트리스메틸에틸포스핀산알루미늄, 트리스디페닐포스핀산알루미늄, 비스디에틸포스핀산아연, 비스메틸에틸포스핀산아연, 비스디페닐포스핀산아연, 비스디에틸포스핀산티타닐, 테트라키스디에틸포스핀산티탄, 비스메틸에틸포스핀산티타닐, 테트라키스메틸에틸포스핀산티탄, 비스디페닐포스핀산티타닐, 테트라키스디페닐포스핀산티탄 등의 포스핀산의 금속염, 9, 10-디히드로-9-옥사-10-포스파페난트렌-10-옥사이드(이하 HCA), HCA와 아크릴산 에스테르의 부가 반응 생성물, HCA와 에폭시 수지의 부가 반응 생성물, HCA와 하이드로퀴논의 부가 반응 생성물 등의 HCA 변성형 화합물, 디페닐비닐포스핀옥사이드, 트리페닐포스핀옥사이드, 트리알킬포스핀옥사이드, 트리스(히드록시알킬)포스핀옥사이드 등의 포스핀옥사이드계 화합물 등을 들 수 있다. 이 중, 유기 인산염계의 난연제가 바람직하다. 이들은, 단독으로 사용해도 좋고, 2종 이상을 병용해도 좋다.The flame retardant is for imparting flame resistance to the photocured product of the photosensitive resin composition of the present invention. As a flame retardant, a phosphorus flame retardant is mentioned, for example. Examples of the phosphorus flame retardant include tris (chloroethyl) phosphate, tris (2,3-dichloropropyl) phosphate, tris (2-chloropropyl) phosphate, tris (2,3-bromopropyl) phosphate and tris ( Bromochloropropyl) phosphate, 2, 3-dibromopropyl-2, 3-chloropropylphosphate, tris (tribromophenyl) phosphate, tris (dibromophenyl) phosphate, tris (tribromoneopentyl) Halogen-containing phosphate esters such as phosphate; Non-halogen aliphatic phosphate esters such as trimethyl phosphate, triethyl phosphate, tributyl phosphate, trioctyl phosphate and tributoxyethyl phosphate; Triphenyl phosphate, cresyl diphenyl phosphate, dicrezyl phenyl phosphate, tricresyl phosphate, trixenyl phosphate, xylenyl diphenyl phosphate, tris (isopropylphenyl) phosphate, isopropyl phenyl diphenyl phosphate, diisopropyl Non-halogen aromatic phosphate esters such as phenylphenylphosphate, tris (trimethyl phenyl) phosphate, tris (t-butylphenyl) phosphate, hydroxyphenyldiphenylphosphate and octyldiphenylphosphate; Aluminum tris diethyl phosphate, aluminum tris methyl ethyl phosphate, aluminum tris diphenyl phosphate, zinc bis diethyl phosphate, zinc bis methyl ethyl phosphate, zinc bis diphenyl phosphate, titanium bis diethyl phosphate, Metal salts of phosphinic acids, such as titanium tetrakis diethyl phosphinate, titanium bismethyl ethyl phosphine titanate, titanium tetrakismethyl ethyl phosphine titanate, titanium bis diphenyl phosphine titanate, and titanium tetrakis diphenyl phosphinate, 9, 10- Dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (hereinafter HCA), addition reaction product of HCA and acrylic acid ester, addition reaction product of HCA and epoxy resin, addition reaction product of HCA and hydroquinone Phosphine oxides such as HCA modified compounds, diphenylvinylphosphine oxide, triphenylphosphine oxide, trialkylphosphine oxide, and tris (hydroxyalkyl) phosphine oxide There may be mentioned compounds and the like. Among these, an organic phosphate flame retardant is preferable. These may be used independently and may use 2 or more types together.
비반응성 희석제는, 감광성 수지 조성물의 도공성이나 건조성을 조절하기 위한 것이다. 비반응성 희석제로서, 예를 들면, 유기용제를 들 수 있다. 유기용제에는, 예를 들면, 메틸에틸케톤, 시클로 헥산 등의 케톤류, 톨루엔, 크실렌 등의 방향족 탄화수소류, 메탄올, 이소프로판올, 시클로헥산올 등의 알코올류, 시클로헥산, 메틸시클로헥산 등의 지환식 탄화수소류, 석유 에테르, 석유 나프타 등의 석유계 용제, 셀로솔브, 부틸셀로솔브 등의 셀로솔브류, 카르비톨, 부틸카르비톨 등의 카르비톨류, 아세트산에틸, 아세트산부틸, 셀로솔브아세테이트, 부틸셀로솔브아세테이트, 카르비톨아세테이트, 부틸카르비톨아세테이트, 에틸렌글리콜아세테이트, 에틸디글리콜아세테이트 등의 에스테르류 등을 들 수 있다. 이들은, 단독으로 사용해도 좋고, 2종 이상을 병용해도 좋다.A non-reactive diluent is for adjusting the coating property and drying property of the photosensitive resin composition. As a non-reactive diluent, an organic solvent is mentioned, for example. In the organic solvent, for example, ketones such as methyl ethyl ketone and cyclohexane, aromatic hydrocarbons such as toluene and xylene, alcohols such as methanol, isopropanol and cyclohexanol, and alicyclic hydrocarbons such as cyclohexane and methylcyclohexane , Petroleum solvents such as petroleum ether, petroleum naphtha, cellosolves such as cellosolve and butyl cellosolve, carbitols such as carbitol and butyl carbitol, ethyl acetate, butyl acetate, cellosolve acetate and butyl cell Esters such as rosolve acetate, carbitol acetate, butyl carbitol acetate, ethylene glycol acetate, ethyl diglycol acetate, and the like. These may be used independently and may use 2 or more types together.
상기 본 발명의 감광성 수지 조성물의 제조 방법은, 특정 방법으로 한정되지 않고, 예를 들면, 상기 각 성분을 소정 비율로 배합 후, 실온(상온)에서, 삼본롤, 볼밀, 샌드밀 등의 혼련 수단, 또는 슈퍼 믹서, 플래니터리 믹서 등의 교반 수단에 의해 혼련 또는 혼합해 제조할 수 있다. 또한, 상기 혼련 또는 혼합 전에, 필요에 따라, 실온(상온)에서, 예비 혼련 또는 예비 혼합해도 좋다.The manufacturing method of the photosensitive resin composition of the said invention is not limited to a specific method, For example, after mix | blending each said component in a predetermined ratio, kneading | mixing means, such as a three bone roll, a ball mill, a sand mill, at room temperature (room temperature) Alternatively, the mixture may be kneaded or mixed by a stirring means such as a super mixer or planetary mixer to produce the same. In addition, before kneading or mixing, preliminary kneading or premixing may be performed at room temperature (room temperature) as necessary.
이어서, 상기 본 발명의 감광성 수지 조성물의 사용 방법예에 대해 설명한다. 여기에서는, 동박을 에칭해 형성한 회로 패턴을 가지는 프린트 배선판 상에, 본 발명의 감광성 수지 조성물을 도공한 드라이 필름을 이용하여, 솔더 레지스트막을 형성하는 방법을 예를 들어 설명한다.Next, the usage example of the photosensitive resin composition of the said invention is demonstrated. Here, the method of forming a soldering resist film is demonstrated using the dry film which coated the photosensitive resin composition of this invention on the printed wiring board which has the circuit pattern which etched and formed copper foil, for example.
드라이 필름은, 지지 필름(예를 들면, 폴리에틸렌테레프탈레이트 필름, 폴리에스테르 필름 등의 열가소성 필름)과, 상기 지지 필름에 도공된 솔더 레지스트층과, 상기 솔더 레지스트층을 보호하는 커버 필름(예를 들면, 폴리에틸렌 필름, 폴리프로필렌 필름)을 가지는 적층 구조로 되어 있다. 지지 필름 상에 본 발명의 감광성 수지 조성물을, 롤러 코트법, 바코터법 등의 공지의 방법으로 도공해 도막을 형성 후, 상기 도막을 건조 처리함으로써, 지지 필름 상에 솔더 레지스트층을 형성한다. 그 후, 형성한 솔더 레지스트층 상에 커버 필름을 적층함으로써 드라이 필름을 제작할 수 있다.A dry film is a support film (for example, thermoplastic films, such as a polyethylene terephthalate film and a polyester film), the soldering resist layer coated on the said support film, and the cover film which protects the said soldering resist layer (for example , Polyethylene film, polypropylene film). After coating the photosensitive resin composition of this invention on a support film by well-known methods, such as a roller coat method and a bar coater method, and forming a coating film, the said coating film is dried and a solder resist layer is formed on a support film. Thereafter, a dry film can be produced by laminating a cover film on the formed solder resist layer.
상기 드라이 필름의 커버 필름을 벗기면서 솔더 레지스트층과 프린트 배선판을 맞붙임으로써, 프린트 배선판 상에 솔더 레지스트막을 형성한다. 그 후, 필요에 따라, 감광성 수지 조성물 중의 비반응성 희석제(유기용제)를 휘산시키기 위해서 100~120℃ 정도의 온도로 1~10분간 정도 가열하는 예비 건조를 실시하여, 감광성 수지 조성물로부터 비반응성 희석제(유기용제)를 휘발시켜 솔더 레지스트막의 표면을 택프리 상태로 한다. 형성한 솔더 레지스트막 상에, 회로 패턴의 랜드 이외를 투광성으로 한 패턴을 가지는 네거티브 필름을 밀착시켜, 그 위에서부터 자외선(예를 들면, 파장 300~400nm의 범위)을 조사시킨다. 그 후, 상기 랜드에 대응하는 비노광 영역을 희알칼리 수용액으로 제거함으로써 솔더 레지스트막이 현상된다. 현상 방법에는, 스프레이법, 샤워법 등이 이용되고, 사용되는 희알칼리 수용액으로서는, 예를 들면, 0.5~5 질량%의 탄산나트륨 수용액을 들 수 있다. 현상 후, 130~170℃의 열풍 순환식 건조기 등으로 20~80분간 포스트 큐어를 실시함으로써, 프린트 배선판 상에, 목적으로 하는 패턴을 가지는 솔더 레지스트막을 형성시킬 수 있다.A soldering resist film is formed on a printed wiring board by bonding a soldering resist layer and a printed wiring board, peeling off the cover film of the said dry film. Then, as needed, in order to volatilize the non-reactive diluent (organic solvent) in the photosensitive resin composition, predrying is performed for about 1 to 10 minutes at the temperature of about 100-120 degreeC, and a non-reactive diluent from the photosensitive resin composition is carried out. The (organic solvent) is volatilized to bring the surface of the solder resist film into a tack free state. On the formed soldering resist film, the negative film which has a pattern which made light transmissive other than the land of a circuit pattern adheres, and irradiates an ultraviolet-ray (for example, the range of wavelength 300-400nm) from the top. Thereafter, the solder resist film is developed by removing the non-exposed areas corresponding to the lands with the aqueous alkali solution. The spray method, the shower method, etc. are used for the image development method, As a rare alkali aqueous solution used, 0.5-5 mass% sodium carbonate aqueous solution is mentioned, for example. After image development, a 20-80 minute postcure is performed by 130-170 degreeC hot-air circulation type dryer, etc., and the soldering resist film which has a target pattern can be formed on a printed wiring board.
[[ 실시예Example ]]
이어서, 본 발명의 실시예를 설명하지만, 본 발명은 그 취지를 벗어나지 않는 한 이들 예로 한정되는 것은 아니다.Next, although the Example of this invention is described, this invention is not limited to these examples, unless the meaning is exceeded.
실시예 1~5, 비교예 1~6Examples 1-5, Comparative Examples 1-6
하기 표 1에 나타낸 각 성분을 하기 표 1에 나타낸 배합 비율로 배합하고, 삼본롤을 이용해 실온(25℃)에서 혼합 분산시키고, 실시예 1~5, 비교예 1~6에서 사용하는 감광성 수지 조성물을 제조했다. 하기 표 1에 나타낸 각 성분의 배합량은, 특별히 다른 기재가 없는 한 질량부를 나타낸다. 또한, 하기 표 1의 배합량의 공란부는, 배합 없음을 의미한다.Each component shown in following Table 1 is mix | blended in the compounding ratio shown in following Table 1, it mixes and disperse | distributes at room temperature (25 degreeC) using a three bone roll, and is used in Examples 1-5 and Comparative Examples 1-6. Prepared. The compounding quantity of each component shown in following Table 1 shows a mass part unless there is particular notice. In addition, the blank part of the compounding quantity of following Table 1 means no compounding.
또한, 하기 표 1의 각 성분에 대한 자세한 내용은, 이하와 같다.In addition, the detail about each component of following Table 1 is as follows.
(A) 카복실기 함유 감광성 수지(A) carboxyl group-containing photosensitive resin
· KAYARAD ZAR-2000: 고형분(수지분) 65 질량%, 니혼카야쿠(주)KAYARAD ZAR-2000: 65 mass% of solids (resin), Nihon Kayaku Co., Ltd.
또한, KAYARAD ZAR-2000은, 에폭시 수지(비스페놀 A형 에폭시 수지)의 에폭시기 중 적어도 일부에, 아크릴산을 반응시키고, 에폭시아크릴레이트를 얻고, 에폭시아크릴레이트를 생성한 수산기에 다염기산을 반응시켜 얻을 수 있는, 다염기산 변성 에폭시아크릴레이트 수지다.In addition, KAYARAD ZAR-2000 can be obtained by reacting at least part of an epoxy group of an epoxy resin (bisphenol-A epoxy resin) with acrylic acid, obtaining an epoxy acrylate, and reacting a polybasic acid with a hydroxyl group which has produced an epoxy acrylate. And polybasic acid-modified epoxy acrylate resins.
(B) 광중합 개시제(B) photoinitiator
· IRGACURE369: 치바스페셜티케미컬즈(주)IRGACURE369: Chiba Specialty Chemicals
· EAB: 호도가야카가쿠코교(주)EAB: Hodogaya Kagaku Kogyo Co., Ltd.
· IRGACURE OXE02: 치바스페셜티케미컬즈(주)IRGACURE OXE02: Chiba Specialty Chemicals
(C) 에폭시 화합물(C) epoxy compound
· NC-3000: 니혼카야쿠(주)NC-3000: Nihon Kayaku Co., Ltd.
· 에피클론 860, 에피클론 N-695: DIC(주)Epiclone 860, Epiclone N-695: DIC Corporation
· YX-4000HK: 미츠비시카가쿠(주)YX-4000HK: Mitsubishi Kagaku Co., Ltd.
· YSLV-80XY: 신닛테츠스미킨카가쿠(주)YSLV-80XY: Shinnitetsu Sumikinkagaku Co., Ltd.
(E) 반응성 희석제(E) reactive diluent
· DPCA-120: 니혼카야쿠(주)DPCA-120: Nihon Kayaku Co., Ltd.
경화 촉매Curing catalyst
· 디시안디아미드: 도쿄카세이코교(주)Dicyandiamide: Tokyo Kasei Co., Ltd.
· 멜라민: 도쿄카세이코교(주)Melamine: Tokyo Kasei Co., Ltd.
· 2-머캅토벤즈옥사졸: 도쿄카세이코교(주)2-mercaptobenzoxazole: Tokyo Kasei Co., Ltd.
난연제Flame retardant
· 엑솔릿트 OP-935: 클라리언트재팬(주)Excellent OP-935: Clariant Japan Co., Ltd.
착색제coloring agent
· 크로모프탈 DPP 오렌지 TR: 치바스페셜티케미컬즈(주)Chromophthal DPP Orange TR: Chivas Specialty Chemicals
· 리오놀 블루-FG-7351: 토요잉크세이조(주)LIONOL BLUE-FG-7351: TOYO Ink Seizo Co., Ltd.
소포제Antifoam
· KS-66: 신에츠카가쿠코교(주)KS-66: Shin-Etsukagaku Kogyo Co., Ltd.
비반응성 희석제Non-reactive diluent
· EDGAC: 산요카세힝(주)EDGAC: Sanyo Kaseching Co., Ltd.
시험편 제작 공정Test piece making process
도포 기판: 폴리에틸렌테레프탈레이트 필름(PET 필름)Coating substrate: Polyethylene terephthalate film (PET film)
도공법: 바코터Coating Method: Bar Coater
예비 건조: 110℃, 5분Predrying: 110 ° C., 5 minutes
평가 기판: 2층 동장 적층판(CCL)(폴리이미드(두께 25μm) 기판, 동박(두께 12.5μm))Evaluation board | substrate: 2-layer copper clad laminated board (CCL) (polyimide (25 micrometers in thickness) board | substrate, copper foil (12.5 micrometers in thickness))
표면 처리: 5 질량% 황산 처리Surface treatment: 5% by mass sulfuric acid treatment
라미네이트 조건: 50℃, 가압 50MPa, 진공 30초/가압 30초Lamination conditions: 50 ° C, pressurized 50MPa, vacuum 30 seconds / pressurized 30 seconds
DRY 막두께: 25μmDRY film thickness: 25μm
노광: 도막 상에 150mJ/cm2, USHIO(주)제 투영 노광 장치(광원은 고압 수은등)Exposure: 150mJ / cm 2 on a coating film, the projection exposure apparatus made by USHIO Co., Ltd. (the light source is a high pressure mercury lamp)
현상: 1 질량% 탄산나트륨 수용액 온도 30℃, 스프레이압 0.2MPa, 현상 시간 60초Developing: 1 mass% sodium carbonate aqueous solution temperature 30 ℃, spray pressure 0.2MPa, developing time 60 seconds
포스트 큐어: 150℃, 60분Post Cure: 150 ℃, 60 minutes
평가 항목Evaluation item
(1) 포트 라이프(pot life)(1) pot life
상기와 같이 제조한 감광성 수지 조성물을 도포 기판인 PET 필름에 도공해 도막을 형성 후, 도포 기판을 예비 건조한 후 25℃에 방치했다. 25℃에 방치한 도포 기판을 24시간마다 꺼내, 평가 기판인 2층 CCL에 라미네이트 후, 노광을 하지 않고 현상을 실시했다. 현상 개시부터 도막 바탕의 동박이 보일 때까지의 시간을 계측했다. 현상 개시부터 도막 바탕의 동박이 보일 때까지의 시간이 30초 이내를 ○, 현상 개시부터 도막 바탕의 동박이 보일 때까지의 시간이 30초 초과를 ×라고 평가하고, 72시간 방치 이상을 ○로 평가, 합격으로 했다. 또한, 표 1에는, ○ 평가를 유지할 수 있던 최대 방치 시간을 기재해, 24시간 방치에서 × 평가인 경우에는, 「24시간 ×」라고 표기했다.After apply | coating the photosensitive resin composition manufactured as mentioned above to PET film which is an application | coating board | substrate, and forming a coating film, the application | coating board | substrate was left to stand at 25 degreeC after preliminary drying. The coated substrate left at 25 ° C. was taken out every 24 hours and developed without exposure after lamination on a two-layer CCL that is an evaluation substrate. The time from the start of development until the copper foil of the coating film base was seen was measured. The time from the start of development until the copper foil of a coating film base is seen in ○, and the time from the start of development until the copper foil of a coating film base is seen evaluates more than 30 second as X, and leave more than 72 hours to ○ Evaluation was made. In addition, in Table 1, the maximum leaving time which was able to hold (circle) evaluation was described, and when it was x evaluation in leaving for 24 hours, it described as "24 hours x."
(2) 감도(2) sensitivity
도포 기판의 도막 상에 감도 측정용 스텝 타블렛(Stouffer 21단)을 설치해, 감도 측정용 스텝 타블렛을 통해, 파장의 메인 피크가 365nm인 자외선을, 150mJ/cm2 조사한 것을 테스트 피스로 했다. 자외선의 조사 광량은, 오크세이사쿠쇼(주)제 적산 광량계를 이용해 측정했다. 자외선을 노광 후, 상기 시험편 제작 공정에 준하여 현상을 실시해, 노광 부분이 제거되지 않는 부분을 숫자(스텝 수)로 나타냈다. 스텝 수가 클수록 감도가 양호한 것을 나타낸다.The step tablet (Stouffer 21 steps) for sensitivity measurement was provided on the coating film of an application board | substrate, and 150 mJ / cm <2> irradiated the ultraviolet-ray whose main peak of wavelength is 365 nm was made into the test piece through the step tablet for sensitivity measurement. The irradiation light quantity of the ultraviolet-ray was measured using the integrated photometer made by Oak Seisakusho Corporation. After exposure to ultraviolet rays, development was carried out in accordance with the test piece preparation step, and portions where the exposed portions were not removed were represented by numbers (number of steps). The larger the number of steps, the better the sensitivity.
(3) 염산(HCl) 내성(3) hydrochloric acid (HCl) resistance
상기 시험편 제작 공정으로 얻은 시험편을 10 질량%의 HCl 수용액에 상온으로 30분간 침지하고, 침지 후, 충분히 수세를 실시하고, 부드러운 천으로 수분을 제거했다. 그 후, 도막 표면을 200배의 광학 현미경으로 관찰하고, 도막의 박리(들뜸) 의 상황을 하기 3단계로 평가하고, ○평가를 합격으로 했다.The test piece obtained by the said test piece preparation process was immersed in 10 mass% HCl aqueous solution at room temperature for 30 minutes, and after immersion, it washed with water sufficiently and removed water with the soft cloth. Then, the coating film surface was observed with the optical microscope of 200 times, the situation of peeling (lifting) of the coating film was evaluated in the following three steps, and (circle) evaluation was made into the pass.
○ : 박리 (들뜸)의 발생 없음○: no occurrence of peeling (lifting)
△ : 약간의 박리(들뜸) 있음△: slight peeling off
× : 큰 박리(들뜸) 있음×: Large peeling off
(4) 이소프로필알코올(IPA) 내성(4) isopropyl alcohol (IPA) resistance
상기 시험편 제작 공정으로 얻은 시험편을 10 질량%의 이소프로필알코올(IPA) 수용액에 상온에서 30분간 침지하고, 침지 후, 충분히 수세를 실시하고, 부드러운 천으로 수분을 제거했다. 그 후, 도막 표면을 200배의 광학 현미경으로 관찰하고, 도막의 박리(들뜸) 상황을, 하기 3단계로 평가하고, ○ 평가를 합격으로 했다.The test piece obtained by the said test piece preparation process was immersed in 10 mass% isopropyl alcohol (IPA) aqueous solution for 30 minutes at normal temperature, and after immersion, it washed with water sufficiently and removed water with the soft cloth. Then, the coating film surface was observed with the optical microscope of 200 times, the peeling (lifting) condition of the coating film was evaluated in the following three steps, and (circle) evaluation was made into the pass.
○: 박리(들뜸)의 발생 없음○: no occurrence of peeling
△: 약간의 박리(들뜸) 있음△: slight peeling off
×: 큰 박리(들뜸) 있음X: There is a large peeling (lifting)
평가 결과를, 하기 표 1에 나타낸다.The evaluation results are shown in Table 1 below.
09.0
0
(D) aliphatic urea compounds
Evaluation results
간○96 o'clock
Liver ○
간○144 o'clock
Liver ○
간○192 h
Liver ○
간○72 o'clock
Liver ○
간○336 o'clock
Liver ○
간×24 hours
Liver ×
간○72 o'clock
Liver ○
간○72 o'clock
Liver ○
간×24 hours
Liver ×
간×48 o'clock
Liver ×
간×48 o'clock
Liver ×
상기 표 1에 나타낸 바와 같이, 지방족계 우레아 화합물인 N'-[3-[[[(디메틸아미노)카보닐]아미노]메틸]-3, 5, 5-트리메틸시클로헥실]-N, N-디메틸우레아를 배합한 실시예 1~5에서는, 감도를 해치지 않고, 포트 라이프 시험에 대해 72시간 이상에서 ○ 평가로, 상온 시에 있어서의 우수한 포트 라이프를 얻을 수 있었다. 특히, 실시예 3, 5로부터, 에폭시 화합물로서, 비페닐형 에폭시 수지, 테트라메틸비스페놀 F형 에폭시 수지를 사용하면, 192시간 이상에서 ○평가로, 상온 시에 있어서 특별히 우수한 포트 라이프를 얻을 수 있었다.As shown in Table 1, N '-[3-[[[(dimethylamino) carbonyl] amino] methyl] -3, 5, 5-trimethylcyclohexyl] -N, N-dimethyl, which is an aliphatic urea compound In Examples 1-5 which mix | blended urea, the outstanding pot life at the time of normal temperature was obtained by (circle) evaluation for 72 hours or more about a pot life test, without impairing a sensitivity. In particular, when Examples 3 and 5 used biphenyl type epoxy resin and tetramethyl bisphenol F type epoxy resin as an epoxy compound, it was able to obtain the pot life which was especially excellent in normal temperature at the time of 192 hours or more by evaluation. .
또한, 실시예 1~5에서는, HCl 내성과 IPA 내성에도 우수하고, 산과 알코올에 대해서 내성이 우수했다. 따라서, 실시예 1~5에서는, 내약품성에도 우수한 것으로 판명되었다.Moreover, in Examples 1-5, it was excellent also in HCl tolerance and IPA tolerance, and was excellent in resistance to acid and alcohol. Therefore, in Examples 1-5, it turned out that it is excellent also in chemical-resistance.
한편, 에폭시 수지로서 비페닐아랄킬형 에폭시 수지를 사용하고, 지방족계 우레아 화합물을 대신해 방향족계 디메틸우레아 화합물을 배합한 비교예 1에서는, 양호한 포트 라이프, HCl 내성, IPA 내성은 얻을 수 없었다. 또한, 에폭시 수지로서 비스페놀 A형 에폭시 수지, 비페닐형 에폭시 수지를 사용하고, 지방족계 우레아 화합물을 대신해 방향족계 디메틸우레아 화합물을 배합한 비교예 2, 3에서는, HCl 내성, IPA 내성을 얻을 수 없었다.On the other hand, in Comparative Example 1 in which a biphenyl aralkyl type epoxy resin was used as the epoxy resin and an aromatic dimethyl urea compound was incorporated in place of the aliphatic urea compound, good pot life, HCl resistance, and IPA resistance could not be obtained. In addition, in Comparative Examples 2 and 3 in which a bisphenol-A epoxy resin and a biphenyl-type epoxy resin were used as the epoxy resin and an aromatic dimethyl urea compound was incorporated in place of the aliphatic urea compound, HCl resistance and IPA resistance could not be obtained. .
또한, 지방족계 우레아 화합물을 배합하지 않은 비교예 4~6에서는, 양호한 포트 라이프를 얻을 수 없었다.Moreover, in Comparative Examples 4-6 which do not mix | blend an aliphatic urea compound, favorable pot life was not acquired.
본 발명의 감광성 수지 조성물은, 내약품성이 있으면서 1액형으로 조성해도, 상온에서의 보존 중에 카복실기 함유 감광성 수지와 에폭시 화합물과의 반응이 진행되어 버리는 것을 방지하여, 긴 포트 라이프를 가진다. 따라서, 본 발명의 감광성 수지 조성물은, 감광성 수지 조성물의 제조 후, 상온에서의 취급 시간을 장기화할 수 있으므로, 도공 작업 등에 있어서의 취급성이 향상된다. 상기로부터, 예를 들면, 프린트 배선판에 형성하는 솔더 레지스트 등의 보호막의 분야, 특히, 감광성 수지 조성물을 필름에 도포한 도막을 가지는 드라이 필름을 프린트 배선판에 적용해 솔더 레지스트 등의 보호막을 프린트 배선판에 형성하는 분야에서 이용가치가 높다.The photosensitive resin composition of this invention prevents reaction of a carboxyl group-containing photosensitive resin and an epoxy compound from advancing during storage at normal temperature, and has long pot life, even if it is made into 1-pack type while having chemical resistance. Therefore, since the photosensitive resin composition of this invention can prolong the handling time at normal temperature after manufacture of the photosensitive resin composition, the handleability in coating work etc. improves. From the above, for example, a protective film such as solder resist is applied to a printed wiring board by applying a dry film having a coating film coated with a photosensitive resin composition to a film, in particular, a protective film such as a solder resist formed on a printed wiring board. High value in the field of forming.
Claims (10)
The photosensitive resin composition containing (A) carboxyl group-containing photosensitive resin, (B) photoinitiator, (C) epoxy compound, and (D) aliphatic urea compound.
[화 1]
(식 중, R1, R2, R3, R4, R5, R6, R7는, 각각, 독립적으로, 탄소수 1~20개의 포화 지방족 탄화수소기, 또는 적어도 1개의 에틸렌성 불포화기를 가지는 탄소수 2~20개의 불포화 지방족 탄화수소기를 의미한다.)로 나타내는 화합물인 것을 특징으로 하는 감광성 수지 조성물.
The said (D) aliphatic urea compound is a following General formula (1) of Claim 1
[Tue 1]
(In formula, R <1> , R <2> , R <3> , R <4> , R <5> , R <6> , R <7> respectively independently has a C1-C20 saturated aliphatic hydrocarbon group or at least 1 ethylenically unsaturated group. It means a C2-C20 unsaturated aliphatic hydrocarbon group.) Photosensitive resin composition characterized by the above-mentioned.
The said photosensitive resin composition of Claim 2 whose R <1> , R <2> , R <3> , R <4> , R <5> , R <6> , R <7> is a C1-C5 saturated aliphatic hydrocarbon group each independently.
The said photosensitive resin composition of Claim 2 or 3 whose R <1> , R <2> , R <3> , R <4> , R <5> , R <6> , R <7> is a methyl group, respectively.
The said (D) aliphatic urea compound is contained in 10 mass parts or more and 30 mass parts or less with respect to 100 mass parts of said (A) carboxyl group-containing photosensitive resin, The said any one of Claims 1-4. Photosensitive resin composition to be.
The photosensitive resin composition according to any one of claims 1 to 5, further comprising (E) a reactive diluent.
The photosensitive resin composition according to any one of claims 1 to 6, further comprising a mercaptobenzoxazole and / or a mercaptobenzoxazole derivative.
The photocured product of the photosensitive resin composition of any one of Claims 1-7.
The dry film containing the photosensitive resin composition of any one of Claims 1-7.
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| US5281678A (en) * | 1990-11-20 | 1994-01-25 | W. R. Grace & Co. | Preparation of unsaturated epoxy ester resin and carboxylated unsaturated epoxy ester resin and photosensitive composition comprising the same |
| JP2007079120A (en) * | 2005-09-14 | 2007-03-29 | Fujifilm Corp | Photosensitive composition, pattern forming material, photosensitive laminate, pattern forming apparatus, and pattern forming method |
| TW201035680A (en) * | 2008-12-25 | 2010-10-01 | Ajinomoto Kk | Photosensitive resin composition |
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| EP2880072B1 (en) * | 2012-08-02 | 2016-09-07 | AlzChem AG | Liquid hardeners for hardening epoxide resins (ii) |
| CN106556969A (en) * | 2015-09-29 | 2017-04-05 | 株式会社田村制作所 | Photosensitive polymer combination |
| JP6832071B2 (en) * | 2016-03-25 | 2021-02-24 | 東京応化工業株式会社 | A method for producing a colored photosensitive composition, a colored cured product obtained thereby, a display element, and a colored cured product. |
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