JPWO2013141014A1 - 新規化合物及び感光性樹脂組成物 - Google Patents
新規化合物及び感光性樹脂組成物 Download PDFInfo
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- JPWO2013141014A1 JPWO2013141014A1 JP2014506122A JP2014506122A JPWO2013141014A1 JP WO2013141014 A1 JPWO2013141014 A1 JP WO2013141014A1 JP 2014506122 A JP2014506122 A JP 2014506122A JP 2014506122 A JP2014506122 A JP 2014506122A JP WO2013141014 A1 JPWO2013141014 A1 JP WO2013141014A1
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- 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 1
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- UCNNJGDEJXIUCC-UHFFFAOYSA-L hydroxy(oxo)iron;iron Chemical compound [Fe].O[Fe]=O.O[Fe]=O UCNNJGDEJXIUCC-UHFFFAOYSA-L 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
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- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
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- 239000012046 mixed solvent Substances 0.000 description 1
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- JAYXSROKFZAHRQ-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC=CC=1)CC1CO1 JAYXSROKFZAHRQ-UHFFFAOYSA-N 0.000 description 1
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- QHCCDDQKNUYGNC-UHFFFAOYSA-N n-ethylbutan-1-amine Chemical compound CCCCNCC QHCCDDQKNUYGNC-UHFFFAOYSA-N 0.000 description 1
- CXXISLZOPXKTTK-UHFFFAOYSA-N n-methyl-4-[[4-[methyl(oxiran-2-ylmethyl)amino]phenyl]methyl]-n-(oxiran-2-ylmethyl)aniline Chemical compound C=1C=C(CC=2C=CC(=CC=2)N(C)CC2OC2)C=CC=1N(C)CC1CO1 CXXISLZOPXKTTK-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- MZYHMUONCNKCHE-UHFFFAOYSA-N naphthalene-1,2,3,4-tetracarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=C(C(O)=O)C(C(O)=O)=C21 MZYHMUONCNKCHE-UHFFFAOYSA-N 0.000 description 1
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
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- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 239000005011 phenolic resin Substances 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- VUNPWIPIOOMCPT-UHFFFAOYSA-N piperidin-3-ylmethanol Chemical compound OCC1CCCNC1 VUNPWIPIOOMCPT-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920005670 poly(ethylene-vinyl chloride) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 229960000380 propiolactone Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003346 selenoethers Chemical class 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
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- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
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- 239000003381 stabilizer Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000004763 sulfides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003505 terpenes Chemical class 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
- 238000012360 testing method Methods 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000001017 thiazole dye Substances 0.000 description 1
- 150000003553 thiiranes Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
- 229940103494 thiosalicylic acid Drugs 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 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
- 238000012546 transfer Methods 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 239000001003 triarylmethane dye Substances 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
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- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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Abstract
Description
R2及びR3は、それぞれ独立に、水素原子、無置換若しくは置換基を有している炭素原子数1〜20の脂肪族炭化水素基又はフェニル基であるか、R2及びR3が、互いに連結して形成する窒素原子及び炭素原子からなる環であり、
R4は、無置換若しくは置換基を有している炭素原子数1〜20の脂肪族炭化水素基、無置換若しくは置換基を有している炭素原子数6〜20の芳香族炭化水素基又は無置換若しくは置換基を有している炭素原子数2〜20の複素環基を表し、
R5、R6、R7、R8、R9、R10及びR11は、それぞれ独立に、水素原子、シアノ基、ニトロ基、−OR12、−COOR12、−CO−R12、−SR12、ハロゲン原子、無置換若しくは置換基を有している炭素原子数1〜20の脂肪族炭化水素基、無置換若しくは置換基を有している炭素原子数6〜20の芳香族炭化水素基又は無置換若しくは置換基を有している炭素原子数2〜20の複素環基を表し、R12は、無置換若しくは置換基を有している炭素原子数1〜20の脂肪族炭化水素基、無置換若しくは置換基を有している炭素原子数6〜20の芳香族炭化水素基又は無置換若しくは置換基を有している炭素原子数2〜20の複素環基を表し、nは、0又は1を表す。)
また、本発明は、上記感光性樹脂組成物にエネルギー線を照射してなる硬化物を提供するものである。
本発明の新規化合物は、上記一般式(1)で表されるものである。該オキシムエステル化合物には、オキシムの二重結合による幾何異性体が存在するが、これらを区別するものではない。
即ち、本明細書において、上記一般式(1)で表される化合物、並びに後述する該化合物の好ましい形態である化合物及び例示化合物は両方の混合物又はどちらか一方を表すものであり、異性体を示した構造に限定するものではない。
尚、一般式(1)中のR1〜R12で表される基が、炭素原子を含む基により中断又は置換されている場合、それらの炭素原子数を含めた数が規定の炭素原子数となる。
R及びR’は、無置換の脂肪族炭化水素基であり、無置換の脂肪族炭化水素基としては、上記のR1で表される無置換の炭素原子数1〜20の脂肪族炭化水素基として例示したものと同様の基が挙げられる。
上記脂肪族炭化水素基としては、上記のR1で表される無置換の炭素原子数1〜20の脂肪族炭化水素基として例示したものと同様の基が挙げられる。
R及びR’は、無置換の脂肪族炭化水素基であり、無置換の脂肪族炭化水素基としては、上記のR1で表される無置換の炭素原子数1〜20の脂肪族炭化水素基として例示したものと同様の基が挙げられる。
上記脂肪族炭化水素基としては、上記のR1で表される無置換の炭素原子数1〜20の脂肪族炭化水素基として例示したものと同様の基が挙げられる。
R4で表される無置換の炭素原子数2〜20の複素環基としては、テトラヒドロフラン基、ジオキソラニル基、テトラヒドロピラニル基、モルホリルフラン基、チオフェン基、メチルチオフェン基、ヘキシルチオフェン基、ベンゾチオフェン基、ピロール基、ピロリジン基、イミダゾール基、イミダゾリジン基、イミダゾリン基、ピラゾール基、ピラゾリジン基、ピペリジン基及びピペラジン基、並びに脂肪族炭化水素基で置換されたテトラヒドロフラン基、ジオキソラニル基、テトラヒドロピラニル基、モルホリルフラン基、チオフェン基、メチルチオフェン基、ヘキシルチオフェン基、ベンゾチオフェン基、ピロール基、ピロリジン基、イミダゾール基、イミダゾリジン基、ピラゾール基、ピラゾリジン基、ピペリジン基及びピペラジン基等が挙げられ、これらの複素環基中のアルキレン部分及び複素環とアルキル基との結合部は、−O−、−COO−、−OCO−、−CO−、−CS−、−S−、−SO−、−SO2−、−NR−、−NR−CO−、−CO−NR−、−NR−COO−、−OCO−NR−又は−SiRR’−で中断されていてもよい。但し、これら中断する2価の基は隣り合わないものとする。
上記脂肪族炭化水素基としては、上記のR1で表される無置換の炭素原子数1〜20の脂肪族炭化水素基として例示したものが挙げられる。
R及びR’は、無置換の脂肪族炭化水素基であり、無置換の脂肪族炭化水素基としては、上記のR1で表される無置換の炭素原子数1〜20の脂肪族炭化水素基として例示したものと同様の基が挙げられる。
また、UV感度に優れ、吸収波長の長波長化及び樹脂への溶解性に優れる点から、R1が無置換若しくは置換基を有している炭素原子数6〜20の芳香族炭化水素基である化合物が好ましく、R1がフェニル基、ナフチル基、又はニトロ基、−COOH若しくは炭素原子数1〜20の脂肪族炭化水素基(−O−、−COO−、−OCO−、−CO−で中断されているものを含む)で置換されたフェニル基若しくはナフチル基である化合物が更に好ましい。
また、UV感度に優れ、吸収波長の長波長化及び樹脂への溶解性に優れる点から、;R5、R6、R7、R8、R9、R10及びR11の少なくとも一つがシアノ基、水酸基、カルボキシル基又はチオール基である化合物が好ましく、少なくとも一つがニトロ基である化合物がより好ましく、R10がニトロ基である化合物が特に好ましい。
また、UV感度に優れ、樹脂への溶解性に優れる点から、R4が無置換若しくは置換基を有している炭素原子数1〜20の脂肪族炭化水素基(−O−、−COO−、−OCO−、−CO−で中断されているものを含む)、フェニル基又はナフチル基である化合物が好ましく、炭素原子数1〜10の無置換脂肪族炭化水素基である化合物がより好ましい。
また、UV感度に優れ、吸収波長の長波長化及び樹脂への溶解性に優れる点から、R5、R6、R7、R8、R9、R10及びR11の少なくとも一つが−CO−R12で表される化合物が好ましく、R10が−CO−R12である化合物がより好ましく、中でもR12がハロゲン原子により置換されたフェニルであることが特に好ましい。
即ち、オキシム体(2)とイソシアネート体(3)をジメチルホルムアミド(DMF)中で触媒を用いて反応させることで一般式(1)のR3が水素原子である新規化合物(1’)を得る。R3に水素原子以外の基を導入するにはその後、定法に従いアルキル鎖等を導入することができる。また、上記一般式(1)におけるR2及びR3が互いに連結して窒素原子と形成する環がイミダゾール環である化合物の合成には、イソシアネート体3の代わりに、カルボニルジイミダゾールを原料とすることで合成が可能である。
本発明の感光性樹脂組成物において、(A)光開始剤は上記一般式(1)で表される化合物を少なくとも1種含んでいるものである。光開始剤中における上記一般式(1)で表される化合物の含有量は、好ましくは1〜100質量%、より好ましくは50〜100質量%である。
本発明の感光性樹脂組成物において、(A)光開始剤の含有量は、(B)感光性樹脂組成物100質量部に対して、好ましくは1〜20質量部、より好ましくは1〜10質量部である。(A)光開始剤の含有量が、1質量部未満であると、感度不足による硬化不良などが起こる可能性があり、20質量部を超えると光照射時又は加熱時の揮発物が多くなる可能性がある。
本発明で用いられる(B)感光性樹脂は、アニオン重合性官能基、又は塩基を触媒とし硬化温度が低温化する樹脂を示し、紫外線等のエネルギー線を照射することにより重合して硬化する感光性樹脂又は硬化温度が低温化する硬化樹脂である。上記アニオン重合性官能基とは、紫外線等の活性エネルギー線によって光塩基発生剤から発生する塩基により重合しうる官能基を意味し、例えば、エポキシ基、エピスルフィド基、環状モノマー(σ-バレロラクトン、ε-カプロラクタム)、イソシアネートとアルコールによるウレタン結合形成の触媒、(メタ)アクリル基のマイケル付加触媒、等が挙げられる。(B)感光性樹脂としては、例えば、エポキシ樹脂、ポリアミド樹脂、ポリウレタン樹脂、ナイロン樹脂、、ポリエステル樹脂等が挙げられる。これらの樹脂は単独で用いてもよく、2種以上を併用してもよい。中でも、速やかに反応が進行することや接着性が良好であるという点から、エポキシ樹脂が好適である。
上記エポキシ樹脂の中では、硬化性に優れる点から、グリシジル基を有するものが好ましく、2官能以上のグリシジル基を有するものがより好ましい。
また、上記ナイロン樹脂としては、ε―カプロラクタム、ラウリルラクタム等の環状モノマーを原料とした樹脂等が挙げられる。
また、上記ポリエステル樹脂としては、δ―バレロラクトン、β―プロピオラクトン等の環状モノマーを原料とした樹脂等が挙げられる。
本発明の感光性樹脂組成物には、任意成分として、無機化合物、色材、潜在性エポキシ硬化剤、連鎖移動剤、増感剤、溶剤等の添加剤を用いることができる。
これらの中でも、アルカリ現像性、パターニング性、製膜性、溶解性の点から、ケトン類又はエーテルエステル系溶媒、特に、プロピレングリコール−1−モノメチルエーテル−2−アセテート又はシクロヘキサノンが好ましく用いられる。
本発明の感光性樹脂組成物において、溶媒の含有量は、特に制限されず、各成分が均一に分散又は溶解され、また本発明の感光性樹脂組成物が各用途に適した液状ないしペースト状を呈する量であればよいが、通常、本発明の感光性樹脂組成物中の固形分(溶媒以外の全成分)の量が10〜90質量%となる範囲で溶媒を含有させることが好ましい。
上記有機重合体を使用する場合、その使用量は、(B)感光性樹脂100質量部に対して、好ましくは10〜500質量部である。
ここで、アルキルエーテルを構成するアルキル基としては、メチル基、エチル基又はブチル基が挙げられ、互いに同一であってもよいし、異なっていてもよい。また、アルキルエーテル化されていないメチロール基は、一分子内で自己縮合していてもよく、二分子間で縮合して、その結果オリゴマー成分が形成されていてもよい。
具体的には、ヘキサメトキシメチルメラミン、ヘキサブトキシメチルメラミン、テトラメトキシメチルグリコールウリル、テトラブトキシメチルグリコールウリル等を用いることができる。
これらの中でも、溶媒への溶解性、感光性樹脂組成物から結晶析出しにくいという点から、ヘキサメトキシメチルメラミン、ヘキサブトキシメチルメラミン等のアルキルエーテル化されたメラミンが好ましい。
(E)-(9-ethyl-6-nitro-9H-carbazol-3-yl)(4-((1-methoxypropan-2-yl)oxy)-2-methylphenyl)methanone oximeを50.0g(108mmol)及び脱水DMFを242 gにカルボニルジイミダゾール(CDI)を21.1g(130mmol)を加え、24℃で3時間攪拌した。水と酢酸エチルを加え油水分離し、有機層を水で洗浄した。有機層を無水硫酸マグネシウムで乾燥、ろ過後、脱溶媒した。得られた粗生成物42.7gをクロロホルム220gとジブチルエーテル128gから晶析し、黄色固体6.6g(収率11.0%)を得た。得られた個体のUVスペクトル(λmax、ε)、TG−DTA(融点/℃、外挿点(分解点) / ℃)、IRスペクトル、1H−NMRを分析し、化合物No.1であることを確認した。結果を〔表1〕〜〔表3〕に示す。
(E)-(9-ethyl-6-nitro-9H-carbazol-3-yl)(4-((1-methoxypropan-2-yl)oxy)-2-methylphenyl)methanone oximeを6.00g(13mmol)、アデカスタブBT11(ADEKA社製、ジブチル錫ラウレート)0.2g及び脱水DMFを38gの溶液にイソシアン酸フェニル5.1g(43mmol)を加え、25 ℃で6時間攪拌した。水と酢酸エチルを加え油水分離し、有機層を水で洗浄した。有機層を無水硫酸マグネシウムで乾燥、ろ過後、脱溶媒した。得られた粗生成物9.6gをシリカゲルカラムクロマトグラムにより精製し、淡黄色固体2.3g(収率34.8%)を得た。得られた個体のUVスペクトル(λmax、ε)、TG−DTA(融点/℃、外挿点(分解点) / ℃)、IRスペクトル、1H−NMRを分析し、化合物No.2であることを確認した。結果を〔表1〕〜〔表3〕に示す。
(E)-(9-ethyl-6-nitro-9H-carbazol-3-yl)(4-((1-methoxypropan-2-yl)oxy)-2-methylphenyl)methanone oximeを30.0g(65mmol)、アデカスタブBT11(ADEKA社製、ジブチル錫ラウレート)2.9g及び脱水DMFを182gの溶液にイソシアン酸ブチル15.4g(156mmol)を加え、25℃で8時間攪拌した。水と酢酸エチルを加え油水分離し、有機層を水で洗浄した。有機層を無水硫酸マグネシウムで乾燥、ろ過後、脱溶媒した。得られた粗生成物58.5gをシリカゲルカラムクロマトグラムにより精製し、黄色固体20.5g(収率56.3%)を得た。得られた個体のUVスペクトル(λmax、ε)、TG−DTA(融点/℃、外挿点(分解点)/℃)、IRスペクトル、1H−NMRを分析し、化合物No.3であることを確認した。結果を〔表1〕〜〔表3〕に示す。
(Z)-1-(9-(2-ethylhexyl)-6-nitro-9H-carbazol-3-yl)-2-(hydroxyimino)-2-phenylethanoneを4.00g(8.48mmol)及び脱水DMFを14.40gの溶液を5℃まで冷却し、di(1H-imidazol-1-yl)methanoneを1.65g(10.18mmol)加え、5℃で2時間撹拌した。水と酢酸エチルを加え油水分離し、有機層を水で洗浄した。有機層を無水硫酸マグネシウムで乾燥、ろ過後、脱溶媒した。得られた粗生成物3.50gをカラムクロマトグラフィーにより精製し、淡黄色固体2.5g(収率52.1%)を得た。得られた個体のUVスペクトル(λmax、ε)、TG−DTA(融点/℃、外挿点(分解点)/℃)、IRスペクトル、1H−NMRを分析し、化合物No.16であることを確認した。結果を〔表1〕〜〔表3〕に示す。
(9-ethyl-6-nitro-9H-carbazol-3-yl)(4-((1-methoxypropan-2-yl)oxy)-2-methylphenyl)methanone oximeの9.23gとトリエチルアミン4.05gとジクロロメタン75gを混合して5℃に冷却した。撹拌しながらクロロ炭酸p−ニトロフェニル4.43gをジクロロメタン15gに溶解させたものを30分かけて滴下した。室温まで昇温し、1時間撹拌した。再度5℃まで冷却し、ピペリジン1.87gを滴下した。室温まで昇温し、1時間撹拌した。溶媒を減圧留去し、酢酸エチルで抽出して、5%水酸化ナトリウム水溶液で2回洗浄した。さらに4回水で洗浄し、無水硫酸ナトリウムで乾燥した。溶媒を減圧留去し、酢酸エチルで晶析精製を行い、減圧乾燥して黄色結晶6.84g(ODS純度99%、収率60%)を得た。得られた結晶のUVスペクトル(λmax、ε)、TG−DTA(融点/℃、外挿点(分解点)/℃)、IRスペクトル、1H−NMRを分析し、化合物No.36であることを確認した。結果を〔表1〕〜〔表3〕に示す。
実施例5における(9-ethyl-6-nitro-9H-carbazol-3-yl)(4-((1-methoxypropan-2-yl)oxy)-2-methylphenyl)methanone oxime を、1-(9-(2-ethylhexyl)-6-nitro-9H-carbazol-3-yl)-2-(hydroxyimino)-2-phenylethanoneの1.18gに変更し同様の当量にて反応、処理を行った後、シリカゲルカラムクロマトグラフィー(ヘキサン/酢酸エチル=4/1→3/1)で精製して淡黄色泡状物0.65g(ODS純度99%、収率45%)を得た。
実施例5における(9-ethyl-6-nitro-9H-carbazol-3-yl)(4-((1-methoxypropan-2-yl)oxy)-2-methylphenyl)methanone oxime を、(2,4-dichlorophenyl)(9-ethyl-6-(1-(hydroxyimino)ethyl)-9H-carbazol-3-yl)methanoneの1.23gに変更し同様の当量にて反応、処理を行った後、シクロペンチルメチルエーテルで晶析精製を行い、更に酢酸エチルで熱洗浄を行い淡黄色結晶0.51g(ODS純度94%、収率34%)を得た。
実施例5における(9-ethyl-6-nitro-9H-carbazol-3-yl)(4-((1-methoxypropan-2-yl)oxy)-2-methylphenyl)methanone oxime を、(2,4-dichlorophenyl)(9-ethyl-6-(1-(hydroxyimino)ethyl)-9H-carbazol-3-yl)methanoneの1.23gに変更し、更にピペリジンをエチルブチルアミンに変更し同様の当量にて反応、処理を行った後、シリカゲルカラムクロマトグラフィー(ヘキサン/酢酸エチル=3/2)で精製して淡褐色泡状物1.06g(ODS純度99%、収率64%)を得た。
実施例5における(9-ethyl-6-nitro-9H-carbazol-3-yl)(4-((1-methoxypropan-2-yl)oxy)-2-methylphenyl)methanone oxime を、(9-ethyl-6-(1-(hydroxyimino)ethyl)-9H-carbazol-3-yl)(o-tolyl)methanone1.23gに変更し同様の当量にて反応、処理を行った後、シリカゲルカラムクロマトグラフィー(ヘキサン/酢酸エチル=3/2)で精製して淡褐色泡状物0.79g(ODS純度99%、収率49%)を得た。
実施例5におけるピペリジンを、2−プロピル−2−イミダゾリンに変更し同様の当量にて反応、処理を行った後、シリカゲルカラムクロマトグラフィー(ヘキサン/酢酸エチル=5/1)で精製して黄色結晶1.13g(ODS純度86%,収率63%)を得た。
実施例5におけるピペリジン を、N−メチルピペラジンに変更し同様の当量にて反応、処理を行った後、シリカゲルカラムクロマトグラフィー(ヘキサン/酢酸エチル=5/1)で精製して黄色結晶4.66g(ODS純度98%、収率79%)を得た。
実施例5におけるピペリジン を、3−ピペリジンメタノールに変更し同様の当量にて反応、処理を行った後、シリカゲルカラムクロマトグラフィー(酢酸エチル/メタノール=10/1)で精製して橙黄色結晶4.55g(ODS純度99%、収率75%)を得た。
下記〔表4〕に記載の化合物をアセトニトリル/水=90/10(v)溶液に希釈して濃度100ppm溶液を調製しサンプルとした。調製したサンプルに、超高圧水銀ランプを光源とする光を100mJ/cm2、1000mJ/cm2、10000mJ/cm2(i線における積算量)の条件で照射し、下記〔表4〕に記載の化合物の分解性を調べた。
分解性の評価には、HPLCを用いて未照射時のピークを0として、分解した量を%で表した。
HPLC:日立ハイテクノロジー社製、UV検出器 L−2400
展開溶媒:アセトニトリル/水/トリエチルアミン/酢酸
=90/10/0.2/0.2
流速:1ml/min
カラム:Inertsil ODS−2
カラム温度:40℃
検出:254nm
〔表5〕に記載の化合物0.04mmolをメタノール/テトラヒドロフラン=1/1(重量比)溶液28gに希釈して、化合物溶液を調製した。調製した溶液3.5gに、超高圧水銀ランプを光源とする光を10000mJ/cm2(i線における積算量)照射した。照射後の溶液を2.8g取り、メタノールで希釈して平沼自動滴定装置COM−1600を用いて滴定を行った(滴定液:0.01mol/L塩酸)。別途ジメチルベンジルアミン0.04mmolのメタノール溶液をリファレンスとして滴定し、各滴定値よりアミン発生率を求めた。結果を〔表5〕に示す。
(A)光開始剤成分として、下記〔表6〕に記載の化合物を5質量部、(B)感光性樹脂成分として、EP−4901(ADEKA社製、ビスフェノールF型グリシジルエーテル)52質量部、及び(C)添加剤成分として、カレンズMT BD1(昭和電工社製、エポキシ硬化剤)43質量部を混合し、三本ロールミルにて混練して、実施例21及び比較例4の感光組成樹脂組成物をそれぞれ得た。得られた感光性樹脂組成物について、超高圧水銀ランプによるUV光の照射なし及び200mJ/cm2のUV光照射後に60℃にて60分間加熱し、硬化率を測定した。硬化率は、5000mJ/cm2のUV光照射後、120℃で60分硬化させたときのFI−IRにおける(3450cm-1のピーク強度)/(1510cm-1のピーク強度)の値を硬化率100%として、相対値として求めた。結果を下記〔表6〕に示す。
Claims (6)
- 下記一般式(1)で表される新規化合物。
R2及びR3は、それぞれ独立に、水素原子、無置換若しくは置換基を有している炭素原子数1〜20の脂肪族炭化水素基又はフェニル基であるか、R2及びR3が、互いに連結して形成する窒素原子及び炭素原子からなる環であり、
R4は、無置換若しくは置換基を有している炭素原子数1〜20の脂肪族炭化水素基、無置換若しくは置換基を有している炭素原子数6〜20の芳香族炭化水素基又は無置換若しくは置換基を有している炭素原子数2〜20の複素環基を表し、
R5、R6、R7、R8、R9、R10及びR11は、それぞれ独立に、水素原子、シアノ基、ニトロ基、−OR12、−COOR12、−CO−R12、−SR12、ハロゲン原子、無置換若しくは置換基を有している炭素原子数1〜20の脂肪族炭化水素基、無置換若しくは置換基を有している炭素原子数6〜20の芳香族炭化水素基又は無置換若しくは置換基を有している炭素原子数2〜20の複素環基を表し、R12は、無置換若しくは置換基を有している炭素原子数1〜20の脂肪族炭化水素基、無置換若しくは置換基を有している炭素原子数6〜20の芳香族炭化水素基又は無置換若しくは置換基を有している炭素原子数2〜20の複素環基を表し、
nは、0又は1を表す。) - 上記一般式(1)中のR1が、無置換若しくは置換基を有している炭素原子数6〜20の芳香族炭化水素基である請求項1に記載の新規化合物。
- 上記一般式(1)中のR5、R6、R7、R8、R9、R10及びR11の内、少なくとも一つがニトロ基である請求項1又は2に記載の新規化合物。
- 上記一般式(1)中のnが、0である請求項1〜3の何れか1項に記載の新規化合物。
- (A)下記一般式(1)で表される化合物を少なくとも1種含む光開始剤及び(B)感光性樹脂を含有する感光性樹脂組成物。
R2及びR3は、それぞれ独立に、水素原子、無置換若しくは置換基を有している炭素原子数1〜20の脂肪族炭化水素基又はフェニル基であるか、R2及びR3が、互いに連結して形成する窒素原子及び炭素原子からなる環であり、
R4は、無置換若しくは置換基を有している炭素原子数1〜20の脂肪族炭化水素基、無置換若しくは置換基を有している炭素原子数6〜20の芳香族炭化水素基又は無置換若しくは置換基を有している炭素原子数2〜20の複素環基を表し、
R5、R6、R7、R8、R9、R10及びR11は、それぞれ独立に、水素原子、シアノ基、ニトロ基、−OR12、−COOR12、−CO−R12、−SR12、ハロゲン原子、無置換若しくは置換基を有している炭素原子数1〜20の脂肪族炭化水素基、無置換若しくは置換基を有している炭素原子数6〜20の芳香族炭化水素基又は無置換若しくは置換基を有している炭素原子数2〜20の複素環基を表し、R12は、無置換若しくは置換基を有している炭素原子数1〜20の脂肪族炭化水素基、無置換若しくは置換基を有している炭素原子数6〜20の芳香族炭化水素基又は無置換若しくは置換基を有している炭素原子数2〜20の複素環基を表し、
nは、0又は1を表す。) - 請求項5に記載の感光性樹脂組成物にエネルギー線を照射してなる硬化物。
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JP6208119B2 (ja) | 2017-10-04 |
EP2829534A4 (en) | 2015-12-30 |
TWI591056B (zh) | 2017-07-11 |
CN104144912B (zh) | 2018-07-31 |
US9594302B2 (en) | 2017-03-14 |
TW201348201A (zh) | 2013-12-01 |
US20150064623A1 (en) | 2015-03-05 |
KR20140138679A (ko) | 2014-12-04 |
KR102026722B1 (ko) | 2019-09-30 |
WO2013141014A1 (ja) | 2013-09-26 |
EP2829534A1 (en) | 2015-01-28 |
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CN104144912A (zh) | 2014-11-12 |
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