WO2017030005A1 - 組成物 - Google Patents
組成物 Download PDFInfo
- Publication number
- WO2017030005A1 WO2017030005A1 PCT/JP2016/073011 JP2016073011W WO2017030005A1 WO 2017030005 A1 WO2017030005 A1 WO 2017030005A1 JP 2016073011 W JP2016073011 W JP 2016073011W WO 2017030005 A1 WO2017030005 A1 WO 2017030005A1
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- WO
- WIPO (PCT)
- Prior art keywords
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- carbon atoms
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- groups
- ring
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- 239000000203 mixture Substances 0.000 title claims abstract description 69
- -1 oxime ester compounds Chemical class 0.000 claims abstract description 224
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 22
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 18
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 258
- 125000001424 substituent group Chemical group 0.000 claims description 100
- 125000000217 alkyl group Chemical group 0.000 claims description 78
- 125000003118 aryl group Chemical group 0.000 claims description 75
- 125000000623 heterocyclic group Chemical group 0.000 claims description 75
- 150000001875 compounds Chemical class 0.000 claims description 53
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 46
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 39
- 150000002430 hydrocarbons Chemical group 0.000 claims description 38
- 125000005843 halogen group Chemical group 0.000 claims description 33
- 125000000962 organic group Chemical group 0.000 claims description 33
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 22
- 229910052799 carbon Inorganic materials 0.000 claims description 21
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- 125000004429 atom Chemical group 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 150000001721 carbon Chemical group 0.000 claims description 11
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 11
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 4
- 125000001905 inorganic group Chemical group 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 55
- 125000001931 aliphatic group Chemical group 0.000 description 45
- 239000004593 Epoxy Substances 0.000 description 31
- 239000002253 acid Substances 0.000 description 30
- 239000010408 film Substances 0.000 description 29
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 28
- 239000011347 resin Substances 0.000 description 23
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- 239000011248 coating agent Substances 0.000 description 16
- 239000000463 material Substances 0.000 description 16
- 239000000178 monomer Substances 0.000 description 16
- 238000000576 coating method Methods 0.000 description 15
- 239000000049 pigment Substances 0.000 description 15
- 229920002554 vinyl polymer Polymers 0.000 description 13
- 239000000975 dye Substances 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 229940049920 malate Drugs 0.000 description 11
- BJEPYKJPYRNKOW-UHFFFAOYSA-L malate(2-) Chemical compound [O-]C(=O)C(O)CC([O-])=O BJEPYKJPYRNKOW-UHFFFAOYSA-L 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- 230000035945 sensitivity Effects 0.000 description 10
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 10
- 150000008065 acid anhydrides Chemical class 0.000 description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 229920003986 novolac Polymers 0.000 description 9
- 230000003287 optical effect Effects 0.000 description 9
- 150000007519 polyprotic acids Polymers 0.000 description 9
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 9
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 8
- 238000004040 coloring Methods 0.000 description 8
- 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 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 239000002270 dispersing agent Substances 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 150000002484 inorganic compounds Chemical class 0.000 description 7
- 229910010272 inorganic material Inorganic materials 0.000 description 7
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- 125000004434 sulfur atom Chemical group 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- OAPPEBNXKAKQGS-UHFFFAOYSA-N Benz[c]acridine Chemical compound C1=CC=C2C3=NC4=CC=CC=C4C=C3C=CC2=C1 OAPPEBNXKAKQGS-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 6
- 239000006229 carbon black Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000003086 colorant Substances 0.000 description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 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 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 5
- 229930185605 Bisphenol Natural products 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 4
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000002723 alicyclic group Chemical group 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- 125000005110 aryl thio group Chemical group 0.000 description 4
- 125000004104 aryloxy group Chemical group 0.000 description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- CBFCDTFDPHXCNY-UHFFFAOYSA-N icosane Chemical compound CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 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
- 230000001681 protective effect Effects 0.000 description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- 125000000565 sulfonamide group Chemical group 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 4
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 3
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 3
- BGCSUUSPRCDKBQ-UHFFFAOYSA-N 2,4,8,10-tetraoxaspiro[5.5]undecane Chemical compound C1OCOCC21COCOC2 BGCSUUSPRCDKBQ-UHFFFAOYSA-N 0.000 description 3
- AZUHIVLOSAPWDM-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)-1h-imidazole Chemical class C1=CNC(C=2NC=CN=2)=N1 AZUHIVLOSAPWDM-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 3
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
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- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 229930016911 cinnamic acid Natural products 0.000 description 3
- 235000013985 cinnamic acid Nutrition 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 238000010835 comparative analysis Methods 0.000 description 3
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
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- 125000000524 functional group Chemical group 0.000 description 3
- 125000002541 furyl group Chemical group 0.000 description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 125000001041 indolyl group Chemical group 0.000 description 3
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- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 3
- JESXATFQYMPTNL-UHFFFAOYSA-N mono-hydroxyphenyl-ethylene Natural products OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000002347 octyl 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])[H] 0.000 description 3
- 229920000620 organic polymer Polymers 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 125000003386 piperidinyl group Chemical group 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
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- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000005495 pyridazyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000001054 red pigment Substances 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 150000003346 selenoethers Chemical class 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 239000007784 solid electrolyte Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 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
- 238000003860 storage Methods 0.000 description 1
- 239000011232 storage material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 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
- ADXGNEYLLLSOAR-UHFFFAOYSA-N tasosartan Chemical compound C12=NC(C)=NC(C)=C2CCC(=O)N1CC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 ADXGNEYLLLSOAR-UHFFFAOYSA-N 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 239000001017 thiazole dye Substances 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 239000001003 triarylmethane dye Substances 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water 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
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Chemical group C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- UIYCHXAGWOYNNA-UHFFFAOYSA-N vinyl sulfide Chemical compound C=CSC=C UIYCHXAGWOYNNA-UHFFFAOYSA-N 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- 150000003732 xanthenes Chemical class 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- 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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
Definitions
- the present invention relates to a composition containing a latent antioxidant which is inactive at room temperature and is activated by heating to a predetermined temperature to exhibit a function, and a polymerization initiator having a specific structure.
- Photosensitive compositions are widely used in paints, coating agents, various resists and the like.
- Patent Document 1 discloses a photosensitive coloring composition for a color filter containing an antioxidant
- Patent Document 2 discloses a photosensitive resin composition containing a phenol antioxidant, Although it is described that heat resistance can be improved, there is no description that high sensitivity and high transparency can be obtained by using a latent antioxidant.
- an object of the present invention is to provide a composition excellent in sensitivity and transparency.
- the present inventors contain a latent antioxidant (A) and a polymerization initiator (B) containing at least one oxime ester compound represented by the following general formula (I).
- the inventors have found that the composition can achieve the above object, and have reached the present invention.
- R 1 and R 2 each independently represent R 11 , OR 11 , COR 11 , SR 11 , CONR 12 R 13 or CN;
- R 11 , R 12 and R 13 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms or a carbon atom.
- R 21 , R 22 and R 23 are further R 21 , OR 21 , COR 21 , SR 21 , NR 22 R 23 , CONR 22 R 23 , NR 22 OR 23 , NCOR 22 OCOR 23 , NR 22 COR 21 , OCOR 21 , COOR 21 , SCOR 21 , OCSR 21 , COSR 21 , CSOR 21 , hydroxyl group, nitro group, CN, halogen atom, or COOR 21 may be substituted, R 21 , R 22 and R 23 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms or a carbon atom.
- the hydrogen atom of the group represented by R 21 , R 22 and R 23 may be further substituted with a hydroxyl group, a nitro group, CN, a halogen atom, a hydroxyl group or a carboxyl group
- the methylene group of the alkylene moiety of the group represented by R 11 , R 12 , R 13 , R 21 , R 22 and R 23 is —O—, —S—, —COO—, —OCO—, —OCOO—, May be replaced by —CONR 24 —, —NR 24 —, —NR 24 CO—, —NR 24 COO—, —OCONR 24 —, —SCO—, —COS—, —OCS— or —SCOO—.
- R 24 represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms.
- the alkyl part of the group represented by R 11 , R 12 , R 13 , R 21 , R 22 , R 23 and R 24 may have a branched side chain or a cyclic alkyl.
- R 3 represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms.
- alkyl part of the group represented by R 3 may have a branched side chain or a cyclic alkyl, and R 3 and R 7 , R 3 and R 8 , R 4 and R 5 , R 5 and R 6 and R 6 and R 7 together may form a ring,
- the hydrogen atom of the group represented by R 3 is further R 21 , OR 21 , COR 21 , SR 21 , NR 22 R 23 , CONR 22 R 23 , NR 22 OR 23 , NCOR 22 OCOR 23 , NR 22 COR 21 , OCOR.
- R 4 , R 5 , R 6 and R 7 are each independently R 11 , OR 11 , SR 11 , COR 14 , CONR 15 R 16 , NR 12 COR 11 , OCOR 11 , COOR 14 , SCOR 11 , OCSR 11 , COSR 14 , CSOR 11 , a hydroxyl group, CN or a halogen atom, R 4 and R 5 , R 5 and R 6 and R 6 and R 7 may be combined to form a ring,
- the hydrogen atoms of the groups represented by R 4 , R 5 , R 6 and R 7 are further R 21 , OR 21 , COR 21 , SR 21 , NR 22 R 23 , CONR 22 R 23 , NR 22 OR 23 , NCOR 22.
- OCOR 23 NR 22 COR 21 , OCOR 21 , COOR 21 , SCOR 21 , OCSR 21 , COSR 21 , CSOR 21 , hydroxyl group, nitro group, CN, halogen atom or COOR 21 may be substituted, R 14 , R 15 and R 16 represent a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, The alkyl part of the group represented by R 14 , R 15 and R 16 may have a branched side chain or a cyclic alkyl.
- R 8 is R 11 , OR 11 , SR 11 , COR 11 , CONR 12 R 13 , NR 12 COR 11 , OCOR 11 , COOR 11 , SCOR 11 , OCSR 11 , COSR 11 , CSOR 11 , hydroxyl group, CN or halogen atom Represents n represents 0 or 1.
- a composition containing a latent antioxidant having a specific structure and a polymerization initiator having a specific structure is excellent in sensitivity and transparency.
- composition of the present invention will be described based on preferred embodiments.
- composition of the present invention contains a latent antioxidant (A) and a polymerization initiator (B) containing at least one oxime ester compound represented by the above general formula (I).
- A latent antioxidant
- B polymerization initiator
- the latent antioxidant (A) used in the composition of the present invention is inactive at room temperature or in a pre-baking step, and is heated at 100 to 250 ° C. or 80 to 200 ° C. in the presence of an acid / base catalyst. Since the protecting group is removed and becomes active by heating with a compound having a skeleton represented by the following general formula (III), the synthesis is easy, the heat resistance is high, and the effect of the present invention is high. preferable.
- ring A 1 represents a 5-membered or 6-membered hydrocarbon ring or heterocyclic ring
- R 61 each independently represents a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms, which may have a substituent, or 6 to 6 carbon atoms.
- R 62 each independently represents an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, carbon Represents a heterocyclic group containing 2 to 20 atoms or a trialkylsilyl group, Methylene groups in the alkyl group or an arylalkyl group represented by R 61 and R 62, carbon - carbon double bond, -O -, - S -, - CO -, - O-CO -, - CO-O -, -O-CO-O-, -O-CO-O-, -S-CO-, -CO-S-, -S-CO-O-, -O-CO-NH-NH
- ring A 1 , R 61 , R 62 , d and k are the same as in the general formula (III), m represents an integer of 1 to 10, X 5 represents a direct bond or an m-valent atom, an inorganic group, or an organic group.
- Examples of the five-membered hydrocarbon ring represented by A 1 in the above general formula (III) and general formula (III-A) include cyclopentadiene, and the five-membered heterocyclic ring includes furan and thiophene.
- the six-membered hydrocarbon ring includes benzene, etc.
- membered heterocyclic rings include piperidine, piperazine, morpholine, thiomorpholine, pyridine, pyrazine, pyrimidine, pyridazine, triazine, etc., and these rings may be condensed or substituted with other rings.
- examples thereof include, for example, quinoline, isoquino Emissions, indole, Yurorijin, benzoxazole, benzotriazole, azulene, naphthalene, anthracene, fluorene, perylene, pyrene, and the like.
- Examples of the halogen atom represented by R 61 include fluorine, chlorine, bromine, and iodine (in the following description, all the halogen atoms are the same as described above).
- Examples of the alkyl group having 1 to 40 carbon atoms represented by R 61 include methyl, ethyl, propyl, iso-propyl, butyl, sec-butyl, tert-butyl, iso-butyl, amyl, iso-amyl, tert- Amyl, cyclopentyl, hexyl, 2-hexyl, 3-hexyl, cyclohexyl, 4-methylcyclohexyl, heptyl, 2-heptyl, 3-heptyl, iso-heptyl, tert-heptyl, 1-octyl, iso-octyl, tert-octyl Adamantyl and the like, and examples of the alkyl group
- Examples of the aryl group having 6 to 20 carbon atoms represented by R 61 and R 62 include phenyl, naphthyl, anthracenyl, phenanthryl, fluorenyl, indenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4- Vinylphenyl, 3-iso-propylphenyl, 4-iso-propylphenyl, 4-butylphenyl, 4-iso-butylphenyl, 4-tert-butylphenyl, 4-hexylphenyl, 4-cyclohexylphenyl, 4-octylphenyl 4- (2-ethylhexyl) phenyl, 4-stearylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 2,4-di
- Examples of the arylalkyl group having 7 to 20 carbon atoms represented by R 61 and R 62 include benzyl, 1-methyl-1-phenylethyl, 1-naphthylmethyl, 9-anthracenylmethyl, 9-fluorenyl, 3 -Phenylpropyl, methyl-2-phenylpropan-2-yl, diphenylmethyl, triphenylmethyl, phenethyl, styryl, cinnamyl and the like
- Examples of the heterocyclic group having 2 to 20 carbon atoms represented by R 61 and R 62 include a pyridine ring, pyrimidine ring, pyridazine ring, piperidine ring, pyran ring, pyrazoline ring, triazine ring, pyrroline ring, quinoline ring, Isoquinoline ring, imidazoline ring, benzimidazoline ring, triazoline ring, furan
- a silyl group is mentioned.
- the alkyl group having 1 to 8 carbon atoms represented by R ′ include those satisfying a predetermined number of carbon atoms among the above alkyl groups represented by R 61 .
- R 61 is a hydrogen atom
- an alkyl group having 1 to 8 carbon atoms or an aryl group having 6 to 12 carbon atoms are easy to synthesize.
- R 62 is preferably one in which —CO—O— is bonded to the terminal of the alkyl group having 1 to 8 carbon atoms on the oxygen atom side because the function is efficiently exhibited as a latent additive.
- X 5 represents a direct bond or an m-valent atom, an inorganic group, or an organic group. Specifically, a direct bond, a hydrogen atom, a nitrogen atom, an oxygen atom, a sulfur atom, A phosphorus atom, a group represented by the following (III-a) or (III-b),>C ⁇ O,> NR 63 , —OR 63 , —SR 63 , —NR 63 R 64 , the same valence as m
- R 63 and R 64 are each a hydrogen atom, an aliphatic hydrocarbon group having 1 to 35 carbon atoms that may have a substituent, or a 6 to 35 carbon atom that may have a substituent.
- All or a part of these aliphatic hydrocarbon group, aromatic ring-containing hydrocarbon group and heterocyclic ring-containing group is a carbon-carbon double bond, —O—, —S—, —CO—, —O—CO—, —CO—O—, —O—CO—O—, —S—CO—, —CO—S—, —S—CO—O—, —O.
- -CO-S - CO- NH -, - NH-CO -, - NH-CO-O -, - NH-CO-O -, - NR '-, - S-S -, - SO 2 - or It may be replaced by a group selected from nitrogen atoms.
- X 5 when X 5 is a nitrogen atom, a phosphorus atom, or a group represented by the following (III-a) or (III-b), m is 3, X 5 is an oxygen atom or a sulfur atom,> C ⁇ O , —NH—CO—, —CO—NH— or> NR 63 , m is 2, and when X 5 is —OR 63 , —SR 63 or —NR 63 R 64 , m is 1. X 5 may form a ring together with A 1 .
- the latent antioxidant represented by the general formula (III-A) has a structure in which m specific groups are bonded to the m-valent specific atom or group represented by X 5 .
- the m groups are the same as or different from each other.
- the value of m is 1 to 10, and preferably 2 to 6 from the viewpoint of ease of synthesis.
- Examples of the aliphatic hydrocarbon group having 1 to 120 carbon atoms having the same valence as m represented by X 5 in the general formula (III-A) are those in which m is monovalent, such as methyl, Ethyl, propyl, isopropyl, cyclopropyl, butyl, sec-butyl, tert-butyl, isobutyl, amyl, isoamyl, tert-amyl, cyclopentyl, hexyl, 2-hexyl, 3-hexyl, cyclohexyl, bicyclohexyl, 1-methylcyclohexyl Alkyl groups such as heptyl, 2-heptyl, 3-heptyl, isoheptyl, tertiary heptyl, n-octyl, isooctyl, tertiary octyl, 2-ethylhexyl, nonyl,
- m is divalent, alkylene such as methylene, ethylene, propylene, butylene, butyldiyl; the methylene chain of the alkylene is replaced by —O—, —S—, —CO—O—, —O—CO— Residues of diols such as ethanediol, propanediol, butanediol, pentanediol, hexanediol; residues of dithiols such as ethanedithiol, propanedithiol, butanedithiol, pentanedithiol, hexanedithiol and these groups are described later A group substituted by a substituent, and the like, Examples of the compound in which m is trivalent include alkylidines such as propyridine and 1,1,3-butyridine, and groups in which these groups are substituted with substituents described later.
- the monovalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms which may have a substituent having the same valence as m, includes benzyl, phenethyl, diphenyl, where m is monovalent An arylalkyl group such as methyl, triphenylmethyl, styryl, cinnamyl, etc .; an aryl group such as phenyl, naphthyl; an aryloxy group such as phenoxy, naphthyloxy; an arylthio group such as phenylthio, naphthylthio; Substituted groups, etc.
- m is divalent, arylene groups such as phenylene and naphthylene; residues of bifunctional phenols such as catechol and bisphenol; 2,4,8,10-tetraoxaspiro [5,5] undecane and the like and these groups Is a group substituted by a substituent described later,
- m being trivalent include phenyl-1,3,5-trimethylene and the like, and groups in which these groups are substituted with substituents described later.
- the heterocycle-containing group having 2 to 35 carbon atoms which may have a substituent having the same valence as m is m-monovalent, and pyridyl, pyrimidyl, pyridazyl, piperidyl, pyranyl, Pyrazolyl, triazyl, pyrrolyl, quinolyl, isoquinolyl, imidazolyl, benzimidazolyl, triazolyl, furyl, furanyl, benzofuranyl, thienyl, thiophenyl, benzothiophenyl, thiadiazolyl, thiazolyl, benzothiazolyl, oxazolyl, benzoxazolyl, isothiazolyl, isoxazolyl, indolyl, 2 -Pyrrolidinone-1-yl, 2-piperidone-1-yl, 2,4-dioxyimidazolidin-3-yl, 2,4-dioxyox
- As m is a divalent group, a group having a pyridine ring, a pyrimidine ring, a piperidine ring, a piperazine ring, a triazine ring, a furan ring, a thiophene ring, an indole ring or the like, and a group in which these groups are substituted by a substituent described later.
- Examples of m being trivalent include a group having an isocyanuric ring, a group having a triazine ring, and a group in which these groups are substituted with a substituent described later.
- Examples of the aliphatic hydrocarbon group having 1 to 35 carbon atoms which may have a substituent represented by R 63 and R 64 include the aliphatic hydrocarbon group or aliphatic carbon group represented by X 5 above.
- Examples of the heterocyclic ring-containing group include an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms or a heterocyclic group having 2 to 35 carbon atoms represented by X 5 or a combination of these groups with the following substituents: Groups.
- M-valent organic group represented by X 5 for example, the above-mentioned aliphatic hydrocarbon group, aromatic ring-containing hydrocarbon group, heterocycle-containing group
- substituents include ethylenically unsaturated groups such as vinyl, allyl, acrylic and methacryl; halogen atoms such as fluorine, chlorine, bromine and iodine Acetyl, 2-chloroacetyl, propionyl, octanoyl, acryloyl, methacryloyl, phenylcarbonyl (benzoyl), phthaloyl, 4-trifluoromethylbenzoyl, pivaloyl, salicyloyl, oxaloyl, stearoyl, methoxycarbonyl, ethoxycarbonyl, ethyl, ethylenically unsaturated groups such as vinyl, allyl, acrylic and methacryl; halogen atoms such as fluorine, chlorine, bro
- Y 10 represents a single bond, a sulfur atom, —CR 65 R 66 —, —NR 67 —, a divalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, the number of carbon atoms Represents an aromatic ring-containing hydrocarbon group having 6 to 35 or a heterocyclic ring-containing group having 2 to 35 carbon atoms, or any substituent represented by the following (1-1) to (1-3):
- the aliphatic hydrocarbon group is interrupted by —O—, —S—, —CO—, —COO—, —OCO— or —NH—, or a linking group that combines these without adjacent oxygen atoms.
- Z 1 and Z 2 are each independently a direct bond, —O—, —S—,> CO, —CO—O—, —O—CO—, —SO 2 —, —SS—, —SO—, > NR 67 ,> PR 67 , a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms or a divalent aromatic hydrocarbon group having 6 to 10 carbon atoms, which may have a substituent.
- R 65 , R 66 and R 67 each independently have a hydrogen atom, a substituent or a C 1-3C aliphatic hydrocarbon group or a substituent.
- R 71 represents a hydrogen atom, a phenyl group which may have a substituent, or a cycloalkyl group having 3 to 10 carbon atoms
- R 72 represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or a halogen atom
- the alkyl group, alkoxy group and alkenyl group are substituents.
- You may have f is an integer of 0 to 5.
- R 73 and R 74 are each independently an alkyl group having 1 to 10 carbon atoms which may have a substituent, or 6 carbon atoms which may have a substituent.
- the methylene group in the alkyl group and arylalkyl group may be interrupted by an unsaturated bond, —O— or —S—, R 73 may form a ring with adjacent R 73 , p represents
- Y 11 represents a single bond, a trivalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, an alicyclic hydrocarbon group having 3 to 35 carbon atoms, or 6 carbon atoms.
- Z 1 , Z 2 and Z 3 are each independently a direct bond, —O—, —S—,> CO, —CO—O—, —O—CO—, —SO 2 —, —SS—, — SO—,> NR 68 ,> PR 68 , a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms or a divalent aromatic carbon atom having 6 to 10 carbon atoms, which may have a substituent
- R 68 represents a hydrogen atom, an aliphatic hydrocarbon group having 1 to 35 carbon atoms which may have a substituent, or an aromatic
- Each of the aliphatic hydrocarbon groups may be interrupted by a carbon-carbon double bond, —O—, —CO—, —O—CO—, —CO—O— or —SO 2 —.
- Y 12 represents a single bond, a carbon atom, a tetravalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, or an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms. Or a heterocyclic group containing 2 to 35 carbon atoms,
- the aliphatic hydrocarbon group may be interrupted by —COO—, —O—, —OCO—, —NHCO—, —NH— or —CONH—, wherein Z 1 to Z 4 are each independently It is a group in the same range as the groups represented by Z 1 to Z 3 in the general formula (2).
- Y 13 represents a single bond, a pentavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, or 2 carbon atoms. Represents ⁇ 35 heterocycle-containing groups,
- the aliphatic hydrocarbon group may be interrupted by —COO—, —O—, —OCO—, —NHCO—, —NH— or —CONH—, Z 1 to Z 5 are each independently a group in the same range as the group represented by Z 1 to Z 3 in the general formula (2).
- Y 14 represents a single bond, a hexavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, or 2 carbon atoms. Represents ⁇ 35 heterocycle-containing groups,
- the aliphatic hydrocarbon group may be interrupted by —COO—, —O—, —OCO—, —NHCO—, —NH— or —CONH—,
- Z 1 to Z 6 are each independently a group in the same range as the group represented by Z 1 to Z 3 in the general formula (2).
- the aliphatic hydrocarbon group having 1 to 35 carbon atoms which may have a substituent represented by R 65 , R 66 and R 67 may be the above general formula (III- m-valent organic radical monovalent aliphatic hydrocarbon groups and those groups exemplified as the m-valent organic group represented by X 5 in a) is represented by X 5 in the above general formula (III-a) And those satisfying a predetermined number of carbon atoms among the groups substituted by those exemplified as the substituent of the group represented by the formula: m, which is represented by X 5 in these groups or the above general formula (III-A)
- the divalent group in which the divalent aliphatic hydrocarbon group exemplified as the divalent organic group is substituted with Z 1 and Z 2 is a divalent carbon atom represented by Y 10 in the general formula (1) 1 To 35 aliphatic hydrocarbon groups.
- the aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms which may have a substituent represented by R 65 , R 66 and R 67 is X 5 in the above general formula (III-A).
- Examples of the divalent group in which the group is substituted with Z 1 and Z 2 include the divalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by Y 10 in the general formula (1).
- the heterocyclic group having 2 to 35 carbon atoms which may have a substituent represented by R 65 , R 66 and R 67 is represented by X 5 in the above general formula (III-A).
- the divalent heterocyclic ring-containing groups exemplified as the m-valent organic group represented by X 5 in the above general formula (III-A) are Z 1 and Z.
- Examples of the divalent group substituted with 2 include the divalent heterocyclic group having 2 to 35 carbon atoms represented by Y 10 in the general formula (1).
- the aromatic hydrocarbon groups of formulas 6 to 10 are each described above as a divalent aliphatic hydrocarbon group or aromatic ring-containing hydrocarbon group that may have a substituent represented by Y 10. Among them, those having a predetermined number of carbon atoms can be mentioned.
- examples of the cycloalkyl group having 3 to 10 carbon atoms represented by R 71 include cyclopropyl, cyclobutyl, cyclopentyl, cyclohebutyl, cyclooctyl and the like.
- examples of the alkyl group having 1 to 10 carbon atoms represented by R 72 include groups satisfying a predetermined number of carbon atoms among the groups exemplified as the alkyl group having 1 to 40 carbon atoms represented by R 61.
- alkoxy group having 1 to 10 carbon atoms represented by R 72 examples include methyloxy, ethyloxy, propyloxy, isopropyloxy, butyloxy, sec-butyloxy, tert-butyloxy, isobutyloxy, amyloxy, isoamyloxy, tert-amyloxy Hexyloxy, cyclohexyloxy, heptyloxy, isoheptyloxy, tertiary heptyloxy, n-octyloxy, isooctyloxy, tertiary octyloxy, 2-ethylhexyloxy, nonyloxy, decyloxy, etc.
- the substituents of the phenyl group, alkyl group, alkoxy group and alkenyl group are the same as those exemplified as the substituent of the group representing the m-valent organic group represented by X 5 in the general formula (III-A). is there.
- the alkyl group having 1 to 10 carbon atoms that may have a substituent represented by R 73 and R 74 is represented by R 61.
- the groups exemplified as the alkyl group having 1 to 40 carbon atoms groups satisfying a predetermined number of carbon atoms, and the like can be mentioned.
- Examples of the aryl group having 6 to 20 carbon atoms which may have a substituent represented by R 73 and R 74 include the groups exemplified as the aryl group having 6 to 20 carbon atoms represented by R 61. Etc.
- Examples of the aryloxy group having 6 to 20 carbon atoms which may have a substituent represented by R 73 and R 74 include phenyloxy, naphthyloxy, 2-methylphenyloxy, 3-methylphenyloxy, 4-methylphenyloxy, 4-vinylphenyldioxy, 3-iso-propylphenyloxy, 4-iso-propylphenyloxy, 4-butylphenyloxy, 4-tert-butylphenyloxy, 4-hexylphenyloxy, 4-cyclohexylphenyloxy, 4-octylphenyloxy, 4- (2-ethylhexyl) phenyloxy, 2,3-dimethylphenyloxy, 2,4-dimethylphenyloxy, 2,5-dimethylphenyloxy, 2.6- Dimethylphenyloxy, 3.4-dimethylphenyloxy, 3.5 Dimethylphenyloxy, 2,4-di-tert-butylphenyloxy,
- Examples include groups in which the oxygen atom of the oxy group is substituted with a sulfur atom,
- Groups in which the oxygen atom of the aryloxy group is substituted with an alkenyl group such as vinyl, allyl, 1-propenyl, isopropenyl, 2-butenyl, 1,3-butadienyl, 2-pentenyl, 2-octenyl, etc.
- Examples of the arylalkyl group having 7 to 20 carbon atoms represented by R 73 and R 74 include groups exemplified as the arylalkyl group having 7 to 20 carbon atoms represented by R 61 .
- the heterocycle-containing group having 2 to 20 carbon atoms which may have a substituent represented by R 73 and R 74 includes a heterocycle-containing group having 2 to 20 carbon atoms represented by R 61 And the groups exemplified as above.
- the trivalent aliphatic hydrocarbon group having 1 to 35 carbon atoms represented by Y 11 in the general formula (2) is an m-valent organic compound represented by X 5 in the general formula (III-A).
- Examples of the monovalent to trivalent aliphatic hydrocarbon group exemplified as the group and the substituent of the group in which the group represents the m-valent organic group represented by X 5 in the above general formula (III-A) Among the groups substituted by the above, those satisfying the predetermined number of carbon atoms include trivalent groups substituted with Z 1 , Z 2 and Z 3 , etc.
- Examples of the trivalent alicyclic hydrocarbon group having 3 to 35 carbon atoms represented by Y 11 in the general formula (2) include cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclodecanyl, 1-adamantyl, 2- Adamantyl, noradamantyl, 2-methyladamantyl, norbornyl, isonorbornyl, perhydronaphthyl, perhydroanthracenyl, bicyclo [1.1.0] butyl, bicyclo [1.1.1] pentyl, bicyclo [2.1.
- a trivalent aromatic ring-containing hydrocarbon group and a group in which these groups are substituted by those exemplified as the substituent of the group representing the m-valent organic group represented by X 5 in the general formula (III-A) And the like include trivalent groups substituted with Z 1 , Z 2 and Z 3 , and the like.
- Examples of the trivalent heterocyclic group having 2 to 35 carbon atoms represented by Y 11 include monovalent to 3 exemplified as the m-valent organic group represented by X 5 in the general formula (III-A).
- a valent heterocycle-containing group a group substituted by those exemplified as the substituent of the group representing the m-valent organic group represented by X 5 in the general formula (III-A), 1 , trivalent groups substituted with Z 2 and Z 3 , etc.
- Examples of the heterocyclic group having 2 to 35 carbon atoms, which may have an aromatic hydrocarbon group having 6 to 35 and a substituent may include R 65 and R 66 in the general formula (1), respectively.
- Examples of the tetravalent aliphatic hydrocarbon group having 1 to 35 carbon atoms represented by Y 12 in the general formula (3) include an m-valent organic compound represented by X 5 in the general formula (III-A).
- Examples of the monovalent to trivalent aliphatic hydrocarbon group exemplified as the group and the substituent of the group in which the group represents the m-valent organic group represented by X 5 in the above general formula (III-A) Among the groups substituted by the above, those satisfying the predetermined number of carbon atoms include tetravalent groups substituted with Z 1 , Z 2 , Z 3 and Z 4 , etc.
- Examples of the aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by Y 12 include the monovalent to trivalent compounds exemplified as the m-valent organic group represented by X 5 in the general formula (III-A).
- the aromatic ring-containing hydrocarbon group and the group substituted by those exemplified as the substituent of the group representing the m-valent organic group represented by X in the above general formula (III-A) is Z 1.
- Examples of the tetravalent heterocyclic group having 2 to 35 carbon atoms represented by Y 12 include monovalent to 3 exemplified as the m-valent organic group represented by X 5 in the general formula (III-A).
- the pentavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms represented by Y 13 in the general formula (4) is an m-valent organic compound represented by X 5 in the general formula (III-A).
- the pentavalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by Y 13 is a monovalent group exemplified as the m-valent organic group represented by X 5 in the general formula (III-A).
- the hexavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms represented by Y 14 in the general formula (5) is an m-valent organic compound represented by X 5 in the general formula (III-A).
- Examples of the monovalent to trivalent aliphatic hydrocarbon group exemplified as the group and the substituent of the group in which the group represents the m-valent organic group represented by X 5 in the above general formula (III-A) A group having a predetermined number of carbon atoms among the groups substituted by a hexavalent group substituted with Z 1 , Z 2 , Z 3 , Z 4 , Z 5 and Z 6 , etc .;
- the hexavalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by Y 14 is a monovalent group exemplified as the m-valent organic group represented by X 5 in the general formula (III-A).
- a trivalent aromatic ring-containing hydrocarbon group and a group in which these groups are substituted by those exemplified as the substituent of the group representing the m-valent organic group represented by X 5 in the general formula (III-A) And the like include hexavalent groups substituted with Z 1 , Z 2 , Z 3 , Z 4 , Z 5 and Z 6 , etc.
- Examples of the hexavalent heterocyclic group having 2 to 35 carbon atoms represented by Y 14 include monovalent to 3 exemplified as the m-valent organic group represented by X 5 in the general formula (III-A).
- the sum of d and k is not more than the number of substituents that can be taken by the ring A 1 .
- the sum of d and k is preferably smaller than the number of substituents that can be taken by the ring A 1 .
- the number of substituents that the ring A 1 can take is 6, and d + k ⁇ 6.
- the number of substituents that the ring A 1 can take is 4, and d + k ⁇ 4.
- ring A 2 is a six-membered alicyclic ring, aromatic ring or heterocyclic ring, and R 81 , R 82 , R 83 , R 84 and R 85 are a hydrogen atom, a halogen atom, a cyano group, or a hydroxyl group.
- Nitro group carboxyl group, alkyl group having 1 to 40 carbon atoms, aryl group having 6 to 20 carbon atoms, arylalkyl group having 7 to 20 carbon atoms, carbon atom Represents a heterocyclic ring-containing group of 2 to 20, or —O—R 62 , wherein at least one of R 81 , R 82 , R 83 , R 84 and R 85 is not a hydrogen atom, and R 62 represents the above general formula (Same as (III).)
- X 11 is a group represented by the above general formula (1), and R 86 , R 87 , R 88 and R 89 are a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, An alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, or an alkyl group having 2 to 20 carbon atoms.
- R 86 , R 87 , R 88 and R 89 is not a hydrogen atom
- R 62 is the same as in the above general formula (III)
- ring A 2 is (It is the same as general formula (IV).)
- R 91 , R 92 , R 93 and R 94 may have a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group or a substituent.
- Examples of the six-membered alicyclic, aromatic or heterocyclic ring represented by the ring A 2 in the general formula (IV) include those exemplified in the description of the ring A 1 in the general formula (III).
- Halogen atoms represented by R 81 , R 82 , R 83 , R 84 and R 85 an alkyl group having 1 to 40 carbon atoms which may have a substituent, and an aryl group having 6 to 20 carbon atoms
- Examples of the arylalkyl group having 7 to 20 carbon atoms and the heterocycle-containing group having 2 to 20 carbon atoms include those exemplified in the description of R 61 or R 62 in the general formula (III).
- the halogen atom represented by R 86 , R 87 , R 88 and R 89 an alkyl group having 1 to 40 carbon atoms which may have a substituent, and 6 to 6 carbon atoms
- the aryl group having 20 atoms, the arylalkyl group having 7 to 20 carbon atoms, and the heterocyclic group having 2 to 20 carbon atoms include those exemplified in the description of R 61 or R 62 in the general formula (III).
- Examples of the aryl group having 20 atoms, the arylalkyl group having 7 to 20 carbon atoms, and the heterocyclic group having 2 to 20 carbon atoms include those exemplified in the description of R 61 or R 62 in the general formula (III). It is done.
- the groups other than hydrogen atoms include alkyl groups having 1 to 20 carbon atoms, aryl groups having 6 to 10 carbon atoms, and 7 to 7 carbon atoms. 12 arylalkyl groups, heterocycle-containing groups having 2 to 10 carbon atoms, particularly any one of R 81 to R 85 is an alkyl group having 1 to 4 carbon atoms or a heterocycle-containing group having 2 to 10 carbon atoms
- R 62 preferably has the following substituents via —CO—O—.
- -Alkyl groups having 1 to 8 carbon atoms (particularly methyl, ethyl, propyl, iso-propyl, butyl, sec-butyl, tert-butyl, iso-butyl, amyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl) 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl) ⁇
- Arylalkyl groups having 7 to 10 carbon atoms especially benzyl groups
- Alkenyl groups having 2 to 6 carbon atoms (particularly propen-1-yl groups)
- Ring A 2 is preferably benzene or naphthalene
- groups other than hydrogen atoms include alkyl groups having 1 to 20 carbon atoms, aryl groups having 6 to 10 carbon atoms, and aryls having 7 to 12 carbon atoms.
- R 62 preferably has the following substituents via —CO—O—.
- Y 10 is preferably a sulfur atom, an aromatic ring-containing hydrocarbon group having 6 to 25 carbon atoms, or a heterocyclic ring-containing group having 2 to 21 carbon atoms, Z 1 and Z 2 may have a direct bond, —CO—O—, —O—
- groups other than hydrogen atoms include alkyl groups having 1 to 20 carbon atoms, aryl groups having 6 to 10 carbon atoms, and aryls having 7 to 12 carbon atoms.
- An alkyl group, a heterocycle-containing group having 2 to 10 carbon atoms, particularly any one of R 91 to R 94 being an alkyl group having 1 to 4 carbon atoms or a heterocycle-containing group having 2 to 10 carbon atoms Is preferred.
- R 62 preferably has the following substituents via —CO—O—.
- Y 10 in the general formula (1) is a sulfur atom, a divalent alkyl group having 1 to 20 carbon atoms, a carbon atom number of 6 to 25 aromatic ring-containing hydrocarbon groups, heterocycle-containing groups having 2 to 21 carbon atoms, or 2,4,8,
- Y 11 is a trivalent alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 10 carbon atoms, or 7 to 7 carbon atoms.
- arylalkyl groups or heterocycle-containing groups having 1 to 10 carbon atoms, particularly trivalent alkyl groups having 1 to 8 carbon atoms, aryl groups having 6 to 9 carbon atoms, or 2 to 2 carbon atoms 6 is preferably a heterocyclic-containing group
- Z 1 , Z 2 and Z 3 are preferably the same as Z 1 and Z 2
- Y 12 is preferably the same as Y 11 except that it is tetravalent
- Z 1 to Z 4 are preferably the same as Z 1 and Z 2
- Y 13 is preferably the same as Y 11 except that it is pentavalent
- Z 1 to Z 5 are preferably the same as Z 1 and Z 2
- Y 14 is preferably the same as Y 11 except that it is hexavalent
- Z 1 to Z 6 are preferably the same as Z 1 and Z 2 .
- the content of the latent additive (A) is preferably 0.001 to 20% by mass, more preferably 0.005 to 5% by mass.
- the polymerization initiator (B) used in the composition of the present invention contains one or more oxime ester compounds represented by the above general formula (I).
- the oxime ester compound represented by the general formula (I) has geometric isomers due to oxime double bonds, but these are not distinguished. That is, in the present specification, the compound represented by the above general formula (I) and the exemplified compound thereof represent a mixture of both or one of them, and are not limited to structures showing isomers.
- the number of carbon atoms represented by R 3 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 21 , R 22 , R 23 and R 24 is 1 to Examples of the alkyl group of 20 include, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s-butyl, t-butyl, amyl, isoamyl, t-amyl, hexyl, heptyl, octyl, isooctyl, 2-ethylhexyl, t -Octyl, nonyl, isononyl, decyl, isodecyl, undecyl, dodecyl, tetradecyl, hexadecyl, octadecyl, icosyl, cyclopentyl, cycl
- Examples of the aryl group having 6 to 30 carbon atoms represented by R 3 , R 11 , R 12 , R 13 , R 21 , R 22 , R 23 and R 24 in the general formula (I) include, for example, Phenyl, tolyl, xylyl, ethylphenyl, naphthyl, anthryl, phenanthrenyl, phenyl, biphenylyl, naphthyl, anthryl substituted with one or more of the above alkyl groups.
- Examples of the arylalkyl group having 7 to 30 carbon atoms represented by R 3 , R 11 , R 12 , R 13 , R 21 , R 22 , R 23 and R 24 in the general formula (I) include, for example, , Benzyl, ⁇ -methylbenzyl, ⁇ , ⁇ -dimethylbenzyl, phenylethyl and the like.
- heterocyclic group containing 2 to 20 carbon atoms represented by R 3 , R 11 , R 12 , R 13 , R 21 , R 22 , R 23 , and R 24 in the general formula (I) For example, pyridyl, pyrimidyl, furyl, thienyl, tetrahydrofuryl, dioxolanyl, benzoxazol-2-yl, tetrahydropyranyl, pyrrolidyl, imidazolidyl, pyrazolidyl, thiazolidyl, isothiazolidyl, oxazolidyl, isoxazolidyl, piperidyl, piperazyl, morpholinyl, etc. Or a group in which a divalent linking group is bonded to the 5- to 7-membered heterocyclic ring.
- R 4 and R 5 , R 5 and R 6, R 6 and R 7 , R 3 and R 7, and R 3 and R 8 can be combined to form a ring
- Preferred examples include 5- to 7-membered rings such as cyclopentane ring, cyclohexane ring, cyclopentene ring, benzene ring, piperidine ring, morpholine ring, lactone ring, and lactam ring.
- R 13 , R 21 , R 22 and R 23 which may be substituted include fluorine, chlorine, bromine and iodine.
- oxime ester compounds represented by the general formula (I) those in which R 3 is an alkyl group having 1 to 12 carbon atoms or a heterocyclic ring-containing group having 2 to 12 carbon atoms are easy to produce. preferable.
- R 1 , R 2 , R 4 , R 5 , R 6 , R 7 , R 8 and n are the same as those in the general formula (I), and R 31 , R 32 , R 33 , R 34 And R 35 are each independently R 11 , OR 11 , SR 11 , COR 11 , CONR 15 R 16 , NR 12 COR 11 , OCOR 11 , COOR 14 , SCOR 11 , OCSR 11 , COSR 14 , CSOR 11 , hydroxyl group Represents a nitro group, CN or a halogen atom, and R 31 and R 32 , R 32 and R 33 , R 33 and R 34, and R 34 and R 35 may together form a ring. )
- R 31 and R 32, R 32 and R 33, examples of the ring R 33 and R 34 and R 34 and R 35 form together the, R 4 and R 5, R 5 and R 6 and R 6
- Examples of the ring that can be formed by combining R 3 and R 7 , R 3 and R 7, and R 3 and R 8 include the same rings as those listed above.
- R 1 is an alkyl group having 1 to 12 carbon atoms or an arylalkyl group having 7 to 15 carbon atoms, or R 1 is R 11 or OR 11.
- R 11 is preferably an aryl group having 6 to 12 carbon atoms or an alkyl group having 1 to 8 carbon atoms because of high solvent solubility, and one wherein R 2 is a methyl group, an ethyl group or a phenyl group.
- R 4 to R 7 are each independently a hydrogen atom, a cyano group or OR 11
- R 11 is an alkyl group having 1 to 8 carbon atoms having a hydroxyl group.
- a hydrogen atom or a cyano group particularly a hydrogen atom is preferable because it is easy to synthesize
- R 8 is preferably a hydrogen atom because it is easy to synthesize. Therefore, the above general formula (VI In I), at least one of R 31 to R 35 is a nitro group, CN, a halogen atom or COR 11 , and R 11 is an aryl group having 6 to 12 carbon atoms or an alkyl group having 1 to 8 carbon atoms.
- R 31 to R 35 is a nitro group, CN or a halogen atom, and particularly preferred are those wherein R 33 is a nitro group, CN or a halogen atom.
- oxime ester compound of the present invention represented by the above general formula (I) include the following compound Nos. 1-No. 214.
- the present invention is not limited by the following compounds.
- the polymerization initiator (B) can be used by mixing a plurality of oxime ester compounds represented by the above general formula (I), and used together with the oxime ester compound represented by the following general formula (II). You can also
- R 101 and R 102 are each independently a hydrogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylalkyl having 7 to 20 carbon atoms.
- R 103 and R 104 are each independently a halogen atom, nitro group, cyano group, hydroxyl group, carboxyl group, R 105 , OR 106 , SR 107 , NR 108 R 109 , COR 110 , SOR 111 , SO 2 R 112 or CONR 113 R 114 , R 103 and R 104 may be bonded to each other to form a ring, R 103 to each other, R 104 to each other may be bonded to each other to form a ring, X 11 represents an oxygen atom, a sulfur atom, a selenium atom, CR 115 R 116 , CO, NR 117 or PR 118 , X 12 represents a single bond or CO, R105 , R106 , R107 , R108 , R109 , R110 , R111 , R112 , R113 , R114 ,
- the alkyl group having 1 to 20 atoms may be linear, branched, cyclic, linear and ring combinations, or branched and ring combinations, R 101, R 102, R 105 , R 106, R 107, R 108, R 109, R 110, R 111, R 112, R 113, R 114, carbon in R 115, R 116, R 117 and R 118
- a polymerization initiator other than the polymerization initiator represented by the general formula (II) can also be used.
- other polymerization initiators preferred are acetophenone compounds, benzyl compounds, benzophenone compounds, thioxanthone compounds, bisimidazole compounds, acridine compounds, acylphosphine compounds, and the like.
- acetophenone compound examples include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 4′-isopropyl-2-hydroxy-2-methylpropiophenone, 2-hydroxymethyl- 2-methylpropiophenone, 2,2-dimethoxy-1,2-diphenylethane-1-one, p-dimethylaminoacetophenone, p-tertiarybutyldichloroacetophenone, p-tertiarybutyltrichloroacetophenone, p-azidoben Salacetophenone, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropanone-1, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) ) -Butanone-1, benzo In, benzoin methyl ether, benzoin ethyl ether, benzoin is
- benzyl compound examples include benzyl.
- benzophenone compounds include benzophenone, methyl o-benzoylbenzoate, Michler's ketone, 4,4′-bisdiethylaminobenzophenone, 4,4′-dichlorobenzophenone, 4-benzoyl-4′-methyldiphenyl sulfide, and the like. It is done.
- thioxanthone compound examples include thioxanthone, 2-methylthioxanthone, 2-ethylthioxanthone, 2-chlorothioxanthone, 2-isopropylthioxanthone, and 2,4-diethylthioxanthone.
- hexaarylbisimidazole hexaarylbisimidazole (HABI, a dimer of triaryl-imidazole) can be used.
- HABI a dimer of triaryl-imidazole
- 2,2′-bis (2-chlorophenyl) -4 , 4 ', 5,5'-tetrakis (4-ethoxycarbonylphenyl) -1,2'-biimidazole 2,2'-bis (2-bromophenyl) -4,4', 5,5'-tetrakis (-Ethoxycarbonylphenyl) -1,2'-biimidazole, 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenyl-1,2'-biimidazole, 2,2′-bis (2,4-dichlorophenyl) -4,4 ′, 5,5′-tetraphenyl-1,2′
- acridine compounds include acridine, 9-phenylacridine, 9- (p-methylphenyl) acridine, 9- (p-ethylphenyl) acridine, 9- (p-iso-propylphenyl) acridine, 9- (p -N-butylphenyl) acridine, 9- (p-tert-butylphenyl) acridine, 9- (p-methoxyphenyl) acridine, 9- (p-ethoxyphenyl) acridine, 9- (p-acetylphenyl) acridine 9- (p-dimethylaminophenyl) acridine, 9- (p-cyanophenylphenyl) acridine, 9- (p-chlorophenyl) acridine, 9- (p-bromophenyl) acridine, 9--
- acylphosphine compounds examples include 2,4,6-trimethylbenzoyldiphenylphosphine oxide (Lucirin TPO; manufactured by BASF), isobutyryl-methylphosphinic acid methyl ester, isobutyryl-phenylphosphinic acid methyl ester, and pivaloyl-phenylphosphinic acid methyl.
- Lucirin TPO 2,4,6-trimethylbenzoyldiphenylphosphine oxide
- isobutyryl-methylphosphinic acid methyl ester isobutyryl-phenylphosphinic acid methyl ester
- pivaloyl-phenylphosphinic acid methyl examples include 2,4,6-trimethylbenzoyldiphenylphosphine oxide (Lucirin TPO; manufactured by BASF), isobutyryl-methylphosphinic acid methyl ester, isobutyryl-phenylphosphinic acid methyl ester, and pivaloyl-phen
- the total content of the polymerization initiators is preferably 0.1 to 30% by mass, particularly preferably 0.5 to 10% by mass, based on the solid content of the composition of the present invention. If the content of the polymerization initiator is less than 0.1% by mass, curing by exposure may be insufficient, and if it is more than 30% by mass, the initiator may be precipitated in the resin composition.
- the proportion of the oxime ester compound represented by the general formula (I) in 100 parts by mass of the whole polymerization initiator is preferably 25 parts by mass or more, more preferably 50 parts by mass or more, and 75 parts by mass or more. Particularly preferred.
- the composition of the present invention is a mixture of a latent antioxidant (A) and a polymerization initiator (B), a resin, a photopolymerizable unsaturated monomer and, if necessary, a solvent, an inorganic compound, a coloring material, and the like. It can also be used as a photosensitive composition.
- the resin is not particularly limited as long as it is compatible with the polymerization initiator and the photopolymerizable unsaturated monomer.
- a repeating unit derived from the photopolymerizable unsaturated monomer may be used. Examples thereof include a homopolymer or a copolymer. Among them, methacrylic acid ester copolymers, polyvinyl alcohol / polyvinyl ether / polyvinyl ester copolymers, unsaturated polyesters and the like are preferable because they have good compatibility with the photopolymerizable unsaturated monomers, and have an acid value. Is preferable from the viewpoint of photolithography.
- Examples of the unsaturated monobasic acid that acts on the epoxy group of the bisphenol type epoxy compound or novolak type epoxy compound include acrylic acid, methacrylic acid, crotonic acid, cinnamic acid, sorbic acid, hydroxyethyl methacrylate / malate, hydroxyethyl acrylate / Examples thereof include malate, hydroxypropyl methacrylate / malate, hydroxypropyl acrylate / malate, and dicyclopentadiene / malate.
- the polybasic acid anhydride to be acted after the unsaturated monobasic acid is allowed to act is biphenyltetracarboxylic dianhydride, tetrahydrophthalic anhydride, succinic anhydride, maleic anhydride, trimellitic anhydride , Pyromellitic anhydride, 2,2'-3,3'-benzophenone tetracarboxylic anhydride, ethylene glycol bisanhydro trimellitate, glycerol tris anhydro trimellitate, hexahydro phthalic anhydride, methyl tetrahydro phthalic anhydride Acid, nadic anhydride, methyl nadic anhydride, trialkyltetrahydrophthalic anhydride, hexahydrophthalic anhydride, 5- (2,5-dioxotetrahydrofuryl) -3-methyl-3-cyclohexene-1,2- Dicarboxylic anhydride, trialkyltetra
- the reaction molar ratio of the epoxy compound, the unsaturated monobasic acid and the polybasic acid anhydride is preferably as follows. That is, in an epoxy adduct having a structure in which 0.1 to 1.0 carboxyl groups of the unsaturated monobasic acid are added to one epoxy group of the epoxy compound, the hydroxyl group 1 of the epoxy adduct is It is preferable that the ratio of the acid anhydride structure of the polybasic acid anhydride is 0.1 to 1.0. Reaction of the said epoxy compound, the said unsaturated monobasic acid, and the said polybasic acid anhydride can be performed in accordance with a conventional method.
- a monofunctional or polyfunctional epoxy compound can be further used.
- the resin having the acid value preferably has a solid acid value in the range of 5 to 120 mgKOH / g, and the amount of the monofunctional or polyfunctional epoxy compound used is selected so as to satisfy the acid value. preferable.
- Examples of the monofunctional epoxy compound include glycidyl methacrylate, methyl glycidyl ether, ethyl glycidyl ether, propyl glycidyl ether, isopropyl glycidyl ether, butyl glycidyl ether, isobutyl glycidyl ether, t-butyl glycidyl ether, pentyl glycidyl ether, hexyl glycidyl ether, heptyl Glycidyl ether, octyl glycidyl ether, nonyl glycidyl ether, decyl glycidyl ether, undecyl glycidyl ether, dodecyl glycidyl ether, tridecyl glycidyl ether, tetradecyl glycidyl ether, pentadecy
- the polyfunctional epoxy compound it is preferable to use one or more selected from the group consisting of bisphenol type epoxy compounds and glycidyl ethers because an alkali-developable photosensitive composition with better characteristics can be obtained.
- the bisphenol-type epoxy compound the epoxy compound represented by the general formula (1) can be used, and for example, a bisphenol-type epoxy compound such as a hydrogenated bisphenol-type epoxy compound can also be used.
- glycidyl ethers examples include ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, 1,8-octanediol diglycidyl ether, 1 , 10-decanediol diglycidyl ether, 2,2-dimethyl-1,3-propanediol diglycidyl ether, diethylene glycol diglycidyl ether, triethylene glycol diglycidyl ether, tetraethylene glycol diglycidyl ether, hexaethylene glycol diglycidyl ether 1,4-cyclohexanedimethanol diglycidyl ether, 1,1,1-tri (glycidyloxymethyl) propane, 1,1,1-tri (g Glycidyl oxymethyl) ethane, 1,1,1-tri (g
- novolac epoxy compounds such as phenol novolac epoxy compounds, biphenyl novolac epoxy compounds, cresol novolac epoxy compounds, bisphenol A novolac epoxy compounds, dicyclopentadiene novolac epoxy compounds; 3,4-epoxy-6-methyl Cycloaliphatic epoxy such as cyclohexylmethyl-3,4-epoxy-6-methylcyclohexanecarboxylate, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 1-epoxyethyl-3,4-epoxycyclohexane Compound: Glycidyl esters such as diglycidyl phthalate, diglycidyl tetrahydrophthalate, glycidyl dimer, tetraglycidyl diamino Glycidylamines such as phenylmethane, triglycidyl-p-aminophenol and N, N-diglycidylaniline; hetero
- resins having an acid value unsaturated polybasic acids and polyfunctional acrylates having an acid value are preferred, and polyfunctional acrylates having an acid value are particularly preferred from the viewpoints of compatibility, alkali developability and heat resistance.
- resin having an acid value commercially available resins can be used.
- SPC-1000, SPC-3000 manufactured by Showa Denko
- AX3-BX, AX3-RD1, AX3-RD2 manufactured by Nippon Shokubai Co., Ltd.
- JET2000 manufactured by Osaka Organic Chemical Co., Ltd.
- the photopolymerizable unsaturated monomer is not particularly limited, and those conventionally used in photosensitive compositions can be used.
- A4 methyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, (t-butyl) (meth) acrylate, cyclohexyl (meth) acrylate, n-octyl (meth) acrylate, ( Isooctyl (meth) acrylate, isononyl (meth) acrylate, stearyl (meth) acrylate, lauryl (meth) acrylate, methoxyethyl (meth) acrylate, dimethylaminomethyl (meth) acrylate, dimethyl (meth) acrylate Aminoethyl, aminopropyl (meth) acrylate, dimethylaminopropyl (meth) acrylate, ethoxyethyl (meth) acrylate, poly (ethoxy) ethyl (meth) acrylate, butoxyethoxyethyl (
- the photopolymerizable unsaturated monomer in particular, it is possible to use unsaturated monobasic acid and polyhydric alcohol or polyhydric phenol ester in terms of curability and chromaticity characteristics. To preferred.
- the total amount of the resin and the polymerizable unsaturated monomer is preferably 20 to 80% by mass in the solid content of the composition of the present invention. More preferably, it is 30 to 70% by mass. If the total content of both is less than 20% by mass, the cured film may not be sufficiently hardened. If it is more than 80% by mass, the colorant may be small and the color characteristics may be insufficient.
- the solvent is usually a solvent capable of dissolving or dispersing each of the above components (polymerization initiator, resin, photopolymerizable unsaturated monomer, etc.) as necessary, for example, methyl ethyl ketone, methyl amyl ketone, diethyl ketone.
- Ketones such as acetone, methyl isopropyl ketone, methyl isobutyl ketone, cyclohexanone, 2-heptanone; ethers such as ethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, dipropylene glycol dimethyl ether Solvents; ester solvents such as methyl acetate, ethyl acetate, acetic acid-n-propyl, isopropyl acetate, n-butyl acetate, cyclohexyl acetate, ethyl lactate, dimethyl succinate, texanol; ethylene glycol monomethyl ether, ethylene glycol mono Cellosolve solvents such as tilether; alcohol solvents such as methanol, ethanol, iso- or n-propanol, iso- or n-butanol, amyl alcohol
- ketones, ether ester solvents and the like particularly propylene glycol-1-monomethyl ether-2-acetate (PGMEA), cyclohexanone and the like are preferable because the compatibility between the resist and the polymerization initiator is good in the colored composition.
- PMEA propylene glycol-1-monomethyl ether-2-acetate
- cyclohexanone cyclohexanone
- the amount of the solvent used is preferably such that the concentration of the composition other than the solvent is 5 to 30% by mass, and if it is less than 5% by mass, the film thickness is increased. It is difficult to increase the thickness and it is not preferable because it cannot sufficiently absorb light of a desired wavelength.
- the content exceeds 30% by mass, the storage stability of the composition due to the precipitation of the composition is decreased, and the viscosity is improved. Is unfavorable because of lowering.
- the inorganic compound examples include nickel oxide, iron oxide, iridium oxide, titanium oxide, zinc oxide, magnesium oxide, calcium oxide, potassium oxide, silica, alumina, and other metal oxides; layered clay mineral, miloli blue, calcium carbonate, Magnesium carbonate, cobalt, manganese, glass powder (especially glass frit), mica, talc, kaolin, ferrocyanide, various metal sulfates, sulfides, selenides, aluminum silicate, calcium silicate, aluminum hydroxide, platinum, Gold, silver, copper, etc. are mentioned. Among these, glass frit, titanium oxide, silica, layered clay mineral, silver and the like are preferable.
- the content of the inorganic compound is preferably 0.1 to 1000 parts by mass, more preferably 10 to 800 parts by mass with respect to 100 parts by mass of the resin.
- These inorganic compounds can be used alone or in combination of two or more.
- inorganic compounds are used, for example, as fillers, antireflection agents, conductive agents, stabilizers, flame retardants, mechanical strength improvers, special wavelength absorbers, ink repellents, and the like.
- a dispersant for dispersing a colorant and / or an inorganic compound can be added.
- the dispersing agent is not limited as long as it can disperse and stabilize a coloring material or an inorganic compound, and a commercially available dispersing agent such as BYK series manufactured by BYK Chemie Corporation can be used.
- a polymer dispersant comprising a polyester, polyether, or polyurethane having a basic functional group, a nitrogen atom as the basic functional group, and the functional group having a nitrogen atom is an amine and / or a quaternary salt thereof.
- those having an amine value of 1 to 100 mgKOH / g are preferably used.
- coloring material examples include pigments, dyes, and natural pigments. These color materials can be used alone or in admixture of two or more.
- the pigment examples include nitroso compounds; nitro compounds; azo compounds; diazo compounds; xanthene compounds; quinoline compounds; anthraquinone compounds; coumarin compounds; phthalocyanine compounds; isoindolinone compounds; Compound; perylene compound; diketopyrrolopyrrole compound; thioindigo compound; dioxazine compound; triphenylmethane compound; quinophthalone compound; naphthalene tetracarboxylic acid; azo dye, metal complex compound of cyanine dye; lake pigment; Carbon black obtained by the method, or carbon black such as acetylene black, ketjen black or lamp black; Prepared by coating or coating with an epoxy resin, carbon black previously dispersed with a resin in a solvent and adsorbed with 20 to 200 mg / g of resin, carbon black treated with an acidic or alkaline surface, average Graphite having a particle size of 8 nm or more and a DBP oil absorption of 90
- Graphite Graphitized carbon black, activated carbon, carbon fiber, carbon nanotube, carbon microcoil, carbon nanohorn, carbon aerogel, fullerene; aniline black, pigment black 7, titanium black; chromium oxide green, miloli blue, cobalt green, cobalt blue, manganese series , Ferrocyanide Organic or inorganic such as phosphate ultramarine, bitumen, ultramarine, cerulean blue, pyridian, emerald green, lead sulfate, yellow lead, zinc yellow, red bean (red iron (III) oxide), cadmium red, synthetic iron black, amber Pigments can be used. These pigments can be used alone or in combination.
- pigments can also be used as the pigment, for example, Pigment Red 1, 2, 3, 9, 10, 14, 17, 22, 23, 31, 38, 41, 48, 49, 88, 90, 97, 112, 119, 122, 123, 144, 149, 166, 168, 169, 170, 171, 177, 179, 180, 184, 185, 192, 200, 202, 209, 215, 216, 217, 220, 223, 224, 226, 227, 228, 240, 254; Pigment Orange 13, 31, 34, 36, 38, 43, 46, 48, 49, 51, 52, 55, 59, 60, 61, 62, 64, 65, 71; Pigment Yellow 1, 3, 12, 13, 14, 16, 17, 20, 24, 55, 60, 73, 81, 83, 86, 93, 95, 9 98, 100, 109, 110, 113, 114, 117, 120, 125, 126, 127, 129, 137, 138, 139, 147, 148,
- dyes As the above dyes, azo dyes, anthraquinone dyes, indigoid dyes, triarylmethane dyes, xanthene dyes, alizarin dyes, acridine dyes stilbene dyes, thiazole dyes, naphthol dyes, quinoline dyes, nitro dyes, indamine dyes, oxazine dyes, phthalocyanine dyes And dyes such as cyanine dyes, and a plurality of these may be used in combination.
- the content of the coloring material is preferably 50 to 350 parts by mass, more preferably 100 to 250 parts by mass with respect to 100 parts by mass of the resin.
- a thermal polymerization inhibitor such as p-anisole, hydroquinone, pyrocatechol, t-butylcatechol, phenothiazine
- plasticizer adhesion promoter
- filler Leveling agent; Surface modifier; Antioxidant; UV absorber; Dispersion aid; Aggregation inhibitor; Catalyst; Effect accelerator; Crosslinking agent; Thickener; Chain transfer agent; Coupling agents; conventional additives such as melamine can be added.
- composition of the present invention optional components other than the latent additive (A) and the polymerization initiator (B) (however, the other photopolymerization initiator, resin, photopolymerizable unsaturated monomer, inorganic
- the amount of the compound is appropriately selected depending on the purpose of use and is not particularly limited, but is preferably 50 parts by mass or less based on 100 parts by mass of the resin. To do.
- cured material can also be improved by using another organic polymer with the polymeric compound which has the said ethylenically unsaturated bond.
- the organic polymer include polystyrene, polymethyl methacrylate, methyl methacrylate-ethyl acrylate copolymer, poly (meth) acrylic acid, styrene- (meth) acrylic acid copolymer, (meth) acrylic acid-methyl methacrylate.
- Copolymer ethylene-vinyl chloride copolymer, ethylene-vinyl copolymer, polyvinyl chloride resin, ABS resin, nylon 6, nylon 66, nylon 12, urethane resin, polycarbonate polyvinyl butyral, cellulose ester, polyacrylamide, saturated
- polyester phenol resin, phenoxy resin, polyamideimide resin, polyamic acid resin, epoxy resin, etc.
- polystyrene, (meth) acrylic acid-methyl methacrylate copolymer, and epoxy resin are preferred. Arbitrariness. When another organic polymer is used, the amount used is preferably 10 to 500 parts by mass with respect to 100 parts by mass of the resin.
- the polymerization initiator (B) used in the composition of the present invention one that emits light having a wavelength of 300 to 450 nm can be used.
- one that emits light having a wavelength of 300 to 450 nm can be used.
- ultrahigh pressure mercury, mercury Steam arc, carbon arc, xenon arc, etc. can be used.
- the exposure time to the energy ray depends on the intensity of the energy ray, the coating thickness and the polymerizable organic compound, but usually about 0.1 to 10 seconds is sufficient. However, it is preferable to take a longer irradiation time for a relatively thick coating. From 0.1 seconds to several minutes after irradiation with energy rays, most of the compositions are dry to the touch by polymerization. However, in order to accelerate the polymerization, it is preferable in some cases to use heat or thermal energy by a thermal head or the like.
- a pattern can be formed by the following steps. That is, (1) a step of forming a coating film of the composition of the present invention on a substrate, (2) a step of irradiating the coating film with a radiation having a predetermined pattern shape, (3) after exposure It is preferably formed by a baking step, (4) a step of developing the film after exposure, and (5) a step of heating the film after development.
- a multi-tone mask such as a halftone mask or a gray scale mask can be used.
- the composition of the present invention is excellent in sensitivity and transparency. Moreover, the composition of this invention can form the molded object and cured film excellent in the brightness
- molded bodies and cured films are used for color filters, overcoats, spacers, microlens arrays, and transparent insulating films, for example.
- composition of the present invention include optical filters, paints, coating agents, lining agents, adhesives, printing plates, insulating varnishes, insulating sheets, laminates, printed boards, semiconductor devices, LED packages, Sealants for liquid crystal inlets, organic EL, optical elements, electrical insulation, electronic parts, separation membranes, molding materials, putty, glass fiber impregnating agents, sealants, for semiconductors and solar cells Passivation films such as thin film transistors (TFTs), liquid crystal display devices, organic EL display devices, interlayer insulating films used for printed circuit boards, surface protective films, printed circuit boards, color televisions, PC monitors, portable information terminals, CCD image sensors Color filter, electrode material for plasma display panel, printing ink, dental composition, resin for stereolithography, both liquid and dry film, micro mechanical parts Glass fiber cable coating, holographic recording material, magnetic recording material, optical switch, plating mask, etching mask, screen printing stencil, touch panel such as transparent conductive film, MEMS element, nanoimprint material, 2D and 3D of semiconductor package Used
- Examples 1-1 to 1-9 and Comparative Examples 1-1 to 1-10 Production and Evaluation of Compositions
- Compositions were prepared according to the formulations shown in [Table 1] to [Table 3]. This was spin-coated on a glass substrate (900 rpm, 10 seconds), pre-baked at 90 ° C. for 90 seconds using a hot plate, and exposed using a high-pressure mercury lamp as a light source (20 mJ / cm 2 to 200 mJ / 10 divided into 20mJ / cm 2 to cm 2). A 2.5% by mass aqueous sodium carbonate solution was used as a developing solution, developed for 40 seconds with a spin developing machine, washed well with water, and post-baked at 230 ° C. for 30 minutes using an oven to fix the pattern.
- Examples 2-1 to 2-3 and Comparative Examples 2-1 to 2-15 Preparation of colored compositions Colored polymerizable compositions were prepared by preparing colored compositions according to the formulations of [Table 3A] to [Table 3C]. (Examples 2-1 to 2-3 and Comparative Examples 2-1 to 2-15) were obtained.
- C-1 SPC-1000 (manufactured by Showa Denko KK, PGMEA solution with a solid content of 29%)
- C-2 Kayalad DPHA polyfunctional acrylate; manufactured by Nippon Kayaku Co., Ltd.
- C-4 Blue pigment dispersion (15 parts by weight of CI Pigment Blue 15: 6 as a colorant, BYK161 (BYK) manufactured by BYK) as a dispersant 12.5 parts by mass (solid content concentration: 40% by mass), and 72.5 parts by mass of propylene glycol monomethyl ether acetate as a solvent.
- C-5 SPC-3000 (manufactured by Showa Denko KK, PGMEA solution having a solid content of 42.7% by mass)
- C-6 Red pigment dispersion (15 parts by mass of CI Pigment Red 254 as a colorant, 8.0 parts by mass of Ajisper PB821 (manufactured by Ajinomoto Fine Techno) as a dispersant, and 77.0 parts by mass of PGMEA as a solvent)
- C-7 green pigment dispersion (15 parts by mass of CI Pigment Green 58 as a colorant, 7.0 parts by mass (by Big Chemie Japan) BYK-LPN6919 as a dispersant, 40% by mass of solid), It was prepared by processing with a bead mill using 78.0 parts by weight of PGMEA.
- the initial film thickness is the film thickness after pre-baking and before post-baking.
- Residual film ratio (%) (pattern height after post-baking / initial film thickness) ⁇ 100
- a green coloring pattern was obtained in the same manner as above.
- a blue colored pattern was obtained.
- the pattern width of the photomask opening 30 ⁇ m of these formed patterns was measured.
- the composition of the present invention has high transmittance and high sensitivity by using the specific oxime ester compound as the component (B) in combination with the latent antioxidant as the component (A). It is clear that both can be achieved.
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Abstract
Description
R11、R12及びR13は、それぞれ独立に、水素原子、炭素原子数1~20のアルキル基、炭素原子数6~30のアリール基、炭素原子数7~30のアリールアルキル基又は炭素原子数2~20の複素環含有基を表し、
R11、R12及びR13で表わされる基の水素原子は、更にR21、OR21、COR21、SR21、NR22R23、CONR22R23、NR22OR23、NCOR22OCOR23、NR22COR21、OCOR21、COOR21、SCOR21、OCSR21、COSR21、CSOR21、水酸基、ニトロ基、CN、ハロゲン原子、又はCOOR21で置換されている場合もあり、
R21、R22及びR23は、それぞれ独立に、水素原子、炭素原子数1~20のアルキル基、炭素原子数6~30のアリール基、炭素原子数7~30のアリールアルキル基又は炭素原子数2~20の複素環含有基を表し、
R21、R22及びR23で表される基の水素原子は、更に水酸基、ニトロ基、CN、ハロゲン原子、水酸基又はカルボキシル基で置換されている場合もあり、
R11、R12、R13、R21、R22及びR23で表される基のアルキレン部分のメチレン基は、-O-、-S-、-COO-、-OCO-、-OCOO-、-CONR24-、-NR24-、-NR24CO-、-NR24COO-、-OCONR24-、-SCO-、-COS-、-OCS-又は-SCOO-により置き換えられている場合もあり、
R24は、水素原子、炭素原子数1~20のアルキル基、炭素原子数6~30のアリール基、炭素原子数7~30のアリールアルキル基又は炭素原子数2~20の複素環含有基を表し、
R11、R12、R13、R21、R22、R23及びR24で表される基のアルキル部分は、分岐側鎖がある場合もあり、環状アルキルである場合もあり、
R3は、水素原子、炭素原子数1~20のアルキル基、炭素原子数6~30のアリール基、炭素原子数7~30のアリールアルキル基又は炭素原子数2~20の複素環含有基を表し、R3で表される基のアルキル部分は、分岐側鎖がある場合もあり、環状アルキルである場合もあり、また、R3とR7、R3とR8、R4とR5、R5とR6及びR6とR7はそれぞれ一緒になって環を形成している場合もあり、
R3で表わされる基の水素原子は、更にR21、OR21、COR21、SR21、NR22R23、CONR22R23、NR22OR23、NCOR22OCOR23、NR22COR21、OCOR21、COOR21、SCOR21、OCSR21、COSR21、CSOR21、水酸基、ニトロ基、CN、ハロゲン原子、又はCOOR21で置換されている場合もあり、
R4、R5、R6及びR7は、それぞれ独立に、R11、OR11、SR11、COR14、CONR15R16、NR12COR11、OCOR11、COOR14、SCOR11、OCSR11、COSR14、CSOR11、水酸基、CN又はハロゲン原子を表し、R4とR5、R5とR6及びR6とR7はそれぞれ一緒になって環を形成している場合もあり、
R4、R5、R6及びR7で表わされる基の水素原子は、更にR21、OR21、COR21、SR21、NR22R23、CONR22R23、NR22OR23、NCOR22OCOR23、NR22COR21、OCOR21、COOR21、SCOR21、OCSR21、COSR21、CSOR21、水酸基、ニトロ基、CN、ハロゲン原子又はCOOR21で置換されている場合もあり、
R14、R15及びR16は、水素原子又は炭素原子数1~20のアルキル基を表し、
R14、R15及びR16で表される基のアルキル部分は、分岐側鎖がある場合もあり、環状アルキルである場合もあり、
R8は、R11、OR11、SR11、COR11、CONR12R13、NR12COR11、OCOR11、COOR11、SCOR11、OCSR11、COSR11、CSOR11、水酸基、CN又はハロゲン原子を表し、
nは、0又は1を表す。)
本発明の組成物に用いられる潜在性酸化防止剤(A)とは、常温或いはプリベーク工程では不活性であり、100~250℃で加熱するか、或いは酸/塩基触媒存在下で80~200℃で加熱することにより保護基が脱離して活性となるものであり、下記一般式(III)で表される骨格を有するものが、合成が容易で耐熱性が高く、本発明の効果が高いので好ましい。
R61は、それぞれ独立に、水素原子、ハロゲン原子、シアノ基、水酸基、ニトロ基、カルボキシル基、置換基を有している場合もある炭素原子数1~40のアルキル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基又は炭素原子数2~20の複素環含有基を表し、
R62は、それぞれ独立に、炭素原子数1~20のアルキル基、炭素原子数2~20のアルケニル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基、炭素原子数2~20の複素環含有基又はトリアルキルシリル基を表し、
R61及びR62で表されるアルキル基又はアリールアルキル基中のメチレン基は、炭素-炭素二重結合、-O-、-S-、-CO-、-O-CO-、-CO-O-、-O-CO-O-、-O-CO-O-、-S-CO-、-CO-S-、-S-CO-O-、-O-CO-S-、-CO-NH-、-NH-CO-、-NH-CO-O-、-NR'-、-S-S-又は-SO2-から選ばれた基を酸素原子が隣り合わない条件で組み合わせた基で置き換えていてもよく、R’は、水素原子又は炭素原子数1~8のアルキル基を表し、
複数のR61同士は結合してベンゼン環又はナフタレン環を形成している場合もあり、
dは、1~4の整数を表し、
kは、1~4の整数を表すが、dとkの合計は、環A1が取り得る置換基の数以下である。)
R61で表されるハロゲン原子としては、フッ素、塩素、臭素、ヨウ素が挙げられる(尚、以下の明細書中の記載において、ハロゲン原子は全て、上記と同様である)。
R61で表される炭素原子数1~40のアルキル基としては、メチル、エチル、プロピル、iso-プロピル、ブチル、sec-ブチル、tert-ブチル、iso-ブチル、アミル、iso-アミル、tert-アミル、シクロペンチル、ヘキシル、2-ヘキシル、3-ヘキシル、シクロヘキシル、4-メチルシクロヘキシル、ヘプチル、2-ヘプチル、3-ヘプチル、iso-ヘプチル、tert-ヘプチル、1-オクチル、iso-オクチル、tert-オクチル、アダマンチル等が挙げられ、R62で表される炭素原子数1~20のアルキル基としては、これらのアルキル基のうち、所定の炭素原子数を満たすものが挙げられ、
R61で表される炭素原子数1~40のアルキル基を置換する置換基としては、ビニル、アリル、アクリル、メタクリル等のエチレン性不飽和基;フッ素、塩素、臭素、ヨウ素等のハロゲン原子;アセチル、2-クロロアセチル、プロピオニル、オクタノイル、アクリロイル、メタクリロイル、フェニルカルボニル(ベンゾイル)、フタロイル、4-トリフルオロメチルベンゾイル、ピバロイル、サリチロイル、オキザロイル、ステアロイル、メトキシカルボニル、エトキシカルボニル、t-ブトキシカルボニル、n-オクタデシルオキシカルボニル、カルバモイル等のアシル基;アセチルオキシ、ベンゾイルオキシ等のアシルオキシ基;アミノ、エチルアミノ、ジメチルアミノ、ジエチルアミノ、ブチルアミノ、シクロペンチルアミノ、2-エチルヘキシルアミノ、ドデシルアミノ、アニリノ、クロロフェニルアミノ、トルイジノ、アニシジノ、N-メチル-アニリノ、ジフェニルアミノ,ナフチルアミノ、2-ピリジルアミノ、メトキシカルボニルアミノ、フェノキシカルボニルアミノ、アセチルアミノ、ベンゾイルアミノ、ホルミルアミノ、ピバロイルアミノ、ラウロイルアミノ、カルバモイルアミノ、N,N-ジメチルアミノカルボニルアミノ、N,N-ジエチルアミノカルボニルアミノ、モルホリノカルボニルアミノ、メトキシカルボニルアミノ、エトキシカルボニルアミノ、t-ブトキシカルボニルアミノ、n-オクタデシルオキシカルボニルアミノ、N-メチル-メトキシカルボニルアミノ、フェノキシカルボニルアミノ、スルファモイルアミノ、N,N-ジメチルアミノスルホニルアミノ、メチルスルホニルアミノ、ブチルスルホニルアミノ、フェニルスルホニルアミノ等の置換アミノ基;スルホンアミド基、スルホニル基、カルボキシル基、シアノ基、スルホ基、水酸基、ニトロ基、メルカプト基、イミド基、カルバモイル基、スルホンアミド基、ホスホン酸基、リン酸基又はカルボキシル基、スルホ基、ホスホン酸基、リン酸基の塩等が挙げられる。
R61及びR62で表される炭素原子数6~20のアリール基としては、フェニル、ナフチル、アントラセニル、フェナントリル、フルオレニル、インデニル、2-メチルフェニル、3-メチルフェニル、4-メチルフェニル、4-ビニルフェニル、3-iso-プロピルフェニル、4-iso-プロピルフェニル、4-ブチルフェニル、4-iso-ブチルフェニル、4-tert-ブチルフェニル、4-ヘキシルフェニル、4-シクロヘキシルフェニル、4-オクチルフェニル、4-(2-エチルヘキシル)フェニル、4-ステアリルフェニル、2,3-ジメチルフェニル、2,4-ジメチルフェニル、2,5-ジメチルフェニル、2,6-ジメチルフェニル、3,4-ジメチルフェニル、3,5-ジメチルフェニル、2,4-ジ-tert-ブチルフェニル、2,5-ジ-tert-ブチルフェニル、2,6-ジ-tert-ブチルフェニル、2,4-ジ-tert-ペンチルフェニル、2,5-ジ-tert-アミルフェニル、2,5-ジ-tert-オクチルフェニル、2,4-ジクミルフェニル、4-シクロヘキシルフェニル、(1,1’-ビフェニル)-4-イル、2,4,5-トリメチルフェニル、フェロセニル等が挙げられ、
R61及びR62で表される炭素原子数7~20のアリールアルキル基としては、ベンジル、1-メチル-1-フェニルエチル、1-ナフチルメチル、9-アントラセニルメチル、9-フルオレニル、3-フェニルプロピル、メチル-2-フェニルプロパン-2-イル、ジフェニルメチル、トリフェニルメチル、フェネチル、スチリル、シンナミル等が挙げられ、
R61及びR62で表される炭素原子数2~20の複素環含有基としては、ピリジン環、ピリミジン環、ピリダジン環、ピペリジン環、ピラン環、ピラゾリン環、トリアジン環、ピロリン環、キノリン環、イソキノリン環、イミダゾリン環、ベンゾイミダゾリン環、トリアゾリン環、フラン環、ベンゾフラン環、チアジアゾリン環、チアゾリン環、ベンゾチアゾリン環、チオフェン環、オキサゾリン環、ベンゾオキサゾリン環、イソチアゾリン環、イソオキサゾリン環、インドール環、ピロリジン環、ピペリドン環、ジオキサン環等の複素環とメチレン鎖を組み合わせた基が挙げられ、
R62で表されるトリアルキルシリル基としては、トリメチルシラン、トリエチルシラン、エチルジメチルシラン等の炭素原子数1~6のアルキル基(3つのアルキル基は同一でも異なってもよい)で置換されたシリル基が挙げられる。
R’で表される炭素原子数1~8のアルキル基としては、R61で表される上記アルキル基のうち、所定の炭素原子数を満たすものが挙げられる。
一般式(III)で表される骨格を有する化合物の中でも、R61が水素原子、炭素原子数1~8のアルキル基又は炭素原子数6~12のアリール基であるものが合成が容易なため好ましく、
また、R62が、炭素原子数1~8のアルキル基の酸素原子側の末端に-CO-O-が結合しているものが潜在性添加剤として効率的に機能を発現するので好ましい。
但し、X5が窒素原子、リン原子又は下記(III-a)若しくは(III-b)で表される基の場合、mは3であり、X5が酸素原子又は硫黄原子、>C=O、-NH-CO-、-CO-NH-又は>NR63の場合、mは2であり、X5が-OR63、-SR63又は-NR63R64の場合、mは1であり、X5は、A1と一緒になって環を形成している場合もある。
mが2価のものとして、メチレン、エチレン、プロピレン、ブチレン、ブチルジイル等のアルキレン;前記アルキレンのメチレン鎖が-O-、-S-、-CO-O-、-O-CO-で置き換えられたもの;エタンジオール、プロパンジオール、ブタンジオール、ペンタンジオール、ヘキサンジオール等のジオールの残基;エタンジチオール、プロパンジチオール、ブタンジチオール、ペンタンジチオール、ヘキサンジチオール等のジチオールの残基及びこれらの基が後述する置換基により置換された基等が挙げられ、
mが3価のものとして、例えば、プロピリジン、1,1,3-ブチリジン等のアルキリジン及びこれらの基が後述する置換基により置換された基が挙げられ、
mと同数の価数を有する置換基を有している場合もある炭素原子数6~35の1価の芳香環含有炭化水素基としては、mが1価のものとして、ベンジル、フェネチル、ジフェニルメチル、トリフェニルメチル、スチリル、シンナミル等のアリールアルキル基;フェニル、ナフチル等のアリール基;フェノキシ、ナフチルオキシ等のアリールオキシ基;フェニルチオ、ナフチルチオ等のアリールチオ基及びこれらの基が後述する置換基により置換された基等が挙げられ、
mが2価のものとして、フェニレン、ナフチレン等のアリーレン基;カテコール、ビスフェノール等の二官能フェノールの残基;2,4,8,10-テトラオキサスピロ[5,5]ウンデカン等及びこれらの基が後述する置換基により置換された基が挙げられ、
mが3価のものとして、フェニル-1,3,5-トリメチレン等及びこれらの基が後述する置換基により置換された基が挙げられ、
mと同数の価数を有する置換基を有している場合もある炭素原子数2~35の複素環含有基としては、mが1価のものとして、ピリジル、ピリミジル、ピリダジル、ピペリジル、ピラニル、ピラゾリル、トリアジル、ピロリル、キノリル、イソキノリル、イミダゾリル、ベンゾイミダゾリル、トリアゾリル、フリル、フラニル、ベンゾフラニル、チエニル、チオフェニル、ベンゾチオフェニル、チアジアゾリル、チアゾリル、ベンゾチアゾリル、オキサゾリル、ベンゾオキサゾリル、イソチアゾリル、イソオキサゾリル、インドリル、2-ピロリジノン-1-イル、2-ピペリドン-1-イル、2,4-ジオキシイミダゾリジン-3-イル、2,4-ジオキシオキサゾリジン-3-イル、ベンゾトリアゾイル等及びこれらの基が後述する置換基により置換された基等が挙げられ、
mが2価のものとして、ピリジン環、ピリミジン環、ピペリジン環、ピペラジン環、トリアジン環、フラン環、チオフェン環、インドール環等を有する基及びこれらの基が後述する置換基により置換された基が挙げられ、
mが3価のものとしては、イソシアヌル環を有する基、トリアジン環を有する基及びこれらの基が後述する置換基により置換された基が挙げられ、
R63及びR64で表される置換基を有している場合もある炭素原子数1~35の脂肪族炭化水素基としては、上記X5で表される脂肪族炭化水素基又は脂肪族炭化水素基と下記置換基との組み合わせのうち、所定の炭素原子数を満たすものが挙げられ、
R63及びR64で表される置換基を有している場合もある炭素原子数6~35の芳香環含有炭化水素基又は置換基を有している場合もある炭素原子数2~35の複素環含有基としては、上記X5で表される炭素原子数6~35の芳香環含有炭化水素基又は炭素原子数2~35の複素環含有基又はこれらの基と下記置換基とを組み合わせた基が挙げられる。
X5で表されるm価の有機基(例えば前記の脂肪族炭化水素基、芳香環含有炭化水素基、複素環含有基)及びR63及びR64で表される前記の脂肪族炭化水素基、芳香環含有炭化水素基、複素環含有基が置換されている場合の置換基としては、ビニル、アリル、アクリル、メタクリル等のエチレン性不飽和基;フッ素、塩素、臭素、ヨウ素等のハロゲン原子;アセチル、2-クロロアセチル、プロピオニル、オクタノイル、アクリロイル、メタクリロイル、フェニルカルボニル(ベンゾイル)、フタロイル、4-トリフルオロメチルベンゾイル、ピバロイル、サリチロイル、オキザロイル、ステアロイル、メトキシカルボニル、エトキシカルボニル、t-ブトキシカルボニル、n-オクタデシルオキシカルボニル、カルバモイル等のアシル基;アセチルオキシ、ベンゾイルオキシ等のアシルオキシ基;アミノ、エチルアミノ、ジメチルアミノ、ジエチルアミノ、ブチルアミノ、シクロペンチルアミノ、2-エチルヘキシルアミノ、ドデシルアミノ、アニリノ、クロロフェニルアミノ、トルイジノ、アニシジノ、N-メチル-アニリノ、ジフェニルアミノ,ナフチルアミノ、2-ピリジルアミノ、メトキシカルボニルアミノ、フェノキシカルボニルアミノ、アセチルアミノ、ベンゾイルアミノ、ホルミルアミノ、ピバロイルアミノ、ラウロイルアミノ、カルバモイルアミノ、N,N-ジメチルアミノカルボニルアミノ、N,N-ジエチルアミノカルボニルアミノ、モルホリノカルボニルアミノ、メトキシカルボニルアミノ、エトキシカルボニルアミノ、t-ブトキシカルボニルアミノ、n-オクタデシルオキシカルボニルアミノ、N-メチル-メトキシカルボニルアミノ、フェノキシカルボニルアミノ、スルファモイルアミノ、N,N-ジメチルアミノスルホニルアミノ、メチルスルホニルアミノ、ブチルスルホニルアミノ、フェニルスルホニルアミノ等の置換アミノ基;スルホンアミド基、スルホニル基、カルボキシル基、シアノ基、スルホ基、水酸基、ニトロ基、メルカプト基、イミド基、カルバモイル基、スルホンアミド基、ホスホン酸基、リン酸基又はカルボキシル基、スルホ基、ホスホン酸基、リン酸基の塩等が挙げられ、これらの基は更に置換されている場合もある。また、カルボキシル基及びスルホ基は塩を形成している場合もある。
mが2であるとき、X5は、下記一般式(1)のように表すこともできる。
該脂肪族炭化水素基は、-O-、-S-、-CO-、-COO-、-OCO-又は-NH-、或いは酸素原子が隣り合うことなしにこれらを組み合わせた結合基で中断されていてもよく、
Z1及びZ2は、それぞれ独立に、直接結合、-O-、-S-、>CO、-CO-O-、-O-CO-、-SO2-、-SS-、-SO-、>NR67、>PR67、置換基を有している場合もある炭素原子数1~20の二価の脂肪族炭化水素基又は炭素原子数6~10の二価の芳香族炭化水素基を表し、
R65、R66及びR67は、それぞれ独立に、水素原子、置換基を有している場合もある炭素原子数1~35の脂肪族炭化水素基、置換基を有している場合もある炭素原子数6~35の芳香環含有炭化水素基又は置換基を有している場合もある炭素原子数2~35の複素環含有基を表す。)
R72は炭素原子数1~10のアルキル基、炭素原子数1~10のアルコキシ基、炭素原子数2~10のアルケニル基又はハロゲン原子を表し、上記アルキル基、アルコキシ基及びアルケニル基は置換基を有していてもよく、
fは0~5の整数である。)
該アルキル基及びアリールアルキル基中のメチレン基は不飽和結合、-O-又は-S-で中断されていてもよく、
R73は、隣接するR73同士で環を形成している場合もあり、
pは0~4の数を表し、
qは0~8の数を表し、gは0~4の数を表し、
hは0~4の数を表し、
gとhの数の合計は2~4である。)
Z1、Z2及びZ3は、それぞれ独立に、直接結合、-O-、-S-、>CO、-CO-O-、-O-CO-、-SO2-、-SS-、-SO-、>NR68、>PR68、置換基を有している場合もある炭素原子数1~20の二価の脂肪族炭化水素基又は炭素原子数6~10の二価の芳香族炭化水素基を表し、
R68は、水素原子、置換基を有している場合もある炭素原子数1~35の脂肪族炭化水素基、置換基を有している場合もある炭素原子数6~35の芳香族炭化水素基又は置換基を有している場合もある炭素原子数2~35の複素環含有基を表し、
前記の各脂肪族炭化水素基は、炭素-炭素二重結合、-O-、-CO-、-O-CO-、-CO-O-又は-SO2-で中断されている場合もある。)
該脂肪族炭化水素基は、-COO-、-O-、-OCO-、-NHCO-、-NH-又は-CONH-で中断されていてもよく、Z1~Z4は、それぞれ独立に、上記一般式(2)におけるZ1~Z3で表される基と同じ範囲の基である。)
該脂肪族炭化水素基は、-COO-、-O-、-OCO-、-NHCO-、-NH-又は-CONH-で中断されていてもよく、
Z1~Z5は、それぞれ独立に、上記一般式(2)におけるZ1~Z3で表される基と同じ範囲の基である。)
該脂肪族炭化水素基は、-COO-、-O-、-OCO-、-NHCO-、-NH-又は-CONH-で中断されていてもよく、
Z1~Z6は、それぞれ独立に、上記一般式(2)におけるZ1~Z3で表される基と同じ範囲の基である。)
R65、R66及びR67で表される置換基を有している場合もある炭素原子数6~35の芳香環含有炭化水素基としては、上記一般式(III-A)におけるX5で表されるm価の有機基として例示した1価の芳香環含有炭化水素基及びこれらの基が上記一般式(III-A)におけるX5で表されるm価の有機基を表す基の置換基として例示したものにより置換された基等が挙げられ、これらの基又は上記一般式(III-A)におけるX5で表されるm価の有機基として例示した2価の芳香環含有炭化水素基がZ1及びZ2で置換された二価の基が、一般式(1)におけるY10で表される二価の炭素原子数6~35の芳香環含有炭化水素基として挙げられる。
R65、R66及びR67で表される置換基を有している場合もある炭素原子数2~35の複素環含有基としては、上記一般式(III-A)におけるX5で表されるm価の有機基として例示した1価の複素環含有基及びこれらの基が上記一般式(III-A)におけるX5で表されるm価の有機基を表す基の置換基として例示したものにより置換された基等が挙げられ、これらの基又は上記一般式(III-A)におけるX5で表されるm価の有機基として例示した2価の複素環含有基がZ1及びZ2で置換された二価の基が、一般式(1)におけるY10で表される二価の炭素原子数2~35の複素環含有基として挙げられる。
Z1、Z2で表される置換基を有している場合もある2価の炭素原子数1~20の脂肪族炭化水素基又は置換基を有している場合もある2価の炭素原子数6~10の芳香族炭化水素基としては、それぞれ、Y10で表される置換基を有している場合もある二価の脂肪族炭化水素基又は芳香環含有炭化水素基として上記で記載したもののうち所定の炭素原子数のものが挙げられる。
R72で表される炭素原子数1~10のアルキル基としては、R61で表される炭素原子数1~40のアルキル基として例示した基のうち、所定の炭素原子数を満たす基等が挙げられ、
R72で表される炭素原子数1~10のアルコキシ基としては、メチルオキシ、エチルオキシ、プロピルオキシ、イソプロピルオキシ、ブチルオキシ、第二ブチルオキシ、第三ブチルオキシ、イソブチルオキシ、アミルオキシ、イソアミルオキシ、第三アミルオキシ、ヘキシルオキシ、シクロヘキシルオキシ、ヘプチルオキシ、イソヘプチルオキシ、第三ヘプチルオキシ、n-オクチルオキシ、イソオクチルオキシ、第三オクチルオキシ、2-エチルヘキシルオキシ、ノニルオキシ、デシルオキシ等が挙げられ、
上記フェニル基、アルキル基、アルコキシ基及びアルケニル基の置換基は、上記一般式(III-A)におけるX5で表されるm価の有機基を表す基の置換基として例示したものと同様である。
R73及びR74で表される置換基を有している場合もある炭素原子数6~20のアリール基としては、R61で表される炭素原子数6~20のアリール基として例示した基等が挙げられ、
R73及びR74で表される置換基を有している場合もある炭素原子数6~20のアリールオキシ基としては、フェニルオキシ、ナフチルオキシ、2-メチルフェニルオキシ、3-メチルフェニルオキシ、4-メチルフェニルオキシ、4-ビニルフェニル二オキシ、3-iso-プロピルフェニルオキシ、4-iso-プロピルフェニルオキシ、4-ブチルフェニルオキシ、4-tert-ブチルフェニルオキシ、4-へキシルフェニルオキシ、4-シクロヘキシルフェニルオキシ、4-オクチルフェニルオキシ、4-(2-エチルヘキシル)フェニルオキシ、2,3-ジメチルフェニルオキシ、2,4-ジメチルフェニルオキシ、2,5-ジメチルフェニルオキシ、2.6-ジメチルフェニルオキシ、3.4-ジメチルフェニルオキシ、3.5-ジメチルフェニルオキシ、2,4-ジーtert-ブチルフェニルオキシ、2,5-ジーtert-ブチルフェニルオキシ、2,6-ジーtert-ブチルフェニルオキシ、2.4-ジーtert-ペンチルフェニルオキシ、2,5-tert-アミルフェニルオキシ、4-シクロへキシルフェニルオキシ、2,4,5-トリメチルフェニルオキシ、フェロセニルオキシ等の基が挙げられ、
R73及びR74で表される置換基を有している場合もある炭素原子数6~20のアリールチオ基としては、上記置換基を有している場合もある炭素原子数6~20のアリールオキシ基の酸素原子を硫黄原子に置換した基等が挙げられ、
R73及びR74で表される置換基を有している場合もある炭素原子数8~20のアリールアルケニル基としては、上記置換基を有している場合もある炭素原子数6~20のアリールオキシ基の酸素原子をビニル、アリル、1-プロペニル、イソプロペニル、2-ブテニル、1,3-ブタジエニル、2-ペンテニル、2-オクテニル等のアルケニル基で置換した基等が挙げられ、
R73及びR74で表される炭素原子数7~20のアリールアルキル基としては、R61で表される炭素原子数7~20のアリールアルキル基として例示した基等が挙げられ、
R73及びR74で表される置換基を有している場合もある炭素原子数2~20の複素環含有基としては、R61で表される炭素原子数2~20の複素環含有基として例示した基等が挙げられる。
上記一般式(2)におけるY11で表される三価の炭素原子数3~35の脂環族炭化水素基としては、シクロペンチル、シクロヘキシル、シクロヘプチル、シクロオクチル、シクロデカニル、1-アダマンチル、2-アダマンチル、ノルアダマンチル、2-メチルアダマンチル、ノルボルニル、イソノルボルニル、パーヒドロナフチル、パーヒドロアントラセニル、ビシクロ[1.1.0]ブチル、ビシクロ[1.1.1]ペンチル、ビシクロ[2.1.0]ペンチル、ビシクロ[3.1.0]ヘキシル、ビシクロ[2.1.1]ヘキシル、ビシクロ[2.2.0]ヘキシル、ビシクロ[4.1.0]ヘプチル、ビシクロ[3.2.0]ヘプチル、ビシクロ[3.1.1]ヘプチル、ビシクロ[2.2.1]ヘプチル、ビシクロ[5.1.0]オクチル、ビシクロ[4.2.0]オクチル、ビシクロ[4.1.1]オクチル、ビシクロ[3.3.0]オクチル、ビシクロ[3.2.1]オクチル、ビシクロ[2.2.2]オクチル、スピロ〔4,4〕ノナニル、スピロ〔4,5〕デカニル、デカリン、トリシクロデカニル、テトラシクロドデカニル、セドロール、シクロドデカニル等の基が、Z1、Z2及びZ3で置換された三価の基等が挙げられ、
Y11で表される三価の炭素原子数6~35の芳香環含有炭化水素基としては、上記一般式(III-A)におけるX5で表されるm価の有機基として例示した1価~3価の芳香環含有炭化水素基及びこれらの基が上記一般式(III-A)におけるX5で表されるm価の有機基を表す基の置換基として例示したものにより置換された基等が、Z1、Z2及びZ3で置換された三価の基等が挙げられ、
Y11で表される三価の炭素原子数2~35の複素環含有基としては、上記一般式(III-A)におけるX5で表されるm価の有機基として例示した1価~3価の複素環含有基及びこれらの基が上記一般式(III-A)におけるX5で表されるm価の有機基を表す基の置換基として例示したものにより置換された基等が、Z1、Z2及びZ3で置換された三価の基等が挙げられ、
また、一般式(2)におけるR68で表される置換基を有している場合もある炭素原子数1~35の脂肪族炭化水素基、置換基を有している場合もある炭素原子数6~35の芳香族炭化水素基及び置換基を有している場合もある炭素原子数2~35の複素環含有基としては、それぞれ、上記一般式(1)におけるR65及びR66の説明で例示した脂肪族炭化水素基、芳香環含有炭化水素基、複素環含有基が挙げられる。
また、一般式(2)におけるZ1~Z3で表される置換基を有している場合もある2価の炭素原子数1~20の脂肪族炭化水素基又は置換基を有している場合もある2価の炭素原子数6~10の芳香族炭化水素基としては、それぞれ、一般式(1)におけるZ1~Z2で表される置換基を有している場合もある二価の脂肪族炭化水素基又は芳香環含有炭化水素基と同様のものが挙げられる。
Y12で表される炭素原子数6~35の芳香環含有炭化水素基としては、上記一般式(III-A)におけるX5で表されるm価の有機基として例示した1価~3価の芳香環含有炭化水素基及びこれらの基が上記一般式(III-A)におけるXで表されるm価の有機基を表す基の置換基として例示したものにより置換された基等がZ1、Z2、Z3及びZ4で置換された四価の基等が挙げられ、
Y12で表される四価の炭素原子数2~35の複素環含有基としては、上記一般式(III-A)におけるX5で表されるm価の有機基として例示した1価~3価の複素環含有基及びこれらの基が上記一般式(III-A)におけるX5で表されるm価の有機基を表す基の置換基として例示したものにより置換された基等がZ1、Z2、Z3及びZ4で置換された四価の基等が挙げられる。
Y13で表される五価の炭素原子数6~35の芳香環含有炭化水素基としては、上記一般式(III-A)におけるX5で表されるm価の有機基として例示した1価~3価の芳香環含有炭化水素基及びこれらの基が上記一般式(I-A)におけるX5で表されるm価の有機基を表す基の置換基として例示したものにより置換された基等がZ1、Z2、Z3、Z4及びZ5で置換された五価の基等が挙げられ、
Y13で表される五価の炭素原子数2~35の複素環含有基としては、上記一般式(III-A)におけるX5で表されるm価の有機基として例示した1価~3価の複素環含有基及びこれらの基が上記一般式(III-A)におけるX5で表されるm価の有機基を表す基の置換基として例示したものにより置換された基等がZ1、Z2、Z3、Z4及びZ5で置換された五価の基等が挙げられる。
Y14で表される六価の炭素原子数6~35の芳香環含有炭化水素基としては、上記一般式(III-A)におけるX5で表されるm価の有機基として例示した1価~3価の芳香環含有炭化水素基及びこれらの基が上記一般式(III-A)におけるX5で表されるm価の有機基を表す基の置換基として例示したものにより置換された基等がZ1、Z2、Z3、Z4、Z5及びZ6で置換された六価の基等が挙げられ、
Y14で表される六価の炭素原子数2~35の複素環含有基としては、上記一般式(III-A)におけるX5で表されるm価の有機基として例示した1価~3価の複素環含有基及びこれらの基が上記一般式(I-A)におけるX5で表されるm価の有機基を表す基の置換基として例示したものにより置換された基等がZ1、Z2、Z3、Z4、Z5及びZ6で置換された六価の基等が挙げられる。
R81、R82、R83、R84及びR85で表されるハロゲン原子、置換基を有している場合もある炭素原子数1~40のアルキル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基、炭素原子数2~20の複素環含有基としては、上記一般式(III)におけるR61又はR62の説明で例示したものが挙げられ、
上記一般式(V)におけるR86、R87、R88及びR89で表されるハロゲン原子、置換基を有している場合もある炭素原子数1~40のアルキル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基、炭素原子数2~20の複素環含有基としては、上記一般式(III)におけるR61又はR62の説明で例示したものが挙げられ、
上記一般式(VI)におけるR91、R92、R93及びR94で表されるハロゲン原子、置換基を有している場合もある炭素原子数1~40のアルキル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基、炭素原子数2~20の複素環含有基としては、上記一般式(III)におけるR61又はR62の説明で例示したものが挙げられる。
R81、R82、R83、R84及びR85のうち、水素原子以外の基としては、炭素原子数1~20のアルキル基、炭素原子数6~10のアリール基、炭素原子数7~12のアリールアルキル基、炭素原子数2~10の複素環含有基、特にR81~R85の何れか1つが炭素原子数1~4のアルキル基又は炭素原子数2~10の複素環含有基であるものが好ましく、
R62は、-CO-O-を介して、下記の置換基を有するものが好ましい。
・炭素原子数1~8のアルキル基(特に、メチル、エチル、プロピル、iso-プロピル、ブチル、sec-ブチル、tert-ブチル、iso-ブチル、アミル、1-メチルブチル、2-メチルブチル、3-メチルブチル、1-エチルプロピル、1,1-ジメチルプロピル、1,2-ジメチルプロピル、2,2-ジメチルプロピル)
・炭素原子数7~10のアリールアルキル基(特にベンジル基)
・炭素原子数2~6のアルケニル基(特にプロペン-1-イル基)
環A2が、ベンゼン、ナフタレンであるものが好ましく、
R86、R87、R88及びR89のうち、水素原子以外の基としては、炭素原子数1~20のアルキル基、炭素原子数6~10のアリール基、炭素原子数7~12のアリールアルキル基、2~10の複素環含有基、特に炭素原子数1~8のアルキル基、炭素原子数2~10の複素環含有基であるものが好ましく、
R62は、-CO-O-を介して、下記の置換基を有する者が好ましい。
・炭素原子数1~8のアルキル基(特に、メチル、エチル、プロピル、iso-プロピル、ブチル、sec-ブチル、tert-ブチル、iso-ブチル、アミル、1-メチルブチル、2-メチルブチル、3-メチルブチル、1-エチルプロピル、1,1-ジメチルプロピル、1,2-ジメチルプロピル、2,2-ジメチルプロピル)
・炭素原子数7~10のアリールアルキル基(特にベンジル基)
・炭素原子数2~6のアルケニル基(特にプロペン-1-イル基)
X11を表す上記一般式(1)において、Y10が、硫黄原子、炭素原子数6~25の芳香環含有炭化水素基、炭素原子数2~21の複素環含有基であるものが好ましく、
Z1及びZ2が直接結合、-CO-O-、-O-CO-又は置換基を有している場合もあり-COO-、-O-、-OCO-、-NHCO-、-NH-又は-CONH-(以下「-COO-等」と省略する)で中断されている場合もある炭素原子数1~20の脂肪族炭化水素基若しくは炭素原子数6~10の芳香族炭化水素基、特に置換基を有している場合もあり-COO-等で中断されている場合もある炭素原子数1~8の脂肪族炭化水素基であるものが好ましい。
R91、R92、R93及びR94のうち、水素原子以外の基としては、炭素原子数1~20のアルキル基、炭素原子数6~10のアリール基、炭素原子数7~12のアリールアルキル基、炭素原子数2~10の複素環含有基、特にR91~R94の何れか1つが炭素原子数1~4のアルキル基又は炭素原子数2~10の複素環含有基であるものが好ましい。
R62は、-CO-O-を介して、下記の置換基を有する者が好ましい。
・炭素原子数1~8のアルキル基(特に、メチル、エチル、プロピル、iso-プロピル、ブチル、sec-ブチル、tert-ブチル、iso-ブチル、アミル、1-メチルブチル、2-メチルブチル、3-メチルブチル、1-エチルプロピル、1,1-ジメチルプロピル、1,2-ジメチルプロピル、2,2-ジメチルプロピル)
・炭素原子数1~10のアリールアルキル基(特にベンジル基)
・炭素原子数2~6のアルケニル基(特にプロペン-1-イル基)
X3が上記一般式(1)で表される基である場合、一般式(1)中のY10が、硫黄原子、2価の炭素原子数1~20のアルキル基、炭素原子数6~25の芳香環含有炭化水素基、炭素原子数2~21の複素環含有基もしくは2,4,8,10-テトラオキサスピロ[5,5]ウンデカンであるもの、特に2価の炭素原子数1~15のアルキル基、炭素原子数6~15の芳香環含有炭化水素基もしくは2,4,8,10-テトラオキサスピロ[5,5]ウンデカンであるものが好ましく、
Z1及びZ2が直接結合、-CO-O-、-O-CO-、又は置換基を有している場合もあり-COO-等で中断されている場合もある炭素原子数1~20の脂肪族炭化水素基、炭素原子数6~10の芳香族炭化水素基、特に置換基を有している場合もあり-COO-等で中断されている場合もある炭素原子数1~8の脂肪族炭化水素基であるものが好ましい。
X3が上記一般式(2)で表される基である場合、Y11が、3価の炭素原子数1~20のアルキル基、炭素原子数6~10のアリール基、炭素原子数7~12のアリールアルキル基若しくは炭素原子数1~10の複素環含有基であるもの、特に3価の炭素原子数1~8のアルキル基、炭素原子数6~9のアリール基若しくは炭素原子数2~6の複素環含有基であるものが好ましく、
Z1、Z2及びZ3は、Z1及びZ2と同様のものが好ましく、
X3が上記一般式(3)となる場合、Y12は、4価である以外はY11と同様であるものが好ましく、
Z1~Z4は、Z1及びZ2と同様であるものが好ましく、
X3が上記一般式(4)となる場合、Y13は、5価である以外はY11と同様であるものが好ましく、
Z1~Z5はZ1及びZ2と同様であるものが好ましく、
X3が上記一般式(5)となる場合、Y14は、6価である以外はY11と同様であるものが好ましく、
Z1~Z6は、Z1及びZ2と同様であるものが好ましい。
本発明の組成物に用いられる重合開始剤(B)は、上記一般式(I)で表されるオキシムエステル化合物の一種以上を含む。
即ち、本明細書において、上記一般式(I)で表わされる化合物及びその例示化合物は、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。
、R31、R32、R33、R34及びR35は、それぞれ独立に、R11、OR11、SR11、COR11、CONR15R16、NR12COR11、OCOR11、COOR14、SCOR11、OCSR11、COSR14、CSOR11、水酸基、ニトロ基、CN又はハロゲン原子を表し、R31とR32、R32とR33、R33とR34及びR34とR35はそれぞれ一緒になって環を形成している場合もある。)
R103及びR104は、それぞれ独立に、ハロゲン原子、ニトロ基、シアノ基、水酸基、カルボキシル基、R105、OR106、SR107、NR108R109、COR110、SOR111、SO2R112又はCONR113R114を表し、R103及びR104は、互いに結合して環を形成していてもよく、R103同士、R104同士が互いに結合して環を形成していてもよく、
X11は、酸素原子、硫黄原子、セレン原子、CR115R116、CO、NR117又はPR118を表し、
X12は、単結合又はCOを表し、
R105、R106、R107、R108、R109、R110、R111、R112、R113、R114、R115、R116、R117及びR118は、それぞれ独立に、炭素原子数1~20のアルキル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基又は炭素原子数2~20の複素環含有基を表し、
R101、R102、R105、R106、R107、R108、R109、R110、R111、R112、R113、R114、R115、R116、R117及びR118中の炭素原子数1~20のアルキル基は、直鎖状でも分岐上でも環状でも直鎖と環の組み合わせでも分岐と環の組み合わせでもよく、
R101、R102、R105、R106、R107、R108、R109、R110、R111、R112、R113、R114、R115、R116、R117及びR118中の炭素原子数1~20のアルキル基又は炭素原子数7~20のアリールアルキル基中のメチレン基は、ハロゲン原子、ニトロ基、シアノ基、水酸基、カルボキシル基又は環含有基で置換されていてもよく、-O-で中断されていてもよく、
aは、0~4の整数を表し、
bは、0~5の整数を表す。)
また、上記不飽和一塩基酸を作用させた後に作用させる上記多塩基酸無水物としては、ビフェニルテトラカルボン酸二無水物、テトラヒドロ無水フタル酸、無水コハク酸、無水マレイン酸、トリメリット酸無水物、ピロメリット酸無水物、2,2'-3,3'-ベンゾフェノンテトラカルボン酸無水物、エチレングリコールビスアンヒドロトリメリテート、グリセロールトリスアンヒドロトリメリテート、ヘキサヒドロ無水フタル酸、メチルテトラヒドロ無水フタル酸、ナジック酸無水物、メチルナジック酸無水物、トリアルキルテトラヒドロ無水フタル酸、ヘキサヒドロ無水フタル酸、5-(2,5-ジオキソテトラヒドロフリル)-3-メチル-3-シクロヘキセン-1,2-ジカルボン酸無水物、トリアルキルテトラヒドロ無水フタル酸-無水マレイン酸付加物、ドデセニル無水コハク酸、無水メチルハイミック酸等が挙げられる。
上記エポキシ化合物、上記不飽和一塩基酸及び上記多塩基酸無水物の反応は、常法に従って行なうことができる。
その他、フェノールノボラック型エポキシ化合物、ビフェニルノボラック型エポキシ化合物、クレゾールノボラック型エポキシ化合物、ビスフェノールAノボラック型エポキシ化合物、ジシクロペンタジエンノボラック型エポキシ化合物等のノボラック型エポキシ化合物;3,4-エポキシ-6-メチルシクロヘキシルメチル-3,4-エポキシ-6-メチルシクロヘキサンカルボキシレート、3,4-エポキシシクロヘキシルメチル-3,4-エポキシシクロヘキサンカルボキシレート、1-エポキシエチル-3,4-エポキシシクロヘキサン等の脂環式エポキシ化合物;フタル酸ジグリシジルエステル、テトラヒドロフタル酸ジグリシジルエステル、ダイマー酸グリシジルエステル等のグリシジルエステル類;テトラグリシジルジアミノジフェニルメタン、トリグリシジル-p-アミノフェノール、N,N-ジグリシジルアニリン等のグリシジルアミン類;1,3-ジグリシジル-5,5-ジメチルヒダントイン、トリグリシジルイソシアヌレート等の複素環式エポキシ化合物;ジシクロペンタジエンジオキシド等のジオキシド化合物;ナフタレン型エポキシ化合物、トリフェニルメタン型エポキシ化合物、ジシクロペンタジエン型エポキシ化合物等を用いることもできる。
これらの中でも、ガラスフリット、酸化チタン、シリカ、層状粘土鉱物、銀等が好ましい。本発明の感光性組成物において、上記無機化合物の含有量は、上記樹脂100質量部に対して、好ましくは0.1~1000質量部、より好ましくは10~800質量部である。尚、これらの無機化合物は1種又は2種以上を使用することができる。
他の有機重合体を使用する場合、その使用量は、上記樹脂100質量部に対して、好ましくは10~500質量部である。
すなわち、(1)本発明の組成物の塗膜を基板上に形成する工程、(2)該塗膜に所定のパターン形状を有するマスクを介して放射線を照射する工程、(3)露光後のベーク工程、(4)露光後の該被膜を現像する工程、(5)現像後の該被膜を加熱する工程により好ましく形成される。
上記マスクとしては、ハーフトーンマスク又はグレースケールマスク等の多階調マスクを用いることもできる。
本発明の組成物の具体的な用途としては、光学フィルタ、塗料、コーティング剤、ライニング剤、接着剤、印刷版、絶縁ワニス、絶縁シート、積層板、プリント基盤、半導体装置用・LEDパッケージ用・液晶注入口用・有機EL用・光素子用・電気絶縁用・電子部品用・分離膜用等の封止剤、成形材料、パテ、ガラス繊維含浸剤、目止め剤、半導体用・太陽電池用等のパッシベーション膜、薄膜トランジスタ(TFT)・液晶表示装置・有機EL表示装置・プリント基板等に用いられる層間絶縁膜、表面保護膜、プリント基板、或いはカラーテレビ、PCモニタ、携帯情報端末、CCDイメージセンサのカラーフィルタ、プラズマ表示パネル用の電極材料、印刷インク、歯科用組成物、光造形用樹脂、液状及び乾燥膜の双方、微小機械部品、ガラス繊維ケーブルコーティング、ホログラフィ記録用材料、磁気記録材料、光スイッチ、めっき用マスク、エッチングマスク、スクリーン印刷用ステンシル、透明導電膜等のタッチパネル、MEMS素子、ナノインプリント材料、半導体パッケージの二次元及び三次元高密度実装等のフォトファブリケーション、加飾シート、人口爪、ガラス代替光学フィルム、電子ペーパー、光ディスク、プロジェクター・光通信用レーザー等に用いられるマイクロレンズアレイ、液晶表示装置のバックライトに使用されるプリズムレンズシート、プロジェクションテレビ等のスクリーンに使用されるフレネルレンズシート、レンチキュラーレンズシート等のレンズシートのレンズ部、またはこのようなシートを用いたバックライト等、マイクロレンズ・撮像用レンズ等の光学レンズ、光学素子、光コネクター、光導波路、絶縁用パッキング、熱収縮ゴムチューブ、O-リング、表示デバイス用シール剤、保護材、光ファイバー保護材、粘着剤、ダイボンディング剤、高放熱性材料、高耐熱シール材、太陽電池・燃料電池・二次電池用部材、電池用固体電解質、絶縁被覆材、複写機用感光ドラム、ガス分離膜、コンクリート保護材・ライニング・土壌注入剤・シーリング剤・蓄冷熱材・ガラスコーティング・発泡体等の土木・建築材料、チューブ・シール材・コーティング材料・滅菌処理装置用シール材・コンタクトレンズ・酸素富化膜、バイオチップ等の医療用材料、自動車部品、各種機械部品等の各種の用途に使用することができ、その用途に特に制限はない。
[表1]~[表3]の配合に従い組成物を調製した。これをガラス基板上にスピンコート(900rpm、10秒間)し、ホットプレートを用いて、90℃で、90秒間プリベークを行い、光源として高圧水銀ランプを用いて露光した(20mJ/cm2~200mJ/cm2まで20mJ/cm2ごとに10分割)。現像液として2.5質量%炭酸ナトリウム水溶液を用い、スピン現像機で40秒間現像後、よく水洗し、オーブンを用いて、230℃で、30分ポストベークを行い、パターンを定着させた。
[表3A]~[表3C]の配合に従い着色組成物を調製して、着色重合性組成物(実施例2-1~2-3及び比較例2-1~2-15)を得た。
B’-2 N-1717(アクリジン系化合物:ADEKA社製)
B’-3 Lucirin TPO(BASF社製)
B’-4 ベンゾフェノン
B’-5 OXE-01(BASF製)
C-2 カヤラッドDPHA(多官能アクリレート;日本化薬社製)
C-3 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
C-4 ブルー顔料分散液(着色剤としてC.I.ピグメントブルー15:6を15質量部、分散剤としてBYK161(ビックケミー(BYK)社製)12.5質量部(固形分濃度40質量%)、溶媒としてプロピレングリコールモノメチルエーテルアセテート72.5質量部を用いて、ビーズミルにより処理することにより調製した。)
C-5 SPC-3000(昭和電工社製、固形分42.7質量%のPGMEA溶液)
C-6 レッド顔料分散液(着色剤としてC.I.ピグメントレッド254を15質量部、分散剤としてアジスパーPB821(味の素ファインテクノ製)8.0質量部、溶媒としてPGMEA77.0質量部を用いて、ビーズミルにより処理することにより調製した。)
C-7 グリーン顔料分散液(着色剤としてC.I.ピグメントグリーン58を15質量部、分散剤としてBYK-LPN6919(ビックケミージャパン製)7.0質量部(固形分40質量%)、溶媒としてPGMEA78.0質量部を用いて、ビーズミルにより処理することにより調製した。)
上記実施例1-1~1-9及び比較例1-1~1-10で得られたパターンの高さを、触針式表面形状測定器(キーエンス製)を用いて測定し、下記式から残膜率(%)を求めて放射線感度とした。尚、残膜率が70%以上になる露光量が20mJ/cm2の時はA、20mJ/cm2超100mJ/cm2以下の時はB、100mJ/cm2超200mJ/cm2以下の時はC、200mJ/cm2の時に残膜率が70%以上にならなかった場合はDとした。試験結果を〔表4〕に示す。尚、下記式において初期膜厚はプリベーク後、ポストベーク前の膜厚である。
残膜率(%)=(ポストベーク後のパターンの高さ/初期膜厚)×100
[表1]~[表3]における実施例1-1~1-9及び比較例1-1~1-10の配合に従い調整した組成物を用い、別途、塗膜を得、この塗膜をマスクを介さずに全面硬化させた。硬化後の塗膜を、230℃×120分の条件で焼成し、焼成後の塗膜の400nmにおける透過率を測定した。透過率が95%以上のときをa、90~94%をb、89%以下のときをcとした。結果を上記[表4]に示す。
上記実施例2-1~2-3及び比較例2-1~2-15で得られた着色組成物について下記の方法によって感度の評価を行った。結果を下記[表4A]に示す。
ガラス基板上にスピンコーターにて、実施例2-1及び比較例2-1~2-5で得られた赤色着色組成物をC光源においてx=0.670、y=0.330になるような膜厚に塗布し着色被膜を形成した。該被膜に開口30μmのフォトマスクを介して、露光ギャップ100μmで20、40,60,80mJ/cm2の露光量で露光した。現像時間は、23℃の0.04質量%水酸化カリウム水溶液からなる現像液を現像圧1kgf/cm2(ノズル径1mm)で吐出することにより、未露光部が完全に溶解されるまでの時間(BT:ブレイクタイム)を基準として、BTの1.5倍とした。その後、この基板を超純水で洗浄、風乾後、この基板を230℃で20分間加熱して、基板上に赤色着色パターンを形成した。また実施例2-2及び比較例2-6~2-10で得られた緑色着色組成物を用い、C光源においてx=0.240、y=0.580になるような膜厚に塗布した以外は上記と同様にして緑色着色パターンを得た。また実施例2-3及び比較例2-11~2-15で得られた青色着色組成物を用いC光源においてx=0.135、y=0.098になる膜厚に塗布した以外は上記と同様にして青色着色パターンを得た。これら形成したパターンのフォトマスク開口30μmのパターン幅を測定した。
A(◎):露光量が20mJ/cm2のときに線幅が30μm以上になった。
B(○):露光量が20mJ/cm2のときには線幅が30μm以上にならなかったが、露光量が40mJ/cm2のときに線幅が30μm以上になった。
C(△):露光量が20mJ/cm2及び40mJ/cm2のときに線幅が30μm以上にならなかったが、露光量が60mJ/cm2のときに線幅が30μm以上になった。
D(×):露光量が20mJ/cm2、40mJ/cm2及び60mJ/cm2のときに線幅が30μm以上にならなかったが、露光量が80mJ/cm2のときに線幅が30μm以上になったか、或いは80mJ/cm2のときに線幅が30μm以上にならなかった。
Claims (3)
- 潜在性酸化防止剤(A)、及び下記一般式(I)で表されるオキシムエステル化合物の一種以上を含む重合開始剤(B)を含有する組成物。
R11、R12及びR13は、それぞれ独立に、水素原子、炭素原子数1~20のアルキル基、炭素原子数6~30のアリール基、炭素原子数7~30のアリールアルキル基又は炭素原子数2~20の複素環含有基を表し、
R11、R12及びR13で表わされる基の水素原子は、更にR21、OR21、COR21、SR21、NR22R23、CONR22R23、NR22OR23、NCOR22OCOR23、NR22COR21、OCOR21、COOR21、SCOR21、OCSR21、COSR21、CSOR21、水酸基、ニトロ基、CN、ハロゲン原子、又はCOOR21で置換されている場合もあり、
R21、R22及びR23は、それぞれ独立に、水素原子、炭素原子数1~20のアルキル基、炭素原子数6~30のアリール基、炭素原子数7~30のアリールアルキル基又は炭素原子数2~20の複素環含有基を表し、
R21、R22及びR23で表される基の水素原子は、更に水酸基、ニトロ基、CN、ハロゲン原子、水酸基又はカルボキシル基で置換されている場合もあり、
R11、R12、R13、R21、R22及びR23で表される基のアルキレン部分のメチレン基は、-O-、-S-、-COO-、-OCO-、-OCOO-、-CONR24-、-NR24-、-NR24CO-、-NR24COO-、-OCONR24-、-SCO-、-COS-、-OCS-又は-SCOO-により置き換えられている場合もあり、
R24は、水素原子、炭素原子数1~20のアルキル基、炭素原子数6~30のアリール基、炭素原子数7~30のアリールアルキル基又は炭素原子数2~20の複素環含有基を表し、
R11、R12、R13、R21、R22、R23及びR24で表される基のアルキル部分は、分岐側鎖がある場合もあり、環状アルキルである場合もあり、
R3は、水素原子、炭素原子数1~20のアルキル基、炭素原子数6~30のアリール基、炭素原子数7~30のアリールアルキル基又は炭素原子数2~20の複素環含有基を表し、R3で表される基のアルキル部分は、分岐側鎖がある場合もあり、環状アルキルである場合もあり、また、R3とR7、R3とR8、R4とR5、R5とR6及びR6とR7はそれぞれ一緒になって環を形成している場合もあり、
R3で表わされる基の水素原子は、更にR21、OR21、COR21、SR21、NR22R23、CONR22R23、NR22OR23、NCOR22OCOR23、NR22COR21、OCOR21、COOR21、SCOR21、OCSR21、COSR21、CSOR21、水酸基、ニトロ基、CN、ハロゲン原子、又はCOOR21で置換されている場合もあり、
R4、R5、R6及びR7は、それぞれ独立に、R11、OR11、SR11、COR14、CONR15R16、NR12COR11、OCOR11、COOR14、SCOR11、OCSR11、COSR14、CSOR11、水酸基、CN又はハロゲン原子を表し、R4とR5、R5とR6及びR6とR7はそれぞれ一緒になって環を形成している場合もあり、
R4、R5、R6及びR7で表わされる基の水素原子は、更にR21、OR21、COR21、SR21、NR22R23、CONR22R23、NR22OR23、NCOR22OCOR23、NR22COR21、OCOR21、COOR21、SCOR21、OCSR21、COSR21、CSOR21、水酸基、ニトロ基、CN、ハロゲン原子又はCOOR21で置換されている場合もあり、
R14、R15及びR16は、水素原子又は炭素原子数1~20のアルキル基を表し、
R14、R15及びR16で表される基のアルキル部分は、分岐側鎖がある場合もあり、環状アルキルである場合もあり、
R8は、R11、OR11、SR11、COR11、CONR12R13、NR12COR11、OCOR11、COOR11、SCOR11、OCSR11、COSR11、CSOR11、水酸基、CN又はハロゲン原子を表し、
nは、0又は1を表す。) - 潜在性酸化防止剤(A)が、下記一般式(III)で表される骨格を有することを特徴とする請求項1記載の組成物。
R61は、それぞれ独立に、水素原子、ハロゲン原子、シアノ基、水酸基、ニトロ基、カルボキシル基、置換基を有している場合もある炭素原子数1~40のアルキル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基又は炭素原子数2~20の複素環含有基を表し、
R62は、それぞれ独立に、炭素原子数1~20のアルキル基、炭素原子数2~20のアルケニル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基、炭素原子数2~20の複素環含有基又はトリアルキルシリル基を表し、
R61及びR62で表されるアルキル基又はアリールアルキル基中のメチレン基は、炭素-炭素二重結合、-O-、-S-、-CO-、-O-CO-、-CO-O-、-O-CO-O-、-O-CO-O-、-S-CO-、-CO-S-、-S-CO-O-、-O-CO-S-、-CO-NH-、-NH-CO-、-NH-CO-O-、-NR'-、-S-S-又は-SO2-から選ばれた基を酸素原子が隣り合わない条件で組み合わせた基で置き換えていてもよく、R’は、水素原子又は炭素原子数1~8のアルキル基を表し、
複数のR61同士は結合してベンゼン環又はナフタレン環を形成していてもよく、
dは、1~4の整数を表し、
kは、1~4の整数を表すが、dとkの合計は、環A1が取り得る置換基の数以下である。) - 潜在性酸化防止剤(A)が、下記一般式(III-A)で表される化合物からなることを特徴とする請求項1又は2記載の組成物。
R61は、それぞれ独立に、水素原子、ハロゲン原子、シアノ基、水酸基、ニトロ基、カルボキシル基、置換基を有している場合もある炭素原子数1~40のアルキル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基又は炭素原子数2~20の複素環含有基を表し、
R62は、それぞれ独立に、炭素原子数1~20のアルキル基、炭素原子数2~20のアルケニル基、炭素原子数6~20のアリール基、炭素原子数7~20のアリールアルキル基、炭素原子数2~20の複素環含有基又はトリアルキルシリル基を表し、
R61及びR62で表されるアルキル基又はアリールアルキル基中のメチレン基は、炭素-炭素二重結合、-O-、-S-、-CO-、-O-CO-、-CO-O-、-O-CO-O-、-O-CO-O-、-S-CO-、-CO-S-、-S-CO-O-、-O-CO-S-、-CO-NH-、-NH-CO-、-NH-CO-O-、-NR’-、-S-S-又は-SO2-から選ばれた基を酸素原子が隣り合わない条件で組み合わせた基で置き換えていてもよく、R’は、水素原子又は炭素原子数1~8のアルキル基を表し、
複数のR61同士は結合してベンゼン環又はナフタレン環を形成していてもよく、
mは、1~10の整数を表し、
dは、1~4の整数を表し、
kは、1~4の整数を表すが、dとkの合計は、環A1が取り得る置換基の数以下であり、
X5は、直接結合又はm価の原子、無機基若しくは有機基を表す。)
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Cited By (14)
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WO2019054281A1 (ja) | 2017-09-15 | 2019-03-21 | 富士フイルム株式会社 | 組成物、膜、積層体、赤外線透過フィルタ、固体撮像素子および赤外線センサ |
WO2020059509A1 (ja) | 2018-09-20 | 2020-03-26 | 富士フイルム株式会社 | 硬化性組成物、硬化膜、赤外線透過フィルタ、積層体、固体撮像素子、センサ、及び、パターン形成方法 |
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CN109188866A (zh) * | 2018-08-16 | 2019-01-11 | 韩国高智株式会社 | 一种用于抗反射有机硬掩模的组合物 |
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WO2019054281A1 (ja) | 2017-09-15 | 2019-03-21 | 富士フイルム株式会社 | 組成物、膜、積層体、赤外線透過フィルタ、固体撮像素子および赤外線センサ |
WO2020059509A1 (ja) | 2018-09-20 | 2020-03-26 | 富士フイルム株式会社 | 硬化性組成物、硬化膜、赤外線透過フィルタ、積層体、固体撮像素子、センサ、及び、パターン形成方法 |
WO2021100768A1 (ja) | 2019-11-21 | 2021-05-27 | 富士フイルム株式会社 | パターン形成方法、光硬化性樹脂組成物、積層体の製造方法、及び、電子デバイスの製造方法 |
WO2021193543A1 (ja) * | 2020-03-24 | 2021-09-30 | 株式会社Adeka | 化合物、組成物、硬化物及び硬化物の製造方法 |
WO2022004683A1 (ja) * | 2020-07-02 | 2022-01-06 | 富士フイルム株式会社 | 着色組成物、膜、カラーフィルタ、固体撮像素子および画像表示装置 |
WO2022131191A1 (ja) | 2020-12-16 | 2022-06-23 | 富士フイルム株式会社 | 組成物、膜、光学フィルタ、固体撮像素子、画像表示装置および赤外線センサ |
WO2022130773A1 (ja) | 2020-12-17 | 2022-06-23 | 富士フイルム株式会社 | 組成物、膜、光学フィルタ、固体撮像素子、画像表示装置および赤外線センサ |
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WO2023032545A1 (ja) | 2021-08-31 | 2023-03-09 | 富士フイルム株式会社 | 硬化物の製造方法、積層体の製造方法、及び、半導体デバイスの製造方法、並びに、処理液 |
WO2023037995A1 (ja) * | 2021-09-08 | 2023-03-16 | 住友化学株式会社 | 着色硬化性組成物 |
WO2023037996A1 (ja) * | 2021-09-08 | 2023-03-16 | 住友化学株式会社 | 着色硬化性組成物 |
WO2024004425A1 (ja) * | 2022-06-27 | 2024-01-04 | 富士フイルム株式会社 | 硬化性組成物、硬化物の製造方法、膜、光学素子、イメージセンサ、固体撮像素子、画像表示装置、及び、ラジカル重合開始剤 |
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JP6730287B2 (ja) | 2020-07-29 |
KR20180041622A (ko) | 2018-04-24 |
CN107636024A (zh) | 2018-01-26 |
EP3339331A4 (en) | 2019-05-01 |
JPWO2017030005A1 (ja) | 2018-05-31 |
KR102555632B1 (ko) | 2023-07-14 |
TWI724015B (zh) | 2021-04-11 |
CN107636024B (zh) | 2020-06-19 |
EP3339331A1 (en) | 2018-06-27 |
TW201716483A (zh) | 2017-05-16 |
EP3339331B1 (en) | 2022-02-16 |
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