WO2017170465A1 - Composition photosensible - Google Patents
Composition photosensible Download PDFInfo
- Publication number
- WO2017170465A1 WO2017170465A1 PCT/JP2017/012505 JP2017012505W WO2017170465A1 WO 2017170465 A1 WO2017170465 A1 WO 2017170465A1 JP 2017012505 W JP2017012505 W JP 2017012505W WO 2017170465 A1 WO2017170465 A1 WO 2017170465A1
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- WIPO (PCT)
- Prior art keywords
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- carbon atoms
- represented
- groups
- general formula
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- 239000000203 mixture Substances 0.000 title claims abstract description 80
- 229920000642 polymer Polymers 0.000 claims abstract description 37
- 239000000654 additive Substances 0.000 claims abstract description 20
- 230000000996 additive effect Effects 0.000 claims abstract description 17
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000000178 monomer Substances 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims description 8
- 230000001678 irradiating effect Effects 0.000 claims description 5
- 239000003505 polymerization initiator Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 abstract description 20
- 239000007870 radical polymerization initiator Substances 0.000 abstract description 5
- 230000005855 radiation Effects 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 description 284
- -1 tert-amyl Chemical group 0.000 description 210
- 125000001424 substituent group Chemical group 0.000 description 126
- 125000000623 heterocyclic group Chemical group 0.000 description 80
- 125000000217 alkyl group Chemical group 0.000 description 70
- 125000003118 aryl group Chemical group 0.000 description 70
- 125000001931 aliphatic group Chemical group 0.000 description 56
- 150000001875 compounds Chemical class 0.000 description 45
- 125000003710 aryl alkyl group Chemical group 0.000 description 36
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 32
- 150000002430 hydrocarbons Chemical group 0.000 description 31
- 125000000962 organic group Chemical group 0.000 description 30
- 229910052799 carbon Inorganic materials 0.000 description 26
- 125000005843 halogen group Chemical group 0.000 description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 22
- 239000010408 film Substances 0.000 description 21
- 150000001721 carbon Chemical group 0.000 description 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 16
- 239000000463 material Substances 0.000 description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 14
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 13
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 229920005989 resin Polymers 0.000 description 12
- 239000011347 resin Substances 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 125000003342 alkenyl group Chemical group 0.000 description 11
- 239000000049 pigment Substances 0.000 description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 10
- 125000004093 cyano group Chemical group *C#N 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
- 125000002947 alkylene group Chemical group 0.000 description 9
- 125000004430 oxygen atom Chemical group O* 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- 238000000576 coating method Methods 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 239000003086 colorant Substances 0.000 description 7
- 239000003822 epoxy resin Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 229920000647 polyepoxide Polymers 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- 125000004434 sulfur atom Chemical group 0.000 description 7
- 239000004593 Epoxy Substances 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 239000006229 carbon black Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 239000003999 initiator Substances 0.000 description 6
- 150000003839 salts Chemical class 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
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 229920000877 Melamine resin Polymers 0.000 description 5
- 125000002723 alicyclic group Chemical group 0.000 description 5
- 239000003963 antioxidant agent Substances 0.000 description 5
- 125000004104 aryloxy group Chemical group 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 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 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 125000003700 epoxy group Chemical group 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000005647 linker group Chemical group 0.000 description 5
- 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 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 5
- 229920002120 photoresistant polymer Polymers 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- 101001053395 Arabidopsis thaliana Acid beta-fructofuranosidase 4, vacuolar Proteins 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 4
- 239000006087 Silane Coupling Agent Substances 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 239000002585 base Substances 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
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 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 4
- 150000002484 inorganic compounds Chemical class 0.000 description 4
- 229910010272 inorganic material Inorganic materials 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 229920003986 novolac Polymers 0.000 description 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 125000000565 sulfonamide group Chemical group 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- BGCSUUSPRCDKBQ-UHFFFAOYSA-N 2,4,8,10-tetraoxaspiro[5.5]undecane Chemical compound C1OCOCC21COCOC2 BGCSUUSPRCDKBQ-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 101001053401 Arabidopsis thaliana Acid beta-fructofuranosidase 3, vacuolar Proteins 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 125000005110 aryl thio group Chemical group 0.000 description 3
- 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 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 3
- 239000003759 ester based solvent Substances 0.000 description 3
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000001041 indolyl group Chemical group 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 229940049920 malate Drugs 0.000 description 3
- BJEPYKJPYRNKOW-UHFFFAOYSA-L malate(2-) Chemical compound [O-]C(=O)C(O)CC([O-])=O BJEPYKJPYRNKOW-UHFFFAOYSA-L 0.000 description 3
- 239000011572 manganese Substances 0.000 description 3
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-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
- 239000012860 organic pigment Substances 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
- 238000002360 preparation method Methods 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- RZRJACCZWZTYJY-UHFFFAOYSA-N tert-butylsulfanyl n,n-dimethylcarbamodithioate Chemical compound CN(C)C(=S)SSC(C)(C)C RZRJACCZWZTYJY-UHFFFAOYSA-N 0.000 description 3
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 description 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- VSIYJQNFMOOGCU-UHFFFAOYSA-N 1-(cyclohexen-1-yl)cyclohexene Chemical group C1CCCC(C=2CCCCC=2)=C1 VSIYJQNFMOOGCU-UHFFFAOYSA-N 0.000 description 2
- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 description 2
- 125000006030 1-methyl-3-butenyl group Chemical group 0.000 description 2
- 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 2
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- RFMXKZGZSGFZES-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;2-sulfanylacetic acid Chemical compound OC(=O)CS.OC(=O)CS.OC(=O)CS.CCC(CO)(CO)CO RFMXKZGZSGFZES-UHFFFAOYSA-N 0.000 description 2
- PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 description 2
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- BNCADMBVWNPPIZ-UHFFFAOYSA-N 2-n,2-n,4-n,4-n,6-n,6-n-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical compound COCN(COC)C1=NC(N(COC)COC)=NC(N(COC)COC)=N1 BNCADMBVWNPPIZ-UHFFFAOYSA-N 0.000 description 2
- 125000003504 2-oxazolinyl group Chemical group O1C(=NCC1)* 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 2
- QMYGFTJCQFEDST-UHFFFAOYSA-N 3-methoxybutyl acetate Chemical compound COC(C)CCOC(C)=O QMYGFTJCQFEDST-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- 125000006042 4-hexenyl group Chemical group 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- YYLLIJHXUHJATK-UHFFFAOYSA-N Cyclohexyl acetate Chemical compound CC(=O)OC1CCCCC1 YYLLIJHXUHJATK-UHFFFAOYSA-N 0.000 description 2
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- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 1
- 239000002116 nanohorn Substances 0.000 description 1
- MZYHMUONCNKCHE-UHFFFAOYSA-N naphthalene-1,2,3,4-tetracarboxylic acid Chemical class C1=CC=CC2=C(C(O)=O)C(C(=O)O)=C(C(O)=O)C(C(O)=O)=C21 MZYHMUONCNKCHE-UHFFFAOYSA-N 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 1
- 125000005029 naphthylthio group Chemical group C1(=CC=CC2=CC=CC=C12)S* 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005485 noradamantyl group Chemical group 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 239000004843 novolac epoxy resin Substances 0.000 description 1
- XVKLLVZBGMGICC-UHFFFAOYSA-N o-[3-propanethioyloxy-2,2-bis(propanethioyloxymethyl)propyl] propanethioate Chemical compound CCC(=S)OCC(COC(=S)CC)(COC(=S)CC)COC(=S)CC XVKLLVZBGMGICC-UHFFFAOYSA-N 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-N pent-4-enoic acid Chemical compound OC(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- NCHIGRUKPIGGQF-UHFFFAOYSA-N pentane-1,1-dithiol Chemical compound CCCCC(S)S NCHIGRUKPIGGQF-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical class C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical compound C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical group O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920005575 poly(amic acid) Polymers 0.000 description 1
- 229920005670 poly(ethylene-vinyl chloride) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001228 polyisocyanate Chemical class 0.000 description 1
- 239000005056 polyisocyanate Chemical class 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- NCNISYUOWMIOPI-UHFFFAOYSA-N propane-1,1-dithiol Chemical compound CCC(S)S NCNISYUOWMIOPI-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 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
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical class C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 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
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 150000003346 selenoethers Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 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
- 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
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical class S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
- 229940103494 thiosalicylic acid Drugs 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 229940096522 trimethylolpropane triacrylate Drugs 0.000 description 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
- 150000004961 triphenylmethanes Chemical class 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 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
- 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
- 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
- XKMZOFXGLBYJLS-UHFFFAOYSA-L zinc;prop-2-enoate Chemical compound [Zn+2].[O-]C(=O)C=C.[O-]C(=O)C=C XKMZOFXGLBYJLS-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
-
- 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
-
- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
- C08F290/12—Polymers provided for in subclasses C08C or C08F
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
Definitions
- the present invention has a latent additive, an ethylenically unsaturated bond, and a hydrophilic group that are inactive at normal temperature and activated by heating to a predetermined temperature to exhibit a function, and are constant.
- the present invention relates to a photosensitive composition containing a polymer having a double bond equivalent of: Furthermore, the present invention relates to a colored photosensitive composition that can be polymerized by energy rays using the composition, and a color filter that uses the colored photosensitive composition.
- Patent Document 1 In order to improve the weather resistance and heat resistance of a resin composition, a method of stabilizing by adding an ultraviolet absorber or an antioxidant is known (Patent Document 1).
- Patent Document 6 Since phenolic antioxidants trap radicals that greatly affect the deterioration of the polymer, adding antioxidants to the polymerization system generally acts as a so-called polymerization inhibitor, causing inhibition of curing. Therefore, latent additives have been developed (Patent Document 6).
- an object of the present invention is to have a latent additive, an ethylenically unsaturated bond and a hydrophilic group in one molecule which are inactive at room temperature and are activated by heating to a predetermined temperature to exhibit a function.
- Another object of the present invention is to provide a photosensitive composition comprising a polymer having a certain double bond equivalent, an acrylic monomer, and a radical photopolymerization initiator.
- the present invention has been made on the basis of the above findings, and is a latent additive (A) that is inactive at room temperature and is activated by heating to a predetermined temperature to express its function (hereinafter, the latent additive ( A)), a polymer (B) having an ethylenically unsaturated bond and a hydrophilic group in one molecule and having a double bond equivalent of 200 to 1000 (hereinafter also referred to as polymer (B))
- the photosensitive composition containing an acrylic monomer (C) and a radical photopolymerization initiator (D) is provided.
- the photosensitive composition of the present invention comprises a latent additive (A), a polymer (B) having an ethylenically unsaturated bond and a hydrophilic group in one molecule and a double bond equivalent of 200 to 1000, Contains an acrylic monomer (C) and a radical photopolymerization initiator (D).
- a latent additive A
- B a polymer having an ethylenically unsaturated bond and a hydrophilic group in one molecule and a double bond equivalent of 200 to 1000
- C acrylic monomer
- D radical photopolymerization initiator
- the latent additive (A) used in the photosensitive composition of the present invention is inactive at room temperature or in the pre-baking step, and is heated at 100 to 250 ° C. or 80 to 200 ° C. in the presence of an acid / base catalyst. The protecting group is eliminated and becomes active by heating with.
- the latent additive (A) is active, it means that it has reactivity with radicals, and when it is inactive, it means that it does not react with radicals or has extremely low reactivity.
- the latent additive (A) has a skeleton represented by the following general formula (I) because synthesis is easy and heat resistance is high.
- ring A 1 represents a 5-membered or 6-membered hydrocarbon ring, heterocyclic ring or condensed ring;
- R 61 each independently has a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, a C 1-40 alkyl group that may have a substituent, or a substituent.
- 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
- the methylene group in the alkyl group or arylalkyl group represented by R 61 and R 62 is a carbon-carbon double bond, —O—, —S—, —CO—, —O—CO—, —CO—O.
- a group selected from —, —NH—CO—, —NH—CO—O—, —NR′—, —SS— or —SO 2 — is replaced with a group which is combined under the condition that oxygen atoms are not adjacent to each other.
- R ′ represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- a plurality of R 61 may be bonded to each other to form a benzene ring or a naphthalene ring
- d represents an integer of 0 to 4
- k represents an integer of 1 to 5, but the sum of d and k is less than the number of substituents that ring A 1 can take;
- * Means that it is bonded to an adjacent group at the * part. )
- the heterocyclic group having 2 to 20 carbon atoms means a group containing at least one heterocyclic ring and having 2 to 20 carbon atoms in the whole group.
- the heterocycle-containing group having 2 to 10 carbon atoms described later means a group containing at least one heterocycle and having 2 to 10 carbon atoms as a whole.
- the heterocycle-containing group having 2 to 35 carbon atoms described later means a group containing at least one heterocycle and having 2 to 35 carbon atoms as a whole.
- the number of carbon atoms of the whole group may exceed the upper limit of each group.
- examples of the substituent include those exemplified as the substituent that may substitute a group represented by X 1 described later.
- Examples of the five-membered hydrocarbon ring represented by A 1 in the general formula (I) include cyclopentadiene, and examples of the five-membered heterocyclic ring include furan, thiophene, pyrrole, pyrrolidine, pyrazolidine, and pyrazole.
- Imidazole imidazolidine, oxazole, isoxazole, isoxazolidine, thiazole, isothiazole, isothiazolidine, etc., as the six-membered hydrocarbon ring, benzene and the like, and as the six-membered heterocyclic ring, Piperidine, piperazine, morpholine, thiomorpholine, pyridine, pyrazine, pyrimidine, pyridazine, triazine, etc. are mentioned, and these rings may be condensed or substituted with other rings.
- quinoline isoquinoline, indole, urolidine, ben
- examples include zoxazole, benzotriazole, azulene, naphthalene, anthracene, fluorene, perylene, and pyrene.
- halogen atom represented by R 61 in the general formula (I) examples include fluorine, chlorine, bromine and iodine. (In the description below, 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 in the general formula (I) 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,
- Substituents for substituting the heterocyclic ring-containing groups include ethylenically unsaturated groups such as vinyl, allyl, acrylic and methacryl; halogen atoms such as fluorine, chlorine, bromine and iodine; acetyl, 2-chloroacetyl, propionyl and octanoyl
- Acyl groups such as acryloyl, methacryloyl, phenylcarbonyl (benzoyl), phthaloyl, 4-trifluoromethylbenzoyl, pivaloyl, salicyloyl, oxaloyl, stearoyl, methoxycarbonyl, ethoxycarbonyl, t-but
- Examples of the aryl group having 6 to 20 carbon atoms represented by R 61 and R 62 in the general formula (I) 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-di
- Examples of the arylalkyl group having 7 to 20 carbon atoms represented by R 61 and R 62 in the general formula (I) include benzyl, 1-methyl-1-phenylethyl, 1-naphthylmethyl, 9-anthracenyl Examples include methyl, 9-fluorenyl, 3-phenylpropyl, methyl-2-phenylpropan-2-yl, diphenylmethyl, triphenylmethyl, phenethyl, styryl, cinnamyl and the like.
- Examples of the heterocyclic ring-containing group having 2 to 20 carbon atoms represented by R 61 and R 62 in the general formula (I) include a pyridine ring, a pyrimidine ring, a pyridazine ring, a piperidine ring, a pyran ring, a pyrazoline ring, and a triazine ring.
- Examples of the alkyl group having 1 to 20 carbon atoms represented by R 62 in the general formula (I) include those satisfying a predetermined number of carbon atoms among the alkyl groups represented by R 61 .
- Examples of the alkenyl group having 2 to 20 carbon atoms represented by R 62 in the general formula (I) include vinyl, 1-methylethen-1-yl, propen-1-yl, propen-2-yl and propene-3. -Yl, buten-1-yl, buten-2-yl, 2-methylpropen-3-yl, 1,1-dimethylethen-2-yl, 1,1-dimethylpropen-3-yl, 3-butenyl, Examples include 1-methyl-3-butenyl, isobutenyl, 3-pentenyl, 4-hexenyl, cyclohexenyl, bicyclohexenyl, heptenyl, octenyl, decenyl, pentadecenyl, eicosenyl, tricoseni and the like.
- Examples of the trialkylsilyl group represented by R 62 in the general formula (I) include alkyl groups having 1 to 6 carbon atoms such as trimethylsilane, triethylsilane, and ethyldimethylsilane (the three alkyl groups may be the same or different. Silyl group substituted with (good).
- Examples of the alkyl group having 1 to 8 carbon atoms represented by R ′ in the general formula (I) include those satisfying a predetermined number of carbon atoms among the alkyl groups represented by R 61 .
- R 61 is preferably a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or an aryl group having 6 to 12 carbon atoms because synthesis is easy.
- R 62 is an alkyl group having 1 to 8 carbon atoms in which —CO—O— is bonded to the terminal on the oxygen atom side and functions effectively as a latent additive. Is preferable.
- X 1 represents an m-valent organic group, specifically, a direct bond, a hydrogen atom, a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, the following (Ia ) Or (Ib),>C ⁇ O,> NR 63 , —OR 63 , —SR 63 , —NR 63 R 64 , or the same number as m which may have a substituent.
- the methylene group is a carbon-carbon double bond, —O—, —S—, —CO—, —O—CO—, —CO—O—, —O—CO—O—, —O—CO—O.
- X 1 is a nitrogen atom, a phosphorus atom or a group represented by the following (Ia) or (Ib), m is 3, X 1 is an oxygen atom or a sulfur atom, and> C ⁇ O , —NH—CO—, —CO—NH— or> NR 63 , m is 2, and when X 1 is —OR 63 , —SR 63 or —NR 63 R 64 , m is 1. X 1 may form a ring together with A 1 .
- the latent additive represented by the general formula (IA) has a structure in which m specific groups are bonded to the m-valent specific atom or group represented by X 1 .
- 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.
- m is monovalent, for example, methyl Ethyl, propyl, isopropyl, cyclopropyl, butyl, sec-butyl, sec-butyl, isobutyl, amyl, isoamyl, tert-amyl, cyclopentyl, hexyl, 2-hexyl, 3-hexyl, cyclohexyl, bicyclohexyl, 1-methyl Alkyl groups such as cyclohexyl, heptyl, 2-heptyl, 3-heptyl, isoheptyl, tertiary heptyl, n-octyl, isooctyl, tertiary octyl, 2-ethylhexyl, nonyl, isononyl,
- the aliphatic hydrocarbon group having 1 to 120 carbon atoms having the same valence as m represented by X 1 is methylene, ethylene where m is divalent.
- Alkylene such as propylene, butylene, butyldiyl, etc .; in which the methylene chain of the alkylene is replaced by —O—, —S—, —CO—O—, —O—CO—; ethanediol, propanediol, butanediol, Residues of diols such as pentanediol and hexanediol; residues of dithiols such as ethanedithiol, propanedithiol, butanedithiol, pentanedithiol and hexanedithiol, and groups in which these groups are substituted by substituents described later, etc. .
- Examples of the aliphatic hydrocarbon group having 1 to 120 carbon atoms and having the same valence as m represented by X 1 in the general formula (IA) are those in which m is trivalent. Examples thereof include alkylidine such as pyridine and 1,1,3-butyridine, and groups in which these groups are substituted with a substituent described later.
- M is monovalent, arylalkyl groups such as benzyl, phenethyl, diphenylmethyl, triphenylmethyl, styryl and cinnamyl; aryl groups such as phenyl and naphthyl; aryloxy groups such as phenoxy and naphthyloxy; phenylthio and naphthylthio And arylthio groups such as these, and groups in which these groups are substituted with a substituent described later.
- 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 groups in which these groups are substituted with a substituent described later.
- m is As monovalent ones, pyridyl, pyrimidyl, pyrariayl, piperidyl, pyranyl, pyrazolyl, triazyl, pyrrolyl, quinolyl, isoquinolyl, imidazolyl, benzoimidazolyl, triazolyl, furyl, furanyl, benzofuranyl, thienyl, thiophenyl, benzothiophenyl, thiadiazolyl, thiazolyl, Benzothiazolyl, oxazolyl, benzoxazolyl, isothiazolyl, isoxazolyl, indolyl, 2-pyrrolidinon-1-yl, 2-piperidone-1-yl, 2,4-dioxyimidazolidin-3-yl
- m is examples of the divalent group include 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 with a substituent described later. .
- m is
- the trivalent group 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 an aliphatic hydrocarbon group having 1 to 120 carbon atoms represented by the above X 1 Among the combinations of an aromatic hydrocarbon group or the aliphatic hydrocarbon group and a substituent described later, those satisfying a predetermined number of carbon atoms can be mentioned.
- an aliphatic hydrocarbon group having 1 to 120 carbon atoms, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, and a heterocyclic ring-containing group having 2 to 35 carbon atoms represented by X 1 may be substituted.
- substituents that may be substituted for the heterocyclic ring-containing groups 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, stearo Acyl groups such as acetyloxy, benzoyloxy, etc .; amino, ethylamino
- Examples of the alkyl group having 1 to 8 carbon atoms represented by R ′ in the general formula (IA) include those having the predetermined number of carbon atoms among the alkyl groups represented by R 61 described above. Can be mentioned.
- X 1 when m is 2, X 1 can also be represented by the following general formula (1).
- Y 10 represents a single bond, —CR 65 R 66 —, —NR 67 —, a divalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, or 6 to 35 carbon atoms.
- the terminal carbon atom of the aliphatic hydrocarbon group may be replaced with —O—, —S—, —CO—, —COO—, —OCO— or —NH—
- the aliphatic hydrocarbon group may be substituted with a hydroxyl group, a halogen atom, a cyano group, a nitro group, a carboxyl group or an alkoxy group
- Z 1 and Z 2 are each independently a direct bond, —O—, —S—,> CO, —CO—O—, —O—CO—, —SO 2 —, —SS—, —SO—,
- Represents> NR 67 or> PR 67 , R 65 , R 66 and R 67 each independently have a hydrogen atom, a hydroxyl group or a substituent, or may have an aliphatic hydrocarbon group having 1 to 35 carbon atoms 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 may have a substituent
- f is an integer of 0 to 5
- * means that it is bonded to an adjacent group at the * portion.
- 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 replaced with an unsaturated bond, —O— or —S—, R 73 may form a ring with adjacent R 73 , p represents
- X 1 can also be represented by the following general formula (2).
- Y 11 represents a single bond, a trivalent aliphatic hydrocarbon group having 3 to 35 carbon atoms, a trivalent alicyclic hydrocarbon group having 3 to 35 carbon atoms, 3 A valent aromatic hydrocarbon group having 6 to 35 carbon atoms or a trivalent heterocyclic group having 2 to 35 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 or> PR 68 , R 68 is a hydrogen atom, an aliphatic hydrocarbon group having 1 to 35 carbon atoms which may have a substituent, or an aromatic carbon group having 6 to 35 carbon atoms which may have a substituent.
- the adjacent carbon atom of the aliphatic hydrocarbon group is interrupted by a carbon-carbon double bond, —O—, —CO—, —O—CO—, —CO—O— or —SO 2 —.
- the terminal carbon atom of the aliphatic hydrocarbon group may be replaced with a carbon-carbon double bond, —O—, —CO—, —O—CO—, —CO—O— or —SO 2 —. is there. )
- X 1 when m is 4, X 1 can also be represented by the following general formula (3).
- Y 12 represents a single bond, a carbon atom, or a tetravalent aliphatic hydrocarbon group having 1 to 35 carbon atoms and a tetravalent aromatic carbon group having 6 to 35 carbon atoms.
- the adjacent carbon atom of the aliphatic hydrocarbon group may be interrupted by —COO—, —O—, —OCO—, —NHCO—, —NH— or —CONH—
- the terminal carbon atom of the aliphatic hydrocarbon group may be replaced with —COO—, —O—, —OCO—, —NHCO—, —NH— or —CONH—
- Z 1 to Z 4 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 13 represents a single bond, a 5-valent aliphatic hydrocarbon group having 2 to 35 carbon atoms, a 5-valent aromatic hydrocarbon group having 6 to 20 carbon atoms, or a pentavalent group.
- the adjacent carbon atom of the aliphatic hydrocarbon group may be interrupted by —COO—, —O—, —OCO—, —NHCO—, —NH— or —CONH—
- the terminal carbon atom of the aliphatic hydrocarbon group may be replaced with —COO—, —O—, —OCO—, —NHCO—, —NH— or —CONH—
- Z 1 to Z 5 are each independently a group within the same range as the group represented by Z 1 to Z 3 in the general formula (2).
- Y 14 is a single bond, a hexavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms, a hexavalent aromatic hydrocarbon group having 6 to 35 carbon atoms, or a hexavalent group.
- the adjacent carbon atom of the aliphatic hydrocarbon group may be interrupted by —COO—, —O—, —OCO—, —NHCO—, —NH— or —CONH—
- the terminal carbon atom of the aliphatic hydrocarbon group may be replaced with —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 includes the general formula (I- A monovalent aliphatic hydrocarbon group having 1 to 120 carbon atoms exemplified as the m-valent organic group represented by X 1 in A) and these groups are represented by X 1 in the general formula (IA).
- Examples include groups substituted by those exemplified as the substituent of the group representing the organic group, and these groups or 2 exemplified as the m-valent organic group represented by X 1 in the general formula (IA).
- the heterocyclic group containing 2 to 35 carbon atoms which may have a substituent represented by R 65 , R 66 and R 67 is represented by X 1 in the above general formula (IA).
- the monovalent heterocyclic group having 2 to 35 carbon atoms exemplified as the m-valent organic group and these groups represent the m-valent organic group represented by X 1 in the general formula (IA).
- Examples of the divalent group in which the aromatic ring-containing hydrocarbon group having 2 to 35 is substituted with Z 1 and Z 2 include the divalent heterocyclic group having 2 to 35 carbon atoms represented by Y 10. .
- examples of the cycloalkyl group having 3 to 10 carbon atoms represented by R 71 include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl and the like.
- the alkyl group having 1 to 10 carbon atoms represented by R 72 is exemplified as the alkyl group having 1 to 40 carbon atoms represented by R 61 .
- the groups satisfying a predetermined number of carbon atoms can be mentioned.
- examples of the alkoxy group having 1 to 10 carbon atoms represented by R 72 include methyloxy, ethyloxy, propyloxy, isopropyloxy, butyloxy, sec-butyloxy, Tributyloxy, isobutyloxy, amyloxy, isoamyloxy, tertiary amyloxy, hexyloxy, cyclohexyloxy, heptyloxy, isoheptyloxy, tertiary heptyloxy, n-octyloxy, isooctyloxy, tertiary octyloxy, 2-ethylhexyl Examples include oxy, nonyloxy, decyloxy and the like.
- the substituent of the phenyl group, alkyl group, alkoxy group and alkenyl group is an m-valent organic compound represented by X 1 in the general formula (IA). The same as those exemplified as the substituent of the group representing the group.
- the alkyl group having 1 to 10 carbon atoms which may have a substituent represented by R 73 and R 74 is represented by R 61.
- R 61 groups satisfying a predetermined number of carbon atoms are exemplified.
- the aryl group having 6 to 20 carbon atoms, which may have a substituent represented by R 73 and R 74 includes R 61 and R 62 Examples thereof include the groups exemplified as the aryl group having 6 to 20 carbon atoms.
- the aryloxy group having 6 to 20 carbon atoms which may have a substituent represented by R 73 and R 74 includes 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-
- the arylthio group having 6 to 20 carbon atoms which may have a substituent represented by R 73 and R 74 has the above substituent.
- a group in which the oxygen atom of the aryloxy group having 6 to 20 carbon atoms is substituted with a sulfur atom is used.
- the arylalkenyl group having 6 to 20 carbon atoms, which may have a substituent represented by R 73 and R 74 has the above substituent.
- the oxygen atom of the aryloxy group having 6 to 20 carbon atoms may be vinyl, allyl, 1-propenyl, isopropenyl, 2-butenyl, 1,3-butadienyl, 2-pentenyl, 2-octenyl, etc. And a group substituted with an alkenyl group.
- the arylalkyl group having 7 to 20 carbon atoms represented by R 73 and R 74 includes 7 to 20 carbon atoms represented by R 61 and R 62.
- the groups exemplified as the arylalkyl group are examples of the arylalkyl group.
- the heterocyclic group containing 2 to 20 carbon atoms which may have a substituent represented by R 73 and R 74 includes R 61 and R And the groups exemplified as the heterocyclic-containing group having 2 to 20 carbon atoms represented by 62 .
- 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 1 in the general formula (IA).
- Examples of the group substituted by 1 include those having a predetermined number of carbon atoms, such as trivalent groups substituted with Z 1 , Z 2 and Z 3 .
- 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.
- the trivalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by Y 11 in the general formula (2) is an m-valent represented by X 1 in the general formula (IA).
- Examples of monovalent to trivalent aromatic ring-containing hydrocarbon groups exemplified as the organic group and substituents of the groups in which these groups represent the m-valent organic group represented by X 1 in the general formula (IA) And a trivalent group in which a group substituted by the above is substituted with Z 1 , Z 2 and Z 3 .
- Examples of the trivalent heterocyclic group having 2 to 35 carbon atoms represented by Y 11 in the general formula (2) include an m-valent organic group represented by X 1 in the general formula (IA).
- the aromatic hydrocarbon group having 6 to 35 and the heterocyclic group having 2 to 35 carbon atoms which may have a substituent include R 65 and R 66 in the general formula (1), respectively.
- Examples include the aliphatic hydrocarbon group, aromatic ring-containing hydrocarbon group, and heterocyclic ring-containing group exemplified in the description.
- the tetravalent aliphatic hydrocarbon group having 1 to 35 carbon atoms represented by Y 12 in the general formula (3) is an m-valent organic compound represented by X 1 in the general formula (IA).
- Examples of the group substituted by 1 include those having a predetermined number of carbon atoms, such as tetravalent groups substituted with Z 1 , Z 2 , Z 3 and Z 4 .
- the aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by Y 12 in the general formula (3) is an m-valent organic group represented by X 1 in the general formula (IA).
- X 1 in the general formula (IA) By the exemplified monovalent to trivalent aromatic ring-containing hydrocarbon groups and those exemplified as substituents for the group representing the m-valent organic group represented by X 1 in the general formula (IA). Examples thereof include a tetravalent group in which a substituted group or the like is substituted with Z 1 , Z 2 , Z 3, or Z 4 .
- the tetravalent heterocyclic containing group having a carbon number of 2 to 35 represented by Y 12 in general formula (3), m-valent organic group represented by X 1 in the above formula (I-A) The monovalent to trivalent heterocyclic-containing groups exemplified as above and these groups substituted by those exemplified as the substituents of the group representing the m-valent organic group represented by X 1 in the general formula (IA) And tetravalent groups in which the group and the like are substituted with Z 1 , Z 2 , Z 3 and Z 4 .
- 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 1 in the general formula (IA).
- Examples of monovalent to trivalent aliphatic hydrocarbon groups exemplified as the groups and substituents of the groups in which these groups represent the m-valent organic group represented by X 1 in the general formula (IA) Among the groups substituted by the above, there are pentavalent groups in which those satisfying the predetermined number of carbon atoms are substituted with Z 1 , Z 2 , Z 3 , Z 4 and Z 5 .
- the pentavalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by Y 14 in the general formula (4) is an m-valent represented by X 1 in the general formula (IA).
- Examples of monovalent to trivalent aromatic ring-containing hydrocarbon groups exemplified as organic groups and substituents of groups in which these groups represent an n-valent organic group represented by X 1 in the above general formula (IA)
- a pentavalent group in which a group substituted by the above-described one is substituted with Z 1 , Z 2 , Z 3 , Z 4 and Z 5 .
- the pentavalent C2-C35 heterocycle-containing group represented by Y 14 in the general formula (4) is X in the m valence represented by X 1 in the general formula (IA).
- X 1 in the general formula (IA) Of the monovalent to trivalent heterocyclic group exemplified as the represented n-valent organic group and the group in which these groups represent the m-valent organic group represented by X 1 in the general formula (IA). Examples thereof include pentavalent groups in which groups substituted by those exemplified as the substituent are substituted with Z 1 , Z 2 , Z 3 , Z 4 and Z 5 .
- 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 1 in the general formula (IA).
- Examples of the group substituted by the above group include those having a predetermined number of carbon atoms and the like, and hexavalent groups substituted with Z 1 , Z 2 , Z 3 , Z 4 , Z 5 and Z 6 .
- the hexavalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by Y 14 in the general formula (5) is an m-valent represented by X 1 in the general formula (IA).
- Examples of monovalent to trivalent aromatic ring-containing hydrocarbon groups exemplified as the organic group and substituents of the groups in which these groups represent the m-valent organic group represented by X 1 in the general formula (IA)
- a hexavalent group in which a group substituted by the above-described one is substituted with Z 1 , Z 2 , Z 3 , Z 4 , Z 5 and Z 6 .
- the hexavalent heterocyclic group having 2 to 35 carbon atoms represented by Y 14 in the general formula (5) is an m-valent organic group represented by X 1 in the general formula (IA).
- hexavalent to groups substituted by those exemplified as the substituents exemplified monovalent to trivalent heterocyclic containing groups is substituted with Z 1, Z 2, Z 3 , Z 4, Z 5 and Z 6 as And the like.
- the sum of d and k is less than the number of substituents that can be taken by the ring A 1 .
- the possible substituents of the ring A 1 are 6, and d + k ⁇ 5.
- the possible substituents of the ring A 1 are 4, and d + k ⁇ 3.
- 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 group containing 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 (I).)
- X 2 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.
- 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.
- 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 (I)
- ring A 2 is (It is the same as general formula (II).)
- 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 (II) include those exemplified in the description of A 1 in the general formula (I).
- the halogen atom represented by R 81 , R 82 , R 83 , R 84 and R 85 in the general formula (II) an alkyl group having 1 to 40 carbon atoms which may have a substituent, a carbon atom
- Examples of the aryl group having 6 to 20 carbon atoms, the arylalkyl group having 7 to 20 carbon atoms, and the heterocyclic ring-containing group having 2 to 20 carbon atoms are exemplified in the description of R 61 or R 62 in the general formula (I).
- 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
- Examples of the 20 aryl group, 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 (I). It is done.
- Examples of the 20 aryl group, 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 (I). It is done.
- Ring A 2 is preferably benzene or naphthalene
- 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 and heterocycle-containing groups having 2 to 10 carbon atoms are preferred.
- any one of R 81 to R 85 is an alkyl group having 1 to 4 carbon atoms or a heterocycle 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 be a direct bond, —CO—O—, —O—
- groups other than hydrogen atoms include aryl groups having 6 to 10 carbon atoms, arylalkyl groups having 7 to 12 carbon atoms, and those having 2 to 10 carbon atoms.
- Heterocycle-containing groups particularly those in which any one of R 91 to R 94 is an alkyl group having 1 to 4 carbon atoms or a heterocycle-containing group having 2 to 10 carbon atoms are preferred.
- 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 group having 7 to 10 carbon atoms (particularly benzyl group). 2 to 6 carbon atoms Alkenyl group (especially propen-1-yl group)
- Y 10 is a sulfur atom, a divalent alkyl group having 1 to 20 carbon atoms.
- Divalent aromatic ring-containing hydrocarbon group having 6 to 25 carbon atoms, divalent heterocyclic group containing 2 to 21 carbon atoms, 2,4,8,10-tetraoxaspiro [5,5] undecane In particular, a divalent alkyl group having 1 to 15 carbon atoms, a divalent aromatic ring-containing hydrocarbon group having 6 to 15 carbon atoms, 2,4,8,10-tetraoxaspiro [5,5] undecane
- Z 1 and Z 2 may have a direct bond, —CO—O—, —O—CO— or a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.
- Y 11 is a trivalent alkyl group having 1 to 20 carbon atoms, trivalent An aryl group having 6 to 10 carbon atoms, a trivalent arylalkyl group having 7 to 12 carbon atoms, a trivalent heterocyclic group having 2 to 10 carbon atoms, particularly a trivalent carbon atom having 1 to 8 carbon atoms.
- An alkyl group, a trivalent aryl group having 6 to 9 carbon atoms, and a trivalent heterocyclic group having 1 to 6 carbon atoms, Z 1 , Z 2 and Z 3 are each a direct bond, —CO—O—, —O—CO— or a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.
- a divalent aromatic hydrocarbon group having 6 to 10 carbon atoms, particularly a divalent aliphatic hydrocarbon group having 1 to 8 carbon atoms which may have a substituent is preferable.
- Y 12 represents a tetravalent alkyl group having 1 to 20 carbon atoms, a tetravalent group.
- An alkyl group, a tetravalent aryl group having 6 to 9 carbon atoms, and a tetravalent hetero ring-containing group having 1 to 6 carbon atoms, Z 1 to Z 4 are a direct bond, —CO—O—, —O—CO— or a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.
- Y 13 is a pentavalent alkyl group having 1 to 20 carbon atoms, pentavalent An aryl group having 6 to 10 carbon atoms, an arylalkyl group having 5 to 7 carbon atoms, a 5-valent heterocyclic group having 2 to 10 carbon atoms, particularly a pentavalent carbon atom having 1 to 8 carbon atoms.
- An alkyl group, a pentavalent aryl group having 6 to 9 carbon atoms, and a pentavalent hetero ring-containing group having 1 to 6 carbon atoms, Z 1 to Z 5 are each a direct bond, —CO—O—, —O—CO— or a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.
- Y 14 is a hexavalent alkyl group having 1 to 20 carbon atoms, hexavalent Aryl groups having 6 to 10 carbon atoms, arylalkyl groups having 6 to 7 carbon atoms, heterocyclic groups having 6 to 6 carbon atoms, particularly hexavalent carbon atoms having 1 to 8 carbon atoms.
- Z 1 to Z 6 are a direct bond, —CO—O—, —O—CO— or a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.
- heterocyclic group having 2 to 10 carbon atoms described above examples include the heterocyclic group having 1 to 10 carbon atoms in the compounds exemplified as the heterocyclic group having 2 to 35 carbon atoms described above. It is done.
- the content of the latent additive (A) is preferably 0.001 to 20% by mass, and more preferably 0.005 to 5% by mass.
- the polymer (B) used in the photosensitive composition of the present invention is a polymer having an ethylenically unsaturated bond and a hydrophilic group in one molecule and having a double bond equivalent of 200 to 1,000.
- the hydrophilic group possessed by the polymer (B) include a hydroxyl group, a thiol group, a carboxyl group, a sulfo group, an amino group, an amide group, or a salt thereof. This is preferable because of its high solubility in water.
- the preferred functional group equivalent of the hydrophilic group in the polymer (B) (the mass of the polymer containing 1 equivalent of hydrophilic group) is 50 to 10,000.
- a preferred mass average molecular weight of the polymer (B) is 3000 to 50000.
- Examples of the polymer (B) include (meth) acrylic acid, ⁇ -chloroacrylic acid, itaconic acid, maleic acid, citraconic acid, fumaric acid, hymic acid, crotonic acid, isocrotonic acid, vinyl acetic acid, allyl acetic acid, and cinnamic acid. Sorbic acid, mesaconic acid, succinic acid mono [2- (meth) acryloyloxyethyl], phthalic acid mono [2- (meth) acryloyloxyethyl], ⁇ -carboxypolycaprolactone mono (meth) acrylate, etc.
- Hydroxyl-containing polyfunctional amine Rate and succinic anhydride phthalic acid anhydride, a polyfunctional acrylate having an acid value which is a reaction product of a dibasic acid anhydride such as tetrahydrophthalic anhydride.
- X 41 is a direct bond, an alkylene group having 1 to 4 carbon atoms which may have a substituent, or an alicyclic group having 3 to 20 carbon atoms which may have a substituent.
- Hydrocarbon group, —O—, —S—, —SO 2 —, —SS—, —SO—, —CO—, —OCO— or a substitution represented by the above (1-1) to (1-3) Represents a group, R 41 , R 42 , R 43 and R 44 each independently have a hydrogen atom, a substituent or a C 1-5 alkyl group or a substituent.
- those having at least one selected from units represented by the following general formula (VI-4) are preferred because of their high developability and heat resistance.
- Y 1 represents a hydrogen atom or a methyl group
- X 4 represents a divalent linking group
- R 1 represents an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms
- arylalkyl group having 7 to 30 carbon atoms
- the hydrogen atom of the alkyl group, aryl group and arylalkyl group may be substituted with a halogen atom, a hydroxyl group, a nitro group or an epoxy group
- methylene groups in arylalkyl groups may be replaced by linking groups of —O—, —S—, —CO—, —COO—, —OCO— or —NH—, or combinations thereof.
- R 2 , R 3 and R 4 are each independently a hydrogen atom or a methyl group.
- the divalent linking group represented by X 4 in the general formula (VI-2) is not particularly limited, but preferred examples include the structure represented by the general formula (1).
- R 1 is preferably an alkyl group having 1 to 8 carbon atoms and an arylalkyl group having 7 to 30 carbon atoms, and more preferably an alkyl group having 1 to 4 carbon atoms.
- X 4 is a structure in which a divalent linking group is represented by the following general formula (1), Y 10 is preferably an alkylene group having 1 to 15 carbon atoms, and has 7 carbon atoms having a cycloalkylene group. Those having a substituent having ⁇ 15 alkylene groups or carboxyl groups are more preferred.
- the hydrogen atom in these alkylene groups may be substituted with a halogen atom, a hydroxyl group or a nitro atom, and the methylene group in the chain alkylene portion in the alkylene group is —O—, —S—, —CO. It may be replaced by a —, —COO—, —OCO— or —NH— group.
- Z 1 and Z 2 are preferably direct bonds.
- the polymer (B) has an acid value of preferably 10 to 200 mg / KOH, more preferably 30 to 150 mg / KOH. If the acid value is less than 10 mg / KOH, sufficient alkali developability may not be obtained, and if it is greater than 200 mg / KOH, the production of the polymer (B) may be difficult.
- the acid value is based on JIS K 0050 and JIS K 0211.
- the polymer (B) must have a double bond equivalent of 200 to 1000, preferably 300 to 500. If the double bond equivalent in the polymer (B) is less than 200, production is difficult, and if it is greater than 1000, sufficient durability cannot be obtained.
- the content of the polymer (B) is preferably 1 to 20% by mass, particularly preferably 5 to 15% by mass in the photosensitive composition of the present invention.
- the content of the polymer (B) is less than 1% by mass, resolution and durability may not be sufficiently obtained.
- the content is more than 20% by mass, alkali developability and curability may not be sufficiently obtained. There is.
- the acrylic monomer (C) used in the photosensitive composition of the present invention is not particularly limited and known ones can be used.
- the content of the acrylic monomer (C) is preferably 1 to 20% by mass, particularly preferably 5 to 15% by mass in the photosensitive composition of the present invention.
- the content of the acrylic monomer (C) is less than 1% by mass, sufficient curability and alkali developability may not be obtained.
- the content is more than 20% by mass, sufficient resolution and durability may not be obtained. There is.
- the radical photopolymerization initiator (D) used in the photosensitive composition of the present invention may be any compound that can initiate radical polymerization upon receiving light irradiation, such as an acetophenone compound or a benzyl compound.
- Preferred examples include compounds, ketone compounds such as benzophenone compounds and thioxanthone compounds, and oxime compounds.
- acetophenone compounds include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 4′-isopropyl-2-hydroxy-2-methylpropiophenone, and 2-hydroxymethyl-2.
- benzylic compound examples include benzyl and anisyl.
- benzophenone compounds include benzophenone, methyl o-benzoylbenzoate, Michler's ketone, 4,4′-bisdiethylaminobenzophenone, 4,4′-dichlorobenzophenone, 4-benzoyl-4′-methyldiphenyl sulfide, and the like.
- thioxanthone compound examples include thioxanthone, 2-methylthioxanthone, 2-ethylthioxanthone, 2-chlorothioxanthone, 2-isopropylthioxanthone, and 2,4-diethylthioxanthone.
- oxime compound a compound represented by the following general formula (VII) or (VIII) is particularly preferable from the viewpoint of sensitivity and heat resistance.
- R 51 and R 52 each independently have a hydrogen atom, a cyano group, a substituent, or an alkyl group having 1 to 20 carbon atoms or a substituent.
- a certain aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms which may have a substituent or a complex having 2 to 20 carbon atoms which may have a substituent Represents a ring-containing group
- R 53 and R 54 are each independently a halogen atom, nitro group, cyano group, hydroxyl group, carboxyl group, R 55 , OR 56 , SR 57 , NR 58 R 59 , COR 60 , SOR 61 , SO 2 R 62 or CONR 63 R 64 , R 53 and R 54 may be bonded to each other to form a ring, R 55 , R 56 , R 57 , R 58 , R 59 , R 60 , R 61 , R RI
- aryl groups having 6 to 30 carbon atoms which may have substituents arylalkyl groups having 7 to 30 carbon atoms which may have substituents or substituents
- X 5 represents an oxygen atom, a sulfur atom, a selenium atom, CR 75 R 76 , CO, NR 77 or PR 78
- X 6 represents a single bond or CO
- carbon atoms Represents a 6-30 aryl group or an arylalkyl group having 7-30 carbon atoms, and the methylene group in the alkyl group or arylalkyl group contains a halogen atom, a nitro
- R 101 and R 102 each independently represent R 111 , OR 111 , COR 111 , SR 111 , CONR 112 R 113 or CN;
- R 111 , R 112 and R 113 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 111 , R 112 and R 113 Represents a heterocyclic-containing group of formula 2 to 20,
- the hydrogen atoms of the groups represented by R 111 , R 112 and R 113 are further R 121 , OR 121 , COR 121 , SR 121 , NR 122 R 123 , CONR 122 R 123 , —NR 122 —OR 123 , —NCOR 122.
- R 121 , R 122 and R 123 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 Represents a heterocyclic-containing group of formula 2 to 20,
- the hydrogen atom of the group represented by R 121 , R 122 and R 123 may be further substituted with a hydroxyl group, a nitro group, CN, a halogen atom, a hydroxyl group or a carboxyl group,
- the alkyl part of the group represented by R 111 , R 112 , R 113 , R 121 , R 122 , R 123 and R 124 may have a branched side chain or a cyclic alkyl.
- R 103 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 ring-containing group having 2 to 20 carbon atoms.
- the alkyl part of the group represented by R 103 may have a branched side chain or may be a cyclic alkyl, and R 103 and R 107 , R 103 and R 108 , R 104 and R 105 , R 105 and R 106 and R 106 and R 107 may be combined to form a ring, Hydrogen atoms in the group represented by R 103 may further R 121, OR 121, COR 121 , SR 121, NR 122 R 123, CONR 122 R 123, -NR 122 -OR 123, -NCOR 122 -OCOR 123, NR 122 COR 121 , OCOR 121 , COOR 121 , SCOR 121 , OCSR 121 , COSR 121 , CSOR 121 , hydroxyl group, nitro group, CN, halogen atom, or COOR 121 may be substituted, R 104 , R 105 , R 106 and R
- photoradical polymerization initiators (D) include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis (cyclopentadienyl) -bis [2,6-difluoro-3- (py-1-yl) )] Titanium and the like.
- photo radical polymerization initiators (D) can be used alone or in combination of two or more according to the desired performance.
- the radical photopolymerization initiator (D) as described above is preferably 0.01 to 10% by mass, particularly preferably 0.1 to 1% by mass in the photosensitive composition of the present invention.
- the content of the photo radical polymerization initiator is less than 0.01% by mass, curing by exposure may be insufficient.
- the photo radical polymerization initiator is contained in the photosensitive composition. It may precipitate.
- a coloring agent may be further added to the photosensitive composition to obtain a colored photosensitive composition.
- the cured product of the colored photosensitive composition is suitably used as a color filter.
- the addition amount of the colorant is preferably 0.01 to 50% by mass, and more preferably 0.1 to 30% by mass. When the addition amount of the colorant is less than 0.01% by mass, the color is insufficient, and when it is greater than 50% by mass, the colorant may precipitate in the photosensitive composition.
- the colorant examples include dyes and pigments.
- the dye is not particularly limited as long as it is a compound having absorption at 380 to 1200 nm.
- inorganic pigments or organic pigments can be used.
- inorganic pigment or organic pigment commercially available pigments can also be used.
- the water resistance and heat resistance can be improved by adding a crosslinking agent to the photosensitive composition of the present invention and reacting with the hydrophilic group of the polymer.
- the crosslinking agent include polyoxazoline compounds, carbodiimide compounds, epoxy compounds, polyamines, polyols, dicyandiamide derivatives, hydrazine compounds, polyhydrazide compounds (dihydrazide, trihydrazide), aldehydes, methylol compounds, activated vinyl compounds, poly Isocyanate compounds, alkylene carbonate compounds of phenol compounds, polyvalent metal salts, silane coupling agents, organic titanium, etc.
- polyoxazoline compounds and carbodiimide compounds react at a heat drying temperature of 100 to 120 ° C. preferable.
- cross-linking agent Commercially available products may be used as the cross-linking agent.
- Epocros WS-300, WS-500, WS-700 manufactured by Nippon Shokubai Co., Ltd.
- Carbodilite V-02, V-02-L2, SV-02, And V-04, V-10, SW-12G, E-02, E-03A, E-05 manufactured by Nisshinbo.
- a solvent can be added to the photosensitive composition and the colored photosensitive composition.
- the solvent is usually a solvent that can dissolve or disperse each of the above components as necessary, for example, methyl ethyl ketone, methyl amyl ketone, diethyl ketone, acetone, methyl isopropyl ketone, methyl isobutyl ketone, cyclohexanone, 2-heptanone, etc.
- Ketones such as ethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, dipropylene glycol dimethyl ether; methyl acetate, ethyl acetate, acetic acid-n-propyl, isopropyl acetate Ester solvents such as n-butyl acetate, cyclohexyl acetate, ethyl lactate, dimethyl succinate, and texanol; cellosolv solvents such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether; methanol Alcohol solvents such as ethanol, iso- or n-propanol, iso- or n-butanol, amyl alcohol, diacetone alcohol; ethylene glycol monomethyl acetate, ethylene glycol monoethyl acetate, propylene glycol-1-monomethyl ether-2-a
- ketones, ether ester solvents, etc. particularly propylene glycol-1-monomethyl ether-2-acetate, cyclohexanone, and the like are preferable because the compatibility of the resist and the radical photopolymerization initiator is good in the photosensitive composition.
- the above-mentioned colored photosensitive composition can further contain an inorganic compound.
- the inorganic compound include metal oxides such as nickel oxide, iron oxide, iridium oxide, titanium oxide, zinc oxide, magnesium oxide, calcium oxide, potassium oxide, silica, and alumina; lamellar clay mineral, miloli blue, calcium carbonate, Magnesium carbonate, cobalt, manganese, glass powder, mica, talc, kaolin, ferrocyanide, various metal sulfates, sulfides, selenides, aluminum silicate, calcium silicate, aluminum hydroxide, platinum, gold, silver, copper Etc.
- a dispersant can be added.
- any colorant or inorganic compound can be used as long as it can disperse and stabilize, and commercially available dispersants such as BYK series manufactured by BYK Chemie can be used, and polyester having a basic functional group, Polymer dispersant made of polyether, polyurethane, having a nitrogen atom as a basic functional group, the functional group having a nitrogen atom is an amine and / or a quaternary salt thereof, and an amine value of 1 to 100 mgKOH / g Those are preferably used.
- the colored photosensitive composition includes, if necessary, thermal polymerization inhibitors such as p-anisole, hydroquinone, pyrocatechol, t-butylcatechol, phenothiazine; plasticizer; adhesion promoter; filler; Agents; leveling agents; surface conditioning agents; antioxidants such as phenolic antioxidants, phosphite antioxidants, thioether antioxidants; UV absorbers; dispersion aids; aggregation inhibitors; catalysts; Conventional additives such as thickeners can be added.
- thermal polymerization inhibitors such as p-anisole, hydroquinone, pyrocatechol, t-butylcatechol, phenothiazine
- plasticizer adhesion promoter
- filler Agents; leveling agents; surface conditioning agents; antioxidants such as phenolic antioxidants, phosphite antioxidants, thioether antioxidants; UV absorbers; dispersion aids; aggregation inhibitors; catalysts; Conventional additives such as
- the properties of the cured product of the colored photosensitive composition of the present invention can be improved.
- 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, phenolic resin, phenoxy resin, polyamideimide resin, polyamic acid resin, epoxy resin, and the like.
- polystyrene, (meth) acrylic acid-methyl methacrylate copolymer, and epoxy resin are included. Masui.
- a chain transfer agent a sensitizer, a surfactant, a silane coupling agent, melamine and the like can be used in combination with the colored photosensitive composition.
- a sulfur atom-containing compound is generally used.
- Alkyl compounds trimethylolpropane tris (3-mercaptoisobutyrate), butanediol bis (3-mercaptoisobutyrate), hexanedithiol, decanedithiol, 1,4- Methyl mercaptobenzene, butanediol bisthiopropionate, butanediol bisthioglycolate, ethylene glycol bisthioglycolate, trimethylolpropane tristhioglycolate, butanediol bisthiopropionate, trimethylolpropane tristhiopropionate , Trimethylolpropane tristhioglycolate, pentaerythritol tetrakisthiopropionate, pentaerythritol tetrakisthioglycolate, trishydroxyethyl tristhiopropionate, the following compound no. C1, aliphatic polyfunctional thiol
- the surfactant examples include fluorine surfactants such as perfluoroalkyl phosphates and perfluoroalkyl carboxylates, anionic surfactants such as higher fatty acid alkali salts, alkyl sulfonates, and alkyl sulfates, and higher amines. Cationic surfactants such as halogenates and quaternary ammonium salts, nonionic surfactants such as polyethylene glycol alkyl ethers, polyethylene glycol fatty acid esters, sorbitan fatty acid esters and fatty acid monoglycerides, amphoteric surfactants, silicone surfactants Surfactants such as agents can be used, and these may be used in combination.
- fluorine surfactants such as perfluoroalkyl phosphates and perfluoroalkyl carboxylates
- anionic surfactants such as higher fatty acid alkali salts, alkyl sulfonates, and alkyl sulfates,
- silane coupling agent for example, a silane coupling agent manufactured by Shin-Etsu Chemical Co., Ltd. can be used. Among them, KBE-9007, KBM-502, KBE-403 and the like, silane cups having an isocyanate group, a methacryloyl group, and an epoxy group. A ring agent is preferably used.
- Examples of the melamine compound include all or part of active methylol groups (CH 2 OH groups) in nitrogen compounds such as (poly) methylol melamine, (poly) methylol glycoluril, (poly) methylol benzoguanamine, and (poly) methylol urea. Mention may be made of compounds in which (at least two) are alkyl etherified.
- examples of the alkyl group constituting the alkyl ether include a methyl group, an ethyl group, and a butyl group, which may be the same as or different from each other.
- methylol groups that are not alkyletherified may be self-condensed within one molecule, and may be condensed between two molecules, resulting in the formation of an oligomer component.
- hexamethoxymethyl melamine, hexabutoxymethyl melamine, tetramethoxymethyl glycoluril, tetrabutoxymethyl glycoluril and the like can be used.
- alkyl etherified melamines such as hexamethoxymethyl melamine and hexabutoxymethyl melamine are preferable.
- the photosensitive composition and the colored photosensitive composition are prepared by known means such as spin coater, roll coater, bar coater, die coater, curtain coater, various printing, dipping, soda glass, quartz glass, semiconductor substrate, metal. It can be applied on a supporting substrate such as paper or plastic. Moreover, after once applying on support bases, such as a film, it can also transfer on another support base
- the active energy ray light source used for curing the photosensitive composition and the colored photosensitive composition those that emit light having a wavelength of 300 to 450 nm can be used.
- Mercury vapor arc, carbon arc, xenon arc, etc. can be used.
- the laser direct drawing method that directly forms an image from digital information such as a computer without using a mask improves not only productivity but also resolution and positional accuracy.
- the laser beam light having a wavelength of 340 to 430 nm is preferably used, but an argon ion laser, a helium neon laser, a YAG laser, a semiconductor laser, etc. are visible to infrared region. Those that emit light are also used. When these lasers are used, a sensitizing dye that absorbs the region from visible to infrared is added.
- the photosensitive composition and the colored photosensitive composition of the present invention can also be patterned through a double patterning process in which patterning is performed twice using two photosensitive compositions or colored photosensitive compositions.
- the photosensitive composition and the colored photosensitive composition of the present invention can be temporarily cured by irradiating the active energy ray and further cured by heating.
- the pattern can be formed by heating after irradiating the active energy ray, developing, and heating.
- the photosensitive composition and the colored photosensitive composition are photocurable paints or varnishes, photocurable adhesives, printed boards, color televisions, PC monitors, portable information terminals, digital cameras, etc.
- the photosensitive composition of the present invention can be used for a transparent conductive film, a reflective film, a polarizing plate, a protective film, etc., and is applied through a mask having a predetermined pattern shape by sequentially applying each of the above-described layers to a transparent substrate. It can be used as a transparent laminate obtained by irradiating light, developing the exposed film with a developer, and heating the developed film.
- a transparent base material in which transparent thin film layers and metal thin film layers made of a composite oxide of indium oxide and cerium oxide are alternately arranged can be used.
- a photosensitive composition containing the compound of the present invention as a latent additive may be used for each of the aforementioned layers, or the photosensitive composition may be used for any one or more layers.
- the transparent laminate is suitably used for a display device.
- the colored photosensitive composition is used for the purpose of forming pixels of a color filter, and is particularly useful as a photosensitive composition for forming a color filter for a display device for an image display device such as a liquid crystal display panel.
- the color filter for a display device includes (1) a step of forming a coating film of the colored photosensitive composition on a substrate, and (2) irradiating the coating film with active light through a mask having a predetermined pattern shape. It is preferably formed by a step, (3) a step of developing the film after exposure with a developer, and (4) a step of heating the film after development.
- the colored photosensitive composition of the present invention is also useful as an inkjet colored photosensitive composition having no development step.
- a multi-tone mask such as a halftone mask or a gray scale mask can be used.
- reaction solution was cooled to room temperature, 160 g of PGMEA, 59 g of biphthalic anhydride and 0.24 g of tetra-n-butylammonium bromide were added, and the mixture was stirred at 120 ° C. for 4 hours. Further, 20 g of tetrahydrophthalic anhydride was added, and after stirring at 120 ° C. for 4 hours, at 100 ° C. for 3 hours, at 80 ° C. for 4 hours, at 60 ° C. for 6 hours, and at 40 ° C.
- Photosensitive composition No. 1-No. 11 and comparative photosensitive composition no. 1-No. Preparation of photosensitive composition No. 2 in accordance with the formulation of [Table 1] and [Table 2].
- 1-No. 11 and comparative photosensitive composition no. 1-No. 2 was prepared. The numerical values in [Table 1] and [Table 2] are parts by mass.
- A-1 to A-4 in [Table 1] and [Table 2] represent the following latent additives.
- B-1 to B-4, B'-1, C-1 to C-2, D-1 to D-3, E-1 and F-1 in [Table 1] and [Table 2] are respectively The following compounds are represented.
- B-1 SPC-1000 (Acrylic resin from Showa Denko; weight average molecular weight 31980, double bond equivalent 900)
- B-2 SPC-3000 (Acrylic resin from Showa Denko; weight average molecular weight 7610, double bond equivalent 340)
- B-3 Obtained in Production Example 1 (weight average molecular weight 22000, double bond equivalent 330)
- B-4 Obtained in Production Example 2 (weight average molecular weight 5600, double bond equivalent 434)
- B′-1 SPC-2000 Showa Denko acryl resin; weight average molecular weight 17500, double bond equivalent 0)
- C-1 Aronix M450 (Toagosei Co., Ltd.
- the photosensitive composition of the present invention is maintained with high transparency after firing, that is, it has high heat resistance and excellent solvent resistance.
- the photosensitive composition which gives the hardened
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Abstract
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WO2020230732A1 (fr) * | 2019-05-15 | 2020-11-19 | 株式会社Adeka | Composition, produit durci, procédé de production de produit durci et additif |
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JPWO2017170465A1 (ja) | 2019-02-07 |
KR20180123003A (ko) | 2018-11-14 |
JP6849659B2 (ja) | 2021-03-24 |
KR102369445B1 (ko) | 2022-03-03 |
CN108473611A (zh) | 2018-08-31 |
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