WO2022181563A1 - 光硬化性液状組成物、硬化物、及び硬化物の製造方法 - Google Patents
光硬化性液状組成物、硬化物、及び硬化物の製造方法 Download PDFInfo
- Publication number
- WO2022181563A1 WO2022181563A1 PCT/JP2022/007038 JP2022007038W WO2022181563A1 WO 2022181563 A1 WO2022181563 A1 WO 2022181563A1 JP 2022007038 W JP2022007038 W JP 2022007038W WO 2022181563 A1 WO2022181563 A1 WO 2022181563A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- liquid composition
- photocurable liquid
- formula
- groups
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 136
- 239000007788 liquid Substances 0.000 title claims abstract description 128
- 238000004519 manufacturing process Methods 0.000 title abstract description 7
- -1 nitrogen-containing compound Chemical class 0.000 claims abstract description 356
- 229910044991 metal oxide Inorganic materials 0.000 claims abstract description 69
- 150000004706 metal oxides Chemical class 0.000 claims abstract description 69
- 239000000178 monomer Substances 0.000 claims abstract description 66
- 239000002105 nanoparticle Substances 0.000 claims abstract description 66
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- 239000003999 initiator Substances 0.000 claims abstract description 21
- 150000002466 imines Chemical class 0.000 claims abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 117
- 125000000217 alkyl group Chemical group 0.000 claims description 101
- 125000000962 organic group Chemical group 0.000 claims description 85
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 78
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 67
- 125000003118 aryl group Chemical group 0.000 claims description 47
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 41
- 125000005843 halogen group Chemical group 0.000 claims description 36
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- 229910052717 sulfur Inorganic materials 0.000 claims description 21
- 125000002947 alkylene group Chemical group 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 6
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 6
- 238000000465 moulding Methods 0.000 claims description 5
- 150000007824 aliphatic compounds Chemical class 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 claims description 2
- 230000004807 localization Effects 0.000 abstract description 14
- 125000001424 substituent group Chemical group 0.000 description 87
- 125000000623 heterocyclic group Chemical group 0.000 description 50
- 239000000047 product Substances 0.000 description 49
- 125000003545 alkoxy group Chemical group 0.000 description 46
- 125000001931 aliphatic group Chemical group 0.000 description 29
- 238000000034 method Methods 0.000 description 26
- 125000001624 naphthyl group Chemical group 0.000 description 24
- 239000002904 solvent Substances 0.000 description 23
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 21
- 125000000753 cycloalkyl group Chemical group 0.000 description 21
- 125000002252 acyl group Chemical group 0.000 description 20
- 239000002245 particle Substances 0.000 description 19
- 239000003795 chemical substances by application Substances 0.000 description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 15
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 14
- 150000001721 carbon Chemical group 0.000 description 13
- 229910052799 carbon Inorganic materials 0.000 description 13
- 125000004122 cyclic group Chemical group 0.000 description 13
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 13
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 12
- 229910052731 fluorine Inorganic materials 0.000 description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 12
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 12
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 11
- 125000001326 naphthylalkyl group Chemical group 0.000 description 11
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 11
- 125000003884 phenylalkyl group Chemical group 0.000 description 11
- 239000004014 plasticizer Substances 0.000 description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- 229910052801 chlorine Inorganic materials 0.000 description 10
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 10
- 125000001153 fluoro group Chemical group F* 0.000 description 10
- 229910052760 oxygen Inorganic materials 0.000 description 10
- 229910001928 zirconium oxide Inorganic materials 0.000 description 10
- 125000001309 chloro group Chemical group Cl* 0.000 description 9
- 125000004093 cyano group Chemical group *C#N 0.000 description 9
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 9
- 125000002950 monocyclic group Chemical group 0.000 description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 9
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 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 8
- 230000001771 impaired effect Effects 0.000 description 8
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 8
- 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 8
- 229910052710 silicon Inorganic materials 0.000 description 8
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 125000004423 acyloxy group Chemical group 0.000 description 7
- 229910052796 boron Inorganic materials 0.000 description 7
- GPTXWRGISTZRIO-UHFFFAOYSA-N chlorquinaldol Chemical compound ClC1=CC(Cl)=C(O)C2=NC(C)=CC=C21 GPTXWRGISTZRIO-UHFFFAOYSA-N 0.000 description 7
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 235000011187 glycerol Nutrition 0.000 description 7
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 7
- 229910052698 phosphorus Inorganic materials 0.000 description 7
- 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 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-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
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 6
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 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 6
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 5
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical group CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 5
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 238000001723 curing Methods 0.000 description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 4
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000005322 morpholin-1-yl group Chemical group 0.000 description 4
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 125000005359 phenoxyalkyl group Chemical group 0.000 description 4
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 4
- 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 4
- 238000002834 transmittance Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 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 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical group C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 3
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical group C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000003107 substituted aryl group Chemical group 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 2
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- ASUQXIDYMVXFKU-UHFFFAOYSA-N 2,6-dibromo-9,9-dimethylfluorene Chemical compound C1=C(Br)C=C2C(C)(C)C3=CC=C(Br)C=C3C2=C1 ASUQXIDYMVXFKU-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
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 2
- 125000005999 2-bromoethyl group Chemical group 0.000 description 2
- DZZAHLOABNWIFA-UHFFFAOYSA-N 2-butoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCCCC)C(=O)C1=CC=CC=C1 DZZAHLOABNWIFA-UHFFFAOYSA-N 0.000 description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 2
- FLFWJIBUZQARMD-UHFFFAOYSA-N 2-mercapto-1,3-benzoxazole Chemical compound C1=CC=C2OC(S)=NC2=C1 FLFWJIBUZQARMD-UHFFFAOYSA-N 0.000 description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- FFOPEPMHKILNIT-UHFFFAOYSA-N Isopropyl butyrate Chemical compound CCCC(=O)OC(C)C FFOPEPMHKILNIT-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- XUPYJHCZDLZNFP-UHFFFAOYSA-N butyl butanoate Chemical compound CCCCOC(=O)CCC XUPYJHCZDLZNFP-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 2
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
- 125000005921 isopentoxy group Chemical group 0.000 description 2
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000000691 measurement method Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- LPEKGGXMPWTOCB-UHFFFAOYSA-N methyl 2-hydroxypropionate Chemical compound COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 2
- 239000011859 microparticle Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- MXHTZQSKTCCMFG-UHFFFAOYSA-N n,n-dibenzyl-1-phenylmethanamine Chemical compound C=1C=CC=CC=1CN(CC=1C=CC=CC=1)CC1=CC=CC=C1 MXHTZQSKTCCMFG-UHFFFAOYSA-N 0.000 description 2
- MIYKHJXFICMPOJ-UHFFFAOYSA-N n-benzyl-1-phenylmethanimine Chemical compound C=1C=CC=CC=1CN=CC1=CC=CC=C1 MIYKHJXFICMPOJ-UHFFFAOYSA-N 0.000 description 2
- 125000006610 n-decyloxy group Chemical group 0.000 description 2
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
- DYFFAVRFJWYYQO-UHFFFAOYSA-N n-methyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(C)C1=CC=CC=C1 DYFFAVRFJWYYQO-UHFFFAOYSA-N 0.000 description 2
- 125000006609 n-nonyloxy group Chemical group 0.000 description 2
- 125000006608 n-octyloxy group Chemical group 0.000 description 2
- 239000002159 nanocrystal Substances 0.000 description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 2
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 2
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 2
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 2
- 229920000193 polymethacrylate Polymers 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 125000005922 tert-pentoxy group Chemical group 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 125000005369 trialkoxysilyl group Chemical group 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- VMHYWKBKHMYRNF-UHFFFAOYSA-N (2-chlorophenyl)-phenylmethanone Chemical compound ClC1=CC=CC=C1C(=O)C1=CC=CC=C1 VMHYWKBKHMYRNF-UHFFFAOYSA-N 0.000 description 1
- RYNQKSJRFHJZTK-UHFFFAOYSA-N (3-methoxy-3-methylbutyl) acetate Chemical compound COC(C)(C)CCOC(C)=O RYNQKSJRFHJZTK-UHFFFAOYSA-N 0.000 description 1
- OWSKJORLRSWYGK-UHFFFAOYSA-N (3-methoxy-3-methylbutyl) propanoate Chemical compound CCC(=O)OCCC(C)(C)OC OWSKJORLRSWYGK-UHFFFAOYSA-N 0.000 description 1
- KFJJYOKMAAQFHC-UHFFFAOYSA-N (4-methoxy-5,5-dimethylcyclohexa-1,3-dien-1-yl)-phenylmethanone Chemical compound C1C(C)(C)C(OC)=CC=C1C(=O)C1=CC=CC=C1 KFJJYOKMAAQFHC-UHFFFAOYSA-N 0.000 description 1
- XHXSXTIIDBZEKB-UHFFFAOYSA-N 1,2,3,4,5,6,7,8-octamethylanthracene-9,10-dione Chemical compound CC1=C(C)C(C)=C2C(=O)C3=C(C)C(C)=C(C)C(C)=C3C(=O)C2=C1C XHXSXTIIDBZEKB-UHFFFAOYSA-N 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- WPMSGYCSSLALHQ-UHFFFAOYSA-N 1,3,5-trichloro-2-methyl-1,3,5-triazinane Chemical compound CC1N(Cl)CN(Cl)CN1Cl WPMSGYCSSLALHQ-UHFFFAOYSA-N 0.000 description 1
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 1
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 1
- QWOZZTWBWQMEPD-UHFFFAOYSA-N 1-(2-ethoxypropoxy)propan-2-ol Chemical compound CCOC(C)COCC(C)O QWOZZTWBWQMEPD-UHFFFAOYSA-N 0.000 description 1
- MLKIVXXYTZKNMI-UHFFFAOYSA-N 1-(4-dodecylphenyl)-2-hydroxy-2-methylpropan-1-one Chemical compound CCCCCCCCCCCCC1=CC=C(C(=O)C(C)(C)O)C=C1 MLKIVXXYTZKNMI-UHFFFAOYSA-N 0.000 description 1
- IMDHDEPPVWETOI-UHFFFAOYSA-N 1-(4-tert-butylphenyl)-2,2,2-trichloroethanone Chemical compound CC(C)(C)C1=CC=C(C(=O)C(Cl)(Cl)Cl)C=C1 IMDHDEPPVWETOI-UHFFFAOYSA-N 0.000 description 1
- VMCRQYHCDSXNLW-UHFFFAOYSA-N 1-(4-tert-butylphenyl)-2,2-dichloroethanone Chemical compound CC(C)(C)C1=CC=C(C(=O)C(Cl)Cl)C=C1 VMCRQYHCDSXNLW-UHFFFAOYSA-N 0.000 description 1
- UYFJYGWNYQCHOB-UHFFFAOYSA-N 1-(4-tert-butylphenyl)ethanone Chemical compound CC(=O)C1=CC=C(C(C)(C)C)C=C1 UYFJYGWNYQCHOB-UHFFFAOYSA-N 0.000 description 1
- FYBFGAFWCBMEDG-UHFFFAOYSA-N 1-[3,5-di(prop-2-enoyl)-1,3,5-triazinan-1-yl]prop-2-en-1-one Chemical compound C=CC(=O)N1CN(C(=O)C=C)CN(C(=O)C=C)C1 FYBFGAFWCBMEDG-UHFFFAOYSA-N 0.000 description 1
- HUDYANRNMZDQGA-UHFFFAOYSA-N 1-[4-(dimethylamino)phenyl]ethanone Chemical compound CN(C)C1=CC=C(C(C)=O)C=C1 HUDYANRNMZDQGA-UHFFFAOYSA-N 0.000 description 1
- ONCICIKBSHQJTB-UHFFFAOYSA-N 1-[4-(dimethylamino)phenyl]propan-1-one Chemical compound CCC(=O)C1=CC=C(N(C)C)C=C1 ONCICIKBSHQJTB-UHFFFAOYSA-N 0.000 description 1
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 1
- VKQJCUYEEABXNK-UHFFFAOYSA-N 1-chloro-4-propoxythioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C(OCCC)=CC=C2Cl VKQJCUYEEABXNK-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- CNJRPYFBORAQAU-UHFFFAOYSA-N 1-ethoxy-2-(2-methoxyethoxy)ethane Chemical compound CCOCCOCCOC CNJRPYFBORAQAU-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- FENFUOGYJVOCRY-UHFFFAOYSA-N 1-propoxypropan-2-ol Chemical compound CCCOCC(C)O FENFUOGYJVOCRY-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- OAMHTTBNEJBIKA-UHFFFAOYSA-N 2,2,2-trichloro-1-phenylethanone Chemical compound ClC(Cl)(Cl)C(=O)C1=CC=CC=C1 OAMHTTBNEJBIKA-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- CERJZAHSUZVMCH-UHFFFAOYSA-N 2,2-dichloro-1-phenylethanone Chemical compound ClC(Cl)C(=O)C1=CC=CC=C1 CERJZAHSUZVMCH-UHFFFAOYSA-N 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- PUGOMSLRUSTQGV-UHFFFAOYSA-N 2,3-di(prop-2-enoyloxy)propyl prop-2-enoate Chemical compound C=CC(=O)OCC(OC(=O)C=C)COC(=O)C=C PUGOMSLRUSTQGV-UHFFFAOYSA-N 0.000 description 1
- LZWVPGJPVCYAOC-UHFFFAOYSA-N 2,3-diphenylanthracene-9,10-dione Chemical compound C=1C=CC=CC=1C=1C=C2C(=O)C3=CC=CC=C3C(=O)C2=CC=1C1=CC=CC=C1 LZWVPGJPVCYAOC-UHFFFAOYSA-N 0.000 description 1
- DXUMYHZTYVPBEZ-UHFFFAOYSA-N 2,4,6-tris(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 DXUMYHZTYVPBEZ-UHFFFAOYSA-N 0.000 description 1
- MFUCEQWAFQMGOR-UHFFFAOYSA-N 2,4-diethyl-9h-thioxanthene Chemical compound C1=CC=C2CC3=CC(CC)=CC(CC)=C3SC2=C1 MFUCEQWAFQMGOR-UHFFFAOYSA-N 0.000 description 1
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 1
- LCHAFMWSFCONOO-UHFFFAOYSA-N 2,4-dimethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC(C)=C3SC2=C1 LCHAFMWSFCONOO-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- WMDZKDKPYCNCDZ-UHFFFAOYSA-N 2-(2-butoxypropoxy)propan-1-ol Chemical compound CCCCOC(C)COC(C)CO WMDZKDKPYCNCDZ-UHFFFAOYSA-N 0.000 description 1
- 125000003070 2-(2-chlorophenyl)ethyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- BJINVQNEBGOMCR-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethyl acetate Chemical compound COCCOCCOC(C)=O BJINVQNEBGOMCR-UHFFFAOYSA-N 0.000 description 1
- AMOYMEBHYUTMKJ-UHFFFAOYSA-N 2-(2-phenylethoxy)ethylbenzene Chemical compound C=1C=CC=CC=1CCOCCC1=CC=CC=C1 AMOYMEBHYUTMKJ-UHFFFAOYSA-N 0.000 description 1
- WJBDTRSHWOPBAZ-UHFFFAOYSA-N 2-(2-phenylethylsulfanyl)ethylbenzene Chemical compound C=1C=CC=CC=1CCSCCC1=CC=CC=C1 WJBDTRSHWOPBAZ-UHFFFAOYSA-N 0.000 description 1
- DJCYDDALXPHSHR-UHFFFAOYSA-N 2-(2-propoxyethoxy)ethanol Chemical compound CCCOCCOCCO DJCYDDALXPHSHR-UHFFFAOYSA-N 0.000 description 1
- XYVAYAJYLWYJJN-UHFFFAOYSA-N 2-(2-propoxypropoxy)propan-1-ol Chemical compound CCCOC(C)COC(C)CO XYVAYAJYLWYJJN-UHFFFAOYSA-N 0.000 description 1
- 125000000301 2-(3-chlorophenyl)ethyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- QRHHZFRCJDAUNA-UHFFFAOYSA-N 2-(4-methoxyphenyl)-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound C1=CC(OC)=CC=C1C1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 QRHHZFRCJDAUNA-UHFFFAOYSA-N 0.000 description 1
- KJSGODDTWRXQRH-UHFFFAOYSA-N 2-(dimethylamino)ethyl benzoate Chemical compound CN(C)CCOC(=O)C1=CC=CC=C1 KJSGODDTWRXQRH-UHFFFAOYSA-N 0.000 description 1
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 description 1
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- WFSMVVDJSNMRAR-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethoxy]ethanol Chemical compound CCOCCOCCOCCO WFSMVVDJSNMRAR-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- WAEVWDZKMBQDEJ-UHFFFAOYSA-N 2-[2-(2-methoxypropoxy)propoxy]propan-1-ol Chemical compound COC(C)COC(C)COC(C)CO WAEVWDZKMBQDEJ-UHFFFAOYSA-N 0.000 description 1
- ZJRNXDIVAGHETA-UHFFFAOYSA-N 2-[2-(3,4-dimethoxyphenyl)ethenyl]-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound C1=C(OC)C(OC)=CC=C1C=CC1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 ZJRNXDIVAGHETA-UHFFFAOYSA-N 0.000 description 1
- BLLZAHSARJPHSO-UHFFFAOYSA-N 2-[2-(4-ethoxyphenyl)ethenyl]-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound C1=CC(OCC)=CC=C1C=CC1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 BLLZAHSARJPHSO-UHFFFAOYSA-N 0.000 description 1
- XOPKKHCDIAYUSK-UHFFFAOYSA-N 2-[2-(5-methylfuran-2-yl)ethenyl]-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound O1C(C)=CC=C1C=CC1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 XOPKKHCDIAYUSK-UHFFFAOYSA-N 0.000 description 1
- PNDRGJCVJPHPOZ-UHFFFAOYSA-N 2-[2-(furan-2-yl)ethenyl]-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC(C(Cl)(Cl)Cl)=NC(C=CC=2OC=CC=2)=N1 PNDRGJCVJPHPOZ-UHFFFAOYSA-N 0.000 description 1
- SEFYJVFBMNOLBK-UHFFFAOYSA-N 2-[2-[2-(oxiran-2-ylmethoxy)ethoxy]ethoxymethyl]oxirane Chemical compound C1OC1COCCOCCOCC1CO1 SEFYJVFBMNOLBK-UHFFFAOYSA-N 0.000 description 1
- LQXYAONREUURJF-UHFFFAOYSA-N 2-[4-(dimethylamino)-2-ethylhexyl]benzoic acid Chemical compound CCC(N(C)C)CC(CC)CC1=CC=CC=C1C(O)=O LQXYAONREUURJF-UHFFFAOYSA-N 0.000 description 1
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- HRJYGQAACVZSEO-UHFFFAOYSA-N 2-chloro-9h-thioxanthene Chemical compound C1=CC=C2CC3=CC(Cl)=CC=C3SC2=C1 HRJYGQAACVZSEO-UHFFFAOYSA-N 0.000 description 1
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- SURWYRGVICLUBJ-UHFFFAOYSA-N 2-ethyl-9,10-dimethoxyanthracene Chemical compound C1=CC=CC2=C(OC)C3=CC(CC)=CC=C3C(OC)=C21 SURWYRGVICLUBJ-UHFFFAOYSA-N 0.000 description 1
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 description 1
- QPXVRLXJHPTCPW-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-(4-propan-2-ylphenyl)propan-1-one Chemical compound CC(C)C1=CC=C(C(=O)C(C)(C)O)C=C1 QPXVRLXJHPTCPW-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 1
- LETDRANQSOEVCX-UHFFFAOYSA-N 2-methyl-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound CC1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 LETDRANQSOEVCX-UHFFFAOYSA-N 0.000 description 1
- ATTLFLQPHSUNBK-UHFFFAOYSA-N 2-methyl-9h-thioxanthene Chemical compound C1=CC=C2CC3=CC(C)=CC=C3SC2=C1 ATTLFLQPHSUNBK-UHFFFAOYSA-N 0.000 description 1
- MYISVPVWAQRUTL-UHFFFAOYSA-N 2-methylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3SC2=C1 MYISVPVWAQRUTL-UHFFFAOYSA-N 0.000 description 1
- HPSGLFKWHYAKSF-UHFFFAOYSA-N 2-phenylethyl prop-2-enoate Chemical compound C=CC(=O)OCCC1=CC=CC=C1 HPSGLFKWHYAKSF-UHFFFAOYSA-N 0.000 description 1
- GCYHRYNSUGLLMA-UHFFFAOYSA-N 2-prop-2-enoxyethanol Chemical compound OCCOCC=C GCYHRYNSUGLLMA-UHFFFAOYSA-N 0.000 description 1
- BQKZEKVKJUIRGH-UHFFFAOYSA-N 2-prop-2-enoxypropan-1-ol Chemical compound OCC(C)OCC=C BQKZEKVKJUIRGH-UHFFFAOYSA-N 0.000 description 1
- SQAAXANYWPZYJI-UHFFFAOYSA-N 2-propan-2-yl-9h-thioxanthene Chemical compound C1=CC=C2CC3=CC(C(C)C)=CC=C3SC2=C1 SQAAXANYWPZYJI-UHFFFAOYSA-N 0.000 description 1
- KTALPKYXQZGAEG-UHFFFAOYSA-N 2-propan-2-ylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3SC2=C1 KTALPKYXQZGAEG-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 description 1
- NTKBNCABAMQDIG-UHFFFAOYSA-N 3-butoxypropan-1-ol Chemical compound CCCCOCCCO NTKBNCABAMQDIG-UHFFFAOYSA-N 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- DKIDEFUBRARXTE-UHFFFAOYSA-M 3-mercaptopropionate Chemical compound [O-]C(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-M 0.000 description 1
- QMYGFTJCQFEDST-UHFFFAOYSA-N 3-methoxybutyl acetate Chemical compound COC(C)CCOC(C)=O QMYGFTJCQFEDST-UHFFFAOYSA-N 0.000 description 1
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 description 1
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 1
- URDOJQUSEUXVRP-UHFFFAOYSA-N 3-triethoxysilylpropyl 2-methylprop-2-enoate Chemical group CCO[Si](OCC)(OCC)CCCOC(=O)C(C)=C URDOJQUSEUXVRP-UHFFFAOYSA-N 0.000 description 1
- KBQVDAIIQCXKPI-UHFFFAOYSA-N 3-trimethoxysilylpropyl prop-2-enoate Chemical group CO[Si](OC)(OC)CCCOC(=O)C=C KBQVDAIIQCXKPI-UHFFFAOYSA-N 0.000 description 1
- 238000010146 3D printing Methods 0.000 description 1
- OKISUZLXOYGIFP-UHFFFAOYSA-N 4,4'-dichlorobenzophenone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=C(Cl)C=C1 OKISUZLXOYGIFP-UHFFFAOYSA-N 0.000 description 1
- SQEGODYTGXKGEV-UHFFFAOYSA-N 4-(dimethylamino)-2-(3-methylbutyl)benzoic acid Chemical compound CC(C)CCC1=CC(N(C)C)=CC=C1C(O)=O SQEGODYTGXKGEV-UHFFFAOYSA-N 0.000 description 1
- YDIYEOMDOWUDTJ-UHFFFAOYSA-N 4-(dimethylamino)benzoic acid Chemical compound CN(C)C1=CC=C(C(O)=O)C=C1 YDIYEOMDOWUDTJ-UHFFFAOYSA-N 0.000 description 1
- BLLOXKZNPPDLGM-UHFFFAOYSA-N 4-[2-[4,6-bis(trichloromethyl)-1,3,5-triazin-2-yl]ethenyl]-n,n-diethyl-3-methylaniline Chemical compound CC1=CC(N(CC)CC)=CC=C1C=CC1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 BLLOXKZNPPDLGM-UHFFFAOYSA-N 0.000 description 1
- LXDXJSHQARTINV-UHFFFAOYSA-N 4-bromoquinoline-6-carboxylic acid Chemical compound N1=CC=C(Br)C2=CC(C(=O)O)=CC=C21 LXDXJSHQARTINV-UHFFFAOYSA-N 0.000 description 1
- PRFAXWWHJWIUPI-UHFFFAOYSA-N 4-methoxytriazine Chemical compound COC1=CC=NN=N1 PRFAXWWHJWIUPI-UHFFFAOYSA-N 0.000 description 1
- BMVWCPGVLSILMU-UHFFFAOYSA-N 5,6-dihydrodibenzo[2,1-b:2',1'-f][7]annulen-11-one Chemical compound C1CC2=CC=CC=C2C(=O)C2=CC=CC=C21 BMVWCPGVLSILMU-UHFFFAOYSA-N 0.000 description 1
- TXGWXGNDXYPWLF-UHFFFAOYSA-N 6-triethoxysilylhex-1-en-3-one Chemical group CCO[Si](OCC)(OCC)CCCC(=O)C=C TXGWXGNDXYPWLF-UHFFFAOYSA-N 0.000 description 1
- FUWFDADDJOUNDL-UHFFFAOYSA-N 9,10-diethoxy-2-ethylanthracene Chemical compound CCC1=CC=C2C(OCC)=C(C=CC=C3)C3=C(OCC)C2=C1 FUWFDADDJOUNDL-UHFFFAOYSA-N 0.000 description 1
- GJNKQJAJXSUJBO-UHFFFAOYSA-N 9,10-diethoxyanthracene Chemical compound C1=CC=C2C(OCC)=C(C=CC=C3)C3=C(OCC)C2=C1 GJNKQJAJXSUJBO-UHFFFAOYSA-N 0.000 description 1
- JWJMBKSFTTXMLL-UHFFFAOYSA-N 9,10-dimethoxyanthracene Chemical compound C1=CC=C2C(OC)=C(C=CC=C3)C3=C(OC)C2=C1 JWJMBKSFTTXMLL-UHFFFAOYSA-N 0.000 description 1
- RXHZPGSSIWOFGS-UHFFFAOYSA-N 9-(3-acridin-9-ylpropyl)acridine Chemical compound C1=CC=C2C(CCCC=3C4=CC=CC=C4N=C4C=CC=CC4=3)=C(C=CC=C3)C3=NC2=C1 RXHZPGSSIWOFGS-UHFFFAOYSA-N 0.000 description 1
- IPRFSEGUKLMSFA-UHFFFAOYSA-N 9-(5-acridin-9-ylpentyl)acridine Chemical compound C1=CC=C2C(CCCCCC=3C4=CC=CC=C4N=C4C=CC=CC4=3)=C(C=CC=C3)C3=NC2=C1 IPRFSEGUKLMSFA-UHFFFAOYSA-N 0.000 description 1
- YDTZWEXADJYOBJ-UHFFFAOYSA-N 9-(7-acridin-9-ylheptyl)acridine Chemical compound C1=CC=C2C(CCCCCCCC=3C4=CC=CC=C4N=C4C=CC=CC4=3)=C(C=CC=C3)C3=NC2=C1 YDTZWEXADJYOBJ-UHFFFAOYSA-N 0.000 description 1
- MTRFEWTWIPAXLG-UHFFFAOYSA-N 9-phenylacridine Chemical compound C1=CC=CC=C1C1=C(C=CC=C2)C2=NC2=CC=CC=C12 MTRFEWTWIPAXLG-UHFFFAOYSA-N 0.000 description 1
- PQJUJGAVDBINPI-UHFFFAOYSA-N 9H-thioxanthene Chemical compound C1=CC=C2CC3=CC=CC=C3SC2=C1 PQJUJGAVDBINPI-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XXRCUYVCPSWGCC-UHFFFAOYSA-N Ethyl pyruvate Chemical compound CCOC(=O)C(C)=O XXRCUYVCPSWGCC-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N Lactic Acid Natural products CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- OFSAUHSCHWRZKM-UHFFFAOYSA-N Padimate A Chemical compound CC(C)CCOC(=O)C1=CC=C(N(C)C)C=C1 OFSAUHSCHWRZKM-UHFFFAOYSA-N 0.000 description 1
- DIQMPQMYFZXDAX-UHFFFAOYSA-N Pentyl formate Chemical compound CCCCCOC=O DIQMPQMYFZXDAX-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- LFOXEOLGJPJZAA-UHFFFAOYSA-N [(2,6-dimethoxybenzoyl)-(2,4,4-trimethylpentyl)phosphoryl]-(2,6-dimethoxyphenyl)methanone Chemical compound COC1=CC=CC(OC)=C1C(=O)P(=O)(CC(C)CC(C)(C)C)C(=O)C1=C(OC)C=CC=C1OC LFOXEOLGJPJZAA-UHFFFAOYSA-N 0.000 description 1
- XWHJQTQOUDOZGR-CMDGGOBGSA-N [(e)-hex-1-enyl]-trimethoxysilane Chemical compound CCCC\C=C\[Si](OC)(OC)OC XWHJQTQOUDOZGR-CMDGGOBGSA-N 0.000 description 1
- BXWJSZFPMIBKFS-UHFFFAOYSA-N [[(9-ethyl-6-nitrocarbazol-3-yl)-[4-(1-methoxypropan-2-yloxy)-2-methylphenyl]methylidene]amino] acetate Chemical compound C1=C2C3=CC([N+]([O-])=O)=CC=C3N(CC)C2=CC=C1C(=NOC(C)=O)C1=CC=C(OC(C)COC)C=C1C BXWJSZFPMIBKFS-UHFFFAOYSA-N 0.000 description 1
- LOCXTTRLSIDGPS-UHFFFAOYSA-N [[1-oxo-1-(4-phenylsulfanylphenyl)octan-2-ylidene]amino] benzoate Chemical compound C=1C=C(SC=2C=CC=CC=2)C=CC=1C(=O)C(CCCCCC)=NOC(=O)C1=CC=CC=C1 LOCXTTRLSIDGPS-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000001124 arachidoyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- JRPBQTZRNDNNOP-UHFFFAOYSA-N barium titanate Chemical compound [Ba+2].[Ba+2].[O-][Ti]([O-])([O-])[O-] JRPBQTZRNDNNOP-UHFFFAOYSA-N 0.000 description 1
- 229910002113 barium titanate Inorganic materials 0.000 description 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- LHMRXAIRPKSGDE-UHFFFAOYSA-N benzo[a]anthracene-7,12-dione Chemical compound C1=CC2=CC=CC=C2C2=C1C(=O)C1=CC=CC=C1C2=O LHMRXAIRPKSGDE-UHFFFAOYSA-N 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- LUFPJJNWMYZRQE-UHFFFAOYSA-N benzylsulfanylmethylbenzene Chemical compound C=1C=CC=CC=1CSCC1=CC=CC=C1 LUFPJJNWMYZRQE-UHFFFAOYSA-N 0.000 description 1
- JRPRCOLKIYRSNH-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) benzene-1,2-dicarboxylate Chemical compound C=1C=CC=C(C(=O)OCC2OC2)C=1C(=O)OCC1CO1 JRPRCOLKIYRSNH-UHFFFAOYSA-N 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- VYHBFRJRBHMIQZ-UHFFFAOYSA-N bis[4-(diethylamino)phenyl]methanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1 VYHBFRJRBHMIQZ-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- FOYJYXHISWUSDL-UHFFFAOYSA-N butyl 4-(dimethylamino)benzoate Chemical compound CCCCOC(=O)C1=CC=C(N(C)C)C=C1 FOYJYXHISWUSDL-UHFFFAOYSA-N 0.000 description 1
- BTMVHUNTONAYDX-UHFFFAOYSA-N butyl propionate Chemical compound CCCCOC(=O)CC BTMVHUNTONAYDX-UHFFFAOYSA-N 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229910000420 cerium oxide Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 125000004966 cyanoalkyl group Chemical group 0.000 description 1
- 125000001352 cyclobutyloxy group Chemical group C1(CCC1)O* 0.000 description 1
- 125000003113 cycloheptyloxy group Chemical group C1(CCCCCC1)O* 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004410 cyclooctyloxy group Chemical group C1(CCCCCCC1)O* 0.000 description 1
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 1
- 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 description 1
- 125000003074 decanoyl group Chemical group [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(*)=O 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- CKSRFHWWBKRUKA-UHFFFAOYSA-N ethyl 2-ethoxyacetate Chemical compound CCOCC(=O)OCC CKSRFHWWBKRUKA-UHFFFAOYSA-N 0.000 description 1
- GFUIDHWFLMPAGY-UHFFFAOYSA-N ethyl 2-hydroxy-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)O GFUIDHWFLMPAGY-UHFFFAOYSA-N 0.000 description 1
- ZANNOFHADGWOLI-UHFFFAOYSA-N ethyl 2-hydroxyacetate Chemical compound CCOC(=O)CO ZANNOFHADGWOLI-UHFFFAOYSA-N 0.000 description 1
- FJAKCEHATXBFJT-UHFFFAOYSA-N ethyl 2-oxobutanoate Chemical compound CCOC(=O)C(=O)CC FJAKCEHATXBFJT-UHFFFAOYSA-N 0.000 description 1
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 description 1
- IJUHLFUALMUWOM-UHFFFAOYSA-N ethyl 3-methoxypropanoate Chemical compound CCOC(=O)CCOC IJUHLFUALMUWOM-UHFFFAOYSA-N 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 229940117360 ethyl pyruvate Drugs 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 125000005816 fluoropropyl group Chemical group [H]C([H])(F)C([H])([H])C([H])([H])* 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 125000004997 halocarbonyl group Chemical group 0.000 description 1
- 125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 125000005932 isopentyloxycarbonyl group Chemical group 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 125000000400 lauroyl 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])[H] 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 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
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 125000000628 margaroyl 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])[H] 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000011817 metal compound particle Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- YSGBMDFJWFIEDF-UHFFFAOYSA-N methyl 2-hydroxy-3-methylbutanoate Chemical compound COC(=O)C(O)C(C)C YSGBMDFJWFIEDF-UHFFFAOYSA-N 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- LDTLDBDUBGAEDT-UHFFFAOYSA-N methyl 3-sulfanylpropanoate Chemical compound COC(=O)CCS LDTLDBDUBGAEDT-UHFFFAOYSA-N 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- CWKLZLBVOJRSOM-UHFFFAOYSA-N methyl pyruvate Chemical compound COC(=O)C(C)=O CWKLZLBVOJRSOM-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 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
- 125000001419 myristoyl 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])[H] 0.000 description 1
- GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 description 1
- ISGXOWLMGOPVPB-UHFFFAOYSA-N n,n-dibenzylaniline Chemical compound C=1C=CC=CC=1CN(C=1C=CC=CC=1)CC1=CC=CC=C1 ISGXOWLMGOPVPB-UHFFFAOYSA-N 0.000 description 1
- WBGPDYJIPNTOIB-UHFFFAOYSA-N n,n-dibenzylethanamine Chemical compound C=1C=CC=CC=1CN(CC)CC1=CC=CC=C1 WBGPDYJIPNTOIB-UHFFFAOYSA-N 0.000 description 1
- SLKCGEBEEBTUFE-UHFFFAOYSA-N n-benzyl-1,1-diphenylmethanimine Chemical compound C=1C=CC=CC=1CN=C(C=1C=CC=CC=1)C1=CC=CC=C1 SLKCGEBEEBTUFE-UHFFFAOYSA-N 0.000 description 1
- JATCPLSBWDXCNE-UHFFFAOYSA-N n-benzyl-1-phenylethanimine Chemical compound C=1C=CC=CC=1C(C)=NCC1=CC=CC=C1 JATCPLSBWDXCNE-UHFFFAOYSA-N 0.000 description 1
- HSZCJVZRHXPCIA-UHFFFAOYSA-N n-benzyl-n-ethylaniline Chemical compound C=1C=CC=CC=1N(CC)CC1=CC=CC=C1 HSZCJVZRHXPCIA-UHFFFAOYSA-N 0.000 description 1
- ZWRDBWDXRLPESY-UHFFFAOYSA-N n-benzyl-n-ethylethanamine Chemical compound CCN(CC)CC1=CC=CC=C1 ZWRDBWDXRLPESY-UHFFFAOYSA-N 0.000 description 1
- WYZDCUGWXKHESN-UHFFFAOYSA-N n-benzyl-n-methyl-1-phenylmethanamine Chemical compound C=1C=CC=CC=1CN(C)CC1=CC=CC=C1 WYZDCUGWXKHESN-UHFFFAOYSA-N 0.000 description 1
- LXZGVFCKZRHKMU-UHFFFAOYSA-N n-benzyl-n-methylaniline Chemical compound C=1C=CC=CC=1N(C)CC1=CC=CC=C1 LXZGVFCKZRHKMU-UHFFFAOYSA-N 0.000 description 1
- FKJARBPQBIATJT-UHFFFAOYSA-N n-benzyl-n-phenylaniline Chemical compound C=1C=CC=CC=1CN(C=1C=CC=CC=1)C1=CC=CC=C1 FKJARBPQBIATJT-UHFFFAOYSA-N 0.000 description 1
- URUWNYQVXHOQAM-UHFFFAOYSA-N n-benzylpropan-2-imine Chemical compound CC(C)=NCC1=CC=CC=C1 URUWNYQVXHOQAM-UHFFFAOYSA-N 0.000 description 1
- 125000002004 n-butylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006257 n-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])OC(*)=O 0.000 description 1
- ITMSSZATZARZCA-UHFFFAOYSA-N n-ethyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(CC)C1=CC=CC=C1 ITMSSZATZARZCA-UHFFFAOYSA-N 0.000 description 1
- 125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004888 n-propyl amino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006256 n-propyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC(*)=O 0.000 description 1
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 description 1
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001402 nonanoyl 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])[H] 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 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
- LXTZRIBXKVRLOA-UHFFFAOYSA-N padimate a Chemical compound CCCCCOC(=O)C1=CC=C(N(C)C)C=C1 LXTZRIBXKVRLOA-UHFFFAOYSA-N 0.000 description 1
- 125000001312 palmitoyl 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])[H] 0.000 description 1
- 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 1
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
- ILPVOWZUBFRIAX-UHFFFAOYSA-N propyl 2-oxopropanoate Chemical compound CCCOC(=O)C(C)=O ILPVOWZUBFRIAX-UHFFFAOYSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000021003 saturated fats Nutrition 0.000 description 1
- 125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004528 spin coating Methods 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
- 238000003756 stirring Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005934 tert-pentyloxycarbonyl group Chemical group 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- SDIRFAFFHXXYEL-UHFFFAOYSA-N triethoxy(oct-1-enyl)silane Chemical group CCCCCCC=C[Si](OCC)(OCC)OCC SDIRFAFFHXXYEL-UHFFFAOYSA-N 0.000 description 1
- UMFJXASDGBJDEB-UHFFFAOYSA-N triethoxy(prop-2-enyl)silane Chemical compound CCO[Si](CC=C)(OCC)OCC UMFJXASDGBJDEB-UHFFFAOYSA-N 0.000 description 1
- DVFZJTWMDGYBCD-VAWYXSNFSA-N triethoxy-[(e)-hex-1-enyl]silane Chemical compound CCCC\C=C\[Si](OCC)(OCC)OCC DVFZJTWMDGYBCD-VAWYXSNFSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- ZYMHKOVQDOFPHH-UHFFFAOYSA-N trimethoxy(oct-1-enyl)silane Chemical compound CCCCCCC=C[Si](OC)(OC)OC ZYMHKOVQDOFPHH-UHFFFAOYSA-N 0.000 description 1
- LFRDHGNFBLIJIY-UHFFFAOYSA-N trimethoxy(prop-2-enyl)silane Chemical compound CO[Si](OC)(OC)CC=C LFRDHGNFBLIJIY-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 125000000297 undecanoyl 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])[H] 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/38—Esters containing sulfur
-
- 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
- C08F292/00—Macromolecular compounds obtained by polymerising monomers on to inorganic 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
- C08F122/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
- C08F122/10—Esters
- C08F122/1006—Esters of polyhydric alcohols or polyhydric phenols, e.g. ethylene glycol dimethacrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
-
- 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
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
-
- 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
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
- C08F222/1025—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate of aromatic dialcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/18—Amines; Quaternary ammonium compounds with aromatically bound amino groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K9/00—Use of pretreated ingredients
- C08K9/04—Ingredients treated with organic substances
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
Definitions
- the present invention relates to a photocurable liquid composition, a cured product of the photocurable liquid composition, and a method for producing a cured product using the photocurable liquid composition.
- high refractive index materials have been used to form optical members.
- Compositions in which metal oxide particles such as titanium oxide and zirconium oxide are dispersed in an organic component are used as high refractive materials.
- As a composition for forming such a high refractive material an energy ray containing a metal oxide (A) having a specific particle size, a (meth)acrylate (B), and a photopolymerization initiator (C)
- a curable composition has been proposed (see Patent Document 1).
- the present invention has been made in view of the above problems, and provides a photocurable liquid composition capable of forming a cured product in which localization of metal oxide nanoparticles is suppressed, and the photocurable liquid composition. and a method for producing a cured product using the photocurable liquid composition.
- the present inventors added a photocurable liquid composition containing a photopolymerizable monomer (A), metal oxide nanoparticles (B), and a photopolymerization initiator (C) as a nitrogen-containing compound (D) , an amine compound (D1) having a specific structure, and an imine compound (D2) having a specific structure, and found that the above-mentioned problems can be solved by containing at least one selected from the group consisting of, and completed the present invention. reached. More specifically, the present invention provides the following.
- a first aspect of the present invention is a photocurable liquid comprising a photopolymerizable monomer (A), metal oxide nanoparticles (B), a photopolymerization initiator (C), and a nitrogen-containing compound (D)
- a composition comprising: The photopolymerizable monomer (A) has an ethylenically unsaturated double bond,
- a photocurable liquid composition which is at least one selected from the group consisting
- a second aspect of the present invention is a cured product of the photocurable liquid composition according to the first aspect.
- a third aspect of the present invention is to mold the photocurable liquid composition according to the first aspect; and exposing a molded photocurable liquid composition to light.
- a photocurable liquid composition capable of forming a cured product in which localization of metal oxide nanoparticles is suppressed, a cured product of the photocurable liquid composition, and the photocurable and a method for producing a cured product using the liquid composition.
- the photocurable liquid composition contains a photopolymerizable monomer (A), metal oxide nanoparticles (B), a photopolymerization initiator (C), and a nitrogen-containing compound (D).
- a photopolymerizable monomer (A) has an ethylenically unsaturated double bond.
- (meth)acrylate means both acrylate and methacrylate.
- (meth)acrylic means both acrylic and methacrylic.
- (meth)acryloyl means both acryloyl and methacryloyl.
- the photocurable liquid composition may contain a solvent (S). From the viewpoint of suppressing the strength reduction of the cured product due to the solvent (S) when forming the cured product, the photocurable liquid composition contains only a small amount of the solvent (S), or the photocurable liquid composition contains only a small amount of solvent (S). It is preferably free of solvent (S).
- the content of the solvent (S) in the photocurable liquid composition is preferably 5% by mass or less, more preferably 3% by mass or less, even more preferably 2% by mass or less, and even more preferably 1% by mass or less. 5% by mass or less is particularly preferred, and 0.3% by mass or less is most preferred.
- the content of the solvent (S) in the photocurable liquid composition is preferably 0% by mass or more. It is particularly preferred that the photocurable liquid composition is substantially free of solvent (S).
- the fact that the photocurable liquid composition does not substantially contain the solvent (S) means that a very small amount of the solvent (S) is inevitably brought into the photocurable liquid composition accompanying the raw materials, etc. It means that the solvent (S) is not intentionally added to the liquid composition.
- the content of the solvent (S) in the photocurable liquid composition is, for example, 0.2% by mass or less, and 0.15% by mass. % or less is preferable, 0.1 mass % or less is more preferable, and 0.05 mass % or less is even more preferable.
- the viscosity of the photocurable liquid composition is, for example, 70 cP or less, preferably 50 cP or less, more preferably 40 cP or less, and even more preferably 30 cP or less, as measured at 25° C. using an E-type viscometer. .
- the viscosity of the photocurable liquid composition can be adjusted, for example, by adjusting the content of the plasticizer (E), adjusting the content of the photopolymerizable monomer (A) or the metal compound particles (B), or by adjusting the content of the photocurable liquid composition. It can be adjusted by adding a small amount of solvent (S) to the liquid composition.
- the photocurable liquid composition contains a photopolymerizable monomer (A) having an ethylenically unsaturated double bond.
- the photopolymerizable monomer (A) is 2 or more because it is easy to form a cured product having excellent mechanical properties, and the photocurable liquid resin composition has excellent curability. It is preferable to contain a polyfunctional monomer (A1) having an ethylenically unsaturated double bond of
- the photopolymerizable monomer (A) is not particularly limited, and conventionally known polyfunctional monomers (A1) and monofunctional monomers (A2) can be used.
- polyfunctional monomer (A1) examples include ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, butylene Glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,6-hexane glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, glycerin di(meth)acrylate, glycerin tri(meth)acrylate , pentaerythritol di(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(me
- the photopolymerizable monomer (A) contains a polyfunctional monomer (A1) having 3 or more ethylenically unsaturated double bonds in that it is easy to suppress the localization of the metal oxide nanoparticles (B) in the cured product. is preferred.
- the polyfunctional monomer (A1) is an aliphatic compound that does not contain an aromatic group. is preferred.
- the number of ethylenically unsaturated double polymerization bonds possessed by the polyfunctional monomer (A1) is preferably 3 or more and 6 or less.
- Preferred specific examples of the polyfunctional monomer (A1) having 3 or more ethylenically unsaturated double bonds include trimethylolpropane tri(meth)acrylate, glycerin tri(meth)acrylate, pentaerythritol tri(meth) Acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, glycerin polyglycidyl ether poly(meth)acrylate, polyhydric alcohol and N-methylol(meth)acrylamide and condensates of.
- the photocurable liquid composition contains a compound represented by the following formula (A1) or the following formula (A2) as a polyfunctional monomer (A1) having 3 or more ethylenically unsaturated double bonds. is preferred.
- (MA-(O-R a1 ) na1 -X-CH 2 ) 2 -CH-X-(R a1 -O) na1 -MA (A2) (In Formula (A1) and Formula (A2), MA is each independently a (meth)acryloyl group, X is each independently an oxygen atom, —NH—, or —N(CH 3 )— and each R a1 is independently an ethane-1,2-diyl group, a propane-1,2-diyl group, or a propane-1,3-diyl group; R a2 is a hydroxyl group; an alkyl group of 1 or more and 4 or less, or a group represented by -X-(R a1 -O)
- the alkyl group having 1 to 4 carbon atoms as R a2 includes methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, and tert-butyl groups.
- a methyl group and an ethyl group are preferred.
- Preferred examples of the compound represented by formula (A1) and the compound represented by formula (A2) include pentaerythritol tetra(meth)acrylate, dipentaerythritol hexa(meth)acrylate, trimethylolpropane tri(meth) Acrylate, glycerin tri(meth)acrylate, and compounds 1) to 32) below.
- MA is a (meth)acryloyl group.
- the photopolymerizable monomer (A) contains a polyfunctional monomer (A1) having 3 or more ethylenically unsaturated double bonds, localization of the metal oxide nanoparticles (B) in the cured product is easily suppressed.
- the ratio of the mass of the polyfunctional monomer (A1) to the mass of the photopolymerizable monomer (A) is preferably 20% by mass or more and 70% by mass or less, more preferably 30% by mass or more and 70% by mass or less, and 40% by mass. % or more and 70 mass % or less is more preferable.
- the photopolymerizable monomer (A) preferably contains a compound represented by the following formula (a-1) as a polyfunctional monomer (A1) in terms of easy formation of a cured product with a high refractive index.
- R 1 and R 2 are each independently a hydrogen atom or a methyl group.
- R 3 and R 4 are each independently an alkyl group having 1 to 5 carbon atoms.
- p and q are each independently 0 or 1;
- R 1 and R 2 are each independently a hydrogen atom or a methyl group. R 1 and R 2 may be different from each other or may be the same. R 1 and R 2 are preferably the same because the sulfide compound (A1) is easily synthesized and available.
- R 3 and R 4 are each independently an alkyl group having 1 to 5 carbon atoms. R 3 and R 4 may be different from each other or may be the same. R 3 and R 4 are preferably the same because the sulfide compound (A1) is easily synthesized and available.
- the alkyl group having 1 to 5 carbon atoms as R 3 and R 4 may be linear or branched.
- alkyl groups having 1 to 5 carbon atoms as R 3 and R 4 include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group and tert-pentyl group.
- Preferred specific examples of the compound represented by formula (a-1) include the following compounds.
- the mass ratio of the polyfunctional monomer (A1) to the mass of the photopolymerizable monomer (A) has the desired effect such as the dispersibility of the metal oxide nanoparticles (B). It is not particularly limited as long as it is not damaged.
- the ratio of the mass of the polyfunctional monomer (A1) to the mass of the photopolymerizable monomer (A) is preferably 0% by mass or more, more preferably 10% by mass or more, even more preferably 20% by mass or more, and 30% by mass. The above are particularly preferred.
- the upper limit is, for example, 50% by mass or less, preferably 45% by mass or less.
- Monofunctional monomers (A2) include, for example, (meth)acrylamide, methylol(meth)acrylamide, methoxymethyl(meth)acrylamide, ethoxymethyl(meth)acrylamide, propoxymethyl(meth)acrylamide, butoxymethoxymethyl(meth)acrylamide , N-methylol (meth)acrylamide, N-hydroxymethyl (meth)acrylamide, (meth)acrylic acid, fumaric acid, maleic acid, maleic anhydride, itaconic acid, itaconic anhydride, citraconic acid, citraconic anhydride, crotonic acid , 2-acrylamido-2-methylpropanesulfonic acid, tert-butylacrylamidosulfonic acid, methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, cyclohexyl (meth)acrylate , 2-hydroxyethy
- the monofunctional monomer (A2) preferably contains a sulfur-containing (meth)acrylate represented by the following formula (A3) in that the localization of the metal oxide nanoparticles (B) in the cured product can be easily suppressed.
- Ar a1 -R a01 -SR a02 -O-CO-CR a03 CH 2 (A3)
- Ar a1 is a phenyl group optionally substituted with a halogen atom
- R a01 is a single bond or an alkylene group having 1 to 6 carbon atoms
- R a02 is an alkylene group having 1 to 6 carbon atoms
- R a03 is a hydrogen atom or a methyl group.
- Ar a1 is a phenyl group optionally substituted with a halogen atom.
- the number of halogen atoms bonded to the phenyl group is not particularly limited.
- the number of halogen atoms bonded to the phenyl group is preferably 1 or 2, more preferably 1.
- the plurality of halogen atoms bonded to the phenyl group may consist of the same kind of halogen atoms alone, or may consist of two or more kinds of halogen atoms.
- a halogen atom that can be bonded to a phenyl group includes a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, with a fluorine atom, a chlorine atom, and a bromine atom being preferred.
- Ar a1 is preferably an unsubstituted phenyl group.
- R a01 is a single bond or an alkylene group having 1 to 6 carbon atoms.
- alkylene group having 1 to 6 carbon atoms include methylene group, ethane-1,2-diyl group, propane-1,2-diyl group, propane-1,3-diyl group and butane-1,4-diyl group. , pentane-1,5-diyl groups, and hexane-1,6-diyl groups.
- R a01 is preferably a single bond and a methylene group, more preferably a single bond.
- R a02 is an alkylene group having 1 to 6 carbon atoms.
- the alkylene group having 1 to 6 carbon atoms include methylene group, ethane-1,2-diyl group, propane-1,2-diyl group, propane-1,3-diyl group and butane-1,4-diyl group. pentane-1,5-diyl group, and hexane-1,6-diyl group.
- R a02 is preferably a methylene group, an ethane-1,2-diyl group and a propane-1,3-diyl group, more preferably an ethane-1,2-diyl group and a propane-1,3-diyl group.
- Ar a1 is a phenyl group and R a01 is a single group.
- a bond is particularly preferred.
- sulfur-containing (meth)acrylates represented by formula (A3) include 2-phenylthioethyl (meth)acrylate, 3-phenylthiopropyl (meth)acrylate, 2-benzylthioethyl (meth) Acrylates, 3-benzylthiopropyl (meth)acrylate, 2-(2-chlorophenyl)ethyl (meth)acrylate, 2-(3-chlorophenyl)ethyl (meth)acrylate, 2-(4-chlorophenyl)ethyl (meth)acrylate , 3-(2-chlorophenyl)propyl (meth)acrylate, 3-(3-chlorophenyl)propyl (meth)acrylate, 3-(4-chlorophenyl)propyl (meth)acrylate, 2-(2-fluorophenyl)ethyl ( meth)acrylate, 2-(3-fluorophenyl)ethyl (meth)acrylate,
- the mass ratio of the sulfur-containing (meth)acrylate represented by the formula (A3) to the mass of the photopolymerizable monomer (A) is not particularly limited as long as the desired effect is not impaired.
- the ratio of the mass of the sulfur-containing (meth)acrylate represented by the formula (A3) to the mass of the photopolymerizable monomer (A) is preferably 40% by mass or more and 100% by mass or less, and 60% by mass or more and 100% by mass or less. is more preferably 70% by mass or more and 100% by mass or less, and particularly preferably 80% by mass or more and 100% by mass or less.
- the sulfur-containing (meth)acrylates represented by formula (A3) may be used singly or in combination of two or more.
- the ratio of the mass of the monofunctional monomer (A3) to the mass of the photopolymerizable monomer (A) is within a range that does not impair the desired effect. It is not particularly limited.
- the ratio of the mass of the monofunctional monomer (A3) to the mass of the photopolymerizable monomer (A) is preferably 50% by mass or more, more preferably 55% by mass or more.
- the upper limit may be, for example, 80% by mass.
- the ratio of the mass of the photopolymerizable monomer (A) to the mass of the photocurable liquid composition excluding the mass of the solvent (S) is preferably 20% by mass or more and 90% by mass or less, and 23% by mass or more and 60% by mass. The following is more preferable, and 33% by mass or more and 50% by mass or less is even more preferable.
- the photocurable liquid composition contains metal oxide nanoparticles (B).
- the type of metal oxide that constitutes the metal oxide nanoparticles is not particularly limited as long as the desired effect is not impaired.
- Preferred examples of the metal oxide nanoparticles (B) include at least one selected from the group consisting of zirconium oxide nanoparticles, titanium oxide nanoparticles, barium titanate nanoparticles, and cerium oxide nanoparticles.
- the photocurable liquid composition may contain one of these metal oxide nanoparticles (B) alone, or may contain two or more of them in combination. When the photocurable liquid composition contains the metal oxide nanoparticles (B), it is possible to form a cured product exhibiting a high refractive index.
- the average particle size of the metal oxide nanoparticles (B) is preferably 500 nm or less, preferably 2 nm or more and 100 nm or less, from the viewpoint of the transparency of the cured product.
- the surface of the metal oxide nanoparticles (B) is preferably modified with ethylenically unsaturated double bond-containing groups.
- the photopolymerizable monomer (A) is added to the metal oxide nanoparticles (B )
- the metal oxide nanoparticles (B) are immobilized in the matrix composed of the polymer of the photopolymerizable monomer (A). This makes it difficult for the metal oxide nanoparticles (B) to aggregate. Therefore, when the surfaces of the metal oxide nanoparticles (B) are modified with ethylenically unsaturated double bond-containing groups, localization of the metal oxide nanoparticles (B) in the cured product is particularly easily suppressed.
- metal oxide nanoparticles (B) For example, by allowing a capping agent containing an ethylenically unsaturated double bond to act on the surface of the metal oxide nanoparticles (B), the surface becomes an ethylenically unsaturated double bond through a chemical bond such as a covalent bond. Metal oxide nanoparticles (B) modified with bond-containing groups are obtained.
- the method of bonding the capping agent containing an ethylenically unsaturated double bond to the surface of the metal oxide nanoparticles (B) via a chemical bond such as a covalent bond is not particularly limited. Hydroxyl groups are usually present on the surface of the metal oxide nanoparticles (B). By reacting the hydroxyl group with the reactive group of the capping agent, the capping agent is covalently bonded to the surface of the metal oxide nanoparticles (B).
- a trialkoxysilyl group such as a trimethoxysilyl group and a triethoxysilyl group
- a dialkoxysilyl group such as a dimethoxysilyl group and a diethoxysilyl group
- a trialkoxysilyl group, a dialkoxysilyl group, a monoalkoxysilyl group, a trihalosilyl group, a dihalosilyl group, and a monohalosilyl group form a siloxane bond with the surface of the metal oxide nanoparticles (B).
- a carboxy group and a halocarbonyl group form a bond represented by (metal oxide —O—CO—) with the surface of the metal oxide nanoparticles (B).
- the hydroxyl group forms a bond represented by (metal oxide —O—) with the surface of the metal oxide nanoparticles (B).
- the groups that bind to the above reactive groups include hydrogen atoms and various organic groups.
- the organic group may contain heteroatoms such as O, N, S, P, B, Si, and halogen atoms.
- the groups that bind to the above reactive groups include, for example, linear or branched alkyl groups that may be interrupted by oxygen atoms (—O—), linear or branched an alkenyl group optionally interrupted by an oxygen atom (--O--), may be linear or branched, and is interrupted by an oxygen atom (--O--) alkynyl groups, cycloalkyl groups, aromatic hydrocarbon groups, heterocyclic groups, etc., which may be substituted.
- substituents such as halogen atoms, epoxy group-containing groups such as glycidyl groups, hydroxyl groups, mercapto groups, amino groups, (meth)acryloyl groups, and isocyanate groups.
- substituents such as halogen atoms, epoxy group-containing groups such as glycidyl groups, hydroxyl groups, mercapto groups, amino groups, (meth)acryloyl groups, and isocyanate groups.
- the number of substituents is not particularly limited.
- R b1 , R b2 , R b3 and Rb4 are each an organic group which may be the same or different.
- organic groups include alkyl groups such as methyl group and ethyl group; alkenyl groups such as vinyl group and allyl group; aromatic hydrocarbon groups such as phenyl group, naphthyl group and tolyl group; Epoxy group-containing groups such as propyl group; (meth)acryloyloxy group and the like.
- r and s in the above formula are each independently an integer of 0 or more and 60 or less. Both r and s in the above formula cannot be zero.
- capping agents include vinyltrimethoxysilane, vinyltriethoxysilane, allyltrimethoxysilane, allyltriethoxysilane, 1-hexenyltrimethoxysilane, 1-hexenyltriethoxysilane, 1-octenyltrimethoxysilane. Unsaturated groups such as silane, 1-octenyltriethoxysilane, 3-acryloyloxypropyltrimethoxysilane, 3-acryloylpropyltriethoxysilane, 3-methacryloyloxypropyltrimethoxysilane, 3-methacryloyloxypropyltriethoxysilane, etc.
- alkoxysilane Containing alkoxysilane; unsaturated group-containing alcohols such as 2-hydroxyethyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, allyl alcohol, ethylene glycol monoallyl ether, propylene glycol monoallyl ether, and 3-allyloxypropanol (meth)acrylic acid; (meth)acrylic acid halides such as (meth)acrylic acid chloride;
- the amount of the capping agent used when bonding the capping agent to the surface of the metal oxide nanoparticles (B) via a chemical bond such as a covalent bond is not particularly limited.
- a sufficient amount of capping agent is used to react with substantially all of the hydroxyl groups on the surface of the metal oxide nanoparticles (B).
- the content of the metal oxide nanoparticles (B) in the photocurable liquid composition is not particularly limited as long as the object of the present invention is not impaired.
- the content of the metal oxide nanoparticles (B) in the photocurable liquid composition is, for example, 5% by mass or more and 95% by mass with respect to the mass of the photocurable liquid composition excluding the mass of the solvent (S). %, preferably 5% by mass or more and 75% by mass or less, more preferably 35% by mass or more and 70% by mass or less, and even more preferably 40% by mass or more and 65% by mass or less. In order to increase the refractive index of the cured product, it is preferably 40% by mass or more and 93% by mass or less.
- the content of the metal oxide nanoparticles (B) in the photocurable liquid composition is within the above range, localization of the metal oxide nanoparticles (B) in the cured product is suppressed, and high refractive index is achieved. It is easy to form a hardened product of a rate.
- the surface of the metal oxide nanoparticles (B) is modified with an ethylenically unsaturated double bond-containing group, the ethylenically unsaturated double bonds present on the surface of the metal oxide nanoparticles (B)
- the weight of the capping agent having containing groups is included in the weight of the metal oxide nanoparticles (B).
- the photopolymerization initiator (C) is not particularly limited, and conventionally known photopolymerization initiators can be used.
- photopolymerization initiator (C) examples include 1-hydroxycyclohexylphenyl ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-[4-(2-hydroxyethoxy) Phenyl]-2-hydroxy-2-methyl-1-propan-1-one, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 1-(4-dodecylphenyl)- 2-hydroxy-2-methylpropan-1-one, 2,2-dimethoxy-1,2-diphenylethan-1-one, bis(4-dimethylaminophenyl)ketone, 2-methyl-1-[4-( methylthio)phenyl]-2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one, O-acetyl-1-[6-( 2-methylbenzoyl)-9-ethyl-9H-carbazol-3-yl
- oxime ester compounds are preferred from the viewpoint of the sensitivity of the photocurable liquid composition.
- oxime ester compound a compound having a partial structure represented by the following formula (c1) is preferable.
- n1 is 0 or 1
- R c2 is a monovalent organic group
- R c3 is a hydrogen atom, an optionally substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an optionally substituted aryl group
- * is a bond.
- the compound having the partial structure represented by formula (c1) preferably has a carbazole skeleton, fluorene skeleton, diphenyl ether skeleton, or phenyl sulfide skeleton.
- the compound having the partial structure represented by formula (c1) preferably has one or two partial structures represented by formula (c1).
- Compounds having a partial structure represented by formula (c1) include compounds represented by the following formula (c2).
- R c1 is a group represented by the following formula (c3), (c4), or (c5), n1 is 0 or 1, R c2 is a monovalent organic group, R c3 is a hydrogen atom, an optionally substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an optionally substituted aryl group.
- R c4 and R c5 are each independently a monovalent organic group, n2 is an integer of 0 or more and 3 or less, When n2 is 2 or 3, multiple R c5 may be the same or different, and multiple R c5 may combine with each other to form a ring. * is a bond.
- R c6 and R c7 each independently represent an optionally substituted chain alkyl group, an optionally substituted chain alkoxy group, a substituted is a cyclic organic group or a hydrogen atom, R c6 and R c7 may combine with each other to form a ring, R c7 and the benzene ring in the fluorene skeleton may be bonded to each other to form a ring, R c8 is a nitro group or a monovalent organic group, n3 is an integer of 0 to 4, * is a bond.
- R c9 is a monovalent organic group, a halogen atom, a nitro group, or a cyano group, A is S or O; n4 is an integer of 0 to 4, * is a bond.
- R c4 is a monovalent organic group.
- R c4 can be selected from various organic groups as long as the objects of the present invention are not impaired.
- a carbon atom-containing group is preferable, and one or more carbon atoms and one or more atoms selected from the group consisting of H, O, S, Se, N, B, P, Si, and halogen atoms.
- a group consisting of is more preferred.
- the number of carbon atoms in the carbon atom-containing group is not particularly limited, and is preferably 1 or more and 50 or less, more preferably 1 or more and 20 or less.
- R c4 include an optionally substituted alkyl group having 1 to 20 carbon atoms, an optionally substituted cycloalkyl group having 3 to 20 carbon atoms, and a carbon atom
- a saturated aliphatic acyl group optionally having 2 to 20 substituents, an alkoxycarbonyl group having 2 to 20 carbon atoms optionally having a substituent, a phenyl group optionally having a substituent , an optionally substituted benzoyl group, an optionally substituted phenoxycarbonyl group, an optionally substituted phenylalkyl group having 7 to 20 carbon atoms, having a substituent optionally substituted naphthyl group, optionally substituted naphthoxycarbonyl group, optionally substituted naphthylalkyl group having 11 to 20 carbon atoms, substituted a heterocyclyl group optionally having a group, a heterocyclylcarbonyl group optionally having a substituent, and the like.
- an alkyl group having 1 to 20 carbon atoms is preferable.
- the alkyl group may be linear or branched.
- the number of carbon atoms in the alkyl group as R c4 is preferably 2 or more, more preferably 5 or more, from the viewpoint of good solubility of the compound represented by formula (c3) in the photocurable liquid composition. , 7 or more are particularly preferred. Further, from the viewpoint of good compatibility between the compound represented by formula (c3) and other components in the photocurable liquid composition, the number of carbon atoms in the alkyl group as R c4 is 15 or less is preferable, and 10 or less is more preferable.
- R c4 has a substituent
- substituents include a hydroxyl group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, and 2 to 20 carbon atoms.
- the heterocyclyl group may be an aliphatic heterocyclic group or an aromatic heterocyclic group.
- the heterocyclyl group is a 5- or 6-membered monocyclic ring containing one or more N, S, O, or such monocyclic rings are fused together or such monocyclic rings are fused with a benzene ring. is a heterocyclyl group.
- the heterocyclyl group is a condensed ring, the number of monocyclic rings constituting the condensed ring shall be up to 3.
- Heterocyclic rings constituting such heterocyclyl groups include furan, thiophene, pyrrole, oxazole, isoxazole, thiazole, thiadiazole, isothiazole, imidazole, pyrazole, triazole, pyridine, pyrazine, pyrimidine, pyridazine, benzofuran, benzothiophene, indole, isoindole, indolizine, benzimidazole, benzotriazole, benzoxazole, benzothiazole, carbazole, purine, quinoline, isoquinoline, quinazoline, phthalazine, cinnoline, quinoxaline, piperidine, piperazine, morpholine, piperidine, tetrahydropyran, and tetrahydrofuran; be done.
- R c4 is a heterocyclyl group
- substituents that the heterocyclyl group may have include a hydroxyl group, an alkoxy group having 1 to 6 carbon atoms, a halogen atom, a cyano group, a nitro group, and the like.
- R c4 examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, Examples include isopentyl, neopentyl, pentan-3-yl, sec-pentyl, tert-pentyl, n-hexyl, n-heptyl, n-octyl, and 2-ethylhexyl groups. Further, n-octyl group and 2-ethylhexyl group are preferred, and 2-ethylhexyl group is more preferred, from the viewpoint of good solubility of the compound represented by formula (c3) in the curable composition.
- R c5 is a monovalent organic group.
- R c5 can be selected from various organic groups as long as the objects of the present invention are not impaired.
- a carbon atom-containing group is preferable, and one or more carbon atoms and one or more atoms selected from the group consisting of H, O, S, Se, N, B, P, Si, and halogen atoms.
- a group consisting of is more preferred.
- the number of carbon atoms in the carbon atom-containing group is not particularly limited, and is preferably 1 or more and 50 or less, more preferably 1 or more and 20 or less.
- Examples of monovalent organic groups suitable as R c5 include alkyl groups, alkoxy groups, cycloalkyl groups, cycloalkoxy groups, saturated aliphatic acyl groups, alkoxycarbonyl groups, saturated aliphatic acyloxy groups, and substituents.
- optionally substituted phenyl group optionally substituted phenoxy group, optionally substituted benzoyl group, optionally substituted phenoxycarbonyl group, optionally substituted benzoyloxy a phenylalkyl group optionally having substituents, a naphthyl group optionally having substituents, a naphthoxy group optionally having substituents, a naphthoyl group optionally having substituents, a substituent an optionally substituted naphthoxycarbonyl group, an optionally substituted naphthyloxy group, an optionally substituted naphthylalkyl group, an optionally substituted heterocyclyl group, an optionally substituted heterocyclylcarbonyl group, amino group substituted with one or two organic groups, morpholin-1-yl group, piperazin-1-yl group, halogen, nitro group, cyano group, HX 2 C- or H 2 Substituents including a group represented by XC— (wherein each X
- R c5 is an alkyl group
- the number of carbon atoms in the alkyl group is preferably 1 or more and 20 or less, more preferably 1 or more and 6 or less.
- R c5 is an alkyl group, it may be linear or branched. Specific examples of when R c5 is an alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl and n-pentyl groups.
- R c5 is an alkyl group
- the alkyl group may contain an ether bond (--O--) in the carbon chain.
- alkyl groups having an ether bond in the carbon chain examples include methoxyethyl, ethoxyethyl, methoxyethoxyethyl, ethoxyethoxyethyl, propyloxyethoxyethyl, and methoxypropyl groups.
- R c5 is an alkoxy group
- the number of carbon atoms in the alkoxy group is preferably 1 or more and 20 or less, more preferably 1 or more and 6 or less.
- R c5 is an alkoxy group, it may be linear or branched.
- R c5 being an alkoxy group
- R c5 being an alkoxy group
- R c5 being an alkoxy group
- R c5 being an alkoxy group
- R c5 isopentyloxy group, sec-pentyloxy group, tert-pentyloxy group, n-hexyloxy group, n-heptyloxy group, n-octyloxy group, isooctyloxy group, sec-octyloxy group , tert-octyloxy group, n-nonyloxy group, isononyloxy group, n-decyloxy group, and isodecyloxy group.
- R c5 is an alkoxy group
- the alkoxy group may contain an ether bond (--O--) in the carbon chain.
- alkoxy groups having an ether bond in the carbon chain include methoxyethoxy, ethoxyethoxy, methoxyethoxyethoxy, ethoxyethoxyethoxy, propyloxyethoxyethoxy, methoxypropyloxy and the like.
- R c5 is a cycloalkyl group or a cycloalkoxy group
- the number of carbon atoms in the cycloalkyl group or cycloalkoxy group is preferably 3 or more and 10 or less, more preferably 3 or more and 6 or less.
- Specific examples of R c5 being a cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group.
- R c5 being a cycloalkoxy group
- R c5 being a cycloalkoxy group
- R c5 being a cycloalkoxy group
- R c5 being a cycloalkoxy group
- R c5 being a cycloalkoxy group
- R c5 being a cycloalkoxy group
- R c5 is a saturated aliphatic acyl group or saturated aliphatic acyloxy group
- the number of carbon atoms in the saturated aliphatic acyl group or saturated aliphatic acyloxy group is preferably 2 or more and 21 or less, more preferably 2 or more and 7 or less.
- R c5 being a saturated aliphatic acyl group
- R c5 being a saturated aliphatic acyl group
- R c5 being a saturated aliphatic acyl group
- R c5 being a saturated aliphatic acyl group
- R c5 being a saturated aliphatic acyl group
- R c5 being a saturated aliphatic acyl group
- R c5 being a saturated aliphatic acyl group
- R c5 being a saturated aliphatic acyl group
- R c5 being a saturated aliphatic acyl group
- R c5 being a saturated aliphatic acyloxy group
- R c5 being a saturated aliphatic acyloxy group
- R c5 being a saturated aliphatic acyloxy group
- R c5 being a saturated aliphatic acyloxy group
- R c5 being a saturated aliphatic acyloxy group
- R c5 is an alkoxycarbonyl group
- the number of carbon atoms in the alkoxycarbonyl group is preferably 2 or more and 20 or less, more preferably 2 or more and 7 or less.
- Specific examples of R c5 being an alkoxycarbonyl group include methoxycarbonyl, ethoxycarbonyl, n-propyloxycarbonyl, isopropyloxycarbonyl, n-butyloxycarbonyl, isobutyloxycarbonyl, sec-butyl oxycarbonyl group, tert-butyloxycarbonyl group, n-pentyloxycarbonyl group, isopentyloxycarbonyl group, sec-pentyloxycarbonyl group, tert-pentyloxycarbonyl group, n-hexyloxycarbonyl group, n-heptyloxycarbonyl group, n-octyloxycarbonyl group, isooctyloxycarbony
- R c5 is a phenylalkyl group
- the number of carbon atoms in the phenylalkyl group is preferably 7 or more and 20 or less, more preferably 7 or more and 10 or less.
- R c5 is a naphthylalkyl group
- the number of carbon atoms in the naphthylalkyl group is preferably 11 or more and 20 or less, more preferably 11 or more and 14 or less.
- Specific examples of R c5 being a phenylalkyl group include a benzyl group, a 2-phenylethyl group, a 3-phenylpropyl group and a 4-phenylbutyl group.
- R c5 when R c5 is a naphthylalkyl group include an ⁇ -naphthylmethyl group, a ⁇ -naphthylmethyl group, a 2-( ⁇ -naphthyl)ethyl group, and a 2-( ⁇ -naphthyl)ethyl group.
- R c5 when R c5 is a phenylalkyl group or a naphthylalkyl group, R c5 may further have a substituent on the phenyl group or naphthyl group.
- R c5 is a heterocyclyl group
- the heterocyclyl group is the same as when R c4 in formula (c3) is a heterocyclyl group, and the heterocyclyl group may further have a substituent.
- R c5 is a heterocyclylcarbonyl group
- the heterocyclyl group contained in the heterocyclylcarbonyl group is the same as when R c5 is a heterocyclyl group.
- R c5 is an amino group substituted with 1 or 2 organic groups
- preferred examples of the organic group include an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, saturated aliphatic acyl group having 2 to 21 carbon atoms, optionally substituted phenyl group, optionally substituted benzoyl group, optionally substituted 7 to 20 carbon atoms
- amino group substituted with one or two organic groups include methylamino group, ethylamino group, diethylamino group, n-propylamino group, di-n-propylamino group, isopropylamino group, n- butylamino group, di-n-butylamino group, n-pentylamino group, n-hexylamino group, n-heptylamino group, n-octylamino group, n-nonylamino group, n-decylamino group, phenylamino group, naphthylamino group, acetylamino group, propanoylamino group, n-butanoylamino group, n-pentanoylamino group, n-hexanoylamino group, n-heptanoylamino group, n-octanoylamino
- the substituent includes a group represented by HX 2 C-- or H 2 XC-- (eg, HX 2 C— or H 2 XC—, a halogenated alkoxy group containing a group represented by HX 2 C— or H 2 XC—, a halogenated alkyl group containing a group represented by HX 2 C— or H 2 XC—), Alkyl group, alkoxy group having 1 to 6 carbon atoms, saturated aliphatic acyl group having 2 to 7 carbon atoms, alkoxycarbonyl group having 2 to 7 carbon atoms, saturated fat having 2 to 7 carbon atoms group acyloxy group, monoalkylamino group having an alkyl group having 1 to 6 carbon atoms, dialkylamino group having an alkyl group having 1 to 6 carbon atoms, morpholin-1-yl group, pipe
- the number of substituents is not limited as long as the object of the present invention is not impaired, and is preferably 1 to 4.
- the phenyl group, naphthyl group and heterocyclyl group contained in R c5 have multiple substituents, the multiple substituents may be the same or different.
- Substituents contained in R c5 when the benzoyl group further has a substituent include an alkyl group having 1 to 6 carbon atoms, a morpholin-1-yl group, a piperazin-1-yl group, and a 2-thenoyl group. (thiophen-2-ylcarbonyl group), furan-3-ylcarbonyl group and phenyl group.
- the halogen atom represented by X includes a fluorine atom, a chlorine atom, a bromine atom, etc., and is preferably a fluorine atom.
- the substituent containing a group represented by HX 2 C-- or H 2 XC-- includes a halogenated alkoxy group containing a group represented by HX 2 C-- or H 2 XC--, HX 2 C-- or H 2 XC- A group having a halogenated alkoxy group including a group represented by -, a halogenated alkyl group including a group represented by HX 2 C- or H 2 XC-, represented by HX 2 C- or H 2 XC- and a group having a halogenated alkyl group containing a group, such as a halogenated alkoxy group containing a group represented by HX 2 C-- or H 2 XC--, or represented by HX 2 C-- or H 2 XC-- More preferably, it is a group having a halogenated alkoxy group containing group.
- the group having a halogenated alkyl group containing a group represented by HX 2 C-- or H 2 XC-- is substituted with a halogenated alkyl group containing a group represented by HX 2 C-- or H 2 XC--.
- aromatic groups eg, phenyl group, naphthyl group, etc.
- cycloalkyl groups substituted with halogenated alkyl groups including groups represented by HX 2 C-- or H 2 XC-- eg, cyclopentyl group, cyclohexyl groups, etc.
- the group having a halogenated alkoxy group containing a group represented by HX 2 C-- or H 2 XC-- is substituted with a halogenated alkoxy group containing a group represented by HX 2 C-- or H 2 XC--.
- aromatic groups e.g., phenyl group, naphthyl group, etc.
- alkyl groups substituted with halogenated alkoxy groups including groups represented by HX 2 C- or H 2 XC- e.g., methyl group, ethyl group , n-propyl group, i-propyl group, etc.
- a cycloalkyl group substituted with a halogenated alkoxy group including a group represented by HX 2 C- or H 2 XC- e.g., cyclopentyl group, cyclohexyl group, etc.
- Rc5 is also preferably a cycloalkylalkyl group, a phenoxyalkyl group optionally having a substituent on the aromatic ring, and a phenylthioalkyl group optionally having a substituent on the aromatic ring.
- the substituents that the phenoxyalkyl group and the phenylthioalkyl group may have are the same as the substituents that the phenyl group contained in R c5 may have.
- R c5 is an alkyl group, a cycloalkyl group, an optionally substituted phenyl group, a cycloalkylalkyl group, or an aromatic ring which may have a substituent.
- Good phenylthioalkyl groups are preferred.
- the alkyl group an alkyl group having 1 to 20 carbon atoms is preferable, an alkyl group having 1 to 8 carbon atoms is more preferable, an alkyl group having 1 to 4 carbon atoms is particularly preferable, and a methyl group is most preferable. preferable.
- the optionally substituted phenyl groups a methylphenyl group is preferred, and a 2-methylphenyl group is more preferred.
- the number of carbon atoms in the cycloalkyl group contained in the cycloalkylalkyl group is preferably 5 or more and 10 or less, more preferably 5 or more and 8 or less, and particularly preferably 5 or 6.
- the number of carbon atoms in the alkylene group contained in the cycloalkylalkyl group is preferably 1 or more and 8 or less, more preferably 1 or more and 4 or less, and particularly preferably 2.
- a cyclopentylethyl group is preferred.
- the number of carbon atoms in the alkylene group contained in the phenylthioalkyl group which may have a substituent on the aromatic ring is preferably 1 or more and 8 or less, more preferably 1 or more and 4 or less, and particularly preferably 2.
- a 2-(4-chlorophenylthio)ethyl group is preferred.
- the formed ring when a plurality of R c5 are present and the plurality of R c5 are bonded to each other to form a ring, the formed ring includes a hydrocarbon ring, a heterocyclic ring, and the like. be done. Heteroatoms contained in heterocycles include, for example, N, O and S. Aromatic rings are particularly preferred as the ring formed by combining a plurality of R c5 s. Such an aromatic ring may be an aromatic hydrocarbon ring or an aromatic heterocyclic ring. As such an aromatic ring, an aromatic hydrocarbon ring is preferred. Specific examples of the case where a plurality of R c5 in formula (c3) are bonded to each other to form a benzene ring are shown below.
- R c8 is a nitro group or a monovalent organic group.
- R c8 is bonded to a 6-membered aromatic ring different from the aromatic ring bonded to the group represented by —(CO) n1 — on the condensed ring in formula (c4).
- the bonding position of R c8 is not particularly limited.
- the group represented by formula (c4) has one or more R c8 , one of the one or more R c8 is fluorene, because the compound represented by formula (c4) is easily synthesized. Attachment to the 7-position of the backbone is preferred.
- the group represented by formula (c4) when the group represented by formula (c4) has 1 or more R c8 , the group represented by formula (c4) is preferably represented by the following formula (c6). When there are multiple R c8s , the multiple R c8s may be the same or different.
- R c6 , R c7 , R c8 and n3 are respectively the same as R c6 , R c7 , R c8 and n3 in formula (c4).
- R c8 is not particularly limited as long as the object of the present invention is not impaired.
- a carbon atom-containing group is preferable, and one or more carbon atoms and one or more atoms selected from the group consisting of H, O, S, Se, N, B, P, Si, and halogen atoms. A group consisting of is more preferred.
- the number of carbon atoms in the carbon atom-containing group is not particularly limited, and is preferably 1 or more and 50 or less, more preferably 1 or more and 20 or less.
- Preferred examples of the monovalent organic group for R c8 include the same preferred examples of the monovalent organic group as R c5 in formula (c3).
- R c6 and R c7 are each an optionally substituted chain alkyl group, an optionally substituted chain alkoxy group, an optionally substituted cyclic It is an organic group or a hydrogen atom. R c6 and R c7 may combine with each other to form a ring. Among these groups, chain alkyl groups which may have a substituent are preferable as R c6 and R c7 . When R c6 and R c7 are a chain alkyl group which may have a substituent, the chain alkyl group may be a straight chain alkyl group or a branched chain alkyl group.
- R c6 and R c7 are unsubstituted chain alkyl groups
- the number of carbon atoms in the chain alkyl group is preferably 1 or more and 20 or less, more preferably 1 or more and 10 or less, and particularly 1 or more and 6 or less.
- Specific examples of R c6 and R c7 being chain alkyl groups include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group and tert-butyl group.
- n-pentyl group isopentyl group, sec-pentyl group, tert-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, n-decyl group, and isodecyl group.
- R c6 and R c7 are alkyl groups
- the alkyl group may contain an ether bond (--O--) in the carbon chain.
- alkyl groups having an ether bond in the carbon chain examples include methoxyethyl, ethoxyethyl, methoxyethoxyethyl, ethoxyethoxyethyl, propyloxyethoxyethyl, and methoxypropyl groups.
- R c6 and R c7 are chain alkyl groups having a substituent
- the number of carbon atoms in the chain alkyl group is preferably 1 or more and 20 or less, more preferably 1 or more and 10 or less, and particularly preferably 1 or more and 6 or less.
- the number of carbon atoms in the substituent is not included in the number of carbon atoms in the chain alkyl group.
- a chain alkyl group having a substituent is preferably linear.
- the substituents that the alkyl group may have are not particularly limited as long as they do not interfere with the object of the present invention. Suitable examples of substituents include alkoxy groups, cyano groups, halogen atoms, halogenated alkyl groups, cyclic organic groups, and alkoxycarbonyl groups.
- Halogen atoms include fluorine, chlorine, bromine and iodine atoms. Among these, a fluorine atom, a chlorine atom and a bromine atom are preferred.
- Cyclic organic groups include cycloalkyl groups, aromatic hydrocarbon groups, and heterocyclyl groups. Specific examples of the cycloalkyl group are the same as the preferred examples when R c8 is a cycloalkyl group.
- aromatic hydrocarbon groups include phenyl, naphthyl, biphenylyl, anthryl, and phenanthryl groups.
- heterocyclyl group are the same as the preferred examples when R c8 is a heterocyclyl group.
- R c8 is an alkoxycarbonyl group
- the alkoxy group contained in the alkoxycarbonyl group may be linear or branched, preferably linear.
- the number of carbon atoms in the alkoxy group contained in the alkoxycarbonyl group is preferably 1 or more and 10 or less, more preferably 1 or more and 6 or less.
- the number of substituents is not particularly limited.
- the preferred number of substituents varies depending on the number of carbon atoms in the chain alkyl group.
- the number of substituents is typically 1 or more and 20 or less, preferably 1 or more and 10 or less, and more preferably 1 or more and 6 or less.
- R c6 and R c7 are chain alkoxy groups having no substituents
- the number of carbon atoms in the chain alkoxy group is preferably 1 or more and 20 or less, more preferably 1 or more and 10 or less, and particularly 1 or more and 6 or less. preferable.
- R c6 and R c7 being chain alkoxy groups include methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, isobutyloxy, sec-butyloxy, tert -butyloxy group, n-pentyloxy group, isopentyloxy group, sec-pentyloxy group, tert-pentyloxy group, n-hexyloxy group, n-heptyloxy group, n-octyloxy group, isooctyloxy group, sec-octyloxy group, tert-octyloxy group, n-nonyloxy group, isononyloxy group, n-decyloxy group, isodecyloxy group and the like.
- R c6 and R c7 are alkoxy groups
- the alkoxy groups may contain an ether bond (--O--) in the carbon chain.
- alkoxy groups having an ether bond in the carbon chain include methoxyethoxy, ethoxyethoxy, methoxyethoxyethoxy, ethoxyethoxyethoxy, propyloxyethoxyethoxy, methoxypropyloxy and the like.
- R c6 and R c7 are chain alkoxy groups having substituents
- the substituents that the alkoxy groups may have are the same as in the case where R c6 and R c7 are chain alkyl groups.
- R c6 and R c7 are cyclic organic groups
- the cyclic organic group may be an alicyclic group or an aromatic group.
- Cyclic organic groups include aliphatic cyclic hydrocarbon groups, aromatic hydrocarbon groups, and heterocyclyl groups.
- R c6 and R c7 are cyclic organic groups, the substituents that the cyclic organic groups may have are the same as in the case where R c6 and R c7 are chain alkyl groups.
- the aromatic hydrocarbon group is a phenyl group or a group formed by combining multiple benzene rings via carbon-carbon bonds. , is preferably a group formed by condensing a plurality of benzene rings.
- the aromatic hydrocarbon group is a phenyl group or a group formed by bonding or condensing a plurality of benzene rings
- the number of benzene rings contained in the aromatic hydrocarbon group is not particularly limited, 3 or less is preferable, 2 or less is more preferable, and 1 is particularly preferable.
- Preferred specific examples of aromatic hydrocarbon groups include phenyl, naphthyl, biphenylyl, anthryl, and phenanthryl groups.
- R c6 and R c7 are aliphatic cyclic hydrocarbon groups
- the aliphatic cyclic hydrocarbon groups may be monocyclic or polycyclic.
- the number of carbon atoms in the aliphatic cyclic hydrocarbon group is not particularly limited, it is preferably 3 or more and 20 or less, more preferably 3 or more and 10 or less.
- Examples of monocyclic cyclic hydrocarbon groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, norbornyl, isobornyl, tricyclononyl, tricyclodecyl, A tetracyclododecyl group, an adamantyl group, and the like can be mentioned.
- R c6 and R c7 are heterocyclyl groups
- the same heterocyclyl groups as R c5 in formula (c3) can be mentioned.
- R c6 and R c7 may combine with each other to form a ring.
- a group consisting of a ring formed by R c6 and R c7 is preferably a cycloalkylidene group.
- the ring constituting the cycloalkylidene group is preferably a 5- to 6-membered ring, more preferably a 5-membered ring.
- the ring may be either an aromatic ring or an aliphatic ring.
- the cycloalkylidene group may be fused with one or more other rings.
- rings that may be condensed with a cycloalkylidene group include benzene ring, naphthalene ring, cyclobutane ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, cyclooctane ring, furan ring, thiophene ring, pyrrole ring, and pyridine.
- R c6 and R c7 examples include groups represented by the formula -A 1 -A 2 .
- a 1 is a linear alkylene group
- a 2 is an alkoxy group, a cyano group, a halogen atom, a halogenated alkyl group, a cyclic organic group, or an alkoxycarbonyl group.
- the number of carbon atoms in the linear alkylene group for A 1 is preferably 1 or more and 10 or less, more preferably 1 or more and 6 or less.
- A2 is an alkoxy group
- the alkoxy group may be linear or branched, preferably linear.
- the number of carbon atoms in the alkoxy group is preferably 1 or more and 10 or less, more preferably 1 or more and 6 or less.
- A2 is a halogen atom, it is preferably a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, more preferably a fluorine atom, a chlorine atom or a bromine atom.
- the halogen atom contained in the halogenated alkyl group is preferably a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, more preferably a fluorine atom, a chlorine atom or a bromine atom.
- the halogenated alkyl group may be linear or branched, preferably linear.
- A2 is a cyclic organic group
- examples of the cyclic organic group are the same as the cyclic organic groups that Rc6 and Rc7 have as substituents.
- A2 is an alkoxycarbonyl group
- examples of the alkoxycarbonyl group are the same as the alkoxycarbonyl groups that Rc6 and Rc7 have as substituents.
- R c6 and R c7 include alkyl groups such as ethyl, n-propyl, n-butyl, n-hexyl, n-heptyl, and n-octyl groups; 2-methoxyethyl; group, 3-methoxy-n-propyl group, 4-methoxy-n-butyl group, 5-methoxy-n-pentyl group, 6-methoxy-n-hexyl group, 7-methoxy-n-heptyl group, 8-methoxy -n-octyl group, 2-ethoxyethyl group, 3-ethoxy-n-propyl group, 4-ethoxy-n-butyl group, 5-ethoxy-n-pentyl group, 6-ethoxy-n-hexyl group, 7- Alkoxyalkyl groups such as ethoxy-n-heptyl group and 8-ethoxy-n-octyl groups; 2-
- Alkyl group 2-cyclohexylethyl group, 3-cyclohexyl-n-propyl group, 4-cyclohexyl-n-butyl group, 5-cyclohexyl-n-pentyl group, 6-cyclohexyl-n-hexyl group, 7-cyclohexyl-n -heptyl group, 8-cyclohexyl-n-octyl group, 2-cyclopentylethyl group, 3-cyclopentyl-n-propyl group, 4-cyclopentyl-n-butyl group, 5-cyclopentyl-n-pentyl group, 6-cyclopentyl- Cycloalkylalkyl groups such as n-hexyl group, 7-cyclopentyl-n-heptyl group, and 8-cyclopentyl-n-octyl group; 2-methoxycarbonylethyl group, 3-methoxycarbonyl-n-propyl
- R c6 and R c7 are ethyl group, n-propyl group, n-butyl group, n-pentyl group, 2-methoxyethyl group, 2-cyanoethyl group, 2-phenylethyl group, 2-cyclohexylethyl group, 2-methoxycarbonylethyl group, 2-chloroethyl group, 2-bromoethyl group, 3,3,3-trifluoropropyl group, and 3,3,4,4,5,5,5-hepta It is a fluoro-n-pentyl group.
- A is S because it is easy to obtain a photopolymerization initiator with excellent sensitivity.
- R c9 is a monovalent organic group, a halogen atom, a nitro group, or a cyano group.
- R c9 in formula (c5) is a monovalent organic group, it can be selected from various organic groups within the range that does not impede the object of the present invention.
- the organic group a carbon atom-containing group is preferable, and one or more carbon atoms and one or more atoms selected from the group consisting of H, O, S, Se, N, B, P, Si, and halogen atoms. A group consisting of is more preferred.
- the number of carbon atoms in the carbon atom-containing group is not particularly limited, and is preferably 1 or more and 50 or less, more preferably 1 or more and 20 or less.
- Preferred examples of the organic group represented by Rc9 in formula ( c5 ) include the same monovalent organic groups as Rc5 in formula (c3).
- R c9 substituted by a group selected from the group consisting of a benzoyl group; a naphthoyl group; an alkyl group having 1 to 6 carbon atoms, a morpholin-1-yl group, a piperazin-1-yl group, and a phenyl group; benzoyl group; nitro group; optionally substituted benzofuranylcarbonyl group is preferred, benzoyl group; naphthoyl group; 2-methylphenylcarbonyl group; 4-(piperazin-1-yl)phenylcarbonyl group a 4-(phenyl)phenylcarbonyl group is more preferred.
- n4 is preferably an integer of 0 or more and 3 or less, more preferably an integer of 0 or more and 2 or less, and particularly preferably 0 or 1.
- the position to which R c9 is bonded is preferably para to the bond to which the phenyl group to which R c9 is bonded is bonded to an oxygen atom or a sulfur atom.
- the monovalent organic group as Rc2 is not particularly limited as long as it does not impair the object of the present invention.
- a carbon atom-containing group is preferable, and one or more carbon atoms and one or more atoms selected from the group consisting of H, O, S, Se, N, B, P, Si, and halogen atoms. A group consisting of is more preferred.
- the number of carbon atoms in the carbon atom-containing group is not particularly limited, and is preferably 1 or more and 50 or less, more preferably 1 or more and 20 or less.
- Preferred examples of the monovalent organic group as Rc2 include the same monovalent organic groups as Rc5 in formula (c3).
- Rc2 is also preferably a cycloalkylalkyl group, a phenoxyalkyl group optionally having a substituent on the aromatic ring, and a phenylthioalkyl group optionally having a substituent on the aromatic ring.
- the substituents that the phenoxyalkyl group and the phenylthioalkyl group may have are those in which the phenyl group, the naphthyl group and the heterocyclyl group contained in R c5 in the formula (c3) further have a substituent. It is the same as the base.
- R c2 is a substituent containing the group represented by the above HX 2 C-- or H 2 XC--, an alkyl group, a cycloalkyl group, a phenyl group which may have a substituent, or A cycloalkylalkyl group and a phenylthioalkyl group optionally having a substituent on the aromatic ring are preferred.
- Alkyl group optionally substituted phenyl group, number of carbon atoms in cycloalkyl group contained in cycloalkylalkyl group, number of carbon atoms in alkylene group contained in cycloalkylalkyl group, cycloalkylalkyl group, aromatic Regarding the number of carbon atoms of the alkylene group contained in the phenylthioalkyl group optionally having substituents on the ring, or the phenylthioalkyl group optionally having substituents on the aromatic ring, the formula (c3 ) is the same as R c5 .
- A3 is a divalent organic group , preferably a divalent hydrocarbon group, preferably an alkylene group.
- A4 is a monovalent organic group, preferably a monovalent hydrocarbon group.
- the alkylene group may be linear or branched, preferably linear.
- the number of carbon atoms in the alkylene group is preferably 1 or more and 10 or less, more preferably 1 or more and 6 or less, and particularly preferably 1 or more and 4 or less.
- Preferable examples of A 4 include an alkyl group having 1 to 10 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, and an aromatic hydrocarbon group having 6 to 20 carbon atoms.
- Preferred specific examples of A4 include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group and n-hexyl.
- phenyl, naphthyl, benzyl, phenethyl, ⁇ -naphthylmethyl, and ⁇ -naphthylmethyl groups are examples of A4 that include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-
- Preferable specific examples of the group represented by -A 3 -CO-OA 4 include a 2-methoxycarbonylethyl group, a 2-ethoxycarbonylethyl group, a 2-n-propyloxycarbonylethyl group, a 2-n -butyloxycarbonylethyl group, 2-n-pentyloxycarbonylethyl group, 2-n-hexyloxycarbonylethyl group, 2-benzyloxycarbonylethyl group, 2-phenoxycarbonylethyl group, 3-methoxycarbonyl-n-propyl group, 3-ethoxycarbonyl-n-propyl group, 3-n-propyloxycarbonyl-n-propyl group, 3-n-butyloxycarbonyl-n-propyl group, 3-n-pentyloxycarbonyl-n-propyl group , 3-n-hexyloxycarbonyl-n-propyl group, 3-benzyloxycarbonyl-
- R c2 is also preferably a group represented by the following formula (c7) or (c8).
- R c10 and R c11 are each independently a monovalent organic group
- n5 is an integer of 0 or more and 4 or less
- R c10 and R c11 may combine with each other to form a ring
- R c12 is a monovalent organic group
- n6 is an integer of 1 or less and 8 or less
- n7 is an integer of 1 or more and 5 or less
- n8 is an integer from 0 to (n7+3).
- R c10 and R c11 in formula (c7) are the same as R c8 in formula (c4).
- R c10 includes a halogenated alkoxy group containing a group represented by HX 2 C-- or H 2 XC--, a halogenated alkyl group containing a group represented by HX 2 C-- or H 2 XC--, an alkyl group, or A phenyl group is preferred.
- the ring may be either an aromatic ring or an aliphatic ring.
- n7 is an integer of 0 or more and 4 or less, preferably 0 or 1, more preferably 0.
- R c12 is an organic group.
- the organic group include groups similar to the organic groups described for R c8 in formula (c4).
- alkyl groups are preferred.
- Alkyl groups may be straight or branched.
- the number of carbon atoms in the alkyl group is preferably 1 or more and 10 or less, more preferably 1 or more and 5 or less, and particularly preferably 1 or more and 3 or less.
- R c12 is preferably exemplified by a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, etc. Among these, a methyl group is more preferable.
- n7 is an integer of 1 or more and 5 or less, preferably an integer of 1 or more and 3 or less, and more preferably 1 or 2.
- n8 is 0 or more and (n7+3) or less, preferably an integer of 0 or more and 3 or less, more preferably 0 or more and 2 or less, and particularly preferably 0.
- n8 is an integer of 1 or more and 8 or less, preferably an integer of 1 or more and 5 or less, more preferably an integer of 1 or more and 3 or less, and particularly preferably 1 or 2.
- R c3 is a hydrogen atom, an optionally substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an optionally substituted aryl group.
- a phenyl group, a naphthyl group and the like are preferably exemplified as the substituent which may be possessed when R c3 is an aliphatic hydrocarbon group.
- R c3 is a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a 2-cyclopentylethyl group, a 2-cyclobutylethyl group, A cyclohexylmethyl group, a phenyl group, a benzyl group, a methylphenyl group, a naphthyl group and the like are preferably exemplified, and among these, a methyl group or a phenyl group is more preferable.
- Preferable specific examples of the compound represented by formula (c2) and having a group represented by formula (c5) as R c1 include the following compounds.
- a phosphine oxide compound is also preferable because the deep-part curability of the photocurable liquid composition is good.
- a phosphine oxide compound containing a partial structure represented by the following formula (c9) is preferable.
- R c21 and R c22 are each independently an alkyl group, a cycloalkyl group, an aryl group, an aliphatic acyl group having 2 to 20 carbon atoms, or an aromatic group having 7 to 20 carbon atoms. group acyl groups. However, both R c21 and R c22 are not aliphatic acyl groups or aromatic acyl groups.
- the number of carbon atoms in the alkyl groups of R c21 and R c22 is preferably 1 or more and 12 or less, more preferably 1 or more and 8 or less, and even more preferably 1 or more and 4 or less.
- the alkyl groups as R c21 and R c22 may be linear or branched.
- alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, tert- pentyl group, n-hexyl group, n-heptyl group, n-octyl group, 2,4,4-trimethylpentyl group, 2-ethylhexyl group, n-nonyl group, n-decyl group, n-undecyl group, and An n-dodecyl group can be mentioned.
- the number of carbon atoms in the cycloalkyl groups for R c21 and R c22 is preferably 5 or more and 12 or less.
- Specific examples of cycloalkyl groups include cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, and cyclododecyl groups.
- the number of carbon atoms in the aryl groups of R c21 and R c22 is preferably 6 or more and 12 or less.
- the aryl group may have a substituent. Examples of substituents include halogen atoms, alkyl groups having 1 to 4 carbon atoms, and alkoxy groups having 1 to 4 carbon atoms. Specific examples of aryl groups include phenyl and naphthyl groups.
- the number of carbon atoms in the aliphatic acyl groups for R c21 and R c22 is 2 or more and 20 or less, preferably 2 or more and 12 or less, more preferably 2 or more and 8 or less, and even more preferably 2 or more and 6 or less.
- Aliphatic acyl groups may be straight or branched. Specific examples of aliphatic acyl groups include acetyl, propionyl, butanoyl, pentanoyl, hexanoyl, heptanoyl, octanoyl, nonanoyl, decanoyl, undecanoyl, dodecanoyl, tridecanoyl, and tetradecanoyl groups. , pentadecanoyl, hexadecanoyl, heptadecanoyl, octadecanoyl, nonadecanoyl, and icosanoyl groups.
- the number of carbon atoms in the aromatic acyl groups for R c21 and R c22 is 7 or more and 20 or less.
- the aromatic acyl group may have a substituent.
- substituents include halogen atoms, alkyl groups having 1 to 4 carbon atoms, and alkoxy groups having 1 to 4 carbon atoms.
- Specific examples of aromatic acyl groups include benzoyl, o-tolyl, m-tolyl, p-tolyl, 2,6-dimethylbenzoyl, 2,6-dimethoxybenzoyl, 2,4,6- Examples include trimethylbenzoyl, ⁇ -naphthoyl, and ⁇ -naphthoyl groups.
- phosphine oxide compound containing the structural moiety represented by formula (c9) include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide, fin oxide, bis(2,6-dimethoxybenzoyl)-2,4,4-trimethyl-pentylphosphine oxide and the like.
- the content of the photopolymerization initiator (C) is 0.5% by mass or more and 30% by mass or less with respect to the mass (total solid content) of the photocurable liquid composition excluding the mass of the organic solvent (S) described later. is preferable, and 1% by mass or more and 20% by mass or less is more preferable.
- a photoinitiation aid may be combined with the photopolymerization initiator (C).
- Photoinitiation aids include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 4-dimethylaminobenzoate 2- ethylhexyl, 2-dimethylaminoethyl benzoate, N,N-dimethylp-toluidine, 4,4'-bis(dimethylamino)benzophenone, 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9, 10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 2-mercaptobenzimidazole, 2-mercapto
- the photocurable liquid composition contains an amine compound (D1) represented by the following formula (d1) and/or the following formula (d2 ) as the nitrogen-containing compound (D).
- NR d1 R d2 R d3 (d1) (In formula (d1), R d1 , R d2 and R d3 are each independently a hydrogen atom or an organic group.)
- R d4 ⁇ N CR d5 R d6 (d2) (In formula (d2), R d4 , R d5 and R d6 are each independently a hydrogen atom or an organic group.)
- R d1 , R d2 , R d3 , R d4 , R d5 , and R d6 are organic groups
- the organic groups are within a range that does not impair the desired effect. and can be selected from a variety of organic groups.
- a carbon atom-containing group is preferable, and one or more carbon atoms and one or more atoms selected from the group consisting of H, O, S, Se, N, B, P, Si, and halogen atoms.
- a group consisting of is more preferred.
- the number of carbon atoms in the carbon atom-containing group is not particularly limited, and is preferably 1 or more and 50 or less, more preferably 1 or more and 20 or less.
- Preferred examples of the organic group include an alkyl group, a cycloalkyl group, an optionally substituted phenyl group, an optionally substituted phenylalkyl group, an optionally substituted naphthyl group, An optionally substituted naphthylalkyl group, an optionally substituted heterocyclyl group, and the like can be mentioned.
- the number of carbon atoms in the alkyl group as the organic group is preferably 1 or more and 20 or less, more preferably 1 or more and 6 or less.
- the structure of the alkyl group may be linear or branched. Specific examples of alkyl groups include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group and isopentyl group.
- the alkyl group may contain an ether bond (--O--) in the carbon chain.
- alkyl groups having an ether bond in the carbon chain examples include methoxyethyl, ethoxyethyl, methoxyethoxyethyl, ethoxyethoxyethyl, propyloxyethoxyethyl, and methoxypropyl groups.
- the number of carbon atoms in the cycloalkyl group as the organic group is preferably 3 or more and 10 or less, more preferably 3 or more and 6 or less.
- Specific examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl groups.
- the number of carbon atoms in the phenylalkyl group as the organic group is preferably 7 or more and 20 or less, more preferably 7 or more and 10 or less.
- the number of carbon atoms in the naphthylalkyl group as the organic group is preferably 11 or more and 20 or less, more preferably 11 or more and 14 or less.
- Specific examples of phenylalkyl groups include benzyl, 2-phenylethyl, 3-phenylpropyl and 4-phenylbutyl groups.
- naphthylalkyl groups include ⁇ -naphthylmethyl, ⁇ -naphthylmethyl, 2-( ⁇ -naphthyl)ethyl, and 2-( ⁇ -naphthyl)ethyl groups.
- the phenylalkyl group or naphthylalkyl group may further have a substituent on the phenyl group or naphthyl group.
- the heterocyclyl group is the same as when R c4 in formula (c3) is a heterocyclyl group, and the heterocyclyl group may further have a substituent.
- a heterocyclyl group as an organic group may be an aliphatic heterocyclic group or an aromatic heterocyclic group.
- the heterocyclyl group is preferably a 5- or 6-membered monocyclic ring containing one or more N, S, or O, or a heterocyclyl group in which such monocyclic rings are condensed with each other or such monocyclic rings and a benzene ring are condensed.
- the heterocyclyl group is a condensed ring, the number of monocyclic rings constituting the condensed ring shall be up to 3.
- Heterocyclic rings constituting such heterocyclyl groups include furan, thiophene, pyrrole, oxazole, isoxazole, thiazole, thiadiazole, isothiazole, imidazole, pyrazole, triazole, pyridine, pyrazine, pyrimidine, pyridazine, benzofuran, benzothiophene, indole, isoindole, indolizine, benzimidazole, benzotriazole, benzoxazole, benzothiazole, carbazole, purine, quinoline, isoquinoline, quinazoline, phthalazine, cinnoline, quinoxaline, piperidine, piperazine, morpholine, piperidine, tetrahydropyran, and tetrahydrofuran; be done.
- the substituent may be an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms.
- a halogenated alkyl group having 1 to 6 carbon atoms a halogenated alkoxy group having 1 to 6 carbon atoms
- a saturated aliphatic acyl group having 2 to 7 carbon atoms a saturated aliphatic acyl group having 2 to 7 carbon atoms
- alkoxycarbonyl group saturated aliphatic acyloxy group having 2 to 7 carbon atoms
- monoalkylamino group having alkyl group having 1 to 6 carbon atoms dialkylamino group having alkyl group having 1 to 6 carbon atoms
- a benzoyl group a halogen atom, a nitro group, a cyano group, and the like.
- the number of substituents is not particularly limited, and is preferably from 1 to 4.
- the phenyl group, naphthyl group and heterocyclyl group contained in the organic group have multiple substituents, the multiple substituents may be the same or different.
- R d1 , R d2 and R d3 in the formula (d1) are preferably each independently a hydrogen atom or an organic group, and R d1 , R d2 , and at least one of R d3 is preferably an aromatic group-containing group.
- R d4 , R d5 and R d6 are each independently a hydrogen atom or an organic group, and R d4 , R d5 and At least one of R d6 is preferably an aromatic group-containing group.
- the aromatic ring in the aromatic group-containing group may be either an aromatic hydrocarbon ring or an aromatic heterocyclic ring.
- a hydrocarbon group is preferred as the aromatic group-containing group.
- an aromatic hydrocarbon group (aryl group) and an aralkyl group are preferable.
- Aromatic hydrocarbon groups include phenyl, naphthalene-1-yl, and naphthalene-2-yl groups. Among these aromatic hydrocarbon groups, a phenyl group is preferred.
- Aralkyl groups include benzyl, 2-phenylethyl, 3-phenylpropyl, and 4-phenylbutyl groups.
- R d1 , R d2 and R d3 is preferably a group represented by Ar d1 —CH 2 —.
- R d4 is preferably a group represented by Ar d1 —CH 2 —.
- Ar d1 is an aromatic group optionally having a substituent.
- the aromatic group as Ar d1 may be an aromatic hydrocarbon group or an aromatic heterocyclic group.
- the aromatic group for Ar d1 is preferably an aromatic hydrocarbon group.
- Aromatic hydrocarbon groups include phenyl, naphthalene-1-yl, and naphthalene-2-yl groups. Among these aromatic hydrocarbon groups, a phenyl group is preferred.
- the substituents that the aromatic group as Ar d1 may have include the organic groups as R d1 , R d2 , R d3 , R d4 , R d5 and R d6 being phenyl group, naphthyl group and heterocyclyl group. In some cases, it is the same as the substituents these groups may have.
- amine compound represented by formula (d1) include triphenylamine, N,N-diphenylbenzylamine, N-phenyldibenzylamine, tribendialumine, N,N-dimethylphenylamine, N -methyldiphenylamine, N,N-dimethylbenzylamine, N-methyldibenzylamine, N-methyl-N-benzylphenylamine, N,N-diethylphenylamine, N-ethyldiphenylamine, N,N-diethylbenzylamine, N-ethyldibenzylamine, and N-ethyl-N-benzylphenylamine.
- imine compounds represented by formula (d2) include N-benzylphenylmethanimine, N-benzyldiphenylmethanimine, N-benzyl-1-phenylethanimine, and N-benzylpropane-2-imine. is mentioned.
- the content of the nitrogen-containing compound in the photocurable liquid composition is not particularly limited as long as the desired effects are not impaired.
- the content of the nitrogen-containing compound (D) is preferably 5% by mass or more and 25% by mass or less, more preferably 7% by mass or more and 20% by mass or less, relative to the mass of the photopolymerizable monomer (A).
- the photocurable liquid composition may contain a plasticizer (E).
- the plasticizer (E) is a component that lowers the viscosity of the photocurable liquid composition without significantly impairing the curability of the photocurable liquid composition or the refractive index of the cured product.
- a compound represented by the following formula (e-1) is preferable as the plasticizer (E).
- R e1 -R e3 r -X e -R e4 s -R e2 (e-1) (In formula (e-1), R e1 and R e2 are each independently a phenyl group optionally having 1 to 5 substituents, and the substituents have 1 to 4 carbon atoms.
- R e3 and R e4 are each independently a methylene group or an ethane-1,2-diyl group; , and s are each independently 0 or 1, and X e is an oxygen atom or a sulfur atom.
- the viscosity of the photocurable liquid composition is lowered without significantly impairing the curability of the photocurable liquid composition or the refractive index of the cured product. be done.
- the viscosity of the plasticizer (E) measured by an E-type viscometer at 25° C. is preferably 10 cP or less, more preferably 8 cP or less, and further preferably 6 cP or less. preferable.
- the boiling point of the plasticizer (E) under atmospheric pressure is 250° C. or higher. is preferred, and 260° C. or higher is more preferred.
- the upper limit of the boiling point of the plasticizer (E) under atmospheric pressure is not particularly limited.
- R e1 and R e2 in formula (e-1) are each independently a phenyl group optionally having 1 to 5 substituents.
- the substituent bonded to the phenyl group is a group selected from an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, and a halogen atom.
- the number of substituents is not particularly limited. The number of substituents is 1 or more and 5 or less, preferably 1 or 2, and preferably 1. From the viewpoint of lowering the viscosity of the photocurable liquid composition, it is preferable that each of R e1 and R e2 is an unsubstituted phenyl group.
- alkyl group having 1 to 4 carbon atoms as a substituent examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group and tert-butyl group. mentioned.
- alkoxy groups having 1 to 4 carbon atoms as substituents include methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, isobutyloxy, sec-butyloxy, and tert- A butyloxy group is mentioned.
- a halogen atom as a substituent includes a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
- R e3 and R e4 in formula (e-1) are each independently a methylene group or an ethane-1,2-diyl group. Moreover, r and s are 0 or 1 each independently.
- X e in formula (e-1) is an oxygen atom or a sulfur atom.
- Preferred specific examples of the compound represented by formula (e-1) described above include diphenyl ether, diphenyl sulfide, dibenzyl ether, dibenzyl sulfide, diphenethyl ether, and diphenethyl sulfide. Among these, diphenyl sulfide and/or dibenzyl ether are more preferred.
- the content of the plasticizer (E) in the photocurable liquid composition is determined with respect to the mass of the entire photocurable liquid composition in terms of both viscosity adjustment and dispersibility of the metal oxide nanoparticles (B). , more than 0% by mass and 35% by mass or less, and more preferably 5% by mass or more and 15% by mass or less.
- the photocurable liquid composition may contain a solvent (S) of 5 mass % or less based on the mass of the photocurable liquid composition.
- a solvent (S) of 5 mass % or less based on the mass of the photocurable liquid composition.
- the type of solvent (S) is not particularly limited, it is typically an organic solvent.
- Organic solvents that can be blended in the photocurable liquid composition include, for example, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol-n-propyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol monomethyl ether, diethylene glycol mono Ethyl ether, diethylene glycol mono-n-propyl ether, diethylene glycol mono-n-butyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n-propyl ether , propylene glycol mono-n-butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol mono-n-propyl ether, dipropylene glycol mono-n-butyl ether, tripropylene glycol
- the photocurable liquid composition may contain various additives conventionally blended in photosensitive compositions and ink compositions, as long as the objects of the present invention are not hindered. good.
- Preferable additives to be added to the photocurable liquid composition include dispersants, adhesion promoters such as silane coupling agents, antioxidants, aggregation inhibitors, antifoaming agents, surfactants and the like.
- the surfactant is not particularly limited, and known components such as fluorine-based surfactants and silicon-based surfactants can be used.
- a photocurable liquid composition is obtained by mixing predetermined amounts of the components described above and then uniformly stirring the mixture.
- the photocurable liquid composition described above is typically Molding the photocurable liquid composition according to the shape of the cured product to be formed; exposing the shaped photocurable liquid composition; A cured product is obtained by a method comprising
- the cured product produced by the above method exhibits a high refractive index of, for example, preferably 1.60 or higher, more preferably 1.64 or higher, and even more preferably 1.66 or higher, at a wavelength of 550 nm. Therefore, the cured product produced by the above method is suitably used in optical applications requiring a high refractive index.
- a film made of a cured product of the photocurable liquid composition described above is suitably used as a high refractive index film constituting an antireflection film or the like in various display panels such as an organic EL display panel and a liquid crystal display panel. be.
- the film thickness of the high refractive index film made of the cured product of the photocurable liquid composition described above is not particularly limited, and is appropriately selected according to the application.
- the film thickness of the high refractive index film is typically preferably 1 nm or more and 20 ⁇ m or less, more preferably 50 nm or more and 10 ⁇ m or less.
- the method for molding the photocurable liquid composition is not particularly limited, and is appropriately selected according to the shape of the cured product.
- the shape of the cured product includes, but is not limited to, a film shape, a lens shape, a line shape, a prism shape, and the like. Among these shapes, the membrane shape is preferred.
- the method for molding the photocurable liquid composition is not particularly limited.
- the shape of the cured product is lens-shaped, prism-shaped, or the like
- the photocurable liquid composition may be filled into a mold corresponding to the shape of the cured product using a squeegee or the like.
- the shape of the cured product is a line shape or the like, the photocurable liquid composition may be applied onto the substrate according to the shape of the cured product.
- the application method includes, for example, a printing method such as an inkjet method.
- a printing method such as an inkjet method.
- a method for applying the cured product in a film shape there are methods using a contact transfer type coating device such as a roll coater, a reverse coater and a bar coater, and a method using a non-contact type coating device such as a spinner (rotary coating device) and a curtain flow coater. mentioned.
- the photocurable liquid composition can be applied in a film shape by a printing method such as an inkjet method.
- the solvent (S) is removed from the molded photocurable liquid composition by a method such as heating. may be removed.
- a photocurable liquid composition molded into a desired shape such as a film shape is exposed to light to such an extent that the photocurable liquid composition is not completely cured, and then a method such as an imprint method is used.
- a method such as an imprint method is used.
- the above-mentioned photocurable liquid composition is applied to a 3D printing method, and by repeating inkjet printing and curing by exposure to laminate a thin film-like cured product, a cured product having a desired shape is formed. You may
- Exposure to the molded photocurable liquid composition is performed by irradiating active energy rays such as ultraviolet rays and excimer laser light.
- Exposure to the shaped photocurable liquid composition may be performed regioselectively, for example, by a method such as exposure through a mask.
- a patterned cured product can be formed by developing the exposed photocurable liquid composition using an organic solvent to remove the unexposed areas.
- development processing it is preferable to sufficiently remove the developer by a method such as drying by heating after development.
- a cured product having a desired shape and a high refractive index is formed using the photocurable liquid composition containing no or only a small amount of the solvent (S).
- zirconium oxide particles B1 (average particle size 8 nm) surface-modified using 3-methacryloxypropyltrimethoxysilane as a capping agent
- ethylenically unsaturated Zirconium oxide particles B2 (average particle size 10 nm) not surface-modified with a saturated double bond-containing group capping agent
- titanium oxide particles B3 (average particle size diameter 11 nm)
- titanium oxide particles B4 average particle diameter 10 nm
- Zirconium oxide particles B2 were obtained by drying nanocrystals collected by centrifugation according to the method described in paragraph [0223] of JP-A-2018-193481.
- the mass of the capping agent is 0.8 to 1.5 times the mass of the zirconium oxide particles.
- Zirconium oxide particles B2 were obtained in the same manner as the zirconium oxide particles B2, except that 3-methacryloxypropyltrimethoxysilane was further added. Obtained by drying nanocrystals recovered by centrifugation, following the method described in Example 8 of WO2020/106860 for titanium oxide particles B4.
- titanium oxide particles B3 surface-modified with 3-methacryloxypropyltrimethoxysilane in the step of adding the capping agent, 50% by mass of the total amount of the capping agent was replaced with 3-methacryloxypropyltrimethoxysilane. , obtained in the same manner as titanium oxide particles B4.
- a photocurable liquid composition of Comparative Example 1 was obtained in the same manner as in Examples 1 to 4, except that the nitrogen-containing compound (D) was not used.
- Tables 1 and 2 show the viscosities of the obtained photocurable liquid compositions measured at 25° C. using an E-type viscometer. Further, the refractive index, light transmittance, haze and yellowness index (Y.I.) of the cured film formed using the obtained photocurable liquid composition were measured according to the following recipe. These measurement results are shown in Tables 1 and 2. Furthermore, according to the following recipe, the thickness T1 of the layer rich in each metal oxide nanoparticle in the cured film formed using the photocurable liquid composition and the thickness of the layer in which each metal oxide nanoparticle is almost absent The ratio T1/T2 with respect to T2 was measured. The smaller the value of T1/T2, the more suppressed the localization of each metal oxide nanoparticle in the cured film.
- ⁇ Refractive index measurement method The photocurable liquid composition of each example and comparative example was applied onto a glass substrate using an inkjet device. Then, using a 395 nm UV-LED exposure machine, the coating film was exposed with an exposure amount of 2 J/cm 2 and cured to obtain a cured film with a thickness of 3 ⁇ m. The refractive index of the film at a light wavelength of 550 nm was determined using a Metricon prism coupler.
- ⁇ Total light transmittance, haze, and Y. I. measurement method> After applying the photocurable liquid composition of each example and comparative example by spin coating on a glass substrate, using a 385 nm UV-LED exposure machine, the coating film is exposed at an exposure amount of 2 J / cm 2 and cured. to obtain a cured film having a thickness of 10 ⁇ m.
- the membrane was purchased from Hunter Associates Laboratory, Inc.; Total light transmittance, haze, and Y.E.M. I. was measured.
- T1/T2 measurement> The refractive index of each cured film was measured by a prism coupling method using a prism coupler 2010/M manufactured by Metricon for a cured film obtained under the same conditions as the cured film to be measured for refractive index.
- each of the two layers was analyzed to obtain a thickness value for each layer.
- the thickness of the upper layer rich in zirconium oxide microparticles was defined as T1
- the thickness of the lower layer containing less zirconium oxide microparticles was defined as T2. From T1 and T2 thus obtained, the thickness ratio of each layer was calculated as T1/T2.
- the value of T1/T2 was used as an evaluation index for the degree of two-layer formation.
- the photocurable liquid composition containing the photopolymerizable monomer (A), the metal oxide nanoparticles (B), and the photopolymerization initiator (C) was added to By blending the nitrogen-containing compound (D) that satisfies the requirements, the value of T1/T2 is lowered, and localization of the metal oxide nanoparticles (B) in the cured product is suppressed. Moreover, the surface of the metal oxide nanoparticles (B) modified with an ethylenically unsaturated double bond-containing group has a better refractive index, total light transmittance, haze, or Y.O. I. It can be seen that the various optical properties are equivalent or superior. Moreover, when the metal oxide nanoparticles (B) contain titanium oxide nanoparticles, when the nitrogen-containing compound (D) is tribenzylamine, it can be seen that the various optical properties described above are excellent.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Inorganic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
このような高屈折材料を形成するための組成物として、特定の粒子径の金属酸化物(A)と、(メタ)アクリレート(B)と、光重合開始剤(C)とを含有するエネルギー線硬化性組成物が提案されている(特許文献1参照)。
より具体的には、特許文献1に記載される組成物を硬化させて、硬化膜を形成する場合、硬化膜の内部で、金属酸化物(A)がリッチな層と、金属酸化物(A)をほとんど含まない層とに相分離しやすい。
光重合性モノマー(A)が、エチレン性不飽和二重結合を有し、
含窒素化合物(D)が、下記式(d1):
NRd1Rd2Rd3・・・(d1)
(式(d1)中、Rd1、Rd2、及びRd3は、それぞれ独立に水素原子、又は有機基である。)
で表されるアミン化合物(D1)、及び、下記式(d2)
Rd3-N=CRd4Rd5・・・(d2)
(式(d2)中、Rd3、Rd4、及びRd5は、それぞれ独立に水素原子、又は有機基である。)
で表されるイミン化合物(D2)からなる群より選択される少なくとも1種である、光硬化性液状組成物である。
成形された光硬化性液状組成物に対して露光することと、を含む硬化物の製造方法である。
光硬化性液状組成物は、光重合性モノマー(A)と、金属酸化物ナノ粒子(B)と、光重合開始剤(C)と、含窒素化合物(D)を含む。
光重合性モノマー(A)は、エチレン性不飽和二重結合を有する。
含窒素化合物(D)は、下記式(d1):
NRd1Rd2Rd3・・・(d1)
(式(d1)中、Rd1、Rd2、及びRd3は、それぞれ独立に水素原子、又は有機基である。)
で表されるアミン化合物(D1)、及び、下記式(d2)
Rd3-N=CRd4Rd5・・・(d2)
(式(d2)中、Rd3、Rd4、及びRd5は、それぞれ独立に水素原子、又は有機基である。)
で表されるイミン化合物(D2)からなる群より選択される少なくとも1種である。
光重合性モノマー(A)と、金属酸化物ナノ粒子(B)と、光重合開始剤(C)とを含む光硬化性液状組成物に、上記の含窒素化合物(D)を含有させることにより、光硬化性液状組成物の硬化物における金属酸化物ナノ粒子(B)の局在が抑制される。
光硬化性液状組成物の溶媒(S)の含有量は、5質量%以下が好ましく、3質量%以下がより好ましく、2質量%以下がさらに好ましく、1質量%以下がさらにより好ましく、0.5質量%以下が特に好ましく、0.3質量%以下が最も好ましい。光硬化性液状組成物における溶媒(S)の含有量の下限値は特になく、0質量%以上が好ましい。
光硬化性液状組成物は、溶媒(S)を実質的に含まないのがとりわけ好ましい。光硬化性液状組成物が溶媒(S)を実質的に含まないとは、原料等に付随してごく少量の溶媒(S)が不可避的に光硬化性液状組成物に持ち込まれる他、光硬化性液状組成物に意図的に溶媒(S)が加えられていないことを言う。
光硬化性液状組成物が溶媒(S)を実質的に含まない場合の、光硬化性液状組成物の溶媒(S)の含有量は、例えば0.2質量%以下であり、0.15質量%以下が好ましく、0.1質量%以下がより好ましく、0.05質量%以下がさらに好ましい。
光硬化性液状組成物の粘度は、例えば、可塑剤(E)の含有量を調整したり、光重合性モノマー(A)や金属化合物粒子(B)の含有量を調整したり、光硬化性液状組成物に少量の溶媒(S)を加えること等によって調整することができる。
光硬化性液状組成物は、エチレン性不飽和二重結合を有する光重合性モノマー(A)を含む。
光硬化性液状樹脂組成物を用いて、機械的特性に優れる硬化物を形成しやすく、また光硬化性液状樹脂組成物が硬化性に優れる点で、光重合性モノマー(A)は、2以上のエチレン性不飽和二重結合を有する多官能モノマー(A1)を含むことが好ましい。
光重合性モノマー(A)としては、特に限定されず、従来公知の多官能モノマー(A1)や単官能モノマー(A2)を用いることができる。
(式(A1)、及び式(A2)中、MAは、それぞれ独立に、(メタ)アクリロイル基であり、Xは、それぞれ独立に、酸素原子、-NH-、又は-N(CH3)-であり、Ra1は、それぞれ独立に、エタン-1,2-ジイル基、プロパン-1,2-ジイル基、又はプロパン-1,3-ジイル基であり、Ra2は、水酸基、炭素原子数1以上4以下のアルキル基、又は-X-(Ra1-O)na1-MAで表される基であり(Xは前記と同様であり)、na1、及びna2は、それぞれ独立に、0又は1である。)
1)(MA-NH-CH2)4-C
2)(MA-N(CH3)-CH2)4-C
3)(MA-O-CH2CH2CH2-O-CH2)4-C
4)(MA-O-CH2CH2-O-CH2)4-C
5)(MA-O-CH2CH2CH2-NH-CH2)4-C
6)(MA-O-CH2CH2-NH-CH2)4-C
7)(MA-O-CH2CH2CH2-N(CH3)-CH2)4-C
8)(MA-O-CH2CH2-N(CH3)-CH2)4-C
9)(MA-NH-CH2)3-C-CH2-O-CH2-C-(CH2-NH-MA)3
10)(MA-N(CH3)-CH2)3-C-CH2-O-CH2-C-(CH2-N(CH3)-MA)3
11)(MA-O-CH2CH2CH2-O-CH2)3-C-CH2-O-CH2-C-(CH2-O-CH2CH2CH2-O-MA)3
12)(MA-O-CH2CH2-O-CH2)3-C-CH2-O-CH2-C-(CH2-O-CH2CH2-O-MA)3
13)(MA-O-CH2CH2CH2-NH-CH2)3-C-CH2-O-CH2-C-(CH2-NH-CH2CH2CH2-O-MA)3
14)(MA-O-CH2CH2-NH-CH2)3-C-CH2-O-CH2-C-(CH2-NH-CH2CH2-O-MA)3
15)(MA-O-CH2CH2CH2-N(CH3)-CH2)3-C-CH2-O-CH2-C-(CH2-N(CH3)-CH2CH2CH2-O-MA)3
16)(MA-O-CH2CH2-N(CH3)-CH2)3-C-CH2-O-CH2-C-(CH2-N(CH3)-CH2CH2-O-MA)3
17)(MA-NH-CH2)2-CH-NH-MA
18)(MA-N(CH3)-CH2)2-CH-N(CH3)-MA
19)(MA-O-CH2CH2CH2-O-CH2)2-CH-O-CH2CH2CH2-O-MA
20)(MA-O-CH2CH2-O-CH2)2-CH-C-O-CH2CH2-O-MA
21)(MA-O-CH2CH2CH2-NH-CH2)2-CH-NH-CH2CH2CH2-O-MA
22)(MA-O-CH2CH2-NH-CH2)2-CH2-NH-CH2CH2-O-MA
23)(MA-O-CH2CH2CH2-N(CH3)-CH2)2-CH2-N(CH3)-CH2CH2CH2-O-MA
24)(MA-O-CH2CH2-N(CH3)-CH2)2-CH2-N(CH3)-CH2CH2-O-MA
25)(MA-NH-CH2)3-C-CH2CH3
26)(MA-N(CH3)-CH2)3-C-CH2CH3
27)(MA-O-CH2CH2CH2-O-CH2)3-C-CH2CH3
28)(MA-O-CH2CH2-O-CH2)3-C-CH2CH3
29)(MA-O-CH2CH2CH2-NH-CH2)3-C-CH2CH3
30)(MA-O-CH2CH2-NH-CH2)3-C-CH2CH3
31)(MA-O-CH2CH2CH2-N(CH3)-CH2)3-C-CH2CH3
32)(MA-O-CH2CH2-N(CH3)-CH2)3-C-CH2CH3
Ara1-Ra01-S-Ra02-O-CO-CRa03=CH2・・・(A3)
(式(A1)中、Ara1は、ハロゲン原子で置換されていてもよいフェニル基であり、Ra01は、単結合、又は炭素原子数1以上6以下のアルキレン基であり、Ra02は、炭素原子数1以上6以下のアルキレン基であり、Ra03は、水素原子、又はメチル基である。)
で表される化合物である。
Ara1としては、無置換のフェニル基が好ましい。
Ra01としては、単結合、及びメチレン基が好ましく、単結合がより好ましい。
Ra02としては、メチレン基、エタン-1,2-ジイル基、及びプロパン-1,3-ジイル基が好ましく、エタン-1,2-ジイル基、及びプロパン-1,3-ジイル基がより好ましい。
式(A3)で表される含硫黄(メタ)アクリレートは、1種を単独で用いてもよく、2種以上を組み合わせて用いてもよい。
光硬化性液状組成物は、金属酸化物ナノ粒子(B)を含む。金属酸化物ナノ粒子を構成する金属酸化物の種類は、所望する効果が損なわれない限り特に限定されない。金属酸化物ナノ粒子(B)の好ましい例としては、酸化ジルコニウムナノ粒子、酸化チタンナノ粒子、チタン酸バリウムナノ粒子、及び酸化セリウムナノ粒子からなる群より選択される少なくとも1種が挙げられる。光硬化性液状組成物は、これらの金属酸化物ナノ粒子(B)のうちの1種を単独で含んでもよく、2種以上を組み合わせて含んでいてもよい。
光硬化性液状組成物が、上記の金属酸化物ナノ粒子(B)を含むことにより高屈折率を示す硬化物を形成できる。
金属酸化物ナノ粒子(B)の表面がエチレン性不飽和二重結合含有基で修飾されている場合、硬化物を形成する際に、光重合性モノマー(A)が金属酸化物ナノ粒子(B)とともに重合しつつ、金属酸化物ナノ粒子(B)が光重合性モノマー(A)の重合体からなるマトリックス中に固定される。これにより金属酸化物ナノ粒子(B)の凝集が起こりにくくい。このため、金属酸化物ナノ粒子(B)の表面がエチレン性不飽和二重結合含有基で修飾されていると、硬化物における金属酸化物ナノ粒子(B)の局在を特に抑制しやすい。
キャッピング剤が有する反応性基の好ましい例としては、トリメトキシシリル基、トリエトキシリル基等のトリアルコキシシリル基;ジメトキシシリル基、ジエトキシシリル基等のジアルコキシシリル基;モノメトキシシリル基、モノエトキシシリル基等のモノアルコキシシリル基;トリクロロシリル基等のトリハロシリル基;ジクロロシリル基等のジハロシリル基;モノクロロシリル基等のモノハロシリル基;カルボキシ基;クロロカルボニル基等のハロカルボニル基;水酸基;ホスホノ基(-P(=O)(OH)2);ホスフェート基(-O-P(=O)(OH)2)が挙げられる。
カルボキシ基、及びハロカルボニル基は、金属酸化物ナノ粒子(B)の表面と、(金属酸化物-O-CO-)で表される結合を形成する。
水酸基は、金属酸化物ナノ粒子(B)の表面と、(金属酸化物-O-)で表される結合を形成する。
ホスホノ基、及びホスフェート基は、金属酸化物ナノ粒子(B)の表面と、(金属酸化物-O-P(=O)<)で表される結合を形成する。
上記の反応性基に結合する基としては、例えば、直鎖状でも分岐鎖状であってもよく、酸素原子(-O-)で中断されていてもよいアルキル基、直鎖状でも分岐鎖状であってもよく、酸素原子(-O-)で中断されていてもよいアルケニル基、直鎖状であっても分岐鎖状であってもよく、酸素原子(-O-)で中断されていてもよいアルキニル基、シクロアルキル基、芳香族炭化水素基、及び複素環基等が挙げられる。
これらの基は、ハロゲン原子、グリシジル基等のエポキシ基含有基、水酸基、メルカプト基、アミノ基、(メタ)アクリロイル基、及びイソシアネート基等の置換基で置換されていてもよい。また、置換基の数は特に限定されない。
上記式中Rb5としては、例えば、-Si(CH3)3、-Si(CH3)2H、-Si(CH3)2(CH=CH2)、及び-Si(CH3)2(CH2CH2CH2CH3)等の末端基が挙げられる。
上記式中のr及びsは、それぞれ独立に0以上60以下の整数である。上記式中のr及びsは双方が0であることはない。
硬化物をより高屈折化させるためには、40質量%以上93質量%以下が好ましい。
光硬化性液状組成物中の金属酸化物ナノ粒子(B)の含有量が上記の範囲内であることにより、硬化物における金属酸化物ナノ粒子(B)の局在を抑制しつつ、高屈折率の硬化物を形成しやすい。
なお、金属酸化物ナノ粒子(B)の表面に、エチレン性不飽和二重結合含有基で修飾されている場合、金属酸化物ナノ粒子(B)の表面に存在するエチレン性不飽和二重結合含有基を有するキャッピング剤の質量を、金属酸化物ナノ粒子(B)の質量に含める。
光重合開始剤(C)としては、特に限定されず、従来公知の光重合開始剤を用いることができる。
オキシムエステル化合物としては、下記式(c1)で表される部分構造を有する化合物が好ましい。
n1は、0、又は1であり、
Rc2は、一価の有機基であり、
Rc3は、水素原子、置換基を有してもよい炭素原子数1以上20以下の脂肪族炭化水素基、又は置換基を有してもよいアリール基であり、
*は結合手である。)
式(c1)で表される部分構造を有する化合物は、式(c1)で表される部分構造を1つ又は2つ有することが好ましい。
n1は、0、又は1であり、
Rc2は、一価の有機基であり、
Rc3は、水素原子、置換基を有してもよい炭素原子数1以上20以下の脂肪族炭化水素基、又は置換基を有してもよいアリール基である。)
n2は、0以上3以下の整数であり、
n2が2又は3の場合、複数のRc5は同一でも異なっていてもよく、複数のRc5は互いに結合して環を形成してもよい。
*は結合手である。)
Rc6とRc7とは互いに結合して環を形成してもよく、
Rc7とフルオレン骨格中のベンゼン環とが互いに結合して環を形成してもよく、
Rc8は、ニトロ基、又は1価の有機基、であり、
n3は、0以上4以下の整数であり、
*は結合手である。)
Rc4の好適な例としては、炭素原子数1以上20以下の置換基を有してもよいアルキル基、炭素原子数3以上20以下の置換基を有してもよいシクロアルキル基、炭素原子数2以上20以下の置換基を有してもよい飽和脂肪族アシル基、炭素原子数2以上20以下の置換基を有してもよいアルコキシカルボニル基、置換基を有してもよいフェニル基、置換基を有してもよいベンゾイル基、置換基を有してもよいフェノキシカルボニル基、置換基を有してもよい炭素原子数7以上20以下のフェニルアルキル基、置換基を有してもよいナフチル基、置換基を有してもよいナフトイル基、置換基を有してもよいナフトキシカルボニル基、置換基を有してもよい炭素原子数11以上20以下のナフチルアルキル基、置換基を有してもよいヘテロシクリル基、及び置換基を有してもよいヘテロシクリルカルボニル基等が挙げられる。
Rc4がヘテロシクリル基である場合、当該ヘテロシクリル基が有していてもよい置換基としては、水酸基、炭素原子数1以上6以下のアルコキシ基、ハロゲン原子、シアノ基、ニトロ基等が挙げられる。
また、硬化性組成物中での式(c3)で表される化合物の溶解性が良好である点から、n-オクチル基、及び2-エチルヘキシル基が好ましく、2-エチルヘキシル基がより好ましい。
Rc5として好適な1価の有機基の例としては、アルキル基、アルコキシ基、シクロアルキル基、シクロアルコキシ基、飽和脂肪族アシル基、アルコキシカルボニル基、飽和脂肪族アシルオキシ基、置換基を有してもよいフェニル基、置換基を有してもよいフェノキシ基、置換基を有してもよいベンゾイル基、置換基を有してもよいフェノキシカルボニル基、置換基を有してもよいベンゾイルオキシ基、置換基を有してもよいフェニルアルキル基、置換基を有してもよいナフチル基、置換基を有してもよいナフトキシ基、置換基を有してもよいナフトイル基、置換基を有してもよいナフトキシカルボニル基、置換基を有してもよいナフトイルオキシ基、置換基を有してもよいナフチルアルキル基、置換基を有してもよいヘテロシクリル基、置換基を有してもよいヘテロシクリルカルボニル基、1、2の有機基で置換されたアミノ基、モルホリン-1-イル基、ピペラジン-1-イル基、ハロゲン、ニトロ基、シアノ基、HX2C-又はH2XC-で表される基を含む置換基(ただし、Xは、各々独立に、ハロゲン原子である)等が挙げられる。
Rc5がヘテロシクリルカルボニル基である場合、ヘテロシクリルカルボニル基に含まれるヘテロシクリル基は、Rc5がヘテロシクリル基である場合と同様である。
Rc8が1価の有機基である場合の好適な例としては、式(c3)中のRc5としての1価の有機基の好適な例と同様の基が挙げられる。
式(c5)におけるRc9が1価の有機基である場合、本発明の目的を阻害しない範囲で、種々の有機基から選択できる。有機基としては、炭素原子含有基が好ましく、1以上の炭素原子と、H、O、S、Se、N、B、P、Si、及びハロゲン原子からなる群より選択される1以上の原子とからなる基がより好ましい。炭素原子含有基の炭素原子数は特に限定されず、1以上50以下が好ましく、1以上20以下がより好ましい。
式(c5)においてRc9が有機基である場合の好適な例としては、式(c3)中のRc5としての1価の有機基と同様の基が挙げられる。
Rc2としての1価の有機基の好適な例としては、式(c3)中のRc5としての1価の有機基と同様の基が挙げられる。これらの基の具体例は、式(c3)中のRc5について説明した基と同様である。
また、Rc2としてはシクロアルキルアルキル基、芳香環上に置換基を有していてもよいフェノキシアルキル基、芳香環上に置換基を有していてもよいフェニルチオアルキル基、も好ましい。フェノキシアルキル基、及びフェニルチオアルキル基が有していてもよい置換基は、式(c3)中のRc5に含まれる、フェニル基、ナフチル基、及びヘテロシクリル基がさらに置換基を有する場合の置換基と同様である。
n5は0以上4以下の整数であり、
Rc10及びRc11がベンゼン環上の隣接する位置に存在する場合、Rc10とRc11とが互いに結合して環を形成してもよく、
Rc12は、1価の有機基であり、
n6は1以下8以下の整数であり、
n7は1以上5以下の整数であり、
n8は0以上(n7+3)以下の整数である。)
上記式(c7)中、n7は0以上4以下の整数であり、0又は1であるのが好ましく、0であるのがより好ましい。
上記式(c8)中、n8は1以上8以下の整数であり、1以上5以下の整数が好ましく、1以上3以下の整数がより好ましく、1又は2が特に好ましい。
アルキル基の具体例としては、メチル基、エチル基、n-プロピル基、イソプロピル基、n-ブチル基、イソブチル基、sec-ブチル基、tert-ブチル基、n-ペンチル基、イソペンチル基、tert-ペンチル基、n-ヘキシル基、n-ヘプチル基、n-オクチル基、2,4,4,-トリメチルペンチル基、2-エチルヘキシル基、n-ノニル基、n-デシル基、n-ウンデシル基、及びn-ドデシル基が挙げられる。
脂肪族アシル基の具体例としては、アセチル基、プロピオニル基、ブタノイル基、ペンタノイル基、ヘキサノイル基、ヘプタノイル基、オクタノイル基、ノナノイル基、デカノイル基、ウンデカノイル基、ドデカノイル基、トリデカノイル基、テトラデカノイル基、ペンタデカノイル基、ヘキサデカノイル基、ヘプタデカノイル基、オクタデカノイル基、ノナデカノイル基、及びイコサノイル基が挙げられる。
硬化物における金属酸化物ナノ粒子(B)の局在を抑制する目的で、光硬化性液状組成物は、下記式(d1)で表されるアミン化合物(D1)、及び/又は下記式(d2)で表されるイミン化合物(D2)を、含窒素化合物(D)として含んでいてもよい。
NRd1Rd2Rd3・・・(d1)
(式(d1)中、Rd1、Rd2、及びRd3は、それぞれ独立に水素原子、又は有機基である。)
Rd4-N=CRd5Rd6・・・(d2)
(式(d2)中、Rd4、Rd5、及びRd6は、それぞれ独立に水素原子、又は有機基である。)
有機基の好適な例としては、アルキル基、シクロアルキル基、置換基を有してもよいフェニル基、置換基を有してもよいフェニルアルキル基、置換基を有してもよいナフチル基、置換基を有してもよいナフチルアルキル基、及び置換基を有してもよいヘテロシクリル基等が挙げられる。
有機基中に含まれる、フェニル基、ナフチル基、及びヘテロシクリル基が置換基を有する場合、その置換基の数は、特に限定されず、1以上4以下が好ましい。有機基中に含まれるフェニル基、ナフチル基、及びヘテロシクリル基が、複数の置換基を有する場合、複数の置換基は、同一であっても異なっていてもよい。
また、硬化物の屈折率の高さの点で、式(d2)中、Rd4、Rd5、及びRd6は、それぞれ独立に水素原子、又は有機基であり、Rd4、Rd5、及びRd6の少なくとも1つが芳香族基含有基であることが好ましい。
芳香族基含有基中の芳香環は、芳香族炭化水素環でも、芳香族複素環でもよい。芳香族基含有基としては、炭化水素基が好ましい。芳香族基含有基としては、芳香族炭化水素基(アリール基)、及びアラルキル基が好ましい。
芳香族炭化水素基としては、フェニル基、ナフタレン-1-イル基、及びナフタレン-2-イル基が挙げられる。これらの芳香族炭化水素基の中では、フェニル基が好ましい。
アラルキル基としては、ベンジル基、2-フェニルエチル基、3-フェニルプロピル基、及び4-フェニルブチル基が挙げられる。
Ard1としての芳香族基は、芳香族炭化水素基でも、芳香族複素環基でもよい。Ard1としての芳香族基としては、芳香族炭化水素基が好ましい。芳香族炭化水素基としては、フェニル基、ナフタレン-1-イル基、及びナフタレン-2-イル基が挙げられる。これらの芳香族炭化水素基の中では、フェニル基が好ましい。
Ard1としての芳香族基が有してもよい置換基は、Rd1、Rd2、Rd3、Rd4、Rd5、及びRd6としての有機基がフェニル基、ナフチル基、及びヘテロシクリル基である場合に、これらの基が有してもよい置換基と同様である。
光硬化性液状組成物は、可塑剤(E)を含んでいてもよい。可塑剤(E)は、光硬化性液状組成物の硬化性や、硬化物の屈折率を大きく損なうことなく、光硬化性液状組成物を低粘度化させる成分である。
Re1-Re3 r-Xe-Re4 s-Re2・・・(e-1)
(式(e-1)中、Re1、及びRe2は、それぞれ独立に、1以上5以下の置換基を有してもよいフェニル基であり、前記置換基が、炭素原子数1以上4以下のアルキル基、炭素原子数1以上4以下のアルコキシ基、及びハロゲン原子から選択され、Re3、及びRe4は、それぞれ独立にメチレン基、又はエタン-1,2-ジイル基であり、r、及びsは、それぞれ独立に0、又は1であり、Xeは、酸素原子、又は硫黄原子である。)
光硬化性液状組成物の低粘度化の観点で、可塑剤(E)の、25℃においてE型粘度計により測定される粘度は、10cP以下が好ましく、8cP以下がより好ましく、6cP以下がさらに好ましい。
また、可塑剤(E)が揮発しにくく、光硬化性液状組成物の低粘度化の効果を維持しやすい点から、可塑剤(E)の大気圧下での沸点が250℃以上であるのが好ましく、260℃以上であるのがより好ましい。可塑剤(E)の大気圧下での沸点の上限は特に限定されないが、例えば、300℃以下でよく、350℃以下でもよい。
式(e-1)におけるXeは、酸素原子、又は硫黄原子である。
光硬化性液状組成物は、光硬化性液状組成物の質量に対して5質量%以下の溶媒(S)を含んでいてもよい。溶媒(S)の種類は特に限定されないが、典型的には有機溶媒である。
光硬化性液状組成物は、本発明の目的を阻害しない範囲で、以上説明した成分の他に、従来から感光性組成物やインク組成物に配合されている種々の添加剤を含んでいてもよい。光硬化性液状祖組成物に配合される好ましい添加剤としては、分散剤、シランカップリング剤等の密着促進剤、酸化防止剤、凝集防止剤、消泡剤、界面活性剤等が挙げられる。界面活性剤としては、特に限定されず、フッ素系界面活性剤、シリコン系界面活性剤等の公知の成分を用いることができる。
以上説明した成分を、それぞれ所定量混合したのち、混合物を均一に撹拌することにより光硬化性液状組成物が得られる。
以上説明した光硬化性液状組成物は、典型的には、
光硬化性液状組成物を、形成される硬化物の形状に応じて成形することと、
成形された光硬化性液状組成物に対して露光することと、
を含む方法によって、硬化物とされる。
例えば、前述の光硬化性液状組成物の硬化物からなる膜は、有機ELディスプレイパネルや、液晶ディスプレイパネル等の種々のディスプレイパネルにおいて反射防止膜等を構成する高屈折率膜として好適に使用される。
光硬化性液状組成物を成形する方法としては、特に限定されない。硬化物の形状がレンズ形状やプリズム形状等である場合には、硬化物の形状に応じた鋳型中に光硬化性液状組成物をスキージ等を用いて充填してもよい。
硬化物の形状がライン形状等である場合、硬化物の形状に応じて、基材上に光硬化性液状組成物を塗布すればよい。塗布方法としては、例えば、インクジェット法等の印刷法が挙げられる。
硬化物を膜形状に塗布する方法としては、ロールコータ、リバースコータ、バーコータ等の接触転写型塗布装置や、スピンナー(回転式塗布装置)、カーテンフローコータ等の非接触型塗布装置を用いる方法が挙げられる。また、インクジェット法等の印刷法によって光硬化性液状組成物を膜形状に塗布することもできる。
また、前述の光硬化性液状組成物を、3Dプリンティング法に適用して、インクジェット印刷と、露光による硬化とを繰り返して薄膜状の硬化物を積層することにより、所望する形状の硬化物を形成してもよい。
成形された光硬化性液状組成物に対する露光は、例えば、紫外線、エキシマレーザー光等の活性エネルギー線を照射して行われる。
現像処理を行う場合、現像後に加熱による乾燥等の方法により、現像液を十分に除去するのが好ましい。
実施例、及び比較例において、光重合性モノマー(A)として、下記の化合物を用いた。
<多官能モノマー(A1)>
A1-1:下記構造の化合物
A1-2:トリメチロールプロパントリアクリレート
フェネチルアクリレート
酸化ジルコニウム粒子B2について特開2018-193481号公報の段落[0223]に記載された方法に沿って、遠心分離により回収されたナノ結晶を乾燥させることによって得た。
3-メタクリロプロピルトリメトキシシランにより表面修飾された酸化ジルコニウム粒子B1については、キャッピング剤を添加する工程において、酸化ジルコニウム粒子の質量に対して、0.8~1.5倍の質量のキャッピング剤としての3-メタクリロキシプロピルトリメトキシシランをさらに加えた他は、酸化ジルコニウム粒子B2と同様にして得た。
酸化チタン粒子B4について国際公開第2020/106860号の実施例8に記載された方法に沿って、遠心分離により回収されたナノ結晶を乾燥させることによって得た。
3-メタクリロプロピルトリメトキシシランにより表面修飾された酸化チタン粒子B3については、キャッピング剤を添加する工程において、キャッピング剤の総量の50質量%を3-メタクリロキシプロピルトリメトキシシランに置き換えた他は、酸化チタン粒子B4と同様にして得た。
実施例、及び比較例において、含窒素化合物(D)として、下記のD1~D3を用いた。
D1:N-メチルジフェニルアミン
D2:トリベンジルアミン
D3:N-ベンジルフェニルメタンイミン
また、含窒素化合物(D)を用いないことの他は、実施例1~4と同様にして、比較例1の光硬化性液状組成物を得た
さらに、下記処方に従って、光硬化性液状組成物を用いて形成された硬化膜における各金属酸化物ナノ粒子がリッチな層の厚さT1と、各金属酸化物ナノ粒子がほとんど存在しない層の厚さT2との比率T1/T2を測定した。T1/T2の値が小さいほど、硬化膜中での各金属酸化物ナノ粒子の局在が抑制されている。
ガラス基板上にインクジェット装置を用いて、各実施例、比較例の光硬化性液状組成物を塗布した。その後、395nmのUV-LED露光機を用いて、露光量2J/cm2で塗布膜を露光して硬化させ、厚さ3μmの硬化膜を得た。その膜についてMetricon社製プリズムカプラを用いて光線波長550nmでの屈折率を求めた。
ガラス基板上にスピンコートにて各実施例、比較例の光硬化性液状組成物を塗布後、385nmのUV-LED露光機を用いて、露光量2J/cm2で塗布膜を露光して硬化させ、厚さ10μmの硬化膜を得た。その膜について、Hunter Associates Laboratory, Inc.社製デスクトップ分光測色計を用いて全光線透過率、ヘイズ、及びY.I.の測定を行った。
屈折率測定対象の硬化膜と同条件で得られた硬化膜に対し、Metricon社製プリズムカプラ2010/Mを用いて、プリズムカップリング法にて各硬化膜の屈折率を計測した。硬化膜内に屈折率の異なる2種の層が検出された場合、2種の層それぞれを解析し、各層の厚さの値を得た。酸化ジルコニウム微粒子リッチな上層の厚さをT1とし、酸化ジルコニウム微粒子が少ない下層の厚さをT2とした。このようにして得られたT1及びT2から各層の厚さの比率をT1/T2として計算した。T1/T2の値を2層化の程度の評価指標とした。
Claims (15)
- 光重合性モノマー(A)と、金属酸化物ナノ粒子(B)と、光重合開始剤(C)と、含窒素化合物(D)とを含む光硬化性液状組成物であって、
前記光重合性モノマー(A)が、エチレン性不飽和二重結合を有し、
前記含窒素化合物(D)が、下記式(d1):
NRd1Rd2Rd3・・・(d1)
(式(d1)中、Rd1、Rd2、及びRd3は、それぞれ独立に水素原子、又は有機基である。)
で表されるアミン化合物(D1)、及び、下記式(d2)
Rd3-N=CRd4Rd5・・・(d2)
(式(d2)中、Rd3、Rd4、及びRd5は、それぞれ独立に水素原子、又は有機基である。)
で表されるイミン化合物(D2)からなる群より選択される少なくとも1種である、光硬化性液状組成物。 - 前記式(d1)において、Rd1、Rd2、及びRd3の少なくとも1つが芳香族基含有基であり、前記式(d2)において、Rd3、Rd4、及びRd5の少なくとも1つが芳香族基含有基である、請求項1に記載の光硬化性液状組成物。
- 前記式(d1)において、Rd1、Rd2、及びRd3の少なくとも1つがArd1-CH2-で表される基であり、前記式(d2)において、Rd3がArd1-CH2-で表される基であり、Ard1が、置換基を有してもよい芳香族基である、請求項1又は2に記載の光硬化性液状組成物。
- 前記金属酸化物ナノ粒子(B)の表面が、エチレン性不飽和二重結合含有基で修飾されている、請求項1~3のいずれか1項に記載の光硬化性液状組成物。
- 前記含窒素化合物(D)の含有量が、前記光重合性モノマー(A)の質量に対して、5質量%以上25質量%以下である、請求項1~4のいずれか1項に記載の光硬化性液状組成物。
- 前記光重合性モノマー(A)が、3以上の前記エチレン性不飽和二重結合を有する多官能モノマー(A1)を含む、請求項1~5のいずれか1項に記載の光硬化性液状組成物。
- 前記多官能モノマー(A1)が、芳香族基を含まない脂肪族化合物である、請求項6に記載の光硬化性液状組成物。
- 前記多官能モノマー(A1)が有する、前記エチレン性不飽和二重合結合の数が、3以上6以下である、請求項6又は7に記載の光硬化性液状組成物。
- 前記多官能モノマー(A1)が、下記式(A1):
(式(A1)、及び式(A2)中、MAは、それぞれ独立に、(メタ)アクリロイル基であり、Xは、それぞれ独立に、酸素原子、-NH-、又は-N(CH3)-であり、Ra1は、それぞれ独立に、エタン-1,2-ジイル基、プロパン-1,2-ジイル基、又はプロパン-1,3-ジイル基であり、Ra2は、水酸基、炭素原子数1以上4以下のアルキル基、又は-X-(Ra1-O)na1-MAで表される基であり(Xは前記と同様であり)、na1、及びna2は、それぞれ独立に、0又は1である。)
で表される化合物である、請求項6~8のいずれか1項に記載の光硬化性液状組成物。 - 前記光重合性モノマー(A)が、下記式(A3):
Ara1-Ra01-S-Ra02-O-CO-CRa03=CH2・・・(A3)
(式(A2)中、Ara1は、ハロゲン原子で置換されていてもよいフェニル基であり、Ra01は、単結合、又は炭素原子数1以上6以下のアルキレン基であり、Ra02は、炭素原子数1以上6以下のアルキレン基であり、Ra03は、水素原子、又はメチル基である。)
で表される含硫黄(メタ)アクリレートを含む、請求項1~9のいずれか1項に記載の光硬化性液状組成物。 - 前記Ara1が、フェニル基であり、前記Ra01が、単結合である、請求項10に記載の光硬化性液状組成物。
- 前記光重合開始剤(C)が、フォスフィンオキサイド系化合物を含む、請求項1~12のいずれか1項に記載の光硬化性液状組成物。
- 請求項1~13のいずれか1項に記載の光硬化性液状組成物の硬化物。
- 請求項1~13のいずれか1項に記載の光硬化性液状組成物を成形することと、
成形された前記光硬化性液状組成物に対して露光することと、を含む硬化物の製造方法。
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020237032227A KR20230147696A (ko) | 2021-02-24 | 2022-02-21 | 광 경화성 액상 조성물, 경화물, 및 경화물의 제조 방법 |
JP2023502408A JPWO2022181563A1 (ja) | 2021-02-24 | 2022-02-21 | |
US18/546,848 US20240141085A1 (en) | 2021-02-24 | 2022-02-21 | Photocurable liquid composition, cured product, and method for producing cured product |
EP22759599.8A EP4293052A1 (en) | 2021-02-24 | 2022-02-21 | Photocurable liquid composition, cured product, and method for producing cured product |
CN202280016575.5A CN116981699A (zh) | 2021-02-24 | 2022-02-21 | 光固性液态组合物、固化物、及固化物的制造方法 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2021027634 | 2021-02-24 | ||
JP2021-027634 | 2021-02-24 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2022181563A1 true WO2022181563A1 (ja) | 2022-09-01 |
Family
ID=83048025
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2022/007038 WO2022181563A1 (ja) | 2021-02-24 | 2022-02-21 | 光硬化性液状組成物、硬化物、及び硬化物の製造方法 |
Country Status (7)
Country | Link |
---|---|
US (1) | US20240141085A1 (ja) |
EP (1) | EP4293052A1 (ja) |
JP (1) | JPWO2022181563A1 (ja) |
KR (1) | KR20230147696A (ja) |
CN (1) | CN116981699A (ja) |
TW (1) | TW202244086A (ja) |
WO (1) | WO2022181563A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2024181199A1 (ja) * | 2023-02-27 | 2024-09-06 | 住友化学株式会社 | 硬化性組成物及び硬化膜 |
Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2004176006A (ja) * | 2002-11-29 | 2004-06-24 | Sumitomo Seika Chem Co Ltd | 光硬化性組成物 |
JP2004307579A (ja) * | 2003-04-03 | 2004-11-04 | Mitsubishi Chemicals Corp | 活性エネルギー線硬化性コーティング剤組成物及び該組成物から得られる硬化皮膜を有する成形品 |
JP2007507582A (ja) * | 2003-05-27 | 2007-03-29 | ゼネラル・エレクトリック・カンパニイ | 硬化性(メタ)アクリレート組成物 |
JP2008081726A (ja) * | 2006-08-30 | 2008-04-10 | Sanyo Electric Co Ltd | 有機無機複合体形成用材料及び有機無機複合体並びにそれを用いた光学素子 |
JP2009132763A (ja) * | 2007-11-29 | 2009-06-18 | Toyo Ink Mfg Co Ltd | 硬化性組成物 |
JP2017214465A (ja) | 2016-05-31 | 2017-12-07 | 三洋化成工業株式会社 | 活性エネルギー線硬化性組成物 |
JP2018193481A (ja) | 2017-05-17 | 2018-12-06 | 東京応化工業株式会社 | 硬化性組成物、硬化物、硬化膜、表示パネル、及び硬化物の製造方法 |
WO2020106860A1 (en) | 2018-11-20 | 2020-05-28 | Pixelligent Technologies Llc | Synthesis, capping, and dispersion of tio2 nanocrystals |
WO2021039783A1 (ja) * | 2019-08-28 | 2021-03-04 | 東京応化工業株式会社 | 硬化性インク組成物、硬化物、及びナノコンポジット |
-
2022
- 2022-02-21 KR KR1020237032227A patent/KR20230147696A/ko unknown
- 2022-02-21 WO PCT/JP2022/007038 patent/WO2022181563A1/ja active Application Filing
- 2022-02-21 US US18/546,848 patent/US20240141085A1/en active Pending
- 2022-02-21 JP JP2023502408A patent/JPWO2022181563A1/ja active Pending
- 2022-02-21 EP EP22759599.8A patent/EP4293052A1/en active Pending
- 2022-02-21 CN CN202280016575.5A patent/CN116981699A/zh active Pending
- 2022-02-24 TW TW111106752A patent/TW202244086A/zh unknown
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2004176006A (ja) * | 2002-11-29 | 2004-06-24 | Sumitomo Seika Chem Co Ltd | 光硬化性組成物 |
JP2004307579A (ja) * | 2003-04-03 | 2004-11-04 | Mitsubishi Chemicals Corp | 活性エネルギー線硬化性コーティング剤組成物及び該組成物から得られる硬化皮膜を有する成形品 |
JP2007507582A (ja) * | 2003-05-27 | 2007-03-29 | ゼネラル・エレクトリック・カンパニイ | 硬化性(メタ)アクリレート組成物 |
JP2008081726A (ja) * | 2006-08-30 | 2008-04-10 | Sanyo Electric Co Ltd | 有機無機複合体形成用材料及び有機無機複合体並びにそれを用いた光学素子 |
JP2009132763A (ja) * | 2007-11-29 | 2009-06-18 | Toyo Ink Mfg Co Ltd | 硬化性組成物 |
JP2017214465A (ja) | 2016-05-31 | 2017-12-07 | 三洋化成工業株式会社 | 活性エネルギー線硬化性組成物 |
JP2018193481A (ja) | 2017-05-17 | 2018-12-06 | 東京応化工業株式会社 | 硬化性組成物、硬化物、硬化膜、表示パネル、及び硬化物の製造方法 |
WO2020106860A1 (en) | 2018-11-20 | 2020-05-28 | Pixelligent Technologies Llc | Synthesis, capping, and dispersion of tio2 nanocrystals |
WO2021039783A1 (ja) * | 2019-08-28 | 2021-03-04 | 東京応化工業株式会社 | 硬化性インク組成物、硬化物、及びナノコンポジット |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2024181199A1 (ja) * | 2023-02-27 | 2024-09-06 | 住友化学株式会社 | 硬化性組成物及び硬化膜 |
Also Published As
Publication number | Publication date |
---|---|
KR20230147696A (ko) | 2023-10-23 |
TW202244086A (zh) | 2022-11-16 |
EP4293052A1 (en) | 2023-12-20 |
CN116981699A (zh) | 2023-10-31 |
JPWO2022181563A1 (ja) | 2022-09-01 |
US20240141085A1 (en) | 2024-05-02 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6225921B2 (ja) | 硬化膜形成用樹脂組成物 | |
WO2022225029A1 (ja) | 光硬化性組成物 | |
WO2022181563A1 (ja) | 光硬化性液状組成物、硬化物、及び硬化物の製造方法 | |
JP7335975B2 (ja) | 感光性インク組成物、硬化物、ディスプレイパネル、及び硬化物の製造方法 | |
JP7565875B2 (ja) | 硬化性組成物、硬化物、及び硬化物の製造方法 | |
WO2022181562A1 (ja) | 光硬化性液状組成物、硬化物、及び硬化物の製造方法 | |
JP2022129076A (ja) | 光硬化性液状組成物、硬化物、及び硬化物の製造方法 | |
JP7335974B2 (ja) | 感光性インク組成物、硬化物、ディスプレイパネル、及び硬化物の製造方法 | |
KR20220094163A (ko) | 광 경화성 액상 조성물, 경화물, 및 경화물의 제조 방법 | |
CN114686025A (zh) | 光固性液态组合物、固化物、及固化物的制造方法 | |
JP2024085754A (ja) | 感光性組成物、硬化物、及び硬化物の製造方法 | |
WO2023203845A1 (ja) | 組成物、及び感光性組成物 | |
JP2024085753A (ja) | 感光性組成物、硬化物、及び硬化物の製造方法 | |
WO2023120077A1 (ja) | 組成物、及び感光性組成物 | |
WO2023203837A1 (ja) | 組成物、及び感光性組成物 | |
JP2024085734A (ja) | 組成物、及び感光性組成物 | |
WO2023047850A1 (ja) | 感光性組成物 | |
WO2023074265A1 (ja) | 感光性組成物 | |
WO2023047855A1 (ja) | 組成物、及び感光性組成物 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 22759599 Country of ref document: EP Kind code of ref document: A1 |
|
WWE | Wipo information: entry into national phase |
Ref document number: 18546848 Country of ref document: US |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2023502408 Country of ref document: JP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 202280016575.5 Country of ref document: CN |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2022759599 Country of ref document: EP |
|
ENP | Entry into the national phase |
Ref document number: 20237032227 Country of ref document: KR Kind code of ref document: A |
|
WWE | Wipo information: entry into national phase |
Ref document number: 1020237032227 Country of ref document: KR |
|
ENP | Entry into the national phase |
Ref document number: 2022759599 Country of ref document: EP Effective date: 20230914 |
|
NENP | Non-entry into the national phase |
Ref country code: DE |