JP2001097975A - 蛍光ジケトピロロピロール - Google Patents
蛍光ジケトピロロピロールInfo
- Publication number
- JP2001097975A JP2001097975A JP2000288313A JP2000288313A JP2001097975A JP 2001097975 A JP2001097975 A JP 2001097975A JP 2000288313 A JP2000288313 A JP 2000288313A JP 2000288313 A JP2000288313 A JP 2000288313A JP 2001097975 A JP2001097975 A JP 2001097975A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- twenty
- substituted
- phenyl
- added
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 title 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 24
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
- -1 Tetramethylene, pentamethylene Chemical group 0.000 claims description 75
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 59
- 239000000203 mixture Substances 0.000 claims description 54
- 150000001875 compounds Chemical class 0.000 claims description 41
- 239000011541 reaction mixture Substances 0.000 claims description 34
- 239000011368 organic material Substances 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 24
- 239000002168 alkylating agent Substances 0.000 claims description 23
- 229940100198 alkylating agent Drugs 0.000 claims description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- 238000004519 manufacturing process Methods 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000002585 base Substances 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 7
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Chemical group 0.000 claims description 5
- 125000006413 ring segment Chemical group 0.000 claims description 5
- 229910052717 sulfur Chemical group 0.000 claims description 5
- 239000011593 sulfur Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
- 125000000524 functional group Chemical group 0.000 claims description 3
- 150000004678 hydrides Chemical class 0.000 claims description 3
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 3
- 125000001302 tertiary amino group Chemical group 0.000 claims description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- ACJSMQZKXAMMRA-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyrrol-5-one Chemical class N1C=CC2=NC(=O)C=C21 ACJSMQZKXAMMRA-UHFFFAOYSA-N 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 125000004965 chloroalkyl group Chemical group 0.000 claims 1
- 229920003023 plastic Polymers 0.000 abstract description 10
- 239000004033 plastic Substances 0.000 abstract description 10
- 239000007850 fluorescent dye Substances 0.000 abstract description 8
- 125000001624 naphthyl group Chemical group 0.000 abstract description 2
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- 239000000976 ink Substances 0.000 description 49
- 239000007787 solid Substances 0.000 description 47
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 239000000049 pigment Substances 0.000 description 29
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 22
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
- 239000006185 dispersion Substances 0.000 description 21
- 238000000921 elemental analysis Methods 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 239000002904 solvent Substances 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 238000007639 printing Methods 0.000 description 18
- 239000007790 solid phase Substances 0.000 description 18
- 229920000642 polymer Polymers 0.000 description 17
- 238000001816 cooling Methods 0.000 description 16
- 238000001914 filtration Methods 0.000 description 16
- 239000002270 dispersing agent Substances 0.000 description 15
- 239000000463 material Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- 239000003973 paint Substances 0.000 description 13
- YKPJEYXZEBLYCI-UHFFFAOYSA-N pyrrolo[3,4-c]pyrrole Chemical compound C1=NC=C2C=NC=C21 YKPJEYXZEBLYCI-UHFFFAOYSA-N 0.000 description 13
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 12
- 238000000576 coating method Methods 0.000 description 12
- 239000012299 nitrogen atmosphere Substances 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 11
- 239000012312 sodium hydride Substances 0.000 description 11
- 229910000104 sodium hydride Inorganic materials 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- 239000004800 polyvinyl chloride Substances 0.000 description 10
- 229920000915 polyvinyl chloride Polymers 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- 239000004952 Polyamide Substances 0.000 description 9
- 238000002835 absorbance Methods 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 9
- 239000004014 plasticizer Substances 0.000 description 9
- 229920002647 polyamide Polymers 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000002002 slurry Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 8
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 7
- 239000002480 mineral oil Substances 0.000 description 7
- 235000010446 mineral oil Nutrition 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 239000000945 filler Substances 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- CJEWDMJPUFTJJZ-UHFFFAOYSA-N 1,4-dinaphthalen-2-ylpyrrolo[3,4-c]pyrrole-3,6-dione Chemical compound C1=CC=CC2=CC(C=3C4=C(C(N=3)=O)C(C=3C=C5C=CC=CC5=CC=3)=NC4=O)=CC=C21 CJEWDMJPUFTJJZ-UHFFFAOYSA-N 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 5
- 239000012736 aqueous medium Substances 0.000 description 5
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 238000004040 coloring Methods 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 239000000314 lubricant Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 230000000269 nucleophilic effect Effects 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 239000004925 Acrylic resin Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 4
- 229920000180 alkyd Polymers 0.000 description 4
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000007641 inkjet printing Methods 0.000 description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000000465 moulding Methods 0.000 description 4
- 239000003880 polar aprotic solvent Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 239000004753 textile Substances 0.000 description 4
- GMZBMXSSGCHKEM-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)pyrrolo[3,4-c]pyrrole-3,6-dione Chemical compound C1=CC(Cl)=CC=C1C1=NC(=O)C2=C1C(=O)N=C2C1=CC=C(Cl)C=C1 GMZBMXSSGCHKEM-UHFFFAOYSA-N 0.000 description 3
- QXDHXCVJGBTQMK-UHFFFAOYSA-N 1-(bromomethyl)-3,5-dimethylbenzene Chemical compound CC1=CC(C)=CC(CBr)=C1 QXDHXCVJGBTQMK-UHFFFAOYSA-N 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 3
- YUXIBTJKHLUKBD-UHFFFAOYSA-N Dibutyl succinate Chemical compound CCCCOC(=O)CCC(=O)OCCCC YUXIBTJKHLUKBD-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 239000000020 Nitrocellulose Substances 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 235000005811 Viola adunca Nutrition 0.000 description 3
- 240000009038 Viola odorata Species 0.000 description 3
- 235000013487 Viola odorata Nutrition 0.000 description 3
- 235000002254 Viola papilionacea Nutrition 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 3
- 150000008046 alkali metal hydrides Chemical class 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 229920006217 cellulose acetate butyrate Polymers 0.000 description 3
- 229920001727 cellulose butyrate Polymers 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000002274 desiccant Substances 0.000 description 3
- YPLYFEUBZLLLIY-UHFFFAOYSA-N dipropan-2-yl butanedioate Chemical compound CC(C)OC(=O)CCC(=O)OC(C)C YPLYFEUBZLLLIY-UHFFFAOYSA-N 0.000 description 3
- XIMIGUBYDJDCKI-UHFFFAOYSA-N diselenium Chemical compound [Se]=[Se] XIMIGUBYDJDCKI-UHFFFAOYSA-N 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 238000005562 fading Methods 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 238000001746 injection moulding Methods 0.000 description 3
- 239000002808 molecular sieve Substances 0.000 description 3
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 229920001220 nitrocellulos Polymers 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 239000005011 phenolic resin Substances 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 239000004926 polymethyl methacrylate Substances 0.000 description 3
- 229920000098 polyolefin Polymers 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 3
- 238000006862 quantum yield reaction Methods 0.000 description 3
- 239000000700 radioactive tracer Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000005060 rubber Substances 0.000 description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical class S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 3
- WNFKKYHWMDGKBD-UHFFFAOYSA-N 1,4-bis(4-morpholin-4-ylphenyl)pyrrolo[3,4-c]pyrrole-3,6-dione Chemical compound C=1C=C(N2CCOCC2)C=CC=1C1=NC(=O)C2=C1C(=O)N=C2C(C=C1)=CC=C1N1CCOCC1 WNFKKYHWMDGKBD-UHFFFAOYSA-N 0.000 description 2
- PZZLHRMRDLGPNU-UHFFFAOYSA-N 1,4-bis[4-(n-phenylanilino)phenyl]pyrrolo[3,4-c]pyrrole-3,6-dione Chemical compound C=1C=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1C1=NC(=O)C2=C1C(=O)N=C2C(C=C1)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 PZZLHRMRDLGPNU-UHFFFAOYSA-N 0.000 description 2
- SNRYBGHMHAJTTM-UHFFFAOYSA-N 1-(bromomethyl)-3,5-ditert-butylbenzene Chemical compound CC(C)(C)C1=CC(CBr)=CC(C(C)(C)C)=C1 SNRYBGHMHAJTTM-UHFFFAOYSA-N 0.000 description 2
- DVGQWQMPCZYJLR-UHFFFAOYSA-N 1-chloro-4-[(4-chlorophenyl)diselanyl]benzene Chemical compound C1=CC(Cl)=CC=C1[Se][Se]C1=CC=C(Cl)C=C1 DVGQWQMPCZYJLR-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
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- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- JMHCCAYJTTWMCX-QWPJCUCISA-M sodium;(2s)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoate;pentahydrate Chemical compound O.O.O.O.O.[Na+].IC1=CC(C[C@H](N)C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 JMHCCAYJTTWMCX-QWPJCUCISA-M 0.000 description 1
- CGRKYEALWSRNJS-UHFFFAOYSA-N sodium;2-methylbutan-2-olate Chemical compound [Na+].CCC(C)(C)[O-] CGRKYEALWSRNJS-UHFFFAOYSA-N 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QVLMUEOXQBUPAH-UHFFFAOYSA-N stilben-4-ol Chemical compound C1=CC(O)=CC=C1C=CC1=CC=CC=C1 QVLMUEOXQBUPAH-UHFFFAOYSA-N 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical group COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 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
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000004636 vulcanized rubber Substances 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000005019 zein Substances 0.000 description 1
- 229940093612 zein Drugs 0.000 description 1
- UQYXBOKTDPWSCS-UHFFFAOYSA-L zinc;4-nonylphenolate Chemical compound [Zn+2].CCCCCCCCCC1=CC=C([O-])C=C1.CCCCCCCCCC1=CC=C([O-])C=C1 UQYXBOKTDPWSCS-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/004—Diketopyrrolopyrrole dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP99810867 | 1999-09-27 | ||
| EP99810867.4 | 1999-09-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2001097975A true JP2001097975A (ja) | 2001-04-10 |
| JP2001097975A5 JP2001097975A5 (enExample) | 2006-07-27 |
Family
ID=8243047
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000288313A Pending JP2001097975A (ja) | 1999-09-27 | 2000-09-22 | 蛍光ジケトピロロピロール |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US6603020B1 (enExample) |
| JP (1) | JP2001097975A (enExample) |
| KR (1) | KR100753348B1 (enExample) |
| DE (1) | DE60008472T2 (enExample) |
| TW (1) | TWI261064B (enExample) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006319347A (ja) * | 1999-09-27 | 2006-11-24 | Ciba Specialty Chem Holding Inc | ジケトピロロピロール類を含むエレクトロルミネセンス素子 |
| JP2010529114A (ja) * | 2007-06-05 | 2010-08-26 | エルジー・ケム・リミテッド | 光学異方性化合物及びこれを含む樹脂組成物 |
| JP2011257730A (ja) * | 2010-06-10 | 2011-12-22 | Samsung Electronics Co Ltd | 表示装置 |
| JP2016510052A (ja) * | 2013-03-06 | 2016-04-04 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 新規な複素環式蛍光染料及びその製造方法 |
| WO2020040043A1 (ja) * | 2018-08-22 | 2020-02-27 | 富士フイルム株式会社 | 着色組成物、硬化膜、パターン形成方法、カラーフィルタ、固体撮像素子および画像表示装置 |
| WO2023167026A1 (ja) * | 2022-03-02 | 2023-09-07 | 東洋インキＳｃホールディングス株式会社 | ジケトピロロピロール顔料、顔料組成物、着色組成物、カラーフィルタおよびセンサ |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003002672A2 (en) * | 2001-06-29 | 2003-01-09 | Ciba Specialty Chemicals Holding Inc. | Fluorescent diketopyrrolopyrroles |
| JP2004537638A (ja) * | 2001-08-10 | 2004-12-16 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | 蛍光性ジケトピロロピロール類似体 |
| WO2003048268A1 (fr) * | 2001-12-03 | 2003-06-12 | Toyo Ink Mfg. Co., Ltd. | Composition pour element electroluminescent organique et element electroluminescent organique utilisant cette composition |
| EP1478713A1 (en) * | 2002-02-01 | 2004-11-24 | Ciba SC Holding AG | Fluorescent compositions comprising diketopyrrolopyrroles |
| US7501076B2 (en) * | 2003-04-10 | 2009-03-10 | Ciba Specialty Chemicals Corporation | Fluorescent diketopyrrolopyrroles |
| EP1649275A4 (en) * | 2003-08-01 | 2007-12-19 | Glotell Products Inc | DYE SOLUTIONS FOR USE IN METHODS OF DETECTING THE PREVIOUS EVAPORATION OF ANHYDROUS AMMONIA AND THE PRODUCTION OF ILLEGAL DRUGS |
| CN1977029A (zh) * | 2004-06-29 | 2007-06-06 | 西巴特殊化学品控股有限公司 | 荧光喹吖啶酮 |
| WO2006021527A1 (en) * | 2004-08-23 | 2006-03-02 | Ciba Specialty Chemicals Holding Inc. | Cosmetic compositions containing fluorescent colorants for natural skin appearance |
| CA2587781A1 (en) * | 2004-12-09 | 2006-06-15 | Ciba Specialty Chemicals Holding Inc. | Fluorescent diketopyrrolopyrroles |
| JP5431340B2 (ja) | 2007-10-09 | 2014-03-05 | ビーエーエスエフ ソシエタス・ヨーロピア | ピロロピロール誘導体、その製造及び使用 |
| GB201200184D0 (en) * | 2012-01-06 | 2012-02-22 | Johnson Matthey Plc | Tracers and method of marking liquids |
| CN110818936B (zh) * | 2019-11-14 | 2022-04-05 | 陕西理工大学 | 一种有机玻璃及其制备方法和应用 |
| CN116969952A (zh) * | 2023-07-31 | 2023-10-31 | 山东凯瑞尔光电科技有限公司 | 一种二苯基吡咯并吡咯二酮衍生物及其颜料组合物 |
| CN116969953A (zh) * | 2023-07-31 | 2023-10-31 | 山东凯瑞尔光电科技有限公司 | 一种二苯基吡咯并吡咯二酮衍生物及颜料组合物和其应用 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3262270D1 (en) * | 1981-03-20 | 1985-03-28 | Ciba Geigy Ag | Process for colouring highly molecular organic material and polycyclic pigments |
| DE3366011D1 (en) * | 1982-05-17 | 1986-10-16 | Ciba Geigy Ag | Preparation of pyrrolo-(3,4-c) pyrroles |
| US4585878A (en) | 1983-06-29 | 1986-04-29 | Ciba-Geigy Corporation | N-substituted 1,4-diketopyrrolo-[3,4-c]-pyrroles |
| DE58907880D1 (de) | 1988-07-20 | 1994-07-21 | Ciba Geigy | Verfahren zur Herstellung aminierter Diketodi(het)aryl-pyrrolopyrrole und Verwendung derselben als photoleitfähige Substanzen. |
| EP0426717B1 (de) * | 1988-07-29 | 1996-04-24 | Riedel-De Haen Aktiengesellschaft | Optische datenspeicher |
| JPH02296891A (ja) * | 1989-05-10 | 1990-12-07 | Ricoh Co Ltd | 電界発光素子 |
| US5476886A (en) * | 1994-07-18 | 1995-12-19 | Ciba-Geigy Corporation | Polyamides mass coloured with diketopyrrolopyrrole pigments |
| GB9418499D0 (en) | 1994-09-14 | 1994-11-02 | Ciba Geigy Ag | Process for producing n-methylated organic pigments |
| JP3704748B2 (ja) * | 1995-06-23 | 2005-10-12 | 東洋インキ製造株式会社 | 有機エレクトロルミネッセンス素子用電子輸送材料およびそれを用いた有機エレクトロルミネッセンス素子 |
| DE69711985T2 (de) | 1996-06-05 | 2002-10-31 | Ciba Speciality Chemicals Holding Inc., Basel | Verfahren zur Herstellung von Diketopyrrolopyrrolderivaten |
| WO1998025927A1 (en) | 1996-12-10 | 1998-06-18 | Ciba Specialty Chemicals Holding Inc. | Liquid crystalline diketopyrrolopyrroles |
| EP0968250B1 (en) | 1997-01-27 | 2001-04-18 | Ciba SC Holding AG | Soluble chromophores having improved solubilising groups |
| DK0968254T3 (da) * | 1997-02-03 | 2004-12-06 | Ciba Sc Holding Ag | Fluorescerende materialer og deres anvendelse |
-
2000
- 2000-09-06 TW TW089118230A patent/TWI261064B/zh not_active IP Right Cessation
- 2000-09-07 US US09/735,080 patent/US6603020B1/en not_active Expired - Fee Related
- 2000-09-19 DE DE60008472T patent/DE60008472T2/de not_active Expired - Lifetime
- 2000-09-22 JP JP2000288313A patent/JP2001097975A/ja active Pending
- 2000-09-27 KR KR1020000056659A patent/KR100753348B1/ko not_active Expired - Fee Related
-
2003
- 2003-01-30 US US10/354,602 patent/US20030187106A1/en not_active Abandoned
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006319347A (ja) * | 1999-09-27 | 2006-11-24 | Ciba Specialty Chem Holding Inc | ジケトピロロピロール類を含むエレクトロルミネセンス素子 |
| JP2010529114A (ja) * | 2007-06-05 | 2010-08-26 | エルジー・ケム・リミテッド | 光学異方性化合物及びこれを含む樹脂組成物 |
| JP2013249311A (ja) * | 2007-06-05 | 2013-12-12 | Lg Chem Ltd | 光学異方性化合物及びこれを含む樹脂組成物 |
| JP2011257730A (ja) * | 2010-06-10 | 2011-12-22 | Samsung Electronics Co Ltd | 表示装置 |
| US9122089B2 (en) | 2010-06-10 | 2015-09-01 | Samsung Display Co., Ltd. | Display device |
| JP2016510052A (ja) * | 2013-03-06 | 2016-04-04 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 新規な複素環式蛍光染料及びその製造方法 |
| WO2020040043A1 (ja) * | 2018-08-22 | 2020-02-27 | 富士フイルム株式会社 | 着色組成物、硬化膜、パターン形成方法、カラーフィルタ、固体撮像素子および画像表示装置 |
| CN112566985A (zh) * | 2018-08-22 | 2021-03-26 | 富士胶片株式会社 | 着色组合物、固化膜、图案形成方法、滤色器、固体摄像元件及图像显示装置 |
| WO2023167026A1 (ja) * | 2022-03-02 | 2023-09-07 | 東洋インキＳｃホールディングス株式会社 | ジケトピロロピロール顔料、顔料組成物、着色組成物、カラーフィルタおよびセンサ |
Also Published As
| Publication number | Publication date |
|---|---|
| US20030187106A1 (en) | 2003-10-02 |
| DE60008472T2 (de) | 2004-06-24 |
| DE60008472D1 (de) | 2004-04-01 |
| US6603020B1 (en) | 2003-08-05 |
| KR100753348B1 (ko) | 2007-08-30 |
| TWI261064B (en) | 2006-09-01 |
| KR20010030502A (ko) | 2001-04-16 |
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