JP5068528B2 - 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 Download PDFInfo
- Publication number
- JP5068528B2 JP5068528B2 JP2006505506A JP2006505506A JP5068528B2 JP 5068528 B2 JP5068528 B2 JP 5068528B2 JP 2006505506 A JP2006505506 A JP 2006505506A JP 2006505506 A JP2006505506 A JP 2006505506A JP 5068528 B2 JP5068528 B2 JP 5068528B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- alkyl
- phenyl
- substituted
- compounds
- 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.)
- Expired - Lifetime
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- 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 claims description 48
- 239000000203 mixture Substances 0.000 claims description 60
- 239000000463 material Substances 0.000 claims description 59
- 239000001257 hydrogen Substances 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 38
- 150000002431 hydrogen Chemical class 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 238000005424 photoluminescence Methods 0.000 claims description 7
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 4
- 238000000862 absorption spectrum Methods 0.000 claims description 2
- 238000002189 fluorescence spectrum Methods 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 125
- -1 color filters Substances 0.000 description 95
- 125000000217 alkyl group Chemical group 0.000 description 67
- 238000000034 method Methods 0.000 description 62
- 150000001875 compounds Chemical class 0.000 description 55
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 42
- 230000005525 hole transport Effects 0.000 description 41
- 125000003545 alkoxy group Chemical group 0.000 description 36
- 125000003118 aryl group Chemical group 0.000 description 34
- 125000000623 heterocyclic group Chemical group 0.000 description 32
- 239000000758 substrate Substances 0.000 description 30
- 125000000753 cycloalkyl group Chemical group 0.000 description 29
- 229910052757 nitrogen Inorganic materials 0.000 description 29
- 239000000976 ink Substances 0.000 description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 20
- 238000002360 preparation method Methods 0.000 description 17
- 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 16
- 125000004093 cyano group Chemical group *C#N 0.000 description 16
- 239000011368 organic material Substances 0.000 description 16
- 238000007639 printing Methods 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- 238000001771 vacuum deposition Methods 0.000 description 16
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 15
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 15
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 15
- 229910052736 halogen Inorganic materials 0.000 description 15
- 150000002367 halogens Chemical class 0.000 description 15
- 238000002347 injection Methods 0.000 description 15
- 239000007924 injection Substances 0.000 description 15
- 238000000576 coating method Methods 0.000 description 14
- 239000010408 film Substances 0.000 description 14
- 239000000049 pigment Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 125000003710 aryl alkyl group Chemical group 0.000 description 13
- 229910052717 sulfur Inorganic materials 0.000 description 13
- 239000011248 coating agent Substances 0.000 description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 12
- 229910052760 oxygen Inorganic materials 0.000 description 12
- 239000001301 oxygen Substances 0.000 description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 11
- 238000004020 luminiscence type Methods 0.000 description 11
- 238000004528 spin coating Methods 0.000 description 11
- 239000011593 sulfur Substances 0.000 description 11
- 238000005266 casting Methods 0.000 description 10
- 239000006185 dispersion Substances 0.000 description 10
- 125000005842 heteroatom Chemical group 0.000 description 10
- 239000003973 paint Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 229910052782 aluminium Inorganic materials 0.000 description 9
- 125000001072 heteroaryl group Chemical group 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000010409 thin film Substances 0.000 description 9
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 8
- 230000001629 suppression Effects 0.000 description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- 125000003172 aldehyde group Chemical group 0.000 description 7
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 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 7
- 238000005401 electroluminescence Methods 0.000 description 7
- 125000004185 ester group Chemical group 0.000 description 7
- 239000011777 magnesium Substances 0.000 description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 description 7
- 125000005401 siloxanyl group Chemical group 0.000 description 7
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000008096 xylene Substances 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 125000004414 alkyl thio group Chemical group 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 229920003023 plastic Polymers 0.000 description 6
- 239000004033 plastic Substances 0.000 description 6
- 229920005596 polymer binder Polymers 0.000 description 6
- 239000002491 polymer binding agent Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 125000006413 ring segment Chemical group 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 125000000304 alkynyl group Chemical group 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Chemical group 0.000 description 5
- 239000000460 chlorine Chemical group 0.000 description 5
- 239000003086 colorant Substances 0.000 description 5
- 238000004040 coloring Methods 0.000 description 5
- 125000000392 cycloalkenyl group Chemical group 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 125000000262 haloalkenyl group Chemical group 0.000 description 5
- 125000001188 haloalkyl group Chemical group 0.000 description 5
- 125000000232 haloalkynyl group Chemical group 0.000 description 5
- 229910052749 magnesium Inorganic materials 0.000 description 5
- 229910001092 metal group alloy Inorganic materials 0.000 description 5
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 5
- 239000004926 polymethyl methacrylate Substances 0.000 description 5
- 239000010453 quartz Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 229910052709 silver Inorganic materials 0.000 description 5
- 239000004332 silver Substances 0.000 description 5
- 125000001544 thienyl group Chemical group 0.000 description 5
- 229910001316 Ag alloy Inorganic materials 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- 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 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 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 4
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 229910052738 indium Inorganic materials 0.000 description 4
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 4
- 238000007641 inkjet printing Methods 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000000468 ketone group Chemical group 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 229920006395 saturated elastomer Polymers 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
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 description 4
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 3
- 229910000838 Al alloy Inorganic materials 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 0 CN(C(*)=*(C1=C(*)N2*)C2=O)C1=O Chemical compound CN(C(*)=*(C1=C(*)N2*)C2=O)C1=O 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 229920000180 alkyd Polymers 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 125000005013 aryl ether group Chemical group 0.000 description 3
- 150000004832 aryl thioethers Chemical group 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
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 229920001940 conductive polymer Polymers 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
- 239000000975 dye Substances 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 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 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 239000012038 nucleophile Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 229920001197 polyacetylene Polymers 0.000 description 3
- 229920000767 polyaniline Polymers 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 229920000128 polypyrrole Polymers 0.000 description 3
- 229920000123 polythiophene Polymers 0.000 description 3
- 229920000915 polyvinyl chloride Polymers 0.000 description 3
- 239000004800 polyvinyl chloride Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 125000000168 pyrrolyl group Chemical group 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 125000001698 2H-pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 2
- DMSHUVBQFSNBBL-UHFFFAOYSA-N 5-bromopyridine-2-carbonitrile Chemical compound BrC1=CC=C(C#N)N=C1 DMSHUVBQFSNBBL-UHFFFAOYSA-N 0.000 description 2
- YVVHCBNJWHPMCQ-UHFFFAOYSA-N 5-bromothiophene-2-carbonitrile Chemical compound BrC1=CC=C(C#N)S1 YVVHCBNJWHPMCQ-UHFFFAOYSA-N 0.000 description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 125000005915 C6-C14 aryl group Chemical group 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- YUXIBTJKHLUKBD-UHFFFAOYSA-N Dibutyl succinate Chemical compound CCCCOC(=O)CCC(=O)OCCCC YUXIBTJKHLUKBD-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 229910001218 Gallium arsenide Inorganic materials 0.000 description 2
- 229910007857 Li-Al Inorganic materials 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 229910008447 Li—Al Inorganic materials 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- 239000004640 Melamine resin Substances 0.000 description 2
- 229910000861 Mg alloy Inorganic materials 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 239000000020 Nitrocellulose Substances 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 229920000265 Polyparaphenylene Polymers 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- MNLAVFKVRUQAKW-UHFFFAOYSA-N VR nerve agent Chemical compound CCN(CC)CCSP(C)(=O)OCC(C)C MNLAVFKVRUQAKW-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 2
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- 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
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
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- 239000010937 tungsten Substances 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- 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
-
- 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
-
- 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
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Electroluminescent Light Sources (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03100972.3 | 2003-04-10 | ||
| EP03100972 | 2003-04-10 | ||
| PCT/EP2004/050403 WO2004090046A1 (en) | 2003-04-10 | 2004-04-01 | Fluorescent diketopyrrolopyrroles |
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| Application Number | Title | Priority Date | Filing Date |
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| JP2011146241A Division JP5523402B2 (ja) | 2003-04-10 | 2011-06-30 | 蛍光ジケトピロロピロール |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006524281A JP2006524281A (ja) | 2006-10-26 |
| JP2006524281A5 JP2006524281A5 (enExample) | 2007-05-24 |
| JP5068528B2 true JP5068528B2 (ja) | 2012-11-07 |
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| JP2006505506A Expired - Lifetime JP5068528B2 (ja) | 2003-04-10 | 2004-04-01 | 蛍光ジケトピロロピロール |
| JP2011146241A Expired - Lifetime JP5523402B2 (ja) | 2003-04-10 | 2011-06-30 | 蛍光ジケトピロロピロール |
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| JP2011146241A Expired - Lifetime JP5523402B2 (ja) | 2003-04-10 | 2011-06-30 | 蛍光ジケトピロロピロール |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US7501076B2 (enExample) |
| EP (1) | EP1611207B1 (enExample) |
| JP (2) | JP5068528B2 (enExample) |
| KR (1) | KR101130094B1 (enExample) |
| CN (1) | CN1771298B (enExample) |
| MX (1) | MXPA05010866A (enExample) |
| TW (1) | TWI347970B (enExample) |
| WO (1) | WO2004090046A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011225597A (ja) * | 2003-04-10 | 2011-11-10 | Ciba Holding Inc | 蛍光ジケトピロロピロール |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3823512A1 (de) | 1988-07-12 | 1990-01-18 | Heraeus Schott Quarzschmelze | Bestrahlungseinheit |
| EP1605733A4 (en) * | 2003-03-14 | 2009-08-05 | Semiconductor Energy Lab | CONJUGATED MOLECULE, ELECTROLUMINESCENT ELEMENT USING THE SAME, AND ELECTRONIC APPARATUS USING THE LIGHT EMITTING ELEMENT |
| GB2419738B (en) * | 2004-10-29 | 2009-11-11 | Hewlett Packard Development Co | Printing a light emitting element |
| JP2008523023A (ja) * | 2004-12-09 | 2008-07-03 | チバ 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 |
| CN101479272B (zh) * | 2006-06-30 | 2014-11-19 | 西巴控股有限公司 | 作为有机半导体的二酮基吡咯并吡咯聚合物 |
| CA2655076A1 (en) | 2006-06-30 | 2008-01-03 | Ciba Holding Inc. | Diketopyrrolopyrrole polymers as organic semiconductors |
| CA2700713A1 (en) | 2007-10-09 | 2009-04-16 | Zhimin Hao | Pyrrolopyrrole derivatives, their manufacture and use |
| JP5635070B2 (ja) | 2009-03-23 | 2014-12-03 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 有機半導体デバイスでの使用のためのジケトピロロピロールポリマー |
| WO2010115767A1 (en) | 2009-04-08 | 2010-10-14 | Basf Se | Pyrrolopyrrole derivatives, their manufacture and use as semiconductors |
| JP5629067B2 (ja) * | 2009-08-18 | 2014-11-19 | 富士フイルム株式会社 | 顔料微粒子分散体、これを用いたカラーフィルタ、及び顔料微粒子分散体の製造方法、並びに顔料誘導体化合物 |
| JP5778162B2 (ja) * | 2009-10-22 | 2015-09-16 | エージェンシー フォー サイエンス，テクノロジー アンド リサーチ | Ｎ型材料および有機電子デバイス |
| EP2621927B1 (en) | 2010-09-29 | 2020-02-12 | Basf Se | Semiconductors based on diketopyrrolopyrroles |
| US8946376B2 (en) | 2010-09-29 | 2015-02-03 | Basf Se | Semiconductors based on diketopyrrolopyrroles |
| PL397479A1 (pl) * | 2011-12-21 | 2013-06-24 | Instytut Chemii Organicznej Polskiej Akademii Nauk | Nowe, fluorescencyjne barwniki heterocykliczne i sposób ich otrzymywania |
| GB201200184D0 (en) * | 2012-01-06 | 2012-02-22 | Johnson Matthey Plc | Tracers and method of marking liquids |
| KR101635332B1 (ko) * | 2012-09-26 | 2016-06-30 | 후지필름 가부시키가이샤 | 광전 변환 소자, 촬상 소자, 광 센서 |
| US9206180B2 (en) * | 2013-02-25 | 2015-12-08 | New York University | Superstructures of diketopyrrolopyrrole donors and perylenediimide acceptors formed by hydrogen-bonding and π•••π stacking |
| EP2818493A1 (en) | 2013-06-25 | 2014-12-31 | Basf Se | Near infrared absorbing polymers for electronic applications |
| CN105829454B (zh) * | 2013-12-19 | 2018-11-09 | 默克专利股份有限公司 | 染料化合物 |
| KR101704110B1 (ko) * | 2014-01-17 | 2017-02-07 | 주식회사 엘지화학 | 신규한 화합물 및 이를 포함하는 유기 태양 전지 |
| CN104447764A (zh) * | 2014-12-29 | 2015-03-25 | 华东理工大学 | 吡咯并吡咯二酮衍生物及其合成方法 |
| WO2017008880A1 (de) | 2015-07-10 | 2017-01-19 | Merck Patent Gmbh | Dithioalkylpyrrolopyrrole und ihre verwendung als farbstoffe |
| CN109897045B (zh) * | 2019-03-29 | 2021-04-27 | 华东理工大学 | 一种基于吡咯并吡咯二酮且具有固液双荧光的环状化合物及其制备方法与应用 |
| JP2022162560A (ja) * | 2021-01-26 | 2022-10-25 | 株式会社KOALA Tech | 有機固体レーザ、化合物およびその使用 |
| WO2024180566A1 (en) * | 2023-02-27 | 2024-09-06 | Council Of Scientific & Industrial Research | Polymerizable luminescent solvent-free organic liquids and the use thereof |
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| DE3262270D1 (en) * | 1981-03-20 | 1985-03-28 | Ciba Geigy Ag | Process for colouring highly molecular organic material and polycyclic pigments |
| US4585878A (en) | 1983-06-29 | 1986-04-29 | Ciba-Geigy Corporation | N-substituted 1,4-diketopyrrolo-[3,4-c]-pyrroles |
| US4931566A (en) | 1987-07-31 | 1990-06-05 | Ciba-Geigy Corporation | Process for the preparation of pyrrolo[3,4-c]pyrroles |
| JP2802338B2 (ja) * | 1988-07-29 | 1998-09-24 | リーデル―デ・ヘーン・アクチェンゲゼルシャフト | 新規の１，４−ジケトンピローロピロール染料 |
| EP0499011A1 (en) | 1991-02-12 | 1992-08-19 | Japat Ltd | Organic electroluminescent element |
| US5571359A (en) * | 1992-01-24 | 1996-11-05 | Revlon Consumer Products Corporation | Radiation curable pigmented compositions |
| DE4435211A1 (de) * | 1993-10-04 | 1995-04-27 | Ciba Geigy Ag | Substituierte Diketopyrrole und elektrochrome Stoffzusammensetzungen |
| DE59409351D1 (de) * | 1993-10-13 | 2000-06-21 | Ciba Sc Holding Ag | Pyrrolo[3,4-c]pyrrole |
| DE59506764D1 (de) | 1994-06-29 | 1999-10-14 | Ciba Sc Holding Ag | Zwei neue Kristallmodifikationen eines Diketopyrrolopyrrolpigments |
| 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 |
| US5969154A (en) | 1996-12-10 | 1999-10-19 | Ciba Specialty Chemicals Corporation | Liquid crystalline diketopyrrolopyrroles |
| WO1998033862A1 (en) | 1997-02-03 | 1998-08-06 | Ciba Speciality Chemicals Holding Inc. | Fluorescent materials and their use |
| EP0963425B1 (en) | 1997-02-03 | 2002-04-24 | Ciba SC Holding AG | Fluorescent compositions and their use |
| US6057449A (en) | 1998-06-02 | 2000-05-02 | Ciba Specialty Chemicals Corporation | Direct preparation of pyrrolo[3,4-c]pyrroles |
| EP1078970B1 (en) | 1999-08-26 | 2004-03-17 | Ciba SC Holding AG | DPP-containing conjugated polymers and electroluminescent devices |
| TWI290164B (en) | 1999-08-26 | 2007-11-21 | Ciba Sc Holding Ag | DPP-containing conjugated polymers and electroluminescent devices |
| TW503255B (en) * | 1999-09-27 | 2002-09-21 | Ciba Sc Holding Ag | Electroluminescent devices comprising diketopyrrolopyrroles |
| EP1329493A3 (en) | 1999-09-27 | 2007-05-23 | Ciba SC Holding AG | Electroluminescent devices comprising diketopyrrolopyrroles |
| EP1087005B1 (en) | 1999-09-27 | 2004-02-25 | Ciba SC Holding AG | Fluorescent diketopyrrolopyrroles |
| TWI261064B (en) | 1999-09-27 | 2006-09-01 | Ciba Sc Holding Ag | Fluorescent diketopyrrolopyrroles |
| JP4085574B2 (ja) * | 2000-01-06 | 2008-05-14 | 東レ株式会社 | 発光素子 |
| JP4312593B2 (ja) | 2001-06-29 | 2009-08-12 | チバ ホールディング インコーポレーテッド | 蛍光ジケトピロロピロール |
| 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 |
| KR101011941B1 (ko) | 2002-07-22 | 2011-02-08 | 시바 홀딩 인크 | 중합성 디케토피롤로피롤, 이의 칼라 필터에서의 용도 및이로부터 제조된 중합체 |
| JP2004175674A (ja) * | 2002-11-25 | 2004-06-24 | Toyo Ink Mfg Co Ltd | 有機エレクトロルミネッセンス素子材料およびそれを使用した有機エレクトロルミネッセンス素子 |
| JP3969300B2 (ja) * | 2002-12-24 | 2007-09-05 | 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組成物およびそれを使用した有機エレクトロルミネッセンス素子 |
| WO2004090046A1 (en) * | 2003-04-10 | 2004-10-21 | Ciba Specialty Chemicals Holding Inc. | Fluorescent diketopyrrolopyrroles |
-
2004
- 2004-04-01 WO PCT/EP2004/050403 patent/WO2004090046A1/en not_active Ceased
- 2004-04-01 US US10/551,976 patent/US7501076B2/en not_active Expired - Lifetime
- 2004-04-01 JP JP2006505506A patent/JP5068528B2/ja not_active Expired - Lifetime
- 2004-04-01 CN CN2004800094200A patent/CN1771298B/zh not_active Expired - Lifetime
- 2004-04-01 EP EP04725051.9A patent/EP1611207B1/en not_active Expired - Lifetime
- 2004-04-01 MX MXPA05010866A patent/MXPA05010866A/es unknown
- 2004-04-01 KR KR1020057019176A patent/KR101130094B1/ko not_active Expired - Lifetime
- 2004-04-09 TW TW093109926A patent/TWI347970B/zh not_active IP Right Cessation
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2009
- 2009-01-14 US US12/319,937 patent/US7906039B2/en not_active Expired - Lifetime
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- 2011-06-30 JP JP2011146241A patent/JP5523402B2/ja not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011225597A (ja) * | 2003-04-10 | 2011-11-10 | Ciba Holding Inc | 蛍光ジケトピロロピロール |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1611207A1 (en) | 2006-01-04 |
| MXPA05010866A (es) | 2006-06-05 |
| US7501076B2 (en) | 2009-03-10 |
| WO2004090046A1 (en) | 2004-10-21 |
| US20070010672A1 (en) | 2007-01-11 |
| JP5523402B2 (ja) | 2014-06-18 |
| KR20060002963A (ko) | 2006-01-09 |
| TW200502376A (en) | 2005-01-16 |
| CN1771298B (zh) | 2013-07-17 |
| JP2006524281A (ja) | 2006-10-26 |
| JP2011225597A (ja) | 2011-11-10 |
| TWI347970B (en) | 2011-09-01 |
| US7906039B2 (en) | 2011-03-15 |
| US20090173916A1 (en) | 2009-07-09 |
| KR101130094B1 (ko) | 2012-03-28 |
| CN1771298A (zh) | 2006-05-10 |
| EP1611207B1 (en) | 2016-02-03 |
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