JP2010525122A - フッ素化染料および電気泳動ディスプレイ装置におけるそれらの使用 - Google Patents
フッ素化染料および電気泳動ディスプレイ装置におけるそれらの使用 Download PDFInfo
- Publication number
- JP2010525122A JP2010525122A JP2010504626A JP2010504626A JP2010525122A JP 2010525122 A JP2010525122 A JP 2010525122A JP 2010504626 A JP2010504626 A JP 2010504626A JP 2010504626 A JP2010504626 A JP 2010504626A JP 2010525122 A JP2010525122 A JP 2010525122A
- Authority
- JP
- Japan
- Prior art keywords
- group
- aryl
- heteroaryl
- heteroalkyl
- groups
- 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
- 239000000975 dye Substances 0.000 title claims abstract description 34
- 150000001875 compounds Chemical class 0.000 claims abstract description 123
- 238000000034 method Methods 0.000 claims abstract description 44
- 239000000203 mixture Substances 0.000 claims abstract description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 27
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 8
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims description 94
- 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 claims description 91
- 125000001072 heteroaryl group Chemical group 0.000 claims description 77
- 239000001257 hydrogen Substances 0.000 claims description 63
- 229910052739 hydrogen Inorganic materials 0.000 claims description 63
- 150000002431 hydrogen Chemical class 0.000 claims description 52
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- 125000004432 carbon atom Chemical group C* 0.000 claims description 43
- 229920006395 saturated elastomer Polymers 0.000 claims description 42
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 37
- 229910052736 halogen Inorganic materials 0.000 claims description 32
- 150000002367 halogens Chemical class 0.000 claims description 32
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000006413 ring segment Chemical group 0.000 claims description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 21
- 125000001624 naphthyl group Chemical group 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 125000005647 linker group Chemical group 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 125000006735 (C1-C20) heteroalkyl group Chemical group 0.000 claims description 8
- 125000000524 functional group Chemical group 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 150000002736 metal compounds Chemical class 0.000 claims description 3
- 125000006539 C12 alkyl 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([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 235000019000 fluorine Nutrition 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 12
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 150000003949 imides Chemical class 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical group CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 239000006185 dispersion Substances 0.000 description 8
- 238000001906 matrix-assisted laser desorption--ionisation mass spectrometry Methods 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- 229910052786 argon Inorganic materials 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 125000003709 fluoroalkyl group Chemical group 0.000 description 5
- 125000005462 imide group Chemical group 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- -1 perfluoroalkyl iodide Chemical compound 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 229910000071 diazene Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 3
- 239000000539 dimer Substances 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000010702 perfluoropolyether Substances 0.000 description 3
- USPWUOFNOTUBAD-UHFFFAOYSA-N 1,2,3,4,5-pentafluoro-6-(trifluoromethyl)benzene Chemical compound FC1=C(F)C(F)=C(C(F)(F)F)C(F)=C1F USPWUOFNOTUBAD-UHFFFAOYSA-N 0.000 description 2
- UWTFGHPTJQPZQP-UHFFFAOYSA-N 1,2,3,4-tetrafluoro-5,6-bis(trifluoromethyl)benzene Chemical group FC1=C(F)C(F)=C(C(F)(F)F)C(C(F)(F)F)=C1F UWTFGHPTJQPZQP-UHFFFAOYSA-N 0.000 description 2
- IYDIZBOKVLHCQZ-UHFFFAOYSA-N 9-(9-borabicyclo[3.3.1]nonan-9-yl)-9-borabicyclo[3.3.1]nonane Chemical compound C1CCC2CCCC1B2B1C2CCCC1CCC2 IYDIZBOKVLHCQZ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 238000007630 basic procedure Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 2
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 2
- 229910052734 helium Inorganic materials 0.000 description 2
- 239000001307 helium Substances 0.000 description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 2
- ZQBFAOFFOQMSGJ-UHFFFAOYSA-N hexafluorobenzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1F ZQBFAOFFOQMSGJ-UHFFFAOYSA-N 0.000 description 2
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052756 noble gas Inorganic materials 0.000 description 2
- 229960004624 perflexane Drugs 0.000 description 2
- 229950011087 perflunafene Drugs 0.000 description 2
- UWEYRJFJVCLAGH-IJWZVTFUSA-N perfluorodecalin Chemical compound FC1(F)C(F)(F)C(F)(F)C(F)(F)[C@@]2(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)[C@@]21F UWEYRJFJVCLAGH-IJWZVTFUSA-N 0.000 description 2
- ZJIJAJXFLBMLCK-UHFFFAOYSA-N perfluorohexane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F ZJIJAJXFLBMLCK-UHFFFAOYSA-N 0.000 description 2
- AQZYBQIAUSKCCS-UHFFFAOYSA-N perfluorotripentylamine Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)N(C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F AQZYBQIAUSKCCS-UHFFFAOYSA-N 0.000 description 2
- CLYVDMAATCIVBF-UHFFFAOYSA-N pigment red 224 Chemical compound C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)OC(=O)C4=CC=C3C1=C42 CLYVDMAATCIVBF-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- KWXGJTSJUKTDQU-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-heptadecafluoro-8-iodooctane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)I KWXGJTSJUKTDQU-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DFUYAWQUODQGFF-UHFFFAOYSA-N 1-ethoxy-1,1,2,2,3,3,4,4,4-nonafluorobutane Chemical compound CCOC(F)(F)C(F)(F)C(F)(F)C(F)(F)F DFUYAWQUODQGFF-UHFFFAOYSA-N 0.000 description 1
- KQDJTBPASNJQFQ-UHFFFAOYSA-N 2-iodophenol Chemical compound OC1=CC=CC=C1I KQDJTBPASNJQFQ-UHFFFAOYSA-N 0.000 description 1
- PFINVJYJNJHTFY-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecan-1-amine Chemical compound NCCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F PFINVJYJNJHTFY-UHFFFAOYSA-N 0.000 description 1
- AMKGKYQBASDDJB-UHFFFAOYSA-N 9$l^{2}-borabicyclo[3.3.1]nonane Chemical group C1CCC2CCCC1[B]2 AMKGKYQBASDDJB-UHFFFAOYSA-N 0.000 description 1
- FEJUGLKDZJDVFY-UHFFFAOYSA-N 9-borabicyclo[3.3.1]nonane Substances C1CCC2CCCC1B2 FEJUGLKDZJDVFY-UHFFFAOYSA-N 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical class C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 101100049641 Caenorhabditis elegans pfs-2 gene Proteins 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical group N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- YMEPVPIIHONYLV-UHFFFAOYSA-N O=C(c(cc1)c(c-2ccc3-c4nc(cccc5)c5[n]44)c3c1C4=O)[n]1c-2nc2ccccc12 Chemical compound O=C(c(cc1)c(c-2ccc3-c4nc(cccc5)c5[n]44)c3c1C4=O)[n]1c-2nc2ccccc12 YMEPVPIIHONYLV-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical group N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 239000012080 ambient air Substances 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical class C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000000879 imine group Chemical group 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- AGJSNMGHAVDLRQ-HUUJSLGLSA-N methyl (2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,3-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoate Chemical compound SC[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@@H](CCSC)C(=O)OC)CC1=CC=C(O)C(C)=C1C AGJSNMGHAVDLRQ-HUUJSLGLSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- RVZRBWKZFJCCIB-UHFFFAOYSA-N perfluorotributylamine Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)N(C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F RVZRBWKZFJCCIB-UHFFFAOYSA-N 0.000 description 1
- 150000002979 perylenes Chemical group 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical class C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002493 poly(chlorotrifluoroethylene) Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000004032 porphyrins Chemical group 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 235000021003 saturated fats Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 235000021081 unsaturated fats Nutrition 0.000 description 1
- 238000005406 washing Methods 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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/62—Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/165—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on translational movement of particles in a fluid under the influence of an applied field
- G02F1/166—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on translational movement of particles in a fluid under the influence of an applied field characterised by the electro-optical or magneto-optical effect
- G02F1/167—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on translational movement of particles in a fluid under the influence of an applied field characterised by the electro-optical or magneto-optical effect by electrophoresis
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Nonlinear Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07106784 | 2007-04-24 | ||
| PCT/EP2008/054589 WO2008128934A2 (en) | 2007-04-24 | 2008-04-16 | Fluorinated dyes and their use in electrophoretic display devices |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010525122A true JP2010525122A (ja) | 2010-07-22 |
| JP2010525122A5 JP2010525122A5 (cg-RX-API-DMAC7.html) | 2011-06-02 |
Family
ID=39722489
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010504626A Pending JP2010525122A (ja) | 2007-04-24 | 2008-04-16 | フッ素化染料および電気泳動ディスプレイ装置におけるそれらの使用 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8119802B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2150585A2 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2010525122A (cg-RX-API-DMAC7.html) |
| KR (1) | KR20100017341A (cg-RX-API-DMAC7.html) |
| CN (1) | CN101730723A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2008128934A2 (cg-RX-API-DMAC7.html) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8582199B2 (en) | 2011-12-15 | 2013-11-12 | Fujifilm Corporation | Electrophoretic composition, microcapsule and electrophoretic display device |
| WO2014010305A1 (ja) * | 2012-07-09 | 2014-01-16 | シャープ株式会社 | 化合物、太陽電池モジュール及び太陽光発電装置 |
| WO2014132929A1 (ja) * | 2013-02-27 | 2014-09-04 | シャープ株式会社 | 化合物、太陽電池モジュール及び太陽光発電装置 |
| JP2016175864A (ja) * | 2015-03-20 | 2016-10-06 | 国立大学法人山口大学 | パーフルオロアルキル基を有するホスファゼン化合物 |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8697255B2 (en) | 2007-07-05 | 2014-04-15 | Basf Se | Organic light-emitting diodes comprising at least one disilyl compound selected from disilylcarbazoles, disilyldibenzofurans, disilyldibenzothiophenes, disilyldibenzopholes, disilyldibenzothiophene S-oxides and disilyldibenzothiophene S,S-dioxides |
| EP2246350A1 (de) | 2009-04-15 | 2010-11-03 | LANXESS Deutschland GmbH | Fluor-substituierte Perylene für Farbfilter in LCD |
| EP2704683B1 (en) | 2011-05-06 | 2017-10-18 | Basf Se | Chromophores with perfluoroalkyl substituents |
| US8993713B1 (en) * | 2012-05-16 | 2015-03-31 | The United States Of America As Represented By The Secretary Of The Navy | Solution processable n-type ladder polymer for hetero-junction devices |
| US8816081B2 (en) | 2012-08-06 | 2014-08-26 | Basf Se | Boron containing perylene monoimides, a process for their production, their use as building blocks for the production of perylene monoimide derivatives, monoimide derivatives and their use in dye-sensitized solar cells |
| AU2013301239A1 (en) * | 2012-08-06 | 2015-02-05 | Basf Se | Boron containing perylene monoimides, process for their production, their use as building blocks for production of perylene monoimide derivatives, monoimide derivatives and their use in dye-sensitized solar cells |
| EP2976316A4 (en) * | 2013-03-18 | 2016-11-16 | Basf Se | PERYLENE MONOIDIDE AND NAPHTHALENE MONOMIDE DERIVATIVES AND THEIR USE IN COLOR-SENSITIZED SOLAR CELLS |
| US10324353B2 (en) | 2013-10-22 | 2019-06-18 | Vlyte Innovations Limited | Wide operating temperature range electrophoretic device |
| CN110268317B (zh) | 2017-02-15 | 2022-10-21 | 伊英克加利福尼亚有限责任公司 | 用于彩色电泳显示介质的聚合物添加剂 |
| US9995987B1 (en) | 2017-03-20 | 2018-06-12 | E Ink Corporation | Composite particles and method for making the same |
| CN110785699B (zh) | 2017-06-16 | 2023-07-04 | 伊英克公司 | 可变透射电泳装置 |
| US10983410B2 (en) | 2017-06-16 | 2021-04-20 | E Ink Corporation | Electro-optic media including encapsulated pigments in gelatin binder |
| JP7001217B2 (ja) | 2017-12-22 | 2022-01-19 | イー インク コーポレイション | 電気泳動表示装置、および電子機器 |
| KR102539870B1 (ko) * | 2018-09-12 | 2023-06-05 | 동우 화인켐 주식회사 | 자발광 감광성 수지 조성물, 이를 이용한 색변환층을 포함하는 컬러필터 및 화상표시장치 |
| WO2020176193A1 (en) | 2019-02-25 | 2020-09-03 | E Ink Corporation | Composite electrophoretic particles and variable transmission films containing the same |
| GB201914105D0 (en) | 2019-09-30 | 2019-11-13 | Vlyte Innovations Ltd | A see-through electrophoretic device having a visible grid |
| CN115260197B (zh) * | 2022-07-14 | 2024-03-12 | 深圳市国华光电研究院 | 一种稠环化合物及其制备方法和应用 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005017046A2 (en) * | 2003-08-08 | 2005-02-24 | Sipix Imaging, Inc. | Fluorinated dyes or colorants and their uses |
| JP2005208621A (ja) * | 2003-12-26 | 2005-08-04 | Canon Inc | 電子写真感光体、プロセスカートリッジおよび電子写真装置 |
| JP2006008888A (ja) * | 2004-06-28 | 2006-01-12 | Nippon Steel Chem Co Ltd | 液状エポキシ樹脂組成物 |
| WO2006025274A1 (ja) * | 2004-08-30 | 2006-03-09 | Kyoto University | 有機半導体発光装置およびそれを用いた表示装置 |
| JP2007192903A (ja) * | 2006-01-17 | 2007-08-02 | Canon Inc | 電子写真感光体、プロセスカートリッジ、および電子写真装置 |
| WO2007093643A1 (de) * | 2006-02-17 | 2007-08-23 | Basf Se | Fluorierte rylentetracarbonsäurederivate und deren verwendung |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3281426A (en) | 1961-05-01 | 1966-10-25 | Minnesota Mining & Mfg | Perfluoroalkylated phthalic anhydride, copper phthalocyanine and their preparation |
| DE19547210A1 (de) | 1995-12-18 | 1997-06-19 | Basf Ag | 1,7-Disubstituierte Perylen-3,4,9-10-tetracarbonsäuren, deren Dianhydride und Diimide |
| DE19547209A1 (de) | 1995-12-18 | 1997-06-19 | Basf Ag | 1,7-Diaroxy-oder -arylthiosubstituierte Perylen-3,4,9,10-tetracarbonsäuren, deren Dianhydride und Diimide |
| JP2007199400A (ja) * | 2006-01-26 | 2007-08-09 | Kyocera Mita Corp | 電子写真感光体 |
| CN101139351A (zh) * | 2007-09-03 | 2008-03-12 | 大连理工大学 | 全氟烷基取代的苝双二亚胺及其衍生物和制备方法 |
-
2007
- 2007-08-29 US US11/846,969 patent/US8119802B2/en not_active Expired - Fee Related
-
2008
- 2008-04-16 EP EP08736268A patent/EP2150585A2/en not_active Ceased
- 2008-04-16 JP JP2010504626A patent/JP2010525122A/ja active Pending
- 2008-04-16 KR KR1020097024515A patent/KR20100017341A/ko not_active Ceased
- 2008-04-16 WO PCT/EP2008/054589 patent/WO2008128934A2/en not_active Ceased
- 2008-04-16 CN CN200880021608A patent/CN101730723A/zh active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005017046A2 (en) * | 2003-08-08 | 2005-02-24 | Sipix Imaging, Inc. | Fluorinated dyes or colorants and their uses |
| JP2005208621A (ja) * | 2003-12-26 | 2005-08-04 | Canon Inc | 電子写真感光体、プロセスカートリッジおよび電子写真装置 |
| JP2006008888A (ja) * | 2004-06-28 | 2006-01-12 | Nippon Steel Chem Co Ltd | 液状エポキシ樹脂組成物 |
| WO2006025274A1 (ja) * | 2004-08-30 | 2006-03-09 | Kyoto University | 有機半導体発光装置およびそれを用いた表示装置 |
| JP2007192903A (ja) * | 2006-01-17 | 2007-08-02 | Canon Inc | 電子写真感光体、プロセスカートリッジ、および電子写真装置 |
| WO2007093643A1 (de) * | 2006-02-17 | 2007-08-23 | Basf Se | Fluorierte rylentetracarbonsäurederivate und deren verwendung |
| JP2009528277A (ja) * | 2006-02-17 | 2009-08-06 | ビーエーエスエフ ソシエタス・ヨーロピア | フッ素化されたリレンテトラカルボン酸誘導体及びそれらの使用 |
Non-Patent Citations (2)
| Title |
|---|
| ANGEW. CHEM. INT. ED., vol. 43, JPN6013028841, 2004, pages 6363 - 6366, ISSN: 0002557542 * |
| DYES AND PIGMENTS, vol. 30, no. 1, JPN6013028839, 1996, pages 73 - 78, ISSN: 0002557541 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8582199B2 (en) | 2011-12-15 | 2013-11-12 | Fujifilm Corporation | Electrophoretic composition, microcapsule and electrophoretic display device |
| WO2014010305A1 (ja) * | 2012-07-09 | 2014-01-16 | シャープ株式会社 | 化合物、太陽電池モジュール及び太陽光発電装置 |
| JPWO2014010305A1 (ja) * | 2012-07-09 | 2016-06-20 | シャープ株式会社 | 化合物、太陽電池モジュール及び太陽光発電装置 |
| WO2014132929A1 (ja) * | 2013-02-27 | 2014-09-04 | シャープ株式会社 | 化合物、太陽電池モジュール及び太陽光発電装置 |
| JPWO2014132929A1 (ja) * | 2013-02-27 | 2017-02-02 | シャープ株式会社 | 化合物、太陽電池モジュール及び太陽光発電装置 |
| JP2016175864A (ja) * | 2015-03-20 | 2016-10-06 | 国立大学法人山口大学 | パーフルオロアルキル基を有するホスファゼン化合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| US8119802B2 (en) | 2012-02-21 |
| KR20100017341A (ko) | 2010-02-16 |
| WO2008128934A3 (en) | 2008-12-18 |
| US20080269485A1 (en) | 2008-10-30 |
| EP2150585A2 (en) | 2010-02-10 |
| WO2008128934A2 (en) | 2008-10-30 |
| CN101730723A (zh) | 2010-06-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2010525122A (ja) | フッ素化染料および電気泳動ディスプレイ装置におけるそれらの使用 | |
| CN1263744C (zh) | 用于制备取代的荂四羧酸二酰亚胺的中间体 | |
| JP2007533773A (ja) | フッ素化染料又は着色剤及びそれらの使用 | |
| CN110156550B (zh) | 一种使用苯酚类催化剂进行氟烷基化的方法 | |
| EP2110369A1 (en) | Method of synthesizing 9-aryl-10-iodoanthracene derivative and light-emitting material | |
| JP6572498B2 (ja) | フラーレン誘導体の製造方法 | |
| Ozser et al. | Novel derivatives of regioisomerically pure 1, 7-disubstituted perylene diimide dyes bearing phenoxy and pyrrolidinyl substituents: Synthesis, photophysical, thermal, and structural properties | |
| KR20170034573A (ko) | 수용해성을 증가시킨 프탈로시아닌 유도체 및 이의 제조 방법 | |
| WO2021095878A1 (ja) | フルオロポリエーテル基含有化合物の製造方法 | |
| Yamasaki et al. | μ-Oxo-Bridged Subphthalocyanine Dimers: Preparation and Characterization by X-ray Structure Analysis | |
| US20240425371A1 (en) | Working solution for producing hydrogen peroxide through anthraquinone process and solvent system thereof | |
| JP2015040176A (ja) | ビス−ボロンジピロメテン系色素 | |
| JP5092140B2 (ja) | 非対称型ビス（ターピリジン）化合物の合成方法 | |
| JP3575704B2 (ja) | ジオキサジン化合物の製造法 | |
| TWI889186B (zh) | 具有軸向芳基的三苯三戊並烯及其製備方法 | |
| CN120289410B (zh) | 一种呫吨染料的合成方法 | |
| TWI854775B (zh) | 雙馬來醯亞胺單體及其製備方法 | |
| JP4038140B2 (ja) | フッ素系媒体中の反応及び分離方法 | |
| JP6915740B2 (ja) | フルオロポリエーテル基含有化合物の製造方法 | |
| CN111848491B (zh) | 1-甲酰基咔唑的制备方法 | |
| CN113816974A (zh) | 一种卟啉共价连接均三氮杂蔻化合物及其制备和应用 | |
| JP5651037B2 (ja) | ｔｅｔｒａｋｉｓ−アリル置換フタロシアニンおよびその製造方法 | |
| JP6439219B2 (ja) | 含フッ素フェノールの製造法 | |
| JPH0782495A (ja) | フルオロアルキル基含有ナイルレッド化合物及びその製造方法 | |
| CN118146263A (zh) | 二腈基乙烯和三苯基膦封端的醌式化合物及其制备方法和应用 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20101228 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20110413 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20110413 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130617 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20130917 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20140507 |