JP6162231B2 - 量子ドット結合用リガンド及び組成物 - Google Patents
量子ドット結合用リガンド及び組成物 Download PDFInfo
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- JP6162231B2 JP6162231B2 JP2015518444A JP2015518444A JP6162231B2 JP 6162231 B2 JP6162231 B2 JP 6162231B2 JP 2015518444 A JP2015518444 A JP 2015518444A JP 2015518444 A JP2015518444 A JP 2015518444A JP 6162231 B2 JP6162231 B2 JP 6162231B2
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- 239000002096 quantum dot Substances 0.000 title claims description 143
- 239000003446 ligand Substances 0.000 title claims description 110
- 239000000203 mixture Substances 0.000 title claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 178
- 125000003118 aryl group Chemical group 0.000 claims description 60
- -1 -L- (R 2 ) q Chemical group 0.000 claims description 59
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 58
- 125000002947 alkylene group Chemical group 0.000 claims description 32
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 25
- 125000006649 (C2-C20) alkynyl group Chemical group 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 24
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 23
- 125000003342 alkenyl group Chemical group 0.000 claims description 23
- 125000000304 alkynyl group Chemical group 0.000 claims description 21
- 239000002086 nanomaterial Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000013078 crystal Substances 0.000 claims description 7
- 125000004474 heteroalkylene group Chemical group 0.000 claims description 7
- 230000008878 coupling Effects 0.000 claims 2
- 238000010168 coupling process Methods 0.000 claims 2
- 238000005859 coupling reaction Methods 0.000 claims 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 156
- 238000006243 chemical reaction Methods 0.000 description 141
- 239000000243 solution Substances 0.000 description 135
- 229920000642 polymer Polymers 0.000 description 73
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 69
- 229920001296 polysiloxane Polymers 0.000 description 64
- 239000002159 nanocrystal Substances 0.000 description 62
- 239000003054 catalyst Substances 0.000 description 61
- 239000000178 monomer Substances 0.000 description 59
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 56
- 238000004458 analytical method Methods 0.000 description 49
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 49
- 239000000047 product Substances 0.000 description 44
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 43
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 230000015572 biosynthetic process Effects 0.000 description 42
- 238000003786 synthesis reaction Methods 0.000 description 42
- 238000000034 method Methods 0.000 description 41
- 229910000077 silane Inorganic materials 0.000 description 35
- 229910052757 nitrogen Inorganic materials 0.000 description 32
- 239000003039 volatile agent Substances 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 238000005481 NMR spectroscopy Methods 0.000 description 29
- 239000001993 wax Substances 0.000 description 29
- 150000001412 amines Chemical class 0.000 description 27
- 238000002360 preparation method Methods 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 239000000463 material Substances 0.000 description 26
- 229910003460 diamond Inorganic materials 0.000 description 25
- 239000010432 diamond Substances 0.000 description 25
- 238000004821 distillation Methods 0.000 description 25
- 239000011159 matrix material Substances 0.000 description 25
- 229910052697 platinum Inorganic materials 0.000 description 24
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 23
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 22
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadecene Natural products CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 21
- 229920000548 poly(silane) polymer Polymers 0.000 description 21
- 238000000746 purification Methods 0.000 description 21
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 20
- UHYPYGJEEGLRJD-UHFFFAOYSA-N cadmium(2+);selenium(2-) Chemical compound [Se-2].[Cd+2] UHYPYGJEEGLRJD-UHFFFAOYSA-N 0.000 description 20
- 239000000523 sample Substances 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 19
- 230000003381 solubilizing effect Effects 0.000 description 18
- 239000011550 stock solution Substances 0.000 description 17
- 230000007306 turnover Effects 0.000 description 17
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 16
- 229910002808 Si–O–Si Inorganic materials 0.000 description 16
- 238000005102 attenuated total reflection Methods 0.000 description 16
- 239000011257 shell material Substances 0.000 description 16
- 238000010790 dilution Methods 0.000 description 15
- 239000012895 dilution Substances 0.000 description 15
- 125000005647 linker group Chemical group 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000010410 layer Substances 0.000 description 14
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 13
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 13
- 238000010438 heat treatment Methods 0.000 description 13
- 238000006459 hydrosilylation reaction Methods 0.000 description 13
- 229910052760 oxygen Inorganic materials 0.000 description 13
- 239000004593 Epoxy Substances 0.000 description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 12
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical class Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000001301 oxygen Substances 0.000 description 12
- 238000012546 transfer Methods 0.000 description 12
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 11
- 229910004613 CdTe Inorganic materials 0.000 description 11
- 239000004971 Cross linker Substances 0.000 description 11
- 150000001336 alkenes Chemical class 0.000 description 11
- 229910052793 cadmium Inorganic materials 0.000 description 11
- 235000011089 carbon dioxide Nutrition 0.000 description 11
- 229940038384 octadecane Drugs 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- GPXJNWSHGFTCBW-UHFFFAOYSA-N Indium phosphide Chemical compound [In]#P GPXJNWSHGFTCBW-UHFFFAOYSA-N 0.000 description 10
- 229920013822 aminosilicone Polymers 0.000 description 10
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 10
- 229910001873 dinitrogen Inorganic materials 0.000 description 10
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- CBFCDTFDPHXCNY-UHFFFAOYSA-N icosane Chemical compound CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 10
- 150000008064 anhydrides Chemical class 0.000 description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
- 239000011162 core material Substances 0.000 description 9
- 230000012010 growth Effects 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 230000003287 optical effect Effects 0.000 description 9
- 239000002245 particle Substances 0.000 description 9
- 239000004065 semiconductor Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- VEJOYRPGKZZTJW-FDGPNNRMSA-N (z)-4-hydroxypent-3-en-2-one;platinum Chemical compound [Pt].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O VEJOYRPGKZZTJW-FDGPNNRMSA-N 0.000 description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 238000004639 Schlenk technique Methods 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 8
- 150000001768 cations Chemical class 0.000 description 8
- NDJKXXJCMXVBJW-UHFFFAOYSA-N heptadecane Chemical compound CCCCCCCCCCCCCCCCC NDJKXXJCMXVBJW-UHFFFAOYSA-N 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 239000012299 nitrogen atmosphere Substances 0.000 description 8
- LQERIDTXQFOHKA-UHFFFAOYSA-N nonadecane Chemical compound CCCCCCCCCCCCCCCCCCC LQERIDTXQFOHKA-UHFFFAOYSA-N 0.000 description 8
- 239000002243 precursor Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 238000005070 sampling Methods 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 7
- WUMMIJWEUDHZCL-UHFFFAOYSA-N 3-prop-2-enyloxolane-2,5-dione Chemical compound C=CCC1CC(=O)OC1=O WUMMIJWEUDHZCL-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000006228 supernatant Substances 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- 239000004809 Teflon Substances 0.000 description 6
- 229920006362 Teflon® Polymers 0.000 description 6
- 150000003973 alkyl amines Chemical class 0.000 description 6
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 6
- PXLREXIFXBMRFT-UHFFFAOYSA-N dichloro(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[SiH](Cl)Cl PXLREXIFXBMRFT-UHFFFAOYSA-N 0.000 description 6
- 229910052738 indium Inorganic materials 0.000 description 6
- 230000014759 maintenance of location Effects 0.000 description 6
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 6
- YCOZIPAWZNQLMR-UHFFFAOYSA-N pentadecane Chemical compound CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 6
- 229910052711 selenium Inorganic materials 0.000 description 6
- 239000011669 selenium Chemical group 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- 229910052714 tellurium Inorganic materials 0.000 description 6
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 6
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 6
- 239000005052 trichlorosilane Substances 0.000 description 6
- IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical compound CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 6
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 230000006911 nucleation Effects 0.000 description 5
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 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 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- 229910017115 AlSb Inorganic materials 0.000 description 4
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- 125000005336 allyloxy group Chemical group 0.000 description 4
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- 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 4
- 230000001419 dependent effect Effects 0.000 description 4
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- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 3
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- 101150065749 Churc1 gene Proteins 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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- 125000003282 alkyl amino group Chemical group 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
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- 125000002619 bicyclic group Chemical group 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
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- 125000001165 hydrophobic group Chemical group 0.000 description 3
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 3
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- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical group CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
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- HSNUIYJWTSJUMS-UHFFFAOYSA-N sodium;trimethyl(oxido)silane Chemical compound [Na+].C[Si](C)(C)[O-] HSNUIYJWTSJUMS-UHFFFAOYSA-N 0.000 description 3
- 229940014800 succinic anhydride Drugs 0.000 description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 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
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- 229910052723 transition metal Inorganic materials 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- ADOBXTDBFNCOBN-UHFFFAOYSA-N 1-heptadecene Chemical compound CCCCCCCCCCCCCCCC=C ADOBXTDBFNCOBN-UHFFFAOYSA-N 0.000 description 2
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 2
- PJLHTVIBELQURV-UHFFFAOYSA-N 1-pentadecene Chemical compound CCCCCCCCCCCCCC=C PJLHTVIBELQURV-UHFFFAOYSA-N 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
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- 229910052715 tantalum Inorganic materials 0.000 description 1
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- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
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- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- YXFVVABEGXRONW-JGUCLWPXSA-N toluene-d8 Chemical compound [2H]C1=C([2H])C([2H])=C(C([2H])([2H])[2H])C([2H])=C1[2H] YXFVVABEGXRONW-JGUCLWPXSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
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- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
- C09K11/025—Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
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- 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
- C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
- C09K11/88—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing selenium, tellurium or unspecified chalcogen elements
- C09K11/881—Chalcogenides
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Description
この方法はまた、式IVの化合物と触媒とCH2=CH(CH2)pNR2aR2bとの反応混合物を形成させ、それによって式Iの化合物を生成させることも含む。式Ib、II、III及びIVについて、各R1は独立してC8-20アルキル、C8-20アルケニル、C8-20アルキニル、シクロアルキル又はアリールであることができ;各R2a及びR2bは独立してH又はC1-6アルキルであることができ;各R5は独立してC1-20アルキル、C2-20アルケニル、C2-20アルキニル、C3-8アルキル−NR2aR2b、シクロアルキル又はアリールであることができ;下付文字mは5〜50の整数であることができ;Mは水素又はカチオンであることができ;下付文字pは1〜6の整数であることができる。
I.概要
本発明は、量子ドットに結合させるためのシロキサンアミンワックス(SAW)を提供する。リガンドは複数個のアミン又はカルボキシ結合用基のせいで量子ドットについてより大きい安定性を提供する。
「シロキサンポリマー」又は「ポリシロキサン」とは、式−Si(R2)O−のモノマー繰返し単位を持つポリマーを指す。シロキサンポリマーのR基は同一であっても異なっていてもよく、任意の好適な基であることができ、例えば水素、アルキル、アルケニル、アルキニル、シクロアルキル、ヘテロシクロアルキル、アリール及びヘテロアリールを含むが、これらに限定されるわけではない。R基が両方とも水素以外である場合、このシロキサンポリマーは「シリコーン」と称することができる。シロキサンポリマーは、直鎖状、分岐鎖状又は環状であることができる。シロキサンポリマーは、単一のタイプのモノマー繰返し単位を含んでホモポリマーを形成することができる。シロキサンポリマーはまた、2つ以上のタイプのモノマー繰返し単位を含んでランダムコポリマー又はブロックコポリマーであることができるコポリマーを形成することもできる。
本発明は、量子ドット(QD)及び関連材料に結合させるためのシロキサンアミンワックス(SAW)を提供する。本発明のSAW材料は、ワックス状成分(長鎖アルキル)及びQDに結合することができる複数個のアミン又はカルボキシ基を含有し、得られるリガンド−QD錯体の安定性を改善する。
本発明の量子ドット結合用リガンドは、当業者に周知の任意の好適な手段によって調製することができる。例えば、商品として入手可能なシロキサンポリマーを(図1に示したように)一連の工程でアルケン及びアルケン−アミノでヒドロシリル化して、式Iにおいて下付文字nが0ではない量子ドット結合用リガンドを生成させることができる。また、長鎖アルキル官能化ジクロロシラン(RSi(Cl)2H)と水とを縮合させ、次いで該ポリマーの末端クロロ基をエンドキャップし、次いでシラン基を好適なアルケンアミンでヒドロシリル化することによってシロキサンポリマーを調製することもできる(図2)。図3には本発明の量子ドット結合用リガンドのさらに別の調製方法が示されている。図2に記載した方法に従って、第1工程で調製した二置換クロロシラン(1a)を分離し、シラノール(1b)に転化させ、次いでシロキサンポリマー(2)と反応させてエンドキャップされたシロキサンポリマー(3a)を生成させる。残りのシラン基を好適なアルケン及びKarstedt触媒を反応させて、図2の式の生成物と比較して2個の追加のアルキル−アミン基及び4個の追加の長鎖アルキル基を持つ最終生成物(4a)を調製する。残りの図面にも、本発明の量子ドット結合用リガンドの別の製造方法が記載されている。
この方法はまた、式IVの化合物と触媒とCH2=CH(CH2)pNR2aR2bとの反応混合物を形成させ、それによって式Iの化合物を生成させることも含む。式Ib、II、III及びIVについて、各R1は独立してC8-20アルキル、C8-20アルケニル、C8-20アルキニル、シクロアルキル又はアリールであることができ;各R2a及びR2bは独立してH又はC1-6アルキルであることができ;各R5は独立してC1-20アルキル、C2-20アルケニル、C2-20アルキニル、C3-8アルキル−NR2aR2b、シクロアルキル又はアリールであることができ;下付文字mは5〜50の整数であることができ;Mは水素又はカチオンであることができ;下付文字pは1〜6の整数であることができる。
本発明の量子ドット結合用リガンドは、量子ドット(QD)に錯化することができる。ある実施形態において、本発明は、本発明の量子ドット結合用リガンドと、発光量子ドット(QD)の第1の母集団との組成物を提供する。
量子ドット
マトリックス材料
VI.実施例
この実施例は、比1:1のアルキルアミン(アミノプロピル)と長鎖アルキル(オクタデシル)を含むポリマー性シリコーンアミンワックス(PSAW)を生成する方法を提供する。
ポリマー性シリコーンアミンワックス(3)の合成
この実施例は、先の実施例1に記載した手順を使用して、比1:2のアルキルアミン(アミノプロピル)と長鎖アルキル(オクタデシル)を含むポリマー性シリコーンアミンワックス(PSAW)を生成する方法を提供する。例えば、シランポリマーHMS−991(10g、10.2mL、6.25ミリモルのポリマー鎖と150ミリモルのシラン)では、1−オクタデセン(25.3g、32.0mL、100ミリモル)およびアリルアミン(11.4g、15.0mL、200ミリモル)を使用した。したがってKarstedt触媒も、白金を使用して、第1のステップでは20,000回のターンオーバー(0.0050ミリモル)、次に第2のステップでは1000回のターンオーバー(0.050ミリモル)(302−071)に合わせて見積もった。
この実施例は、先の実施例1に記載した手順を使用して、比2:1のアルキルアミン(アミノプロピル)と長鎖アルキル(オクタデシル)を含むポリマー性シリコーンアミンワックス(PSAW)を生成する方法を提供する。例えば、シランポリマーHMS−991(10g、10.2mL、6.25ミリモルのポリマー鎖と150ミリモルのシラン)では、1−オクタデセン(12.6g、16.0mL、50ミリモル)およびアリルアミン(22.8g、30.0mL、400ミリモル)を使用した。したがってKarstedt触媒も、白金を使用して、第1のステップでは20,000回のターンオーバー(0.0025ミリモル)、次に第2のステップでは1000回のターンオーバー(0.10ミリモル)(302−075)に合わせて見積もった。
この実施例では、各モノマー単位上に長鎖アルキル基およびアルキルアミン基の両方を有するオリゴマー性シリコーンアミンワックス(OSAW)の調製を記載する。
オクタデシルジクロロシラン(1)の合成
オリゴマー性シラン(3)の合成
オリゴマー性シリコーンアミンワックスまたはOSAW(4)の合成
リガンド交換は、ナノ結晶/量子ドットをヘキサンまたはトルエンに溶解させ、アミノ官能性シリコーンを添加し、50℃〜60℃で16〜36時間加熱し、真空搬送によって揮発物を除去することによって完遂した。(一般に、リガンド交換は、典型的に50℃〜130℃において2〜72時間で完遂される)。量子収率および他のパラメータを維持すると、ナノ結晶は透明油としてシリコーン中に残った。
この実施例は、異なるモノマー単位上に長鎖アルキル基およびアルキルカルボン酸基を有するポリマー性シリコーンワックス(PSAW)の合成を記載している。
この実施例は、シリコーン骨格上の異なる繰り返し単位上に長鎖アルキル基およびアルキルジカルボン酸基を有するポリマー性シリコーンアミンワックスを生成する方法を提供する。
この実施例では、同じモノマー繰り返し単位上に長鎖アルキル基およびアルキルカルボン酸の両方を有するオリゴマー性シリコーンワックス(OSCAW)の調製を記載する。
オリゴマー性シリコーンカルボン酸ワックスまたはOSCAWの合成
この実施例は、同じオリゴマー繰り返し単位上に長鎖アルキル基およびアルキルジカルボン酸基を有するシリコーンオリゴマーであるオリゴマー性シリコーンジカルボン酸ワックス(OS2CAW)の合成を記載する。OS2CAWは、2つの方法を使用して合成した。第1の方法では、ワックス状シラン4(上記合成を参照されたい)で開始し、次にヒドロシリル化(hydrosilation)によってオリゴマー鎖上にジカルボン酸を配置する。第2の方法では、シリコーンに既に付着した無水物(ジカルボン酸前駆体)を含むシリコーンオリゴマーを構築する。全体的に、第2の方法は、第1の方法よりも少ないステップを有する。
方法1
方法2
この実施例では、シリコーン骨格の異なる繰り返し単位上にプロピルエチレンオキシドおよびアルキルジカルボン酸を含む短鎖ポリマー性シリコーンの調製を記載する。
PSAW−Si(R)3の調製は、図5に示されており、実施例1に記載のPSAWの調製手順に従って、オクタデセンの代わりにトリエチル(オクタデカ−1−エン−9−イル)シランを使用して行う。
オリゴマーシリコーントリカルボン酸(OS3CAW)の調製を以下で説明する。
これらのリガンド中のトリメチルシリル末端基は、シリコーン主鎖の繰り返し単位のようにさらなるナノ結晶結合または可溶化を一切もたらさない。したがって、この無能を補正するために、シリコーン主鎖の末端におけるナノ結晶結合および可溶化基を有するリガンドを考案した。その合成を、OSAWに適応させて以下に示す。
PSAW−1:1を有するナノ結晶組成物を、上で説明したように調製した。
Claims (15)
- 式I:
(ここで、
R1及びR4の少なくとも一方は、C8-20アルキル及びC8-20ヘテロアルキルより成る群から選択され、各アルキル基は、1個の−Si(R1a)3基で随意に置換されていてよく;
各R1aは独立してC1-6アルキル、シクロアルキル及びアリールより成る群から選択され;
各Lは独立してC3-8アルキレン、C3-8ヘテロアルキレン、C3-8アルキレン−O−C2-8アルキレン、C3-8アルキレン−(C(O)NH−C2-8アルキレン)q、C3-8ヘテロアルキレン−(C(O)NH−C2-8アルキレン)q及びC3-8アルキレン−O−C1-8アルキレン−(C(O)NH−C2-8アルキレン)qより成る群から選択され;
各R2は独立してNR2aR2b及びC(O)OHより成る群から選択され;
各R2a及びR2bは独立してH及びC1-6アルキルより成る群から選択され;
各R3は独立してC1-20アルキル、C2-20アルケニル、C2-20アルキニル、シクロアルキル及びアリールより成る群から選択され;
各R5は独立してC1-20アルキル、C2-20アルケニル、C2-20アルキニル、−L−(R2)q、シクロアルキル及びアリールより成る群から選択され;
下付文字mは5〜50の整数であり;
下付文字nは0〜50の整数であり;
下付文字qは1〜10の整数であり;
下付文字nが0である場合、R1はC8-20アルキル、C8-20ヘテロアルキル、C8-20アルケニル、C8-20アルキニル、シクロアルキル及びアリールより成る群から選択され、これらはそれぞれ1個以上の−Si(R1a)3基で随意に置換されていてよい)
の構造を含む、量子ドット結合用リガンドであり、
前記量子ドットとは、実質的に単結晶であり、約500nm未満の寸法の少なくとも1つの領域又は特徴的寸法を有するナノ構造体である、
量子ドット結合用リガンド。 - R1及びR4の少なくとも1つがC16アルキル、C18アルキル、C20アルキル及び−(CH2)2−(OCH2CH2)3−OCH3より成る群から選択され、各アルキル基が随意に1個の−Si(R1a)3基で置換されていてよい、請求項1に記載の量子ドット結合用リガンド。
- 各R5が独立してC1-20アルキル、C2-20アルケニル、C2-20アルキニル、シクロアルキル及びアリールより成る群から選択され;
下付文字mが5〜50の整数であり;
下付文字nが1〜50の整数である:
請求項1に記載の量子ドット結合用リガンド。 - 下付文字m対下付文字nの比が約2:1である、請求項1に記載の量子ドット結合用リガンド。
- 下付文字m対下付文字nの比が約1:1である、請求項1に記載の量子ドット結合用リガンド。
- 下付文字m対下付文字nの比が約1:2である、請求項1に記載の量子ドット結合用リガンド。
- R1及びR3がそれぞれ独立してC1-3アルキルであり;
各R1aが独立してC1-6アルキルであり;
各R4が独立してC8-20アルキル及びC8-20ヘテロアルキルより成る群から選択され、該アルキル基が1個の−Si(R1a)3基で随意に置換されていてよく;
各R5が独立してC1-3アルキルであり;
下付文字qが1〜3の整数である:
請求項1に記載の量子ドット結合用リガンド。 - 次式:
(ここで、下付文字m及びnはそれぞれ10〜14の整数である)
の構造を有する、請求項7に記載の量子ドット結合用リガンド。 - 次式:
(ここで、各R1aは独立してC1-6アルキルであり、
下付文字m及びnはぞれぞれ10〜14の整数である)
より成る群から選択される構造を有する、請求項7に記載の量子ドット結合用リガンド。 - 各R5が独立してC1-20アルキル、C2-20アルケニル、C2-20アルキニル、シクロアルキル及びアリールより成る群から選択され、該アルキル基が1個の−Si(R1a)3基で随意に置換されていてよく;
下付文字mが5〜50の整数であり;
下付文字nが0である:
請求項1に記載の量子ドット結合用リガンド。 - 次式:
の構造を有する、請求項10に記載の量子ドット結合用リガンド。 - R1がC8-20アルキルである、請求項11に記載の量子ドット結合用リガンド。
- 次式:
(ここで、下付文字mは5〜50の整数である)
より成る群から選択される構造を有する、請求項10に記載の量子ドット結合用リガンド。 - 請求項1に記載の量子ドット結合用リガンドと、発光量子ドット(QD)の第1の母集団とを含む組成物。
- 前記量子ドット結合用リガンドが次式:
の構造を含む、請求項14に記載の組成物。
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