JP2011513508A - 半導体ナノ粒子キャッピング剤 - Google Patents
半導体ナノ粒子キャッピング剤 Download PDFInfo
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- JP2011513508A JP2011513508A JP2010547252A JP2010547252A JP2011513508A JP 2011513508 A JP2011513508 A JP 2011513508A JP 2010547252 A JP2010547252 A JP 2010547252A JP 2010547252 A JP2010547252 A JP 2010547252A JP 2011513508 A JP2011513508 A JP 2011513508A
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- 239000002105 nanoparticle Substances 0.000 title claims abstract description 89
- 239000004065 semiconductor Substances 0.000 title claims abstract description 34
- 239000003446 ligand Substances 0.000 claims abstract description 47
- 238000000034 method Methods 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 21
- 239000007858 starting material Substances 0.000 claims abstract description 18
- 125000000524 functional group Chemical group 0.000 claims abstract description 5
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 5
- 239000000463 material Substances 0.000 claims description 35
- 239000002904 solvent Substances 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 5
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 150000003573 thiols Chemical class 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000002243 precursor Substances 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000003636 chemical group Chemical group 0.000 claims 6
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 230000009920 chelation Effects 0.000 abstract 1
- 239000011162 core material Substances 0.000 description 30
- 239000002096 quantum dot Substances 0.000 description 19
- 239000011257 shell material Substances 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 13
- VIBDJEWPNNCFQO-UHFFFAOYSA-N ethane-1,1,2-triol Chemical compound OCC(O)O VIBDJEWPNNCFQO-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 150000002500 ions Chemical class 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000006862 quantum yield reaction Methods 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
- 239000002245 particle Substances 0.000 description 4
- 230000006798 recombination Effects 0.000 description 4
- 238000005215 recombination Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 230000007547 defect Effects 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- DGFLVXIQGRFWHJ-UHFFFAOYSA-N methoxymethane;4-methylbenzenesulfonic acid Chemical compound COC.CC1=CC=C(S(O)(=O)=O)C=C1 DGFLVXIQGRFWHJ-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- 229910001218 Gallium arsenide Inorganic materials 0.000 description 2
- 229910000673 Indium arsenide Inorganic materials 0.000 description 2
- GPXJNWSHGFTCBW-UHFFFAOYSA-N Indium phosphide Chemical compound [In]#P GPXJNWSHGFTCBW-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- TUVYSBJZBYRDHP-UHFFFAOYSA-N acetic acid;methoxymethane Chemical compound COC.CC(O)=O TUVYSBJZBYRDHP-UHFFFAOYSA-N 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- UHYPYGJEEGLRJD-UHFFFAOYSA-N cadmium(2+);selenium(2-) Chemical compound [Se-2].[Cd+2] UHYPYGJEEGLRJD-UHFFFAOYSA-N 0.000 description 2
- 239000002800 charge carrier Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000011258 core-shell material Substances 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- RPQDHPTXJYYUPQ-UHFFFAOYSA-N indium arsenide Chemical compound [In]#[As] RPQDHPTXJYYUPQ-UHFFFAOYSA-N 0.000 description 2
- 229920001427 mPEG Polymers 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000000737 periodic effect Effects 0.000 description 2
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 238000006557 surface reaction Methods 0.000 description 2
- ZMBHCYHQLYEYDV-UHFFFAOYSA-N trioctylphosphine oxide Chemical compound CCCCCCCCP(=O)(CCCCCCCC)CCCCCCCC ZMBHCYHQLYEYDV-UHFFFAOYSA-N 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- YBNMDCCMCLUHBL-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-pyren-1-ylbutanoate Chemical compound C=1C=C(C2=C34)C=CC3=CC=CC4=CC=C2C=1CCCC(=O)ON1C(=O)CCC1=O YBNMDCCMCLUHBL-UHFFFAOYSA-N 0.000 description 1
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- 229910017115 AlSb Inorganic materials 0.000 description 1
- JBRZTFJDHDCESZ-UHFFFAOYSA-N AsGa Chemical compound [As]#[Ga] JBRZTFJDHDCESZ-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- YXPFLRRKGWPNHJ-UHFFFAOYSA-N C1(C=2C(C(N1)=O)=CC=CC2)=O.[K].C2(C=1C(C(N2)=O)=CC=CC1)=O Chemical compound C1(C=2C(C(N1)=O)=CC=CC2)=O.[K].C2(C=1C(C(N2)=O)=CC=CC1)=O YXPFLRRKGWPNHJ-UHFFFAOYSA-N 0.000 description 1
- 229910004613 CdTe Inorganic materials 0.000 description 1
- 229910002601 GaN Inorganic materials 0.000 description 1
- 229910005540 GaP Inorganic materials 0.000 description 1
- 229910005542 GaSb Inorganic materials 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 229910017680 MgTe Inorganic materials 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- 235000021360 Myristic acid Nutrition 0.000 description 1
- 238000004497 NIR spectroscopy Methods 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 229910007709 ZnTe Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- YNNGZCVDIREDDK-UHFFFAOYSA-N aminocarbamodithioic acid Chemical compound NNC(S)=S YNNGZCVDIREDDK-UHFFFAOYSA-N 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical class OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
- 239000012230 colorless oil Substances 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
- 238000010586 diagram Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000002149 energy-dispersive X-ray emission spectroscopy Methods 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 229910052949 galena Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- WPYVAWXEWQSOGY-UHFFFAOYSA-N indium antimonide Chemical compound [Sb]#[In] WPYVAWXEWQSOGY-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 230000001443 photoexcitation Effects 0.000 description 1
- 238000000628 photoluminescence spectroscopy Methods 0.000 description 1
- -1 phthalimide compound Chemical class 0.000 description 1
- 125000005543 phthalimide group Chemical group 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- SBIBMFFZSBJNJF-UHFFFAOYSA-N selenium;zinc Chemical compound [Se]=[Zn] SBIBMFFZSBJNJF-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
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- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
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- C08G65/32—Polymers modified by chemical after-treatment
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Abstract
Description
式中、mは、0とおよそ4500の間、 又はより好ましくは、0とおよそ450の間、又は、0とおよそ17の間である。特定の実施形態において、mは、およそ8、およそ13、およそ17又はおよそ45である。これらの化合物は、量子ドットナノ粒子のコア成長及び/又はシェリングのための配位子化合物(すなわち、キャッピング剤)として用いるのに適している。
の化合物を合成する方法を特徴とし、式中、mは、上に定義した通りであり、XはH、―CH3、又は―CH2CO2Hを含むか又は基本的にそれから成り、Yはp―トルエンスルホネート、カルボキシル(例えば―CH2CO2H又は―PhCO2H)、―SiPh2 tBu、フェニル(例えば―CH2Ph)、チオール、アミノ、ジチオカルバマト、ホスホン酸、ホスフィン酸(phosphinc acid)、ビニル、アセチレン、アリール、ヘテロアリールなどを含むか又は基本的にそれから成る。
の化合物を形成する方法であって、ポリ(エチレングリコール)を含む第1の出発物質を提供するステップと、
前記第1の出発物質を、ナノ粒子の表面をキレート化するための官能基を含む第2の出発物質と反応させるステップ
とを含む方法を提供する。
の化合物で少なくとも1つのナノ粒子をキャッピングすることとを含む、キャッピングされたナノ粒子を製造する方法に関する。さらに、更なる態様は、上で定義した式
の化合物によってキャッピングされたナノ粒子を提供する。
第1の半導体材料を含むコアと、
前記第1の半導体材料とは異なる第2の半導体材料を含むシェル
とを具える。
を有するポリ(エチレングリコール)出発物質のヒドロキシル官能価を結合するステップを含み、式中、mは、上で定義した通りであり、Zは、H又は―CH3を含むか又は基本的にそれから成る。Xは脱離基(例えばハロゲン)、p―トルエンスルホネート、メシル(CH3―S(O)2―O―)又は求核試薬(例えばOH)を含むか又は基本的にそれから成り、そしてWはナノ粒子の表面にキレート化するのに適している官能基(例えばカルボキシル又はチオ基)を含むか又は基本的にそれから成る。
との反応の結果製造される前記配位子でキャッピングされたナノ粒子に所望の溶解性を与えてもよく、又は、Zは反応後変更されて所望の頭部基を組み込んでもよく、該頭部基は、例えばp―トルエンスルホネート、カルボキシル(例えば―CH2CO2H又は―PhCO2H)、―SiPh2 tBu、フェニル(例えば―CH2Ph)、チオール、アミノ、ジチオカルバマト、ホスホン酸、ホスフィン酸(phosphinc acid)、ビニル、アセチレン、アリール、ヘテロアリール、などであるがこれに限定されない。
を有し、式中、Xは、―CH3を含むか又は基本的にそれから成り、mはポリ(エチレングリコール)メチルエーテル(〜350)出発物質及び配位子化合物の両方においておよそ8である。Yは、ポリ(エチレングリコール)メチルエーテル(およそ350の分子量を有する)出発物質においてHを含むか又は基本的にそれから成り、そしてYは、配位子化合物において―CH2CO2Hを含むか又は基本的にそれから成る。
図式1:ポリ(オキシエチレングリコール)350モノメチルエーテルp―トルエンスルホナートの合成
DCM(80mL)内のTsCl(27.792g、143.00mmol)の溶液を、ポリ(オキシエチレングリコール)350モノメチルエーテル(50.000g、143.00mmol)の氷で冷却した溶液、トリエチルアミン(40.30mL、290.0mmol)及びDCM(75mL)内のDMAP(0.177g、1.4mmol)に2時間にわたって滴加し、そして結果として生じる混合物を室温に暖めながら終夜撹拌した。反応混合物を、蒸留水(2×200mL)、飽和炭酸水素ナトリウム溶液(2×100mL)、飽和クエン酸溶液(2×100mL)によって洗浄し、無水硫酸ナトリウムで乾燥させ、濾過し、減圧下で濃縮させ、黄色の油状物を生じた。この油状物をヘキサン(3×200mL)において溶解させ、反応していないTsClは濾過によって反応混合物から分離した。濾液を減圧下で濃縮させ、淡黄色の油状物としてポリ(オキシエチレングリコール)350モノメチルエーテルp―トルエンスルホナートが得られた。
図式2:モノメチルエーテルポリ(オキシエチレングリコール)350フタルイミドの合成
カリウムフタルイミド(2.679g、14.48mmol)を、DMF(45mL)/水(6mL)内のポリ(オキシエチレングリコール)350モノメチルエーテルp―トルエンスルホナート(5.000g、9.65mmol)の溶液に加え、それから終夜撹拌した(80℃)。
テトラヒドロフラン(500mL)内のブロモ酢酸(162.83g、1.1719モル)の溶液を、撹拌して冷却した(0℃)テトラヒドロフラン(500mL)内の水素化ナトリウム(93.744g、2.3436モル)の懸濁液に滴加した。あらかじめ乾燥させた(120℃、高真空、1時間)ポリ(オキシエチレングリコール)350モノメチルエーテルを、テトラヒドロフラン(150mL)において溶解させ、反応混合物に滴加した。反応混合物を室温に暖めながら終夜撹拌した。
本発明の実施形態に適合する代表的な量子ドット材料は、CdSe、GaAs、InAs、InP、CuInS2、CuInSe2及びCuIn1―xGaxSe2を含む。ナノ粒子合成は、例えば、米国特許第6,379,635号及び同時係属の米国特許出願第11/579,050号及び11/588,880号に説明される技術を用いて実行してもよい。ナノ粒子は、任意の従来の技術(例えば、XRD、UV/Vis/近赤外分光測定法、SEM、TEM、EDAX、光ルミネセンス分光測定法、元素分析)によって特徴づけられてもよい。
Claims (22)
- ナノ粒子のコアに近接して配置される請求項1に記載の配位子。
- 前記ナノ粒子のコアは少なくとも1つの半導体材料を含む請求項2に記載の配位子。
- ナノ粒子のシェルに近接して配置される請求項1に記載の配位子。
- 前記ナノ粒子のシェルは少なくとも1つの半導体材料を含む請求項4に記載の配位子。
- 溶媒の中に配置され、該溶媒が少なくとも1つのナノ粒子前駆体材料を更に含む請求項1に記載の配位子。
- 前記第1の出発物質は、末端ヒドロキシル基を含み、前記第2の出発物質は脱離基を含み、前記第1及び第2の出発物質を反応させることは、前記脱離基を分離させることを含む請求項7に記載の方法。
- 少なくとも1つのナノ粒子を前記化合物でキャッピングすることを更に含む請求項7又は8に記載の方法。
- XはH、CH3、又は―CH2CO2Hのうち少なくとも1つを含む請求項7乃至10の何れか1項に記載の方法。
- Yはp―トルエンスルホネート、カルボキシル、―CH2CO2H、―PhCO2H、―SiPh2 tBu、フェニル、―CH2Ph、チオール、アミノ、ジチオカルバマト、ホスホン酸、ホスフィン酸(phosphinc acid)、ビニル、アセチレン、アリール、ヘテロアリールなどのうち少なくとも1つを含む請求項7乃至11の何れか1項に記載の方法。
- mはおよそ8からおよそ45である請求項7乃至12の何れか1項に記載の方法。
- 前記少なくとも1つのナノ粒子は、少なくとも1つの半導体材料を含む請求項7乃至13の何れか1項に記載の方法。
- XはH、CH3、又は―CH2CO2Hのうち少なくとも1つを含む請求項15に記載のナノ粒子。
- Yはp―トルエンスルホネート、カルボキシル、―CH2CO2H、―PhCO2H、―SiPh2 tBu、フェニル、―CH2Ph、チオール、アミノ、ジチオカルバマト、ホスホン酸、ホスフィン酸(phosphinc acid)、ビニル、アセチレン、アリール、ヘテロアリールなどのうち少なくとも1つを含む請求項15又は16に記載のナノ粒子。
- mはおよそ8からおよそ45である請求項15、16又は17に記載のナノ粒子。
- ナノ粒子の少なくとも1つは、少なくとも1つの半導体材料を含む請求項15乃至18の何れか1項に記載のナノ粒子。
- 前記複数のナノ粒子を、前記ナノ粒子が可視光を発することができるように励起するための手段を更に含む請求項20に記載の表示装置。
- 前記複数のナノ粒子はそれぞれ、
第1の半導体材料を含むコアと、
前記第1の半導体材料とは異なる第2の半導体材料を含むシェル
とを具える請求項21又は22に記載の表示装置。
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WO2014103584A1 (ja) * | 2012-12-26 | 2014-07-03 | 富士フイルム株式会社 | 半導体膜、半導体膜の製造方法、太陽電池、発光ダイオード、薄膜トランジスタ、および、電子デバイス |
JP2014127563A (ja) * | 2012-12-26 | 2014-07-07 | Fujifilm Corp | 半導体膜、半導体膜の製造方法、太陽電池、発光ダイオード、薄膜トランジスタ、および、電子デバイス |
US10886421B2 (en) | 2012-12-26 | 2021-01-05 | Fujifilm Corporation | Semiconductor film, method of producing semiconductor film, solar cell, light-emitting diode, thin film transistor, and electronic device |
WO2017086362A1 (ja) * | 2015-11-20 | 2017-05-26 | Jsr株式会社 | ナノ粒子集合体及びその製造方法、ナノ粒子集合体組成物、波長変換層、並びにリガンド |
JPWO2017086362A1 (ja) * | 2015-11-20 | 2018-07-12 | Jsr株式会社 | ナノ粒子集合体及びその製造方法、ナノ粒子集合体組成物、波長変換層、並びにリガンド |
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CN103554477B (zh) | 2017-03-01 |
KR101690210B1 (ko) | 2016-12-27 |
IL207721A0 (en) | 2010-12-30 |
AU2009219983A1 (en) | 2009-09-03 |
JP5749495B2 (ja) | 2015-07-15 |
AU2009219983A2 (en) | 2010-10-28 |
US8337720B2 (en) | 2012-12-25 |
CN103554477A (zh) | 2014-02-05 |
CA2716552A1 (en) | 2009-09-03 |
CN101959933B (zh) | 2013-09-18 |
WO2009106810A1 (en) | 2009-09-03 |
EP2250212A1 (en) | 2010-11-17 |
KR20160023925A (ko) | 2016-03-03 |
TW200944552A (en) | 2009-11-01 |
CN101959933A (zh) | 2011-01-26 |
CA2716552C (en) | 2016-02-02 |
KR101735575B1 (ko) | 2017-05-15 |
US20090212258A1 (en) | 2009-08-27 |
IL207721A (en) | 2013-10-31 |
KR20100138925A (ko) | 2010-12-31 |
TWI455958B (zh) | 2014-10-11 |
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