TW201446639A - 表面官能化之奈米顆粒 - Google Patents
表面官能化之奈米顆粒 Download PDFInfo
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- TW201446639A TW201446639A TW103130660A TW103130660A TW201446639A TW 201446639 A TW201446639 A TW 201446639A TW 103130660 A TW103130660 A TW 103130660A TW 103130660 A TW103130660 A TW 103130660A TW 201446639 A TW201446639 A TW 201446639A
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- 150000004714 phosphonium salts Chemical class 0.000 description 1
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- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000004060 quinone imines Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 239000004054 semiconductor nanocrystal Substances 0.000 description 1
- 230000005476 size effect Effects 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910052950 sphalerite Inorganic materials 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 125000004354 sulfur functional group Chemical group 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
- ZGNPLWZYVAFUNZ-UHFFFAOYSA-N tert-butylphosphane Chemical compound CC(C)(C)P ZGNPLWZYVAFUNZ-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
- ZMBHCYHQLYEYDV-UHFFFAOYSA-N trioctylphosphine oxide Chemical compound CCCCCCCCP(=O)(CCCCCCCC)CCCCCCCC ZMBHCYHQLYEYDV-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- GAAKLDANOSASAM-UHFFFAOYSA-N undec-10-enoic acid;zinc Chemical compound [Zn].OC(=O)CCCCCCCCC=C GAAKLDANOSASAM-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- DJWUNCQRNNEAKC-UHFFFAOYSA-L zinc acetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O DJWUNCQRNNEAKC-UHFFFAOYSA-L 0.000 description 1
- 229940118257 zinc undecylenate Drugs 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
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Abstract
本發明係關於製造表面官能化之奈米顆粒、例如製造納入表面結合官能團之半導體量子點奈米顆粒之方法,該等表面結合官能團可增加該等量子點用於各應用中之便利性,例如納入溶劑、墨水、聚合物、玻璃、金屬、電子材料及器件、生物分子及細胞中。該方法包含在奈米顆粒表面結合配體X-Y-Z存在下使第一與第二奈米顆粒前體物質反應,其中X係奈米顆粒表面結合基團,Y係連接基團,且Z係官能團,其中Y包含聚乙二醇基團,且/或Z包含納入末端不飽和基團之脂肪族基團,該反應係在允許該表面結合配體與該等生長奈米顆粒結合之條件下進行以製造該等表面官能化之奈米顆粒。
Description
本發明係關於製造表面官能化之奈米顆粒、具體而言(但非絕對)製造納入表面結合官能團之半導體量子點奈米顆粒之方法,該等表面結合官能團可增加該等量子點用於各應用中之便利性,例如納入溶劑、墨水、聚合物、玻璃、金屬、電子材料及器件、生物分子及細胞中。
半導體奈米顆粒之尺寸決定材料之電子性質;帶隙能量由於量子侷限效應而與半導體奈米顆粒之尺寸成反比。另外,奈米顆粒之較大表面積與體積之比率對奈米顆粒之物理及化學性質具有顯著影響。
與單個半導體奈米顆粒之尺寸有關之兩個基本因素導致其具有獨特性質。第一因素係較大表面與體積之比率;當顆粒變小時,表面原子數與內部原子數之比率會增大。此使得表面性質在材料之整體性質中起重要作用。對於許多包括半導體奈米顆粒之材料而言,第二因素為材料之電子性質會隨尺寸而變,此外,由於量子侷限效應,帶隙會隨著顆粒尺寸的減小而逐漸變大。該效應係「箱中電子」受侷限所致之結果,其可產生與彼等在原子及分子中所觀察者類似之離散能階,而非如在相應半導體塊材中所觀察到的連續能帶。因此,對於半導體奈米顆粒而言,其物理參數使得因吸收電磁輻射而產生之「電子及電洞」與能量大於第一激子躍遷之光子之接近程度大於相應大結晶
材料,此外不能忽略庫侖(Coulombic)相互作用。端視奈米顆粒材料之粒徑及組成,此可導致窄帶寬發射。因此,量子點具有比相應大結晶材料更高的動能且因而第一激子躍遷(帶隙)之能量會隨著顆粒直徑的減小而增加。
由單一半導體材料以及外部有機鈍化層組成之核半導體奈米顆粒往往具有相對低量子效率,此乃因在位於奈米顆粒表面上之缺陷及懸空鍵處發生的電子-電洞複合所致,該等缺陷及懸空鍵可產生非輻射性電子-電洞複合。
一種消除量子點無機表面上之缺陷及懸空鍵的方法係生長第二無機材料以製造「核-殼」顆粒,該第二無機材料具有較寬帶隙且與磊晶生長於核顆粒表面上之核材料之晶格的晶格失配較少。核-殼顆粒可將限定於核內之任一載流子與原本用作非輻射性複合中心的表面狀態隔開。一個實例係生長於CdSe核表面上之ZnS。
另一方法係製備核-多殼結構,其中將「電子-電洞」對完全限定於由幾個特定材料之單層組成的單殼層內,例如量子點-量子井結構。此處,核為寬帶隙材料,外面為較窄帶隙材料之薄殼,並覆蓋有另一寬帶隙層,例如CdS/HgS/CdS,其係以以下方式來生長:使用Hg取代Cd在核奈米晶體表面上沈積僅幾個HgS單層,隨後在該單層上生長CdS單層。所得結構展現被明確限定於HgS層中之光-激發載流子。
為了進一步增強量子點之穩定性並幫助限定電子-電洞對,一種最常用的方法係在核上磊晶生長組成漸變之合金層,此可有助於緩解原本可導致缺陷之應變。此外,為了改良CdSe核之結構穩定性及量子產率,可使用Cd1-xZnxSe1-ySy漸變合金層,而不在核上直接生長ZnS殼。已發現此可顯著增強量子點之光致發光發射。
用原子雜質摻雜量子點亦係操控奈米顆粒之發射及吸收性質的有效方式。已研發出摻雜寬帶隙材料之程序,例如用錳及銅摻雜硒化
鋅及硫化鋅(ZnSe:Mn或ZnS:Cu)。在半導體奈米晶體中摻雜不同的發光激活劑可在甚至低於塊狀材料帶隙之能量下調節光致發光及電致發光,而量子尺寸效應可經由奈米晶體尺寸調節激發能而不會引起與激活劑有關之發射能量的顯著變化。
最終無機表面原子在任一核、核-殼或核-多殼、摻雜或漸變奈米顆粒中之配位作用不完全,其中顆粒表面上高反應性、不完全配位原子之「懸空鍵」可導致顆粒聚結。可藉由用有機保護基團鈍化(亦稱為「封端」)「裸露」表面原子來克服該問題。
最外一層有機材料或護套材料(稱為「封端劑」)有助於抑制顆粒聚結並保護奈米顆粒免受其周圍的電子及化學環境之影響。圖1中提供此一奈米顆粒之示意圖。在許多情況下,封端劑係實施奈米顆粒製備的溶劑,且包含路易士(Lewis)鹼化合物或以惰性溶劑(例如烴)稀釋之路易士鹼化合物。路易士鹼封端劑上之孤對電子能夠與奈米顆粒表面發生供體型配位作用。適宜路易士鹼化合物包括單齒或多齒配體,例如膦(三辛基膦、三酚基膦、第三丁基膦)、氧化膦(三辛基氧化膦)、烷基膦酸、烷基胺(十六胺、辛胺)、芳基胺、吡啶、長鏈脂肪酸及噻吩,但並不限於該等材料。
量子點奈米顆粒之物理/化學不穩定性及其與許多應用之不相容性已限制了其廣泛利用。因此,人們已應用一系列表面改性程序來使量子點更加穩定並提高其與期望應用之相容性。人們的嘗試主要係使封端劑具有雙或多官能性或用具有可用於進一步化學連接之官能團的額外有機層塗敷封端層。
最廣泛使用之量子點表面改性程序稱作「配體交換」。隨後,用引入期望性質或官能團之配體化合物替換在核合成及加殼程序期間與量子點表面意外配位之配體分子。該配體交換策略可固有地顯著降低量子點之量子產率。圖2中示意性繪示該方法。
替代表面改性策略使離散分子或聚合物與業已在加殼程序期間與量子點表面配位之配體分子相互螯合。儘管該等合成後相互螯合策略通常可維持量子產率,但其產生尺寸顯著較大之量子點。圖3中示意性繪示該方法。
儘管現行配體交換及相互螯合程序可增強量子點奈米顆粒與其期望應用之相容性,但其一般會因量子點之無機表面受損及/或最終奈米顆粒尺寸增大而導致較低量子產率。
本發明之目的係避免或緩解一或多個上述問題。
本發明概言之係關於製造表面官能化之奈米顆粒之方法,該方法包含在納入奈米顆粒結合基團及官能團之奈米顆粒表面結合配體存在下使第一與第二奈米顆粒前體物質反應,該反應係在允許該表面結合配體與生長奈米顆粒結合之條件下實施以製造該等表面官能化之奈米顆粒。
參照以上非限定性實例及附圖來闡釋本發明,其中圖1係先前技術中納入相互螯合表面配體之核-殼量子點奈米顆粒之示意圖;圖2係先前技術中配體交換方法的示意圖;圖3係先前技術中配體相互螯合方法的示意圖;圖4係提供表面官能化奈米顆粒之本發明方法的示意圖;圖5係實例7中製備之InP核奈米晶體的IR波譜;圖6係實例7中製備的經十一烯酸封端之InP核奈米晶體的層析圖;圖7係實例7中根據本發明製備之InP/ZnS核-殼奈米晶體的IR波譜;且
圖8係實例7中根據本發明製備之InP/ZnS核/殼奈米晶體的層析圖。
本發明之第一態樣提供製造表面官能化之奈米顆粒之方法,包含在式3之奈米顆粒表面結合配體存在下使第一與第二奈米顆粒前體物質反應。
X-Y-Z 式3其中X係奈米顆粒表面結合基團,Y係連接基團,且Z係官能團,其中Y包含聚乙二醇基團,且/或Z包含納入末端不飽和基團之脂肪族基團,該反應係在允許該表面結合配體與生長奈米顆粒結合之條件下實施以製造該等表面官能化之奈米顆粒。
本發明概言之係關於製造表面官能化之奈米顆粒之方法,該方法包含在納入奈米顆粒結合基團及官能團之奈米顆粒表面結合配體存在下使第一與第二奈米顆粒前體物質反應,該反應係在允許該表面結合配體與生長奈米顆粒結合之條件下實施以製造該等表面官能化之奈米顆粒。
本發明提供將奈米顆粒前體物質轉化為最終奈米顆粒材料,同時亦在最終奈米顆粒外表面上提供官能化層之方法。圖4中示意性繪示本發明之方法。先前必須以至少兩個單獨順序步驟來實施該方法,第一步驟涉及奈米顆粒之製造,且單獨第二步驟涉及配體交換或相互螯合以在奈米顆粒表面上提供官能化配體(參見圖2及3)。然而,吾人已驚奇地發現可在官能化奈米顆粒表面結合配體存在下組合奈米顆粒前體物質,而並不損害奈米顆粒前體一同組合及反應之能力,或表面結合配體與最終奈米顆粒表面結合之能力。
另外令人感到驚奇地是,可將本發明第一態樣之方法應用於自擬納入生長奈米顆粒中之兩個或更多個離子源製造表面官能化核奈米
顆粒(視需要在分子簇化合物存在下製造,如申請者之同在申請中之歐洲專利申請案(公開案第EP1743054A號)及英國專利申請案(申請案第0714865.3號)中所述),以及應用於表面官能化核-殼奈米顆粒之製造,其中可在表面結合配體存在下實施外殼層之沈積。
因此本發明提供在奈米顆粒之核生長及/或加殼期間使所選預先經化學官能化之配體有意與量子點奈米顆粒表面原位配位之策略。該策略使得不需要奈米顆粒合成後表面改性程序且可藉此以更少操控步驟產生在物理/化學上穩定、量子產率高、直徑小且與其既定應用相容之量子點奈米顆粒,該應用可包括(但不限於)將該等奈米顆粒納入溶劑、器件、墨水、聚合物、玻璃中、或使該等量子點奈米顆粒經由形成直接鍵結之化學反應附接至細胞、生物分子、金屬、分子或聚合物上。
本發明可促進在封端劑中合成奈米顆粒,該封端劑具有可鈍化奈米顆粒表面之奈米顆粒結合基團及具有進一步化學連接能力(例如圍繞奈米顆粒之交聯或納入聚合物材料內)的額外配體。
第一及第二前體物質及表面結合配體可以任何期望順序組合在一起,前提是在配體存在下第一及第二前體可發生反應。較佳地,使該奈米顆粒表面結合配體接觸該第一奈米顆粒前體物質以達成該表面結合配體與該第一前體物質之結合,之後使該第一前體物質與該第二奈米顆粒前體物質反應。
在形成本發明第一態樣之方法的第一較佳實施例中,第一奈米顆粒前體物質含有擬納入生長奈米顆粒中之第一離子且第二奈米顆粒前體物質含有擬納入生長奈米顆粒中之第二離子。
本發明之第二態樣提供製造表面官能化核半導體奈米顆粒之方法,該方法包含使含有擬納入生長奈米顆粒中之第一離子的第一核奈
米顆粒前體物質與含有擬納入生長奈米顆粒中之第二離子的第二核奈米顆粒前體物質反應,該反應係在納入奈米顆粒結合基團及官能團之奈米顆粒表面結合配體存在下在允許該表面結合配體與生長奈米顆粒結合之條件下實施以製造該等表面官能化之奈米顆粒。
用於本發明第二態樣中之奈米顆粒表面結合配體可與用於本發明第一態樣中之配體一致。舉例而言,在本發明第二態樣之較佳實施例中,奈米顆粒表面結合配體係關於本發明第一態樣之上文所述之式3配體。
第一及第二離子可係選自週期表之任一期望族,例如(但不限於)週期表之第11、12、13、14、15或16族。第一及/或第二離子可係過渡金屬離子或d區金屬離子。較佳地,第一離子係選自週期表之第11、12、13或14族且第二離子係選自週期表之第14、15或16族。
尤佳地,第一及第二(核)奈米顆粒前體物質係在分子簇化合物存在發生反應,如以下實例1中所例示。該方法可應用申請者之同在申請中之歐洲專利申請案(公開案第EP1743054A號)中所述之方法。分子簇化合物可含有第三及第四離子。該第三及第四離子中至少一者較佳與分別包含於第一及第二(核)奈米顆粒前體物質中之該第一及第二離子不同。第三及第四離子可係選自週期表之任一期望族,例如(但不限於)週期表之第11、12、13、14、15或16族。第三及/或第四離子可係過渡金屬離子或d區金屬離子。較佳地,第三離子係選自週期表之第11、12、13或14族且第四離子係選自週期表之第14、15或16族。舉例而言,分子簇化合物可納入分別來自週期表之第12及16族之第三及第四離子且得自第一及第二(核)奈米顆粒前體物質之第一及第二離子可分別得自週期表之第13及15族。因此,本發明第一及第二態樣之方法可應用得自申請者未公開之同在申請中的英國專利申請案(申請案第0714865.3號)之方法。
第一及第二(核)奈米顆粒前體物質、分子簇化合物及表面結合配體可以任一期望順序組合在一起。第一及第二(核)前體物質中之一者可在與第一及第二(核)前體物質中之另一者反應之前或在此期間與分子簇化合物接觸。尤佳地,首先使表面結合配體接觸第一(核)奈米顆粒前體物質以形成第一混合物,隨後使其接觸分子簇化合物以形成第二混合物,且然後使第二(核)奈米顆粒前體物質接觸該第二混合物。
應瞭解在第一與第二(核)奈米顆粒前體物質反應期間,可以一或多份添加第一(核)奈米顆粒前體物質且可以一或多份添加第二(核)奈米顆粒前體物質。較佳以兩份或更多份添加第一(核)奈米顆粒前體物質。在此種情況下,較佳在添加每份第一(核)前體物質之間提高含有第一及第二(核)奈米顆粒前體物質及奈米顆粒表面結合配體之反應混合物之溫度。另外或或者,可以兩份或更多份添加第二(核)奈米顆粒前體物質,因此可在添加每份第二(核)前體物質之間提高含有第一及第二(核)奈米顆粒前體物質及奈米顆粒表面結合配體之反應混合物之溫度。
在本發明第一態樣之第二較佳實施例中,第一奈米顆粒前體物質係核奈米顆粒且第二奈米顆粒前體物質含有第一離子以形成擬沈積於該核奈米顆粒表面上之殼之一部分。
在本發明第一態樣之第三較佳實施例中,第二奈米顆粒前體物質係核奈米顆粒且第一奈米顆粒前體物質含有第一離子以形成擬沈積於該核奈米顆粒表面上之殼之一部分。
第二及第三較佳實施例闡述了以下實例2及3中所例示之方法,藉此可應用本發明第一態樣中所述之一般方法在核奈米顆粒外部上形成材料外殼、或層,其中該外殼具有化學官能化外表面。
與本發明第一態樣之第二及第三較佳實施例有關之本發明第三
態樣提供製造表面官能化核-殼半導體奈米顆粒之方法,該方法包含使核半導體奈米顆粒與第一奈米顆粒前體物質反應,該第一奈米顆粒前體物質含有第一離子以形成擬沈積於該核半導體奈米顆粒表面上之殼之一部分,該反應係在納入奈米顆粒結合基團及官能團之奈米顆粒表面結合配體存在下實施,該反應係在允許該表面結合配體與生長核-殼半導體奈米顆粒表面結合之條件下實施以製造該等表面官能化核-殼半導體奈米顆粒。
用於本發明第三態樣中之奈米顆粒表面結合配體可與用於本發明第一態樣中之配體一致。舉例而言,在本發明第三態樣之較佳實施例中,奈米顆粒表面結合配體係上述關於本發明第一態樣之式3配體。
對於本發明之第三態樣,表面結合配體可接觸核奈米顆粒及第一前體物質中之一者,然後接觸另一者,或可同時接觸二者。因此,根據以下實例2中所述之方法,可使結合配體接觸核奈米顆粒以達成該配體與該核奈米顆粒之結合,然後使該核奈米顆粒與該第一前體物質反應。或者,根據以下實例3,可使配體接觸第一前體物質以達成表面結合配體與第一奈米顆粒前體物質之結合,然後使該第一前體物質與該核奈米顆粒反應。較佳地,本發明第三態樣之方法另外包含使該核奈米顆粒及該第一前體物質與第二奈米顆粒前體物質反應,該第二奈米顆粒前體物質含有第二離子以形成擬沈積於該核半導體奈米顆粒表面上之殼之一部分。
在本發明第一態樣及本發明第三態樣之第二及第三實施例中,核奈米顆粒較佳含有第一及第二核離子,其可係選自週期表之任一期望族,例如(但不限於)週期表之第11、12、13、14、15或16族。核奈米顆粒可含有過渡金屬離子及/或d區金屬離子。較佳地,核奈米顆粒含有選自週期表中第11、12、13或14族之離子及選自第14、15或16族
之離子。
包含於奈米顆粒前體物質中擬形成奈米顆粒殼之一部分的第一離子可係選自週期表之任一期望族,包括(但不限於)週期表之第11、12、13、14、15及/或16族。此外,第一離子可係過渡金屬離子或d區金屬離子。
若適宜,可以一或多份添加奈米顆粒前體物質及/或核奈米顆粒。較佳地,在反應期間前體物質及核奈米顆粒之至少一者係以兩份或更多份添加。可在添加每份前體物質及核奈米顆粒之間提高含有前體物質、核奈米顆粒及/或奈米顆粒表面結合配體之反應混合物之溫度。
尤佳地,本發明第一態樣及本發明第三態樣之第二及第三較佳實施例之方法另外包含使該核奈米顆粒及該前體物質與第三奈米顆粒前體物質反應,該第三奈米顆粒前體物質含有第二離子以形成擬沈積於該核半導體奈米顆粒表面上之殼之一部分。該第二離子亦可係選自週期表之任一期望族,包括(但不限於)週期表之第11、12、13、14、15及/或16族。此外,第二離子可係過渡金屬離子或d區金屬離子。
尤佳地,包含於奈米顆粒前體物質中之第一及/或第二離子與該第一及第二核離子不同。舉例而言,核-殼奈米顆粒可包含主要由III-V半導體材料(例如InP)製成之核及主要由II-VI半導體材料(例如ZnS)製成之殼。在此種情況下,第一及第二核離子可為銦離子及磷離子,且得自奈米顆粒前體物質之第一及第二離子可為鋅離子及硫離子。適宜奈米顆粒前體物質可係Zn(Ac)或類似物及(TMS)3P。
當向包括表面結合配體之反應混合物中添加第三奈米顆粒前體物質時,可以一或多份添加該第三奈米顆粒前體物質。較佳以兩份或更多份添加該奈米顆粒前體物質。在此種情況下,較佳在添加每份第三前體物質之間提高含有(核)奈米顆粒前體物質及奈米顆粒表面結合
配體之反應混合物之溫度。
可在任一適宜溶劑中實施奈米顆粒前體(及核奈米顆粒(若適宜))間之反應。較佳在不同於該奈米顆粒表面結合配體之溶劑中實施反應,但應瞭解並非必須如此,且在替代實施例中,表面結合配體可代表用於實施反應之一種溶劑或多種溶劑之一。溶劑可係配位溶劑(即與生長奈米顆粒配位之溶劑)或非配位溶劑(即不與生長奈米顆粒配位之溶劑)。較佳地,溶劑係路易士鹼化合物,其可係選自由HAD、TOP、TOPO、DBS、辛醇及諸如此類組成之群。
表面結合配體之奈米顆粒結合基團較佳與表面結合配體之官能團不同。官能團可納入或不納入可在奈米顆粒生長期間及/或之後選擇性移除之所選保護基團。
可選擇表面結合配體之官能團的性質以使最終表面官能化之奈米顆粒具有任一期望化學或物理性質。舉例而言,可選擇含有使表面官能化之奈米顆粒對特定試劑具有預定反應性之官能團的配體。或者,可選擇納入官能團之配體,該官能團使表面官能化之奈米顆粒具有水性相容性(即穩定分散或溶解於水性介質中之能力)。此外,官能團可提供使相同奈米顆粒表面周圍之表面結合配體、與毗鄰奈米顆粒結合之配體及/或納入相容性可交聯基團之其他周圍材料(例如聚合物)交聯之能力。此一官能團可含有單個乙烯基、或更佳兩個、三個或更多個乙烯基以促進該等與奈米顆粒結合之乙烯基間之交聯及/或與奈米顆粒結合之乙烯基與包含於周圍材料中之乙烯基間之交聯。
表面結合配體之官能團可含有一或多個選自由硫、氮、氧及磷組成之群的原子。官能團可係選自由氫氧化物、烷醇基、羧酸、羧酸酯、胺、硝基、聚乙二醇、磺酸、磺酸酯、磷酸及磷酸酯組成之群。
此外,官能團可係帶電荷或極性基團,例如(但不限於)氫氧化物鹽、烷醇鹽、羧酸鹽、銨鹽、磺酸鹽或磷酸鹽。
表面結合配體可含有擬結合至生長奈米顆粒(即根據第一較佳實施例生長之核奈米顆粒或根據第二/第三較佳實施例在核奈米顆粒上生長之殼)之任一適宜奈米顆粒結合基團。較佳地,奈米顆粒結合基團含有選自由硫、氮、氧及磷組成之群的原子。奈米顆粒結合基團可含有選自由硫基、胺基、側氧基及二氧磷基組成之群的物質。奈米顆粒結合基團可係選自由氫氧化物、烷醇基、羧酸、羧酸酯、胺、硝基、聚乙二醇、磺酸、磺酸酯、磷酸及磷酸酯組成之群。此外,奈米顆粒結合基團可係帶電荷或極性基團,例如(但不限於)氫氧化物鹽、烷醇鹽、羧酸鹽、銨鹽、磺酸鹽或磷酸鹽。
表面結合配體之結合基團及官能團較佳經由連接體連接,該連接體可呈任一期望形式。尤佳地,該連接體係選自由下述組成之群:共價鍵;碳、氮、氧或硫原子;經取代或未經取代、飽和或不飽和脂肪族或脂環族基團;及經取代或未經取代芳香族基團。
奈米顆粒表面結合配體可係視需要包含烷醇基及羧酸基之聚合物化合物,例如聚醚。較佳地,配體係具有末端烷醇基及鍵結至另一末端之羧酸基之聚醚。尤佳配體包括聚乙二醇及其衍生物,其中聚乙二醇中至少一個、更佳二個末端羥基已經衍生化以提供替代官能團,例如烷醇基及/或羧酸基。
本發明提供製造在物理/化學上穩定、量子產率高、直徑小且與其既定應用相容之表面官能化之奈米顆粒的方法。根據本發明製造之奈米顆粒可藉由下式1來表示。
QD-X-Y-Z式1其中:QD代表核或核-(多)殼奈米顆粒;且X-Y-Z代表奈米顆粒表面結
合配體,其中X係奈米顆粒表面結合基團;Y係連接X與Z之連接基團;且Z係官能團。
X及/或Z可係經取代或未經取代烷基、經取代或未經取代芳基、經取代或未經取代雜環、經取代或未經取代聚乙二醇(取代基之實例包括(但不限於)鹵素、醚、胺、醯胺、酯、腈、異腈、醛、碳酸酯、酮、醇、羧酸、疊氮化物、亞胺、烯胺、酸酐、醯氯、炔、硫醇、硫化物、碸、亞碸、膦、氧化膦)、或可交聯/可聚合基團(各實例包括羧酸、胺、乙烯基、烷氧基矽烷、環氧化物)。
X及/或Z可係帶電荷或極性基團,例如氫氧化物鹽、烷醇鹽、羧酸鹽、銨鹽、磺酸鹽或磷酸鹽。
X及/或Z可係選自由下述組成之群:-SR1(R1=H、烷基、芳基);-OR2(R2-H、烷基、芳基);-NR3R4(R3及/或R4=H、烷基、芳基);-CO2R5(R5=H、烷基、芳基);-P(=O)OR6OR7(R6及/或R7=H、烷基、芳基);-OR8,其中R8係氫或可經取代或未經取代、及/或飽和或不飽和之烷基;-C(O)OR9,其中R9係氫,經取代或未經取代、飽和或不飽和脂肪族或脂環族基團,或經取代或未經取代芳香族基團;-NR10R11,其中R10及R11獨立地為氫,經取代或未經取代、飽和或不飽和脂肪族或脂環族基團,或經取代或未經取代芳香族基團,或者R10及R11可經連接以使-NR10R11形成任何期望尺寸之含氮雜環,例如五、六或七員環;-N+R12R13R14,其中R12、R13及R14獨立地為氫,經取代或未經取代、飽和或不飽和脂肪族或脂環族基團,或經取代或未經取代芳香族基團;-NO2;,其中R15係氫,經取代或未經取代、飽和或不飽和脂肪族或脂環族基團,經取代或未經取代芳香族基團;-S(O)2OR16,其中R16係氫,經取代或未經取代、飽和或不飽和脂肪族或脂環族基團,或經取代或未經取代芳香族基團;及-P(OR17)(OR18)O,其中R17及R18獨立地為氫,經取代或未經取代、飽
和或不飽和脂肪族或脂環族基團,或經取代或未經取代芳香族基團。
Z可納入任一適宜保護基團。舉例而言,Z可含有酸不穩定保護基團,例如第三丁基、苄基、三苯甲基、甲矽烷基、苯甲醯基、茀基、縮醛、酯、或醚(例如甲氧基甲基醚、2-甲氧基(乙氧基)甲基醚)。或者,Z可含有親核基不穩定保護基團(包括羧酸酯、鋶鹽、醯胺、醯亞胺、胺基甲酸酯、N-磺醯胺、三氯乙氧基甲基醚、三氯乙基酯、三氯乙氧基羰基、烯丙基-醚/胺/縮醛/碳酸酯/酯/胺基甲酸酯)以保護羧酸、醇、硫醇等。此外,Z可納入苄基胺保護基團,其可經脫保護以提供胺基,或者當最後期望對Z實施脫保護以為進一步反應提供二醇時,Z可含有環碳酸酯。
Y可係單鍵、烷基、芳基、雜環、聚乙二醇、經取代或未經取代烷基、經取代或未經取代芳基、經取代或未經取代雜環、經取代或未經取代聚乙二醇(取代基之實例包括鹵素、醚、胺、醯胺、酯、腈、異腈、醛、碳酸酯、酮、醇、羧酸、疊氮化物、亞胺、烯胺、酸酐、醯氯、炔、硫醇、硫化物、碸、亞碸、膦、氧化膦)、可交聯/可聚合基團(各實例包括羧酸、胺、乙烯基、烷氧基矽烷、環氧化物)、或下式2所代表之基團
其中:k、m及n各自獨立地為0至約10,000之任一數字。
在本發明之其他較佳實施例中,X可係酸基或酯基,例如羧酸基或其衍生物或鹽,例如羧酸酯或羧酸鹽。在替代實施例中,X可係磺酸基、磺酸酯或鹽;磷酸基、磷酸酯或鹽;胺基。Z較佳包含一或多個烷基,各烷基含有至少一個不飽和基團。各碳-碳雙或三鍵可係末端不飽和基團(即在碳鏈末端包括原子)或提供在碳鏈內。若Z包含一
或多個烷基,則各烷基鏈可帶有任何期望取代基。連接X與Z之連接基團Y可呈任一便利之形式。舉例而言,Y可含有一或多個脂肪族基團及/或芳香族基團。脂肪族基團可含有直鏈碳鏈、具支鏈碳鏈,或可係脂環族基團。Y可另外包含一或多個醚基。在尤佳實施例中,Y包含視需要經由醚連接與至少一個、較佳兩個或三個不飽和烷基結合之苯基。尤佳奈米顆粒表面結合配體(配體1)具有如下所展示之結構,其可經由三個乙烯基與其他配體及/或周圍物質(例如相容聚合物或可聚合單體)交聯。
可用於本發明方法中之其他較佳式1可交聯配體展示於下文且納入官能團Z(其含有一或多個鍵結至脂肪族或芳香族連接體之乙烯基)、Y(其鍵結至奈米顆粒結合配體)、X(呈任一期望結構),例如彼等上述者。較佳配體納入一個乙烯基、更佳兩個乙烯基、及最佳三個或更多個乙烯基。若Z含有兩個或更多個乙烯基,則乙烯基可經由各烷基鍵結至相同碳原子、或不同碳原子(例如相同碳環或雜環之不同碳原子,該環本身可係飽和、部分飽和或芳香族環)。奈米顆粒結合基團X可係單齒或多齒,如上文所述。舉例而言,X可納入一個羧酸基,如配體1中所示,或者X可納入兩個、三個、或更多個羧酸基。若存在兩個或更多個羧酸基,則各基團可經由烷基鍵結至相同或不同碳原子。
例示性單齒脂肪族配體包括下述者,其中X係羧酸基,Z包含一個、兩個或三個乙烯基,Y係直鏈或具支鏈脂肪族基團,且各x係任
一整數(即0、1、2、3等)。
例示性單齒芳香族配體包括下述者,其中X係羧酸基,Z包含一個、兩個或三個乙烯基,Y含有芳香族基團,且各x係任一整數(即0、1、2、3等)。
例示性雙齒脂肪族配體包括下述者,其中X含有兩個羧酸基,Z包含一個、兩個或三個乙烯基,Y係直鏈或具支鏈脂肪族基團,且各x係任一整數(即0、1、2、3等)。
例示性三齒脂肪族配體包括下述者,其中X含有三個羧酸基,Z包含一個、兩個或三個乙烯基,Y係直鏈或具支鏈脂肪族基團,且各
x係任一整數(即0、1、2、3等)。
應瞭解任一上述例示性結構中之一或多個羧酸基可置換為替代性奈米顆粒結合基團,例如(但不限於)羧酸鹽或酯、磺酸、磺酸酯或磺酸鹽、磷酸、磷酸酯或磷酸鹽、或胺基。此外,連接基團Y可含有除上文所展示之不飽和脂肪族或芳香族基團以外的基團。舉例而言,Y可納入一或多個醚基、碳-碳雙鍵、及/或多環芳香族或非芳香族基團。
在一個較佳實施例中提供本發明第一態樣之方法,其中末端不飽和基團係乙烯基。亦即,奈米顆粒表面結合配體在離奈米顆粒表面最遠的配體末端納入碳-碳雙鍵。
在式3中,X較佳包含至少一個羧酸基或至少一個硫醇基。較佳地,Y包含直鏈或具支鏈脂肪族基團、或芳香族基團。
關於本發明之第一態樣,奈米顆粒表面結合配體可係聚(氧乙二醇)n單甲基醚乙酸,其中n=約1至約5000。較佳地,n係約50至3000、更佳約250至2000、及最佳約350至1000。或者,奈米顆粒表面結合配體可係選自由10-十一烯酸及11-巰基-十一烯組成之群。作為又一較佳替代,奈米顆粒表面結合配體係如上文所展示之配體1。
用於以下實例中之式1之例示性表面結合配體包括聚(氧乙二醇)350單甲基醚乙酸、聚(氧乙二醇)750單甲基醚乙酸、聚(氧乙二醇)2000單甲基醚乙酸、10-十一烯酸、如上文所展示之配體1、及11-巰基-十一烯。
本發明之第四態樣提供使用本發明第一、第二或第三態樣之方法製造的表面官能化之奈米顆粒,該表面官能化之奈米顆粒包含與奈米顆粒表面結合配體結合之奈米顆粒,該配體納入奈米顆粒結合基團及官能團。
根據本發明之任一上述態樣製造的奈米顆粒較佳為半導體奈米顆粒,例如核奈米顆粒、核-殼奈米顆粒、漸變奈米顆粒或核-多殼奈米顆粒。該等奈米顆粒較佳包含一或多個選自以下之離子:週期表之任一適宜族(例如(但不限於)週期表之第11、12、13、14、15或16族)、過渡金屬離子及/或d區金屬離子。奈米顆粒核及/或殼(若適用)可納入一或多種選自由下述組成之群的半導體材料:CdS、CdSe、CdTe、ZnS、ZnSe、ZnTe、InP、InAs、InSb、AlP、AlS、AlAs、AlSb、GaN、GaP、GaAs、GaSb、PbS、PbSe、Si、Ge、MgS、MgSe、MgTe及其組合。
本發明係關於在與製造第一有機層相同的反應中直接或在對有機層進行進一步化學處理(若已使用保護基團)後生長量子點奈米顆粒之具有額外官能度之最終無機層,藉此使其能夠以化學方式與其他化學實體連接。
本發明闡述在奈米顆粒之核生長及/或加殼期間使所選預先經化學官能化之配體有意與量子點奈米顆粒表面原位配位之策略。該策略使得不需要合成後表面改性程序且可以更少操控步驟產生在物理/化學上穩定、量子產率高、直徑小且與其既定應用相容之量子點奈米顆粒,該應用可包括(但不限於)將該等奈米顆粒納入溶劑、器件、墨水、聚合物、玻璃中、或使該等量子點奈米顆粒經由形成直接鍵結之化學反應附接至細胞、生物分子、金屬、分子或聚合物上。
以下實例闡述製造核半導體奈米顆粒及使用本發明方法將半導體材料殼沈積於該等核上之方法。
實例1及4闡述根據闡述於申請者之同在申請中的歐洲專利申請案第EP1743054A號中之發明使用分子簇化合物作為奈米顆粒生長之種來製造InP核奈米顆粒量子點。根據闡述於申請者之同在申請中的英國專利申請案第0714865.3號中之發明,用於實例1及4中之簇包含週期表之第12及16族之離子(分別為Zn及S離子)。
實例2及3闡述使用本發明一個態樣之方法將ZnS殼沈積於實例1中製造之InP核奈米顆粒上之方法。實例5及6闡述使用本發明一個態樣之方法將ZnS殼及ZnS/ZnO殼分別沈積於實例4中製造之InP核奈米顆粒上之方法。實例7闡述製備InP/ZnS核/殼奈米顆粒之方法,其中將ZnS殼沈積於InP核奈米顆粒上之步驟應用本發明一個態樣之方法。
向圓底3-頸燒瓶(250ml)中添加癸二酸二丁酯(100ml)並將其於高度真空及90℃之溫度下置放1小時30分鐘。在單獨的圓底3-頸燒瓶(100ml)中將癸二酸二丁酯(45ml)及乙酸銦(5.036g,17.25mmol)置於高度真空及110℃之溫度下。
在反應燒瓶中於高度真空(約90℃)下將聚(氧乙二醇)750單甲基醚乙酸(51.76mmol)加熱1小時。1小時後,將反應燒瓶冷卻,之後於氮氣下將癸二酸二丁酯與乙酸銦之混合物轉移至反應燒瓶中。隨後將反應燒瓶在高度真空及110℃下放置16小時時間以確保移除所存在之任何過量水。16小時後,形成澄清淺黃色溶液。
將癸二酸二丁酯(100ml)置於3-頸圓底燒瓶(250ml)中並在80℃之溫度下脫氣1小時30分鐘。然後將溫度升至90℃並添加(Et3NH)4[Zn10S4(SPh)16]簇(0.47g)並且攪拌30分鐘。在30分鐘後將溫
度升至100℃並實施以下步驟。在100℃下逐滴添加聚(氧乙二醇)750單甲基醚乙酸銦(0.25M,6ml)。在添加6ml後,將反應混合物攪拌5分鐘,之後逐滴添加(TMS)3P(0.25M,6ml)。將反應溫度升至150℃並再次逐滴添加In(PEG-OMe-750)(0.25M,8ml),攪拌5分鐘,之後再次逐滴添加(TMS)3P(0.25M,8ml)。將反應混合物升至180℃。逐滴添加聚(氧乙二醇)750單甲基醚乙酸銦(0.25M,10ml),且在5分鐘後,添加(TMS)3P(0.25M,7ml)。將反應溫度升至200℃且隨後在200℃下退火45分鐘,之後將溫度降至160℃並在劇烈攪拌下經3天使反應混合物退火。
在3天時間後,將溫度降至室溫並經由添加乙腈直至發生顆粒絮凝來分離反應混合物。一旦形成沉澱物,則經由附接有過濾器之插管移除溶劑。將殘餘固體再溶解於無水氯仿(約94ml)中並於氮氣下注入Schlenk管中。
將癸二酸二正丁酯(11ml)及聚(氧乙二醇)350單甲基醚乙酸(3.53g,7.618mmol)添加至3-頸燒瓶中並在50℃下脫氣15分鐘,然後冷卻至室溫。隨後添加根據實例1製備之磷化銦量子點(3.3ml,約100mg)並再脫氣15分鐘。以固體形式添加無水乙酸鋅(0.71g,3.87mmol)並用氮氣沖洗燒瓶若干次。然後經5小時將溶液加熱至180℃以形成富鋅量子點表面。在180℃下逐滴添加(TMS)2S(1M,1ml,1mmol)並將溶液放置30分鐘以完成ZnS層。使用二乙醚及己烷(50:50)分離並清洗納入InP核及ZnS殼之奈米顆粒量子點。
將根據實例1製備之磷化銦量子點(3.3ml,約100mg)轉移至圓底燒瓶中並經旋轉蒸發來移除氯仿。移除氯仿後在真空下乾燥各量子點。在3-頸圓底燒瓶中,將癸二酸二丁酯(10ml)、聚(氧乙二醇)2000單甲基醚乙酸配體(17.07g,7.74mmol)及乙酸鋅(0.71g,3.87mmol)置於真空及110℃之溫度下。將各量子點及癸二酸二丁酯(5ml)置於Schlenk管中並脫氣15分鐘。在聚(氧乙二醇)2000單甲基醚乙酸配體及乙酸鋅已溶解形成澄清溶液後,將溫度自110℃降至30℃。向聚(氧乙二醇)2000單甲基醚乙酸與乙酸鋅之反應混合物中添加存於癸二酸二丁酯中之量子點並將溫度升至180℃。逐滴添加辛基硫醇(0.175mo,1mmol),隨後將溶液加熱至220℃並保持90分鐘以促進硫醇分解為硫化物離子並完成ZnS殼。使用二乙醚及己烷(50:50)分離並清洗納入InP核及ZnS殼之奈米顆粒量子點。
向圓底3-頸燒瓶(250ml)中添加癸二酸二丁酯(100mL)及10-十一烯酸(4.146g)並將其於高度真空及100℃溫度下置放1小時40分鐘。將溫度降至80℃。添加(Et3NH)4[Zn10S4(SPh)16]簇(0.47g)並將溶液於高度真空下置放30分鐘。此後,將溫度升至100℃並進行以下添加:在100℃下逐滴添加三乙基銦(0.5M,存於3mL癸二酸二丁酯中)。在3mL添加後,將反應混合物攪拌5分鐘,之後逐滴添加(TMS)3P(0.5M,存於3mL癸二酸二丁酯中)。將反應溫度升至160℃並再次逐滴添加三乙基銦(0.5M,0mL),攪拌5分鐘,之後再次逐滴添加(TMS)3P(0.5M,4mL)。將反應混合物升至200℃並經1小時退火,此後將溫度降至150℃並在劇烈攪拌下經3天使反應混合物退火。
在3天時間後,將溫度降至室溫並經由添加乙腈(150mL)來分離反應混合物。一旦形成沉澱物,則藉由離心移除溶劑。將殘餘固體再
溶解於無水氯仿中並轉移至錐形燒瓶中。添加10-十一烯酸(2g)。
作業後處理
HF-InP量子點之酸蝕刻
藉由合併8mL氫氟酸水溶液(58-62wt%溶液)與THF(32mL)來製備氫氟酸溶液。
向分散於氯仿中之InP顆粒中逐份添加HF溶液。使來自500W鹵素燈泡之光線透過560nm濾光片連續輻照反應混合物。此後藉由蒸發移除溶劑。使殘餘物分散於氯仿中,用乙腈實施再沉澱並藉由離心分離。使固體分散至癸二酸二丁酯中。
將癸二酸二丁酯(15mL)及10-十一烯酸(2.6g)裝入裝配有帶側臂冷凝器、溫度計、suba密封塞及攪拌捧的直火乾燥3-頸燒瓶(250mL)中並在80℃下脫氣1小時30分鐘。用氮氣回填燒瓶並添加根據實例4製造之磷化銦核顆粒(1.3g,存於15mL癸二酸二丁酯中),在80℃下對混合物脫氣40分鐘並隨後用氮氣回填。
添加乙酸鋅(1.4g),在80℃下對混合物脫氣30分鐘並用氮氣回填3次。將反應溫度升至120℃,隨後逐滴添加1-辛基硫醇(0.41mL)。隨後將溫度升至220℃並保持90分鐘。將溫度降至190℃,再添加1份1-辛基硫醇(1.09mL)且將溫度升至220℃並保持90分鐘。此可完成ZnS殼。使反應溶液冷卻至190℃。藉由快速添加1-辛醇(1.0mL)來分解殘餘鋅鹽以形成ZnO層並將該溫度保持30分鐘。再添加1份1-辛醇(1.74mL)以完成ZnO層並在相同溫度下保持30分鐘。然後使反應物冷卻至室溫。
在N2下用無水乙腈分離InP/ZnS/ZnO核-多殼奈米顆粒並藉由離心收集。使顆粒分散於甲苯中並用無水乙腈實施再沉澱,之後實施離
心。使顆粒再分散於甲苯中,之後實施離心。將上清液移出至Schlenk管中。
隨後可在標準條件下用Hoveyda-Grubbs觸媒處理所得塗敷有10-十一烯酸封端劑的核-多殼奈米顆粒以使配體經歷非環二烯聚合及/或閉環複分解並使相鄰10-十一烯酸基團交聯,如以下例示性反應圖中所展示。
根據以下展示之反應圖來製造配體1。
將磷化銦核奈米顆粒(0.155g,存於4.4mL癸二酸二丁酯中)裝入裝配有帶側臂冷凝器、溫度計、suba密封塞及攪拌捧之直火乾燥3-頸燒瓶(100mL)中並在100℃下脫氣1小時。使燒瓶冷卻至室溫且隨後用氮氣回填。隨後添加乙酸鋅(0.7483g)及配體1(0.5243g),混合物在55℃下脫氣1小時並用氮氣回填。將反應溫度升至190℃,逐滴添加第三壬基硫醇(0.29mL),使溫度升至190℃並保持1小時30分鐘。使溫度降至180℃,添加1-辛醇(0.39mL)並將溫度保持30分鐘。使反應混合
物冷卻至室溫。
在N2下於乙酸乙酯中藉由離心來分離InP/ZnS核-殼奈米顆粒。用乙腈對顆粒實施沉澱,之後實施離心。使顆粒分散於氯仿中並用乙腈實施再沉澱,之後實施離心。將使用氯仿及乙腈之分散-沉澱程序總共重複實施4次。最後使InP/ZnS核-殼顆粒分散於氯仿中。
隨後可在標準條件下用Hoveyda-Grubbs觸媒處理所得塗敷有配體1封端劑的核-多殼奈米顆粒以使相鄰末端乙烯基團交聯,如以下例示性反應圖中所展示。
或者,可使配體1之末端乙烯基與奈米顆粒配位前發生交聯,如下所示。
在加熱罩上含有攪拌棒且裝配有熱電偶(及溫度控制器)的3-頸圓底燒瓶中將肉豆蔻酸(5.125g)、癸二酸二丁酯(100mL)及十一烯酸鋅
(4.32g)混合在一起並在真空及80℃下脫氣1h。用氮氣回填反應容器並經由側埠添加固體簇[Et3NH]4[Zn10S4(SPh)16](0.47g)。在真空及80℃下將反應物經30min脫氣且在此期間用氮氣對燒瓶回填3次。將反應物加熱至100℃且用玻璃注射器先後逐滴注入3mL In(MA)3溶液(1M,存於癸二酸二丁酯中)、3mL P(TMS)3溶液(1M,存於癸二酸二丁酯中)。在160℃、190℃、220℃及250℃下再次添加In(MA)3及P(TMS)3溶液直至顆粒之最大發射達到680nm。在160℃下使反應物冷卻並在該溫度下維持72h。使反應物冷卻至30℃並添加乙腈以使奈米晶體絮凝為紅色粉末。使粉末再分散於氯仿(650mL)中並添加十一烯酸(10g)。將所得溶液裝入裝配有攪拌棒之200mL透明容器中並在連續的攪拌及來自450W氙燈之光的照射下藉由緩慢添加HF水溶液(5%)在空氣中進行蝕刻。在約15小時內完成蝕刻過程,此後藉由添加甲醇來分離InP核並使其再分散於氯仿中(參見圖5及6)。圖5係InP核奈米晶體之IR波譜,其中可觀察到寬O-H伸縮(3500-2500cm-1);C-H伸縮(2931-2885cm-1);羧基C=O伸縮(1641cm-1);及羧基C-O伸縮(1082cm-1)。
PLmax=611nm,UVmax=522nm,FWHM=65nm,PLQY=22%,藉由TGA分析無機含量=74%。
在加熱罩上含有攪拌棒且裝配有熱電偶(及溫度控制器)的3-頸圓底燒瓶中將存於氯仿中之InP核(100mg)及首諾導熱油(therminol)(10mL)混合在一起並在真空及50℃下脫氣30min。在強氮氣流下經由側埠添加乙酸鋅(380mg)並在30min內將所得混合物加熱至230℃,且在該溫度下保持2hr。此後,將乙烯基硫醇化合物11-巰基-十一烯(0.5mL,用作ZnS殼之硫源及量子點表面結合配體二者)與十八烯(0.5mL)混合並用玻璃注射器注入所得溶液。使反應溶液在230℃下再保持1小
時30分鐘,在此期間發光明顯增強。使溶液冷卻至50℃並藉由添加甲苯/丙酮/甲醇混合物來分離奈米晶體,使其再分散於甲苯中且藉由添加乙腈實施再沉澱。使奈米晶體再溶解於無水甲苯中並在氮氣下儲存(參見圖7及8)。圖7係InP/ZnS核-殼奈米晶體之IR波譜,其中可觀察到C-H伸縮(2918cm-1);C=O伸縮(1558cm-1);C-O伸縮及C=C彎曲(1200-1118cm-1)。
PLmax=597nm,FWHM=72nm,PLQY=54%,UVmax=536nm,藉由TGA分析無機含量=55%。
Claims (13)
- 一種製造表面官能化之奈米顆粒之方法,該方法包含:在表面官能化配體存在下,使奈米顆粒前體物質反應而形成奈米顆粒,因而該表面官能化配體在原處結合至該奈米顆粒之表面;其中該表面官能化配體具有式X-Y-Z,其中X係奈米顆粒表面結合基團,Y係連接基團,且Z係官能基團,其中Y包含聚合物,及/或Z包含納入不飽和基團之脂肪族基團。
- 如請求項1之方法,其中該等奈米顆粒係核奈米顆粒。
- 如請求項1之方法,其中該等奈米顆粒係核-殼奈米顆粒。
- 如請求項1之方法,其中該反應及該結合係在非水性溶劑中實施。
- 如請求項1之方法,其中該聚合物包含聚乙二醇。
- 如請求項1之方法,其中該Y包含芳基。
- 如請求項1之方法,其中該X包含羧酸基或硫醇基。
- 如請求項1之方法,其中該不飽和基團係末端不飽和基團。
- 如請求項1之方法,其中該不飽和基團係乙烯基。
- 如請求項1之方法,其中該表面官能化配體包含可交聯基團。
- 如請求項10之方法,進一步包含使該表面官能化配體交聯。
- 一種表面官能化之奈米顆粒,其係藉由以下製備:在表面官能化配體存在下,使奈米顆粒前體物質反應而形成奈米顆粒,因而該表面官能化配體在原處結合至該奈米顆粒之表面;其中該表面官能化配體具有式X-Y-Z,其中X係奈米顆粒表面結合基團,Y係連接基團,且Z係官能基團,其中Y包含聚合物, 及/或Z包含納入不飽和基團之脂肪族基團。
- 一種組合物,其包含奈米顆粒前體物質,該奈米顆粒係與具有式X-Y-Z之表面官能化配體結合,其中X係奈米顆粒表面結合基團,Y係連接基團,且Z係官能基團,其中Y包含聚合物,及/或Z包含納入不飽和基團之脂肪族基團。
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2008
- 2008-08-07 GB GBGB0814458.6A patent/GB0814458D0/en not_active Ceased
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2009
- 2009-08-05 EP EP15190079.2A patent/EP3012224B1/en active Active
- 2009-08-05 EP EP09784875.8A patent/EP2310321B1/en active Active
- 2009-08-05 KR KR1020117005287A patent/KR101605394B1/ko active IP Right Grant
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- 2009-08-05 CN CN200980139861.5A patent/CN102177095B/zh active Active
- 2009-08-05 CN CN201710284844.7A patent/CN107266937B/zh active Active
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US8597730B2 (en) | 2013-12-03 |
TWI591014B (zh) | 2017-07-11 |
CA2733443A1 (en) | 2010-02-11 |
EP3012224B1 (en) | 2022-04-13 |
JP2011530187A (ja) | 2011-12-15 |
CN102177095B (zh) | 2017-04-26 |
KR101605394B1 (ko) | 2016-03-23 |
EP3012224A1 (en) | 2016-04-27 |
IL211049A (en) | 2015-08-31 |
TWI455887B (zh) | 2014-10-11 |
KR20160036072A (ko) | 2016-04-01 |
CN102177095A (zh) | 2011-09-07 |
US20100068522A1 (en) | 2010-03-18 |
KR20110044280A (ko) | 2011-04-28 |
US20140155640A1 (en) | 2014-06-05 |
AU2009278996A1 (en) | 2010-02-11 |
AU2009278996A2 (en) | 2011-03-03 |
WO2010015824A1 (en) | 2010-02-11 |
CN107266937A (zh) | 2017-10-20 |
HK1150238A1 (zh) | 2011-11-11 |
JP5661036B2 (ja) | 2015-01-28 |
GB0814458D0 (en) | 2008-09-10 |
CN107266937B (zh) | 2019-11-12 |
TW201012757A (en) | 2010-04-01 |
CA2733443C (en) | 2016-01-05 |
KR101700382B1 (ko) | 2017-01-26 |
EP2310321A1 (en) | 2011-04-20 |
EP2310321B1 (en) | 2016-04-20 |
IL211049A0 (en) | 2011-04-28 |
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