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(12) United States Patent (10) Patent No.: US 9,517,936 B2 Jeong Et Al

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(12) United States Patent (10) Patent No.: US 9,517,936 B2 Jeong Et Al USO09517936 B2 (12) United States Patent (10) Patent No.: US 9,517,936 B2 Jeong et al. (45) Date of Patent: Dec. 13, 2016 (54) QUANTUM DOT STABILIZED BY HALOGEN (2013.01); COIB 21/06 (2013.01); COIB SALT AND METHOD FOR 21/0632 (2013.01); COIB 21/072 (2013.01); MANUFACTURING THE SAME C07C 51/418 (2013.01); C07C 57/12 (2013.01); B82Y 30/00 (2013.01); B82Y 40/00 (71) Applicant: KOREA INSTITUTE OF (2013.01); COIP 2004/64 (2013.01); Y10S MACHINERY & MATERIALS, 977/774 (2013.01); Y10S 977/896 (2013.01) Daejeon (KR) (58) Field of Classification Search CPC ............................. C01B 19/002: C07C 51/418 (72) Inventors: Sohee Jeong, Daejeon (KR); Ju Young USPC .......................................................... 55.6/105 Woo, Gyeonggi-do (KR); Doh Chang See application file for complete search history. Lee, Daejeon (KR); Won Seok Chang, Daejeon (KR); Duck Jong Kim, Daejeon (KR) (56) References Cited KOREA INSTITUTE OF (73) Assignee: PUBLICATIONS MACHINERY & MATERIALS, Daejeon (KR) Traub et al., J. Am. Chem. Soc. 2008, 130,955-964.* Peng et al., J. Am. Chem. Soc. 1997, 119, 7019-7029.* (*) Notice: Subject to any disclaimer, the term of this Bae et al., J. Am. Chem. Soc. 2012, 134, 20160-20168.* patent is extended or adjusted under 35 Wan Ki Bae et al., “Highly Effective Surface Passivation of PbSe U.S.C. 154(b) by 0 days. Quantum Dots through Reaction with Molecular Chlorine,” J. Am. Chem.Soc., 2012, 134, pp. 20160-20168. (21) Appl. No.: 14/677.999 Aaron T. Fafarman et al., “Air-Stable, Nanostructured Electronic and Plasmonic Materials from Solution-Processable, Silver Filed: Apr. 3, 2015 Nanocrystal Building Blocks.” American Chemical Society, 2014. (22) vol. 8, No. 3, pp. 2746-2754. www.acsnano.org. Prior Publication Data (65) * cited by examiner US 2015/0291422 A1 Oct. 15, 2015 Primary Examiner — Porfirio Nazario Gonzalez (30) Foreign Application Priority Data Assistant Examiner — Kofi Adzamli Apr. 11, 2014 (KR) ........................ 10-2014-0043.638 (74) Attorney, Agent, or Firm — Hauptman Ham, LLP (51) Int. C. (57) ABSTRACT C07F 7/00 (2006.01) COIB 9/00 (2006.01) A quantum dot stabilized by a halogen salt includes a C07C 57/12 (2006.01) compound of Group 13 and Group 15, a compound of Group CD7C5L/4I (2006.01) 12 and Group 16 or a compound of Group 14 and Group 16. COIB 2/06 (2006.01) The quantum dot has a crystalline structure and at least a COB 21/072 (2006.01) portion of a surface of the quantum dot is combined with a B82Y 4O/OO (2011.01) halogen salt. Thus, the quantum dot has a high Stability in an B82Y 3O/OO (2011.01) a1. (52) U.S. C. CPC ........... COIB 19/002 (2013.01); COIB 19/007 6 Claims, 7 Drawing Sheets U.S. Patent Dec. 13, 2016 Sheet 1 of 7 US 9,517,936 B2 - X /10xygen X X-Pb Se202,sey SeO2 X X X U.S. Patent Dec. 13, 2016 Sheet 2 of 7 US 9,517,936 B2 F. G. 2 REACTING FIRST PRECURSOR WITH ORGANIC ACD S10 REACTING SECOND PRECURSOR WITH REACT ON PRODUCT OF THE FIRST PRECURSOR AND THE ORGANIC ACID PROVIDING HALOGEN COMPOUND STABILIZE QUANTUM DOT S30 U.S. Patent Dec. 13, 2016 Sheet 3 of 7 US 9,517,936 B2 U.S. Patent Dec. 13, 2016 Sheet 4 of 7 US 9,517,936 B2 FIG 4A Pb 4f, AS prepared NH4C treated 155 150 145 140 135 130 Binding Energy (eV) FG. 4B Pb 4f, AS prepared PriStine 155 150 145 140 135 130 Binding Energy (eV) U.S. Patent Dec. 13, 2016 Sheet 5 of 7 US 9,517,936 B2 FG 5A Se 3d NH4C treated AS prepared 70 65 60 55 50 45 Binding Energy (eV) FIG 5B Se 3d PriStine AS prepared 70 65 60 55 50 45 Binding Energy (eV) U.S. Patent Dec. 13, 2016 Sheet 6 of 7 US 9,517,936 B2 F.G. 6A -100 -- Pristine -150- -O-NH4F -A-NH4C - V - NH4Br O 7 14. Time (day) F.G. 6B 5 O -100 -150 -- Pristine -200 -250- 7 14 21 Time(day) U.S. Patent Dec. 13, 2016 Sheet 7 Of 7 US 9,517,936 B2 FG 60 -- Pristine -O-NH4Br/MeOH -A- TBABr/MeOH - V - CTAB/MeOH -(- TBABr/MeCN O 2 4 6 8 10 Time(day) US 9,517,936 B2 1. 2 QUANTUM DOT STABILIZED BY HALOGEN germanium Sulfide (GeS), germanium selenide (GeSe), ger SALT AND METHOD FOR manium telluride (GeTe), tin selenium sulfide (SnSeS), tin MANUFACTURING THE SAME selenium telluride (SnSeTe), tin sulfide telluride (SnSTe), lead selenium sulfide (PbSeS), lead selenium telluride (Pb CROSS-REFERENCE TO RELATED SeTe), lead sulfide telluride (PbSTe), tin lead sulfide (Sn APPLICATIONS PbS), tin lead selenide (SnPbSe), tin lead telluride (SnPbTe), tin oxide sulfide (SnOS), tin oxide selenide (SnOSe), tin This application claims priority under 35 U.S.C. S 119 to oxide telluride (SnOTe), germanium oxide sulfide (GeOS), Korean Patent Application No. 10-2014-0043638, filed on germanium oxide selenide (GeOSe), germanium oxide tel Apr. 11, 2014, and all the benefits accruing therefrom, the 10 luride (GeOTe), tin lead sulfide selenide (SnPbSSe), tin lead content of which is herein incorporated by reference in its selenium telluride (SnPbSeTe) and tin lead sulfide telluride entirety. (SnRbSTe). In an exemplary embodiment, the compound of Group 13 BACKGROUND and Group 15 includes at least one selected from the group 15 consisting of gallium phosphide (GaP), gallium arsenide 1. Field (GaAs), gallium antimonide (GaSb), gallium nitride (GaN), Exemplary embodiments relate to a quantum dot. More aluminum phosphide (AlP), aluminum arsenide (AlAS), particularly, exemplary embodiments relate to a quantum aluminum antimonide (AISb), aluminum nitride (AIN), dot stabilized by a halogen salt and a method for manufac indium phosphide (InP), indium arsenide (InAs), indium turing the quantum dot. antimonide (InSb), indium nitride (InN), gallium phosphide 2. Description of the Related Art arsenide (GaPAs), gallium phosphide antimonide (GaPSb), A quantum dot is a nano-particle having semiconductive gallium phosphide nitride (GaPN), gallium arsenide nitride properties and having a size less than tens of nanometers. (GaAsN), gallium antimonide nitride (GaSbN), aluminum The quantum dot has properties different from a bulk particle phosphide arsenide (AlPAS), aluminum phosphide anti due to quantum confinement effect. For example, the quan 25 monide (AlPSb), aluminum phosphide nitride (AlPN), alu tum dot can change a wavelength of a light, which the minum arsenide nitride (AlASN), aluminum antimonide quantum dot absorbs, according to a size thereof. Further nitride (AISbN), indium phosphide arsenide (InPAs), indium more, the quantum dot has novel optical, electrical and phosphide antimonide (InPSb), indium phosphide nitride physical properties that the bulk particle does not have. (InPN), indium arsenide nitride (InAsN), indium antimonide Thus, researches are being conducted for manufacturing a 30 nitride (InSbN), aluminum gallium phosphide (AlGaP), alu photoelectric conversion device Such as a Solar cell, a minum gallium arsenide (AlGaAs), aluminum gallium anti light-emitting diode or the like. monide (AlGaSb), aluminum gallium nitride (AlGaN), alu Recently, a colloidal chemosynthesis has been developed minum arsenide nitride (AlASN), aluminum antimonide for controlling a size and a shape of the quantum dot. nitride (AISbN), indium gallium phosphide (InGaP), indium However, the quantum dot manufactured by the colloidal 35 gallium arsenide (InGaAs), indium gallium antimonide (In chemosynthesis has a low stability in an air. A core-shell GaSb), indium gallium nitride (InGaN), indium arsenide quantum dot having a thick skin may be relatively stable in nitride (InAsN), indium antimonide nitride (InSbN), alumi an air. However, the core-shell quantum dot is hardly num indium phosphide (AlInP), aluminum indium arsenide applicable for the photoelectric conversion device, and (AlInAs), aluminum indium antimonide (AlInSb), alumi manufacturing processes for the core-shell quantum dot are 40 num indium nitride (AlInN), aluminum arsenide nitride complicated. (AlAsN), aluminum antimonide nitride (AISbN), aluminum phosphide nitride (AlPN), gallium aluminum phosphide SUMMARY arsenide (GaAlPAS), gallium aluminum phosphide anti monide (GaAlPSb), gallium indium phosphide arsenide Exemplary embodiments provide a quantum dot stable in 45 (GalinPAS), gallium indium aluminum arsenide (GanAlAS), an air. gallium aluminum phosphide nitride (GaAlPN), gallium Exemplary embodiments also provide a method for manu aluminum arsenide nitride (GaA1ASN), gallium aluminum facturing the quantum dot. antimonide nitride (GaA1SbN), gallium indium phosphide According to an exemplary embodiment, a quantum dot nitride (GainPN), gallium indium arsenide nitride (Gain stabilized by a halogen salt includes a compound of Group 50 ASN), gallium indium aluminum nitride (GanAIN), gallium 13 and Group 15, a compound of Group 12 and Group 16 or antimonide phosphide nitride (GaSbPN), gallium arsenide a compound of Group 14 and Group 16. The quantum dot phosphide nitride (GaAsPN), gallium arsenide antimonide has a crystalline structure, and at least a portion of a surface nitride (GaAsSbN), gallium indium phosphide antimonide of the quantum dot is combined with a halogen salt. (GalnPSb), gallium indium phosphide nitride (GalnPN), In an exemplary embodiment, a diameter of the quantum 55 gallium indium antimonide nitride (GainSbN), gallium dot is 1 nm to 20 nm. phosphide antimonide nitride (GaPSbN), indium aluminum In an exemplary embodiment, the quantum dot has a first phosphide arsenide (InAlPAS), indium aluminum phosphide Surface combined with the halogen salt and a second Surface nitride (InAlPN), indium phosphide arsenide nitride (In combined with an organic ligand. PASN), indium aluminum antimonide nitride (InAlSbN), In an exemplary embodiment, a (100) surface is combined 60 indium
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