TWI461510B - Organic luminescent material - Google Patents
Organic luminescent material Download PDFInfo
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- TWI461510B TWI461510B TW100114068A TW100114068A TWI461510B TW I461510 B TWI461510 B TW I461510B TW 100114068 A TW100114068 A TW 100114068A TW 100114068 A TW100114068 A TW 100114068A TW I461510 B TWI461510 B TW I461510B
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- organic light
- emitting material
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- 239000000463 material Substances 0.000 title claims description 74
- 229910052751 metal Inorganic materials 0.000 claims description 39
- 239000002184 metal Substances 0.000 claims description 39
- 239000000376 reactant Substances 0.000 claims description 31
- 239000012295 chemical reaction liquid Substances 0.000 claims description 25
- 125000003277 amino group Chemical group 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 23
- 125000000524 functional group Chemical group 0.000 claims description 22
- 150000001412 amines Chemical class 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 19
- 239000007858 starting material Substances 0.000 claims description 18
- 125000000879 imine group Chemical group 0.000 claims description 17
- 238000005755 formation reaction Methods 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 150000002466 imines Chemical class 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 150000002576 ketones Chemical class 0.000 claims description 7
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 claims description 4
- 150000001299 aldehydes Chemical class 0.000 claims description 4
- 125000005233 alkylalcohol group Chemical group 0.000 claims description 4
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 claims description 4
- 229960002442 glucosamine Drugs 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 150000004676 glycans Chemical class 0.000 claims description 3
- 150000002772 monosaccharides Chemical class 0.000 claims description 3
- 229920005862 polyol Polymers 0.000 claims description 3
- 150000003077 polyols Chemical class 0.000 claims description 3
- 229920001282 polysaccharide Polymers 0.000 claims description 3
- 239000005017 polysaccharide Substances 0.000 claims description 3
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 125000005265 dialkylamine group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 description 21
- 238000000295 emission spectrum Methods 0.000 description 21
- 230000005284 excitation Effects 0.000 description 20
- 238000012921 fluorescence analysis Methods 0.000 description 16
- 238000002189 fluorescence spectrum Methods 0.000 description 16
- 238000000695 excitation spectrum Methods 0.000 description 14
- 230000005855 radiation Effects 0.000 description 14
- 229920001661 Chitosan Polymers 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000002096 quantum dot Substances 0.000 description 6
- RQFQJYYMBWVMQG-IXDPLRRUSA-N chitotriose Chemical compound O[C@@H]1[C@@H](N)[C@H](O)O[C@H](CO)[C@H]1O[C@H]1[C@H](N)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)[C@@H](CO)O1 RQFQJYYMBWVMQG-IXDPLRRUSA-N 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 230000007246 mechanism Effects 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 125000003172 aldehyde group Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000004696 coordination complex Chemical class 0.000 description 3
- 125000000468 ketone group Chemical group 0.000 description 3
- 230000031700 light absorption Effects 0.000 description 3
- 238000004020 luminiscence type Methods 0.000 description 3
- 239000002082 metal nanoparticle Substances 0.000 description 3
- 239000004005 microsphere Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229920002101 Chitin Polymers 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- UHYPYGJEEGLRJD-UHFFFAOYSA-N cadmium(2+);selenium(2-) Chemical compound [Se-2].[Cd+2] UHYPYGJEEGLRJD-UHFFFAOYSA-N 0.000 description 2
- 239000011258 core-shell material Substances 0.000 description 2
- -1 decylamino group Chemical group 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229920001542 oligosaccharide Polymers 0.000 description 2
- 150000002482 oligosaccharides Chemical class 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 231100000683 possible toxicity Toxicity 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- 229910004613 CdTe Inorganic materials 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 229910003771 Gold(I) chloride Inorganic materials 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001323 aldoses Chemical group 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 238000012984 biological imaging Methods 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000000090 biomarker Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 150000001893 coumarin derivatives Chemical class 0.000 description 1
- 125000006612 decyloxy group Chemical group 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 238000007877 drug screening Methods 0.000 description 1
- 238000004993 emission spectroscopy Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- MNQZXJOMYWMBOU-UHFFFAOYSA-N glyceraldehyde Chemical group OCC(O)C=O MNQZXJOMYWMBOU-UHFFFAOYSA-N 0.000 description 1
- 150000002337 glycosamines Chemical class 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- FDWREHZXQUYJFJ-UHFFFAOYSA-M gold monochloride Chemical compound [Cl-].[Au+] FDWREHZXQUYJFJ-UHFFFAOYSA-M 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000002707 nanocrystalline material Substances 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 150000001651 triphenylamine derivatives Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/04—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C251/06—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a saturated carbon skeleton
- C07C251/08—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a saturated carbon skeleton being acyclic
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
- C07F15/004—Iridium compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0046—Ruthenium compounds
- C07F15/0053—Ruthenium compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0086—Platinum compounds
- C07F15/0093—Platinum compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/02—Iron compounds
- C07F15/025—Iron compounds without a metal-carbon linkage
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/04—Nickel compounds
- C07F15/045—Nickel compounds without a metal-carbon linkage
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/06—Cobalt compounds
- C07F15/065—Cobalt compounds without a metal-carbon linkage
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B31/00—Preparation of derivatives of starch
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- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0024—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Glucans; (beta-1,3)-D-Glucans, e.g. paramylon, coriolan, sclerotan, pachyman, callose, scleroglucan, schizophyllan, laminaran, lentinan or curdlan; (beta-1,6)-D-Glucans, e.g. pustulan; (beta-1,4)-D-Glucans; (beta-1,3)(beta-1,4)-D-Glucans, e.g. lichenan; Derivatives thereof
- C08B37/0027—2-Acetamido-2-deoxy-beta-glucans; Derivatives thereof
- C08B37/003—Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
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- Polymers & Plastics (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Mycology (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Plural Heterocyclic Compounds (AREA)
- Electroluminescent Light Sources (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Luminescent Compositions (AREA)
Description
本發明是有關於一種有機發光材料,特別是指一種未含芳香環基團之有機發光材料。
奈米晶體材料,如CdS、CdSe、CdTe等量子點(quantum dots)由於具備特殊的物理及化學性質,故已被廣用於疾病檢測或藥物篩選等。在實際將量子點應用至生醫檢測領域時,除了需挑選具備高螢光量子產率之量子點外,更要求量子點需具備良好水溶性、良好生物相容性、高螢光強度及表面可修飾性。依據上述需求,雖然已研發出具有核殼結構之螢光微球(如CdSe/SiO2
),但是此螢光微球使用至生物體內時,仍存有生物毒性的疑慮。
由於量子點或具有核殼結構之螢光微球在運用至生物體內會產生潛在的毒性,加上量子點的粒徑較大而不易與生物體相容等問題,使得目前研究大多朝向具備較佳生物相容性、適當螢光產率及較佳光穩定性的金屬奈米原子簇(metallic nanoclusters)。金屬奈米原子簇,如金或銀奈米原子簇由於金屬實質含量較低,一般認為生物毒性應相對較低,所以有許多研究傾向使用金屬奈米原子簇進行生醫檢測與治療。金屬奈米原子簇因為粒徑甚小,通常僅含數個至數十個原子,因此,如何製備高穩定性、高螢光產率、易改質、高分散性之金屬奈米原子簇,依目前研究發展而言,仍存有困難。此外,運用貴重金屬的金屬奈米原子簇還需考量到原料的昂貴價格。
除了上述以金屬原子簇為主的發光材料外,有機發光材料亦為業界研究的目標之一,其大致可分為:有機小分子發光材料、有機高分子發光材料及有機錯合物發光材料。有機發光材料大多帶有芳香環或共軛雜環以及各種發色團,如三唑(triazole)及其衍生物類、香豆素類(coumarin)衍生物、三苯胺(triphenylamine)類衍生物等,可廣泛應用於光學電子器件、DNA診斷、染料、螢光增白劑、螢光塗料、有機電激發光元件等方面。上述有機發光材料的製作方法較為複雜,且因多數含有親油性之芳香環等結構,除有潛在毒性憂慮外,運用在生醫領域等高親水性之系統時,常需再透過包覆或改質的製程,克服其親水性之障礙,因而更增加應用上的複雜度。再者,有機小分子發光材料(染料)普遍存在光褪色(photobleaching)的問題,因此,光穩定性也是限制其應用發展的因素。
由上述可知,如能以有機發光材料為主,透過低生產成本及簡化的製程,研發一新穎並兼具不錯螢光強度、光穩定性且可選擇地含有金屬奈米原子簇之有機發光材料,應有助於成功應用至生醫領域,進而擴大有機發光材料的應用範圍。
本發明之目的,即在提供一種具有不錯螢光強度、光穩定性且可選擇地含有金屬奈米原子簇之有機發光材料。
於是,本發明有機發光材料係包含至少一亞胺基及至少一富含電子(electron-rich)之原子或官能基且未含有芳香環基團,該有機發光材料係由一反應液進行亞胺生成反應(imine formation reaction)所獲得,其中,該反應液是選自於A或B;該A包括一起始物及一溶劑,該起始物含有至少一胺基、至少一與該胺基反應並生成該亞胺基之反應基團,及至少一富含電子之原子或官能基;該B包括一含胺基分子及一不同於該含胺基分子之反應物,該反應物含有至少一與該胺基反應並生成一亞胺基之反應基團,且該含胺基分子與該反應物之其中至少一者含有至少一富含電子之原子或官能基。
本案發明人基於低成本及簡化製程,成功研發出一種新穎有機發光材料,其結構特性係含有至少一亞胺基及至少一富含電子之原子或官能基且未含有芳香環基團;本案發明人推導其發光機制是透過該亞胺基與該富含電子之原子或官能基產生交互作用[如未定域化作用(delocalization)]而發光;又,因為本發明有機發光材料不具有芳香環等疏水性結構,使得結構具親水性而得以增加生物相容性。
更值得一提的是,本發明可依據後續需求,透過適當選擇該反應液中之起始物、含胺基分子或反應物,而製得親水性高、生物相容性佳及光穩定性高之有機發光材料,同時讓本發明有機發光材料可廣泛應用於生醫領域。此外,本發明有機發光材料更可選擇地含有金屬單元,該金屬單元具備電子傳遞且可加強吸光功能,亦會參與上述發光機制而得以增加螢光強度及光穩定性。
本發明有機發光材料係包含至少一亞胺基及至少一富含電子之原子或官能基且未含有芳香環基團,該有機發光材料係由一反應液進行亞胺生成反應所獲得,其中,該反應液是選自於A或B;該A包括一起始物及一溶劑,該起始物含有至少一胺基、至少一與該胺基反應並生成該亞胺基之反應基團,及至少一富含電子之原子或官能基;該B包括一含胺基分子及一不同於該含胺基分子之反應物,該反應物含有至少一與該胺基反應並生成一亞胺基之反應基團,該含胺基分子與該反應物之其中至少一者含有至少一富含電子之原子或官能基。
上述之「亞胺基」係表示C=N基團,可涵蓋二級酮亞胺基(secondary ketimino group)或二級醛亞胺基(secondary aldimino group)。
上述之「富含電子之原子或官能基」可例如具有孤對電子之原子或官能基。該富含電子之原子包含但不限於氧原子、氮原子、硫原子等。該富含電子之官能基可為一價或二價基團,係包含但不限於羥基、醛基、酮基、醚基、矽氧基、胺基、硫醇基、醯胺基等等。
以下分別就反應液A及B進行詳細說明:
該反應液A包括一起始物及一溶劑,主要透過起始物進行自身亞胺生成反應而製得本發明有機發光材料。
該起始物含有至少一胺基、至少一與該胺基反應並生成該亞胺基之反應基團,及至少一富含電子之原子或官能基。上述之「反應基團」包含但不限於羥基、醛基、酮基等。
較佳地,該起始物是選自於葡萄胺糖(glucosamine)、聚葡萄胺糖(poly glucosamine)或此等之一組合。聚葡萄胺糖可例如幾丁寡聚醣(oligo chitosan)、幾丁聚醣(chitosan)等,幾丁寡聚醣或幾丁聚醣的結構同時具有胺基、作為反應基團之醛糖基(aldose group)及氧原子,非常適用於進行自身亞胺生成反應。於本發明之一具體例中,該起始物是幾丁寡聚醣。
該溶劑可為任何能溶解該起始物之溶劑,且可視後續應用進行挑選,例如當應用於生醫領域時,可選用無毒性且能溶解該起始物之溶劑。較佳地,該溶劑是選自於水、醇、酮、酯或此等之一組合。於本發明之一具體例中,該溶劑為水。
較佳地,該自身亞胺生成反應的溫度範圍為25℃~該反應液A的迴流溫度。
較佳地,該反應液A更包括一金屬鹽;更佳地,該金屬鹽為第8~11族金屬之鹽類;又更佳地,該金屬鹽為第8~11族金屬之鹵化物。上述之「第8~11族之金屬」是依據國際理論與應用化學聯盟(International Union of Pure and Applied Chemistry,IUPAC)予以界定,係包含Fe、Ru、Os、Co、Rh、Ir、Ni、Pd、Pt、Cu、Au及Ag。於本發明之具體例中,該金屬鹽是選自於AuCl3
、H2
PtCl6
‧6H2
O、CoCl2
‧6H2
O、IrCl3
、NiCl2
‧6H2
O、FeCl3
或RuCl3
。
較佳地,該金屬鹽與該起始物的莫耳比例範圍為1:3~1:30。
當該反應液A含有金屬鹽時,該有機發光材料是透過先將起始物、金屬鹽及溶劑進行混合後,再於一適當反應溫度下攪拌,以進行亞胺生成反應,推測最終所製得的有機發光材料為一金屬錯合物,此錯合物含有一金屬單元以及一配位化合物;其發光機制推測是以含有亞胺基之配位化合物為發光主體,而金屬單元則用於加強吸光及電子傳輸,藉以獲得較強螢光,同時能擴增吸光波長範圍。該金屬單元含有金屬奈米粒子或金屬原子簇。該配位化合物的結構未具有芳香環,且同時含有至少一亞胺基及至少一富含電子之原子或官能基。較佳地,該金屬單元之粒徑範圍為0.2~2 nm。
該反應液B包括一含胺基分子及一不同於該含胺基分子之反應物,該反應物含有至少一與該胺基反應並生成一亞胺基之反應基團,且該含胺基分子與該反應物之其中至少一者含有至少一富含電子之原子或官能基。上述之「反應基團」包含但不限於羥基、醛基、酮基等。
較佳地,該含胺基分子是選自於單胺基取代烷、二胺基取代烷、胺基矽氧烷、胺基酸、葡萄胺糖或聚葡萄胺糖。單胺基取代烷及二烷基取代烷的碳數範圍較佳為1~20;更佳為4~16。該聚葡萄胺糖可例如幾丁寡聚醣、幾丁聚醣等,其雖然可進行自身亞胺生成反應,但亦可與另一反應物進行亞胺生成反應。於本發明之具體例中,該含胺基分子是選自於1-丁胺(1-butylamine)、1-辛胺(1-octylamine)、1-十二烷基胺(1-dodecylamine)、1-十六烷基胺(1-hexadecylamine)、1,6-己二胺(1,6-hexadiamine)、3-胺基丙基三乙氧基矽烷(3-aminopropyltriethoxysilane,APTES)、或幾丁寡聚醣。
較佳地,該反應物是選自於醛類、酮類、烷基醇類、多元醇類、單糖類或聚糖類。
醛類或烷基醇類的碳數範圍較佳為1~10;更佳為1~6。
酮類的碳數範圍較佳為2~10;更佳為2~6。
多元醇為具有二個或二個以上之羥基的醇類,例如但不限於聚乙二醇(polyethylene glycol,PEG)。
單糖類包含但不限於葡萄糖、葡萄胺糖、果糖等。
聚糖類為具有二個或二個以上之糖單元之還原糖類,例如但不限於聚葡萄胺糖、乙醯化聚葡萄胺糖、麥芽糖(maltose)、糊精(dextrin)等等,其中聚葡萄胺糖例如但不限於幾丁寡聚醣、幾丁聚醣,乙醯化聚葡萄胺糖例如但不限於幾丁質(chitin)。
於本發明之具體例中,該反應物與該含胺基分子不同且選自於丙酮、甲醇、乙醇、丙醇、異丙醇、丁醇、戊醇、己醇、聚乙二醇(較佳具有分子量5000~7000)、幾丁寡聚醣或水溶性幾丁質。
需注意的是,該反應液B可選擇地更包括一溶劑;尤其當該含胺基分子及該反應物皆為固體時,該反應液B需包括一溶劑。該溶劑為任何能溶解該含胺基分子及該反應物的溶劑,其範圍及變化態樣如上述反應液A之溶劑,在此不再贅述。
較佳地,該亞胺生成反應的溫度範圍為25℃~該反應液B的迴流溫度。
該含胺基分子與該反應物的莫耳比例可視所挑選種類、使用溶劑等進行調整。較佳地,該含胺基分子與該反應物的莫耳比例範圍為1:20000~10:1。需注意的是,當該反應物為醛類、酮類或烷基醇類時,可視需要將用量增加,以同時做為溶劑使用。
較佳地,該反應液B更包括一金屬鹽。該金屬鹽的範圍、變化態樣及用量如上述反應液A之金屬鹽,在此不再贅述。
當該反應液B含有金屬鹽時,該有機發光材料是透過先將含胺基分子、反應物、金屬鹽及選擇添加之溶劑進行混合後,再於一適當反應溫度下進行亞胺生成反應,推測最終所製得的有機發光材料為一金屬錯合物及鄰近於該金屬錯合物且具有至少一富含電子之原子或官能基的分子或基團,此錯合物含有一金屬單元以及一配位化合物;其發光機制推測是以含有亞胺基之配位化合物為發光主體,而金屬單元則用於加強吸光及電子傳輸。該金屬單元含有金屬奈米粒子或金屬原子簇。該配位化合物的結構未具有芳香環,且含有至少一亞胺基。
上述反應液A或B所製得之有機發光材料可依據後續應用之所需進行分離純化或配製成其他形式。分離純化方式可例如:透析、層析、萃取、蒸餾、減壓濃縮等方式。
透過適當選擇之反應液中的起始物、含胺基分子或反應物,本發明有機發光材料除了在生物體內不會產生毒性之外,更具備生物相容性,且在可見光的激發下會發出螢光,所以可運用於生醫領域、光電領域及其他各種需運用發光材料之領域,例如觸媒催化、生物標記、生物影像等等。
本發明將就以下實施例來作進一步說明,但應瞭解的是,該實施例僅為例示說明之用,而不應被解釋為本發明實施之限制。
以下各實施例所使用之化學品及其來源整理於下表1中。
將50 mg之幾丁寡聚醣、50 mL水於室溫下進行混合,以獲得一反應液A。使該反應液A於90℃下進行攪拌,同時反應48小時,最後製得分散於水中之實施例1的有機發光材料。
實施例2~21的反應液B的組成、用量、反應溫度及時間如下表2。反應過程為:將含胺基分子、反應物、選擇添加之溶劑或金屬鹽於室溫下進行混合,以獲得反應液B。使該反應液B於表2所列溫度及時間下進行反應,最後製得分散於水中或其他溶劑(醇類或酮類)之有機發光材料。
需特別說明的是,在實施例2~14及17~21中,該富含電子之原子或官能基是存在於反應物中;且在實施例2及3中,該反應物的添加量較多,係因為此兩實施例中的反應物亦扮演溶劑角色,因此將會有部份反應物未反應完。在實施例4~14及21中,雖然反應物的添加量沒有較多,但另外添加金屬鹽。在實施例15中,該富含電子之原子或官能基是存在於該含胺基分子中。在實施例16中,該富含電子之原子或官能基是同時存在於該含胺基分子及該反應物中。
利用螢光光譜儀(Fluorescence Spectrophotometer,由HITACHI所製造,型號F-4500)分別對上述實施例1~21之有機發光材料進行激發光譜及放射光譜分析,依材料不同,分別選擇不同激發波長以及放射波長。測試結果分別如圖1~圖15所示,其中,圖4為實施例4~7的結果,圖5為實施例8~11的結果。在圖1~圖15中,a曲線代表激發光譜,b曲線代表放射光譜,a或b前的數字代表實施例編號。此外,在圖1中,右下角附圖皆為盛裝有實施例1之有機發光材料的樣品照片,其中左側為未照射紫外光的樣品照片,右側為在365 nm之紫外光照射下的樣品照片。
透過圖1之附圖可發現,實施例1之有機發光材料會發出藍色螢光。其餘實施例2~21經本發明人實驗後,也發現實施例2~21之有機發光材料同樣發出藍色螢光。
再由圖1~圖15之螢光光譜結果,可發現依材料不同,最佳激發波長及放射波長雖有差異,但均可發出具有相當強度之螢光。
將實施例21之有機發光材料進行穩定性分析。樣品測試前處理以11,000 rpm離心去除較大顆的粒子,並移除下層水,再以減壓濃縮機去除殘餘水後,以功率12瓦特之紫外燈,於暗箱中距離樣品約10公分之距離,持續照射曝光15小時,每5個小時以螢光光譜儀量測螢光強度(激發波長365nm),其結果如圖15所示。圖15中,21b曲線表示未曝光前之放射光譜,21c曲線表示曝光5小時後之放射光譜,21d曲線表示曝光10小時後之放射光譜,及21e曲線表示曝光15小時後之放射光譜。
由圖15之結果可知,實施例21之有機發光材料在持續曝光15小時後,螢光強度雖有減弱,但仍在業界可應用的範圍內,顯示本發明有機發光材料具備符合業界需求的光穩定性。
綜上所述,本發明有機發光材料的結構特性係含有至少一亞胺基及至少一富含電子之原子或官能基且未含有芳香環基團,藉此可具備不錯螢光強度及光穩定性。另外,本發明有機發光材料為無毒且對人體無任何損害之材料,所以非常適合運用於生醫領域。更值得一提的是,本發明之製法僅需單一步驟即可完成,且所使用之原料便宜且無毒性。
惟以上所述者,僅為本發明之較佳實施例而已,當不能以此限定本發明實施之範圍,即大凡依本發明申請專利範圍及發明說明內容所作之簡單的等效變化與修飾,皆仍屬本發明專利涵蓋之範圍內。
圖1是一螢光光譜圖,說明依據本發明之有機發光材料之實施例1的螢光分析結果,其中1a曲線代表激發光譜(放射波長為440 nm),1b曲線代表放射光譜(激發波長為365 nm),右下角附圖皆為盛裝有實施例1之有機發光材料的樣品照片,左側為未照射紫外光的樣品照片,右側為在365 nm之紫外光照射下的樣品照片;
圖2是一螢光光譜圖,說明依據本發明之有機發光材料之實施例2的螢光分析結果,其中2a曲線代表激發光譜(放射波長為440 nm),2b曲線代表放射光譜(激發波長為365 nm);
圖3是一螢光光譜圖,說明依據本發明之有機發光材料之實施例3的螢光分析結果,其中3a曲線代表激發光譜(放射波長為450 nm),3b曲線代表放射光譜(激發波長為365 nm);
圖4是一螢光光譜圖,說明依據本發明之有機發光材料之實施例4~7的螢光分析結果,其中4a~7a曲線代表激發光譜(放射波長分別為440或445 nm),4b~7b曲線代表放射光譜(激發波長分別為365nm);
圖5是一螢光光譜圖,說明依據本發明之有機發光材料之實施例8~11的螢光分析結果,其中8b~11b曲線代表放射光譜(激發波長分別為365 nm);
圖6是一螢光光譜圖,說明依據本發明之有機發光材料之實施例12的螢光分析結果,其中12a曲線代表激發光譜(放射波長為450 nm),12b曲線代表放射光譜(激發波長為365 nm);
圖7是一螢光光譜圖,說明依據本發明之有機發光材料之實施例13的螢光分析結果,其中13a曲線代表激發光譜(放射波長為445 nm),13b曲線代表放射光譜(激發波長為365 nm);
圖8是一螢光光譜圖,說明依據本發明之有機發光材料之實施例14的螢光分析結果,其中14a曲線代表激發光譜(放射波長為450 nm),14b曲線代表放射光譜(激發波長為340 nm);
圖9是一螢光光譜圖,說明依據本發明之有機發光材料之實施例15的螢光分析結果,其中15a曲線代表激發光譜(放射波長為440 nm),15b曲線代表放射光譜(激發波長為365 nm);
圖10是一螢光光譜圖,說明依據本發明之有機發光材料之實施例16的螢光分析結果,其中16a曲線代表激發光譜(放射波長為450 nm),16b曲線代表放射光譜(激發波長為365 nm);
圖11是一螢光光譜圖,說明依據本發明之有機發光材料之實施例17的螢光分析結果,其中17a曲線代表激發光譜(放射波長為450 nm),17b曲線代表放射光譜(激發波長為365 nm);
圖12是一螢光光譜圖,說明依據本發明之有機發光材料之實施例18的螢光分析結果,其中18a曲線代表激發光譜(放射波長為450 nm),18b曲線代表放射光譜(激發波長為365 nm);
圖13是一螢光光譜圖,說明依據本發明之有機發光材料之實施例19的螢光分析結果,其中19a曲線代表激發光譜(放射波長為440 nm),19b曲線代表放射光譜(激發波長為350 nm);
圖14是一螢光光譜圖,說明依據本發明之有機發光材料之實施例20的螢光分析結果,其中20a曲線代表激發光譜(放射波長為440 nm),20b曲線代表放射光譜(激發波長為350 nm);及
圖15是一螢光光譜圖,說明依據本發明之有機發光材料之實施例21的螢光分析結果,其中21b曲線代表放射光譜(激發波長為365 nm),21c曲線表示曝光5小時後之放射光譜,21d曲線表示曝光10小時後之放射光譜,及21e曲線表示曝光15小時後之放射光譜。
Claims (10)
- 一種有機發光材料,係包含至少一亞胺基及至少一富含電子之原子或官能基且未含有芳香環基團,該有機發光材料係由一反應液進行亞胺生成反應所獲得,其中,該反應液是選自於A或B;該A包括一起始物及一溶劑,該起始物含有至少一胺基、至少一與該胺基反應並生成該亞胺基之反應基團,及至少一富含電子之原子或官能基;該B包括一含胺基分子及一不同於該含胺基分子之反應物,該反應物含有至少一與該胺基反應並生成一亞胺基之反應基團,且該含胺基分子與該反應物之其中至少一者含有至少一富含電子之原子或官能基。
- 根據申請專利範圍第1項所述之有機發光材料,其中,該起始物是選自於葡萄胺糖、聚葡萄胺糖或此等之一組合。
- 根據申請專利範圍第2項所述之有機發光材料,其中,該溶劑是選自於水、醇、酮、酯或此等之一組合。
- 根據申請專利範圍第3項所述之有機發光材料,其中,該亞胺生成反應的溫度範圍為25℃~該A的迴流溫度。
- 根據申請專利範圍第1項所述之有機發光材料,其中,該含胺基分子是選自於單胺基取代烷、二胺基取代烷、二烷基胺、胺基矽氧烷、胺基酸、葡萄胺糖或聚葡萄胺糖。
- 根據申請專利範圍第5項所述之有機發光材料,其中,該反應物是選自於醛類、酮類、烷基醇類、多元醇類、單糖類或聚糖類。
- 根據申請專利範圍第6項之有機發光材料,其中,該亞胺生成反應的溫度範圍為25℃~該B的迴流溫度。
- 根據申請專利範圍第1項所述之有機發光材料,其中,該A更包括一金屬鹽。
- 根據申請專利範圍第1項所述之有機發光材料,其中,該B更包括一金屬鹽。
- 根據申請專利範圍第8或9項所述之有機發光材料,其中,該金屬鹽為第8~11族金屬之鹽類。
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