JP7317376B2 - 希土類錯体、発光材料、発光体、発光デバイス、合わせガラス用中間膜、合わせガラス、車両用フロントガラス、波長変換材料及びセキュリティ材料 - Google Patents
希土類錯体、発光材料、発光体、発光デバイス、合わせガラス用中間膜、合わせガラス、車両用フロントガラス、波長変換材料及びセキュリティ材料 Download PDFInfo
- Publication number
- JP7317376B2 JP7317376B2 JP2020530150A JP2020530150A JP7317376B2 JP 7317376 B2 JP7317376 B2 JP 7317376B2 JP 2020530150 A JP2020530150 A JP 2020530150A JP 2020530150 A JP2020530150 A JP 2020530150A JP 7317376 B2 JP7317376 B2 JP 7317376B2
- Authority
- JP
- Japan
- Prior art keywords
- rare earth
- group
- condensed polycyclic
- polycyclic aromatic
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 229910052761 rare earth metal Inorganic materials 0.000 title claims description 66
- 150000002910 rare earth metals Chemical class 0.000 title claims description 46
- 239000000463 material Substances 0.000 title claims description 23
- 238000006243 chemical reaction Methods 0.000 title claims description 22
- 239000005340 laminated glass Substances 0.000 title claims description 14
- 239000011229 interlayer Substances 0.000 title claims description 6
- 239000003446 ligand Substances 0.000 claims description 44
- 125000003118 aryl group Chemical group 0.000 claims description 41
- -1 rare earth ion Chemical class 0.000 claims description 38
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 claims description 12
- 125000005594 diketone group Chemical group 0.000 claims description 8
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 239000011521 glass Substances 0.000 claims description 3
- 239000010410 layer Substances 0.000 claims description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- 239000000243 solution Substances 0.000 description 30
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- 239000000843 powder Substances 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- 101800000089 Movement protein P3N-PIPO Proteins 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000013078 crystal Substances 0.000 description 9
- 238000000921 elemental analysis Methods 0.000 description 9
- 238000002284 excitation--emission spectrum Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 6
- 238000000967 suction filtration Methods 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 5
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 229910052693 Europium Inorganic materials 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000012300 argon atmosphere Substances 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- KTAIYEDBIBXRJO-UHFFFAOYSA-N 5-bromopicene Chemical compound C12=CC=CC=C2C(Br)=CC2=C1C=CC1=C(C=CC=C3)C3=CC=C21 KTAIYEDBIBXRJO-UHFFFAOYSA-N 0.000 description 3
- FAAAKDIORRDGMS-UHFFFAOYSA-N 6-bromochrysene Chemical compound C1=CC=C2C(Br)=CC3=C(C=CC=C4)C4=CC=C3C2=C1 FAAAKDIORRDGMS-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000004431 deuterium atom Chemical group 0.000 description 3
- 238000004455 differential thermal analysis Methods 0.000 description 3
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 3
- 238000000295 emission spectrum Methods 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 238000000695 excitation spectrum Methods 0.000 description 3
- 230000031700 light absorption Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
- 235000011056 potassium acetate Nutrition 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000002411 thermogravimetry Methods 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- 229910052805 deuterium Inorganic materials 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- GBROPGWFBFCKAG-UHFFFAOYSA-N picene Chemical compound C1=CC2=C3C=CC=CC3=CC=C2C2=C1C1=CC=CC=C1C=C2 GBROPGWFBFCKAG-UHFFFAOYSA-N 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- NQYPPAVHIMLEFQ-UHFFFAOYSA-N 5-diphenylphosphorylpicene Chemical compound C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)C1=C2C=CC=CC2=C2C=CC3=C4C=CC=CC4=CC=C3C2=C1 NQYPPAVHIMLEFQ-UHFFFAOYSA-N 0.000 description 1
- MSRUHHVYFFDSFY-UHFFFAOYSA-N 6,12-bis(diphenylphosphoryl)chrysene Chemical compound C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)C=1C=C2C=3C=CC=CC=3C(=CC2=C2C=CC=CC=12)P(=O)(C1=CC=CC=C1)C1=CC=CC=C1 MSRUHHVYFFDSFY-UHFFFAOYSA-N 0.000 description 1
- RULVBMDEPWAFIN-UHFFFAOYSA-N 6,12-dibromochrysene Chemical compound C1=CC=C2C(Br)=CC3=C(C=CC=C4)C4=C(Br)C=C3C2=C1 RULVBMDEPWAFIN-UHFFFAOYSA-N 0.000 description 1
- BYGYWCBDJMJCAP-UHFFFAOYSA-N 6-diphenylphosphorylchrysene Chemical compound C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)C=1C=C2C=3C=CC=CC=3C=CC2=C2C=CC=CC=12 BYGYWCBDJMJCAP-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- 229910052779 Neodymium Inorganic materials 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000011540 sensing material Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/003—Compounds containing elements of Groups 3 or 13 of the Periodic Table without C-Metal linkages
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L33/48—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor body packages
- H01L33/50—Wavelength conversion elements
- H01L33/501—Wavelength conversion elements characterised by the materials, e.g. binder
- H01L33/502—Wavelength conversion materials
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
- B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
- B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
- B32B17/10005—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
- B32B17/10009—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the number, the constitution or treatment of glass sheets
- B32B17/10036—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the number, the constitution or treatment of glass sheets comprising two outer glass sheets
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
- B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
- B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
- B32B17/10005—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
- B32B17/10165—Functional features of the laminated safety glass or glazing
- B32B17/10174—Coatings of a metallic or dielectric material on a constituent layer of glass or polymer
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
- B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
- B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
- B32B17/10005—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
- B32B17/1055—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer
- B32B17/10761—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer containing vinyl acetal
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
-
- C—CHEMISTRY; METALLURGY
- 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
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B27/00—Optical systems or apparatus not provided for by any of the groups G02B1/00 - G02B26/00, G02B30/00
- G02B27/01—Head-up displays
- G02B27/0101—Head-up displays characterised by optical features
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L33/48—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor body packages
- H01L33/50—Wavelength conversion elements
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/351—Metal complexes comprising lanthanides or actinides, e.g. comprising europium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2605/00—Vehicles
- B32B2605/08—Cars
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B27/00—Optical systems or apparatus not provided for by any of the groups G02B1/00 - G02B26/00, G02B30/00
- G02B27/01—Head-up displays
- G02B2027/0192—Supplementary details
- G02B2027/0194—Supplementary details with combiner of laminated type, for optical or mechanical aspects
Landscapes
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Computer Hardware Design (AREA)
- Manufacturing & Machinery (AREA)
- Power Engineering (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Inorganic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Optical Filters (AREA)
Description
1.希土類錯体の合成
1-1.配位子前駆体:6-ブロモクリセン
1H-NMR(400 MHz, CDCl3/TMS) δ/ppm = 9.07(s, 1H),8.80(d, 1H, J = 7.2 Hz), 8.71(dd, 2H, J = 9.6 Hz, 10 Hz), 8.45(d, 1H, J = 9.6Hz), 8.02(dd, 2H, J = 9.2 Hz, 6.0 Hz), 7.79-7.72(m, 3H), 7.68-7.65(m, 1H)
1H-NMR(400 MHz, CDCl3/TMS) δ/ppm = 8.83 (d, 1H, J= 8.0 Hz), 8.73 (dd, 2H, J = 6.0 Hz, 3.2 Hz), 8.63 (d, 1H, J = 17 Hz), 8.11 (d,1H, J = 9.2 Hz), 8.05 (d, 1H, J = 8.0 Hz), 8.98 (d, 1H, J = 8.0 Hz), 7.79 (dd,4H, J = 6.8 Hz, 5.2 Hz), 7.71 (t, 1H, J = 8.0 Hz, 7.6 Hz), 7.65-7.50 (m, 9H)
ESI-MS: m/z calcd. for C30H22OP[M+H]+ = 429.14; found: 429.14
elemental analysis calcd. (%) for C30H21OP+0.5CH2Cl2,C 77.79, H 4.71; found: C 77.66, H 4.53
ESI-MS: m/z calcd for C70H41EuF12O6P2[M-hfa]+ = 1421.15; found: 1421.16
elemental analysis calcd. (%) for C75H42EuF18O8P2+0.5CH2Cl2,C 53.32, H 2.59; found: C 53.52, H 2.52
IR (ATR) = 1653 (st, C=O), 1251 (st, C-F),1133 (st, P=O) cm-1
2-1.紫外可視光吸収
Eu(hfa)3(DPCO)2及びEu(hfa)3(TPPO)2の紫外可視光吸収特性を、これらの重クロロホルム溶液を用いて測定した。図1は、Eu(hfa)3(DPCO)2及びEu(hfa)3(TPPO)2の紫外可視光吸収スペクトルである。Eu(hfa)3(DPCO)2は、最大約500000cm-1M-1という、Eu(III)錯体としては極めて大きなモル吸光係数を示した。
図2は、Eu(hfa)3(DPCO)2の励起発光スペクトルである。励起スペクトルは、Eu(hfa)3(DPCO)2のCDCl3溶液を用い、蛍光波長λemを610nmとして測定された。発光スペクトルは、Eu(hfa)3(DPCO)2の粉体を用い、励起波長λexを380nmとして測定された。Eu(hfa)3(DPCO)2の365nmにおける一分子当たりの発光強度は、Eu(hfa)3(TPPO)2の既存のデータと比較して40倍以上であった。
図3は、Eu2(hfa)6(DPCO)2及びEu(hfa)3(TPPO)2の熱重量・示差熱分析の結果を示すグラフである。Eu2(hfa)6(DPCO)2が300℃を超える高い分解温度を示すことが確認された。
図4は、Eu2(hfa)6(DPCO)2の発光寿命と温度との関係を示すグラフである。Eu2(hfa)6(DPCO)2の発光寿命は温度に依存して大きく変化することが確認された。したがって、本発明の一側面に係る希土類錯体は、強発光特性とともに、温度検知の機能も有する。
1.希土類錯体の合成
1-1.配位子前駆体:5-ブロモピセン
1H-NMR (400 MHz, CDCl3/TMS) δ/ppm = 9.14 (s, 1H), 9.02-8.91 (m, 2H), 8.86 (t, 2H, J = 7.6 Hz, 8.4 Hz), 8.70 (d, 1H, J = 9.7 Hz), 8.47 (dd, 1H, J = 6.3 Hz, 2.1 Hz), 8.05 (dd, 2H, J = 4.4 Hz, 9.2 Hz), 7.82-7.44 (m, 3H), 7.68 (t, 1H, J = 8.0 Hz, 8.4 Hz)
1H-NMR (400 MHz, CDCl3/TMS) δ/ppm = 9.06 (d, 1H, J = 9.6 Hz), 8.96 (d, 1H, J = 9.2 Hz), 8.90 (d, 1H, J = 8.4), 8.84 (d, 1H, J = 8.8 Hz), 8.72 (t, 2H, J = 8.4 Hz, 9.2 Hz), 7.96 (d, 1H, J = 8.0 Hz), 7.90 (d, 1H, J = 9.2 Hz), 7.83 (dd, 2H, J = 6.8 Hz, 1.2 Hz), 7.69-7.62 (m, 3H), 7.59-7.52 (m, 5H)
ESI-MS: m/z calcd. for C34H24OP, [M+H]+ = 479.16; found: 479.16; elemental analysis calcd. (%) for C 85.34, H 4.84; found: C 84.67, H 4.70
ESI-MS: m/z calcd. for C78H48EuF12O6P2, [M-hfa]+ = 1523.19; found: 1523.18; elemental analysis calcd. (%) for C 57.62, H 2.85, found: C 56.99, H: 2.60; IR (ATR) = 1653 (st, C=O), 1252 (st, C-F), 1145 (st, P=O) cm-1
図5は、Eu(hfa)3(PIPO)2の励起発光スペクトルである。励起スペクトルは、Eu(hfa)3(PIPO)2のCHCl3溶液(9.8×10-5M)を用い、蛍光波長λemを610nmとして測定された。発光スペクトルは、Eu(hfa)3(PIPO)2の粉体を用い、励起波長λexを390nmとして測定された。Eu(hfa)3(PIPO)2の365nmにおける一分子当たりの発光強度は、Eu(hfa)3(TPPO)2の既存のデータと比較して20倍以上であった。
1.希土類錯体の合成
1-1.配位子:6,12-ビス(ジフェニルホスホリル)クリセン(6,12-DPCO)
1H-NMR (400 MHz, CDCl3/TMS) δ/ppm = 8.73 (d, 2H, J = 8.4 Hz), 8.63 (s, 1H), 8.59 (s, 1H), 8.08 (d, 2H, J = 8.4 Hz), 7.78 (dd, 8H, J = 4.0 Hz, 8.0 Hz), 7.63 (t, 4H, J = 8.0 Hz, 6.8 Hz), 7.58-7.49 (m, 12H)
ESI-MS: m/z calcd. for C42H31O2P2, [M+H]+ = 629.18; found: 629.18; elemental analysis calcd. (%) for C 80.12, H 4.96; found: C 79.97, H 4.66
ESI-MS: m/z calcd. for C52H32EuF12O6P2, [M-hfa]+ = 1195.07; found: 1195.14, calcd. for C109H65Eu2F30O14P42, [M-hfa]+ = 2596.13; found: 2596.27, calcd. for C151H95Eu2F30O16P6, [M-hfa]+ = 3225.30; found: 3225.43
elemental analysis calcd. (%) for C 48.84, H 2.37; found: C 49.05, H 2.48; IR (ATR) = 1653 (st, C=O), 1253 (st, C-F), 1145 (st, P=O) cm-1
図6は、[Eu(hfa)3(6,12-DPCO)]nの励起発光スペクトルである。励起スペクトルは、[Eu(hfa)3(6,12-DPCO)]nの粉体を用い、蛍光波長λemを610nmとして測定された。発光スペクトルは、[Eu(hfa)3(6,12-DPCO)]nの粉体を用い、励起波長λexを390nmとして測定された。単核錯体と同様に高輝度発光を示した。
Claims (12)
- 希土類イオンと、該希土類イオンに配位結合し縮合多環芳香族基を有する配位子と、を備え、
前記縮合多環芳香族基が、下記式(I)で表される縮合多環芳香族化合物から、縮合芳香環に結合する水素原子を除いた残基である、希土類錯体であって、
[式(I)中、R1及びR2は、水素原子、又は、互いに結合して1個の芳香環、若しくは2個以上の芳香環を含む縮合芳香環を形成している基を示し、式(I)で表される縮合多環芳香族化合物の縮合芳香環が置換基を有していてもよい。]
前記縮合多環芳香族基を有する配位子が、下記式(10)で表されるホスフィンオキシド配位子であり、
[式(10)中、Zは前記縮合多環芳香族基を示し、R11及びR12はそれぞれ独立に前記縮合多環芳香族基とは異なるアリール基を示す。]
当該希土類錯体が、前記希土類イオンに配位結合し下記式(21)で表されるジケトン配位子を更に備える、希土類錯体。
[式(21)中、R 23 、R 24 及びR 25 はそれぞれ独立に、水素原子、アルキル基、ハロゲン化アルキル基、前記縮合多環芳香族基とは異なるアリール基、又はヘテロアリール基を示す。] - 希土類イオンと、該希土類イオンに配位結合し縮合多環芳香族基を有する配位子と、を備え、
前記縮合多環芳香族基が、下記式(I)で表される縮合多環芳香族化合物から、縮合芳香環に結合する水素原子を除いた残基である、希土類錯体であって、
[式(I)中、R1及びR2は、水素原子、又は、互いに結合して1個の芳香環、若しくは2個以上の芳香環を含む縮合芳香環を形成している基を示し、式(I)で表される縮合多環芳香族化合物の縮合芳香環が置換基を有していてもよい。]
当該希土類錯体が2個以上の前記希土類イオンを備え、
前記縮合多環芳香族基を有する配位子が、下記式(30)で表される二座のホスフィンオキシド配位子であり、該ホスフィンオキシド配位子が2個の前記希土類イオンに配位結合している、希土類錯体。
[式(30)中、Zは前記縮合多環芳香族基を示し、R 11 及びR 12 はそれぞれ独立に前記縮合多環芳香族基とは異なるアリール基を示す。] - 当該希土類錯体が、前記式(30)で表される二座のホスフィンオキシド配位子及び前記希土類イオンが交互に連結されることにより繰り返し構造を形成している、請求項2に記載の希土類錯体。
- 請求項1~4のいずれか一項に記載の希土類錯体を含有する、発光材料。
- 請求項5に記載の発光材料を含む、発光体。
- 請求項6に記載の発光体を備える、発光デバイス。
- 請求項1~4のいずれか一項に記載の希土類錯体を含む発光層を有する、合わせガラス用中間膜。
- 対向する2枚のガラス板と、
それらの間に配置された請求項8に記載の合わせガラス用中間膜と、
を備える、合わせガラス。 - 請求項9に記載の合わせガラスを有する、車両用フロントガラス。
- 請求項1~4のいずれか一項に記載の希土類錯体を含む、波長変換材料。
- 請求項1~4のいずれか一項に記載の希土類錯体を含む、セキュリティ材料。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2018130925 | 2018-07-10 | ||
JP2018130925 | 2018-07-10 | ||
PCT/JP2019/026751 WO2020013087A1 (ja) | 2018-07-10 | 2019-07-04 | 希土類錯体、発光材料、発光体、発光デバイス、合わせガラス用中間膜、合わせガラス、車両用フロントガラス、波長変換材料及びセキュリティ材料 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPWO2020013087A1 JPWO2020013087A1 (ja) | 2021-08-19 |
JP7317376B2 true JP7317376B2 (ja) | 2023-07-31 |
Family
ID=69142428
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2020530150A Active JP7317376B2 (ja) | 2018-07-10 | 2019-07-04 | 希土類錯体、発光材料、発光体、発光デバイス、合わせガラス用中間膜、合わせガラス、車両用フロントガラス、波長変換材料及びセキュリティ材料 |
Country Status (5)
Country | Link |
---|---|
US (1) | US20210269460A1 (ja) |
EP (1) | EP3822277A4 (ja) |
JP (1) | JP7317376B2 (ja) |
CN (1) | CN112384518B (ja) |
WO (1) | WO2020013087A1 (ja) |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002124383A (ja) | 2000-10-17 | 2002-04-26 | Konica Corp | エレクトロルミネッセンス素子および色変換フィルター |
CN1687080A (zh) | 2005-04-14 | 2005-10-26 | 复旦大学 | 芳香基取代双膦双氧化物螯合稀土配合物及其合成方法 |
JP2007269780A (ja) | 2006-03-08 | 2007-10-18 | Nissan Chem Ind Ltd | ホスホン酸−ジケトン複合系希土類金属錯体 |
JP2008159604A (ja) | 2006-12-20 | 2008-07-10 | Toshiba Corp | 蛍光性錯体を用いた有機エレクトロルミネッセンス素子および表示システム |
WO2012150712A1 (ja) | 2011-05-02 | 2012-11-08 | 国立大学法人北海道大学 | 希土類錯体ポリマー及びプラスチック成形体 |
CN103320117A (zh) | 2013-04-12 | 2013-09-25 | 中国工程物理研究院化工材料研究所 | 浓度、温度传感材料 |
JP2016166139A (ja) | 2015-03-09 | 2016-09-15 | 国立大学法人北海道大学 | 希土類錯体及び発光素子 |
WO2018155557A1 (ja) | 2017-02-27 | 2018-08-30 | 国立大学法人北海道大学 | 希土類錯体及び発光素子 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2005008872A (ja) * | 2003-05-22 | 2005-01-13 | Mitsubishi Chemicals Corp | 発光装置及び蛍光体 |
WO2015115530A1 (ja) * | 2014-01-31 | 2015-08-06 | 出光興産株式会社 | 化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子及び電子機器 |
CN105431441B (zh) * | 2014-01-31 | 2019-03-12 | 出光兴产株式会社 | 化合物、有机电致发光元件用材料、有机电致发光元件和电子设备 |
-
2019
- 2019-07-04 US US17/258,320 patent/US20210269460A1/en active Pending
- 2019-07-04 WO PCT/JP2019/026751 patent/WO2020013087A1/ja active Search and Examination
- 2019-07-04 JP JP2020530150A patent/JP7317376B2/ja active Active
- 2019-07-04 EP EP19835116.5A patent/EP3822277A4/en active Pending
- 2019-07-04 CN CN201980045748.4A patent/CN112384518B/zh active Active
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002124383A (ja) | 2000-10-17 | 2002-04-26 | Konica Corp | エレクトロルミネッセンス素子および色変換フィルター |
CN1687080A (zh) | 2005-04-14 | 2005-10-26 | 复旦大学 | 芳香基取代双膦双氧化物螯合稀土配合物及其合成方法 |
JP2007269780A (ja) | 2006-03-08 | 2007-10-18 | Nissan Chem Ind Ltd | ホスホン酸−ジケトン複合系希土類金属錯体 |
JP2008159604A (ja) | 2006-12-20 | 2008-07-10 | Toshiba Corp | 蛍光性錯体を用いた有機エレクトロルミネッセンス素子および表示システム |
WO2012150712A1 (ja) | 2011-05-02 | 2012-11-08 | 国立大学法人北海道大学 | 希土類錯体ポリマー及びプラスチック成形体 |
CN103320117A (zh) | 2013-04-12 | 2013-09-25 | 中国工程物理研究院化工材料研究所 | 浓度、温度传感材料 |
JP2016166139A (ja) | 2015-03-09 | 2016-09-15 | 国立大学法人北海道大学 | 希土類錯体及び発光素子 |
WO2018155557A1 (ja) | 2017-02-27 | 2018-08-30 | 国立大学法人北海道大学 | 希土類錯体及び発光素子 |
Non-Patent Citations (4)
Title |
---|
KITAGAWA,Y. et al.,A highly luminescent Eu(III) complex based on an electronically isolated aromatic ring system with u,Dalton Transactions,2018年05月17日,Vol.47, No.21,p.7327-7332,ISSN 1477-9226 |
KITAGAWA,Y. et al.,Visible luminescent lanthanide ions and a large π-conjugated ligand system shake hands,Physical Chemistry Chemical Physics,2016年,Vol.18, No.45,p.31012-31016,ISSN 1463-9076 |
OSAWA,M. et al.,Intra-Complex Energy Transfer of Europium(III) Complexes Containing Anthracene and Phenanthrene Moie,Journal of Physical Chemistry A,2009年,Vol.113, No.41,p.10895-10902,ISSN 1089-5639 |
STEEMERS,F.J. et al.,Water-Soluble Neutral Calix[4]arene-Lanthanide Complexes; Synthesis and Luminescence Properties,Journal of Organic Chemistry,1997年,Vol.62, No.13,p.4229-4235,ISSN 0022-3263 |
Also Published As
Publication number | Publication date |
---|---|
CN112384518B (zh) | 2023-10-20 |
EP3822277A1 (en) | 2021-05-19 |
JPWO2020013087A1 (ja) | 2021-08-19 |
CN112384518A (zh) | 2021-02-19 |
EP3822277A4 (en) | 2022-03-16 |
WO2020013087A1 (ja) | 2020-01-16 |
US20210269460A1 (en) | 2021-09-02 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN105061514B (zh) | 有机金属配合物和发光元件,发光装置和电子装置 | |
JP4299144B2 (ja) | フッ素化フェニルピリジン、フェニルピリミジン、およびフェニルキノリンを含むエレクトロルミネッセンスイリジウム化合物ならびにこのような化合物を用いて製造されるデバイス | |
JP5538644B2 (ja) | 有機金属錯体、有機金属錯体を用いた発光素子、発光装置および電子機器 | |
JP6765107B2 (ja) | イリジウム錯体の製造方法、イリジウム錯体ならびに該化合物からなる発光材料 | |
JP5911377B2 (ja) | 有機化合物およびこれを有する有機発光素子 | |
TW201006911A (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
JP2009114137A (ja) | 有機金属錯体及びこれを用いた有機発光素子並びに表示装置 | |
KR101252603B1 (ko) | 엔-메틸이미다졸릴트리아졸 보조 리간드를 이용한 짙은 청색 인광 이리듐 착화합물 | |
CN110337441B (zh) | 稀土络合物和发光元件 | |
JP5294242B2 (ja) | 金属配位化合物ならびにこれを用いた発光材料 | |
JP7317376B2 (ja) | 希土類錯体、発光材料、発光体、発光デバイス、合わせガラス用中間膜、合わせガラス、車両用フロントガラス、波長変換材料及びセキュリティ材料 | |
TW201113255A (en) | Material selecting method upon purifying iridium complex by sublimation | |
JP7274134B2 (ja) | 希土類化合物、発光体、発光デバイス、波長変換材料及びセキュリティ材料 | |
WO2021132373A1 (ja) | 希土類錯体 | |
JP4296995B2 (ja) | フルオレン化合物およびその製造方法 | |
WO2020137638A1 (ja) | 希土類化合物、ホスフィンオキシド化合物及び発光体 | |
JP7072261B2 (ja) | ホスフィンオキシド化合物、希土類錯体及び発光材料 | |
JP3777428B2 (ja) | シリルエチニル基を有するトリフェニレン化合物及びその製造方法 | |
JP7083995B2 (ja) | フェニルトリアゾール金属錯体及び発光素子 | |
JP5765764B2 (ja) | 金属錯体、発光素子、表示装置 | |
Tan et al. | Synthesis and Photophysical Properties of Charged Iridium (III) Cyclometallates Based on Hole-transporting Carbazole Unit |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A529 | Written submission of copy of amendment under article 34 pct |
Free format text: JAPANESE INTERMEDIATE CODE: A5211 Effective date: 20201225 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20201225 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20220106 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20230214 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20230414 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20230704 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20230711 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 7317376 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |