JP6917596B2 - 希土類錯体ポリマー - Google Patents
希土類錯体ポリマー Download PDFInfo
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- JP6917596B2 JP6917596B2 JP2018515708A JP2018515708A JP6917596B2 JP 6917596 B2 JP6917596 B2 JP 6917596B2 JP 2018515708 A JP2018515708 A JP 2018515708A JP 2018515708 A JP2018515708 A JP 2018515708A JP 6917596 B2 JP6917596 B2 JP 6917596B2
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- 229920000642 polymer Polymers 0.000 title claims description 122
- 229910052761 rare earth metal Inorganic materials 0.000 title claims description 112
- 150000002910 rare earth metals Chemical class 0.000 title claims description 60
- -1 rare earth ion Chemical class 0.000 claims description 48
- 239000003446 ligand Substances 0.000 claims description 34
- 150000002500 ions Chemical class 0.000 claims description 25
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000005594 diketone group Chemical group 0.000 claims description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229910052805 deuterium Inorganic materials 0.000 claims description 2
- 125000004431 deuterium atom Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 230000005284 excitation Effects 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 238000000295 emission spectrum Methods 0.000 description 18
- 238000004020 luminiscence type Methods 0.000 description 14
- 229910052693 Europium Inorganic materials 0.000 description 13
- 229910052771 Terbium Inorganic materials 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
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- 125000000962 organic group Chemical group 0.000 description 6
- GRTJBNJOHNTQBO-UHFFFAOYSA-N [2-(2-diphenylphosphanylphenyl)phenyl]-diphenylphosphane Chemical compound C1=CC=CC=C1P(C=1C(=CC=CC=1)C=1C(=CC=CC=1)P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 GRTJBNJOHNTQBO-UHFFFAOYSA-N 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
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- 150000002909 rare earth metal compounds Chemical class 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
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- IMKLRZRHCYOOFN-UHFFFAOYSA-N 2,5-bis(diphenylphosphoryl)furan Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C(O1)=CC=C1P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 IMKLRZRHCYOOFN-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
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- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 230000002165 photosensitisation Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- GKWLILHTTGWKLQ-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical compound O1CCOC2=CSC=C21 GKWLILHTTGWKLQ-UHFFFAOYSA-N 0.000 description 1
- HXQGFYGHQWPWMF-UHFFFAOYSA-N 2,5-bis(diphenylphosphoryl)-5-phenylcyclohexa-1,3-diene Chemical group C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C(C=C1)=CCC1(P(=O)(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 HXQGFYGHQWPWMF-UHFFFAOYSA-N 0.000 description 1
- LACYYWKMIJOHLU-UHFFFAOYSA-N 2,5-dibromofuran Chemical compound BrC1=CC=C(Br)O1 LACYYWKMIJOHLU-UHFFFAOYSA-N 0.000 description 1
- KYYIRCLYNDIEHT-UHFFFAOYSA-N O=P(c1ccc(P(c2ccccc2)(c2ccccc2)=O)[s]1)(c1ccccc1)c1ccccc1 Chemical compound O=P(c1ccc(P(c2ccccc2)(c2ccccc2)=O)[s]1)(c1ccccc1)c1ccccc1 KYYIRCLYNDIEHT-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 229930182556 Polyacetal Natural products 0.000 description 1
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 238000000071 blow moulding Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- XGRJZXREYAXTGV-UHFFFAOYSA-N chlorodiphenylphosphine Chemical compound C=1C=CC=CC=1P(Cl)C1=CC=CC=C1 XGRJZXREYAXTGV-UHFFFAOYSA-N 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
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- 238000000748 compression moulding Methods 0.000 description 1
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- 229910052751 metal Inorganic materials 0.000 description 1
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- 239000012046 mixed solvent Substances 0.000 description 1
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- 239000013110 organic ligand Substances 0.000 description 1
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- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
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- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
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- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
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- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
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- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C49/92—Ketonic chelates
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/65515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring
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- C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
- C08G79/02—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing phosphorus
- C08G79/04—Phosphorus linked to oxygen or to oxygen and carbon
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- C08G79/14—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing two or more elements other than carbon, oxygen, nitrogen, sulfur and silicon
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- C07F9/02—Phosphorus compounds
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Description
本実施形態の希土類錯体ポリマーは、三価の希土類イオンと、式(1)で表されるホスフィンオキシド二座配位子と、を含む。
フラスコに0.65gのEu(hfa)3(H2O)2、0.37gのdpf及び80mLのメタノールを加えた。この溶液を60℃で攪拌しながら、3時間加熱還流した。その後、反応液中の沈殿物を分離し、これを洗浄することで目的とする希土類錯体ポリマーの粉末を得た。
Eu(hfa)3(H2O)2の代わりにGd(hfa)3(H2O)2を用いたこと以外は、作製例1と同様の方法により希土類錯体ポリマーの粉末を得た。
Eu(hfa)3(H2O)2の代わりにTb(hfa)3(H2O)2を用いたこと以外は、作製例1と同様の方法により希土類錯体ポリマーの粉末を得た。
Eu(hfa)3(H2O)2の代わりにTb(hfa)3(H2O)2及びEu(hfa)3(H2O)2を1:1、10:1又は99:1のモル比で用いたこと以外は、作製例1と同様の方法により希土類錯体ポリマーの粉末を得た。
[Eu(hfa)3(dpf)]nポリマー、下記式で表されるチオフェン配位子(dpt)を有する[Eu(hfa)3(dpt)]nポリマー、下記式で表されるEDOT配位子(dpedot)を有する[Eu(hfa)3(dpedot)]nポリマーについて、応力刺激による発光(応力発光)の強度を測定した。
[Eu(hfa)3(dpf)]nポリマー、及び[Eu(hfa)3(dpedot)]nポリマーについて有機溶媒に対する溶解性を評価した。溶解性は、希土類錯体ポリマー30mg及びメタノール2mLをガラス容器中で攪拌し、混合液の状態を観察する試験によって評価した。
[Eu(hfa)3(dpf)]nポリマー、[Gd(hfa)3(dpf)]nポリマー及び[Tb(hfa)3(dpf)]nポリマーの粉末に対し、380nmの波長の励起光を照射し、希土類錯体ポリマーからの発光を測定した。UV励起による発光特性の測定装置として、HORIBA Fluorolog−3 spectrofluorometerを用いた。図1は、各希土類錯体ポリマーの発光スペクトルである。
EuとTbの比率(モル比、Eu:Tb)が100:0、1:1、1:99、又は0:100の希土類錯体ポリマーの粉末を用いて応力発光を測定した。図2は、各希土類錯体ポリマーの発光スペクトルを示す。
[Eu(hfa)3(dpf)]nポリマー、及び[Tb,Eu(hfa)3(dpf)]nポリマー(Tb/Eu=1又は10)の粉末に対し、380nmの波長の励起光の照射又は応力刺激を与え、ポリマーからの発光を測定した。図3の(a)は励起光の照射により得られた発光スペクトルを示し、図3の(b)は応力刺激により得られた発光スペクトルを示す。
[Tb,Eu(hfa)3(dpf)]nポリマー(Tb/Eu=10)の粉末に対し、380nmの波長の励起光を照射して、温度条件の違いによる発光色を測定した。温度条件は、100K、200K、300K、又は400Kとした。図4は、各温度条件におけるポリマーの発光スペクトルを示す。
1,4−ビス(ジフェニルホスホリル)ビフェニル(dpbp)により架橋された[Tb,Eu(hfa)3(dpbp)]nポリマー(Tb/Eu=150)、及び[Tb,Eu(hfa)3(dpf)]nポリマー(Tb/Eu=10)の粉末に対し、350nm、375nm、400nm、又は425nmの波長の励起光を照射し、ポリマーからの発光を測定した。図5の(a)はEu(hfa)3(dpbp)]nポリマー(Tb/Eu=150)の発光スペクトルを示し、図5の(b)は[Tb,Eu(hfa)3(dpf)]nポリマー(Tb/Eu=10)の発光スペクトルを示す。
Claims (4)
- 2種以上の前記希土類イオンを含む、請求項1に記載の希土類錯体ポリマー。
- 前記希土類イオンが、Eu(III)イオン、Tb(III)イオン、Gd(III)イオン、Sm(III)イオン、Yb(III)イオン、Nd(III)イオン、Er(III)イオン、Y(III)イオン、Dy(III)イオン、Ce(III)イオン、及びPr(III)イオンからなる群から選択される少なくとも一種の希土類イオンである、請求項1又は2に記載の希土類錯体ポリマー。
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