JP5967663B2 - 白金錯体 - Google Patents
白金錯体 Download PDFInfo
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- JP5967663B2 JP5967663B2 JP2013532466A JP2013532466A JP5967663B2 JP 5967663 B2 JP5967663 B2 JP 5967663B2 JP 2013532466 A JP2013532466 A JP 2013532466A JP 2013532466 A JP2013532466 A JP 2013532466A JP 5967663 B2 JP5967663 B2 JP 5967663B2
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 title claims description 216
- 229910052697 platinum Inorganic materials 0.000 title claims description 106
- 239000003446 ligand Substances 0.000 claims description 118
- 229920006395 saturated elastomer Polymers 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 239000000463 material Substances 0.000 claims description 23
- -1 R 26 Chemical compound 0.000 claims description 22
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 22
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 22
- 125000003342 alkenyl group Chemical group 0.000 claims description 21
- 125000000623 heterocyclic group Chemical group 0.000 claims description 21
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
- 125000003282 alkyl amino group Chemical group 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 7
- 230000017105 transposition Effects 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 105
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 69
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 238000004770 highest occupied molecular orbital Methods 0.000 description 31
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 16
- 125000001072 heteroaryl group Chemical group 0.000 description 15
- 238000004519 manufacturing process Methods 0.000 description 15
- 238000005481 NMR spectroscopy Methods 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- 125000004429 atom Chemical group 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 239000013078 crystal Substances 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000003480 eluent Substances 0.000 description 8
- 229940100684 pentylamine Drugs 0.000 description 8
- 238000006862 quantum yield reaction Methods 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 230000014509 gene expression Effects 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000012046 mixed solvent Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 125000004430 oxygen atom Chemical group O* 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- 125000004434 sulfur atom Chemical group 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 125000005330 8 membered heterocyclic group Chemical group 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 125000002950 monocyclic group Chemical group 0.000 description 5
- WZUODJNEIXSNEU-UHFFFAOYSA-N 2-Hydroxy-4-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(O)=C1 WZUODJNEIXSNEU-UHFFFAOYSA-N 0.000 description 4
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 4
- FZHSPPYCNDYIKD-UHFFFAOYSA-N 5-methoxysalicylaldehyde Chemical compound COC1=CC=C(O)C(C=O)=C1 FZHSPPYCNDYIKD-UHFFFAOYSA-N 0.000 description 4
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000003775 Density Functional Theory Methods 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 150000003057 platinum Chemical class 0.000 description 4
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 3
- 0 CCCCC*=Cc1ccccc1 Chemical compound CCCCC*=Cc1ccccc1 0.000 description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- 238000004364 calculation method Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000004776 molecular orbital Methods 0.000 description 3
- 238000012856 packing Methods 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 150000003058 platinum compounds Chemical class 0.000 description 3
- 239000010453 quartz Substances 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 2
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 2
- ZSKGQVFRTSEPJT-UHFFFAOYSA-N pyrrole-2-carboxaldehyde Chemical compound O=CC1=CC=CN1 ZSKGQVFRTSEPJT-UHFFFAOYSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 238000002424 x-ray crystallography Methods 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- AAQTWLBJPNLKHT-UHFFFAOYSA-N 1H-perimidine Chemical compound N1C=NC2=CC=CC3=CC=CC1=C32 AAQTWLBJPNLKHT-UHFFFAOYSA-N 0.000 description 1
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
- JFJNVIPVOCESGZ-UHFFFAOYSA-N 2,3-dipyridin-2-ylpyridine Chemical compound N1=CC=CC=C1C1=CC=CN=C1C1=CC=CC=N1 JFJNVIPVOCESGZ-UHFFFAOYSA-N 0.000 description 1
- VEUMANXWQDHAJV-UHFFFAOYSA-N 2-[2-[(2-hydroxyphenyl)methylideneamino]ethyliminomethyl]phenol Chemical compound OC1=CC=CC=C1C=NCCN=CC1=CC=CC=C1O VEUMANXWQDHAJV-UHFFFAOYSA-N 0.000 description 1
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- ILEIUTCVWLYZOM-UHFFFAOYSA-N 2-hydroxy-5-methylbenzaldehyde Chemical compound CC1=CC=C(O)C(C=O)=C1 ILEIUTCVWLYZOM-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- WMPDAIZRQDCGFH-UHFFFAOYSA-N 3-methoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 description 1
- 125000006042 4-hexenyl group Chemical group 0.000 description 1
- FDUBQNUDZOGOFE-UHFFFAOYSA-N 5-fluoro-2-hydroxybenzaldehyde Chemical compound OC1=CC=C(F)C=C1C=O FDUBQNUDZOGOFE-UHFFFAOYSA-N 0.000 description 1
- 125000006043 5-hexenyl group Chemical group 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- 125000006314 C5-C8 alkoxy group Chemical group 0.000 description 1
- PZRUSKYEJBBWQY-GXDHUFHOSA-N CCCCC/N=C/c(cc(cc1)OC)c1O Chemical compound CCCCC/N=C/c(cc(cc1)OC)c1O PZRUSKYEJBBWQY-GXDHUFHOSA-N 0.000 description 1
- 102100026816 DNA-dependent metalloprotease SPRTN Human genes 0.000 description 1
- 101710175461 DNA-dependent metalloprotease SPRTN Proteins 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 238000011000 absolute method Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000005266 diarylamine group Chemical group 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000005935 hexyloxycarbonyl group Chemical group 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229940030980 inova Drugs 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004998 naphthylethyl group Chemical group C1(=CC=CC2=CC=CC=C12)CC* 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
- XDJOIMJURHQYDW-UHFFFAOYSA-N phenalene Chemical compound C1=CC(CC=C2)=C3C2=CC=CC3=C1 XDJOIMJURHQYDW-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 125000004346 phenylpentyl group Chemical group C1(=CC=CC=C1)CCCCC* 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 238000001338 self-assembly Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
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Description
四座配位子が白金に配位し、前記四座配位子が、架橋により連結された2つの二座配位子を有し、前記2つの二座配位子が、それぞれイミノ部位を有し、前記イミノ部位の窒素原子は互いにトランス位で白金に配位し、前記2つの二座配位子が、互いに構造が異なる第2の白金錯体のいずれかの白金錯体である。
四座配位子が白金に配位し、前記四座配位子が、架橋により連結された2つの二座配位子を有し、前記2つの二座配位子が、それぞれイミノ部位を有し、前記イミノ部位の窒素原子は互いにトランス位で白金に配位し、前記2つの二座配位子が、互いに構造が異なる第2の白金錯体である。
四座配位子が白金に配位し、前記四座配位子が、架橋により連結された2つの二座配位子を有し、前記2つの二座配位子が、それぞれイミノ部位を有し、前記イミノ部位の窒素原子は互いにトランス位で白金に配位し、前記2つの二座配位子が、互いに構造が異なる第2の白金錯体を含む発光材料である。
Xは、aおよびbで印を付けた原子と共に、X’は、cおよびdで印をつけた原子と共に、またはX’’は、eおよびfで印をつけた原子と共に、1つのベンゼン環、1つの複素芳香族環、1つ以上のベンゼン環が縮合した芳香族縮合環、1つ以上の複素芳香族環が縮合した複素芳香族縮合環、1つ以上のベンゼン環と1つ以上の複素芳香族環が縮合した混合縮合多環を形成し、前記環は、置換基を1以上有してもよく、
R11、R21、R31およびR41は、アルキル基、アルケニル基、アリール基、アラルキル基、シクロアルキル基、飽和もしくは不飽和な複素環基、および飽和もしくは不飽和な複素環アルキル基からなる群から選択され、
R12、R22、R32およびR42は、水素原子、アルキル基、アルケニル基、アリール基、アラルキル基、シクロアルキル基、飽和もしくは不飽和な複素環基、および飽和もしくは不飽和な複素環アルキル基からなる群から選択され、
R43およびR44は、水素原子、アルキル基、アルケニル基、アルコキシ基、ハロゲン原子、アリール基、アラルキル基、シクロアルキル基、ヒドロキシ基、アミノ基、アルキルアミノ基、ニトロ基、スルホニル基、スルフィニル基、カルボキシ基、アルコキシカルボニル基、シアノ基、飽和もしくは不飽和な複素環基、および飽和もしくは不飽和な複素環アルキル基からなる群から独立して選択される。
R11、R21、R31およびR41は、アルキル基、アルケニル基、アリール基、アラルキル基、シクロアルキル基、飽和もしくは不飽和な複素環基、および飽和もしくは不飽和な複素環アルキル基からなる群から選択され、
R12、R22、R32およびR42は、水素原子、アルキル基、アルケニル基、アリール基、アラルキル基、シクロアルキル基、飽和もしくは不飽和な複素環基、および飽和もしくは不飽和な複素環アルキル基からなる群から選択され、
R13、R14、R15、R16、R23、R24、R25、R26、R33、R34、R35、R43およびR44は、水素原子、アルキル基、アルケニル基、アルコキシ基、ハロゲン原子、アリール基、アラルキル基、シクロアルキル基、ヒドロキシ基、アミノ基、アルキルアミノ基、ニトロ基、スルホニル基、スルフィニル基、カルボキシ基、アルコキシカルボニル基、シアノ基、飽和もしくは不飽和な複素環基、および飽和もしくは不飽和な複素環アルキル基からなる群から独立して選択される。
Xは、aおよびbで印を付けた原子と共に、X'は、cおよびdで印をつけた原子と共に、またはX''は、eおよびfで印をつけた原子と共に、1つのベンゼン環、1つの複素芳香族環、1つ以上のベンゼン環が縮合した芳香族縮合環、1つ以上の複素芳香族環が縮合した複素芳香族縮合環、1つ以上のベンゼン環と1つ以上の複素芳香族環が縮合した混合縮合多環を形成し、前記環は、置換基を1以上有してもよく、
R12、R22、R32およびR42は、水素原子、アルキル基、アルケニル基、アリール基、アラルキル基、シクロアルキル基、飽和もしくは不飽和な複素環基、および飽和もしくは不飽和な複素環アルキル基からなる群から選択され、
R43およびR44は、水素原子、アルキル基、アルケニル基、アルコキシ基、ハロゲン原子、アリール基、アラルキル基、シクロアルキル基、ヒドロキシ基、アミノ基、アルキルアミノ基、ニトロ基、スルホニル基、スルフィニル基、カルボキシ基、アルコキシカルボニル基、シアノ基、飽和もしくは不飽和な複素環基、および飽和もしくは不飽和な複素環アルキル基からなる群から独立して選択され、
Zは、式−(CH2)k−で表される基(式中、kは、7〜20の整数である)、式−(CH2)L−Y−(CH2)M−で表される基(式中、−Y−は、−COO−、−OCO−、−CO−、−NH−、−NR−、−O−であり、前記Rは、アルキル基であり、Lは、2〜6の整数であり、Mは、2〜6の整数である。)、または式−(CH2)2−(OCH2CH2)Q−で表される基(式中、Qは、2〜6の整数である。)である。
R12、R22、R32およびR42は、水素原子、アルキル基、アルケニル基、アリール基、アラルキル基、シクロアルキル基、飽和もしくは不飽和な複素環基、および飽和もしくは不飽和な複素環アルキル基からなる群から選択され、
R13、R14、R15、R16、R23、R24、R25、R26、R33、R34、R35、
R43およびR44は、水素原子、アルキル基、アルケニル基、アルコキシ基、ハロゲン原子、アリール基、アラルキル基、シクロアルキル基、ヒドロキシ基、アミノ基、アルキルアミノ基、ニトロ基、スルホニル基、スルフィニル基、カルボキシ基、アルコキシカルボニル基、シアノ基、飽和もしくは不飽和な複素環基、および飽和もしくは不飽和な複素環アルキル基からなる群から独立して選択され、
Zは、式−(CH2)k−で表される基(式中、kは、7〜20の整数である)、式−(CH2)L−Y−(CH2)M−で表される基(式中、−Y−は、−COO−、−OCO−、−CO−、−NH−、−NR−、−O−であり、前記Rは、アルキル基であり、Lは、2〜6の整数であり、Mは、2〜6の整数である。)、または式−(CH2)2−(OCH2CH2)Q−で表される基(式中、Qは、2〜6の整数である。)である。
核磁気共鳴(NMR)スペクトルはバリアン社製UNITY−INOVA核磁気共鳴装置(500MHz)を用いて測定し、測定溶媒の残存シグナルを内部基準として使用した。
DMF:ジメチルホルムアミド
THF:テトラヒドロフラン
DMSO:ジメチルスルホキシド
実施例1〜11で得た化合物(1)〜(11)について、296Kおよび77Kにおける固体発光量子収率φ(%)を測定した。具体的には、化合物(1)〜(11)の結晶状態(粉末)における発光量子収率を、絶対法によりそれぞれ求めた。測定方法は以下の通りである。
測定の際、酸素の影響を除くため、全てのサンプルは、石英セル中に結晶(化合物(1)〜(9))をそのまま封入して、アルゴン雰囲気下で測定した。さらに、低温(77K)での測定は、石英製デュワーを用いて、結晶を封入した上記石英セルを液体窒素で冷やしながら測定した。全ての発光スペクトルは、標準光源を利用することにより補正を行った。励起光として420nmまたは450nmの波長の光を用いた。内部量子収率の算出には、固体量子効率計算プログラム(日本分光株式会社製)を用いた。また、各発光性有機白金錯体が発する光の発光極大波長も、併せて測定した。測定結果を表1に示す。
実施例1の化合物(1)のHOMOとLUMOのエネルギー準位をDFT(密度汎関数理論)法により算出した。得られたHOMOとLUMOのエネルギー準位の分布を、図1Aに示す。図1Aに示すように、化合物(1)のHOMOは、サリチルアルミジン型配位子の寄与が大きく、LUMOは、イミノフェニル型配位子の寄与が大きいことが確認できた。すなわち、本発明の化合物のHOMOは、第2の二座配位子(イミノフェニル型配位子)と比べて第1の二座配位子(サリチルアルミジン型配位子)の寄与が大きく、LUMOは、第1の二座配位子(サリチルアルミジン型配位子)と比べて第2の二座配位子(イミノフェニル型配位子)の寄与が大きいことが確認できた。なお、化合物(1)の構造式を参考のため図1Bに示す。
実施例3の化合物(3)について、株式会社リガク社製イメージングプレート単結晶自動X線構造解析装置PAPID−AUTOを用いてX線結晶解析を行った。X線は、Mo−Ka線(λ=0.71075Å)を用いた。実施例3の化合物(3)は、酢酸エチルにより結晶化した結晶を用いた。結晶解析の結果、得られた結晶中におけるパッキングを図3に示す。
Claims (4)
- 2つの二座配位子が白金に配位し、前記2つの二座配位子が、それぞれイミノ部位を有し、前記イミノ部位の窒素原子は互いにトランス位で白金に配位し、前記2つの二座配位子が、互いに構造が異なり、
前記2つの二座配位子が、下記式(a1)と式(b1)、式(a1)と式(c1)、式(a1)と式(d1)、式(b1)と式(c1)、式(b1)と式(d1)および式(c1)と式(d1)の組み合わせから選択される白金錯体。
R11、R21、R31およびR41は、アルキル基、アルケニル基、アリール基、アラルキル基、シクロアルキル基、飽和もしくは不飽和な複素環基、および飽和もしくは不飽和な複素環アルキル基からなる群から選択され、
R12、R22、R32およびR42は、水素原子、アルキル基、アルケニル基、アリール基、アラルキル基、シクロアルキル基、飽和もしくは不飽和な複素環基、および飽和もしくは不飽和な複素環アルキル基からなる群から選択され、
R13、R14、R15、R16、R23、R24、R25、R26、R33、R34、R35、R43およびR44は、水素原子、アルキル基、アルケニル基、アルコキシ基、ハロゲン原子、アリール基、アラルキル基、シクロアルキル基、ヒドロキシ基、アミノ基、アルキルアミノ基、ニトロ基、スルホニル基、スルフィニル基、カルボキシ基、アルコキシカルボニル基、シアノ基、飽和もしくは不飽和な複素環基、および飽和もしくは不飽和な複素環アルキル基からなる群から独立して選択される。] - 四座配位子が白金に配位し、前記四座配位子が、架橋により連結された2つの二座配位子を有し、前記2つの二座配位子が、それぞれイミノ部位を有し、前記イミノ部位の窒素原子は互いにトランス位で白金に配位し、前記2つの二座配位子が、互いに構造が異なり、
以下の式(Ia)、式(IIa)、式(IIIa)、式(IVa)、式(Va)および式(VIa)からなる群から選択される構造で表される白金錯体。
R12、R22、R32およびR42は、水素原子、アルキル基、アルケニル基、アリール基、アラルキル基、シクロアルキル基、飽和もしくは不飽和な複素環基、および飽和もしくは不飽和な複素環アルキル基からなる群から選択され、
R13、R14、R15、R16、R23、R24、R25、R26、R33、R34、R35、R43およびR44は、水素原子、アルキル基、アルケニル基、アルコキシ基、ハロゲン原子、アリール基、アラルキル基、シクロアルキル基、ヒドロキシ基、アミノ基、アルキルアミノ基、ニトロ基、スルホニル基、スルフィニル基、カルボキシ基、アルコキシカルボニル基、シアノ基、飽和もしくは不飽和な複素環基、および飽和もしくは不飽和な複素環アルキル基からなる群から独立して選択され、
Zは、式−(CH2)k−で表される基(式中、kは、7〜20の整数である)、式−(CH2)L−Y−(CH2)M−で表される基(式中、−Y−は、−COO−、−OCO−、−CO−、−NH−、−NR−、−O−であり、前記Rは、アルキル基であり、Lは、2〜6の整数であり、Mは、2〜6の整数である。)、または式−(CH2)2−(OCH2CH2)Q−で表される基(式中、Qは、2〜6の整数である。)である。] - 請求項1〜3のいずれかに記載の白金錯体を含む発光材料。
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