WO2020134569A1 - 一种n^n^c^o型四齿铂(ii)配合物的制备及应用 - Google Patents
一种n^n^c^o型四齿铂(ii)配合物的制备及应用 Download PDFInfo
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- WO2020134569A1 WO2020134569A1 PCT/CN2019/115181 CN2019115181W WO2020134569A1 WO 2020134569 A1 WO2020134569 A1 WO 2020134569A1 CN 2019115181 W CN2019115181 W CN 2019115181W WO 2020134569 A1 WO2020134569 A1 WO 2020134569A1
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- atoms
- halogen
- groups
- substituted
- alkyl
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- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title abstract description 4
- 239000003446 ligand Substances 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 58
- 229910052736 halogen Inorganic materials 0.000 claims description 45
- 150000002367 halogens Chemical class 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- 229910052731 fluorine Inorganic materials 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 239000000463 material Substances 0.000 claims description 13
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims description 12
- 239000000758 substrate Substances 0.000 claims description 11
- -1 cyano, carboxy, styryl Chemical group 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000005266 diarylamine group Chemical group 0.000 claims description 5
- 125000004986 diarylamino group Chemical group 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 239000002243 precursor Substances 0.000 claims description 3
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 3
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 230000009471 action Effects 0.000 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 229910052805 deuterium Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- 239000002019 doping agent Substances 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 239000002904 solvent Substances 0.000 description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- 150000001875 compounds Chemical class 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000012074 organic phase Substances 0.000 description 16
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 14
- 238000000605 extraction Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 238000002390 rotary evaporation Methods 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 8
- 238000001819 mass spectrum Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- XAEBTCPOZVEMHR-UHFFFAOYSA-N 2-methylpropan-2-ol;potassium Chemical compound [K].CC(C)(C)O XAEBTCPOZVEMHR-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 4
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 3
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 3
- 229940125758 compound 15 Drugs 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 229940125810 compound 20 Drugs 0.000 description 3
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000013212 metal-organic material Substances 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 2
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 2
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- HJCUTNIGJHJGCF-UHFFFAOYSA-N 9,10-dihydroacridine Chemical compound C1=CC=C2CC3=CC=CC=C3NC2=C1 HJCUTNIGJHJGCF-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-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
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 125000004062 acenaphthenyl group Chemical group C1(CC2=CC=CC3=CC=CC1=C23)* 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 229940125773 compound 10 Drugs 0.000 description 2
- 229940126086 compound 21 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 238000002207 thermal evaporation Methods 0.000 description 2
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 1
- MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 description 1
- UVNPEUJXKZFWSJ-LMTQTHQJSA-N (R)-N-[(4S)-8-[6-amino-5-[(3,3-difluoro-2-oxo-1H-pyrrolo[2,3-b]pyridin-4-yl)sulfanyl]pyrazin-2-yl]-2-oxa-8-azaspiro[4.5]decan-4-yl]-2-methylpropane-2-sulfinamide Chemical compound CC(C)(C)[S@@](=O)N[C@@H]1COCC11CCN(CC1)c1cnc(Sc2ccnc3NC(=O)C(F)(F)c23)c(N)n1 UVNPEUJXKZFWSJ-LMTQTHQJSA-N 0.000 description 1
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 1
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- WDBQJSCPCGTAFG-QHCPKHFHSA-N 4,4-difluoro-N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclohexane-1-carboxamide Chemical compound FC1(CCC(CC1)C(=O)N[C@@H](CCN1CCC(CC1)N1C(=NN=C1C)C(C)C)C=1C=NC=CC=1)F WDBQJSCPCGTAFG-QHCPKHFHSA-N 0.000 description 1
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- LPDGERBTIAOGKS-UHFFFAOYSA-N CC(C)(C)c1cc(N(c2cccc(-c(cc(cc3)-c4c(C)cccc4C)c3O)c2)c2cccc(-c3cc(-c4c(C)cccc4C)ccn3)n2)cc(C(C)(C)C)c1 Chemical compound CC(C)(C)c1cc(N(c2cccc(-c(cc(cc3)-c4c(C)cccc4C)c3O)c2)c2cccc(-c3cc(-c4c(C)cccc4C)ccn3)n2)cc(C(C)(C)C)c1 LPDGERBTIAOGKS-UHFFFAOYSA-N 0.000 description 1
- GSTDTQDSAZRMSH-UHFFFAOYSA-N CC(C)(C)c1cc(N(c2cccc(-c3cc(-c4c(C)cccc4C)ccc3OC)c2)c2cccc(-c3cc(-c4c(C)cccc4C)ccn3)n2)cc(C(C)(C)C)c1 Chemical compound CC(C)(C)c1cc(N(c2cccc(-c3cc(-c4c(C)cccc4C)ccc3OC)c2)c2cccc(-c3cc(-c4c(C)cccc4C)ccn3)n2)cc(C(C)(C)C)c1 GSTDTQDSAZRMSH-UHFFFAOYSA-N 0.000 description 1
- PVFYFZCEMCZHOU-UHFFFAOYSA-N CC(C)(C)c1cc(Nc2cc(-c(cc(cc3)-c4c(C)cccc4C)c3OC)ccc2)cc(C(C)(C)C)c1 Chemical compound CC(C)(C)c1cc(Nc2cc(-c(cc(cc3)-c4c(C)cccc4C)c3OC)ccc2)cc(C(C)(C)C)c1 PVFYFZCEMCZHOU-UHFFFAOYSA-N 0.000 description 1
- HBYYIHAUVKRKOM-AATRIKPKSA-N CC/C=C(\C=C)/Br Chemical compound CC/C=C(\C=C)/Br HBYYIHAUVKRKOM-AATRIKPKSA-N 0.000 description 1
- QEOSFBKMMPRQKV-UHFFFAOYSA-N Cc(cccc1C)c1-c1ccnc(-c2nc(Br)ccc2)c1 Chemical compound Cc(cccc1C)c1-c1ccnc(-c2nc(Br)ccc2)c1 QEOSFBKMMPRQKV-UHFFFAOYSA-N 0.000 description 1
- ZFIZAZPUOYZQMD-UHFFFAOYSA-N Cc1cccc(C)c1-c(cc1)cc(-c2cc(N)ccc2)c1OC Chemical compound Cc1cccc(C)c1-c(cc1)cc(-c2cc(N)ccc2)c1OC ZFIZAZPUOYZQMD-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229940126657 Compound 17 Drugs 0.000 description 1
- 101000687716 Drosophila melanogaster SWI/SNF-related matrix-associated actin-dependent regulator of chromatin subfamily A containing DEAD/H box 1 homolog Proteins 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- 101000687741 Mus musculus SWI/SNF-related matrix-associated actin-dependent regulator of chromatin subfamily A containing DEAD/H box 1 Proteins 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- GNMLZJPTKPGKHQ-UHFFFAOYSA-N [Sn].[In].[Sn]=O Chemical compound [Sn].[In].[Sn]=O GNMLZJPTKPGKHQ-UHFFFAOYSA-N 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940126543 compound 14 Drugs 0.000 description 1
- 229940126142 compound 16 Drugs 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 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
- 238000010586 diagram Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 230000005525 hole transport Effects 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
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- 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
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- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- 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
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Definitions
- the invention relates to a novel N ⁇ N ⁇ C ⁇ O tetradentate platinum (II) complex metal organic material, especially a phosphorescent doping material used for photon emission in the light emitting layer of an OLED light emitting device.
- II tetradentate platinum
- OLED Organic Light-Emitting Diode
- Platinum (II) is generally a four-coordinated site, and a metal-organic platinum (II) complex with a unique configuration can be formed by designing a tetradentate ligand.
- platinum (II) complexes are relatively slow, especially for the development of new platinum (II) complex phosphorescent luminescent materials, for the promotion of platinum ( II)
- the commercial application of the complex is particularly important. Summary of the invention
- novel N ⁇ N ⁇ C ⁇ O tetradentate platinum(II) complex metal organic material involved in the present invention has the structure shown in the following figure:
- R 1 -R 15 are independently selected from hydrogen, deuterium, sulfur, halogen, hydroxy, acyl, alkoxy, acyloxy, amino, nitro, acylamino, cyano, carboxy, styryl, aminocarbonyl, Carbamoyl, benzylcarbonyl, aryloxy, diarylamino, saturated alkyl containing 1-30 C atoms, unsaturated alkyl containing 1-20 C atoms, substituted with 5-30 C atoms Substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups containing 5 to 30 C atoms, or adjacent R 1 to R 15 are connected to each other through a covalent bond to form a ring.
- R 1 -R 15 are independently selected from the group consisting of hydrogen, halogen, amino, nitro, cyano, diarylamino, saturated alkyl containing 1-10 C atoms, coatings containing 5-20 C atoms Halogen or one or more C1-C4 alkyl substituted or unsubstituted aryl groups, containing 5 to 20 C atoms, halogen or one or more C1-C4 alkyl substituted or unsubstituted heteroaryl groups, or phase
- the ortho-R 1 -R 15 are connected to each other through a covalent bond to form a ring, and the halogen is F, Cl, Br.
- R 1 -R 15 0-3 of which are independently represented as diarylamine groups, contain 5-10 C atoms by halogen or 1 to 3 C1-C4 alkanes
- 0 to 3 groups are independently represented as diphenylamino, phenyl, pyridyl, and carbazolyl, and other groups are independently represented as Hydrogen, fluorine or saturated alkyl group with 1 to 4 C atoms.
- R 1 '-R 5' are independently selected from hydrogen, halogen, di-arylamino, saturated alkyl group containing 1-10 C atoms, containing 5 to 20 C atoms or one or more halogen C1- C4 alkyl substituted or unsubstituted aryl group containing 5-20 C atoms or by one or more halogen, C1-C4 alkyl substituted or unsubstituted heteroaryl or adjacent R 1 '-R 5' Connected to each other through a covalent bond to form a ring, the halogen is F, Cl, Br.
- R 1 ′-R 5 ′ are independently represented as diarylamine groups, containing 5-10 C atoms by halogen or 1 to 3 C1- C4 alkyl substituted or unsubstituted aryl, 5-10 C atoms substituted by halogen or 1 to 3 C1-C4 alkyl substituted or unsubstituted heteroaryl; other groups are independently expressed as Hydrogen, halogen or saturated alkyl group containing 1-8 C atoms, the halogen is F, Cl.
- R 1 ′-R 5 ′ among which 0-3 groups are independently represented as diphenylamino, C1-C4 alkyl substituted or unsubstituted phenyl, pyridyl, carbazine Zazolyl, other groups are independently represented as hydrogen, fluorine, saturated alkyl containing 1-4 C atoms.
- halogen alkyl, alkenyl, aryl, acyl, alkoxy, and heterocyclic aromatic systems or heterocyclic aromatic groups may have the following meanings:
- halogen or halo includes fluorine, chlorine, bromine and iodine, preferably F, Cl, Br, particularly preferably F or Cl, most preferably F.
- ring, aryl, and heteroaryl groups connected by a covalent bond include 5 to 30 carbon atoms, preferably 5 to 20 carbon atoms, more preferably 5 to 10 carbon atoms, and are fused by one aromatic ring or multiple Aryl group consisting of aromatic rings.
- Suitable aryl groups are, for example, phenyl, naphthyl, acenaphthenyl, acenaphthenyl, anthracenyl, fluorenyl, phenalenyl.
- the aryl group may be unsubstituted (ie, all carbon atoms that can be substituted carry hydrogen atoms) or substituted at one, more than one, or all substitutable positions of the aryl group.
- Suitable substituents are, for example, halogen, preferably F, Br or Cl; alkyl, preferably alkyl having 1-20, 1-10 or 1-8 carbon atoms, particularly preferably methyl, ethyl, isopropyl Group or tert-butyl group; aryl group, preferably re-substituted or unsubstituted C 5 , C 6 aryl group or fluorenyl group; heteroaryl group, preferably a heteroaryl group containing at least one nitrogen atom, particularly preferably pyridyl;
- the aryl group particularly particularly preferably carries a substituent selected from F and tert-butyl, preferably an aryl group which may be a given aryl group or optionally substituted by
- the unsaturated alkyl group having 1 to 20 C atoms is preferably an alkenyl group, more preferably an alkenyl group having a double bond, and particularly preferably an alkenyl group having a double bond and 1 to 8 carbon atoms.
- the above-mentioned alkyl group includes an alkyl group having 1 to 30 carbon atoms, preferably 1 to 10 carbon atoms, and preferably 1 to 4 carbon atoms.
- the alkyl group may be branched or linear, or cyclic, and may be interrupted by one or more heteroatoms, preferably N, O, or S.
- the alkyl group may be substituted with one or more halogens or the above-mentioned substituents regarding aryl groups.
- alkyl groups it is possible to carry one or more aryl groups, all of which are suitable for this purpose, alkyl groups are particularly preferably selected from methyl, ethyl, isopropyl, n-propyl, Isobutyl, n-butyl, tert-butyl, sec-butyl, isopentyl, cyclopropyl, cyclopentyl, cyclohexyl.
- acyl group is connected to the CO group with a single bond, such as an alkyl group as used herein.
- alkoxy group is directly connected to oxygen by a single bond, as used herein an alkyl group.
- the above heteroaryl group is understood to be related to an aromatic, C 3 -C 8 ring group, and also contains an oxygen or sulfur atom or 1-4 nitrogen atoms or a combination of an oxygen or sulfur atom and up to two nitrogen atoms , And their substituted and benzo and pyrido fused derivatives, for example, through one of the ring-forming carbon atoms, the heteroaryl group may be substituted by one or more of the substituents mentioned for aryl Replaced by.
- the heteroaryl group may be a five- or six-membered aromatic heterocyclic ring system carrying the above independent groups containing 0, 1, or 2 substituents.
- Typical examples of heteroaryl groups include, but are not limited to, unsubstituted furan, benzofuran, thiophene, benzothiophene, pyrrole, pyridine, indole, azole, benzoxazole, isoxazole, benzisoazole, thiazole, benzo Thiazole, isothiazole, imidazole, benzimidazole, pyrazole, indazole, tetrazole, quinoline, isoquinoline, pyridazine, pyrimidine, purine and pyrazine, furan, 1,2,3-diazole, 1, 2,3-thiadiazole, 1,2,4-thiadiazole, triazole, benzotriazole, pyridine, benzoxazole, diazole,
- the substituents are halo, hydroxy, cyano, OC 1-6 alkyl, C 1-6 alkyl, hydroxy C 1-6 alkyl, and amino-C 1-6 alkyl. Specific examples shown below include but are not limited to the following structures:
- the precursor of the above complex that is, the ligand, has the structural formula as follows:
- R 1- R 15 are independently selected from hydrogen, halogen, amino, nitro, cyano, diarylamino, saturated alkyl containing 1-10 C atoms, halogenated containing 5-20 C atoms or One or more C1-C4 alkyl-substituted or unsubstituted aryl groups, containing 5 to 20 C atoms, halogen-substituted or one or more C1-C4 alkyl-substituted or unsubstituted heteroaryl groups, or adjacent R 1- R 15 are connected to each other through a covalent bond to form a ring.
- R 1 '-R 5' are independently selected from hydrogen, halogen, di-arylamino, saturated alkyl group containing 1-10 C atoms, containing 5 to 20 C atoms or one or more halogen C1- C4 alkyl substituted or unsubstituted aryl group containing 5-20 C atoms or by one or more halogen, C1-C4 alkyl substituted or unsubstituted heteroaryl or adjacent R 1 '-R 5' Connected to each other through a covalent bond to form a ring, the halogen is F, Cl, Br.
- an OLED device of thermal deposition and solution treatment can be manufactured.
- the complex is applied as a layer in the device by thermal deposition.
- the complex is applied in the form of a layer in the device by spin coating.
- the complex is applied in the form of a layer in the device by inkjet printing.
- the device emits orange-red when current is applied.
- the organic metal complex in the present invention has high fluorescence quantum efficiency, good thermal stability and low quenching constant, and can produce orange-red light OLED devices with high luminous efficiency and low roll-off.
- FIG. 1 is a schematic structural diagram of an organic electroluminescent device of the present invention.
- the preparation method of the above complex includes the following steps:
- the initial substrates S1 and S2 are subjected to Buchwald–Hartwig coupling reaction to obtain substrate S3, and S3 and S4 are subjected to Buchwald–Hartwig coupling reaction to obtain substrate S5, and S5 is demethylated under the action of pyridine hydrochloride to obtain S6.
- S6 reacts with K 2 PtCl 4 to obtain the target product P.
- Synthesis of compound 8 take compound 7 27.53g (0.10mol), compound 2 26.92g (0.10mol), palladium acetate 450mg (0.02eq., 2mmol), triphenylphosphine 1.05g (0.04eq., 4mmol), tertiary 22.44 g (2.0 eq., 0.20 mol) of potassium butoxide was added to the flask, 250 mL of dioxane was added, and the mixture was heated and refluxed under nitrogen for 8 hours.
- Synthesis of compound 10 take compound 8 23.18g (50mmol), compound 9 14.56g (50mmol), palladium acetate 225mg (0.02eq., 1mmol), triphenylphosphine 0.53g (0.04eq., 2mmol), tert-butanol Potassium 11.22g (2.0eq., 0.10mol) was added to the flask, 200mL of dioxane was added, and the mixture was heated and refluxed under nitrogen for 8 hours.
- Synthesis of compound 13 Take compound 1 19.92g (0.10mol), compound 12 24.12g (0.10mol), palladium acetate 450mg (0.02eq., 2mmol), triphenylphosphine 1.05g (0.04eq., 4mmol), tertiary 22.44 g (2.0 eq., 0.20 mol) of potassium butoxide was added to the flask, 250 mL of dioxane was added, and the mixture was heated and refluxed under nitrogen for 8 hours.
- Synthesis of compound 18 take compound 17 30.34g (0.10mol), compound 2 26.92g (0.10mol), palladium acetate 450mg (0.02eq., 2mmol), triphenylphosphine 1.05g (0.04eq., 4mmol), tertiary 22.44 g (2.0 eq., 0.20 mol) of potassium butoxide was added to the flask, 300 mL of dioxane was added, and the mixture was heated at reflux under nitrogen for 8 hours.
- Synthesis of compound 20 take compound 18 25.58g (50mmol), compound 19 16.96g (50mmol), palladium acetate 225mg (0.02eq., 1mmol), triphenylphosphine 0.53g (0.04eq., 2mmol), tert-butanol Potassium 11.22g (2.0eq., 0.10mol) was added to the flask, 300mL of dioxane was added, and the reaction was heated at reflux under nitrogen for 8 hours.
- ITO/TAPC(60nm)/TCTA Pt(II)(40nm)/TmPyPb(30nm)/LiF(1nm)/Al(80nm)
- the transparent anodized tin indium tin oxide (ITO, 20) (10 ⁇ /sq) glass substrate 10 was ultrasonically cleaned using acetone, ethanol and distilled water in sequence, and then treated with oxygen plasma for 5 minutes.
- the ITO substrate is mounted on the substrate holder of the vacuum vapor deposition equipment.
- control the system pressure at 10 -6 torr.
- the hole transport layer (30) material TAPC with a thickness of 60 nm is evaporated onto the ITO substrate.
- the luminescence layer material (40) TCTA with a thickness of 40 nm is evaporated, in which platinum (II) complex dopants of different mass fractions are doped.
- the electron transport layer (50) material TmPyPb with a thickness of 30 nm is then evaporated.
- LiF with a thickness of 1 nm is evaporated as an electron injection layer (60).
- the structure and manufacturing method of the device are exactly the same, the difference is that the organometallic complexes P0, P1, P6, P24, and P45 are used sequentially as the dopant and doping concentration in the light-emitting layer.
- Pt0 is a classic O ⁇ N ⁇ N ⁇ O type red light material.
- the doping concentration of the tetradentate platinum(II) complex is 4wt%, 8wt% and 12wt%
- the above ITO/HTL-1(60nm)/EML-1:Pt(II)(40nm)/ETL- 1(30nm)/LiF(1nm)/Al(80nm) device basic structure to prepare the device.
- the start-up voltage V on of the four-tooth platinum (II) complexes P1, P6, P24, and P45 devices is reduced to varying degrees compared to Pt0 devices.
- the current efficiency (CE), power efficiency (PE) and external quantum efficiency (EQE) of the devices based on P1, P6, P24, P45 have different degrees compared to the devices based on Pt-0.
- the improvement, especially P45, is more obvious in current efficiency (CE), power efficiency (PE) and external quantum efficiency (EQE).
- the doping concentration of the tetradentate platinum (II) complex increases, the efficiency of P1, P6, P24, and P45 are improved to varying degrees.
- P45 has a larger steric hindrance group, which can effectively reduce the aggregation between molecules, avoid the formation of exciplex, and improve the luminous efficiency.
- the central platinum (II) is a six-membered ring + six-membered ring + five-membered ring chelating coordination mode
- the formed complex is stable
- the rigid structure is strong
- the energy Reducing the dissipation of non-radiative energy such as intramolecular rotation and vibration is conducive to the improvement of the luminous efficiency and performance of the platinum(II) complex.
- the triphenylamine structure in the ligand skeleton can be easily added with different substituents to facilitate the optimization and regulation of molecular structure.
- the performance of the organic electroluminescent device prepared by the present invention is better than that of the reference device, and the new N ⁇ N ⁇ C ⁇ O tetradentate platinum (II) complex metal organic material is involved Has greater application value.
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Abstract
Description
Claims (14)
- 根据权利要求1所述的配合物,其中R 1-R 15独立的选自氢、卤素、氨基、硝基、氰基、二芳胺基、含1-10个C原子的饱和烷基、含5-20个C原子的被卤素或一个或多个C1-C4烷基取代的或未取代芳基、含5-20个C原子的被卤素或一个或多个C1-C4烷基取代的或未取代杂芳基、或者相邻R 1-R 15相互通过共价键连接成环,所述卤素为F,Cl,Br。
- 根据权利要求2所述的配合物,其中R 1-R 15的15个基团中,其中有0-3个基团独立的表示为二芳胺基、含5-10个C原子被卤素或1至3个C1-C4烷基取代的或未取代的芳基、含5-10个C原子的被卤素或1至3个C1-C4烷基取代的或未取代的含N杂芳基;其它的基团独立的表示为氢或含1-8个C原子的饱和烷基,所述卤素为F,Cl。
- 根据权利要求3所述的配合物,其中所述R 1-R 15的15个基团中,其中有0-3个基团独立的表示为二苯胺基、苯基、吡啶基、咔唑基,其它基团独立的表示为氢、氟或者1-4个C原子的饱和烷基。
- 根据权利要求5所述的配合物,其中R 1’-R 5’的5个基团中,其中有0-3个基团独立的表示为二芳胺基、含5-10个C原子被卤素或1至3个C1-C4烷基取代的或未取代的芳基、含5-10个C原子的被卤素或1至3个C1-C4烷基取代的或未取代的杂芳基;其它的基团独立的表示为氢、卤素或含1-8个C原子的饱和烷基,所述卤素为F,Cl。
- 根据权利要求6所述的配合物,其中R 1’-R 5’的5个基团中,其中有0-3个基团独立的表示为二苯胺基、C1-C4烷基取代或未取代的苯基、吡啶基、咔唑基,其它基团独立的表示为氢、氟、含1-4个C原子的饱和烷基。
- 权利要求1-9任一所述配合物在OLED发光器件中的应用。
- 根据权利要求13所述的应用,所述权利要求1-9任一所述配合物为发光层中起光子发射作用的磷光掺杂材料。
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DE112019005247.0T DE112019005247B4 (de) | 2018-12-28 | 2019-11-02 | Herstellung und Anwendung eines tetradentaten Platin(II)-Komplexes vom Typ N^N^C^O |
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CN107056844A (zh) * | 2016-02-11 | 2017-08-18 | 三星电子株式会社 | 有机金属化合物、包括有机金属化合物的有机发光器件和包括有机金属化合物的诊断组合物 |
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US20190100546A1 (en) * | 2017-09-29 | 2019-04-04 | Samsung Electronics Co., Ltd. | Organometallic compound, organic light-emitting device including the organometallic compound, and diagnostic composition including the organometallic compound |
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US20150194615A1 (en) * | 2014-01-07 | 2015-07-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN107056844A (zh) * | 2016-02-11 | 2017-08-18 | 三星电子株式会社 | 有机金属化合物、包括有机金属化合物的有机发光器件和包括有机金属化合物的诊断组合物 |
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