WO2021128982A1 - 一种o^c^n^n型四齿铂(ii)配合物、制备方法及其应用 - Google Patents
一种o^c^n^n型四齿铂(ii)配合物、制备方法及其应用 Download PDFInfo
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- WO2021128982A1 WO2021128982A1 PCT/CN2020/116339 CN2020116339W WO2021128982A1 WO 2021128982 A1 WO2021128982 A1 WO 2021128982A1 CN 2020116339 W CN2020116339 W CN 2020116339W WO 2021128982 A1 WO2021128982 A1 WO 2021128982A1
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- atoms
- halogen
- substituted
- alkyl
- complex
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- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title abstract description 6
- 239000000463 material Substances 0.000 claims abstract description 17
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 53
- 229910052736 halogen Inorganic materials 0.000 claims description 40
- 150000002367 halogens Chemical class 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 18
- -1 cyano, carboxy, styryl Chemical group 0.000 claims description 18
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- 229910052805 deuterium Inorganic materials 0.000 claims description 8
- 125000004986 diarylamino group Chemical group 0.000 claims description 8
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 8
- 239000000758 substrate Substances 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 239000003446 ligand Substances 0.000 claims description 6
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 5
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000004442 acylamino group Chemical group 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 239000002019 doping agent Substances 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 239000002243 precursor Substances 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 238000002207 thermal evaporation Methods 0.000 claims description 3
- 230000009471 action Effects 0.000 claims description 2
- 238000007641 inkjet printing Methods 0.000 claims description 2
- 238000004528 spin coating Methods 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims 1
- 230000006872 improvement Effects 0.000 abstract description 3
- 239000011368 organic material Substances 0.000 abstract description 3
- 230000021715 photosynthesis, light harvesting Effects 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 239000010410 layer Substances 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000005516 engineering process Methods 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000018109 developmental process Effects 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- 239000013212 metal-organic material Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910001385 heavy metal Inorganic materials 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 0 *c(c(*)c(cc12)-c3c(*)c(*)c(*)c(O*)c3O)c1c(c(*)c(*)c(*)c1*)c1[n]2-c1c(*)c(*)c(*)c(-c2c(*)c(*)c(*)c(*)n2)n1 Chemical compound *c(c(*)c(cc12)-c3c(*)c(*)c(*)c(O*)c3O)c1c(c(*)c(*)c(*)c1*)c1[n]2-c1c(*)c(*)c(*)c(-c2c(*)c(*)c(*)c(*)n2)n1 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
- 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
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- 230000009286 beneficial effect Effects 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
- 229940125898 compound 5 Drugs 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000005401 electroluminescence Methods 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
- 239000011521 glass Substances 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 230000003993 interaction 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
- 125000002524 organometallic group Chemical group 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 2
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- 230000008016 vaporization Effects 0.000 description 2
- 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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-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
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical group NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 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
- 125000004429 atom Chemical group 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
- 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
- 125000006267 biphenyl group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 230000001808 coupling effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 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
- 150000004985 diamines Chemical class 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
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- 150000002240 furans Chemical class 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 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
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- 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
- 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
- 238000004020 luminiscence type Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 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
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 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
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- CAMRHYBKQTWSCM-UHFFFAOYSA-N oxocyanamide Chemical compound O=NC#N CAMRHYBKQTWSCM-UHFFFAOYSA-N 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 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
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 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
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 238000010992 reflux Methods 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
- 239000002356 single layer Substances 0.000 description 1
- 238000010129 solution processing Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
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Definitions
- the present invention relates to a novel O ⁇ C ⁇ N ⁇ N tetradentate platinum (II) complex metal organic material, in particular to a phosphorescent doped material used in the light-emitting layer of an OLED light-emitting device to emit red light photons.
- II tetradentate platinum
- OLED display technology is the latest display technology with broad development prospects. Following CRT and LCD, OLED display technology was born. It has self-luminous characteristics, does not require a backlight, has high visibility and brightness, wide viewing angle, and fast response; the material is light in weight, thin in thickness, and has a flexible display. Superior performance; at the same time, compared with LCD, the voltage requirement is low, the component requirement is less, and the cost is low. OLED has superior performance and will be widely used in smart phones, TVs, wearable devices and VR fields in the future, with broad development prospects.
- the thickness of the anthracene monolithic wafer is in the micron level (10-20 ⁇ m), and it is necessary to use a DC voltage of up to 400V to make a single-layer light-emitting device, applying a voltage of 400V, a weak blue light is observed, and the life of the device is also very short, lacking practical Therefore, the value of application has not attracted widespread attention in the academic circles.
- phosphorescent OLED light-emitting layer doping materials have developed rapidly and maturely, which are mainly based on some heavy metal organic complexes, such as iridium, platinum, europium, and osmium.
- heavy metal organic complexes such as iridium, platinum, europium, and osmium.
- SOC spin-orbital coupling effect
- This method simultaneously captures triplet and singlet excitons, effectively uses triplet excitons that cannot emit light, and breaks the 25% bottleneck of internal quantum efficiency, so theoretically its quantum efficiency can reach 100%.
- OLED display technology is an arduous and significant research. It has good characteristics, but also has short service life, poor color purity, and easy aging, which limit the large-scale application of OLED technology. Therefore, designing new types of OLED materials with excellent performance, especially doped materials for the light-emitting layer, is the focus and difficulty of research in the OLED field.
- Carbazole is a kind of electron-rich nitrogen-containing heterocyclic compound with a large ⁇ -conjugated rigid planar structure. This unique structure makes its derivatives exhibit many excellent photoelectric properties.
- novel O ⁇ C ⁇ N ⁇ N tetradentate platinum (II) complex metal-organic material involved in the present invention has the structure shown in the following formula (I):
- R 1 -R 17 are independently selected from hydrogen, deuterium, sulfur, halogen, hydroxyl, acyl, alkoxy, acyloxy, amino, nitro, acylamino, cyano, carboxy, styryl, aminocarbonyl , Carbamoyl, benzylcarbonyl, aryloxy, silyl, diarylamino, saturated alkyl containing 1-30 C atoms, unsaturated alkyl containing 1-20 C atoms, substituted or unsubstituted
- the substituted aryl group containing 5-30 C atoms, the substituted or unsubstituted heteroaryl group containing 5-30 C atoms, or adjacent R 1 -R 17 are connected to each other through a covalent bond to form a ring; Substitution is substituted by deuterium, halogen, cyano, nitro, amino, C1-C8 alkyl, and the heteroatoms in the heteroaryl group are N, S, O atoms
- R 1 -R 17 are independently selected from hydrogen, halogen, amino, nitro, cyano, silyl, diarylamino, saturated alkyl containing 1-10 C atoms, halogen or one or more A C1-C4 alkyl substituted or unsubstituted aryl group containing 5-20 C atoms, a halogen or one or more C1-C4 alkyl substituted or unsubstituted heterocyclic groups containing 5-20 C atoms
- the aryl group or adjacent R 1 -R 16 are connected to each other through a covalent bond to form a ring, and the halogen is F, Cl, Br.
- R 1 '-R 5' are independently selected from hydrogen, halo, silyl, di-arylamino, saturated alkyl group containing 1-10 C atoms, with one or more halogen or C1-C4 alkyl substituted by Or unsubstituted aryl group containing 5-20 C atoms, heteroaryl group containing 5-20 C atoms substituted or unsubstituted by halogen or one or more C1-C4 alkyl groups, or adjacent R 1 '-R 5 'are mutually connected to form a ring via a covalent bond, and the halogen is F, Cl, Br.
- R 1 '-R 5' 5 groups wherein there are 0-3 groups independently represents a diarylamino group, halogen or 1-3 C1-C4 alkyl substituted or unsubstituted Substituted aryl groups containing 5-10 C atoms, heteroaryl groups containing 5-10 C atoms substituted or unsubstituted by halogen or 1 to 3 C1-C4 alkyl groups; other groups are independently represented It is hydrogen, halogen or saturated alkyl containing 1-8 C atoms, and the halogen is F, Cl.
- R 1 '-R 5' 5 groups wherein there are 0-3 groups independently represent as diphenylamino, C1-C4 alkyl substituted or unsubstituted phenyl, pyridyl, carbazole
- the azole group and other groups are independently represented by hydrogen, fluorine, and saturated alkyl containing 1 to 4 C atoms.
- R 1 -R 17 are selected from hydrogen, deuterium, sulfur, halogen, hydroxyl, acyl, alkoxy, acyloxy, amino, nitro, acylamino, cyano, carboxy, styryl, aminocarbonyl , Carbamoyl, benzylcarbonyl, aryloxy, silyl, diarylamino, saturated alkyl containing 1-30 C atoms, unsaturated alkyl containing 1-20 C atoms, substituted or unsubstituted
- the substituted aryl group contains 5-30 C atoms
- the substituted or unsubstituted heteroaryl group contains 5-30 C atoms
- R 1 -R 16 are connected to each other through a covalent bond to form a ring; Substitution is substituted by deuterium, halogen, cyano, nitro, amino, C1-C8 alkyl, and the heteroatoms in the heteroaryl group are N, S, O atoms.
- R 1 '-R 5' are independently selected from hydrogen, halo, silyl, di-arylamino, saturated alkyl group containing 1-10 C atoms, containing 5 to 20 C atoms or one or more halogen a 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 ′ are connected to each other through a covalent bond to form a ring, and the halogen is F, Cl, Br.
- 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, and most preferably F.
- the above-mentioned covalent bond to form a ring, aryl, and heteroaryl include groups having 5-30 carbon atoms, preferably 5-20 carbon atoms, more preferably 5-10 carbon atoms and composed of one aromatic ring or multiple fused
- the aromatic ring consists of the aryl group.
- Suitable aryl groups are, for example, phenyl, naphthyl, acenaphthenyl, acenaphthenyl, anthracenyl, fluorenyl, phenalenyl.
- the aryl group can be unsubstituted (that is, 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 groups, preferably alkyl groups having 1-20, 1-10 or 1-8 carbon atoms, particularly preferably methyl, ethyl, isopropyl Aryl group or tert-butyl group; aryl group, preferably a C 5 , C 6 aryl group or fluorenyl group that can be substituted again or unsubstituted; heteroaryl group, preferably a heteroaryl group containing at least one nitrogen atom, particularly preferably a pyridyl group;
- the aryl group particularly preferably has a substituent selected from the group consisting of F, methyl and tert-butyl, or an aryl group optionally substituted
- the unsaturated alkyl group containing 1-20 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 1-8 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 with respect to the aryl group.
- 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 a single bond attached to the CO group, such as an alkyl group as used herein.
- alkoxy group is directly connected to oxygen by a single bond, such as the alkyl group used herein.
- heteroaryl groups are understood to be related to aromatic, C 3 -C 8 cyclic groups, and also contain one oxygen or sulfur atom or 1 to 4 nitrogen atoms or a combination of one oxygen or sulfur atom and up to two nitrogen atoms , And their substituted and benzo- and pyrido-fused derivatives, for example, via one of the ring-forming carbon atoms, the heteroaryl group may be substituted by one or more of the mentioned aryl substituents Replaced.
- the heteroaryl group may be a five- or six-membered aromatic heterocyclic ring system with independent 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, pteridine, benzoxazole, diazole, benzopyrazo
- the complex is applied in the form of 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 above-mentioned organic light-emitting device emits orange-red when a current is applied.
- the organometallic complex in the present invention has high fluorescence quantum efficiency, good thermal stability and low quenching constant, and can manufacture red light OLED devices with high luminous efficiency and low roll-off.
- Fig. 1 is a schematic diagram of the structure of the organic electroluminescent device of the present invention.
- the preparation method of the above complex includes the following steps:
- carbazole derivatives S1 and S2 are reacted by Suzuki to obtain substrate S3, S3 and S4 are reacted by Buchwald to obtain S5, and S5 is demethylated under the action of pyridine hydrochloride to obtain ligands S6, S6 and K 2 PtCl 4 reaction to obtain the target product P.
- the initial substrates and solvents involved in the synthesis of the compounds in the present invention are all from the suppliers well-known to those skilled in the art, such as Anegie, Bailingwei, Aladdin and the like.
- Synthesis of compound 3 Take 9.84g (40.0mmol) of compound 1, 6.69g of compound 2 (1.1eq., 44.0mmol), potassium carbonate 11.04g (2.0eq., 80mmol) and Pd(PPh 3 ) 4 924mg (0.02eq. ., 0.8mmol), added to a three-necked flask, vacuumed and replaced with nitrogen for several times, then injected 120mL of dioxane, 40mL of water, and heated to 105°C.
- Synthesis of compound 5 take 5.47g (20mmol) of compound 3, 5.17g (1.1eq., 22mmol) of compound 4, palladium acetate 225mg (0.02eq., 1mmol), tri-tert-butylphosphine 0.20g (0.04eq., 2mmol) ), 4.5 g (2.0 eq., 0.04 mol) of potassium tert-butoxide in the flask, add 100 mL of toluene, and heat and reflux for 8 hours under the protection of nitrogen.
- Synthesis of compound TM-1 Take 2.06g (5.0mmol) of compound 6,400mg of tetrabutylammonium bromide (0.25eq., 1.25mmol) and 2.49mg (1.2eq., 6mmol) of potassium tetrachloroplatinate, and dissolve in 150mL In the acetic acid, evacuated and introduced nitrogen for several times, stirred and heated to 130°C to react for 12 hours. After the reaction, the solvent was removed by cooling and rotary evaporation, then an appropriate amount of water and ethyl acetate were added for extraction, the organic phase was collected, dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation.
- TM-3 The preparation method of TM-3 is the same as the synthetic route of TM-1, the only difference is that compound 7 is used instead of compound 1.
- the molecular formula of compound 7 is as follows:
- TM-5 The preparation method of TM-5 is the same as that of TM-1, the only difference is that compound 7 is used instead of compound 1, and compound 8 is used instead of compound 4.
- the molecular formula of compound 8 is as follows:
- the transparent anodized indium tin oxide (ITO, 20) (10 ⁇ /sq) glass substrate 10 was ultrasonically cleaned with acetone, ethanol, and distilled water in sequence, and then treated with oxygen plasma for 5 minutes.
- the ITO substrate was mounted on the substrate holder of the vacuum vapor deposition equipment.
- the pressure of the control system is 10 -6 torr.
- the hole transport layer (30) material TAPC with a thickness of 60 nm was evaporated on the ITO substrate.
- the light-emitting layer material (40) TCTA with a thickness of 40 nm is evaporated, and the platinum (II) complex is doped with 10% mass fraction.
- the electron transport layer (50) material TmPyPb with a thickness of 30 nm is 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 completely the same, the difference is that the organometallic complexes P0, P1, P2, P3, and P4 are sequentially used as the dopant and doping concentration in the light-emitting layer. Among them, STD's O ⁇ N ⁇ N ⁇ O red light material.
- the device STD, device 1, device 2, and device 3 are prepared in sequence.
- the structure and manufacturing method of the device are exactly the same.
- the difference is that the platinum (II) complexes STD, TM-1, TM-3, and TM-5 are used in sequence as the light-emitting layer. Dopants.
- the reference material STD is a classic red light material with an ONCN coordination structure.
- the comparison results of the devices are shown in Table 1, based on the performance of the device STD;-indicates that the data is flat, - indicates that the relative baseline performance is reduced by more than 5%, + indicates that the relative baseline performance is increased by 5%, and ++ indicates the relative baseline performance An increase of 10%.
- the maximum external quantum efficiency and the turn-on voltage of the TM-1 based device 1 are basically the same, and the external quantum efficiency and current efficiency under 100nit are improved by about 5%; from the point of view of molecular structure , TM-1 and STD both have the same planar structure, but TM-1 has a larger conjugate structure, which improves the device performance to a certain extent relative to STD.
- device 2 based on TM-3 has basically the same turn-on voltage, but the maximum external quantum efficiency and the external quantum efficiency and current efficiency under 100nit are all improved by about 5%.
- the introduction of two tert-butyl groups in the molecular structure of TM-3 reduces the aggregation and stacking between molecules to a certain extent, which is beneficial to the improvement of device performance.
- device 3 based on TM-5 has basically the same turn-on voltage, but the maximum external quantum efficiency and the external quantum efficiency and current efficiency under 100nit are all improved by about 10%; from the point of view of molecular structure, TM- 3
- the introduction of 4 tert-butyl groups in the molecular structure greatly enhances the three-dimensionality of the molecule, greatly reduces the interaction between molecules, while maintaining the rigid structure and large conjugation characteristics of the molecular skeleton, so that the device efficiency is maximized and the performance is the best .
- the performance of the organic electroluminescent device prepared by the present invention has a better performance improvement compared with the reference device, the external quantum efficiency, or the current efficiency is significantly improved, and the new type O ⁇ C ⁇ N ⁇ N involved
- the metal-organic materials of dentate platinum (II) complexes have great application value.
- the tetradentate platinum (II) complex involved in the present invention is based on the carbazole skeleton and has a large ⁇ -conjugated rigid planar structure, which can greatly reduce non-radiative energy dissipation such as intramolecular rotation and vibration, and is beneficial to platinum (II) )
- the luminous efficiency and performance of the complex are improved.
- the O ⁇ C ⁇ N ⁇ N tetradentate platinum (II) complex metal organic material prepared by the present invention has great application value in organic light emitting diodes, and is used as a phosphorescent doped material to produce red light OLEDs with high luminous efficiency Device.
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Abstract
Description
器件1 | 器件2 | 器件3 | |
最大外量子效率 | ‐ | + | ++ |
100nit下的外量子效率 | + | + | ++ |
启亮电压 | ‐ | ‐ | ‐ |
100nit下的电流效率 | + | + | ++ |
Claims (12)
- 权利要求1所述的配合物,其中R 1-R 17独立的选自氢、卤素、氨基、硝基、氰基、硅烷基、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 16相互通过共价键连接成环,所述卤素为F,Cl,Br。
- 权利要求3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。
- 权利要求4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1-6任一配合物在OLED发光器件中的应用。
- 根据权利要求10所述的应用,所述权利要求1-6所述的任一配合物采用通过热沉积、旋涂、喷墨打印以层形式施加在OLED发光器件中。
- 根据权利要求10所述的应用,所述权利要求1-6任一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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US17/776,978 US20220416180A1 (en) | 2019-12-24 | 2020-09-19 | O^c^n^n-type tetradentate platinum (ii) complex, preparation method therefor, and application thereof |
KR1020227013155A KR102699343B1 (ko) | 2019-12-24 | 2020-09-19 | O^c^n^n형 4좌 백금(ii) 배합물, 제조 방법 및 이의 응용 |
JP2022531588A JP7332809B2 (ja) | 2019-12-24 | 2020-09-19 | O-c-n-n型四座配位白金(ii)錯体、調製方法及びその用途 |
DE112020004784.9T DE112020004784T5 (de) | 2019-12-24 | 2020-09-19 | Tetradentatplatin(II)-Koordinationsverbindung vom O^C^N^N-Typ, deren Herstellungsverfahren und Anwendung |
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JP7332809B2 (ja) | 2023-08-23 |
US20220416180A1 (en) | 2022-12-29 |
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