TW201307365A - 作為全彩顯示器中窄頻帶磷光發光體之鉑及鈀錯合物之合成 - Google Patents
作為全彩顯示器中窄頻帶磷光發光體之鉑及鈀錯合物之合成 Download PDFInfo
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- TW201307365A TW201307365A TW101118850A TW101118850A TW201307365A TW 201307365 A TW201307365 A TW 201307365A TW 101118850 A TW101118850 A TW 101118850A TW 101118850 A TW101118850 A TW 101118850A TW 201307365 A TW201307365 A TW 201307365A
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- atom
- phenyl
- composition
- platinum
- carbon
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 title claims abstract description 69
- 229910052697 platinum Inorganic materials 0.000 title claims abstract description 31
- 150000002940 palladium Chemical class 0.000 title abstract description 5
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical class [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 54
- 229910052763 palladium Chemical class 0.000 claims abstract description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 106
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 89
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 78
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 54
- 239000000203 mixture Substances 0.000 claims description 53
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 53
- 125000003118 aryl group Chemical group 0.000 claims description 46
- 229910052757 nitrogen Inorganic materials 0.000 claims description 44
- 125000000623 heterocyclic group Chemical group 0.000 claims description 42
- 229910052799 carbon Inorganic materials 0.000 claims description 41
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 40
- 229910052698 phosphorus Inorganic materials 0.000 claims description 30
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims description 26
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 26
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 26
- 229910052796 boron Inorganic materials 0.000 claims description 26
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 claims description 26
- 239000011574 phosphorus Substances 0.000 claims description 26
- 229910052717 sulfur Inorganic materials 0.000 claims description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 17
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 239000001301 oxygen Substances 0.000 claims description 14
- 239000011593 sulfur Substances 0.000 claims description 14
- 125000004429 atom Chemical group 0.000 claims description 13
- 239000003446 ligand Substances 0.000 claims description 13
- 125000001624 naphthyl group Chemical group 0.000 claims description 13
- 239000000460 chlorine Substances 0.000 claims description 10
- 229910052787 antimony Inorganic materials 0.000 claims description 9
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 9
- 150000002825 nitriles Chemical class 0.000 claims description 9
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 8
- 229910052707 ruthenium Inorganic materials 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 229910052732 germanium Inorganic materials 0.000 claims description 5
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 125000004437 phosphorous atom Chemical group 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 claims description 2
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- 125000000217 alkyl group Chemical group 0.000 description 29
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000000295 emission spectrum Methods 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 7
- 239000003480 eluent Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- -1 for example Chemical group 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 4
- PJRGCJBBXGNEGD-UHFFFAOYSA-N 2-bromo-9h-carbazole Chemical compound C1=CC=C2C3=CC=C(Br)C=C3NC2=C1 PJRGCJBBXGNEGD-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 229910000420 cerium oxide Inorganic materials 0.000 description 4
- 230000005283 ground state Effects 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 4
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- SVAHHCNTAZYUAT-UHFFFAOYSA-N 1-(4-bromophenyl)-2-nitrobenzene Chemical group [O-][N+](=O)C1=CC=CC=C1C1=CC=C(Br)C=C1 SVAHHCNTAZYUAT-UHFFFAOYSA-N 0.000 description 3
- PWQVEKCOZSQKAW-UHFFFAOYSA-N 2-bromo-9-(oxan-2-yl)carbazole Chemical compound C=1C(Br)=CC=C(C2=CC=CC=C22)C=1N2C1CCCCO1 PWQVEKCOZSQKAW-UHFFFAOYSA-N 0.000 description 3
- RDNBQLKCMFLYLS-UHFFFAOYSA-N 2-bromo-9-pyridin-2-ylcarbazole Chemical compound C=1C(Br)=CC=C(C2=CC=CC=C22)C=1N2C1=CC=CC=N1 RDNBQLKCMFLYLS-UHFFFAOYSA-N 0.000 description 3
- NMQKVPDXWFXQTR-UHFFFAOYSA-N 2-pyrazol-1-yl-9h-carbazole Chemical compound C1=CC=NN1C1=CC=C2C3=CC=CC=C3NC2=C1 NMQKVPDXWFXQTR-UHFFFAOYSA-N 0.000 description 3
- NNZFNCOCGLXAOR-UHFFFAOYSA-N 9-(oxan-2-yl)-2-pyrazol-1-ylcarbazole Chemical compound O1CCCCC1N1C2=CC(N3N=CC=C3)=CC=C2C2=CC=CC=C21 NNZFNCOCGLXAOR-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 3
- 230000005281 excited state Effects 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- WXHIJDCHNDBCNY-UHFFFAOYSA-N palladium dihydride Chemical compound [PdH2] WXHIJDCHNDBCNY-UHFFFAOYSA-N 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 125000003396 thiol group Chemical class [H]S* 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 description 2
- 125000000041 C6-C10 aryl group Chemical group 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 2
- 229930182821 L-proline Natural products 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 230000005693 optoelectronics Effects 0.000 description 2
- 229960002429 proline Drugs 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 2
- LWHHAVWYGIBIEU-LURJTMIESA-N (2s)-2-methylpyrrolidin-1-ium-2-carboxylate Chemical compound [O-]C(=O)[C@]1(C)CCC[NH2+]1 LWHHAVWYGIBIEU-LURJTMIESA-N 0.000 description 1
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical group CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 description 1
- YOJKKXRJMXIKSR-UHFFFAOYSA-N 1-nitro-2-phenylbenzene Chemical group [O-][N+](=O)C1=CC=CC=C1C1=CC=CC=C1 YOJKKXRJMXIKSR-UHFFFAOYSA-N 0.000 description 1
- ZROILLPDIUNLSE-UHFFFAOYSA-N 1-phenyl-1h-pyrazole-4-carboxylic acid Chemical compound C1=C(C(=O)O)C=NN1C1=CC=CC=C1 ZROILLPDIUNLSE-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 239000012327 Ruthenium complex Substances 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000001204 arachidyl 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])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
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000005162 aryl oxy carbonyl amino group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 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
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- VYLVYHXQOHJDJL-UHFFFAOYSA-K cerium trichloride Chemical compound Cl[Ce](Cl)Cl VYLVYHXQOHJDJL-UHFFFAOYSA-K 0.000 description 1
- SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 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
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 125000005266 diarylamine group Chemical group 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 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
- 125000005553 heteroaryloxy group Chemical group 0.000 description 1
- 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 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002463 lignoceryl 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])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])C([H])([H])[H] 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 125000001421 myristyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 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
- 238000005457 optimization Methods 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000000913 palmityl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 230000005258 radioactive decay Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229930192474 thiophene Chemical group 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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Abstract
本發明揭示可用作窄頻帶磷光發光體之鉑及鈀錯合物。亦揭示製備及使用該等鉑及鈀錯合物之方法。
Description
本揭示內容係關於可用作(例如)全彩顯示器中之窄頻帶磷光發光體之鉑及鈀錯合物。
本申請案主張2011年5月26日提出申請之美國申請案第61/490,111號之權利,其全部內容以引用方式併入本文中。
本發明係在國家科學基金會(National Science Foundation)Career獎金第0748867號之財政支持下獲得。美國政府具有本發明之某些權利。
理想地,能夠吸收及/或發射光之化合物適應於各種應用中,包含光學及光電裝置、光吸收裝置及生物應用(作為標記物)。許多研究致力於研究及優化用於該等應用中之有機及有機金屬材料。通常,此領域中之研究旨在達成諸多目標,尤其包含改良吸收及發射效率以及改良處理能力。
儘管致力於光學、光電及標記物材料之研究已取得顯著進步,但現有材料仍具有諸多缺點,尤其包含較差處理能力、低效發射或吸收及小於理想情形之穩定性。因此,需要在光學發射及吸收應用中展現改良性能之新材料。藉由本發明來滿足此需要及其他需要。
本發明係關於可用作(例如)全彩顯示器中之窄頻帶磷光
發光體之鉑及鈀錯合物。該等錯合物可用於有機發光二極體(OLED)中。
通常,OLED包括至少一個佈置於陽極與陰極之間且電連結至陽極及陰極之有機層。在施加電流時,陽極向有機層中注入電洞且陰極向有機層中注入電子。注入之電洞及電子各自朝向帶相反電荷之電極遷移。在電子與電洞定位於同一分子上時,形成「激子」,亦即具有激發能態之定域電子-電洞對。在該激子經由光電發射機制弛豫時,發射光。在一些情形下,激子可定位於激基締合物或激基複合物上。亦可存在非輻射機制(例如熱弛豫),但其通常認為不理想。在一態樣中,本發明提供可藉由通式:
代表之錯合物中(N^C)代表配體之發射部分,(L^X)代表配體之可連接或不連接之輔助部分,M代表鉑或鈀,R代表連結(N^C)與(L^X)同時破壞其間之共軛之連接基序。
在一態樣中,錯合物之激發態性質可由以下圖式代表:
可獨立地調整以配體為中心之三重態(3LC)及金屬至配體電荷轉移狀態(1MLCT)之能量。發射部分(N^C)之性質會影響發射能量以及發射特徵之寬度。輔助部分(L^X)之性質決定發射特徵中振動序列之增強或阻抑以及與發射有關之衰變速率。控制此二者可得到在用於顯示器應用之波長下窄發射之錯合物。
在一態樣中,本發明提供可由下式代表之錯合物:
其中M代表鉑、鈀或其組合,其中Ar1、Ar2及Ar3中之每一者獨立地代表可經取代或未經取代之芳族環或雜環基團;其中X1、X2及X3中之每一者可個別地配位至鉑及/或鈀原
子,且可獨立地代表碳或氮原子,其中Ar5可代表芳族環、雜環基團或其組合,其中Ar6可代表芳族環、雜環基團、其組合或可不存在;其中W可配位至鉑或鈀原子,且可代表可經取代且直接或經由氧原子、硫原子、氮原子或磷原子鍵結之鹵素原子、芳基或雜芳基;其中A可代表連接原子,例如氮、碳、硼、磷、矽或其組合,且其中A可視情況經取代,其中b1、b2及b3中之每一者可個別地視情況存在或不存在,且若存在則可獨立地代表氧、硫、氮、碳、硼、磷、矽或其組合。
在另一態樣中,本發明提供可由下式代表之錯合物:
其中M代表鉑、鈀或其組合,其中Ar1、Ar2、Ar3及Ar4中之每一者獨立地代表可經取代或未經取代之芳族環或雜環基團;其中X1、X2、X3及X4中之每一者可個別地配位至鉑及/或鈀原子,且可獨立地代表碳及/或氮原子,其中Ar5可代表芳族環、雜環基團或其組,其中Ar6可代表芳族環、雜環基團、其組合或可不存在;其中A1及A2中之每一者可獨立地代表連接原子,例如氮、碳、硼、磷、矽或其組
合,且其中A1及A2中之每一者可獨立地視情況經取代,其中b1及b2中之每一者可個別地視情況存在或不存在,且若存在則可獨立地代表氧、硫、氮、碳、硼、磷、矽或其組合。
在又一態樣中,本發明提供可由下式代表之錯合物:
其中M代表鉑、鈀或其組合,其中Ar1、Ar2、Ar3及Ar4中之每一者獨立地代表可經取代或未經取代之芳族環或雜環基團;其中X1、X2、X3及X4中之每一者可個別地配位至鉑及/或鈀原子,且可獨立地代表碳及/或氮原子,其中Ar5可代表芳族環、雜環基團或其組合,其中Ar6可代表芳族環、雜環基團、其組合或可不存在;其中A1可代表連接原子,例如氮、碳、硼、磷、矽或其組合,且其中A1可視情況經取代,其中b1、b2及b3中之每一者可個別地視情況存在或不存在,且若存在則可獨立地代表氧、硫、氮、碳、硼、磷、矽或其組合。
亦揭示包括本文所闡述鉑錯合物中之一或多者之全彩顯
示器裝置。
納入本說明書中且構成其一部分之附圖闡釋若干態樣且與該說明一起用於闡述本發明之原理。
本發明之其他態樣將在下文說明中部分地加以闡述,且根據本說明將部分地顯而易見,或可藉由實踐本發明而知曉。藉助隨附申請專利範圍中特定指出之要素及組合實現及達成本發明之優點。應理解,上文一般說明及下文詳細說明二者僅係例示性及闡釋性,且並非限制所主張之本發明。
參照下列本發明之詳細說明及其中所包含實例可更容易地理解本發明。
在揭示及闡述本發明化合物、裝置及/或方法之前,應理解,除非另外指出,否則其並不限於具體合成方法,或除非另外指出,否則其並不限於特定試劑,因此其當然可有所變化。亦應理解,本文所用之術語僅係出於闡述特定態樣之目的,而並非意欲加以限制。儘管在本發明之實踐或測試中可使用與彼等本文所闡述者相類似或相當之任何方法及材料,但現將對實例性方法及材料加以闡述。
本文所揭示之化學名稱及結構亦可包括自彼等結構產生之鍵。舉例而言,若係吡啶,則來自結構之鍵包含於吡啶中,因此,舉例而言,X1可為吡啶中鍵
結至錯合物之另一組份(例如M組份)之氮或碳。
除非上下文另外明確說明,否則本說明書及隨附申請專利範圍中所用之單數形式「一(a、an)」及「該」包含複數個指示物。因此,舉例而言,提及「組份」包含兩種或更多種組份之混合物。
在本文中,範圍可表示為自「約」一個特定值及/或至「約」另一特定值。在表達此一範圍時,另一態樣包含自該一個特定值及/或至該另一個特定值。類似地,在數值藉由使用先行詞「約」表達為近似值時,應理解,該特定值可形成另一態樣。應進一步理解,各範圍之端點在與另一端點有關及與另一端點無關兩種情況下皆具有意義。亦應理解,本文揭示了許多數值,且各個值除該值自身以外在本文中亦揭示為「約」該特定值。舉例而言,若揭示值「10」,則亦揭示「約10」。亦應理解,亦揭示兩個特定單位之間之每一單位。舉例而言,若揭示10與15,則亦揭示11、12、13及14。
本文所用之術語「可選」或「視情況」意指隨後所述之事件或情況可能發生或可能不發生,且說明書包含其中該事件或情形發生之情況及其中該事件或情形不發生之情況。
本文所用之術語「烷基」係1至24個碳原子之具支鏈或不具支鏈飽和烴基團,例如,甲基、乙基、正丙基、異丙基、正丁基、異丁基、第二丁基、第三丁基、正戊基、異戊基、第二戊基、新戊基、己基、庚基、辛基、壬基、癸
基、十二烷基、十四烷基、十六烷基、二十烷基、二十四烷基及諸如此類。烷基可為環狀或非環狀。烷基可具支鏈或不具支鏈。烷基亦可經取代或未經取代。舉例而言,烷基可經一或多個包含但不限於以下之基團取代:視情況經取代之烷基、環烷基、烷氧基、胺基、醚、鹵化物、羥基、硝基、甲矽烷基、磺基-側氧基或硫醇,如本文中所闡述。「低碳烷基」基團係含有1至6個(例如,1至4個)碳原子之烷基。
本文所用之術語「胺」或「胺基」係由式NA1A2A3代表,其中A1、A2及A3可獨立地係氫或視情況經取代之烷基、環烷基、烯基、環烯基、炔基、環炔基、芳基或雜芳基,如本文中所闡述。
本文所用之術語「鹵化物」係指鹵素氟、氯、溴及碘。
本文所用之術語「羥基」係由式-OH代表。
本文所用之術語「硝基」係由式-NO2代表。
本文所用之術語「腈」係由式-CN代表。
本文所用之術語「硫醇」係由式-SH代表。
本發明揭示用於製備本發明組合物之組份以及欲用於本文所揭示方法中之組合物自身。本文揭示該等及其他材料,且應理解,在揭示該等材料之組合、子組、相互作用、基團等時,儘管可能未明確揭示對該等化合物之各個單獨個體及集體組合及其排列之具體提及,但各種情形皆特定涵蓋且闡述於本文中。舉例而言,若揭示且論述特定化合物且論述可對許多分子(包含該等化合物)實施若干改
變,除非明確表示相反情況,否則該化合物之每種組合及排列及可能的改變皆特定涵蓋其中。因此,若揭示一類分子A、B及C以及一類分子D、E及F且揭示組合分子A-D之實例,則即使未個別列舉每一者,亦個別且共同涵蓋每一者,此意味著認為揭示組合A-E、A-F、B-D、B-E、B-F、C-D、C-E及C-F。同樣,亦揭示該等之任何子組或組合。因此,舉例而言,應認為揭示A-E、B-F及C-E之子群。此概念適用於此申請案之所有態樣,其包含但不限於製備及使用本發明組合物之方法中的各個步驟。因此,若存在許多可實施之其他步驟,則應理解,該等其他步驟中的每一者可由本發明方法之任一特定實施例或實施例之組合實施。
術語「雜環」或類似術語係指包含雜原子之環狀結構。因此,「雜環」包含具有一或多個雜原子之芳族及非芳族環結構。雜環之非限制性實例包含吡啶、異喹啉、甲基吡咯及噻吩等。
如上文中所簡述,本發明係關於鉑及/或鈀錯合物。在一態樣中,本文所揭示之組合物可提供鉑及/或鈀之發射光譜。在另一態樣中,本文所揭示之組合物可提供可調發射光譜。在又一態樣中,本文所揭示之組合物可具有擁有窄頻寬之發射光譜。
在一態樣中,發明性組合物包括鉑(II)錯合物。在另一態樣中,發明性組合物包括鈀(II)錯合物。
對於本文所列舉結構中之任一者,除非明確說明相反之
情形,否則使用各種符號及/或縮寫,其中:M代表鉑、鈀或其組合,其中Ar1、Ar2、Ar3及Ar4中之每一者(若存在)獨立地代表可經取代或未經取代之芳族環或雜環基團;其中每一Xn可配位至鉑及/或鈀原子,且可獨立地代表碳及/或氮原子,其中Ar5可代表芳族環、雜環基團或其組合,其中Ar6可代表芳族環、雜環基團、其組合或可不存在;其中每一An可獨立地代表連接原子,例如氮、碳、硼、磷、矽或其組合,且其中每一An可視情況經取代,其中每一bn可視情況存在或不存在,且若存在則可獨立地代表氧、硫、氮、碳、硼、磷、矽或其組合。
同樣,對於本文所列舉結構中之任一者而言,Rn可代表R1-R10,其中每一R可獨立地代表氫原子、烷基、鹵代烷基、芳烷基、烯基、炔基、芳基、胺基、單-或二烷基胺基、單-或二芳基胺基、烷氧基、芳氧基、雜芳氧基、烷氧基羰基、醯氧基、醯基胺基、烷氧基羰基胺基、芳氧基羰基胺基、磺醯基胺基、胺磺醯基、胺甲醯基、烷硫基、亞磺醯基、脲基、磷醯胺基團、羥基、巰基、鹵素原子、氰基、磺基、羧基、硝基、肼基、經取代甲矽烷基、可聚合基團或其組合;其中若存在複數個R(例如,Rn),,則n可為約0至約4,且其中每一R可與任一其他R相同或不同,且其中U(若存在)可為氧、硫或N-Rn。同樣,申請案中之名稱R1、R2、R3等係關於Rn之定義。因此,申請案中所列舉R1、R2、R3等之受限子組並不排除在該列表中亦包含定義為Rn之其他取代基。
在一態樣中,本發明之組合物可由以下通式代表:
其中M代表鉑、鈀或其組合,其中Ar1、Ar2及Ar3中之每一者獨立地代表可經取代或未經取代之芳族環或雜環基團;其中X1、X2及X3中之每一者可個別地配位至鉑及/或鈀原子,且可獨立地代表碳或氮原子,其中Ar5可代表芳族環、雜環基團或其組合,其中Ar6可代表芳族環、雜環基團、其組合或可不存在;其中W可配位至鉑或鈀原子,且可代表可經取代且直接或經由氧原子、硫原子、氮原子或磷原子鍵結之鹵素原子、芳基或雜芳基;其中A可代表連接原子,例如氮、碳、硼、磷、矽或其組合,且其中A可視情況經取代,其中b1、b2及b3中之每一者可個別地視情況存在或不存在,且若存在則可獨立地代表氧、硫、氮、碳、硼、磷、矽或其組合。
在一態樣中,M可為Pt,例如Pt(II)。在另一態樣中,M可為Pd,例如Pd(II)。
在一態樣中,W可為Cl或F。舉例而言,W可為Cl。在另一態樣中,W可為C3-C6炔基。舉例而言,W可為C3炔基。
在另一態樣中,W可為腈。在另一態樣中,W可為C6-C10芳基。舉例而言,W可為苯基或萘基。苯基或萘基可經取代或未經取代。舉例而言,苯基可未經取代。在另一實例中,苯基可經烷基取代,例如經C1-C6烷基取代。在另一態樣中,C6-C10芳基可經由氧原子鍵結至M。在另一態樣中,W可為C5-C9雜芳基。舉例而言,W可為異喹啉。在另一實例中,W可為喹唑啉。
在一態樣中,可為:吡啶、喹唑啉、異喹啉、甲基咪唑或。
在一態樣中,可為:苯基或吡啶。
在一態樣中,可為:苯基或吡啶。
在一態樣中,可為:苯基。
在一態樣中,可為苯基或可不存在。舉例而言,可不存在。在另一實例中,可為苯基。
在一態樣中,可為以下中之一或多者:
或其組合。在一態樣中,Rn可為C1-C3烷基。舉例而言,可為。
在一態樣中,可存在或不存在。舉例而言,可不存在。若存在,則在一態樣中可為-O-。
在一態樣中,可存在或不存在。舉例而言,可不存在。在另一實例中,可為-S-、-S(R1)2-、-C(R2)2-、-O-、-NH-或-NRn-。在一態樣中,每一R1可個別地為H或C1-C3烷基(例如C2烷基)。在一態樣中,每一R2可個別地為H或C1-C3烷基(例如C1烷基)。在一態樣中,Rn可為C1-C3烷基。舉例而言,Rn可為C2烷基。
在一態樣中,可存在或不存在。舉例而言,可不存在。在另一實例中,可為-S-、-S(R1)2-、-O-、-NH-或-NRn-。在一態樣中,每一R1可個別地為H或C1-C3烷基(例如C2烷基)。在一態樣中,Rn可為C1-C3烷基。舉例而言,Rn可為C2烷基。
在一態樣中,W可為Cl、腈、苯基、萘基或異喹啉;且可為異喹啉、甲基咪唑或。在另一態樣中,W可為Cl、腈、苯基、萘基或異喹啉;可為異喹啉、甲基咪唑或;且可為:苯基。在另一態樣中,W可為Cl、腈、苯基、萘基或異喹啉;可為異喹啉、甲基咪唑或;可為苯基;且可為吡啶。在另一態樣中,W可為Cl、腈、苯基、萘基或異喹啉;可為異喹啉、甲基咪唑或;可為苯基;可為吡啶;可為苯基;且可不存在。在另一態樣中,W可為Cl、腈、苯基、萘基或異喹啉;可為
異喹啉、甲基咪唑或;可為苯基;
可為吡啶;可為:苯基;且可為苯基。
在另一態樣中,本發明之組合物可由以下通式代表:
其中M代表鉑、鈀或其組合,其中Ar1、Ar2、Ar3及Ar4中之每一者獨立地代表可經取代或未經取代之芳族環或雜環基團;其中X1、X2、X3及X4中之每一者可個別地配位至鉑及/或鈀原子,且可獨立地代表碳及/或氮原子,其中Ar5可代表芳族環、雜環基團或其組,其中Ar6可代表芳族環、雜環基團、其組合或可不存在;其中A1及A2中之每一者可獨立地代表連接原子,例如氮、碳、硼、磷、矽或其組合,且其中A1及A2中之每一者可獨立地視情況經取代,其中b1及b2中之每一者可個別地視情況存在或不存在,且若存在則可獨立地代表氧、硫、氮、碳、硼、磷、矽或其組
合。
在一態樣中,M可為Pt,例如Pt(II)。在另一態樣中,M可為Pd,例如Pd(II)。
在一態樣中,可為:吡啶、喹唑啉、異喹啉、甲基咪唑或。
在一態樣中,可為:苯基或吡啶。
在一態樣中,可為:苯基或吡啶。
在一態樣中,可為苯基、吡啶、異喹啉、萘基、
舉例而言,可為苯基。在另一實例中,
可為吡啶。在另一實例中,可為萘基或異喹啉。
在一態樣中,可為:苯基。
在一態樣中,可為:苯基或不存在。舉例而
言,可不存在。在另一實例中,可為苯基。
在一態樣中,可為:或其組合。在一態樣中,Rn可為C1-C6烷基,例如C2烷基。舉例而言,可為
在一態樣中,可為:或其組合。在一態樣中,Rn可為C1-C6烷基,例如C2烷基。舉例而言,可為
。在另一態樣中,若不存在,則可為-O-。
在一態樣中,可存在或不存在。舉例而言,可不存在。若存在,則可為-O-。
在一態樣中,可存在或不存在。舉例而言,可不存在。在另一實例中,可為-S-、-S(R1)2-、-C(R2)2-、-O-、-NH-或-NRn-。在一態樣中,每一R1可個別地為H或C1-C3烷基(例如C2烷基)。在一態樣中,每一R2可個別地為H或C1-C3烷基(例如C1烷基)。在一態樣中,Rn可為C1-C3烷基。舉例而言,Rn可為C2烷基。
在一態樣中,可為吡啶、異喹啉、甲基咪唑或;且可為:苯基。在另一態樣中,可為吡啶、異喹啉、甲基咪唑或;
可為苯基;且可為吡啶。在另一態樣
中,可為吡啶、異喹啉、甲基咪唑或;
可為苯基;且可為苯基。在另一態樣
中,可為吡啶、異喹啉、甲基咪唑或;
可為苯基;可為吡啶或苯基;
可為:苯基;且可為苯基或吡啶。在另一態樣
中,可為吡啶、異喹啉、甲基咪唑或;
可為苯基;可為吡啶或苯基;且
可為苯基或吡啶;可為:苯基;且
可不存在。在另一態樣中,可為吡啶、異
喹啉、甲基咪唑或;可為苯基;
可為吡啶或苯基;且可為苯基或吡
啶;可為:苯基;且可為苯基。
在另一態樣中,本發明之組合物可由以下通式代表:
其中M代表鉑、鈀或其組合,其中Ar1、Ar2、Ar3及Ar4中之每一者獨立地代表可經取代或未經取代之芳族環或雜環基團;其中X1、X2、X3及X4中之每一者可個別地配位至鉑及/或鈀原子,且可獨立地代表碳及/或氮原子,其中Ar5可代表芳族環、雜環基團或其組合,其中Ar6可代表芳族環、雜環基團、其組合或可不存在;其中A1可代表連接原子,例如氮、碳、硼、磷、矽或其組合,且其中A1可視情況經取代,其中b1、b2及b3中之每一者可個別地視情況存在或不存在,且若存在則可獨立地代表氧、硫、氮、碳、硼、磷、矽或其組合。
在一態樣中,M可為Pt,例如Pt(II)。在另一態樣中,M可為Pd,例如Pd(II)。
在一態樣中,可為:吡啶、喹唑啉、異喹啉、甲基咪唑或。
在一態樣中,可為:苯基或吡啶。
在一態樣中,可為:苯基或吡啶。
在一態樣中,可為苯基、吡啶、異喹啉、萘基、
舉例而言,可為苯基。在另一實例中,可為吡啶。在另一實例中,可為萘基或異喹啉。
在一態樣中,可為:苯基。
在一態樣中,可為:苯基或不存在。舉例而言,可不存在。在另一實例中,可為苯基。
在一態樣中,可為:或其組合。在一態樣中,Rn可為C1-C6烷基,例如C2烷基。舉例而言,可為
在一態樣中,可存在或不存在。舉例而言,可不存在。若存在,則可為-O-。
在一態樣中,可存在或不存在。舉例而言,可不存在。在另一實例中,可為-S-、-S(R1)2-、-C(R2)2-、-O-、-NH-或-NRn-。在一態樣中,每一R1可個別地為H或C1-C3烷基(例如C2烷基)。在一
態樣中,每一R2可個別地為H或C1-C3烷基(例如C1烷基)。在一態樣中,Rn可為C1-C3烷基。舉例而言,Rn可為C2烷基。
在一態樣中,可為:或其組合。在一態樣中,Rn可為C1-C6烷基,例如C2烷基。舉例而言,可為
在一態樣中,可為吡啶、異喹啉、甲基咪唑或
;且可為:苯基。在另一態樣中,
可為異喹啉、甲基咪唑或;可
為苯基;且可為吡啶。在另一態樣中,
可為異喹啉、甲基咪唑或;可為苯基;
且可為苯基。在另一態樣中,可為異喹
啉、甲基咪唑或;可為苯基;
可為吡啶或苯基;且可為苯基或吡啶。在另一
態樣中,可為異喹啉、甲基咪唑或;
可為苯基;可為吡啶或苯基;且
可為苯基或吡啶;且可不存在。在另一
態樣中,可為異喹啉、甲基咪唑或;
可為苯基;可為吡啶或苯基;且
可為苯基或吡啶;且可為苯基。
在一態樣中,上述式
中之每一者可包括下列中之一或多者:
或其組合。在一態樣中,R1可為H或C1-C3烷基。在一態樣中,n可為1或0。舉例而言,n可為0。在一態樣中,R3可為C1-C3烷基。在一態樣中,U可為-C(R2)2、-O-或-S-。每一R2可個別地為H或C1-C3烷基。
在另一態樣中,上述式及/或中之每一者可各自獨立地代
表下列中之一或多者:
或其組合。在一態樣中,m可為1或0。在一態樣中,R2可為C1-C3烷基,例如C2烷基。
在另一態樣中,在所有上述式中,每一可獨立地代表下列中之一或多者:或其組合。在一態樣中,Rn可為C1-C3烷基,例如C2烷基。
在另一態樣中,在所有上述式中,每一可獨立地代表下列中之一或多者:
或其組合。Bn係B1、B2及/或B3之通用計法。在一態樣中,Rn可為C1-C3烷基,例如C2烷基。Bn可存在或不存在。
在另一態樣中,在所有上述式中,可代表下列中之一或多者:
或其組合。在一態樣中,b可為-O-、-S-、-N(R1)-或-C(R1)2-。在一態樣中,每一R1可個別地為H或C1-C3烷基,例如C2烷基。舉例而言,b可為-O-、-S-或-N(C2H5)-。
在另一態樣中,在所有上述式中,及
中之每一者各自代表下列中之一或多者:
或其組合。舉例而言,及可個別地為
在另一態樣中,在所有上述式中,可為下列中之任一者:
在一態樣中,R1、R2、R3、R4、R5、R6、R7、R8、R9及R10可個別地為H或C1-C3烷基,例如C2烷基。在一態樣中,R1、R2、R3、R4、R5、R6、R7、R8、R9及R10可個別地為H。在一態樣中,U可為-C(R2)2、-O-或-S-。每一R2可個別地為H或C1-C3烷基。
在其他態樣中,發明性組合物可包括下列具體實例中之任一者或多者:
或其組合。
應理解,本文所列舉之具體實例性組合物意欲具有實例性且並不加以限制。在另一態樣中,本發明可排除或不包含本文所列舉化合物中之任一者或多者。舉例而言,在一態樣中,本發明並不包括下列錯合物:
本揭示內容之發明性組合物可用於各種應用,例如,發光裝置。在一特定態樣中,錯合物中之一或多者可為用作用於有機發光顯示器裝置之發光體。
本發明化合物可用於各種應用中。作為發光材料,該等
化合物可為用於有機發光二極體(OLED)、發光裝置及顯示器及其他發光裝置或(作為發光標記物)生物應用中。
可藉由改變環繞金屬中心之配體之結構來調整化合物之發射(及吸收)特徵。舉例而言,配體具有吸電子取代基之化合物通常展現與配體具有供電子取代基之化合物不同之光學性質,包含發射及吸收。通常,化學結構變化會影響化合物之電子結構,此由此影響化合物之吸收及發射。因此,可根據期望特定發射或吸收特性之具體應用來修整或調整本發明化合物。
在另一態樣中,可將本揭示內容之組合物中之任一者之發射光譜調整至期望及/或特定光譜。在另一態樣中,本文所揭示之錯合物可提供窄頻寬,從而使得其能夠用於(例如)寬光譜發光體並不適宜之應用中。
在一態樣中,可藉由以下圖式來闡述錯合物之激發態動力學:
其中3LC代表以配體為中心之三重態之能量,1MLCT代表金屬至配體電荷轉移單重態之能量,T1代表發射三重態之
能量,S0代表基態之能量,且△E代表1MLCT與3LC之間之能量差。
在又另一態樣中,利用不同發射部分及連接基團之膨脹應提供覆蓋寬範圍可見光譜之窄發射錯合物。可藉由修改發射片段之以配體為中心之三重態(3LC)來調整某一錯合物之發射能量。此可經由修改發射片段之供給或接收部分之能量之結構變化來達成。
在另一態樣中,可藉由修改錯合物之輔助部分(L^X)經由改變環金屬化部分、連接部分或二者來控制1MLCT轉變之性質。
在一態樣中,發明性組合物適用作用於全彩顯示器應用中之發光體。在此一態樣中,環金屬化配體之幾何結構可為剛性。此剛性可使得在基態與激發態之間具有類似幾何結構,從而得到由自激發態中之最低振動能級至基態中之最低振動能級之轉變控制的窄發射光譜。
在另一態樣中,錯合物可經設計以獨立地調整以發射片段為中心之3LC態及金屬至輔助配體1MLCT態之值。減小該等狀態之間之能量差(△E)將改良其間之混合,改良放射衰變速率,並阻抑自發射態(T1)至基態(S0)中之激發振動能級發生之轉變。因此,可減少發射光譜之振動肩峰(vibrational shoulder),從而得到更窄之發射特徵。
在另一態樣中,一個金屬中心具有四個配體之分子結構可為較佳。在此一態樣中,四配體配位結構可至少部分地確保錯合物在(例如)彩色顯示器裝置之製造及操作期間之
電化學及/或光物理學穩定性。
在另一態樣中,與習用材料相比,發明性組合物可在發光裝置(例如,有機發光裝置,例如OLED)中提供改良之效率及/或操作壽命。因此,本文亦揭示包括本文所闡述之錯合物之裝置。磷光發射錯合物(例如彼等闡述於本文中者)之一種應用係全彩顯示器。用於此一顯示器之工業標準需要適於發射特定顏色(稱為「飽和」顏色)之像素。特定而言,該等標準需要飽和紅色、綠色及藍色像素。可使用業內熟知之CIE坐標來量測顏色。
在其他各種態樣中,發明性組合物可為用作(例如)發光標記、用於有機發光二極體、發光應用之發光體及其組合。
可使用各種方法製備本發明化合物,包含但不限於彼等列舉於本文所提供之實例中者。在其他態樣中,在掌握本揭示內容後,熟習此項技術者可易於確定製備如本文所列舉之銥錯合物之適當方法。
提出下列實例以為彼等熟習此項技術者提供完整揭示內容及如何製備及評價本文所主張化合物、組合物、物件、裝置及/或方法之說明,且純粹意欲為本發明之實例且並非意欲限制發明者所認為其發明之範圍。已經努力確保數值(例如量、溫度等)之精確性,但應計及一些誤差及偏差。除非另有說明,否則份數係重量份數,溫度係以℃表示或為環境溫度,且壓力為大氣壓力或接近大氣壓力。
4'-溴-2-硝基聯苯:在氮氣氛下,將20 mL水加熱至60℃且添加125 mmol 2-硝基聯苯并攪拌30分鐘,然後添加6.3 mmol三氯化鐵並進一步攪拌30分鐘。經40分鐘逐滴添加140 mmol溴並攪拌過夜,然後設定至回流下保持4小時。在冷卻之後,藉由使用硫酸氫鈉溶液洗滌來去除殘餘溴。然後使用水將有機殘餘物洗滌兩次,使用濃氫氧化鈉洗滌兩次,且然後使用水洗滌兩次。分離有機部分並溶於二氯甲烷中,然後使用硫酸鎂亁燥。在減壓下濃縮溶液,使用二氯甲烷作為洗脫劑實施二氧化矽之急驟管柱層析,並在減壓下再次濃縮。藉由在甲醇中重結晶來收集4'-溴-2-硝基聯苯,產率為50%。
2-溴-9H-咔唑:在氮氣氛下,將100 mmol 4'-溴-2-硝基聯苯在攪拌之亞磷酸三乙酯中設定於回流下過夜。在冷卻之後,蒸餾掉亞磷酸三乙酯且藉由在甲醇中重結晶來分離2-溴-9H-咔唑,並藉由梯度昇華進一步純化,所得產率為65%。
2-溴-9-(吡啶-2-基)-9H-咔唑:在氮氣氛下,在攪拌之脫氣二甲基亞碸中合併10 mmol 2-溴-9H-咔唑、15 mmol 2-溴吡啶、1 mmol碘化亞銅(I)、25 mmol碳酸鉀及2 mmol L-脯胺酸。將混合物加熱至90℃保持3天,然後冷卻並在二氯甲烷與水之間分離。使用二氯甲烷將水層洗滌兩次且合併有機物並使用鹽水洗滌一次。使用硫酸鎂亁燥有機部分並在減壓下濃縮,且使用二氯甲烷作為洗脫劑實施二氧化矽之管柱層析。在減壓下濃縮之後,分離出2-溴-9-(吡啶-2-基)-9H-咔唑,產率為70%。
2-溴-9-(四氫-2H-吡喃-2-基)-9H-咔唑:將10 mmol 2-溴-9H-咔唑、0.1 mmol甲苯-4-磺酸吡啶鎓及50 mmol 3,4-二氫-2H-吡喃在室溫下添加至二氯甲烷中並攪拌2小時,然後將溫度升至50℃進一步保持2小時。冷卻溶液,在減壓下濃縮,並使用二氯甲烷作為洗脫劑實施二氧化矽之管柱層析。在減壓下濃縮之後,分離出2-溴-9-(四氫-2H-吡喃-2-基)-9H-咔唑,產率為90%。
2-(1H-吡唑-1-基)-9-(四氫-2H-吡喃-2-基)-9H-咔唑:在氮氣氛下,在25 mL攪拌之脫氣二甲基亞碸中合併10 mmol2-溴-9-(四氫-2H-吡喃-2-基)-9H-咔唑、15 mmol吡唑、1 mmol碘化亞銅(I)、25 mmol碳酸鉀及2 mmol L-脯胺酸。將混合物加熱至90℃保持3天,然後冷卻並在二氯甲烷與水之間分離。使用二氯甲烷將水層洗滌兩次且合併有機物並使用鹽水洗滌一次。使用硫酸鎂亁燥有機部分並在減壓下濃縮,且使用二氯甲烷作為洗脫劑實施二氧化矽之管柱層析。在減壓下濃縮之後,分離出2-(1H-吡唑-1-基)-9-(四氫-2H-吡喃-2-基)-9H-咔唑,產率為40%。
2-(1H-吡唑-1-基)-9H-咔唑:將5 mmol 2-(1H-吡唑-1-基)-9-(四氫-2H-吡喃-2-基)-9H-咔唑溶於100 mL甲醇中,然後緩慢添加25 mmol甲基磺酸。將溶液在室溫下攪拌2小時,然後在50℃下進一步攪拌2小時。冷卻反應液,使用碳酸氫鈉驟冷,並在二氯甲烷與水之間分離。使用二氯甲烷將水層洗滌兩次,合併有機部分並使用鹽水洗滌一次。然後使用硫酸鎂亁燥有機部分,過濾,並在減壓下濃縮濾液。使用二氧化矽及二氯甲烷/乙酸乙酯(作為洗脫劑)對所
得固體實施管柱層析。在減壓下濃縮之後,分離出2-(1H-吡唑-1-基)-9H-咔唑,產率為90%。
2'-(1H-吡唑-1-基)-9-(吡啶-2-基)-9H-2,9'-二咔唑:在氮氣氛下,在攪拌之脫氣二甲基亞碸中合併10 mmol 2-(1H-吡唑-1-基)-9H-咔唑、10 mmol 2-溴-9-(吡啶-2-基)-9H-咔唑、1 mmol碘化亞銅(I)、25 mmol碳酸鉀及2 mmol L-脯胺酸。將混合物加熱至90℃保持3天,然後冷卻並在二氯甲烷與水之間分離。使用二氯甲烷將水層洗滌兩次且合併有機物並使用鹽水洗滌一次。使用硫酸鎂亁燥有機部分並在減壓下濃縮,且使用二氯甲烷/乙酸乙酯作為洗脫劑實施二氧化矽之管柱層析。在減壓下濃縮之後,分離出2'-(1H-吡唑-1-基)-9-(吡啶-2-基)-9H-2,9'-二咔唑,產率為60%。
[2'-(1H-吡唑-1-基)-9-(吡啶-2-基)-9H-2,9'-二咔唑]Pt(II),PtN1N:在氮氣氛下,將10 mmol 2'-(1H-吡唑-1-基)-9-(吡啶-2-基)-9H-2,9'-二咔唑、9 mmol K2PtCl4,及4Å分子篩添加至攪拌之乙酸中。將混合物加熱至120℃保持3天。冷卻溶液,並傾倒至100 mL攪拌之二氯甲烷中。過濾混合物,並在減壓下濃縮濾液。使用二氯甲烷作為洗脫劑對發射性固體實施二氧化矽之急驟層析。
圖1圖解說明根據本揭示內容之各種態樣化合物Pt-N1N(插圖)在77K及室溫下之發射光譜。
圖2圖解說明根據本揭示內容之各種態樣化合物Pt-N1N、Pt-N2N及Pt-N3N(插圖)之室溫發射光譜。
Claims (23)
- 一種組合物,其由以下通式代表:
- 如請求項1之組合物,其中該組合物並非
- 如請求項1之組合物,其中該組合物具有下式:
- 一種組合物,其具有下式:
- 如請求項3之組合物,其中係吡啶、異喹啉、甲基咪唑或;係苯基;係吡啶或苯基;係苯基或吡啶;係苯基;且不存在。
- 如請求項3之組合物,其中係吡啶、異喹啉、甲基咪唑或;係苯基;係吡啶或苯基;係苯基或吡啶;係苯基;且係苯基。
- 如請求項1之組合物,其中該組合物具有下式:
- 一種組合物,其具有下式:
- 如請求項7之組合物,其中係異喹啉、甲基咪唑或;係苯基;係吡啶或苯基;係苯基或吡啶;係苯基;且不存在。
- 如請求項7之組合物,其中係異喹啉、甲基咪唑或;係苯基;係吡啶或苯基;係苯基或吡啶;係苯基;且 係苯基。
- 如請求項1之組合物,其中該組合物具有下式:
- 一種組合物,其具有下式:
- 如請求項11之組合物,其中W係Cl、腈、苯基、萘基或異喹啉;係異喹啉、甲基咪唑或;係苯基;係吡啶;且不存在。
- 如請求項11之組合物,其中W係Cl、腈、苯基、萘基或異喹啉;係異喹啉、甲基咪唑或;係苯基;係吡啶;且係苯基。
- 如請求項1之組合物,其中M包括鉑(II)。
- 如請求項1之組合物,其中M包括鈀(II)。
- 如請求項1之組合物,其包括
- 如請求項1之組合物,其包括:
- 如請求項1之組合物,其包括:
- 如請求項1之組合物,其包括:
- 如請求項1之組合物,其包括:
- 如請求項1之組合物,其包括:
- 如請求項1之組合物,其包括:
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Also Published As
Publication number | Publication date |
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US20120302753A1 (en) | 2012-11-29 |
TWI618711B (zh) | 2018-03-21 |
TW201710277A (zh) | 2017-03-16 |
WO2012162488A1 (en) | 2012-11-29 |
US9238668B2 (en) | 2016-01-19 |
US10804476B2 (en) | 2020-10-13 |
US11121328B2 (en) | 2021-09-14 |
US20200403167A1 (en) | 2020-12-24 |
US20160197291A1 (en) | 2016-07-07 |
US20170373260A1 (en) | 2017-12-28 |
TWI551606B (zh) | 2016-10-01 |
US9698359B2 (en) | 2017-07-04 |
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