TWI743556B - 有機發射層及包含其之有機發光裝置 - Google Patents
有機發射層及包含其之有機發光裝置 Download PDFInfo
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- TWI743556B TWI743556B TW108131926A TW108131926A TWI743556B TW I743556 B TWI743556 B TW I743556B TW 108131926 A TW108131926 A TW 108131926A TW 108131926 A TW108131926 A TW 108131926A TW I743556 B TWI743556 B TW I743556B
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- 150000001875 compounds Chemical class 0.000 claims abstract description 110
- 239000003446 ligand Substances 0.000 claims abstract description 92
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 65
- 125000003118 aryl group Chemical group 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- 125000005842 heteroatom Chemical group 0.000 claims description 20
- 229910052741 iridium Inorganic materials 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 239000011368 organic material Substances 0.000 claims description 15
- 125000001153 fluoro group Chemical group F* 0.000 claims description 14
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 229920006395 saturated elastomer Polymers 0.000 claims description 14
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 12
- 229910052701 rubidium Inorganic materials 0.000 claims description 10
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 125000002883 imidazolyl group Chemical group 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical group N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 2
- 229910052751 metal Inorganic materials 0.000 abstract description 50
- 239000002184 metal Substances 0.000 abstract description 49
- SHWNDUJCIYUZRF-UHFFFAOYSA-N imidazo[1,2-f]phenanthridine Chemical compound C1=CC=C2N3C=CN=C3C3=CC=CC=C3C2=C1 SHWNDUJCIYUZRF-UHFFFAOYSA-N 0.000 abstract description 4
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 199
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 194
- 239000010410 layer Substances 0.000 description 160
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 138
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 129
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 118
- 239000000203 mixture Substances 0.000 description 111
- 239000011541 reaction mixture Substances 0.000 description 104
- 239000000463 material Substances 0.000 description 95
- 239000007787 solid Substances 0.000 description 89
- 239000000047 product Substances 0.000 description 88
- 239000000243 solution Substances 0.000 description 80
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 76
- 239000000741 silica gel Substances 0.000 description 74
- 229910002027 silica gel Inorganic materials 0.000 description 74
- 239000000460 chlorine Substances 0.000 description 73
- 235000019439 ethyl acetate Nutrition 0.000 description 69
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 66
- -1 N-methyl-2-phenylimidazole Iridium(III) complexes Chemical class 0.000 description 59
- 238000006243 chemical reaction Methods 0.000 description 59
- 238000002360 preparation method Methods 0.000 description 58
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 56
- 238000005481 NMR spectroscopy Methods 0.000 description 51
- 238000010992 reflux Methods 0.000 description 51
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 50
- 239000012299 nitrogen atmosphere Substances 0.000 description 49
- 239000002904 solvent Substances 0.000 description 48
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 230000015572 biosynthetic process Effects 0.000 description 45
- 238000001816 cooling Methods 0.000 description 45
- 238000003786 synthesis reaction Methods 0.000 description 45
- 229910052757 nitrogen Inorganic materials 0.000 description 42
- UVUNZHNCNUFPQA-UHFFFAOYSA-K C(C)(=O)CC(C(=O)[O-])=O.[Ir+3].C(C)(=O)CC(C(=O)[O-])=O.C(C)(=O)CC(C(=O)[O-])=O Chemical compound C(C)(=O)CC(C(=O)[O-])=O.[Ir+3].C(C)(=O)CC(C(=O)[O-])=O.C(C)(=O)CC(C(=O)[O-])=O UVUNZHNCNUFPQA-UHFFFAOYSA-K 0.000 description 41
- 238000000034 method Methods 0.000 description 38
- 239000004576 sand Substances 0.000 description 37
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 34
- IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical compound CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 34
- 241000208340 Araliaceae Species 0.000 description 33
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 33
- 235000003140 Panax quinquefolius Nutrition 0.000 description 33
- 235000008434 ginseng Nutrition 0.000 description 33
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- 239000003480 eluent Substances 0.000 description 32
- 239000012044 organic layer Substances 0.000 description 32
- 238000002347 injection Methods 0.000 description 30
- 239000007924 injection Substances 0.000 description 30
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 29
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
- 238000004440 column chromatography Methods 0.000 description 28
- 239000000758 substrate Substances 0.000 description 28
- 230000032258 transport Effects 0.000 description 26
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 25
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 24
- 239000012043 crude product Substances 0.000 description 21
- 239000000706 filtrate Substances 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- 230000005525 hole transport Effects 0.000 description 20
- 238000003756 stirring Methods 0.000 description 20
- 239000002019 doping agent Substances 0.000 description 19
- 150000003384 small molecules Chemical class 0.000 description 19
- 238000001228 spectrum Methods 0.000 description 19
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical group COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 18
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
- 239000003921 oil Substances 0.000 description 17
- 235000019198 oils Nutrition 0.000 description 17
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 17
- 235000017557 sodium bicarbonate Nutrition 0.000 description 17
- 229910052938 sodium sulfate Inorganic materials 0.000 description 17
- 235000011152 sodium sulphate Nutrition 0.000 description 17
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 16
- 125000001424 substituent group Chemical group 0.000 description 16
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 16
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
- 235000019341 magnesium sulphate Nutrition 0.000 description 14
- 230000000903 blocking effect Effects 0.000 description 13
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 13
- 238000004128 high performance liquid chromatography Methods 0.000 description 13
- 239000002244 precipitate Substances 0.000 description 13
- 239000012267 brine Substances 0.000 description 12
- 125000004093 cyano group Chemical group *C#N 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- 239000011241 protective layer Substances 0.000 description 12
- 238000000746 purification Methods 0.000 description 12
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 238000004770 highest occupied molecular orbital Methods 0.000 description 11
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- 238000010898 silica gel chromatography Methods 0.000 description 10
- 229940062627 tribasic potassium phosphate Drugs 0.000 description 10
- 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 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 150000001409 amidines Chemical class 0.000 description 8
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-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
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 8
- 238000002390 rotary evaporation Methods 0.000 description 8
- 238000000859 sublimation Methods 0.000 description 8
- 230000008022 sublimation Effects 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- QSKPIOLLBIHNAC-UHFFFAOYSA-N 2-chloro-acetaldehyde Chemical compound ClCC=O QSKPIOLLBIHNAC-UHFFFAOYSA-N 0.000 description 7
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 238000006069 Suzuki reaction reaction Methods 0.000 description 7
- 229960000583 acetic acid Drugs 0.000 description 7
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- 238000000151 deposition Methods 0.000 description 7
- 238000001514 detection method Methods 0.000 description 7
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 7
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 7
- 230000005281 excited state Effects 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 7
- 238000004949 mass spectrometry Methods 0.000 description 7
- 230000007246 mechanism Effects 0.000 description 7
- 125000002524 organometallic group Chemical group 0.000 description 7
- 229910052763 palladium Inorganic materials 0.000 description 7
- 238000006467 substitution reaction Methods 0.000 description 7
- BKWJLGMUFMNPBF-UHFFFAOYSA-N 2-bromo-2-(2,6-dimethylphenyl)acetaldehyde Chemical compound CC1=CC=CC(C)=C1C(Br)C=O BKWJLGMUFMNPBF-UHFFFAOYSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- UNRQTHVKJQUDDF-UHFFFAOYSA-N acetylpyruvic acid Chemical compound CC(=O)CC(=O)C(O)=O UNRQTHVKJQUDDF-UHFFFAOYSA-N 0.000 description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 239000002131 composite material Substances 0.000 description 6
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 6
- 239000000412 dendrimer Substances 0.000 description 6
- 229920000736 dendritic polymer Polymers 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 6
- 230000005693 optoelectronics Effects 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- 229910052697 platinum Inorganic materials 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 230000007704 transition Effects 0.000 description 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 5
- 239000005909 Kieselgur Substances 0.000 description 5
- 229910004298 SiO 2 Inorganic materials 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 239000010406 cathode material Substances 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 125000001072 heteroaryl group Chemical group 0.000 description 5
- HLYTZTFNIRBLNA-LNTINUHCSA-K iridium(3+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ir+3].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O HLYTZTFNIRBLNA-LNTINUHCSA-K 0.000 description 5
- 229910044991 metal oxide Inorganic materials 0.000 description 5
- 150000004706 metal oxides Chemical class 0.000 description 5
- 239000012264 purified product Substances 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 241000894007 species Species 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 238000003828 vacuum filtration Methods 0.000 description 5
- NPLZNDDFVCGRAG-UHFFFAOYSA-N (2-cyanophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1C#N NPLZNDDFVCGRAG-UHFFFAOYSA-N 0.000 description 4
- XGTDDGCFAJPBMT-UHFFFAOYSA-N 10-fluoroimidazo[1,2-f]phenanthridine Chemical compound C1=CC=C2C3=CC(F)=CC=C3C3=NC=CN3C2=C1 XGTDDGCFAJPBMT-UHFFFAOYSA-N 0.000 description 4
- ANDMSCLLFJQZSF-UHFFFAOYSA-N 2-(4H-1,3,2-dioxaborinin-2-yl)benzonitrile Chemical compound O1B(OCC=C1)C1=C(C#N)C=CC=C1 ANDMSCLLFJQZSF-UHFFFAOYSA-N 0.000 description 4
- LNROMBKXXHEUAQ-UHFFFAOYSA-N 2-bromo-4-(2,2-dimethylpropyl)aniline Chemical compound CC(C)(C)CC1=CC=C(N)C(Br)=C1 LNROMBKXXHEUAQ-UHFFFAOYSA-N 0.000 description 4
- QRZMXADUXZADTF-UHFFFAOYSA-N 4-aminoimidazole Chemical compound NC1=CNC=N1 QRZMXADUXZADTF-UHFFFAOYSA-N 0.000 description 4
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 4
- 239000005695 Ammonium acetate Substances 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 235000019257 ammonium acetate Nutrition 0.000 description 4
- 229940043376 ammonium acetate Drugs 0.000 description 4
- 239000010405 anode material Substances 0.000 description 4
- 239000002800 charge carrier Substances 0.000 description 4
- 150000004696 coordination complex Chemical class 0.000 description 4
- WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 4
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000007429 general method Methods 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 150000002503 iridium Chemical class 0.000 description 4
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 239000005416 organic matter Substances 0.000 description 4
- 229910052762 osmium Inorganic materials 0.000 description 4
- UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 4
- CPJSUEIXXCENMM-UHFFFAOYSA-N phenacetin Chemical compound CCOC1=CC=C(NC(C)=O)C=C1 CPJSUEIXXCENMM-UHFFFAOYSA-N 0.000 description 4
- PLOCPSZUSGEEMU-UHFFFAOYSA-N phenanthridin-1-amine Chemical compound C1=CC=CC2=C3C(N)=CC=CC3=NC=C21 PLOCPSZUSGEEMU-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 4
- 238000007539 photo-oxidation reaction Methods 0.000 description 4
- 230000002285 radioactive effect Effects 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- ZXDTWWZIHJEZOG-UHFFFAOYSA-N (2,6-dimethylphenyl)boronic acid Chemical compound CC1=CC=CC(C)=C1B(O)O ZXDTWWZIHJEZOG-UHFFFAOYSA-N 0.000 description 3
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- C—CHEMISTRY; METALLURGY
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- 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
-
- 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
- C07F15/0033—Iridium compounds
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- 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
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- C—CHEMISTRY; METALLURGY
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- 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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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Abstract
本發明係描述包含磷光金屬錯合物之化合物,該錯合物包含環金屬化之咪唑并[1,2-f]啡啶與二咪唑并[1,2-a:1',2'-c]喹唑啉配位體或其等電子或苯并環化類似物。亦描述包含此等化合物之有機發光裝置。
Description
一般而言,本發明係關於有機發光裝置(OLED),與此等裝置中所使用之有機化合物。
利用有機材料之光電子裝置由於多種原因係逐漸地變成一般所期望的。許多用以製造此種裝置之材料係相對較不昂貴,因此有機光電子裝置具有勝過無機裝置之成本利益之潛力。此外,有機材料之固有性質,譬如其撓性,可使得彼等極適合特定應用,譬如在可撓性基材上之製造。有機光電子裝置之實例包括有機發光裝置(OLED)、有機光敏晶體管、有機光生伏打電池及有機光檢測器。對於OLED,有機材料可具有勝過習用材料之性能優點。例如,於有機發射層發射光線下之波長通常可容易地以適當摻雜劑調整。
於本文中使用之"有機物"一詞係包括聚合材料以及小分子有機物質,其可用以製造有機光電子裝置。"小分子"係指不為聚合體之任何有機物質,且"小分子"實際上可相當大。小分子可在一些情況中包含重複單位。例如,使用長鏈烷基作為取代基,不會將分子自"小分子"種類移除。小分子亦可被併入聚合體中,例如作為聚合體主鏈上之懸垂基團,或作為
主鏈之一部份。小分子亦可充作樹枝狀體之核心部份基團,該樹枝狀體係包含一系列被建立在核心部份基團上之化學殼。樹枝狀體之核心部份基團可為螢光或磷光小分子發射體。樹枝狀體可為"小分子",且咸信目前使用於OLED領域中之所有樹枝狀體均為小分子。一般而言,小分子具有定義明確之化學式,具有單一分子量,然而聚合體具有可隨著分子改變之化學式與分子量。於本文中使用之"有機物"係包括烴基與雜原子取代之烴基配位體之金屬錯合物。
OLED係利用有機薄膜,當施加電壓越過該裝置時,其會發射光線。OLED係逐漸變成一種漸增地令人感興趣之技術,供使用於一些應用中,譬如平板顯示器、照明及背光照明。數種OLED材料與型態係被描述於美國專利案號5,844,363、6,303,238及5,707,745中,其係以全文併於本文供參考。
OLED裝置通常(但未必總是)係意欲經過至少一個電極發射光線,且一或多個透明電極可用於有機光電子裝置中。例如,透明電極材料,譬如氧化銦錫(ITO),可作為底部電極使用。透明頂部電極亦可使用,譬如於美國專利案號5,703,436與5,707,745中所揭示者,其係以全文併入供參考。對於意欲僅經過底部電極發射光線之裝置,頂部電極不必為透明,且可包含具有高導電性之厚且反射性金屬層。同樣地,對於意欲僅經過頂部電極發射光線之裝置,底部電極可為不透明及/或反射性。在電極不必為透明之情況下,使用較厚層可提供較佳導電性,而使用反射電極可增加經過其他電極所發射光線之量,其方式是使光線反射返回朝向透明電極。亦可製造完全透明裝置,其中兩個電極均為透明。亦可製造側面發射之OLED,且一或兩個電極在此種裝置中可為不透明或反射性。
於本文中使用之"頂部"係意謂最遠離基板,然而"底部"係意謂最接近基板。例如,關於具有兩個電極之裝置,底部電極為最接近基板之電極,且通常為所製造之第一個電極。底部電極具有兩個表面,最接近基板之底部表面與遠離基板之頂部表面。在第一層係被描述為"經配置於"第二層上方之情況下,第一層係經配置遠離基板。可以有其他層在第一與第二層之間,除非指定第一層係與第二層"物理接觸"。例如,陰極可被描述為"經配置於"陽極上方,即使有各種有機層在其間亦然。
於本文中使用之"溶液可處理"係意謂能夠於液體媒質中溶解、分散或輸送,及/或自其沉積,無論是呈溶液或懸浮液形式。
當於本文中使用,且如熟諳此藝者所一般性地明瞭時,若第一個能階較接近真空能階,則第一個"最高佔有分子軌道"(HOMO)或"最低未佔有分子軌道"(LUMO)能階係"大於"或"高於"第二個HOMO或LUMO能階。由於電離電位(IP)係以相對於真空能階之負能量進行度量,故較高HOMO能階係相應於具有較小絕對值之IP(較不負值之IP)。同樣地,較高LUMO能階係相應於具有較小絕對值之電子親和力(EA)(較不負值之EA)。在習用能階圖上,具有真空能階在頂部,一種材料之LUMO能階係高於相同材料之HOMO能階。"較高"HOMO或LUMO能階係顯示比"較低"HOMO或LUMO能階更接近此種圖之頂部。
長久留存藍色發射磷光摻雜劑之發展係被認為是目前OLED研究與發展之重要未實現目的。雖然具有呈深藍色或接近UV之發射峰之磷光OLED裝置已被証實,但顯示100尼特(nit)最初發光度之藍色發射裝置壽命已為數百小時之譜(其中"壽命"係指在恒定電流下,發光度下降至最初程度之50%之時間)。例如,衍生自N-甲基-2-苯基咪唑之二齒合配位體之
銥(III)錯合物可用以製備藍色OLED裝置,但以此等摻雜劑係發現極短壽命(在100尼特最初發光下為約250小時)。
由於預期大部份商業應用在200尼特最初發光下需要壽命超過10,000小時,故在藍色磷光OLED裝置上之主要改良事項係被尋求。
根據前述目的,吾人係於本文中描述數種新穎種類之磷光金屬錯合物與OLED裝置,其包含環金屬化之咪唑并[1,2-f]啡啶或二咪唑并[1,2-a:1',2'-c]喹唑啉配位體或其等電子或苯并環化類似物,可用於製備長久留存與有效藍色、綠色及紅色發射OLED裝置。許多此等錯合物係具有令人驚訝之狹窄磷光發射線形,或對於此種高度地共軛分子為令人驚訝地高之三重態能量,或兩者。使用G98/B31yp/cep-31g基礎組合之密度功能性理論(DFT)計算,指出本發明之許多藍色發射錯合物係具有相對較小之單態-三重態間隙,低於約0.25eV。不希望被理論所束縛,本發明人認為稠合環之18π電子計數及特定排列係與小單態-三重態帶隙有關聯,且可具有對於光譜線形與裝置壽命之有利作用。小單態-三重態間隙亦可幫助低電壓OLED裝置之設計,且有利地降低包含此種化合物之OLED裝置之功率消耗。
其中n=1,2或3;R1a,R1b,R1c,R1d,R1e,R1f,R1g,R1h及R1i係各獨立
為H、烴基、雜原子取代之烴基、氰基、氟基、OR2a、SR2a、NR2aR2b、BR2aR2b或SiR2aRb2R2c,其中R2a-c係各獨立為烴基或雜原子取代之烴基,且其中R1a-i與R2a-c之任兩個可被連結以形成飽和或不飽和、芳族或非芳族環;而X-Y為輔助配位體。
於一方面,係提供具有式I之銥錯合物,其中R1e為分枝狀烷基,含有至少4個碳原子,且其中分枝係發生在比苄基性位置更遠之位置處。
其中Ra、Rb及Rc係獨立為H、烷基或芳基,且Ra與Rb之至少一個為烷基或芳基。Ra、Rb及Rc可接合以形成稠合環。
於一方面,係提供具有式I之銥錯合物,其中R1a為供電子基團。
本文中所提供之各種發射錯合物,且特別是具有式I之銥錯合物,可被併入有機發光裝置中。此種裝置之發射層可包含除了發射錯合物以外之主體。較佳主體包括含有咔唑基團之有機材料。mCBP為特佳主體。
一般而言,OLED包含至少一個有機層,經配置在陽極與陰極之間,且電連接至彼等。當施加電流時,陽極係注入空穴,而陰極係注入電子至有機層中。被注入之空穴與電子各朝向帶相反電荷之電極潛移。當電子與空穴定位在相同分子上時,係形成"激發子",其係為具有受激能態之定域化電子-空穴對。當激發子鬆弛時,光線係經由光發射機制發射。在一些情況中,激發子可被定位在激元或受激複合分子上。非放射性機制,譬如
熱鬆弛,亦可存在,但一般認為是非所需的。
最初之OLED係使用自其單重態("螢光")發射光線之發射分子,如揭示於例如美國專利4,769,292中者,其係以全文併入供參考。螢光發射通常係發生在小於10毫微秒之時間架構中。
又最近,具有自三重態("磷光")發射光線之發射材料之OLED已被証實。Baldo等人,"自有機電致發光裝置之高度地有效磷光發射",Nature,第395卷,151-154,1998;("Baldo-I")與Baldo等人,"以電致磷光為基礎之極高效率綠色有機發光裝置",Appl.Phys.Lett.,第75卷,第3期,4-6(1999)("Baldo-II"),其係以全文併入供參考。磷光可被稱為"禁忌"轉變,因為此轉變需要在旋轉狀態上改變,且量子力學顯示此種轉變是不利的。因此,磷光通常係發生在超過至少10毫微秒,而典型上大於100毫微秒之時間架構中。若磷光之天然放射壽命太長,則三重態可藉由非放射性機制衰減,以致沒有光線被發射。有機磷光亦經常在極低溫度下被發現於含有具未共用電子對之雜原子之分子中。2,2'-聯吡啶為此種分子。非放射性衰減機制典型上為溫度依存性,以致在液態氮溫度下顯示磷光之有機材料典型上不會在室溫下顯示磷光。但是,正如由Baldo所証實,此項問題可藉由選擇在室溫下確實會發出磷光之磷光化合物尋求解決。代表性發射層包括經摻雜或未經摻雜之磷光有機金屬材料,譬如於美國專利案號6,303,238;6,310,360;6,830,828;及6,835,469;美國專利申請案公報2002-0182441;以及WO-02/074015中所揭示者。
一般而言,咸認在OLED中之激發子會以約3:1之比例產生,意即大約75%三重態與25%單態。參閱Adachi等人,"在有機發光裝置中接近100%內部磷光效率,"J.Appl.Phys.,90,5048(2001),其係以全文併入供
參考。在許多情況中,單重態激發子可容易地經由"系統間過渡"轉移其能量至三重態激發狀態,然而三重態激發子不可容易地轉移其能量至單態激發狀態。因此,100%內部量子效率理論上使用磷光OLED係為可能。在螢光裝置中,三重態激發子之能量通常會喪失至無放射衰減過程,其會使裝置加熱,造成遠為較低之內部量子效率。利用自三重激發狀態發射之磷光材料之OLED係揭示於例如美國專利6,303,238中,其係以全文併入供參考。
磷光之前可為自三重受激態轉變至中間物非三重態,發射衰減係自其發生。例如,經配位至鑭系元素之有機分子係經常自被定位在鑭系金屬上之激發狀態發出磷光。但是,此種材料不會直接地自三重受激態發出磷光,而是替代地自鑭系金屬離子中心之原子受激態發射。二酮酸銪錯合物係說明此等物種類型之一個組群。
得自三重態之磷光可被加強而勝過螢光,其方式是限制,較佳係經過結合緊密接近具高原子序之原子之有機分子。被稱為重原子效應之此種現象係藉由稱為旋轉軌道偶合之機制產生。此種磷光轉變可自有機金屬分子譬如參(2-苯基吡啶)銥(III)之受激金屬對配位體電荷轉移(MLCT)狀態發現。雖然不希望被理論所束縛,但咸信在有機金屬錯合物中之有機金屬對碳鍵係為達成有機分子對高原子序原子之所要接近之尤佳方法。明確言之,就本申請案而論,有機碳-金屬鍵之存在於有機金屬錯合物中可促進較大MLCT特性,其可用於生產高度地有效裝置。
於本文中使用之"三重態能量"一詞係指相應於特定材料磷光光譜中可辨識之最高能量特徵之能量。最高能量特徵未必是磷光光譜上具有最大強度之吸收峰,而可為例如此種吸收峰之高能量側面上清楚肩部之局部最
大值。
於本文中使用之"有機金屬"一詞係如一般熟諳此藝者所大致上明瞭,且如在例如"無機化學"(第2版)Gary L.Miessler與Donald A.Tarr,Prentice Hall(1998)中所示。因此,有機金屬一詞係指具有經過碳-金屬鍵結合至金屬之有機基團之化合物。此種類不包括本身配位化合物,其係為僅具有得自雜原子之供體鍵結之物質,譬如胺類、鹵化物、擬鹵化物(CN等)等之金屬錯合物。實際上,有機金屬化合物,除了一或多個對有機物種之碳-金屬鍵以外,可包含得自雜原子之一或多個供體鍵結。對有機物種之碳-金屬鍵係指在金屬與有機基團(譬如苯基、烷基、烯基等)之碳原子間之直接鍵結,但非指對"無機碳"譬如CN或CO之碳之金屬鍵。
圖1顯示有機發光裝置100。此等圖未必按比例畫出。裝置100可包含基板110、陽極115、空穴注入層120、空穴輸送層125、電子阻斷層130、發射層135、空穴阻斷層140、電子輸送層145、電子注入層150、保護層155及陰極160。陰極160為複合陰極,具有第一個導電層162與第二個導電層164。裝置100可藉由按順序沉積所述之層而製成。
基板110可為提供所要結構性質之任何適當基板。基板110可為可撓性或剛性。基板110可為透明、半透明或不透明。塑膠與玻璃為較佳剛性基板材料之實例。塑膠與金屬箔為較佳可撓性基材之實例。基板110可為半導體材料,以幫助電路系統之製造。例如,基板110可為矽晶圓,電路係於其上製成,能夠控制接著沉積在基板上之OLED。可使用其他基板。基材110之材料與厚度可經選擇,以獲得所要之結構與光學性質。
陽極115可為足夠導電性以輸送空穴至有機層之任何適當陽極。陽極115之材料較佳係具有功函數高於約4eV("高功函數材料")。較佳陽極材
料包括導電性金屬氧化物,譬如氧化銦錫(ITO)與氧化銦鋅(IZO)、氧化鋁鋅(AlZnO)及金屬。陽極115(與基板110)可為足夠透明以產生底部發射裝置。較佳透明基材與陽極組合係為經沉積在玻璃或塑膠(基材)上之市購可得ITO(陽極)。可撓性與透明基材-陽極組合係被揭示於美國專利5,844,363與6,602,540 B2中,其係以全文併入供參考。陽極115可為不透明及/或反射性。反射陽極115對於一些頂部發射裝置可為較佳,以增加自裝置頂部所發射光線之量。陽極115之材料與厚度可經選擇,以獲得所要之導電性與光學性質。在陽極115為透明之情況下,對於足夠厚以提供所要導電性,而足夠薄以提供所要透明程度之特定材料,可以有一範圍之厚度。可使用其他陽極材料與結構。
空穴輸送層125可包含能夠輸送空穴之材料。空穴輸送層130可為固有(未經摻雜)或經摻雜。摻雜作用可用以增強導電性。α-NPD與TPD係為固有空穴輸送層之實例。p-摻雜之空穴輸送層之實例,係為在50:1之莫耳比下,以F4-TCNQ摻雜之m-MTDATA,如在頒予Forrest等人之美國專利申請案公報2003-0230980中所揭示者,其係以全文併入供參考。可使用其他空穴輸送層。
發射層135可包含當電流通過陽極115與陰極160之間時能夠發射光線之有機材料。發射層135較佳係含有磷光發射材料,惟螢光發射材料亦可使用。磷光材料為較佳,因為與此種材料有關聯之較高發光效率。發射層135亦可包含能夠輸送電子及/或空穴之主體材料,被發射材料摻雜,該發射材料可捕獲電子、空穴及/或激發子,以致激發子係經由光發射機制自發射材料鬆弛。發射層135可包含合併輸送與發射性質之單一材料。不論發射材料為摻雜劑或主要成份,發射層135可包含其他材料,譬如會調整
發射材料之發射之摻雜劑。發射層135可包含能夠以組合發射所要光譜之多種發射材料。磷光發射材料之實例包括Ir(ppy)3。螢光發射材料之實例包括DCM與DMQA。主體材料之實例包括Alq3、CBP及mCP。發射與主體材料之實例係揭示於頒予Thompson等人之美國專利6,303,238中,其係以全文併入供參考。發射材料可以多種方式被加入發射層135中。例如,發射小分子可被併入聚合體中。這可藉由數種方式達成:經由將小分子無論是以個別且不同分子物種摻雜至聚合體中;或經由將小分子併入聚合體之主鏈中,以形成共聚物;或經由將小分子以懸垂基團結合於聚合體上。可使用其他發射層材料與結構。例如,小分子發射材料可以樹枝狀體之核心存在。
許多可使用之發射材料係包含一或多種結合至金屬中心之配位體。若配位體直接有助於有機金屬發射材料之光活性性質,則其可被稱為"光活性"。"光活性"配位體可搭配金屬提供能階,當光子被發射時,電子係自其且對其移動。其他配位體可被稱為"輔助"。輔助配位體可改變分子之光活性性質,例如藉由移轉光活性配位體之能階,但輔助配位體不會直接地提供涉及光線發射之能階。在一個分子中為光活性之配位體,可能在另一個中為輔助。光活性與輔助之此等定義係意欲作為非限制性理論。
電子輸送層145可包含能夠輸送電子之材料。電子輸送層145可為固有(未經摻雜)或經摻雜。摻雜作用可用以增強導電性。Alq3為固有電子輸送層之實例。n-摻雜之電子輸送層之實例,係為在1:1之莫耳比下,以Li摻雜之BPhen,如在頒予Forrest等人之美國專利申請案公報2003-0230980中所揭示者,其係以全文併入供參考。可使用其他電子輸送層。
電子輸送層之帶有電荷成份可經選擇,以致使電子可有效地自陰極
注入至電子輸送層之LUMO(最低未佔有分子軌道)能階中。"帶有電荷成份"係為負責實際上輸送電子之LUMO能階之材料。此成份可為基層材料,或其可為摻雜劑。一般而言,有機材料LUMO能階之特徵可為該材料之電子親和力,且一般而言,陰極之相對電子注入效率,其特徵可以陰極材料之功函數為觀點。這意謂電子輸送層與相鄰陰極之較佳性質可以ETL之帶有電荷成份之電子親和力與陰極材料之功函數為觀點而指定。特定言之,為達成高電子注入效率,陰極材料之功函數較佳係不大於電子輸送層帶有電荷成份之電子親和力達超過約0.75eV,更佳係不超過約0.5eV。類似考量係適用於其中電子正被注入之任何層。
陰極160可為此項技藝已知之任何適當材料或材料之組合,以致陰極160係能夠傳導電子,且將彼等注入裝置100之有機層中。陰極160可為透明或不透明,且可為反射性。金屬與金屬氧化物為適當陰極材料之實例。陰極160可為單層,或可具有複合結構。圖1顯示具有薄金屬層162與較厚導電性金屬氧化物層164之複合陰極160。在複合陰極中,關於較厚層164之較佳材料包括ITO、IZO及此項技藝已知之其他材料。美國專利案號5,703,436, 5,707,745, 6,548,956 B2及6,576,134 B2,其係以全文併入供參考,係揭示陰極之實例,包括複合陰極,具有一個金屬薄層,譬如Mg:Ag,與覆蓋在其上之透明導電性濺射沉積之ITO層。與其下方有機層接觸之陰極160部份,不論其是否為單層陰極160,複合陰極之薄金屬層162或一些其他配件,較佳係由具有功函數低於約4eV之材料("低功函數材料")製成。可使用其他陰極材料與結構。
阻斷層可用以降低離開發射層之電荷載流子(電子或空穴)及/或激發子之數目。電子阻斷層130可經配置在發射層135與空穴輸送層125之間,
以阻斷電子在空穴輸送層125之方向上離開發射層135。同樣地,空穴阻斷層140可經配置在發射層135與電子輸送層145之間,以阻斷空穴在電子輸送層145之方向上離開發射層135。阻斷層亦可用以阻斷激發子擴散離開發射層。阻斷層之理論與用途係更詳細地描述於美國專利案號6,097,147與頒予Forrest等人之美國專利申請案公報2003-0230980中,其係以全文併入供參考。
當於本文中使用時,且如熟諳此藝者所明瞭,"阻斷層"一詞係意謂該層提供會顯著地抑制電荷載流子及/或激發子經過裝置輸送之障壁,而非指出該層必定完全阻斷電荷載流子及/或激發子。當與缺乏阻斷層之類似裝置比較時,此種阻斷層之存在於裝置中可造成實質上較高效率。阻斷層亦可用以限制發射至所要之OLED區域。
一般而言,注入層係包含可改良電荷載流子自一層(譬如電極或有機層)之注入至相鄰有機層中之材料。注入層亦可進行電荷輸送功能。在裝置100中,空穴注入層120可為會改良空穴自陽極115之注入至空穴輸送層125中之任何層。CuPc為可作為空穴注入層使用之材料之實例,自ITO陽極115及其他陽極。在裝置100中,電子注入層150可為會改良電子之注入電子輸送層145中之任何層。LiF/Al為可作為電子注入層使用之材料之實例,自相鄰層至電子輸送層。其他材料或材料之組合可用於注入層。依特定裝置之型態而定,注入層可經配置在不同於裝置100中所示之位置上。注入層之更多實例係提供於頒予Lu等人之美國專利申請案序號09/931,948中,其係以全文併入供參考。空穴注入層可包含溶液沉積之材料,譬如旋轉塗覆聚合體,例如PEDOT:PSS,或其可為蒸氣沉積小分子材料,例如CuPc或MTDATA。
空穴注入層(HIL)可使陽極表面平面化或潤濕,以提供自陽極之有效空穴注入至空穴注入材料中。空穴注入層亦可具有帶有電荷之成份,其具有HOMO(最高佔有分子軌道)能階,其係如藉由其本文所述相對電離電位(IP)能量所定義,有利地與HIL之一個側面上之相鄰陽極層,及HIL之相反側面上之空穴輸送層相配。"帶有電荷成份"為負責實際上輸送空穴之HOMO能階之材料。此成份可為HIL之基層材料,或其可為摻雜劑。使用經摻雜之HIL係允許摻雜劑針對其電性質經選擇,及主體係針對形態學性質經選擇,譬如潤濕、撓性、韌性等。關於HIL材料之較佳性質係致使空穴可有效地自陽極注入HIL材料中。特定言之,HIL之帶有電荷成份較佳係具有IP大於陽極材料之IP不超過約0.7eV。帶有電荷成份更佳係具有IP大於陽極材料不超過約0.5eV。類似考量係適用於空穴正被注入之任何層。HIL材料係進一步與習用空穴輸送材料區別,其典型上係使用於OLED之空穴輸送層中,因為此種HIL材料可具有空穴傳導性實質上低於習用空穴輸送材料之空穴傳導性。本發明HIL之厚度可為足夠厚以幫助使陽極層之表面平面化或潤濕。例如,低達10毫微米之HIL厚度可為極平滑陽極表面所接受。但是,由於陽極表面傾向於極粗糙,故至高50毫微米之HIL厚度在一些情況中可為所想要的。
保護層可用以在後續製程期間保護其下方層。例如,用以製造金屬或金屬氧化物頂部電極之方法可傷害有機層,而保護層可用以降低或消除此種傷害。在裝置100中,保護層155可在陰極160之製造期間降低對其下方有機層之傷害。保護層較佳係具有關於其輸送之載流子(在裝置100中之電子)類型之高載流子遷移率,以致其不會顯著地增加裝置100之操作電壓。CuPc、BCP及各種金屬苯二甲藍素係為可用於保護層中之材料之實
例。可使用其他材料或材料之組合。保護層155之厚度較佳係足夠厚以致對其下方層只有極少或無傷害,此係由於製程係在有機保護層160被沉積後發生所致,然而並非如此厚以致顯著地增加裝置100之操作電壓。保護層155可經摻雜以增加其導電性。例如,CuPc或BCP保護層160可以Li摻雜。保護層之更詳細描述可參閱頒予Lu之美國專利申請案序號09/931,948,其係以全文併入供參考。
圖2顯示倒置之OLED 200。此裝置包含基板210、陰極215、發射層220、空穴輸送層225及陽極230。裝置200可藉由按順序沉積所述之層而製成。由於最常見之OLED型態係具有陰極,經配置於陽極上方,而裝置200係具有陰極215,經配置於陽極230下方,故裝置200可被稱為"倒置"OLED。類似關於裝置100所述之材料可被使用於裝置200之相應層中。圖2係提供一些層如何可自裝置100之結構省略之一項實例。
圖1與2中所示之簡單層合結構係以非限制性實例方式提供,且應明瞭的是,本發明之具體實施例可伴隨著極多種其他結構一起使用。所述之特定材料與結構係為舉例性質,且可使用其他材料與結構。功能性OLED可經由以不同方式合併所述之各種層而達成,或可完全省略一些層,以設計、性能及成本因素為基礎。亦可加入其他未被明確地描述之層。可使用此等經明確描述者以外之材料。雖然本文中所提供之許多實例係描述各種層為包含單一材料,但應明瞭的是,可使用材料之組合,譬如主體與摻雜劑之混合物,或更一般性地為混合物。層亦可具有各種亞層。對本文中各種層所給予之名稱並非意欲成為嚴格限制。例如,在裝置200中,空穴輸送層225係輸送空穴,且注入空穴至發射層220中,而可被描述為空穴輸送層或空穴注入層。於一項具體實施例中,OLED可被描述為具有"有機
層",經配置在陰極與陽極之間。此有機層可包含單層,或可進一步包含多層如所述之不同有機材料,例如關於圖1與2。
未被明確地描述之結構與材料亦可使用,譬如由聚合材料(PLED)所組成之OLED,譬如於Friend等人之美國專利5,247,190中所揭示者,其係以全文併入供參考。作為進一步實例,可使用具有單一有機層之OLED。OLED可經堆積,例如在頒予Forrest等人之美國專利5,707,745中所述者,其係以全文併入供參考。OLED結構可偏離圖1與2中所示之簡單層合結構。例如,基板可包含有角度反射表面,以改良外聯結,譬如在頒予Forrest等人之美國專利6,091,195中所述之平台結構,及/或在頒予Bulovic等人之美國專利5,834,893中所述之凹坑結構,其係以全文併入供參考。
除非另有指明,否則各種具體實施例之任何層可藉任何適當方法沉積。對於有機層,較佳方法包括熱蒸發,噴墨,譬如在美國專利案號6,013,982與6,087,196中所述者,其係以全文併入供參考,有機氣相沉積(OVPD),譬如在頒予Forrest等人之美國專利6,337,102中所述者,其係以全文併入供參考,及藉由有機蒸氣噴射印刷(OVJP)沉積,譬如在美國專利申請案號10/233,470中所述者,其係以全文併入供參考。其他適當沉積方法包括旋轉塗覆及其他溶液為基礎之方法。溶液為基礎之方法較佳係在氮或惰性大氣中進行。對於其他層,較佳方法包括熱蒸發。較佳構圖方法包括經過罩蓋沉積,冷焊,譬如在美國專利案號6,294,398與6,468,819中所述者,其係以全文併入供參考,及與一些沉積方法譬如噴墨與OVJD有關聯之構圖。其他方法亦可使用。欲被沉積之材料可經改質,以使得彼等可與特定沉積方法相容。例如,取代基,譬如烷基與芳基,分枝或未分
枝,且較佳係含有至少3個碳,可被使用於小分子中,以增強其進行溶液處理之能力。可使用具有20個碳或更多個之取代基,而3-20個碳為較佳範圍。具不對稱結構之材料可具有比具對稱性結構者較佳之溶液加工性,因為不對稱材料可具有較低再結晶傾向。樹枝狀體取代基可用以增強小分子進行溶液處理之能力。
於本文中所揭示之分子可在未偏離本發明之範圍下,以多種不同方式取代。例如,取代基可被添加至具有三個二齒合配位體之化合物中,以致於添加該取代基後,一或多個二齒合配位體係被連結在一起,以形成例如四齒合或六齒合配位體。可形成其他此種鏈結。咸信相對於未具有連結之類似化合物,此類型之連結可增加安定性,此係由於此項技藝中所一般明瞭為"螯合作用"者所致。
根據本發明具體實施例所製造之裝置可被併入極多種消費產品中,包括平板顯示器、電腦監視器、電視、廣告牌、用於內部或外部照明及/或發出信號之光線、頭上顯示器、完全透明顯示器、可撓性顯示器、雷射印表機、電話、手機、個人數字輔助器(PDA)、膝上型電腦、數位照像機、攝像機-錄像機組合裝置、取景器、顯微顯示器、交通工具、大面積壁、電影院或體育館螢幕或標誌。各種控制機制可用以控制根據本發明所製造之裝置,包括被動基質與主動基質。許多裝置係欲供使用於對人類舒適之溫度範圍內,譬如18℃至30℃,而更佳係在室溫(20-25℃)下。
本文中所述之材料與結構可具有OLED以外裝置上之應用。例如,其他光電裝置,譬如有機太陽能電池與有機光檢測器,可採用此材料與結構。更一般而言,有機裝置,譬如有機電晶體,可採用此材料與結構。
"芳基"一詞係指芳族碳環狀單基團。除非另有指明,否則芳族碳環
狀單基團可為經取代或未經取代。取代基可為F、烴基、雜原子取代之烴基、氰基等。
"烴基"係意謂單價或二價、線性、分枝狀或環狀基團,其僅含有碳與氫原子。單價烴基之實例包括下列:C1-C20烷基;被一或多個選自C1-C20烷基、C3-C8環烷基及芳基之基團取代之C1-C20烷基;C3-C8環烷基;被一或多個選自C1-C20烷基、C3-C8環烷基及芳基之基團取代之C3-C8環烷基;C6-C18芳基;及被一或多個選自C1-C20烷基、C3-C8環烷基及芳基之基團取代之C6-C18芳基。二價(橋接)烴基之實例包括:-CH2-;-CH2CH2-;-CH2CH2CH2-;及1,2-次苯基。
"雜原子"係指碳或氫以外之原子。雜原子之實例包括氧、氮、磷、硫、硒、砷、氯、溴、矽及氟。
"雜芳基"係指為芳族之雜環族單基團。除非另有指明,否則芳族雜環狀單基團可為經取代或未經取代。取代基可為F、烴基、雜原子取代之烴基、氰基等。雜芳基之實例包括1-吡咯基、2-吡咯基、3-吡咯基、呋喃基、噻吩基、茚基、咪唑基、唑基、異唑基、咔唑基、噻唑基、嘧啶基、吡啶基、嗒基、吡基、苯并噻吩基等,及其經取代之衍生物。
所謂"鄰位",吾人係意指在芳基或雜芳基上之位置,其係鄰近第二個環對第一個環之連接點。在六員環之情況中,經由1-位置連接之芳基,譬如2,6-二甲基苯基,2-與6-位置係為鄰位。在5-員環之情況中,經由1-位置連接之雜芳基,譬如2,5-二苯基吡咯-1-基,2-與5-位置為鄰位。在本發明之內文中,在鄰近連接點之碳上之環稠合,如在2,3,4,5,7,8,9,10-八氫蒽-1-基中,係被認為是一種類型之鄰位取代。
因此,於第一方面,本發明係關於包含磷光金屬錯合物之化合物,
該錯合物係包含選自第1組之單陰離子性二齒合配位體,其中金屬係選自包括具有原子序大於40之非放射性金屬,且其中二齒合配位體可與其他配位體連結,以包含三齒合、四齒合、五齒合或六齒合配位體;
其中:E1a-q係選自包括C與N,且共同地包含18π-電子系統;其條件是E1a與E1p為不同;且R1a-i係各獨立為H、烴基、雜原子取代之烴基、氰基、氟基、OR2a、SR2a、NR2aR2b、BR2aR2b或SiR2aR2bR2c,其中R2a-c係各獨立為烴基或雜原子取代之烴基,且其中R1a-i與R2a-c之任兩個可被連結以形成飽和或不飽和、芳族或非芳族環;其條件是當連接至N時,R1a-i不為H。
其中:R1a-i係各獨立為H、烴基、雜原子取代之烴基、氰基、氟基、
OR2a、SR2a、NR2aR2b、BR2aR2b或SiR2aR2bR2c,其中R2a-c係各獨立為烴基或雜原子取代之烴基,且其中R1a-i與R2a-c之任兩個可被連結以形成飽和或不飽和、芳族或非芳族環。
在第二項較佳具體實施例中,金屬為Ir或Pt,且二齒合配位體係選自第2組。在第三項較佳具體實施例中,金屬錯合物為選自第2組之配位體之同配位體(homoleptic)Ir錯合物。在第四項較佳具體實施例中,金屬錯合物為異配位體(heteroleptic)Ir錯合物,其係包含兩種選自第2組之二齒合配位體,及第三種單陰離子性二齒合配位體,較佳為乙醯基丙酮酸鹽或經取代之乙醯基丙酮酸鹽。在第五項較佳具體實施例中,金屬係選自包括Re、Ru、Os、Rh、Ir、Pd、Pt、Cu及Au,且R1a-i之至少一個為2,6-二-取代之芳基。在第六項較佳具體實施例中,金屬係選自包括Ir與Pt,配位體係具有式gs1-1,且R1b為2,6-二-取代之芳基,較佳係選自包括2,6-二甲基苯基;2,4,6-三甲基苯基;2,6-二-異丙基苯基;2,4,6-三異丙基苯基;2,6-二-異丙基-4-苯基苯基;2,6-二甲基-4-苯基苯基;2,6-二甲基-4-(2,6-二甲基吡啶-4-基)苯基;2,6-二苯基苯基;2,6-二苯基-4-異丙基苯基;2,4,6-三苯基苯基;2,6-二-異丙基-4-(4-異丙基苯基);2,6-二-異丙基-4-(3,5-二甲基苯基)苯基;2,6-二甲基-4-(2,6-二甲基吡啶-4-基)苯基;2,6-二-異丙基-4-(吡啶-4-基)苯基;及2,6-二-(3,5-二甲基苯基)苯基。
於第三方面,本發明係關於包含第一或第二方面之任何化合物之OLED裝置。
於第四方面,本發明係關於包含磷光金屬錯合物之化合物,該錯合
物係包含選自第4組之單陰離子性二齒合配位體,其中金屬係選自包括具有原子序大於40之非放射性金屬,且其中二齒合配位體可與其他配位體連結,以包含三齒合、四齒合、五齒合或六齒合配位體;
其中:E1a-q係各獨立選自包括C與N,且共同地包含18π-電子系統;其條件是E1a與E1p為不同;且R1a-i係各獨立為H、烴基、雜原子取代之烴基、氰基、氟基、OR2a、SR2a、NR2aR2b、BR2aR2b或SiR2aR2bR2c,其中R2a-c係各獨立為烴基或雜原子取代之烴基,且其中R1a-i與R2a-c之任兩個可被連結以形成飽和或不飽和、芳族或非芳族環;其條件是當連接至N時,R1a-i不為H。
其中:R1a-i係各獨立為H、烴基、雜原子取代之烴基、氰基、氟基、OR2a、SR2a、NR2aR2b、BR2aR2b或SiR2aR2bR2c,其中R2a-c係各獨立為烴基或雜原子取代之烴基,且其中R1a-i與R2a-c之任兩個可被連結以形成環。
其中:R1a-i係各獨立為H、烴基、雜原子取代之烴基、氰基、氟基、OR2a、SR2a、NR2aR2b、BR2aR2b或SiR2aR2bR2c,其中R2a-c係各獨立為烴基或雜原子取代之烴基,且其中R1a-i與R2a-c之任兩個可被連結以形成環。
在第四方面之第三項較佳具體實施例中,二齒合配位體係被一或多個2,6-二取代之芳基或雜芳基取代,取代基較佳係選自包括2,6-二甲基苯基;2,4,6-三甲基苯基;2,6-二-異丙基苯基;2,4,6-三異丙基苯基;2,6-二-異丙基-4-苯基苯基;2,6-二甲基-4-苯基苯基;2,6-二甲基-4-(2,6-二甲基吡啶-4-基)苯基;2,6-二苯基苯基;2,6-二苯基-4-異丙基苯基;2,4,6-三苯基苯基;2,6-二-異丙基-4-(4-異丙基苯基);2,6-二-異丙基-4-(3,5-二甲基苯基)苯基;2,6-二甲基-4-(2,6-二甲基吡啶-4-基)苯基;2,6-二-異丙基-4-(吡啶-4-基)苯基;及2,6-二-(3,5-二甲基苯基)苯基。
在第四方面之第四項較佳具體實施例中,金屬係選自包括Re、Ru、Os、Rh、Ir、Pd、Pt、Cu及Au,且更佳係選自包括Os、Ir及Pt,而最佳為Ir。
於第五方面,本發明係關於包含第四方面之化合物之OLED裝置。
於第六方面,本發明係關於相應於第四方面之配位體之化合物,其中金屬已被H取代。
於第七方面,本發明係關於包含磷光金屬錯合物之化合物,該錯合物係包含選自第7組之單陰離子性二齒合配位體,其中金屬係選自包括具有原子序大於40之非放射性金屬,且其中二齒合配位體係包含碳烯供體,且可與其他配位體連結,以包含三齒合、四齒合、五齒合或六齒合配位體;
其中:E1a-q係選自包括C與N,且共同地包含18π-電子系統;其條件是E1a與E1p均為碳;且R1a-i係各獨立為H、烴基、雜原子取代之烴基、氰基、氟基、OR2a、SR2a、NR2aR2b、BR2aR2b或SiR2aR2bR2c,其中R2a-c係各獨立為烴基或雜原子取代之烴基,且其中R1a-i與R2a-c之任兩個可被連結以形成飽和或不飽和、芳族或非芳族環;其條件是當連接至N時,R1a-i不為H。
其中:
R1a-i係各獨立為H、烴基、雜原子取代之烴基、氰基、氟基、OR2a、SR2a、NR2aR2b、BR2aR2b或SiR2aR2bR2c,其中R2a-c係各獨立為烴基或雜原子取代之烴基,且其中R1a-i與R2a-c之任兩個可被連結以形成飽和或不飽和、芳族或非芳族環;其條件是當連接至N時,R1a-i不為H。
於第八方面,本發明係關於包含第七方面之化合物之OLED裝置。
於第九方面,本發明係關於包含磷光金屬錯合物之化合物,該錯合物係包含選自第9組之單陰離子性二齒合配位體,其中金屬係選自包括具有原子序大於40之非放射性金屬,且其中二齒合配位體係包含碳烯供體,且可與其他配位體連結,以包含三齒合、四齒合、五齒合或六齒合配位體;
其中:E1a-q係選自包括C與N,且共同地包含18π-電子系統;其條件是E1a與E1p均為碳;且R1a-i係各獨立為H、烴基、雜原子取代之烴基、氰基、氟基、OR2a、SR2a、NR2aR2b、BR2aR2b或SiR2aR2bR2c,其中R2a-c係各獨立為烴基或雜原子取代之烴基,且其中R1a-i與R2a-c之任兩個可被連結以形成飽和或不飽和、芳族或非芳族環;其條件是當連接至N時,R1a-i不為H。
其中:R1a-i係各獨立為H、烴基、雜原子取代之烴基、氰基、氟基、OR2a、SR2a、NR2aR2b、BR2aR2b或SiR2aR2bR2c,其中R2a-c係各獨立為烴基或雜原子取代之烴基,且其中R1a-i與R2a-c之任兩個可被連結以形成飽和或不飽和、芳族或非芳族環;其條件是當連接至N時,R1a-i不為H。
於第十方面,本發明係關於包含第九方面之化合物之OLED裝置。
於第十一方面,本發明係關於包含磷光金屬錯合物之化合物,該錯合物係包含選自第11組之單陰離子性二齒合配位體,其中金屬係選自包括具有原子序大於40之非放射性金屬,且其中二齒合配位體可與其他配位體連結,以包含三齒合、四齒合、五齒合或六齒合配位體;
其中:R1a-i係各獨立為H、烴基、雜原子取代之烴基、氰基、氟基、OR2a、SR2a、NR2aR2b、BR2aR2b或SiR2aR2bR2c,其中R2a-c係各獨立為烴基或雜原子取代之烴基,且其中R1a-i與R2a-c之任兩個可被連結以形成飽和或不飽和、芳族或非芳族環;其條件是當連接至N時,R1a-i不為H。
於第十二方面,本發明係關於包含第十一方面之化合物之OLED裝
置。
於第十三方面,本發明係關於相應於第十一方面之配位體之化合物,其中金屬已被H取代。
於第十四方面,本發明係關於包含選自表1之金屬錯合物之化合物。
於第十五方面,本發明係關於包含第十四方面之化合物之OLED裝置。
下表1係提供使用G98/B31yp/cep-31g基礎組合之密度功能理論(DFT)計算,以獲得關於本發明各種化合物之HOMO、LUMO、間隙、偶極、S1及T1之估計。
其中n=1,2或3;R1a,R1b,R1c,R1d,R1e,R1f,R1g,R1h及R1i係各獨立
為H、烴基、雜原子取代之烴基、氰基、氟基、OR2a、SR2a、NR2aR2b、BR2aR2b或SiR2aR2bR2c,其中R2a-c係各獨立為烴基或雜原子取代之烴基,且其中R1a-i與R2a-c之任兩個可被連結以形成飽和或不飽和、芳族或非芳族環。X-Y為輔助配位體。式I錯合物係示於圖22中。
提供具有分枝狀烷基之化合物,譬如在R1e位置上提供新戊基或苄基。新戊基與苄基兩者具有苄基亞甲基,允許烷基或苯基相對於R1e取代基所連接環之自由旋轉。非將本發明之各方面限制於任何理論,咸信此種取代基會經過π-π堆疊之抑制,接著允許較乾淨之昇華作用與沉積,以及限制裝置中之激發子潛移,而造成具有顯著地較長壽命之裝置。於一項較佳具體實施例中,係提供具有式I之錯合物,其中R1a,R1b,R1c,R1d,R1e,R1f,R1g,R1h及R1i之至少一個係為含有至少4個碳原子之分枝狀烷基,且其中分枝係發生在比苄基性位置更遠之位置處。新戊基為較佳之分枝狀烷基。在一項特佳具體實施例中,分枝狀烷基係被提供於R1e位置上。較佳錯合物包括具有配位體gs1-32-gs1-62者。較佳錯合物亦包括具有配位體gs1-32-gs1-62者,其中在式gs1-32-gs1-62中尚未被指定之所有R基團R1a-R1i係為H。
提供在R1b位置上具有"扭轉芳基"之化合物。非將本發明之各方面限制於任何理論,咸信在R1b位置上之扭轉芳基會針對光氧化賦予較大安定性,而造成較長裝置壽命。於一項較佳具體實施例中,係提供具有式I之錯合物,其中R1b為具有以下結構之芳基:
其中Ra、Rb及Rc係獨立為H、烷基或芳基,其中Ra與Rb之至少一個
為烷基或芳基;且其中Ra、Rb及Rc可接合以形成稠合環。Ra與Rb之至少一個較佳為烷基。藉由Ra及/或Rb位置上之烷基或芳基所提供之立體整體性,會造成R1b位置上之芳基扭轉。此扭轉較佳係造成一種錯合物,其中R1b為芳基,具有距咪唑環之雙面夾角大於70度。Ra與Rb可均為烷基或芳基,其可造成更扭轉。由於製造之簡易性,故對於Ra及/或Rb位置,甲基為較佳烷基。由於外加之立體整體性組合,故對於Ra及/或Rb位置,相對於甲基,異丙基為較佳烷基。在R1b位置上具有"扭轉芳基"之較佳化合物包括es45與es46:
包含扭轉芳基之其他較佳化合物包括gs1-57與gs1-58。
提供在R1a位置上具有甲基或小烷基之化合物。非將本發明之各方面限制於任何理論,咸信在R1a位置上之甲基或小烷基會針對光氧化賦予較大安定性,而造成經顯著改良之外部量子效率(EQE)。
亦提供具有前述段落中所述取代基之任何組合之化合物,意即在R1b位置上之"扭轉芳基"、在R1e位置上之烷基譬如新戊基或苄基及/或在R1a位置上之甲基或小烷基之任何組合。在一種較佳組合中,R1b為芳基,具有距咪唑環之雙面夾角大於70度,且R1a為烷基。在另一種較佳組合中,錯合物為es38:
於一項具體實施例中,係提供具有新戊基取代之銥咪唑并[1,2-f]啡啶與二咪唑并[1,2-a:1',2'-c]喹唑啉錯合物作為發射體之長久留存磷光OLED。具有新戊基取代之咪唑并[1,2-f]啡啶與新戊基取代之二咪唑并[1,2-a:1',2'-c]喹唑啉錯合物作為發射材料之磷光有機發光裝置,在許多情況中顯示比具有缺乏新戊基之發射材料之裝置遠為較長之壽命。
本文中所提供之錯合物可有利地作為有機發光裝置中之發射材料使用。在許多狀況中,此種錯合物較佳為銥錯合物。此種裝置通常包含陽極、陰極及經配置於陽極與陰極間之有機發射層,其中有機層包含該發射錯合物。在一種較佳裝置型態中,有機發射層亦包含主體,且發射錯合物係以摻雜劑被提供於有機發射層中。此種裝置可包含其他層,如關於圖1與2所示及所述者。關於本文中所揭示發射材料之較佳主體包括含有咔唑基團之有機材料,此係由於此種材料之電子性質及以此種材料所發現之優越結果所致。較佳主體為mCBP,此係由於以mCBP所發現之優越結果所致。
裝置實例
裝置製造與度量
所有裝置均藉由高真空(<10-7托)熱蒸發製造。陽極電極為大約80-120毫微米氧化銦錫(ITO)。陰極包含大約0.5-1毫微米LiF,接著為100毫微米Al。於製造之後,立即將所有裝置以玻璃蓋包覆,以環氧樹脂密封在
氮手套箱(<1ppm H2O與O2)中,並將水份吸氣劑併入包裝內部。
所有裝置實例均具有有機堆疊,從ITO表面係順序地包含10毫微米銅苯二甲藍素(CuPc)、Ir(3-Meppy)3或es20作為空穴注入層(HIL),0或30毫微米4,4'-雙[N-(1-萘基)-N-苯基胺基]聯苯(α-NPD)作為空穴輸送層(HTL),以6-15重量%摻雜劑發射體(本發明化合物與比較化合物)摻雜之30、60或80毫微米3,3'-雙(N-咔唑基)聯苯(mCBP)或4,4'-雙(N-咔唑基)聯苯(CBP)作為發射層(EML)。當HPT或mCBP係作為ETL使用時,電子輸送層包含5毫微米HPT或mCBP或40毫微米BAlq作為ETL2,與20-45毫微米參(8-羥基喹啉基)鋁(Alq3)作為ETL1,或當BAlq係作為ETL2使用時,沒有ETL1。所有裝置實例之裝置結構均示於表1中。
電流-電壓-亮度(IVL)特徵、電致發光性質[發射最大值(Emmax)與
CIE座標]及操作壽命係經度量且摘述於表2中。裝置效率係在L=1000cd/平方米下比較。
與使用化合物A(一種常用藍色磷光摻雜劑)作為發射體之比較實例1之0.17、0.38比較,使用es1作為磷光發射體之裝置實例1係具有CIE為0.15、0.21。具有藍色達0.15、0.21之CIE之藍色磷光OLED,係比具有CIE為0.17、0.38者較令人期望。雖然與比較實例1之4.7%比較,裝置實例1之外部量子效率(EQE)為2.7%,但更重要的是,與比較實例1在L0=100cd/平方米下之170小時比較,裝置實例1之T1/2在L0=450cd/平方米下為270小時。這表示裝置實例1相較於比較實例1係至少7倍更安定。由於主要差異僅為磷光發射體,故此結果指出所提供之本發明化合物族群係極可使用於獲得相對較長久留存之深藍色磷光OLED。例如,裝置實例5在L0=680cd/平方米下係具有CIE為0.14、0.18,EQE為4.6%,及T1/2為310小時。裝置實例12在L0=500cd/平方米下係具有CIE為0.16、0.25,
EQE為7.1%,及T1/2為2,200小時。裝置實例14在L0=500cd/平方米下係具有CIE為0.15、0.26,EQE為4.5%,及T1/2>10,000小時。
在藍色磷光金屬錯合物中,由於3MLCT狀態之較高能階,故在3MLCT與3MC間之能隙變得較小,且低位MC狀態可以熱方式群集,使得其更易於降解,並導致量子產量上之損失。例如,具有Ir(咪唑并啡啶)為基料之藍色摻雜劑之裝置通常具有6-8% EQE(表2)。對於Ir(咪唑并啡啶)為基料之摻雜劑,增加3MLCT與3MC間之能隙可使裝置效率上升。金屬錯合物之MC狀態係關於配位體場強度。一般而言,較強供體會導致10Dq值之增加,與較高MC狀態。於此情況中,二甲基咪唑>甲基咪唑>咪唑之配位體場強度:
對於咪唑并啡啶族群,為增加咪唑環之供體能力,係考慮甲基之添加至R1a與R1b位置上。已發現在R1a位置上之甲基取代不會顯著地改變顏色,然而在R1a與R1b兩個位置上之甲基取代會實質上使顏色紅位移。因此,可使用任一種取代,但在R1a上之甲基取代係為較佳,其中係想要增加強供體,而無紅位移。
因此,es43係說明R1a位置上之甲基之較佳取代,相對於es1。顏色並未自未經取代之變型有極大轉移。但是,摻入es43作為磷光發射體之裝置,意即裝置實例19,係具有CIE為0.15、0.24,EQE為12.2%,自裝置實例1(EQE=2.7%)顯著地改良。此種EQE在迄今之藍色磷光OLED中係為極高。假定上,如在下文所提出之能量圖中所示,化合物es43之較高MC狀態在裝置操作期間可較不以熱方式群集,且會導致較高效率(圖3)。
所提出之es1與es43能量圖
更一般而言,在具有式I之錯合物之R1a位置上之供電子基團係因相同原因而為較佳,其係由於es43中之甲基取代而導致優越結果。以製造之簡易性為基礎,甲基為較佳取代基R1a位置。es43為較佳化合物。其他較佳化合物包括es47、es48、es49、es50、es51、es52、es53、es54及es55。
100:有機發光裝置
110:基板
115:陽極
120:空穴注入層
125:空穴輸送層
130:電子阻斷層
135:發射層
140:空穴阻斷層
145:電子輸送層
150:電子注入層
155:保護層
160:陰極
162:第一個導電層或薄金屬層
164:第二個導電層或較厚導電性金屬氧化物層
200:倒置之OLED或裝置
210:基板
215:陰極
220:發射層
225:空穴輸送層
230:陽極
圖1顯示具有個別電子輸送、空穴輸送及發射層以及其他層之有機發光裝置。
圖2顯示未具有個別電子輸送層之倒置有機發光裝置。
圖3顯示關於包含化合物es1之裝置之IVL、光譜及壽命數據。
圖4顯示關於包含化合物es6之裝置之IVL、光譜及壽命數據。
圖5顯示關於包含化合物es8之裝置之IVL、光譜及壽命數據。
圖6顯示關於包含化合物es9之裝置之IVL、光譜及壽命數據。
圖7顯示關於包含化合物es13之裝置之IVL、光譜及壽命數據。
圖8顯示關於包含化合物es14之裝置之IVL、光譜及壽命數據。
圖9顯示關於包含化合物es16之裝置之IVL、光譜及壽命數據。
圖10顯示關於包含化合物es17之裝置之IVL、光譜及壽命數據。
圖11顯示關於包含化合物es19之裝置之IVL與光譜數據。
圖12顯示關於包含化合物es20之裝置之IVL、光譜及壽命數據。
圖13顯示關於包含化合物es4之裝置之IVL、光譜及壽命數據。
圖14顯示es101在二氯甲烷溶液中之發射光譜。
圖15顯示關於包含化合物es20作為發射體與Ir(3-Meppy)3作為空穴注入層材料之裝置之IVL、光譜及壽命數據。
圖16顯示關於包含化合物es20作為發射體與空穴注入層材料兩者之
裝置之IVL、光譜及壽命數據。
圖17顯示關於包含化合物es38,具有發射層80毫微米厚之裝置之IV、量子效率、光譜及壽命數據。
圖18顯示關於包含化合物es38,具有發射層60毫微米厚之裝置之IV、量子效率、光譜及壽命數據。
圖19顯示關於包含化合物es38作為發射體與Ir(3-Meppy)3作為空穴注入層材料之裝置之IV、量子效率、光譜及壽命數據,該裝置具有發射層80毫微米厚。
圖20顯示關於包含化合物es38作為發射體與Ir(3-Meppy)3作為空穴注入層材料之裝置之IV、量子效率、光譜及壽命數據,該裝置具有發射層60毫微米厚。
圖21顯示關於包含化合物es38作為發射體與LG101作為空穴注入層材料之裝置之IV、量子效率、光譜及壽命數據,該裝置具有發射層20毫微米厚。LG101係得自LG Chem公司,Seoul,South Korea。
圖22顯示發射銥錯合物。
所請求之發明係代表及/或與一或多位下列當事人有關聯,關於聯合大學公司研究協定:Michigan大學、Princeton大學、Southern California大學之評議員與美商環球展覽(Universal Display)公司。該協定係在作成所請求發明之日期時及其之前即已生效,且所請求之發明係由於協定範圍內所進行活動之結果所造成。
除非另有指出,否則本文中所述磷光金屬錯合物之製備與純化係在
微弱室內光線下,或使用黃色濾光器於光線上,或使用經鋁箔包覆之玻璃器進行,以使金屬錯合物之光氧化降至最低。錯合物在其感光度上係相當地大改變。例如,一些錯合物譬如es20僅需要適度小心,而一些錯合物譬如es1在空氣中及在某些鹵化溶劑中係頗易於光引致之分解。除非另有指明,否則fac-異構物係被單離。
將啡啶酮(5.0克,0.027莫耳)添加至含有五氯化磷(6.1克,0.29莫耳)與50毫升氯化磷醯之反應燒瓶中。使反應混合物回流1小時,冷卻至室溫,並以甲苯稀釋。在迴轉式蒸發器上移除過量氯化磷醯與甲苯。使殘留物溶於醋酸乙酯中,且以蒸餾水,接著以鹽水洗滌。使溶劑層以硫酸鎂脫水乾燥,過濾,及濃縮,獲得pl2-i1(5.5克,96%),為灰白色固體。產物係藉質量光譜法與1H NMR確認,且直接使用於下一步驟中。
將得自步驟1之化合物pl2-i1(5.5克,0.026莫耳)添加至含有已溶於200毫升二乙二醇二甲酮中之胺基乙醛二甲基縮醛(6.8克,0.0646莫耳)之
反應燒瓶內,加熱至回流,及在氮大氣下攪拌。72小時後,當藉TLC測定時,反應已完成。使反應混合物冷卻至室溫,並藉蒸餾移除過量溶劑。使殘留物溶於二氯甲烷中,且藉由真空過濾移除不溶物。使溶劑以硫酸鎂脫水乾燥,過濾,及濃縮。將粗產物藉矽膠層析純化,使用80%醋酸乙酯與20%二氯甲烷作為溶離劑。收集經純化之產物,以己烷洗滌,及乾燥,獲得pl2-H(2.6克,46%產率),為灰白色固體。
將得自上述步驟2之化合物pl2-H(0.67克,3.1毫莫耳)與乙醯基丙酮酸銥(III)(0.38克,0.77毫莫耳)在氮大氣下加熱至250℃過夜。使反應物冷卻後,使殘留物溶於醋酸乙酯與二氯甲烷之1:1混合物中,過濾,並藉第一個矽膠層析,使用1:1醋酸乙酯:己烷,接著藉第二個矽膠管柱,使用1:1氯仿:己烷純化,獲得es1(0.15克,23%產率),為米黃色固體。關於磷光在二氯甲烷溶液中之高能量吸收峰係集中在458毫微米下,具有CIE座標0.18,0.27。
於1升圓形燒瓶中,添加2-碘基-4,5-二甲基丙胺酸(24.7克,100毫莫耳)、2-氰基苯基二羥基硼烷品吶可酯(27.5克,120毫莫耳)、二氯雙(三苯膦)鈀(II)(3.51克,5毫莫耳)、三鹽基性磷酸鉀單水合物(46.0克,200毫莫耳)及400毫升甲苯。將反應物加熱至回流,並在氮大氣下攪拌4小時。於冷卻後,過濾所形成之沉澱物,且以甲苯、己烷及水洗滌。產量為14克。
於1升圓形燒瓶中,添加上述中間物氯乙醛(50重量%,在水中,15.7克,100毫莫耳)、碳酸鈉(15.9克,150毫莫耳)及300毫升2-丙醇。將混合物加熱至回流,歷經2小時。移除溶劑,並將殘留物以CH2Cl2萃取,及進一步藉矽膠管柱純化。產量為13克。
下述程序係在微弱室內光線下,或使用黃色濾光器於光源上,或使用經鋁箔包覆之玻璃器具進行,以使金屬錯合物之光氧化降至最低。於50毫升Schlenk管狀燒瓶中,裝填6,7-二甲基咪唑并[1,2-f]啡啶(1.68克,6.8毫莫耳)與參(乙醯基丙酮酸)銥(III)(0.59克,1.4毫莫耳)。將反應混合物在氮大氣下攪拌,並於砂浴中,在240℃下加熱48小時。在冷卻後,使經固化之混合物溶於CH2Cl2中,及進一步藉矽膠管柱純化,獲得es12(0.30克)。結構與純度係藉1H NMR分析確認。λmax發射=456,486毫微米(在CH2Cl2溶液中,於室溫下);CIE=(0.18,0.23)。
於50毫升Schlenk管狀燒瓶中,裝填8b,13-二氮-茚并[1,2-f]菲(3.49克,13毫莫耳)與參(乙醯基丙酮酸)銥(III)(1.27克,2.6毫莫耳)。將反應
混合物在氮大氣下攪拌,並於砂浴中,在240℃下加熱48小時。在冷卻後,使經固化之混合物溶於CH2Cl2中,及進一步藉矽膠管柱純化,獲得es3(1.4克)。1H NMR結果係確認所要之化合物。λmax發射=492,524毫微米(CH2Cl2溶液,在室溫下),CIE=(0.23,0.51)。
於50毫升Schlenk管狀燒瓶中,裝填10-異丙基-8b,13-二氮-茚并[1,2-f]菲(6.07克,19.6毫莫耳)與參(乙醯基丙酮酸)銥(III)(1.91克,3.92毫莫耳)。將反應混合物在氮大氣下攪拌,並於砂浴中,在240℃下加熱48小時。在冷卻後,使經固化之混合物溶於CH2Cl2中,及進一步藉矽膠管柱純化,獲得es4(0.7克)。1H NMR結果係確認所要之化合物。λmax發射=496毫微米(CH2Cl2溶液,在室溫下),CIE=(0.26,0.57)。
於三頸1升圓底燒瓶中,裝填2,6-二溴基苯胺(143.51克,0.57莫耳)、2-氰基苯基二羥基硼烷三亞甲基酯(34.35克,0.19莫耳)、K3PO4.H2O(43.89克,0.1906莫耳)、PdCl2(PPh3)2(6.67克,9.5毫莫耳)及無水甲苯(700毫升)。將反應混合物於氮氣下加熱至100℃,歷經6小時。然後,使反應混合物濃縮至乾涸,並使其接受管柱層析,獲得標題化合物(19.11克,36.7%)。
於4-溴基-6-胺基啡啶(19.11克,69.91毫莫耳)、碳酸氫鈉(12.3克,146毫莫耳)在2-丙醇(200毫升)中之混合物內,添加氯乙醛(50%水溶液,17.35克)。將反應混合物於75℃下加熱5小時後,移除溶劑。使殘留物再溶於二氯甲烷中,且以水洗滌。合併有機離份,以硫酸鈉脫水乾燥,過濾,及在真空中濃縮。將粗製混合物於矽膠上,藉層析純化,使用己烷/醋酸乙酯(80/20),獲得標題化合物(13克,62%)。
於三頸1升圓底燒瓶中,裝填5-溴-咪唑并[1,2-f]啡啶(4.55克,15.31毫莫耳)、4-異丙基苯基二羥基硼烷(3.59克,21.89毫莫耳)、碳酸鉀(2N水溶液,27毫升)、Pd(OAc)2(223毫克,0.99毫莫耳)、三苯膦(1.044克,3.98毫莫耳)及100毫升1,2-二甲氧基乙烷。將反應混合物於氮氣下加熱至80℃,歷經17小時。以二氯甲烷稀釋反應混合物,且經由鹽水洗滌。合併有機離份,以硫酸鈉脫水乾燥,過濾,及在真空中濃縮。將粗製混合物於矽膠上,藉層析純化,使用己烷/醋酸乙酯(80/20),獲得純5-(4-異丙基苯基)-咪唑并[1,2-f]啡啶(4克,77%)。
於50毫升Schlenk管狀燒瓶中,裝填5-(4-異丙基苯基)咪唑并[1,2-f]啡啶(2.94克,8.74毫莫耳)與參(乙醯基丙酮酸)銥(III)(0.86克,1.75毫莫耳)。將反應混合物在氮大氣下攪拌,並於砂浴中,在240℃下加熱48小時。在冷卻後,使經固化之混合物溶於CH2Cl2中,及進一步藉矽膠管柱純化,獲得es7(0.7克)。1H NMR結果係確認所要之化合物。λmax發射=496毫微米(CH2Cl2溶液,在室溫下),CIE=(0.26,0.57)。
於500毫升圓形燒瓶中,添加7-氯基咪唑并[1,2-f]啡啶(3.8克,15毫莫耳,製自一般程序A)、4-異丙基苯基二羥基硼烷(3.7克,23毫莫耳)、醋酸鈀(II)(0.084克,0.38毫莫耳)、2-二環己基膦基-2',6'-二甲氧基聯苯(S-Phos,0.31克,0.75毫莫耳)、三鹽基性磷酸鉀單水合物(6.9克,30毫莫耳)及200毫升甲苯。將反應物加熱至回流,並在氮大氣下攪拌12小時。於冷卻後,使混合物藉矽膠管柱純化。產量為3.8克。
於50毫升Schlenk管狀燒瓶中,裝填7-(4-異丙基苯基)咪唑并[1,2-f]啡啶(3.8克,11.3毫莫耳)與參(乙醯基丙酮酸)銥(III)(1.11克,2.26毫莫耳)。將反應混合物在氮大氣下攪拌,並於砂浴中,在240℃下加熱48小
時。在冷卻後,使經固化之混合物溶於CH2Cl2中,及進一步藉矽膠管柱純化,獲得es10(1.2克)。1H NMR結果係確認所要之化合物。λmax發射=464,492毫微米(CH2Cl2溶液,在室溫下),CIE=(0.20,0.32)。
於500毫升圓形燒瓶中,添加7-氯基咪唑并[1,2-f]啡啶(5.2克,20.6毫莫耳,製自一般程序A)、參(乙醯基丙酮酸)鐵(III)(0.35克,1.0毫莫耳)、30毫升NMP及300毫升無水THF。在室溫下,於此混合物中,逐滴添加15毫升環己基氯化鎂溶液(2M,在醚中),並攪拌。於添加後,反應已完成。藉由1N HCl溶液使混合物淬滅。於一般處理及藉矽膠管柱純化後,產量為3.4克。
於50毫升Schlenk管狀燒瓶中,裝填7-環己基咪唑并[1,2-f]啡啶(3.4克,11.2毫莫耳)與參(乙醯基丙酮酸)銥(III)(1.1克,2.25毫莫耳)。將反應混合物在氮大氣下攪拌,並於砂浴中,在240℃下加熱48小時。在冷卻後,使經固化之混合物溶於CH2Cl2中,及進一步藉矽膠管柱純化,獲得es8(1.5克)。1H NMR結果係確認所要之化合物。λmax發射=462,486毫微米(CH2Cl2溶液,在室溫下),CIE=(0.17,0.27)。
於500毫升圓形燒瓶中,添加7-氯基咪唑并[1,2-f]啡啶(5.1克,20毫莫耳,製自一般程序A)、2,4,6-三異丙基苯基二羥基硼烷(9.9克,40毫莫耳)、Pd2(dba)3(0.92克,1.0毫莫耳)、2-二環己基膦基-2',6'-二甲氧基聯苯(S-Phos,1.64克,4.0毫莫耳)、三鹽基性磷酸鉀(12.7克,60毫莫耳)及200毫升甲苯。將反應物加熱至回流,並在氮大氣下攪拌72小時。於冷卻後,使混合物藉矽膠管柱純化。產量為2.6克。
於50毫升Schlenk管狀燒瓶中,裝填7-(2,4,6-三異丙基苯基)咪唑并[1,2-f]啡啶(2.6克,6.2毫莫耳)與參(乙醯基丙酮酸)銥(III)(0.61克,1.2毫莫耳)。將反應混合物在氮大氣下攪拌,並於砂浴中,在240℃下加熱48小時。在冷卻後,使經固化之混合物溶於CH2Cl2中,及進一步藉矽膠管柱純化,獲得es18(0.3克)。1H NMR結果係確認所要之化合物。λmax發射=464,488毫微米(CH2Cl2溶液,在室溫下),CIE=(0.17,0.29)。
於1升圓形燒瓶中,添加7-甲基咪唑并[1,2-f]啡啶(5.7克,24.5毫莫耳,製自一般程序A)與200毫升無水DMF。於室溫下,在黑暗中,於此混合物中,逐滴添加100毫升N-溴基琥珀醯亞胺DMF溶液(4.6克,25.7毫莫耳),並攪拌。將反應混合物持續攪拌過夜。接著,將混合物倒入1升水中,且攪拌。藉過濾收集沉澱物,及進一步以大量水,且最後以MeOH(50毫升x2)洗滌,然後乾燥。3-溴基-7-甲基咪唑并[1,2-f]啡啶之產量為6.5克。
於500毫升圓形燒瓶中,添加3-溴基-7-甲基咪唑并[1,2-f]啡啶(6.2克,20毫莫耳)、2,6-二甲基苯基二羥基硼烷(9.0克,60毫莫耳)、Pd2(dba)3(4.58克,5.0毫莫耳)、2-二環己基膦基-2',6'-二甲氧基聯苯(S-Phos,8.2克,20毫莫耳)、三鹽基性磷酸鉀(17.0克,80毫莫耳)及200毫升甲苯。將反應物加熱至回流,並在氮大氣下攪拌84小時。於冷卻後,使混合物藉矽膠管柱純化。產量為4.0克。
於50毫升Schlenk管狀燒瓶中,裝填3-(2,6-二甲基苯基)-7-甲基咪唑并[1,2-f]啡啶(3.3克,10毫莫耳)與參(乙醯基丙酮酸)銥(III)(0.98克,2.0
毫莫耳)。將反應混合物在氮大氣下攪拌,並於砂浴中,在240℃下加熱48小時。在冷卻後,使經固化之混合物溶於CH2Cl2中,及進一步藉矽膠管柱純化,獲得es20(0.8克)。1H NMR結果係確認所要之化合物。λmax發射=466,492毫微米(CH2Cl2溶液,在室溫下),CIE=(0.17,0.30)。
於1升圓形燒瓶中,添加6,7-二甲基咪唑并[1,2-f]啡啶(13.0克,52.8毫莫耳,製自一般程序A)與400毫升無水DMF。在室溫下,於黑暗中,於此混合物中,逐滴添加150毫升N-溴基琥珀醯亞胺DMF溶液(10.3克,58毫莫耳),並攪拌。將反應混合物持續攪拌過夜。接著,將混合物倒入1升水中,且攪拌。藉過濾收集沉澱物,及進一步以大量水,且最後以MeOH(50毫升x2)洗滌,並乾燥。3-溴基-6,7-二甲基咪唑并[1,2-f]啡啶之產量為14.7克。
於500毫升圓形燒瓶中,添加3-溴基-6,7-二甲基咪唑并[1,2-f]啡啶(6.5克,20毫莫耳)、2,6-二甲基苯基二羥基硼烷(9.0克,60毫莫耳)、Pd2(dba)3(4.58克,5.0毫莫耳)、2-二環己基膦基-2',6'-二甲氧基聯苯(S-Phos,8.2克,20毫莫耳)、三鹽基性磷酸鉀(17.0克,80毫莫耳)及200毫
升甲苯。將反應物加熱至回流,並在氮大氣下攪拌84小時。於冷卻後,使混合物藉矽膠管柱純化。產量為2.6克。
於50毫升Schlenk管狀燒瓶中,裝填3-(2,6-二甲基苯基)-6,7-二甲基咪唑并[1,2-f]啡啶(2.6克,7.4毫莫耳)與參(乙醯基丙酮酸)銥(III)(0.73克,1.5毫莫耳)。將反應混合物在氮大氣下攪拌,並於砂浴中,在240℃下加熱48小時。在冷卻後,使經固化之混合物溶於CH2Cl2中,及進一步藉矽膠管柱純化,獲得es21(0.35克)。1H NMR結果係確認所要之化合物。λmax發射=460,490毫微米(CH2Cl2溶液,在室溫下),CIE=(0.16,0.27)。
於500毫升圓形燒瓶中,添加5-溴基-7-第三-丁基咪唑并[1,2-f]啡啶(3.9克,11毫莫耳,製自一般程序A)、2,6-二甲基苯基二羥基硼烷(3.5克,23毫莫耳)、Pd2(dba)3(0.51克,0.56毫莫耳)、2-二環己基膦基-2',6'-二甲氧基聯苯(S-Phos,0.91克,2.2毫莫耳)、三鹽基性磷酸鉀(7.2克,34毫莫耳)及60毫升甲苯。將反應物加熱至回流,並在氮大氣下攪拌48小
時。於冷卻後,使混合物藉矽膠管柱純化。產量為1.2克。
於50毫升Schlenk管狀燒瓶中,裝填5-(2,6-二甲基苯基)-7-第三-丁基咪唑并[1,2-f]啡啶(0.40克,1.1毫莫耳)與參(乙醯基丙酮酸)銥(III)(0.10克,0.2毫莫耳)。將反應混合物在氮大氣下攪拌,並於砂浴中,在240℃下加熱24小時。在冷卻後,使經固化之混合物溶於CH2Cl2中,及進一步藉矽膠管柱純化,獲得fac-參銥(III)(0.01克)。1H NMR結果係確認所要之化合物。λmax發射=462,488毫微米(CH2Cl2溶液,在室溫下)。
於500毫升圓形燒瓶中,添加3-溴基-6,7-二甲基咪唑并[1,2-f]啡啶(8.2克,25.2毫莫耳)、2,6-二氯苯基二羥基硼烷(19.2克,100.9毫莫耳)、Pd2(dba)3(2.29克,2.5毫莫耳)、2-二環己基膦基-2',6'-二甲氧基聯苯(S-Phos,4.11克,10.0毫莫耳)、三鹽基性磷酸鉀(26.7克,126毫莫耳)及250毫升甲苯。將反應物加熱至回流,並在氮大氣下攪拌48小時。於冷卻後,使混合物藉矽膠管柱純化。3-(2,6-二氯苯基)-6,7-二甲基咪唑并[1,2-f]啡啶之產量為2.4克。
於500毫升圓形燒瓶中,添加3-(2,6-二氯苯基)-6,7-二甲基咪唑并[1,2-f]啡啶(2.4克,6.1毫莫耳)、苯基二羥基硼烷(3.74克,30毫莫耳)、Pd2(dba)3(1.1克,1.2毫莫耳)、2-二環己基膦基-2',6'-二甲氧基聯苯(S-Phos,1.97克,4.8毫莫耳)、三鹽基性磷酸鉀(7.64克,36毫莫耳)及100毫升甲苯。將反應物加熱至回流,並在氮大氣下攪拌12小時。於冷卻後,使混合物藉矽膠管柱純化。3-(2,6-二苯基苯基)-6,7-二甲基咪唑并[1,2-f]啡啶之產量為0.9克。
於25毫升Schlenk管狀燒瓶中,裝填3-(2,6-二苯基苯基)-6,7-二甲基咪唑并[1,2-f]啡啶(0.095克,0.2毫莫耳)與參(乙醯基丙酮酸)銥(III)(0.025克,0.05毫莫耳)。將反應混合物在氮大氣下攪拌,並於砂浴中,在240℃下加熱24小時。在冷卻後,使經固化之混合物溶於CH2Cl2中,及進一步藉矽膠管柱純化,獲得es22(0.01克)。1H NMR結果係確認所要之化合物。λmax發射=468,496毫微米(CH2CI2溶液,在室溫下),CIE=(0.19,0.35)。
於50毫升Schlenk管狀燒瓶中,裝填7-正-十二基咪唑并[1,2-f]啡啶(3.66克,9.34毫莫耳,經由一般程序A製成)與參(乙醯基丙酮酸)銥(III)(0.92克,1.87毫莫耳)。將反應混合物在氮大氣下攪拌,並於砂浴中,在
240℃下加熱48小時。在冷卻後,使經固化之混合物溶於CH2Cl2中,及進一步藉矽膠管柱純化,獲得es25(1.5克)。1H NMR結果係確認所要之化合物。
使49.0克(334毫莫耳)2-氰基苯二羥基硼烷與25.9克(340毫莫耳)1,3-丙二醇溶於1升CH2Cl2中,並在2升圓底燒瓶中攪拌20小時。然後,將溶液以抽氣傾倒在濾器上,以移除膠黏固體。接著,使濾液以無水MgSO4脫水乾燥,以移除殘留水,過濾,及蒸發溶劑,獲得淡色油。然後,使此油溶於CH2Cl2中,並在矽膠填充柱上純化,使用CH2Cl2作為溶離劑。使產物溶離份蒸乾,獲得產物,為透明油(35.7克,57.2%產率)。
將35.7克(190毫莫耳)2-(1,3,2-二氧硼陸圜-2-基)苯甲腈、31.9克(158毫莫耳)2-溴基-4-(第三丁基)苯胺、3.6克(3.16毫莫耳)肆(三苯膦)鈀(0)及59.0克(427毫莫耳)K2CO3,於含有400毫升甲苯與300毫升乙醇之2升燒瓶中加熱至回流。於恒定N2滌氣下,將反應混合物加熱19小時。反應混合物之HPLC顯示起始苯胺之消耗。使混合物冷卻,然後過濾,以移除鹼。以EtOAc洗滌鹼,以移除微量有機物質。使合併之濾液蒸乾,獲得不純油。將此油於矽膠管柱上純化,使用95/5/0.05
CH2Cl2/MeOH/NH4OH作為溶離劑,獲得分離。使產物溶離份蒸除溶劑,並使所形成之殘留物自CH2Cl2/己烷再結晶,產生14.0克標的化合物,為白色固體(35.5%產率,藉GC-MS確認)。
將13.0克(52毫莫耳)2-(第三-丁基)-6-胺基啡啶、12.3克(78毫莫耳,50% v/v,在H2O中)氯乙醛及8.74克(104毫莫耳)碳酸氫鈉添加至500毫升燒瓶中,並於N2大氣下,在200毫升2-丙醇中回流35小時。於完成時,使混合物冷卻,此時,TLC與HPLC顯示起始啡啶之完全消耗。使混合物溶於醋酸乙酯中,且過濾,以移除鹼。接著蒸發濾液,產生淡琥珀色油。將此油在矽膠管柱上純化,使用95/5/0.05 CH2Cl2/MeOH/NH4OH作為溶離劑。或者,配位體可使用自動化層析純化,以Al2O3管柱與2% EtOAc/己烷-20% EtOAc/己烷之梯度液作為溶離劑。使得自此等純化之產物溶離份蒸發溶劑,及自二氯甲烷/己烷再結晶,產生總計10.8克es9配位體,為白色固體(76.1%產率,NMR確認)。
將10.6克(38.7毫莫耳)es9配位體與4.76克(9.7毫莫耳)Ir(acac)3添加至裝有攪拌棒之50毫升Schlenk管件中。添加20滴十三烷,將管件以隔片密封,並充分以N2真空脫氣。將管件浸沒於砂浴中,且在245℃及N2大氣下加熱72小時。接著,使已冷卻之混合物溶於CH2Cl2中,伴隨著音振,
以溶解不純物。在真空中過濾混合物,並以CH2Cl2與己烷沖洗固體,獲得暗黃色固體,其量為8.5克。然後,使固體溶於1升煮沸之氯苯中,且傾倒在矽藻土墊(熱)上,以移除不純物。使所形成之濾液蒸發至500毫升,使摻雜劑再結晶成鮮明黃色固體(6.5克,66.4%產率,NMR確認,99.3%,HPLC檢測)。作為另一種純化方法,於三區帶昇華器中,在370℃及1.0 x 10-5托真空下,使3.5克摻雜劑昇華,獲得400毫克es9,為鮮明黃色固體(100%,HPLC檢測)。
使13.1克(69.8毫莫耳)2-(1,3,2-二氧硼陸圜-2-基)苯甲腈、16.3克(63.4毫莫耳)2-溴基-4-己基苯胺、1.62克(1.40毫莫耳)肆(三苯膦)鈀(0)及23.6克(171毫莫耳)碳酸鉀,在250毫升甲苯與100毫升EtOH中,於N2大氣下回流20小時。HPLC與TLC顯示苯胺幾乎完全消耗。使反應混合物冷卻,並通過濾器。以醋酸乙酯洗滌固體,以移除得自所收集鹼之有機物質。然後,使濾液蒸乾,並於矽膠上乾燥。將試樣使用矽膠層析純化,以100%醋酸乙酯作為溶離劑。接著,使產物溶離份蒸乾至最少量,並添加己烷,以使產物結晶成灰白色固體(7.05克,39.8%產率,GC-MS確認)。
將7.02克(25.2毫莫耳)2-(正-己基)-6-胺基啡啶、2.99克(37.8毫莫耳,50% v/v,在H2O中)氯乙醛及4.24克(50.4毫莫耳)碳酸氫鈉添加至500毫升燒瓶中,並於150毫升2-丙醇中,在N2大氣下回流20小時。於完成時,使混合物冷卻,此時,TLC與HPLC顯示起始啡啶之完全消耗。使混合物溶於EtOAc中,且過濾,以移除鹼。然後蒸發濾液,產生淡琥珀色油。接著,使此油在矽膠上乾燥,及在矽膠管柱上純化,使用70%醋酸乙酯/己烷→100%醋酸乙酯作為溶離劑。使得自此純化之產物溶離份蒸發溶劑,並自醋酸乙酯/己烷再結晶,產生總計4.9克es8配位體,為白色固體(55.1%產率,GC-MS確認)。
於50毫升schlenk管件中,裝填2.9克(9.6毫莫耳)es8配位體、0.94克(1.9毫莫耳)乙醯基丙酮酸銥及20滴十三烷。將反應器抽氣,並以氮氣回填三次。將反應物加熱至240℃,歷經70小時。使反應物冷卻,且添加二氯甲烷。將產物藉管柱層析純化,使用二氯甲烷作為溶離劑。合併含有所要產物之溶離份,及藉迴轉式蒸發移除溶劑。使產物自甲苯結晶,產生300毫克es8,使其藉由昇華作用進一步純化。
將99.8克(511毫莫耳)啡啶酮添加至裝有攪拌臂與冷凝器之3升多頸燒瓶中。添加1.2升冰醋酸,並將混合物在150rpm下攪拌,且加熱至回流。將已懸浮於100毫升醋酸中之90克(562毫莫耳)Br2逐滴添加至回流之溶液中,歷經3小時期間。於添加後,檢測混合物,且發現~80%完成。以此項檢測為基礎,在回流下,將另外20克Br2(在30毫升醋酸中)逐滴添加至混合物中。於添加後,檢測為>90%完成。逐滴添加最後20克Br2(在30毫升醋酸中),並在添加後,將混合物攪拌1小時。最後檢測為>97%。使混合物冷卻,且添加1升水,及過濾混合物。接著,將潮濕固體於硫代硫酸鈉水溶液中攪拌,以分解殘留溴,及再過濾。以H2O沖洗此等固體,並使其在真空中乾燥,以移除殘留水。然後,使固體自硝基苯(>2升)再結晶,並於漏斗中收集,獲得128克2-溴基啡啶酮(90.8%產率)。
將36.7克(139毫莫耳)2-溴基啡啶酮與30.7克(147毫莫耳)PCl5添加至1升多頸燒瓶(裝有攪拌臂、冷凝器及鹼集氣瓶)中,伴隨著350毫升POCl3,並在93℃下加熱16小時(註:HCl氣體之釋出係主要藉由鹼集氣瓶摧毀)。然後,檢測混合物,以測定2-溴基啡啶酮之完全消耗。將Dean Stark集氣瓶連接至燒瓶,以移除溶劑,達1/2體積。隨後,添加等體積之甲苯,並蒸餾出,以移除大部份POCl3。於第三次添加甲苯後,體積降至
300毫升,而經由迴轉式蒸發移除溶劑之其餘部份。接著,使固體自甲苯再結晶,及乾燥,獲得30.8克(78.6%產率,98%檢測)2-溴基-6-氯基啡啶,為灰白色固體(GC-MS確認)。
將20克4A經乾燥分子篩添加至裝有攪拌臂與冷凝器之2升多頸燒瓶中。將73.8克(252毫莫耳)2-溴基-6-氯基啡啶與79.4克(756毫莫耳)胺基乙醛二甲基縮醛添加至燒瓶中,伴隨著750毫升無水二乙二醇二甲醚。將混合物在135℃及N2大氣下,使用機械攪拌,加熱18小時。混合物之HPLC顯示起始物質完全消耗。接著,使反應物冷卻,且以醋酸乙酯濃化。以刮削自燒瓶側壁移除餅狀固體。然後在真空中過濾混合物,並將濾液放在一旁。接著,將得自漏斗之固體使用研缽與杵棒壓碎(當乾燥時),且添加至1升燒瓶中,及在600毫升氯苯中回流。過濾氯苯混合物,及合併濾液。然後經由迴轉式蒸發移除溶劑,獲得暗色固體。接著,將固體於大矽膠管柱上純化,使用CH2Cl2與CH2Cl2/MeOH作為溶離劑(註:當產物之CH2Cl2溶液放置在管柱上方時,並非所有固體均被溶解。經由添加額外溶離劑,固體最後確實溶解)。在漫長層析後,使產物溶離份蒸除溶劑,且以CH2Cl2/己烷清洗固體。過濾固體,當乾燥時,獲得62.0克標題化合物(83.1%產率,NMR確認)。
將3.12克(10.5毫莫耳)7-[溴基]-咪唑并[1,2-f]啡啶、3.93克(26.2毫莫耳)2,6-二甲基苯基二羥基硼烷、0.18克(0.53毫莫耳)2-(二環己基膦基)聯苯、0.13克(0.14毫莫耳)Pd2(dba)3及6.68克(31.5毫莫耳)磷酸鉀添加至裝有攪拌棒之50毫升不含空氣之燒瓶中,並以N2真空脫氣。添加20毫升無水間-二甲苯,且在N2大氣下,將混合物設定為130℃。16小時後,混合物之HPLC顯示起始啡啶之完全消耗。使混合物富含醋酸乙酯與二氯甲烷,及過濾,以移除鹼。然後以854-8741-076(1克規模反應)匯集濾液,且蒸乾,獲得暗色油。使此油於矽膠上乾燥(使用二氯甲烷),並將產物使用自動化層析,以5% EtOAc/己烷→50% EtOAc/己烷之梯度液層析,歷經1小時期間。蒸乾純溶離份,獲得3.40克卡其色固體(76.2%產率,98%,HPLC檢測,NMR確認)。
將3.40克(10.6毫莫耳)7-(2,6-二甲基苯基)-咪唑并[1,2-f]啡啶與1.30克(2.6毫莫耳)乙醯基丙酮酸銥(III)添加至裝有攪拌棒之25毫升Schlenk管件中,伴隨著12滴十三烷。將燒瓶密封,並以N2真空脫氣。接著,將混合物浸沒於砂浴中,且在250℃及N2大氣下加熱96小時。然後,使混合物溶於二氯甲烷中,及在矽膠管柱上純化,使用二氯甲烷作為溶離劑。使產物溶離份蒸除溶劑,獲得粗製摻雜劑。接著,使固體自二氯甲烷/甲醇再結晶,獲得2.1克es13,為黃色固體(68.9%產率,HPLC檢測,99.5%,
NMR確認)。
使20.0克(87.7毫莫耳)2-(1,3,2-二氧硼陸圜-2-基)苯甲腈、13.7克(73.1毫莫耳)2-溴基-4-丁基苯胺、1.70克(1.46毫莫耳)肆(三苯膦)鈀(0)及27.2克(198毫莫耳)碳酸鉀在400毫升甲苯與200毫升乙醇中,於N2大氣下回流20小時。HPLC與TLC顯示苯胺幾乎完全消耗。添加另外1.8克2-(1,3,2-二氧硼陸圜-2-基)苯甲腈,並再持續回流18小時。使反應混合物冷卻,且通過濾器。以醋酸乙酯洗滌固體,以移除得自所收集鹼之有機物質。接著,使濾液蒸乾,及在矽膠上乾燥。將試樣使用矽膠層析純化,以100%醋酸乙酯作為溶離劑。然後,使產物溶離份蒸乾至最少量,並使產物自EtOAc/己烷再結晶,獲得12.0克標題化合物,為淡黃色固體(65.9%產率,GC-MS確認)。
將12.0克(48.0毫莫耳)2-(正-丁基)-6-胺基啡啶、11.4克(72.0毫莫耳,50% v/v,在H2O中)氯乙醛及8.06克(96.0毫莫耳)碳酸氫鈉添加至500
毫升燒瓶中,並在200毫升2-丙醇中,於N2大氣下回流20小時。在完成時,使混合物冷卻,此時,TLC與HPLC顯示起始啡啶之完全消耗。使混合物溶於EtOAc中,且過濾,以移除鹼。然後蒸發濾液,產生褐色油。接著,使此油在矽膠上乾燥,並於矽膠管柱上純化,使用70%醋酸乙酯/己烷→100%醋酸乙酯作為溶離劑。使得自此純化之產物溶離份蒸發溶劑,且自醋酸乙酯/己烷再結晶,產生總計5.22克es15配位體,為灰白色固體(40.5%產率,NMR確認)。
將5.2克(21.0毫莫耳)es15配位體與2.58克(5.25毫莫耳)乙醯基丙酮酸銥(III)添加至裝有攪拌棒之25毫升Schlenk管件中。添加10滴十三烷,將管件以隔片密封,並充分以N2真空脫氣。將管件浸沒於砂浴中,且在250℃及N2大氣下加熱72小時。接著,使已冷卻之混合物溶於CH2Cl2中,伴隨著音振,以使不純物溶解。在真空中過濾混合物,並以CH2Cl2與己烷沖洗固體,獲得黃色固體,其量為2.74克。然後,使固體溶於130毫升煮沸之氯苯中,且傾倒在矽藻土墊(熱)上,以移除不純物。使所形成之濾液蒸發至乾涸。使殘留物溶於二氯甲烷中,且將內容物於矽膠管柱上,使用二氯甲烷及急驟式純化。使產物溶離份蒸除溶劑,並使固體自氯苯再結晶,產生1.52克es15,為黃色固體(29.6%產率,NMR確認,96.3%,HPLC檢測),將其中之1.5克在三區帶昇華器中,於360℃及1.0 x 10-5托真空下,藉由昇華作用進一步純化,獲得160毫克es15,為鮮明黃色固體。
於500毫升圓底燒瓶中,裝填12.2克(65.4毫莫耳)2-氰基苯基二羥基硼烷丙二醇酯、14.0克(65.4毫莫耳)2-溴基-4-異丙基苯胺、2.27(2毫莫耳)肆(三苯膦)鈀、18.0克(131毫莫耳)碳酸鉀、150毫升甲苯及50毫升乙醇。將反應物在N2下加熱至回流,歷經18小時。於冷卻至室溫後,以醋酸乙酯與水萃取反應物。以鹽水洗滌有機物質,接著以硫酸鎂脫水乾燥。藉過濾收集固體,並自濾液移除溶劑。將產物藉矽膠層析純化,使用94.5%二氯甲烷、5%甲醇、0.5%氫氧化銨作為溶離劑。合併含有所要產物之溶離份,且移除溶劑。產物係藉NMR與質譜確認。
於250毫升圓底燒瓶中,裝填5克(21.2毫莫耳)2-異丙基-啡啶-6-基胺、5克(31.8毫莫耳,在水中之50%溶液)氯乙醛、3.56克(42.4毫莫耳)碳酸氫鈉及150毫升異丙醇。將混合物加熱至回流,歷經18小時,然後冷卻至室溫。添加二氯甲烷,並過濾固體。藉迴轉式蒸發移除溶劑,且將產物藉管柱層析純化,以40%己烷/醋酸乙酯作為溶離劑。合併含有所要產物之溶離份,且移除溶劑。將產物藉矽藻土蒸餾進一步純化。收集5.8克es6
配位體。
於50毫升schlenk管件中,裝填2.8克(10.8毫莫耳)7-異丙基-咪唑并[1,2-f]啡啶與1.05克(2.2毫莫耳)乙醯基丙酮酸銥。將反應器抽氣,並以氮氣回填三次。將反應物加熱至250℃,歷經24小時。使反應物冷卻,且添加二氯甲烷,接著過濾固體,產生1.5克黃色固體。使固體溶於熱1,2-二氯苯中。使混合物冷卻,及過濾固體,產生0.4克es6,為黃色固體。將物質藉由昇華作用進一步純化。
於50毫升schlenk管件中,裝填2.9克(9.6毫莫耳)es8配位體、0.94克(1.9毫莫耳)乙醯基丙酮酸銥及20滴十三烷。將反應器抽氣,並以氮氣回填三次。將反應物加熱至240℃,歷經70小時。使反應物冷卻,且添加二氯甲烷。將產物藉管柱層析純化,以二氯甲烷作為溶離劑。合併含有所要產物之溶離份,且藉迴轉式蒸發移除溶劑。使產物自甲苯結晶,產生300毫克es8,將其藉由昇華作用進一步純化。
於2-氯基-4-氟基苯甲腈(1.0克,6.42毫莫耳)、2-胺基苯基二羥基硼烷品吶可酯(1.6克,7.1毫莫耳)、醋酸鈀(II)(0.07克,0.32毫莫耳)、金剛胺鹽酸鹽(0.24克,1.3毫莫耳)及碳酸銫(4.6克,14.1毫莫耳)之溶液中,添加先前以氮脫氣之二氧陸圜,並加熱至回流,歷經17小時。於冷卻後,將經蒸餾之水與二氯甲烷(50毫升)兩者添加至反應混合物中。分離溶劑層,及濃縮,獲得粗製油,將其藉管柱層析,經由首先使用1:1醋酸乙酯與己烷比例,接著為4:1醋酸乙酯/己烷作為溶離劑進行純化。收集純產物,獲得9-氟基-6-啡啶胺(42克,32%產率),其NMR光譜係與所提出之結構一致。
使9-氟基-6-啡啶胺(0.8克,3.7毫莫耳)與含有碳酸氫鈉(0.6克,7.54毫莫耳)之水中之氯化乙醯50%溶液(0.4克,5.66毫莫耳)溶於異丙醇(25毫升)中。使反應混合物在氮墊片下回流17小時。使反應混合物冷卻至室溫,並將沉澱物真空過濾,且以二氯甲烷洗滌。將粗產物藉管柱層析純化,使用醋酸乙酯與己烷之1:1比例作為溶離劑,接著為蒸餾,獲得10-氟-咪唑并[1,2-f]啡啶(0.46克,52%產率)。
於50毫升Schlenk管件中,裝填2.1克(9.6毫莫耳)10-氟-咪唑并[1,2-f]啡啶、0.87克(1.9毫莫耳)乙醯基丙酮酸銥及15滴十三烷。將反應器抽氣,並以氮氣回填三次。將反應物加熱至230℃,歷經40小時。使反應物冷卻,且添加二氯甲烷。將產物藉管柱層析純化,以二氯甲烷作為溶離劑。合併含有所要產物之溶離份,且藉迴轉式蒸發移除溶劑。使產物自二
氯甲烷/己烷混合物結晶,產生500毫克es5,將其藉由昇華作用進一步純化。
於無水THF(10毫升)之溶液中,添加鎂(1.25克,52毫莫耳)、3-第三-丁基溴苯(2.0克,9.4毫莫耳)及碘晶體。首先,將反應物稍微加熱,直到開始反應為止,接著移除。經由添液漏斗添加其餘之3-第三-丁基溴苯(8.0克,37.7毫莫耳),直到自發性回流停止。將反應混合物加熱至回流,歷經2小時。將Grignard經由注射器轉移至已溶於THF中之硼酸三甲酯之經冷卻溶液(-40℃)內,並添加,歷經10分鐘期間。使反應混合物溫熱至室溫過夜。將醋酸乙酯與經蒸餾之水添加至反應混合物中,且分離液層。以鹽水洗滌有機物質,及以硫酸鎂脫水乾燥。濃縮溶劑,並將產物藉矽膠管柱純化,使用10%醋酸乙酯與己烷作為溶離劑,獲得3-第三-丁基苯基二羥基硼烷(4.0克,46%產率),為白色固體。產物係藉GCMS確認,且直接使用於下一步驟中。
一起添加3-第三-丁基苯基二羥基硼烷(4.0克,22.4毫莫耳)、2-溴基-4-第三-丁基苯胺(4.3克,18.7毫莫耳)、醋酸鈀(II)(0.11克,0.468毫莫耳)、三苯膦(0.5克,1.8毫莫耳)及碳酸鉀在36毫升乙二醇二甲基醚中之25
毫升2M溶液。將反應混合物於回流下加熱18小時。使反應物冷卻至室溫,並自有機相分離水相,以醋酸乙酯萃取水相。合併有機萃液,以硫酸鎂脫水乾燥,過濾,及濃縮。將粗產物藉管柱層析純化,使用20%醋酸乙酯與己烷作為溶離劑。收集純產物2-胺基-3',5-二-第三-丁基聯苯(3.0克,57%產率),為白色固體,其NMR係與所提出之結構一致。
將2-胺基-3',5-二-第三-丁基聯苯(2.0克,7.11毫莫耳)添加至甲酸溶液中,並加熱至回流,歷經16小時。於冷卻後,添加水(25毫升),藉真空過濾收集產物與沉澱物。使粗產物溶於醋酸乙酯中,以水洗滌。使有機物質以硫酸鎂脫水乾燥,及濃縮,且藉管柱層析純化,使用10%醋酸乙酯與己烷作為溶離劑,當藉GCMS測定時,獲得純N-甲醯基-2-胺基-3',5-二-第三-丁基聯苯(1.8克,82%產率)。
使上述化合物N-甲醯基-2-胺基-3',5-二-第三-丁基聯苯(6.5克,21毫莫耳)溶於50毫升氯苯中,於其中添加5當量之過氧化二-第三-丁烷。將反應混合物加熱至110℃,歷經72小時。使反應混合物濃縮至一半,並冷卻至0℃。藉真空過濾收集所形成之沉澱物。以己烷洗滌灰白色固體,當藉GCMS測定時,獲得2,9-二-第三-丁基啡啶酮,且無任何進一步純化。
將上述2,9-二-第三-丁基啡啶酮(3.0克,9.7毫莫耳)添加至含有五氯化磷(3.0克,14.6毫莫耳)與50毫升氯化磷醯之反應燒瓶中。使反應混合物回流過夜,冷卻至室溫,並以甲苯稀釋。藉由迴轉式蒸發器移除過量氯化磷醯與甲苯。使殘留物溶於醋酸乙酯中,且以蒸餾水,接著以鹽水洗滌。
使溶劑層以硫酸鎂脫水乾燥,過濾,及濃縮,獲得所要之2,9-二-第三-丁基-6-氯基啡啶(3.0克,98%),為灰白色固體。產物係藉GC質譜確認,並未進一步純化,但直接使用於下一步驟中。
將2,9-二-第三-丁基-6-氯基啡啶(3.7克,11.0毫莫耳)添加至含有已溶於200毫升二乙二醇二甲醚中之胺基乙醛二甲基縮醛(2.4克,23毫莫耳)之反應燒瓶內,加熱至回流,並在氮大氣下攪拌。96小時後,當藉TLC測定時,反應已完成。使反應混合物冷卻至室溫,且藉蒸餾移除過量溶劑。使殘留物溶於二氯甲烷中。使溶劑以硫酸鎂脫水乾燥,過濾,及濃縮。將粗產物藉矽膠層析純化,使用10%醋酸乙酯與90%二氯甲烷作為溶離劑。收集經純化之產物,以己烷洗滌,及乾燥,獲得7,10-二-第三-丁基-咪唑并[1,2-f]啡啶(2.0克,56%產率),為白色固體。
於50毫升schlenk管件中,裝填2.0克(6.1毫莫耳)10-氟-咪唑并[1,2-f]啡啶、0.84克(1.7毫莫耳)乙醯基丙酮酸銥及10滴十三烷。將反應器抽氣,並以氮氣回填三次。將反應物加熱至240℃,歷經18小時。使反應物冷卻,且添加二氯甲烷。將產物藉管柱層析純化,以二氯甲烷作為溶離劑。合併含有所要產物之溶離份,且藉迴轉式蒸發移除溶劑。使產物自二氯甲烷/己烷混合物結晶,產生0.6克es19,將其藉由昇華作用進一步純化。
將2-氰基苯基二羥基硼烷品吶可酯(13.7克,60毫莫耳)、2-溴基-4,6-二甲苯胺(10.0克,50毫莫耳)、肆(三苯膦)鈀(0)(2.3克,2.0毫莫耳)及碳酸鉀(18.6克,138.21莫耳)一起添加至125毫升甲苯/甲醇之95/5混合物中。使溶劑脫氣,並將反應混合物加熱至回流,歷經48小時。於冷卻後,將反應混合物真空過濾,及蒸發有機物質,並將粗產物使用以三乙胺處理之矽膠管柱層析,及1:9醋酸乙酯與二氯甲烷混合物作為溶離劑純化。收集純產物,及濃縮,獲得3,5-二甲基-6-啡啶胺(9.1克,82%產率)。
將3,5-二甲基-6-啡啶胺(8.6克,39毫莫耳)、氯化乙醯(4.6克,58毫莫耳)在水中之50%溶液、258毫升異丙醇中之碳酸氫鈉(6.5克,77.4毫莫耳)加熱至回流,歷經40小時。在冷卻後,使粗產物溶於二氯甲烷中,及真空過濾。濃縮濾液,並使粗產物在二氯甲烷與醋酸乙酯混合物中結晶。藉真空過濾收集純產物,當藉NMR測定時,獲得5,7-二甲基-咪唑并[1,2-f]啡啶)(3.8克,40%產率)。
將3.7克(15.0毫莫耳)5,7-二甲基(咪唑并[1,2-f]啡啶)與1.85克(3.76毫莫耳)Ir(acac)3添加至裝有攪拌棒之50毫升Schlenk管件中。添加12滴十三烷,並將管件密封,及以N2真空脫氣。接著,將管件浸沒於砂浴中,並加熱至250℃,歷經72小時。使反應混合物冷卻,且使內容物與CH2Cl2一起音振,以溶解。過濾黃色固體,並在氯苯中加熱。經過矽藻土過濾溶液,及濃縮,以引致結晶化作用。過濾固體,產生600毫克es14,為黃色固體,將其藉由昇華作用進一步純化。
一起添加2-甲基苯基二羥基硼烷(24.7克,181毫莫耳)、2-溴基苯胺(25.7克,151毫莫耳)、醋酸鈀(II)(0.85克,3.78毫莫耳)、三苯膦(4.0克,15.1毫莫耳)、碳酸鉀之2M溶液(204毫升)及乙二醇二甲基醚(223毫升),並將反應混合物於回流下加熱18小時。使反應物冷卻至室溫後,自有機相分離水相。以醋酸乙酯萃取水相,且合併有機萃液,以硫酸鎂脫水乾燥,及過濾。將粗產物藉矽膠管柱層析純化,使用己烷中之10%醋酸乙酯作為溶離劑。收集純溶離份,合併,及濃縮,獲得2-胺基-2'-甲基-聯苯(23.5克,84.8%產率),其結構係藉GCMS與NMR確認。
將上述化合物2-胺基-2'-甲基-聯苯(11.0克,60毫莫耳)添加至含有三乙胺(24克,24毫莫耳)之無水甲苯(250毫升)中,並於氮墊片下攪拌。將氯甲酸乙酯(26克,240毫莫耳)經由注射器慢慢添加至經攪拌溶液中。以鹽水洗滌反應混合物,且分離有機物質,以硫酸鎂脫水乾燥,及濃縮,獲得N-乙氧羰基-2-胺基-2'甲基聯苯,為無色油(7.0克,46%產率),其結構係藉GCMS與NMR確認。
將上述化合物N-乙氧羰基-2-胺基-2'-甲基聯苯(6.7克,26毫莫耳)添加至多磷酸(15克)中,並加熱至170℃過夜。於冷卻後,添加水,且藉真空過濾收集白色沉澱物,獲得10-甲基-啡啶酮(3.5克,65%產率),其結構係與CGMS與NMR一致。
將上述化合物10-甲基-啡啶酮(4.0克,19毫莫耳)添加至含有五氯化磷(6.0克,0.29莫耳)與氯化磷醯(50毫升)之反應燒瓶中。使反應混合物回流4小時,冷卻至室溫,並以甲苯稀釋。藉由迴轉式蒸發器移除過量氯化磷醯與甲苯。使殘留物溶於醋酸乙酯中,且以蒸餾水,接著以鹽水洗滌。使溶劑層以硫酸鎂脫水乾燥,過濾,及濃縮,獲得6-氯基-10-甲基啡啶(4.1克,95%),為灰白色固體。產物係藉質譜與NMR確認,並未進一步純化,但直接使用在下一步驟中。
於二乙二醇二甲醚之溶液(100毫升)中,添加上述6-氯基-10-甲基-啡啶(1.8克,7.9毫莫耳)與2-溴基-4-異丙基丙胺酸(3.4克,15.8毫莫耳)。將反應混合物於氮墊片下,在160℃下攪拌3小時。於冷卻後,將沉澱物真空過濾,以醋酸乙酯,接著以己烷洗滌,獲得es27i-1(2.5克,78%產率),為米黃色固體。
使上述化合物(3.5克,8.7毫莫耳)溶於含有三苯膦(0.45克,
1.7毫莫耳)、醋酸鈀(0.12克,0.5毫莫耳)、碳酸鉀(3.6克,26毫莫耳)之甲苯中。使反應混合物在氮墊片下回流過夜。使反應混合物冷卻至室溫,且以蒸餾水,接著以鹽水洗滌。於分離有機層後,使es27配位體產物在矽膠管柱上純化。
於50毫升圓底燒瓶中,裝填1.8克(5.5毫莫耳)10-異丙基-3-甲基-8b,13-二氮-茚并[1,2-f]菲、0.67克(1.4毫莫耳)乙醯基丙酮酸銥及20毫升乙二醇。將反應物於氮氣下加熱至回流,歷經24小時。使反應物冷卻,並添加甲醇,接著過濾黃色固體。使固體溶於二氯甲烷中,且藉管柱層析純化,使用二氯甲烷作為溶離劑。合併含有所要產物之溶離份,且藉迴轉式蒸發移除溶劑。使產物自氯苯結晶,產生0.3克es27。
於三頸1升圓底燒瓶中,裝填2,6-二溴基-4-第三-丁基苯胺(38克,0.124莫耳)、2-氰基苯基二羥基硼烷品吶可酯(10克,0.044莫耳)、K3PO4.H2O(35.4克,0.154莫耳)、PdCl2(PPh3)2(1.8克,2.6毫莫耳)及無水甲苯(500毫升)。將反應混合物於氮氣下加熱至100℃,歷經6小時。然後,使反應混合物濃縮至乾涸,並使其接受管柱層析,獲得es17i-1(5.65
克,39%)。
於es17i-1(2.75克,8.4毫莫耳)、碳酸氫鈉(1.4克,16.7毫莫耳)在2-丙醇(75毫升)中之混合物內,添加氯乙醛(50%水溶液,1.96克)。將反應混合物在75℃下加熱5小時後,移除溶劑。使殘留物再溶於二氯甲烷中,且以水洗滌。合併有機離份,以硫酸鈉脫水乾燥,過濾,及在真空中濃縮。將粗製混合物於矽膠上藉層析純化,使用己烷/醋酸乙酯(80/20),獲得純es17i-2(2.52克,85%)。
於三頸1升圓底燒瓶中,裝填es17i-2(4.5克,12.7毫莫耳)、4-第三-丁基苯基二羥基硼烷(5.09克,29毫莫耳)、碳酸鈉(9.22克,87毫莫耳)、Pd(PPh)4(0.99克,0.86毫莫耳)、50毫升水及400毫升甲苯。將反應混合物於氮氣下加熱至100℃,歷經17小時。以二氯甲烷稀釋反應混合物,並經由鹽水洗滌。合併有機離份,以硫酸鈉脫水乾燥,過濾,及在真空中濃縮。將粗製混合物於矽膠上,藉層析純化,使用己烷/醋酸乙酯(80/20),獲得純es17i-3(5.05克,97%)。
於25毫升2頸燒瓶中,裝填es17i-3(3.41克,8.38毫莫耳)、Ir(acac)3(821.24毫克,1.67毫莫耳)及30滴十三烷。使燒瓶真空,並以氮再回填三次,接著加熱至220℃,歷經65小時。使反應混合物溶於二氯甲烷中,且使其接受管柱層析,獲得es17(1克,42%產率)。
於三頸圓底燒瓶中,裝填咪唑并[1,2-f]啡啶(11.6克,53.21毫莫耳)與600毫升無水THF。在-78℃下,將正-丁基鋰溶液(在環己烷中之2M溶液,39.9毫升,79.8毫莫耳)添加至反應混合物中。於-78℃下攪拌2小時後;在-78℃下添加氯化三丁基錫(25.97克,79.8毫莫耳)。將反應混合物於-78℃下攪拌兩小時。使反應混合物在真空下濃縮至乾涸,並使其接受管柱層析(將矽膠以三乙胺預處理,在己烷中之50% EtOAc),獲得標題化合物(24.61克,91%產率)。
於250毫升圓底燒瓶中,裝填3-(三丁基錫)-咪唑并[1,2-f]啡啶(23.87克,47毫莫耳)、2,6-二氯碘苯(12.84克,47.08毫莫耳)、PdCl2(PPh3)2(1.97克,2.82毫莫耳)及170毫升無水對二甲苯。將反應混合物在氮氣下加熱至120℃,歷經17小時。以二氯甲烷稀釋反應混合物,並藉由飽和KF水溶液洗滌。濾出沉澱物,且使濾液接受管柱層析(矽膠,二氯甲烷),獲得標題化合物(10.35克,60.8%產率)。
於200毫升圓底燒瓶中,裝填3-(2,6-二氯苯基)-咪唑并[1,2-f]啡啶(2.1克,5.8毫莫耳)、苯基二羥基硼烷(2.828克,23.4毫莫耳)、Pd(OAc)2(1.127克,5.02毫莫耳)、2-二環己基膦基-2',6'-二甲氧基聯苯
(4.11克,10.03毫莫耳)、K3PO4及70毫升無水甲苯。將反應混合物在氮氣下加熱至100℃,歷經22小時。使反應混合物濃縮至乾涸,並使其接受管柱層析,獲得標題化合物(1.62克,62%產率)。
於25毫升2頸燒瓶中,裝填3-(2,6-二苯基苯基)-咪唑并[1,2-f]啡啶(2.93克,6.56毫莫耳)、Ir(ACAC)3(0.643克,1.31毫莫耳)及30滴十三烷。燒瓶為真空,並以氮再回填三次,接著加熱至220℃,歷經65小時。使反應混合物溶於二氯甲烷中,且使其接受管柱層析,獲得es23(560毫克,28%產率)。
使苯并咪唑(2.00克,16.9毫莫耳)溶於30毫升無水二甲基甲醯胺中。
於其中添加氫化鈉(0.68克,60%,16.9毫莫耳)。將其在環境溫度下攪拌30分鐘,然後添加1.80毫升(16.9毫莫耳)2-氟基苯甲腈。將反應物於50℃下攪拌18小時,在此段時間後,使混合物於冰水浴中冷卻,並以100毫升水稀釋。以醋酸乙酯萃取產物。以水洗滌有機層,以硫酸鈉脫水乾燥,及在真空中蒸發,獲得標題化合物。質譜與NMR數據係與結構一致。亦以類似方式合成者為5,6-二甲基苯并咪唑類似物。
使化合物1(25.75克,117.5毫莫耳)溶於二氧陸圜(400毫升)中。於其中添加N-溴基琥珀醯亞胺(20.91克,117.5毫莫耳)。將其在回流下攪拌3小時,於此段時間後,將混合物倒入水中,並以醋酸乙酯萃取產物。使有機層以硫酸鈉脫水乾燥,在真空中濃縮,及層析(矽膠),使用二氯甲烷-醋酸乙酯5:1(v/v)之流動相,提供標題化合物。質譜與NMR數據係確認結構。亦以類似方式合成者為5,6-二甲基苯并咪唑類似物。
將化合物2(4.86克,16.3毫莫耳)在20毫升無水四氫呋喃中攪拌。於其中添加鋰六甲基二矽氮烷在四氫呋喃中之25毫升1N溶液。將反應物於65℃下攪拌2.5小時。接著,使反應混合物冷卻至環境溫度,並以水使反應淬滅。添加鹽酸水溶液(25毫升,1N溶液),且將其攪拌10分鐘,然後以氫氧化銨水溶液中和。藉過濾收集所形成之褐色固體,及在真空下乾燥。結構係藉質譜與NMR數據確認。
將化合物3(2.15克,9.18毫莫耳)置於200毫升圓底燒瓶中。於其中添加1,2-二碘苯(1.20毫升,9.18毫莫耳)、碘化銅(0.52克,2.75毫莫耳)、
1,10-二氮菲(0.50克,2.75毫莫耳)及碳酸鉀(2.66克,19.28毫莫耳)。使燒瓶脫氣,並以氮回填,然後添加40毫升無水二甲基甲醯胺。將反應物於150℃下攪拌18小時,接著冷卻,且倒入水中。過濾粗製固體,及層析(矽膠),使用二氯甲烷-甲醇19:1之流動相,獲得產物4。LCMS 309.2(ES+),309.2(AP+);1H NMR(CDCl3)δ8.75(m,2H),8.36(d,1H),8.15(d,1H),7.95(m,2H),7.81(m,1H),7.56(m,3H),7.44(m,2H).
於25毫升2頸燒瓶中,裝填4(0.6克,1.945毫莫耳)、Ir(acac)3(0.19克,0.389毫莫耳)及30滴十三烷。將燒瓶抽氣,並以氮再充填三次,接著加熱至240℃,歷經26小時。使所形成之混合物溶於二氯甲烷中,且使其接受矽膠管柱層析,獲得es101,其中結構係藉質量光譜法確認。
將化合物3(0.59克,2.52毫莫耳)在15毫升異丙醇中攪拌。於其中添加碳酸氫鈉(0.42克,5.04毫莫耳)與氯乙醛(0.50毫升,50%溶液,3.78毫莫耳)。將其在回流下攪拌7小時,然後冷卻,以水稀釋,並以二氯甲烷萃取。將產物使用管柱層析(矽膠)純化,以二氯甲烷-甲醇19:1溶離。LCMS258.7(AP+),259.3(ES+);1H NMR(DMSO d6)δ8.66(d,1H),8.55(m,1H),8.46(dd,1H),8.28(d,1H),7.84(m,2H),7.62(m,2H),7.47(m,
2H).
將氫化鈉(8.65克,60%,0.216莫耳)在75毫升無水二甲基甲醯胺中攪拌。於其中逐滴添加2,4-二甲基咪唑(20.75克,0.216莫耳)在100毫升DMF中之溶液。於環境溫度下攪拌1小時後,逐滴添加2-氟基苯甲腈(23.0毫升,0.216毫莫耳)在75毫升DMF中之溶液。將其在50℃下攪拌2小時,接著於環境溫度下16小時。然後,將混合物倒入水中,並以醋酸乙酯萃取產物。以水洗滌有機層,及以硫酸鈉脫水乾燥。使粗產物層析(矽膠),且以19:1二氯甲烷-甲醇,接著以9:1二氯甲烷-甲醇溶離,獲得產物,為固體。LCMS數據係確認結構。
使化合物6(5.18克,26.0毫莫耳)溶於乙腈(150毫升)中。於其中添加N-溴基琥珀醯亞胺(4.67克,26.0毫莫耳)。將其在回流下攪拌1小時,然後於真空中蒸發。使殘留物溶於二氯甲烷中,並以水洗滌。在真空中蒸發有機層,獲得標題化合物,為黃色固體。NMR係確認結構。
將化合物6(6.82克,34.5毫莫耳)分次添加至已冷卻至0℃之三氟醋酸酐(50毫升)中。15分鐘後,以乾冰-丙酮浴置換氯化鈉冰水浴,並逐滴添加硝酸(6.0毫升,70%)。將其攪拌至環境溫度,歷經16小時,於此段時間後,將其倒入冰水中,且以固態碳酸氫鈉中和。以二氯甲烷萃取產物,並在矽膠急驟式管柱上純化,以49:1二氯甲烷-甲醇溶離,獲得所要之產物,為橘色糊劑。LCMS數據係支持此結構。
使胺基苯甲腈(10.0克,85.0毫莫耳)溶於350毫升醋酸中。於其中添加2,5-二甲氧基四氫呋喃(11.0毫升,85.0毫莫耳)。將其在回流下攪拌2小時,於此段時間後,將反應混合物倒入水中,並以二氯甲烷萃取產物。將有機層以水洗滌,以硫酸鈉脫水乾燥,及在矽膠管柱上層析,使用1:1二氯甲烷-己烷之流動相,獲得標題化合物,為白色固體。NMR係確認此結構。
使化合物9(12.07克,72.0毫莫耳)溶於250毫升無水二甲基甲醯胺中。使其在冰水浴中冷卻。於其中添加N-溴基琥珀醯亞胺(12.77克,72.0毫莫耳)。將反應混合物在0℃下攪拌3小時,然後倒入水中。以二氯甲烷萃取產物。以水洗滌有機層,以硫酸鈉脫水乾燥,及在真空中濃縮。使粗產物進行管柱層析(矽膠),使用1:1二氯甲烷-己烷之流動相,獲得化合物10,為無色油。NMR與LCMS數據係確認此結構。
於1升圓底燒瓶中,添加7-溴基咪唑并[1,2,-f]啡啶(10克,33.89毫莫耳,經由一般程序製成)、六氫吡啶(8.66克,101毫莫耳)、醋酸鈀(532毫克,2.37毫莫耳)、二-第三-丁基聯苯基膦(1.41克,4.74毫莫耳)、第三-丁醇鈉(4.56克,47.45毫莫耳)及200毫升無水甲苯。將反應混合物加熱至100℃,歷經14小時。於冷卻後,使反應混合物在氧化鋁管柱上,藉層析純化。產量:3.19克。
於1升圓底燒瓶中,添加7-六氫吡啶-咪唑并[1,2,-f]啡啶(2.9克,33.89毫莫耳,製自步驟1)與200毫升無水DMF。於室溫下,在黑暗中,於此混合物中,逐滴添加100毫升N-溴基琥珀醯亞胺DMF溶液(1.79克,10.08毫莫耳),並攪拌。將反應混合物持續攪拌過夜。接著,將混合物倒入1升水中,且攪拌。藉過濾收集沉澱物,及進一步以大量水,且最後以MeOH(50毫升x2)洗滌,然後乾燥。3-溴基-7-六氫吡啶基-咪唑并[1,2-f]啡啶之產量為3.5克。
於500毫升圓形燒瓶中,添加3-溴基-7-六氫吡啶基-咪唑并[1,2-f]啡啶(3.5克,9.2毫莫耳)、2,6-二甲基苯基二羥基硼烷(8.28克,55.2毫莫耳)、Pd2(dba)3(4.21克,4.6毫莫耳)、2-二環己基膦基-2',6'-二甲氧基聯苯(S-Phos,7.55克,18.40毫莫耳)、三鹽基性磷酸鉀(15.6克,73.6毫莫耳)及200毫升二甲苯。將反應物加熱至回流,並在氮大氣下攪拌84小時。於冷卻後,使混合物藉矽膠管柱純化。產量為2.25克。
於50毫升Schlenk管狀燒瓶中,裝填3-(2,6-二甲基苯基)-7-六氫吡啶基-咪唑并[1,2-f]啡啶(1.75克,4.32毫莫耳)與參(乙醯基丙酮酸)銥(III)(0.5克,1毫莫耳)。將反應混合物在氮大氣下攪拌,並於砂浴中,在240℃下加熱48小時。在冷卻後,使經固化之混合物溶於CH2Cl2中,及進一步藉矽膠管柱純化,獲得所要之化合物(0.38克)。
於300毫升圓底燒瓶中,經由注射器添加6-氯基咪唑并[1,2,-f]啡啶(5
克,19.78毫莫耳,製自一般程序)、Pd2(dba)3(1.08克,1.18毫莫耳)、2-(二-環己基)膦基聯苯(998毫克,2.84毫莫耳)、THF中之鋰雙(三甲基矽烷基)胺(23.75毫升,1M,23.74毫升)。將反應燒瓶抽氣,並以氮回填。將反應混合物加熱至65℃過夜。使反應物冷卻至室溫,添加1M HCl水溶液(100毫升),且將反應物在室溫下攪拌5分鐘。接著藉由添加NaOH水溶液使溶液中和。將水相以二氯甲烷萃取三次。合併有機層,於真空中濃縮。使殘留物藉急驟式層析純化。產量為1.56克。
於100毫升圓底燒瓶中,添加6-胺基-咪唑并[1,2,-f]啡啶(100毫克,0.42毫莫耳,製自步驟1)、丁醛(61.84毫克,0.85毫莫耳)、三乙醯氧基硼氫化鈉(272毫克,1.28毫莫耳)及50毫升二氯甲烷。將反應混合物在室溫下攪拌過夜。藉由添加飽和NaHCO3水溶液使反應混合物淬滅,並以EtOAc萃取產物。濃縮EtOAc層,且產生所要之產物(140毫克)。
於50毫升Schlenk管狀燒瓶中,裝填6-N,N-二異丙基-咪唑并[1,2-f]啡啶(0.45克,1.14毫莫耳)與參(乙醯基丙酮酸)銥(III)(0.138克,0.28毫莫耳)。將反應混合物在氮大氣下攪拌,並於砂浴中,在240℃下加熱48小時。在冷卻後,使經固化之混合物溶於CH2Cl2中,及進一步藉矽膠管柱純化,獲得所要之化合物(0.1克)。
於500毫升2頸圓底燒瓶中,放置2-溴基-4-正-己基苯胺(8.87克,0.035莫耳)、2-氰基苯基二羥基硼烷品吶可酯(8.82克,0.039莫耳)、二氯雙(三苯膦)鈀(II)(0.98克,4%)及三鹽基性磷酸鉀單水合物(12.1克,0.053莫耳)。使燒瓶脫氣,並以氮回填,然後經由注射器添加甲苯(120毫升)。將反應物在回流下攪拌三小時,於此段時間後,使混合物冷卻至環境溫度。添加二氯甲烷(200毫升),且以水洗滌混合物。使有機層以硫酸鈉脫水乾燥,在真空中濃縮,及層析(矽膠)。以二氯甲烷-甲醇9:1 v/v溶離,產生所要之產物,為黃褐色固體。NMR、MS係確認此結構。
於250毫升圓底燒瓶中,放置2-己基啡啶-6-胺(6.17克,0.022莫耳)、2,4,6-三異丙基苯基溴基乙醛(7.93克,0.024莫耳,經由一般程序B製成)及異丙醇(50毫升)。將其在回流下攪拌2小時,然後添加碳酸氫鈉(3.7克,0.044莫耳)。將其在回流下再攪拌18小時。添加水(100毫升)與二氯甲烷(100毫升)。分離液層。使有機層以硫酸鈉脫水乾燥,在真空中濃縮,及層析(矽膠)。以醋酸乙酯-二氯甲烷1:1 v/v溶離,獲得所要之產物,為橘色油,其係在靜置時固化。1H NMR(CDCl3)δ8.72(d,1H),8.37(d,1H),7.64(m,2H),7.36(s,1H),7.19(m,1H),7.14(s,2H),7.00(d,1H),3.00(p,1H),2.69(t,2H),2.59(p,2H),1.36(d,6H),1.09(d,6H),0.93(d,6H),0.83(t,3H);GC MS 504.
於50毫升Schlenk管狀燒瓶中,裝填7-己基-3-(2,4,6-三異丙基苯基)咪唑并[1,2-f]啡啶(3.9克,7.72毫莫耳)與參(乙醯基丙酮酸)銥(III)(0.757克,1.54毫莫耳)。將反應混合物在氮大氣下攪拌,並於砂浴中,在240℃下加熱48小時。在冷卻後,使經固化之混合物溶於CH2Cl2中,及進一步藉矽膠管柱純化,獲得所要之化合物(0.732克)。
於裝有機械攪拌器、溫度計及添液漏斗之2升3頸燒瓶中,添加300克冰與300毫升H2SO4。將200毫升CH3CN中之2,6-二異丙基-4-溴基苯胺(46.0克,0.18莫耳)逐滴添加至此混合物中,同時,使溫度保持在5℃下。接著逐滴添加180毫升冰冷水中之亞硝酸鈉(22.5克,0.32莫耳),同時,使溫度保持約0℃。於室溫下,將所形成之透明溶液慢慢倒入碘化鉀(105克,0.63莫耳)在300毫升水中之溶液內。將混合物攪拌1小時。在正規處理後,使粗產物於170℃及真空下蒸餾,獲得1-碘基-2,6-二異丙基-4-溴苯(60克),於冷卻時,為淡褐色軟性固體。在-78℃下,於30分鐘內,將1-碘基-2,6-二異丙基-4-溴苯(17.6克,0.048莫耳)之150毫升無水甲苯溶液以n-BuLi(1.6M,在己烷中,75毫升)處理。於攪拌15分鐘後,逐滴添加50
毫升甲苯中之無水DMF(20毫升)。使所形成之混合物慢慢溫熱至室溫。在正規處理後,使粗產物於140℃及真空下蒸餾,獲得2,6-二異丙基-4-溴基苯甲醛(11.5克)。
在-78℃下,使氯化甲氧基甲基三苯基鏻(18.68克,54.5毫莫耳)懸浮於200毫升THF中。逐滴添加六甲基二矽氮化鋰(1.0M,在THF中,50毫升)。使所形成之混合物溫熱至0℃,並攪拌。使溶液冷卻至-78℃後,逐滴添加20毫升THF中之2,6-二異丙基-4-溴基苯甲醛(11.5克,42.7毫莫耳)。使混合物慢慢溫熱至室溫,並連續攪拌過夜。在正規處理後,使粗產物於165℃及真空下蒸餾,獲得2,6-二異丙基-4-溴-β-甲氧基苯乙烯(10克)。使此產物溶於20毫升二氧陸圜與100毫升18% HCl溶液中,在100℃下回流6小時。在正規處理後,使粗產物於160℃及真空下蒸餾,獲得2,6-二異丙基-4-溴苯基乙醛(7.5克)。
在0℃下,於2,6-二異丙基-4-溴苯基乙醛(7.3克,25.8毫莫耳)之無水DMF溶液中,添加2,6-二-第三-丁基-4-甲基酚(0.056克,0.26毫莫耳),接著為NBS(4.59克,25.8毫莫耳)。在攪拌數分鐘後,添加苯磺酸(8.16克,51.6毫莫耳)。將所形成之混合物於35℃及氮氣下攪拌12小時。在正規處理後,使粗產物藉管柱層析純化,獲得2-(2,6-二異丙基-4-溴苯基)丙醛(5.4克)。
於500毫升圓形燒瓶中,添加上述中間物2,3-二甲基-6-胺基啡啶(6.6克,30毫莫耳)與100毫升NMP。將混合物於80℃下攪拌48小時。在正規處理後,使粗產物藉矽膠管柱純化。在不同操作中,產量為約1至2克。
下述程序之各步驟應被保護隔離光線。於50毫升Schlenk管狀燒瓶中,裝填3-(2,6-二甲基-4-苯基苯基)-6,7-二甲基咪唑并[1,2-f]啡啶(1.90克,4.46毫莫耳,經由一般方法B,接著為Suzuki偶合,得自3-(2,6-二甲基-4-溴苯基)-6,7-二甲基咪唑并[1,2-f]啡啶)與參(乙醯基丙酮酸)銥(III)(0.48克,0.99毫莫耳)。將反應混合物在氮大氣下攪拌,並於砂浴中,在240℃下加熱48小時。在冷卻後,使經固化之混合物溶於CH2Cl2中,及進一步藉矽膠管柱純化,獲得es32(0.60克)。1H NMR結果係確認所要之化合物。λmax發射=468,490毫微米(CH2Cl2溶液,在室溫下),CIE=(0.17,0.33)。
下述程序之各步驟應被保護隔離光線。於50毫升Schlenk管狀燒瓶
中,裝填3-(2,6-二異丙基苯基)-6,7-二甲基咪唑并[1,2-f]啡啶(2.10克,5.17毫莫耳,經由一般方法B,接著以n-BuLi處理此THF溶液,並在-78℃下,藉由水使反應淬滅,得自3-(2,6-二異丙基-4-溴苯基)-6,7-二甲基咪唑并[1,2-f]啡啶)與參(乙醯基丙酮酸)銥(III)(0.56克,1.15毫莫耳)。將反應混合物在氮大氣下攪拌,並於砂浴中,在240℃下加熱48小時。在冷卻後,使經固化之混合物溶於CH2Cl2中,及進一步藉矽膠管柱純化,獲得es24(0.54克)。1H NMR結果係確認所要之化合物。λmax發射=458,488毫微米(CH2Cl2溶液,在室溫下),CIE=(0.17,0.25)。
下述程序之各步驟應被保護隔離光線。於50毫升Schlenk管狀燒瓶中,裝填3-(2,6-二異丙基-4-苯基苯基)-6,7-二甲基咪唑并[1,2-f]啡啶(1.75克,3.60毫莫耳,經由一般方法B,接著為Suzuki偶合,得自3-(2,6-二異丙基-4-溴苯基)-6,7-二甲基咪唑并[1,2-f]啡啶)與參(乙醯基丙酮酸)銥(III)(0.40克,0.80毫莫耳)。將反應混合物在氮大氣下攪拌,並於砂浴中,在240℃下加熱48小時。在冷卻後,使經固化之混合物溶於CH2Cl2中,及進一步藉矽膠管柱純化,獲得es37(0.54克)。1H NMR結果係確認所要之化合物。λmax發射=456,488毫微米(CH2Cl2溶液,在室溫下),CIE=(0.17,
0.24)。
下述程序之各步驟應被保護隔離光線。於50毫升Schlenk管狀燒瓶中,裝填3-(2,4,6-三異丙基苯基)-6,7-二甲基咪唑并[1,2-f]啡啶(1.95克,4.35毫莫耳,得自一般方法B,利用2,4,6-三異丙基苯甲醛作為起始物質)與參(乙醯基丙酮酸)銥(III)(0.43克,0.96毫莫耳)。將反應混合物在氮大氣下攪拌,並於砂浴中,在240℃下加熱48小時。在冷卻後,使經固化之混合物溶於CH2Cl2中,及進一步藉矽膠管柱純化,獲得es31(0.52克)。1H NMR結果係確認所要之化合物。λmax發射=460,490毫微米(CH2Cl2溶液,在室溫下),CIE=(0.16,0.25)。
包含es101作為發射化合物之OLED裝置係根據由Lin等人在美國專利申請案號11/241,981中,及由Tung等人在美國專利申請案號11/242,025中所述之程序製造,且當使10mA/平方公分電流通過裝置時,發射藍綠色光。
包含本發明摻雜劑之OLED裝置係根據由Lin等人在美國專利申請案
號11/241,981中,及由Tung等人在美國專利申請案號11/242,025中所述之程序製造,並獲致圖3-13、15及16中所詳述之數據。
將新戊基苯(43.17克,0.29莫耳)加入1升圓底燒瓶中。於其中添加醋酸酐(400毫升)。然後,將燒瓶置於冰水浴中,並添加硝酸銅(II)水合物(54.4克,0.29莫耳)。將反應物在0-5℃下攪拌一小時。接著移除冰浴,並將反應物攪拌至環境溫度,再歷經一小時,於此段時間後,將混合物倒入冰水中。使用氫氧化銨水溶液將pH值調整至7。然後以醋酸乙酯萃取產物。將有機層相繼以碳酸鈉水溶液與鹽水洗滌,及以硫酸鈉脫水乾燥。在真空中蒸發溶劑,獲得油狀物(55.9克,>99%),使用之而無需進一步純化。
將得自上述反應之4-硝基新戊基苯(55.9克),一次大約10克,在醋酸乙酯(100毫升)中,使用Pd-C 10%(1克)與H2(40psi)氫化20分鐘。然後經過矽藻土床過濾粗產物,及在真空中濃縮。當完成所有氫化作用時,使產物於矽膠管柱上純化,首先以9:1己烷-醋酸乙酯,接著以4:1己烷-醋酸乙酯溶離。首先溶離出不期望之異構物。其次溶離出所要之異構物,並以白色固體獲得。1H NMR(CDCl3)δ6.91(d,2H),6.61(d,2H),2.38(s,2H),0.87(s,9H).
使4-新戊基苯胺(18.38克,0.112莫耳)溶於200毫升無水二甲基甲醯胺中。於其中添加(逐滴)已溶於80毫升二甲基甲醯胺中之N-溴基琥珀醯亞胺(20.0克,0.112莫耳)。將反應物在環境溫度下攪拌過夜。然後,將反應物倒入水中,並以碳酸氫鈉中和。以醋酸乙酯萃取產物。接著,以水洗滌有機層,以硫酸鈉脫水乾燥,及在真空中蒸發,獲得粗產物,將其使用矽膠層析純化。以19:1己烷-醋酸乙酯溶離,獲得所要之產物(22.18克,82%),為淡橘色固體。1H NMR(CD2Cl2)δ7.25(s,1H),6.86(d,1H),6.68(d,1H),2.33(s,2H),0.85(s,9H).
將2-溴基-4-新戊基苯胺(22.12克,0.091莫耳)置於500毫升圓底燒瓶中。於其中添加2-氰基苯基二羥基硼烷酯(20.93克,0.091莫耳)、二氯化雙(三苯膦)鈀(II)6.3克(10%)、磷酸鉀單水合物(31.4克,0.14莫耳)、水(1.8毫升,0.1莫耳)及甲苯(200毫升)。將反應物抽氣,並以氮回填兩次,然後在回流下攪拌5小時。使反應物冷卻至環境溫度,及過濾。以己烷洗滌粗製固體,且於水與二氯甲烷之間作分液處理。使有機層以硫酸鈉脫水乾燥,及蒸發,獲得10.56克產物。使濾液層析(矽膠),首先以1:1醋酸乙酯-二氯甲烷,接著以9:1二氯甲烷-甲醇溶離,獲得另外6.32克產物。總產量16.88克,70%。米黃色固體。1H NMR(DMSO d6)δ8.61(d,1H),8.30(d,1H),8.15(s,1H),7.78(t,1H),7.63(t,1H),7.43(d,1H),7.27(d,1H),2.61(s,2H),0.91(s,9H).LCMS(ES+)265.1
於500毫升圓底燒瓶中,放置脒(7.13克,0.027莫耳)與2,6-二甲基溴苯基乙醛(6.13克,0.027莫耳)及異丙醇(200毫升)。將其在回流下攪拌2小時,然後添加碳酸氫鈉(4.54克,0.054莫耳)。將其在回流下再攪拌8小時,接著於真空中蒸發。使粗製殘留物於水與二氯甲烷之間作分液處理。使有機層脫水乾燥(硫酸鈉),及層析(矽膠)。以49:1己烷-醋酸乙酯,然後以9:1己烷-醋酸乙酯溶離,獲得產物,為白色固體(6.58克,62%)。1H NMR(CD2Cl2)d 8.75(m,1H),8.38(d,1H),8.19(s,1H),7.66(m,2H),7.36(m,2H),2.60(s,2H),2.08(s,6H),0.93(s,9H).
下述程序之各步驟應被保護隔離光線。於50毫升Schlenk管狀燒瓶中,裝填3-(2,6-二甲基苯基)-7-新戊基咪唑并[1,2-f]啡啶(4.69克,11.96毫莫耳)與參(乙醯基丙酮酸)銥(III)(1.17克,2.39毫莫耳)。將反應混合物在氮大氣下攪拌,並於砂浴中,在240℃下加熱48小時。在冷卻後,使經固化之混合物溶於CH2Cl2中,及進一步藉矽膠管柱純化,獲得所要之化合物(2.3克)。1H NMR係確認此結構。發射最大值=464,490毫微米(CH2Cl2溶液,在室溫下),CIE=(0.17,0.30)。
實例45係提供一種相對於實例44經改良之製備es38之方法。
將一升3頸燒瓶裝上架空攪拌器與氮氣入口管。於其中添加新戊基苯(20.0克,0.13莫耳)與中性氧化鋁(50克)。將其攪拌,以確保完全吸附。於燒杯中,添加溴(22.5克,0.14莫耳)與中性氧化鋁(50克)。將其以刮勺攪拌,接著分次添加至新戊基苯中,並攪拌。在數分鐘內,混合物從暗橘色來到乳黃色。然後,將氧化鋁置於矽膠管柱中,且以二氯甲烷溶離,獲得28.6克產物,為油狀物,使用之而無需進一步純化。
將此油4-新戊基溴苯(28.6克)置於裝有熱電偶、添液漏斗及回流冷凝管之1升3頸燒瓶中。於其中添加參(二苯亞甲基丙酮)二鈀(0)(3.5克,3莫耳%)與(2-聯苯基)二環己基膦(2.2克,5莫耳%)。將燒瓶抽氣,並以氮回填兩次,接著添加200毫升鋰雙三甲基矽烷基胺在THF中之1N溶液。將反應物於65℃下攪拌24小時,然後移除熱,且以水小心使反應淬滅。接著添加150毫升1N HCl,且將其攪拌30分鐘,然後添加10% NaOH,以使pH來到7。以二氯甲烷(3 x 100毫升)萃取產物。以鹽水(100毫升)洗滌合併之有機層,以硫酸鈉脫水乾燥,在真空中濃縮,及層析(矽膠),首先以9:1己烷-醋酸乙酯,接著以4:1己烷-醋酸乙酯溶離,獲得13.4克產物,為白色固體。
使10.82克(0.041莫耳)新戊基脒中間物溶於200毫升異丙醇中。於此溶液中,全部立即添加13.27克(0.041莫耳)溴化三異丙基苯乙醯中間物。將此溶液在85℃下加熱三小時。此時,使反應混合物冷卻至正好在異丙醇之回流溫度下。將碳酸氫鈉6.89克(0.082莫耳)分次添加至反應混合物中,歷經5分鐘期間。接著,將反應混合物加熱回復至高達85℃,並在此溫度下保持18小時。以300毫升水稀釋反應混合物。過濾此混合物。以2 x 250毫升醋酸乙酯萃取濾液。合併此等醋酸乙酯萃液,且以100毫升10% LiCl水溶液洗滌1x。然後,使此等萃液以硫酸鎂脫水乾燥,過濾,及在真空下汽提。
使得自處理之粗產物通過矽膠管柱。使管柱以5-25%醋酸乙酯/二氯甲烷溶離。合併最乾淨之溶離份,並在真空下汽提,產生4.5克產物。1H NMR(CDCl3)δ3.05(m,1H),2.60(m,4H),1.37(d,6H),1.11(d,6H),0.92(m,15H).
於50毫升Schlenk管件中,添加配位體(3.77克,8.16毫莫耳)、參(乙
醯基丙酮酸)銥(III)(0.8克,1.63毫莫耳,使其藉由Al2O3管柱純化,使用CH2Cl2作為溶離劑)及十三烷(50滴)。使混合物脫氣,並以氮回填,然後在砂浴(外部砂浴溫度為240-250℃)中加熱,並於氮大氣下攪拌72小時。在冷卻後,使反應混合物與溶劑之混合物(CH2Cl2:己烷=10毫升:90毫升)一起音振。獲得暗黃色懸浮液。藉過濾收集黃色固體。使固體藉急驟式管柱層析純化(SiO2;CH2Cl2)。於管柱層析後,使固體自醋酸乙酯再結晶。在結晶後,產量為0.8克。結構係藉質子nmr確認。
O-二新戊基苯可使用Nakayama等人,J.Org.Chem.1998,63,4912-4924之操作法合成。O-二新戊基苯可使用溴與中性氧化鋁,按實例45中所述溴化。
3,4-二新戊基溴苯可使用鋰六甲基二矽氮烷與鈀(0)觸媒,按實例45中所述胺化。
3,4-二新戊基苯胺可使用二甲基甲醯胺中之N-溴基琥珀醯亞胺,按實例44中所展示溴化。
可使2-溴基-4,5-二新戊基苯胺與2-氰基苯基二羥基硼烷品吶可酯,使用實例44中所述之條件反應,獲得脒中間物。
可使脒中間物與2-溴基-2-(2,6-二甲基苯基)乙醛,按實例44中所述反應,獲得配位體。
可使配位體與參(乙醯基丙酮酸)銥(III),在250℃之溫度下,按實例44中所述反應,獲得發射體。
可使脒中間物與異丙醇中之2-溴基-2-(2,4,6-三異丙基)乙醛,按實例46中所述反應,獲得配位體。
可將配位體按實例46中所述,在250℃下,以參(乙醯基丙酮酸)銥(III)連接,獲得發射體。
可使實例44中所述之2-溴基-4-新戊基苯胺與經酯取代之苯基二羥基硼烷,在溶劑譬如甲苯中,及使用鈀觸媒譬如雙(三苯膦)二氯化鈀反應,獲得啡啶酮。
可將啡啶酮在具有五氯化磷之氯化磷醯中,於回流下攪拌,獲得氯基啡啶。
可使氯基啡啶與2-溴基-4-新戊基苯胺,於回流下,在溶劑譬如二乙二醇二甲醚(二-乙二醇二甲基醚)中反應,獲得所示之苯基胺基取代之啡啶。
可使苯基胺基取代之啡啶,與鈀觸媒,譬如醋酸鈀,在溶劑譬如甲苯中反應,獲得苯并環化配位體。
於250℃下,配位體以參(乙醯基丙酮酸)銥(III)之處理係獲得發射體。
經溴化之硝基咪唑可使用由Singh等人,J.Org.Chem.1992,57,第3240-3242頁所報告之合成程序製成。咪唑以鐵粉在醋酸中之處理,係產生胺基咪唑。
可使胺基咪唑與2-氰基苯基二羥基硼烷品吶可酯,在類似實例44中所述之Suzuki偶合反應中反應,獲得脒中間物。
可使脒中間物與2-溴基-2-(2,6-二甲基苯基)乙醛,按實例44中所述反應,獲得標的配位體。
可將配位體以參(乙醯基丙酮酸)銥(III),於250℃下處理,獲得所要之發射體。
起始咪唑可藉由如實例50中之相同參考資料製成。硝基使用鐵粉在醋酸中之還原作用,係提供胺基咪唑。
可使胺基咪唑與2-氰基苯基二羥基硼烷品吶可酯,在類似實例44中所述反應之Suzuki反應中反應,而得脒。
可使脒與2-溴基-2-(2,6-二甲基苯基)乙醛,在溶劑譬如異丙醇中,按實例44中所述反應,獲得配位體。
可將配位體以參(乙醯基丙酮酸)銥(III),於250℃下,按實例46中所述處理,獲得標的發射體。
可使新戊基噻吩在以正-丁基鋰,於溶劑譬如四氫呋喃中處理時鋰化。經鋰化物種以乾冰(CO2)之處理係獲得羧酸。
起始羧酸與正-丁基鋰之反應,接著添加溴,係獲得經溴化之中間
物。
可使起始噻吩甲酸與市購可得之疊氮化二苯氧基磷醯,在三級丁醇中,於回流溫度下反應大約15小時,獲得經保護之胺。其係按照Yang等人,Chemica Scripta 1988,28,第275-279頁之一般程序。
可使起始噻吩與2-甲醯基苯基二羥基硼烷,使用Gronowitz等人,J.Heterocyclic Chem.,26,第865-868頁(1989)之修改反應,獲得所形成之噻吩并異喹啉。
可使噻吩并異喹啉與作為溶劑之1,2-二溴乙烷反應,獲得鹽。
首先可使鹽與甲苯中之氨及二氧化錳,使用Cronin等人,Organic Letters第9卷(12)第2253-2256頁(2007)之一般程序反應。
可使咪唑環在所指示之位置上,使用二甲基甲醯胺中之N-溴基琥珀醯亞胺,於環境溫度下選擇性地溴化。
可使經溴化之中間物與市購可得之2,6-二甲基苯基二羥基硼烷,在甲苯中,使用鈀觸媒譬如參(二苯亞甲基)二鈀反應,提供配位體。
可將配位體以參(乙醯基丙酮酸)銥(III),於250℃下處理,獲得所要之發射體。
可使2-溴基-4-新戊基苯胺與市購可得之2-甲醯基苯基二羥基硼烷,在Suzuki反應中反應,採用鈀(0)觸媒譬如市購可得之肆(三苯膦)鈀(0),獲得新戊基取代之啡啶。
可使啡啶與溴丙酮,在回流溶劑譬如乙腈中,使用Cronin等人,Organic Letters第9卷(12)第2253-2256頁(2007)之修改反應,提供四級鹽。
可將四級鹽以醋酸銨與二氧化錳處理,獲得上文所示之配位體。
可將配位體以參(乙醯基丙酮酸)銥(III),於250℃下處理,獲得所要
之摻雜劑。
按照Grag等人,SYNLETT第310-312頁(1998)之修改,使市購可得之鄰苯二甲醛(8.85克,0.066莫耳)溶於100毫升無水四氫呋喃中。使此溶液在乾冰乙腈浴中冷卻至-40℃。經由添液漏斗添加異丙基氯化鎂(100毫升,在THF中之2N溶液)。在添加Grignard試劑之後,將混合物攪拌至環境溫度過夜。然後,以水,接著以氯化銨水溶液使反應淬滅。接著經過矽藻土過濾粗製物質,並以醋酸乙酯(100毫升)稀釋濾液,然後以1N HCl洗滌。分離液層,且以水洗滌有機層,以硫酸鈉脫水乾燥,及在真空中蒸發。藉矽膠管柱層析,使用己烷:醋酸乙酯3:2之流動相達成最後純化,獲得二醇,為黏稠黃色油。1H NMR(CDCl3)δ4.63(d,2H,CHOH),2.04(m,2H,異丙基CH),1.06(d,6H,CH3),0.76(d,6H,CH3).
可使二醇溶於溶劑中,譬如甲醇,具有催化量之對-甲苯磺酸與觸媒譬如鈀/碳,並氫化,獲得二-異丁基苯。
二-異丁基苯可使用硝酸或發煙硝酸硝化,提供上文所示之硝化中間物。
可使3,4-二-異丁基硝基苯在溶劑譬如醋酸乙酯中,使用鈀/碳氫化,獲得苯胺。
於環境溫度下,可使3,4-二-異丁基苯胺在二甲基甲醯胺中,使用N-溴基琥珀醯亞胺溴化,產生經溴化之產物。
2-溴基-4,5-二-異丁基苯胺可與市購可得之2-氰基苯基二羥基硼烷品吶可酯,在溶劑譬如甲苯或二氧陸圜中,並使用觸媒譬如二氯化雙(三苯膦)鈀(II)進行Suzuki反應,提供所要之胺基啡啶。
可使胺基啡啶與(2,6-二甲基)苯基溴基乙醛,在異丙醇中反應,獲得配位體。
可將配位體以參(乙醯基丙酮酸)銥(III)與十三烷,在250℃下處理48-72小時,獲得所要之發射體。
可使市購可得之4-苄胺基苯在鄰位上,使用N-溴基琥珀醯亞胺,在二甲基甲醯胺中選擇性地溴化,獲得所要之2-溴基-4-苄胺基苯。
可使2-溴基-4-苄胺基苯與2-氰基苯基二羥基硼烷品吶可酯,在Suzuki反應中,使用鈀(II)觸媒反應,獲得所要之胺基啡啶。
可使胺基啡啶與(2,6-二甲基)苯基溴基乙醛,在異丙醇中,使用碳酸鈉作為鹼進行反應,產生所要之配位體。
可將配位體以參(乙醯基丙酮酸)銥(III)與十三烷,於250℃下處理48-72小時,獲得所要之發射體。
使起始咪唑并啡啶(5.0克,0.013莫耳)溶於75毫升二甲基甲醯胺中。於其中逐滴添加N-溴基琥珀醯亞胺(3.07克,0.017莫耳)在二甲基甲醯胺(15毫升)中之溶液。將溶液於氮氣及環境溫度下攪拌48小時,然後以水(200毫升)稀釋。藉由添加碳酸氫鈉使混合物呈鹼性。以醋酸乙酯(2 x 150毫升)萃取產物。將合併之萃液以10%氯化鋰水溶液洗滌,以硫酸鎂脫水乾燥,及在真空中濃縮。使產物藉管柱層析純化(中性,去活化之氧化
鋁),使用40-60%二氯甲烷在己烷中之流動相,獲得所要之產物(4.6克,76%),為黃褐色固體。LCMS 472.8(ES+).
於100毫升圓底燒瓶中,放置溴-咪唑并啡啶(0.45克,0.96毫莫耳)、三甲基環硼氧烷(0.93克,7.4毫莫耳)、醋酸鈀(II)(0.018克,0.08毫莫耳)、2-二環己基膦基-2',6'-二甲氧基聯苯(S-Phos)(0.17克,0.42毫莫耳)、甲苯(20毫升)及三鹽基性磷酸鉀(0.88克,3.8毫莫耳,溶於5毫升水中)。將燒瓶抽氣,並以氮回填,接著在回流下攪拌16小時,於此段時間後,分離液層,且使有機層以MgSO4脫水乾燥,在真空中濃縮,及層析(矽膠),以二氯甲烷中之15%醋酸乙酯溶離,獲得所要之產物(0.32克,82%),為白色固體。LCMS(ES+)407.0
於50毫升Schlenk管件中,添加配位體(3.77克,9.27毫莫耳)、參(乙醯基丙酮酸)銥(III)(0.91克,1.85毫莫耳,使其藉由Al2O3管柱純化,使用CH2Cl2作為溶離劑)及十三烷(50滴)。使混合物脫氣,並以氮回填,然後在砂浴(外部砂浴溫度為235℃)中加熱,並於氮大氣下攪拌116小時。在
冷卻後,使反應混合物與溶劑之混合物(在己烷中之30%二氯甲烷)一起音振。獲得暗黃色懸浮液。藉過濾收集黃色固體。將固體以熱乙腈廣泛地洗滌,獲得所要之化合物(1.97克;75%)。
於500毫升圓底燒瓶中,裝填啡啶(15克,83.69毫莫耳)、氯丙酮(277克)。將反應混合物在50℃下加熱2天。使反應混合物冷卻至室溫,並以醚稀釋,以引致沉澱。濾出沉澱物,產生所要之產物(6.74克,30%)。
在室溫下,於得自步驟1之產物(6.74克,24.8毫莫耳)在二氧陸圜(240毫升)中之經攪拌懸浮液內,添加醋酸銨(7.64克,99.1毫莫耳),接著為MnO2(21.54克,248毫莫耳)。使反應混合物回流4小時,然後添加10當量之Na2CO3(26.27克,248毫莫耳)。接著,使此懸浮液冷卻至室溫,並在玻料上過濾,然後,以丙酮廣泛地沖洗殘留物。最後,使母液濃縮至乾涸,且使其接受管柱層析(SiO2,在CH2Cl2中之1%甲醇),產生所要之化合物(5克,87%)。
於50毫升Schlenk管件中,添加得自步驟2之配位體(2.3克,9.9毫莫耳)、參(乙醯基丙酮酸)銥(III)(0.97克,1.98毫莫耳,使其藉由Al2O3管柱純化,使用CH2Cl2作為溶離劑)及十三烷(50滴)。使混合物脫氣,並以氮回填,然後在砂浴(外部砂浴溫度為235℃)中加熱,且於氮大氣下攪拌67小時。在冷卻後,使反應混合物與CH2Cl2一起音振。獲得暗黃色懸浮液。藉過濾收集黃色固體。以熱醋酸乙酯廣泛地洗滌固體,獲得所要之化合物(919毫克;53%)。
於250毫升圓底燒瓶中,放置胺基啡啶(2.88克,14.0毫莫耳)與異丙醇(100毫升)。使溴苯基乙醛(5.0克,14.0毫莫耳)溶於50毫升異丙醇中,並逐滴添加至反應混合物中。接著,將其在回流下攪拌16小時,於此段時間後,使反應混合物冷卻至70℃,且添加碳酸氫鈉(2.35克,28.0毫莫耳)。將反應物加熱至回流,並再攪拌16小時。然後,使反應混合物冷卻至環境溫度,及過濾。於真空中濃縮濾液,並進行管柱層析(矽膠),以己
烷中之10-20%醋酸乙酯溶離,獲得產物,為固體。GC MS 472.
使咪唑并啡啶(4.0克,8.48毫莫耳)溶於四氫呋喃(100毫升)中,並冷卻至-78℃。逐滴添加正-丁基鋰(8.5毫升,1.6N溶液)。將反應物於-78℃下再繼續攪拌一小時,然後添加水(2毫升)。將反應物攪拌至環境溫度,然後以鹽水(100毫升)與醋酸乙酯(100毫升)稀釋。使有機層以MgSO4脫水乾燥,及在真空中濃縮。使產物於氧化鋁管柱上純化,以己烷中之10-50%二氯甲烷溶離,獲得產物,為固體。GC MS 392.
於50毫升Schlenk管狀燒瓶中,裝填3-(2,6-二異丙基苯基)-7-甲基咪唑并[1,2-f]啡啶(1.80克,4.58毫莫耳)與參(乙醯基丙酮酸)銥(III)(0.49克,1.00毫莫耳)。將反應混合物在氮大氣下攪拌,並於砂浴中,在240℃下加熱48小時。在冷卻後,使經固化之混合物溶於CH2Cl2中,及進一步藉矽膠管柱純化,以二氯甲烷溶離,獲得(0.70克)。1H NMR結果係確認所要之化合物。λmax發射=462,492毫微米(CH2Cl2溶液,在室溫下),CIE=(0.17,0.30)。
於500毫升圓底燒瓶中,裝填2-甲醯基二羥基硼烷(9.40克,0.063莫耳)、2-溴基-4-甲基苯胺(5.0毫升,0.040莫耳)、雙(三苯膦)二氯化鈀(2.81克,0.004莫耳)、磷酸三鉀(19.1克,0.090莫耳)、甲苯(200毫升)及水(2毫升)。使其回流18小時。經過矽藻土過濾混合物。在真空中濃縮濾液,並於矽膠管柱上純化,以4:1二氯甲烷-醋酸乙酯溶離,獲得產物,為紅色固體。1H NMR(CDCl3)δ9.23(s,1H),2.63(s,3H).
於4,4-二甲基-2-戊酮(10克,0.0867莫耳)在150毫升甲醇中之溶液內;在冰/鹽浴中冷卻至-5℃;經過另一個漏斗,於迅速流中添加溴(14.7克,0.092莫耳)。將反應物於冰浴中攪拌3小時,同時,使溫度保持低於5℃。移除冰浴,並使反應在室溫下進行2小時。以250毫升水稀釋反應混合物,且以3 x 75毫升醚萃取。以10% Na2CO3與水洗滌醚萃液;以Na2SO4脫水乾燥;蒸發,產生所要之產物(15.18克,90%)。
於500毫升圓底燒瓶中,裝填2-甲基啡啶(1克,5.2毫莫耳)、1-溴基-4,4-二甲基戊烷-2-酮(1.2克,6.2毫莫耳)及10毫升二氧陸圜。將
反應混合物加熱至回流過夜。使反應混合物冷卻至室溫,並以醚稀釋,以引致沉澱作用。濾出沉澱物,產生所要之產物(1.8克)。
在室溫下,於得自步驟3之產物(19.6克,50毫莫耳)在二氧陸圜(0.7升)中之經攪拌懸浮液內,添加醋酸銨(15.64克,200毫莫耳),接著為MnO2(43.4克,580毫莫耳)。使反應混合物回流4小時,然後添加10當量之Na2CO3(53克,500毫莫耳)。接著,使此懸浮液冷卻至室溫,並於玻料上過濾,然後以丙酮廣泛地沖洗殘留物,最後,使母液濃縮至乾涸,且使其接受管柱層析(SiO2,在CH2Cl2中之5%甲醇),產生所要之化合物(11.4克)。
於50毫升Schlenk管件中,添加得自步驟4之配位體(2.72克,8.99毫莫耳)、參(乙醯基丙酮酸)銥(III)(0.885克,1.79毫莫耳,使其藉由Al2O3管柱純化,使用CH2Cl2作為溶離劑)及十三烷(50滴)。使混合物脫氣,並以氮回填,然後在砂浴(外部砂浴溫度為235℃)中加熱,且在氮大氣下攪拌67小時。於冷卻後,使反應混合物以CH2Cl2與己烷(4:6)之混合物溶解,並使其接受管柱層析(S1O2,在己烷中之40% CH2Cl2),且產生所要
之化合物(0.58克;30%)。
於500毫升圓底燒瓶中,裝填啡啶(14.8克)、3-溴基-2-丁酮(15.16克)及50毫升二氧陸圜。將反應混合物加熱至回流過夜。使反應混合物冷卻至室溫,並以醚稀釋,以引致沉澱作用。濾出沉澱物,產生所要之產物(25.2克)。
在室溫下,於得自步驟1之產物(25.2克,88毫莫耳)在二氧陸圜(1升)中之經攪拌懸浮液內,添加醋酸銨(27.1克,350毫莫耳),接著為MnO2(76.5克,880毫莫耳)。使反應混合物回流4小時,然後添加10當量之Na2CO3(93.27克,880毫莫耳)。接著,使此懸浮液冷卻至室溫,並於玻料上過濾,然後以丙酮廣泛地沖洗殘留物。最後,使母液濃縮至乾涸,且使其接受管柱層析(SiO2,在CH2Cl2中之1%甲醇),產生所要之化合物(14.9克,69%)。
於50毫升Schlenk管件中,添加得自步驟2之配位體(4克,16.24毫莫耳)、參(乙醯基丙酮酸)銥(III)(1.6克,3.24毫莫耳,使其藉由Al2O3管柱純化,使用CH2Cl2作為溶離劑)及十三烷(50滴)。使混合物脫氣,並以氮回填,然後在砂浴(外部砂浴溫度為235℃)中加熱,且在氮大氣下攪拌67小時。於冷卻後,使反應混合物與CH2Cl2一起音振。獲得暗黃色懸浮液。藉過濾收集黃色固體。以熱醋酸乙酯廣泛地洗滌固體,獲得所要之化合物(2.17克;72%)。
使82克(0.041莫耳)新戊基脒中間物溶於200毫升異丙醇中。於此溶液中,全部立即添加13.27克(0.041莫耳)溴化三異丙基苯乙醯中間物。將此溶液在85℃下加熱三小時。此時,使反應混合物冷卻至正好在異丙醇之回流溫度下。將碳酸氫鈉6.89克(0.082莫耳)分次添加至反應混合物中,歷經5分鐘期間。接著,將反應混合物加熱回復至高達85℃,並在此溫度下保持18小時。以300毫升水稀釋反應混合物。過濾此混合物。以2 x 250毫升醋酸乙酯萃取濾液。合併此等醋酸乙酯萃液,且以100毫升10% LiCl水溶液洗滌1x。然後,使此等萃液以硫酸鎂脫水乾燥,過濾,及在真空下汽提。
使得自處理之粗產物通過矽膠管柱。使管柱以5-25%醋酸乙酯/二氯
甲烷溶離。合併最乾淨之溶離份,並在真空下汽提,產生4.5克產物。1H NMR(CDCl3)δ3.05(m,1H),2.60(m,4H),1.37(d,6H),1.11(d,6H),0.92(m,15H).
於50毫升Schlenk管件中,添加配位體(3.77克,8.16毫莫耳)、參(乙醯基丙酮酸)銥(III)(0.8克,1.63毫莫耳,使其藉由Al2O3管柱純化,使用CH2Cl2作為溶離劑)及十三烷(50滴)。使混合物脫氣,並以氮回填,然後在砂浴(外部砂浴溫度為240-250℃)中加熱,並於氮大氣下攪拌72小時。在冷卻後,使反應混合物與溶劑之混合物(CH2Cl2:己烷=10毫升:90毫升)一起音振。獲得暗黃色懸浮液。藉過濾收集黃色固體。使固體藉急驟式管柱層析純化(SiO2;CH2Cl2)。於管柱層析後,使固體自醋酸乙酯再結晶。在結晶後,產量為0.8克。結構係藉質子nmr確認。
雖然本發明係針對特定實例與較佳具體實施例加以描述,但應明瞭的是,本發明並不限於此等實例與具體實施例。因此,如所請求之本發明係包括得自本文中所述特定實例與較佳具體實施例之變型,如熟諳此藝者所明瞭。
Claims (20)
- 如請求項1之有機發射層,其中R1a,R1b,R1c,R1d,R1e,R1f,R1g,R1h及R1i之至少一個為分枝狀烷基,含有至少4個碳原子,且其中分枝係發生在比苄基位置更遠之位置處。
- 如請求項2之有機發射層,其中R1a,R1b,R1c,R1d,R1e,R1f,R1g,R1h及R1i之至少一個為新戊基。
- 如請求項2之有機發射層,其中R1e為分枝狀烷基,含有至少4個碳原 子,且其中分枝係發生在比苄基位置更遠之位置處。
- 如請求項1之有機發射層,其中R1a,R1b,R1c,R1d,R1e,R1f,R1g,R1h及R1i均為H。
- 如請求項6之有機發射層,其中Ra與Rb之至少一個為烷基。
- 如請求項6之有機發射層,其中R1b為芳基,具有距咪唑環大於70度之雙面夾角。
- 如請求項6之有機發射層,其中Ra與Rb均為烷基。
- 如請求項9之有機發射層,其中Ra與Rb均為甲基。
- 如請求項10之有機發射層,其中Ra與Rb均為異丙基。
- 如請求項6之有機發射層,其中R1b為芳基,具有距咪唑環大於70度之雙面夾角,且R1a為烷基。
- 如請求項1之有機發射層,其中R1a為供電子基團。
- 如請求項13之有機發射層,其中R1a為甲基。
- 如請求項15之裝置,其中R1a,R1b,R1c,R1d,R1e,R1f,R1g,R1h及R1i之至少一個為分枝狀烷基,含有至少4個碳原子,且其中分枝係發生在比苄基位置更遠之位置處。
- 如請求項15之裝置,其中R1a為供電子基團。
- 如請求項15至18中任一項之裝置,其中有機發射層係進一步包含主體,其中主體為含有咔唑基團之有機材料。
- 如請求項19之裝置,其中主體為mCBP。
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