JP2011515423A - 金属錯体 - Google Patents
金属錯体 Download PDFInfo
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- JP2011515423A JP2011515423A JP2011501118A JP2011501118A JP2011515423A JP 2011515423 A JP2011515423 A JP 2011515423A JP 2011501118 A JP2011501118 A JP 2011501118A JP 2011501118 A JP2011501118 A JP 2011501118A JP 2011515423 A JP2011515423 A JP 2011515423A
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- 150000004696 coordination complex Chemical class 0.000 title description 5
- 229910052751 metal Inorganic materials 0.000 claims abstract description 44
- 239000002184 metal Substances 0.000 claims abstract description 44
- 150000001875 compounds Chemical class 0.000 claims description 104
- 239000003446 ligand Substances 0.000 claims description 72
- 125000003118 aryl group Chemical group 0.000 claims description 42
- 125000004429 atom Chemical group 0.000 claims description 38
- 229910052757 nitrogen Inorganic materials 0.000 claims description 33
- -1 As (O) 3 Inorganic materials 0.000 claims description 31
- 229910052717 sulfur Inorganic materials 0.000 claims description 25
- 229910052760 oxygen Inorganic materials 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- 229910052698 phosphorus Inorganic materials 0.000 claims description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 19
- 239000011159 matrix material Substances 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 239000000463 material Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 229920000642 polymer Polymers 0.000 claims description 15
- 230000007935 neutral effect Effects 0.000 claims description 14
- 125000004122 cyclic group Chemical group 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 13
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical class [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 12
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 11
- 239000000412 dendrimer Substances 0.000 claims description 10
- 229920000736 dendritic polymer Polymers 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 229910052741 iridium Inorganic materials 0.000 claims description 8
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical group [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 8
- 125000002950 monocyclic group Chemical group 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 239000011574 phosphorus Chemical group 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 5
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 229910052782 aluminium Inorganic materials 0.000 claims description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 5
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 5
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 229910052733 gallium Inorganic materials 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 229910052738 indium Inorganic materials 0.000 claims description 5
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims description 5
- 229910052697 platinum Inorganic materials 0.000 claims description 5
- 239000002243 precursor Substances 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 230000000903 blocking effect Effects 0.000 claims description 4
- 238000004132 cross linking Methods 0.000 claims description 4
- 239000010931 gold Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 150000002466 imines Chemical class 0.000 claims description 4
- 238000010791 quenching Methods 0.000 claims description 4
- 239000010948 rhodium Chemical group 0.000 claims description 4
- 229910052711 selenium Inorganic materials 0.000 claims description 4
- 229910052714 tellurium Inorganic materials 0.000 claims description 4
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 4
- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 claims description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 3
- 150000004703 alkoxides Chemical class 0.000 claims description 3
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 3
- 125000004986 diarylamino group Chemical group 0.000 claims description 3
- 230000005669 field effect Effects 0.000 claims description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical group [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052737 gold Inorganic materials 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- 229910052762 osmium Inorganic materials 0.000 claims description 3
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical group [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 3
- 108091008695 photoreceptors Proteins 0.000 claims description 3
- 229910052702 rhenium Inorganic materials 0.000 claims description 3
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical group [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 3
- 229910052703 rhodium Inorganic materials 0.000 claims description 3
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical group [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 3
- 229910052707 ruthenium Inorganic materials 0.000 claims description 3
- 239000010409 thin film Substances 0.000 claims description 3
- 229910052723 transition metal Inorganic materials 0.000 claims description 3
- 150000003624 transition metals Chemical class 0.000 claims description 3
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical group [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 3
- 229910052721 tungsten Inorganic materials 0.000 claims description 3
- 239000010937 tungsten Substances 0.000 claims description 3
- 229910017253 AsO Inorganic materials 0.000 claims description 2
- 229910017255 AsSe Inorganic materials 0.000 claims description 2
- 229910017259 AsTe Inorganic materials 0.000 claims description 2
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims description 2
- 229910018321 SbTe Inorganic materials 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims description 2
- 125000003636 chemical group Chemical group 0.000 claims description 2
- 229910052805 deuterium Inorganic materials 0.000 claims description 2
- 150000004985 diamines Chemical class 0.000 claims description 2
- 125000005240 diheteroarylamino group Chemical group 0.000 claims description 2
- 150000004662 dithiols Chemical class 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
- 150000002430 hydrocarbons Chemical group 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims description 2
- 229910001507 metal halide Inorganic materials 0.000 claims description 2
- 150000005309 metal halides Chemical class 0.000 claims description 2
- ANIDRZQDJXBHHM-UHFFFAOYSA-N pyridin-2-ylphosphane Chemical compound PC1=CC=CC=N1 ANIDRZQDJXBHHM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052957 realgar Inorganic materials 0.000 claims description 2
- 229910052718 tin Inorganic materials 0.000 claims description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 1
- 229910052746 lanthanum Inorganic materials 0.000 claims 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical group [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims 1
- 229910052706 scandium Inorganic materials 0.000 claims 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical group [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 claims 1
- 229910052727 yttrium Inorganic materials 0.000 claims 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical group [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- 239000010410 layer Substances 0.000 description 41
- 239000000203 mixture Substances 0.000 description 38
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 238000003786 synthesis reaction Methods 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- 229910021645 metal ion Inorganic materials 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 235000019341 magnesium sulphate Nutrition 0.000 description 9
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000007983 Tris buffer Substances 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- 229930192474 thiophene Natural products 0.000 description 5
- ZMVVDBASCHDMMS-UHFFFAOYSA-N 2-[bis(6-bromopyridin-2-yl)-fluoromethyl]-6-bromopyridine Chemical compound C=1C=CC(Br)=NC=1C(C=1N=C(Br)C=CC=1)(F)C1=CC=CC(Br)=N1 ZMVVDBASCHDMMS-UHFFFAOYSA-N 0.000 description 4
- ZJFQAFXHGFICSZ-UHFFFAOYSA-N 2-benzyl-6-[bis(6-benzylpyridin-2-yl)-methoxymethyl]pyridine Chemical compound C=1C=CC(CC=2C=CC=CC=2)=NC=1C(C=1N=C(CC=2C=CC=CC=2)C=CC=1)(OC)C(N=1)=CC=CC=1CC1=CC=CC=C1 ZJFQAFXHGFICSZ-UHFFFAOYSA-N 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 239000002739 cryptand Substances 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 125000002524 organometallic group Chemical group 0.000 description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000010189 synthetic method Methods 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 3
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 230000004888 barrier function Effects 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 3
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical compound C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- UPLBJCZYRCSIRI-UHFFFAOYSA-N 2-[[6-[fluoro-bis[6-[(2-hydroxyphenyl)methyl]pyridin-2-yl]methyl]pyridin-2-yl]methyl]phenol Chemical compound OC1=CC=CC=C1CC1=CC=CC(C(F)(C=2N=C(CC=3C(=CC=CC=3)O)C=CC=2)C=2N=C(CC=3C(=CC=CC=3)O)C=CC=2)=N1 UPLBJCZYRCSIRI-UHFFFAOYSA-N 0.000 description 2
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- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- UNQNIRQQBJCMQR-UHFFFAOYSA-N phosphorine Chemical compound C1=CC=PC=C1 UNQNIRQQBJCMQR-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- GDISDVBCNPLSDU-UHFFFAOYSA-N pyrido[2,3-g]quinoline Chemical compound C1=CC=NC2=CC3=CC=CN=C3C=C21 GDISDVBCNPLSDU-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical class C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- QRUBYZBWAOOHSV-UHFFFAOYSA-M silver trifluoromethanesulfonate Chemical compound [Ag+].[O-]S(=O)(=O)C(F)(F)F QRUBYZBWAOOHSV-UHFFFAOYSA-M 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- WSANLGASBHUYGD-UHFFFAOYSA-N sulfidophosphanium Chemical class S=[PH3] WSANLGASBHUYGD-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000003375 sulfoxide group Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000005287 template synthesis 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
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 229910001428 transition metal ion Inorganic materials 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- HJQFXBWQITUNBI-UHFFFAOYSA-N tris(6-bromopyridin-2-yl)methanol Chemical compound C=1C=CC(Br)=NC=1C(C=1N=C(Br)C=CC=1)(O)C1=CC=CC(Br)=N1 HJQFXBWQITUNBI-UHFFFAOYSA-N 0.000 description 1
- ZKGSLMSVQUOOMU-UHFFFAOYSA-N tris(6-bromopyridin-2-yl)phosphane Chemical compound BrC1=CC=CC(P(C=2N=C(Br)C=CC=2)C=2N=C(Br)C=CC=2)=N1 ZKGSLMSVQUOOMU-UHFFFAOYSA-N 0.000 description 1
- RREURMKQENZDQR-UHFFFAOYSA-N trithiazole Chemical compound S1SC=NS1 RREURMKQENZDQR-UHFFFAOYSA-N 0.000 description 1
- YGPLLMPPZRUGTJ-UHFFFAOYSA-N truxene Chemical compound C1C2=CC=CC=C2C(C2=C3C4=CC=CC=C4C2)=C1C1=C3CC2=CC=CC=C21 YGPLLMPPZRUGTJ-UHFFFAOYSA-N 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000001947 vapour-phase growth Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
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Abstract
【選択図】 なし
Description
aは0または1であり、a=0である場合、前記架橋ユニットVは存在せず;
L1は式(3)の配位子部分であり、
Zは、出現する毎に同一であるかまたは異なり、第3、第4、第5または第6主族からの置換されたまたは未置換の原子であって、前記環Cy1とCy2とを架橋しており;
D1、D2は、出現する毎に同一であるかまたは異なり、少なくとも1個のドナー原子を含む化学基を表している。
Cy1、Cy2は、出現する毎に同一であるかまたは異なり、5個ないし30個の芳香族環原子を有し、1個以上の基Rで置換されていてもよいアリール基もしくはヘテロアリール基、または環式の飽和のもしくは好ましくは不飽和のカルベンであり;ここで2つの基の一方Cy1またはCy2は、形式的に負に荷電した炭素を介して、または形式的に負に荷電した環外ドナー原子を介して前記金属に結合しており、2つの基Cy1およびCy2の他方は、該基Cy1またはCy2の一部であって、窒素、リンおよびカルベンの形態にある炭素から選択される中性ドナー原子を介して結合しており;
Vは、出現する毎に同一であるかまたは異なり、B、BR-、B(CR2)3、RB(CR2)3 -、B(O)3、RB(O)3 -、B(CR2CR2)3、RB(CR2CR2)3 -、B(CR2O)3、RB(CR2O)3 -、B(OCR2)3、RB(OCR2)3 -、Al(O)3、RAl(O)3 -、Al(OCR2)3、RAl(OCR2)3 -、CR、CO-、CN(R1)2、RC(CR2)3、RC(O)3、RC(CR2CR2)3、RC(CR2O)3、RC(OCR2)3、RC(SiR2)3、RC(SiR2CR2)3、RC(CR2SiR2)3、RC(SiR2SiR2)3、SiR、RSi(CR2)3、RSi(O)3、RSi(CR2CR2)3、RSi(OCR2)3、RSi(CR2O)3、RSi(SiR2)3、RSi(SiR2CR2)3、RSi(CR2SiR2)3、RSi(SiR2SiR2)3、N、NO、NR+、N(CR2)3、RN(CR2)3 +、N(C=O)3、N(CR2CR2)3、RN(CR2CR2)+、P、RR+、PO、PS、PSe、PTe、P(O)3、PO(O)3、P(OCR2)3、PO(OCR2)3、P(CR2)3、PR(CR2)3 +、PO(CR2)3、P(CR2CR2)3、PR(CR2CR2)3 +、PO(CR2CR2)3、As、AsR+、AsO、AsS、AsSe、AsTe、As(O)3、AsO(O)3、As(OCR2)3、AsO(OCR2)3、As(CR2)3、AsR(CR2)3 +、AsO(CR2)3、As(CR2CR2)3、AsR(CR2CR2)3 +、AsO(CR2CR2)3、Sb、SbR+、SbO、SbS、SbSe、SbTe、Sb(O)3、SbO(O)3、Sb(OCR2)3、SbO(OCR2)3、Sb(CR2)3、SbR(CR2)3 +、SbO(CR2)3、Sb(CR2CR2)3、SbR(CR2CR2)3 +、SbO(CR2CR2)3、Bi、BiR+、BiO、BiS、BiSe、BiTe、Bi(O)3、BiO(O)3、Bi(OCR2)3、BiO(OCR2)3、Bi(CR2)3、BiR(CR2)3 +、BiO(CR2)3、Bi(CR2CR2)3、BiR(CR2CR2)3 +、BiO(CR2CR2)3、S+、S(CR2)3+、S(CR2CR2)3 +、Se+、Se(CR2)3 +、Se(CR2CR2)3 +、Te+、Te(CR2)3 +、Te(CR2CR2)3 +、1位、2位および3位を介してリンクしたシクロプロパン、1位、2位および3位を介してリンクしたアジリジン、もしくは対応する非対称の類似化合物;または、式(12)、(13)もしくは(14)のユニットであり、
Zは、出現する毎に同一であるかまたは異なり、O、S、S(=O)、S(=O)2、NR、PR、P(=O)R、P(=NR)、CR2、C(=O)、C(=NR)、C(=CR2)、SiR2またはBRであり;
Rは、出現する毎に同一であるかまたは異なり、H、D、F、Cl、Br、I、N(R1)2、CN、NO2、Si(R1)3、B(OR1)2、C(=O)R1、P(=O)(R1)2、S(=O)R1、S(=O)2R1、OSO2R1、1個ないし40個のC原子を有する直鎖のアルキル、アルケニル、アルキニル、アルコキシもしくはチオアルコキシ基、または3個ないし40個のC原子を有する分枝鎖もしくは環式のアルキル、アルケニル、アルキニル、アルコキシもしくはチオアルコキシ基(これらの各々は1個以上の基R1によって置換されていてもよく、ここで1個以上の非隣接のCH2基はR1C=CR1、C≡C、Si(R1)2、Ge(R1)2、Sn(R1)2、C=O、C=S、C=Se、C=NR1、P(=O)(R1)、SO、SO2、NR1、O、SまたはCONR1と置換されていてもよく、1個以上のH原子はF、Cl、Br、I、CNまたはNO2と置換されていてもよい)、または5個ないし60個の芳香族環原子を有する芳香族環構造もしくは芳香族複素環構造(これは各例において1個以上の基R1によって置換されていてもよい)、または5個ないし60個の芳香族環原子を有するアリールオキシもしくはヘテロアリールオキシ基(これは1個以上の基R1によって置換されていてもよい)、またはジアリールアミノ基、10個ないし40個の芳香族環原子を有するジヘテロアリールアミノ基もしくはアリールへテロアリールアミノ基(これは1個以上の基R1によって置換されていてもよい)、またはこれらの構造の組み合わせであり;2つ以上の置換基Rは互いに単環式または多環式の脂肪族環構造、芳香族環構造および/またはベンゾ縮合環構造を形成していてもよく;
R1は、出現する毎に同一であるかまたは異なり、H、F、または1個ないし20個のC原子を有する脂肪族、芳香族および/または複素芳香族炭化水素基(更に、1個以上のH原子がFによって置換されていてもよい)であり;2個以上の置換基R1は互いに単環式または多環式の脂肪族環構造または芳香族環構造を形成していてもよく;
aは上で定義した通りである。
Eは、出現する毎に同一であるかまたは異なり、C、NまたはPであり;
Qは、出現する毎に同一であるかまたは異なり、O、S、Se、TeまたはNであり;
Tは、出現する毎に同一であるかまたは異なり、N、PまたはCであり;
Aは、出現する毎に同一であるかまたは異なり、NR1、SまたはOであり;
Xは、出現する毎に同一であるかまたは異なり、CR、N若しくはPであり、この場合、式(27)、式(28)、式(29)および式(30)において、カルベン環中の2つの基Xの間に二重結合が存在するか;または式(27)、式(28)、式(29)および式(30)におけるカルベン環中のXは、出現する毎に同一であるかまたは異なり、CR2を表しており;
Yは、出現する毎に同一であるかまたは異なり、NR1、COO-、O、S、Se、Te、SO、SeO、TeO、SO2、SeO2、TeO2、R1SO、R1SeO、R1TeO、R1SO2、R1SeO2、R1TeO2、R1POまたは(R1)2POであり;
cは、出現する毎に同一であるかまたは異なり、0または1である。
Ligは、出現する毎に同一であるかまたは異なり、中性またはモノアニオン性の、一座または二座配位子であり、たとえばハロゲン化物または水酸化物であり;
pは、出現する毎に同一であるかまたは異なり、1、2、3、4または5であり、式(47)および式(49)におけるpは金属Mの価数を示しており;
qは、出現する毎に同一であるかまたは異なり、0、1、2、3または4であり、好ましくは0、1または2であり;
ここでの式(48)の化合物も荷電していてもよいし対イオンを含んでいてもよい。
以下の合成は、特段記載していない限り、保護ガス雰囲気下で、乾燥溶媒中において行われる。溶媒および試薬は、ALDRICHまたはABCRから購入できる。以下のような前駆体が調製され得る:WO 98/22148に従ってトリス(2−ブロモ−6−ピリジル)ホスフィンおよびトリス(2−ブロモ−6−ピリジル)メタノール;WO 04/081017に従ってトリス(2−ブロモ−6−ピリジル)ホスフィンオキシド、トリス(2−ブロモ−6−ピリジル)フルオロメタンおよびトリス(2−メチル−6−ピリジル)フルオロメタン; Heteroatomic Chemistry 1990, 1 (4), 295 に従ってトリス(2−メチル−6ピリジル)ホスフィン;Heteroatomic Chemistry 1997, 8 (5), 439 に従ってトリス(2−メチル−6−ピリジル)ホスフィンオキシド; J. Am. Chem. Soc. 1999, 121 (47), 11007 に従ってトリス(2−メチル−6−ピリジル)メタン; Inorg. Chem. 2003, 42 (4), 11993 に従って1,1,1−トリス(2−メチル−6−ピリジル)エタン; Tetrahedron Letters 1998, 39 (4), 8509に従ってトリス((2−メチル−6−ピリジル)メタノール; Inorg. Chem. 2000, 39 (2), 226 に従ってトリス(2−ブロモ−6−ピリジル)メチルメチルエーテルおよびそれに類似のトリス(2−メチル−6−ピリジル)メチルメチルエーテル;WO 06/018202に従ってナトリウムジクロロビスアセチルアセトナートイリデート(III)。
2.74g(5mmol)のトリス(2−(フェニルメチル)−6−ピリジル)メチルメチルエーテルおよび2.42g(5mmol)のナトリウムジクロロビスアセチルアセトナートイリデート(III)を20mlのエチレングリコール中に懸濁した懸濁液を170℃で20時間にわたって加熱する。冷却後、混合物を100mlの水で希釈し、水溶液相を各回50mlのジクロロメタンを用いて3回抽出し、有機相を硫酸マグネシウムで乾燥させて脱水し、残留物をシリカゲル上でジクロロメタンを用いてクロマトグラフし、最後にジクロロメタン/メタノールから再結晶する。収量および収率:1.23g、33.6%;純度:NMRによれば>99.5%。
2.74g(5mmol)のトリス(2−(フェニルメチル)−6−ピリジル)メチルメチルエーテルおよび1.49g(5mmol)の塩化イリジウム(III)水素化物を75mlの2−エトキシエタノールと25mlの水との混合物中に懸濁した懸濁液を還流下で20時間にわたって加熱する。冷却後、混合物を100mlの水で希釈し、沈降物を濾過し、この沈降物を20mlのメタノールで3回洗浄し乾燥させる。このようにして得られた固形物を50mlのジエチレングリコールジメチルエーテル中に懸濁させ、2.57g(10mmol)のトリフルオロメタンスルホン酸銀(I)を添加し、混合物を110℃で5時間にわたって攪拌する。冷却後、混合物を100mlの水で希釈し、水溶液相を各回50mlのジクロロメタンを用いて3回洗浄し、有機相を硫酸マグネシウム上で乾燥させて脱水し、残留物をシリカゲル上でジクロロメタンを用いてクロマトグラフし、最後にジクロロメタン/メタノールから再結晶する。収量および収率:0.97g、21.0%;純度:NMRによれば>99.5%。
OLEDは以下に概略する一般的なプロセスによって製造される。これはもちろん各場合における特定の状況に適合させなければならない(たとえば最適な効率または色を達成するための層厚さの変更)。
ITO被覆した基板(たとえばガラスサポート、PETフィルム)を正確な大きさに裁断した後、それらを複数の清浄化工程において超音波浴(たとえば石鹸水、Millipore water、イソプロパノール)で清浄化する。それらをN2ガンでの吹き付けにより乾燥させデシケータ内で保管する。有機層で蒸気被覆する前に、それらに対し約20分間にわたってオゾンプラズマデバイスによる処理を施す。第1有機層として高分子正孔注入層を使用することが賢明であろう。これは一般には共役導電性ポリマー、たとえば、ポリアニリン誘導体(PANI)またはポリチオフェン誘導体(たとえばBAYYERからのPEDOT、BAYTRON P(登録商標))である。次にこれをスピンコートによって塗布する。複数の有機層を高真空ユニット内で蒸着することにより連続的に塗布する。それぞれの層の膜厚および蒸着速度は水晶共振器によってモニターして調整する。また、各層を1種よりも多種の化合物で構成することも可能である。すなわち概して述べると、ホスト材料にゲスト材料をドープしてもよい。これは2つ以上のソースからの共蒸着によって達成される。次に、電極が先の有機層に塗布される。これは一般に熱蒸着法(Balzer BA360またはPfeiffer PL S 500)によって行われる。続いて、アノードとしての透明なITO電極とカソードとしての金属電極とを接続してデバイスのパラメータを決定する。
HIM1 20nmの2,2’,7,7’−テトラキス(ジ−p−トリルアミノ)スピロ−9,9’−ビフルオレン(蒸着する)
NPB 20nmの4,4’−ビス(1−ナフチルフェニルアミノ)ビフェニル(蒸着する)
mCP 20nmの1,3−ビス(N−カルバゾルイル)ベンゼン(蒸着する)、10%の三重項エミッタでドープされている
三重項エミッタ 本発明による例 表を参照のこと
BCP 8nmの2,9−ジメチル−4,7−ジフェニル−1,10−フェナントロリン(蒸着する)
AlQ3 20nm(蒸着する)
Li/Al 表面上にカソードとして設ける5nmのLiF、150nmのAl。
Claims (15)
- 式(1)の化合物であって、
Vは、配位子部分L1、L2およびL3を互いに共有結合する、第3、第4、第5および/または第6主族からの1個ないし80個の原子を含む架橋ユニットであり;
aは0または1であり、a=0である場合、前記架橋ユニットVは存在せず;
L1は式(3)の配位子部分であり、
Zは、出現する毎に同一であるかまたは異なり、第3、第4、第5または第6主族からの置換されたまたは未置換の原子であって、前記環Cy1とCy2とを架橋しており;
D1、D2は、出現する毎に同一であるかまたは異なり、少なくとも1個のドナー原子を含む化学基を表している。 - 請求項1または2に記載の化合物であって、その配位子部分L1に、式(11)の金属および架橋ユニットVとともに下記が適用されることを特徴とする化合物。
Cy1、Cy2は、出現する毎に同一であるかまたは異なり、5個ないし30個の芳香族環原子を有し、1個以上の基Rで置換されていてもよいアリール基もしくはヘテロアリール基、または環式の飽和のもしくは好ましくは不飽和のカルベンであり;ここで2つの基の一方Cy1またはCy2は、形式的に負に荷電した炭素を介して、または形式的に負に荷電した環外ドナー原子を介して前記金属に結合しており、2つの基Cy1およびCy2の他方は、該基Cy1またはCy2の一部であって、窒素、リンおよびカルベンの形態にある炭素から選択される中性ドナー原子を介して結合しており;
Vは、出現する毎に同一であるかまたは異なり、B、BR-、B(CR2)3、RB(CR2)3 -、B(O)3、RB(O)3 -、B(CR2CR2)3、RB(CR2CR2)3 -、B(CR2O)3、RB(CR2O)3 -、B(OCR2)3、RB(OCR2)3 -、Al(O)3、RAl(O)3 -、Al(OCR2)3、RAl(OCR2)3 -、CR、CO-、CN(R1)2、RC(CR2)3、RC(O)3、RC(CR2CR2)3、RC(CR2O)3、RC(OCR2)3、RC(SiR2)3、RC(SiR2CR2)3、RC(CR2SiR2)3、RC(SiR2SiR2)3、SiR、RSi(CR2)3、RSi(O)3、RSi(CR2CR2)3、RSi(OCR2)3、RSi(CR2O)3、RSi(SiR2)3、RSi(SiR2CR2)3、RSi(CR2SiR2)3、RSi(SiR2SiR2)3、N、NO、NR+、N(CR2)3、RN(CR2)3 +、N(C=O)3、N(CR2CR2)3、RN(CR2CR2)+、P、RR+、PO、PS、PSe、PTe、P(O)3、PO(O)3、P(OCR2)3、PO(OCR2)3、P(CR2)3、PR(CR2)3 +、PO(CR2)3、P(CR2CR2)3、PR(CR2CR2)3 +、PO(CR2CR2)3、As、AsR+、AsO、AsS、AsSe、AsTe、As(O)3、AsO(O)3、As(OCR2)3、AsO(OCR2)3、As(CR2)3、AsR(CR2)3 +、AsO(CR2)3、As(CR2CR2)3、AsR(CR2CR2)3 +、AsO(CR2CR2)3、Sb、SbR+、SbO、SbS、SbSe、SbTe、Sb(O)3、SbO(O)3、Sb(OCR2)3、SbO(OCR2)3、Sb(CR2)3、SbR(CR2)3 +、SbO(CR2)3、Sb(CR2CR2)3、SbR(CR2CR2)3 +、SbO(CR2CR2)3、Bi、BiR+、BiO、BiS、BiSe、BiTe、Bi(O)3、BiO(O)3、Bi(OCR2)3、BiO(OCR2)3、Bi(CR2)3、BiR(CR2)3 +、BiO(CR2)3、Bi(CR2CR2)3、BiR(CR2CR2)3 +、BiO(CR2CR2)3、S+、S(CR2)3+、S(CR2CR2)3 +、Se+、Se(CR2)3 +、Se(CR2CR2)3 +、Te+、Te(CR2)3 +、Te(CR2CR2)3 +、1位、2位および3位を介してリンクしたシクロプロパン、1位、2位および3位を介してリンクしたアジリジン、もしくは対応する非対称の類似化合物;または、式(12)、(13)もしくは(14)のユニットであり、
Zは、出現する毎に同一であるかまたは異なり、O、S、S(=O)、S(=O)2、NR、PR、P(=O)R、P(=NR)、CR2、C(=O)、C(=NR)、C(=CR2)、SiR2またはBRであり;
Rは、出現する毎に同一であるかまたは異なり、H、D、F、Cl、Br、I、N(R1)2、CN、NO2、Si(R1)3、B(OR1)2、C(=O)R1、P(=O)(R1)2、S(=O)R1、S(=O)2R1、OSO2R1、1個ないし40個のC原子を有する直鎖のアルキル、アルケニル、アルキニル、アルコキシもしくはチオアルコキシ基、または3個ないし40個のC原子を有する分枝鎖もしくは環式のアルキル、アルケニル、アルキニル、アルコキシもしくはチオアルコキシ基(これらの各々は1個以上の基R1によって置換されていてもよく、ここで1個以上の非隣接のCH2基はR1C=CR1、C≡C、Si(R1)2、Ge(R1)2、Sn(R1)2、C=O、C=S、C=Se、C=NR1、P(=O)(R1)、SO、SO2、NR1、O、SまたはCONR1と置換されていてもよく、1個以上のH原子はF、Cl、Br、I、CNまたはNO2と置換されていてもよい)、または5個ないし60個の芳香族環原子を有する芳香族環構造もしくは芳香族複素環構造(これは各例において1個以上の基R1によって置換されていてもよい)、または5個ないし60個の芳香族環原子を有するアリールオキシもしくはヘテロアリールオキシ基(これは1個以上の基R1によって置換されていてもよい)、またはジアリールアミノ基、10個ないし40個の芳香族環原子を有するジヘテロアリールアミノ基もしくはアリールへテロアリールアミノ基(これは1個以上の基R1によって置換されていてもよい)、またはこれらの構造の組み合わせであり;2つ以上の置換基Rは互いに単環式または多環式の脂肪族環構造、芳香族環構造および/またはベンゾ縮合環構造を形成していてもよく;
R1は、出現する毎に同一であるかまたは異なり、H、F、または1個ないし20個のC原子を有する脂肪族、芳香族および/または複素芳香族炭化水素基(更に、1個以上のH原子がFによって置換されていてもよい)であり;2個以上の置換基R1は互いに単環式または多環式の脂肪族環構造または芳香族環構造を形成していてもよく;
aは請求項1で定義した通りである。 - 請求項1ないし3の1項以上に記載された化合物であって、前記配位子部分L1は、前記金属および前記架橋ユニットVとともに、式(15)ないし式(30)の構造を有することを特徴とする化合物。
Eは、出現する毎に同一であるかまたは異なり、C、NまたはPであり;
Qは、出現する毎に同一であるかまたは異なり、O、S、Se、TeまたはNであり;
Tは、出現する毎に同一であるかまたは異なり、N、PまたはCであり;
Aは、出現する毎に同一であるかまたは異なり、NR1、SまたはOであり;
Xは、出現する毎に同一であるかまたは異なり、CR、N若しくはPであり、この場合、式(27)、式(28)、式(29)および式(30)において、カルベン環中の2つの基Xの間に二重結合が存在するか;または式(27)、式(28)、式(29)および式(30)におけるカルベン環中のXは、出現する毎に同一であるかまたは異なり、CR2を表しており;
Yは、出現する毎に同一であるかまたは異なり、NR1、COO-、O、S、Se、Te、SO、SeO、TeO、SO2、SeO2、TeO2、R1SO、R1SeO、R1TeO、R1SO2、R1SeO2、R1TeO2、R1POまたは(R1)2POであり;
cは、出現する毎に同一であるかまたは異なり、0または1である。 - 請求項1ないし4の1項以上に記載の化合物であって、Mはタングステン、レニウム、ルテニウム、オスミウム、ロジウム、イリジウム、白金、金、スカンジウム、イットリウム、ランタン、アルミニウム、ガリウムまたはインジウムを表していることを特徴とする化合物。
- 請求項1ないし5の1項以上に記載の化合物であって、Zは出現する毎に同一であるかまたは異なり、O、S、NR、CR2、C(=O)またはC(=CR2)を表していることを特徴とする化合物。
- 請求項1ないし6の1項以上に記載の化合物であって、VはB、 BR-、CR、CO-、CN(R1)2、SiR、N、NO、NR+、P、PR+、PO、PS、As、AsO、AsS、Sb、SbO、SbS、S+またはSe+を表していることを特徴とする化合物。
- 請求項1ないし7の1項以上に記載の化合物であって、式(5)の前記配位子部分中の前記基D1およびD2における前記ドナー原子は窒素、リン、酸素および硫黄から選択されることを特徴とする化合物
- 請求項1ないし8の1項以上に記載の化合物であって、式(5)の前記配位子部分は置換または未置換のβ−ケトケトネート、β−ケトエステル、β−ジエステル、アミノカルボン酸から誘導されるカルボキシレート、イミノアセトアセトナート、ヒドロオキサメート、ピリジルホスフィン、α−ホスフィノカルボキシレート、グリコールエーテル、エーテルアルコラート、ジアルコールから誘導されるジアルコラート、ジチオールから誘導されるジチオラート、ジアミン、イミン、ジイミン、ジホスフィンおよびサリチルイミンから誘導されるサリチルイミネートから選択されることを特徴とする化合物。
- 請求項1ないし9の1項以上に記載の化合物の調製方法であって、式(2)の配位子またはこれらの配位子の前駆体の、式(47)の金属アルコキシドとの、式(48)の金属ケトケトネートとの、または式(49)の金属ハロゲン化物との反応による方法。
Halは、出現する毎に同一であるかまたは異なり、F、Cl、BrまたはIであり;
Ligは、出現する毎に同一であるかまたは異なり、中性またはモノアニオン性の、一座または二座配位子であり、たとえばハロゲン化物または水酸化物であり;
pは、出現する毎に同一であるかまたは異なり、1、2、3、4または5であり、式(47)および式(49)におけるpは金属Mの価数を示しており;
qは、出現する毎に同一であるかまたは異なり、0、1、2、3または4であり、好ましくは0、1または2であり;
ここで式(48)の化合物も荷電していてもよく、対イオンを含んでいてもよい。 - 請求項1ないし9の1項以上に記載の1種以上の化合物を含むオリゴマー、ポリマーまたはデンドリマーであって、式(1)の錯体から該ポリマー、該オリゴマーまたは該デンドリマーへの1つ以上の結合が存在しているオリゴマー、ポリマーまたはデンドリマー。
- 請求項1ないし9または請求項12のうちの1項以上に記載の化合物の、電子部品における使用。
- 請求項1ないし9または請求項12の1項以上に記載の1種以上の化合物を含む電子部品、特に有機集積回路(O−IC)、有機電界効果トランジスタ(O-FET)、有機薄膜トランジスタ(O−TFT)、有機発光トランジスタ(O−LET)、有機太陽電池(O-SC)、有機光学検出器、有機フォトレセプタ、有機電界クエンチデバイス(O−FQD)、発光電気化学電池(LEC)または有機レーザーダイオード(O−laser)、特に有機エレクトロルミネセンス素子(OLED、PLED)。
- 請求項14に記載の有機エレクトロルミネセンス素子であって、請求項1ないし9の1項以上に記載された化合物が発光層における発光化合物として、好ましくはマトリックス材料と組み合わせて用いられる、または請求項1ないし9の1項以上に記載された化合物が発光層における発光化合物のためのマトリックス材料として、好ましくは燐光発光化合物のためのマトリックス材料として用いられる、または請求項1ないし9の1項以上に記載された化合物が正孔障壁層における正孔障壁材料としておよび/または電子輸送層における電子輸送材料として用いられることを特徴とする有機エレクトロルミネセンス素子。
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CN101981043B (zh) | 2014-11-05 |
US20110012100A1 (en) | 2011-01-20 |
DE102008015526A1 (de) | 2009-10-01 |
DE102008015526B4 (de) | 2021-11-11 |
US8617723B2 (en) | 2013-12-31 |
KR20100128339A (ko) | 2010-12-07 |
CN101981043A (zh) | 2011-02-23 |
EP2254896A1 (de) | 2010-12-01 |
TW201002726A (en) | 2010-01-16 |
KR101711664B1 (ko) | 2017-03-02 |
JP5705719B2 (ja) | 2015-04-22 |
WO2009118087A1 (de) | 2009-10-01 |
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