JP2016034935A - 6員配位環を有する三座シクロメタル化金属錯体 - Google Patents
6員配位環を有する三座シクロメタル化金属錯体 Download PDFInfo
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- JP2016034935A JP2016034935A JP2015148801A JP2015148801A JP2016034935A JP 2016034935 A JP2016034935 A JP 2016034935A JP 2015148801 A JP2015148801 A JP 2015148801A JP 2015148801 A JP2015148801 A JP 2015148801A JP 2016034935 A JP2016034935 A JP 2016034935A
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- Prior art keywords
- substituted
- aryl
- group
- independently
- alkenyl
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- 229910052751 metal Inorganic materials 0.000 title abstract description 16
- 239000002184 metal Substances 0.000 title abstract description 15
- 125000003118 aryl group Chemical group 0.000 claims description 100
- 125000000217 alkyl group Chemical group 0.000 claims description 87
- 125000003342 alkenyl group Chemical group 0.000 claims description 61
- 125000000304 alkynyl group Chemical group 0.000 claims description 61
- 229910052739 hydrogen Inorganic materials 0.000 claims description 53
- 239000001257 hydrogen Substances 0.000 claims description 53
- -1 NR 2a Inorganic materials 0.000 claims description 52
- 125000001072 heteroaryl group Chemical group 0.000 claims description 49
- 229910052736 halogen Inorganic materials 0.000 claims description 44
- 150000002367 halogens Chemical class 0.000 claims description 44
- 125000003545 alkoxy group Chemical group 0.000 claims description 41
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 33
- 229910052760 oxygen Inorganic materials 0.000 claims description 32
- 229910052717 sulfur Inorganic materials 0.000 claims description 31
- 229910052799 carbon Inorganic materials 0.000 claims description 30
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 25
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 17
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 12
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 10
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 150000003222 pyridines Chemical class 0.000 claims description 7
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 6
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 6
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 6
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 6
- 238000004020 luminiscence type Methods 0.000 claims description 4
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 claims description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 3
- 150000003003 phosphines Chemical class 0.000 claims description 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims 19
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 8
- 238000005286 illumination Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 50
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 35
- 239000000463 material Substances 0.000 description 34
- 0 CC(C)[C@](*)C=CCc(cc1)ccc1*(C)=*C Chemical compound CC(C)[C@](*)C=CCc(cc1)ccc1*(C)=*C 0.000 description 32
- 125000000753 cycloalkyl group Chemical group 0.000 description 31
- 150000003573 thiols Chemical class 0.000 description 25
- 125000001424 substituent group Chemical group 0.000 description 24
- 125000000392 cycloalkenyl group Chemical group 0.000 description 23
- 238000000034 method Methods 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 12
- 230000005281 excited state Effects 0.000 description 10
- 150000004820 halides Chemical class 0.000 description 10
- 239000003446 ligand Substances 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 230000003287 optical effect Effects 0.000 description 10
- 125000005842 heteroatom Chemical group 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 6
- 230000003111 delayed effect Effects 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 238000012545 processing Methods 0.000 description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 150000001540 azides Chemical class 0.000 description 5
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 125000003636 chemical group Chemical group 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 239000010931 gold Substances 0.000 description 4
- 230000005283 ground state Effects 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 230000005693 optoelectronics Effects 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 238000000103 photoluminescence spectrum Methods 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 239000010948 rhodium Substances 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 150000004696 coordination complex Chemical class 0.000 description 3
- 125000004366 heterocycloalkenyl group Chemical group 0.000 description 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 239000003550 marker Substances 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 229920001281 polyalkylene Polymers 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 2
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 2
- UVHIWKCVGUMHNB-UHFFFAOYSA-N 5,7-dihydroindolo[2,3-b]carbazole Chemical compound N1C2=CC=CC=C2C2=C1C=C1NC3=CC=CC=C3C1=C2 UVHIWKCVGUMHNB-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 125000002015 acyclic group Chemical group 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 2
- 125000005233 alkylalcohol group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000005347 biaryls Chemical group 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 238000000295 emission spectrum Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- SBOJXQVPLKSXOG-UHFFFAOYSA-N o-amino-hydroxylamine Chemical compound NON SBOJXQVPLKSXOG-UHFFFAOYSA-N 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
- 150000003057 platinum Chemical class 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000011970 polystyrene sulfonate Substances 0.000 description 2
- 229960002796 polystyrene sulfonate Drugs 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 1
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- HTJMXYRLEDBSLT-UHFFFAOYSA-N 1,2,4,5-tetrazine Chemical compound C1=NN=CN=N1 HTJMXYRLEDBSLT-UHFFFAOYSA-N 0.000 description 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 description 1
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 1
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
- ZCJJIQHVZCFSGZ-UHFFFAOYSA-N 2,8-bis(diphenylphosphoryl)dibenzothiophene Chemical compound C=1C=CC=CC=1P(C=1C=C2C3=CC(=CC=C3SC2=CC=1)P(=O)(C=1C=CC=CC=1)C=1C=CC=CC=1)(=O)C1=CC=CC=C1 ZCJJIQHVZCFSGZ-UHFFFAOYSA-N 0.000 description 1
- RIKNNBBGYSDYAX-UHFFFAOYSA-N 2-[1-[2-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]-n,n-bis(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C(=CC=CC=1)C1(CCCCC1)C=1C(=CC=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 RIKNNBBGYSDYAX-UHFFFAOYSA-N 0.000 description 1
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- UKSYHCXTHZWLFM-UHFFFAOYSA-N 5,7-dipyridin-2-ylindolo[2,3-b]carbazole Chemical compound N1=CC=CC=C1N1C2=CC(N(C=3N=CC=CC=3)C=3C4=CC=CC=3)=C4C=C2C2=CC=CC=C21 UKSYHCXTHZWLFM-UHFFFAOYSA-N 0.000 description 1
- ADLVDYMTBOSDFE-UHFFFAOYSA-N 5-chloro-6-nitroisoindole-1,3-dione Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC2=C1C(=O)NC2=O ADLVDYMTBOSDFE-UHFFFAOYSA-N 0.000 description 1
- CUQGKGMUSQKHFO-UHFFFAOYSA-N 9-(6-carbazol-9-ylpyridin-2-yl)carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=N1 CUQGKGMUSQKHFO-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 229910004373 HOAc Inorganic materials 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
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- 239000002246 antineoplastic agent Substances 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000006309 butyl amino group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
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- 239000003054 catalyst Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001245 hexylamino group Chemical group [H]N([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 125000006316 iso-butyl amino group Chemical group [H]N(*)C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 125000002463 lignoceryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000382 optic material Substances 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004894 pentylamino group Chemical group C(CCCC)N* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000006308 propyl amino group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 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
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
- 230000005428 wave function Effects 0.000 description 1
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- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
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Abstract
Description
[0001]本出願は、「6員配位環を有する三座シクロメタル化金属錯体」と題された2014年7月28日出願の米国出願第62/029,737号に対する優先権を主張するものであり、その全部を本明細書中に援用する。
技術分野
[0002]本明細書の開示は、6員配位環を有する三座シクロメタル化金属錯体に関するものである。
[0002]光を吸収及び/又は放射することができる化合物は、例えば、太陽光感知デバイス及び感光デバイスなどの光吸収デバイス、有機発光ダイオード(OLED)、光放射デバイス、又は光の吸収及び放射が可能なデバイスを含めた、多種多様な光学デバイス及びエレクトロルミネセントデバイスにおける使用、並びにバイオ用途のマーカーとしての使用に理想的に適している可能性がある。多くの研究が、光学及びエレクトロルミネセンスデバイスにおいて使用するための有機及び有機金属材料の発見と最適化に向けられている。一般にこの分野における研究は、吸収及び発光効率の向上、及びデバイスの安定性の向上、並びに処理能力の向上などの複数の目標を達成することを目的としている。
[0005]本明細書の開示は、有機発光ダイオード(OLED)、ディスプレイ、及び照明用途において発光体として用いるのに好適な金属錯体に関するものである。
Mは、Pt(II)、Pd(II)、Ir(I)、Rh(I)、又はAu(II)であり;
x=0又は1であり、x=0の場合にはY3eはY3bに直接結合しており;
y=0又は1であり、y=0の場合にはY2aはY4bに直接結合しており;
z=0又は1であり、m=0の場合にはY2cはY2dに直接結合しており;
Ar1、Ar2、及びAr3のそれぞれは、独立して5員のヘテロアリール又は6員のアリール若しくはヘテロアリールを表し;
それぞれのnは、価数が許すならば独立して1〜4の整数であり;
それぞれのR1、R2、及びR3は、独立して、水素、ハロゲン、ヒドロキシル、アミノ、ニトロ、チオール、又は置換若しくは非置換のアルキル、アルコキシル、アルケニル、アルキニル、ヘテロアリール、又はアリールであり、R1の任意の2つ、R2の任意の2つ、及びR3の任意の2つは、場合によっては結合しており;
Y1aは、O、S、NR2a、C、CR2a、CR2bR2c、PR2a、AsR2a、BR2a、又はSiR2dR2eであり、ここで、R2a、R2b、R2c、R2d、及びR2eのそれぞれは、独立して、水素、ハロゲン、又は置換若しくは非置換のアルキル、アルケニル、アルキニル、又はアリールであり;
Y1bは、O、S、NR3a、C、CR3a、CR3bR3c、PR2a、AsR2a、BR2a、P(O)R2a、As(O)R2a、又はSiR3dR3eであり、ここで、R3a、R3b、R3c、R3d、及びR3eのそれぞれは、独立して、水素、ハロゲン、又は置換若しくは非置換のアルキル、アルケニル、アルキニル、又はアリールであり;
Y2a及びY2dのそれぞれは、独立して、C、N、NR4a、又はCR4bであり、ここで、R4a及びR4bのそれぞれは、独立して、水素、ヒドロキシル、アミノ、ニトロ、チオール、又は置換若しくは非置換のC1〜C4アルキル、アルコキシ、又はアリールであり;
Y2b及びY2cのそれぞれは、独立してC又はNであり;
Y3a、Y3b、Y3c、Y3d、及びY3eのそれぞれは、独立して、C、N、O、S、NR5a、PR5b、AsR5c、SiR5dR5e、BR5f、又はCR5gであり、ここで、R5a、R5b、R5c、R5d、R5e、R5f、及びR5gのそれぞれは、独立して、水素、又は置換若しくは非置換のC1〜C4アルキル、又はアリール;或いはZR6aR6bであり;ZはC又はSiであり;R6a及びR6bのそれぞれは、独立して置換若しくは非置換のC1〜C4アルキル、又はアリールであり;
Y4a、Y4b、Y4c、及びY4dのそれぞれは、独立して、N、NR4e、C、又はCR4fであり、ここで、R4e及びR4fのそれぞれは、独立して、水素、ヒドロキシル、アミノ、ニトロ、チオール、又は置換若しくは非置換のC1〜C4アルキル、アルコキシ、又はアリールであり;
L1、L2、L3、及びL4のそれぞれは、独立して存在するか又は存在せず、存在する場合には、それぞれは独立して、置換若しくは非置換の5員のヘテロアリール、6員のアリール、6員のヘテロアリール、又はこれらの任意の縮合した組み合わせを表し;
Yは、ハロゲン、OCOR7a、OR7b、SR7c、NR7dR7e、CO、NR7f、PR7g、AsR7hR7iR7j、C≡CR7k;置換若しくは非置換のピリジン、イミダゾール、ピラゾール、オキサゾール、チアゾール、イソオキサゾール、又はキノリンであり;ここで、R7a、R7b、R7c、R7d、R7e、R7f、R7g、R7h、R7i、R7j、及びR7kのそれぞれは、独立して、アセチルアセトネート、ピリジン、イミダゾール;置換若しくは非置換のアルキル、アルケニル、アルキニル、アリール、又は三置換ホスフィンである)
の錯体が開示される。
[0018]本開示は、以下の詳細な説明及びそれに含まれる実施例を参照することによってより容易に理解することができる。
Mは、Pt(II)、Pd(II)、Ir(I)、Rh(I)、又はAu(II)であり;
x=0又は1であり、x=0の場合にはY3eはY3bに直接結合しており;
y=0又は1であり、y=0の場合にはY2aはY4bに直接結合しており;
z=0又は1であり、m=0の場合にはY2cはY2dに直接結合しており;
Ar1、Ar2、及びAr3のそれぞれは、独立して5員のヘテロアリール又は6員のアリール若しくはヘテロアリールを表し;
それぞれのnは、価数が許すならば独立して1〜4の整数であり;
それぞれのR1、R2、及びR3は、独立して、水素、ハロゲン、ヒドロキシル、アミノ、ニトロ、チオール、又は置換若しくは非置換のアルキル、アルコキシル、アルケニル、アルキニル、ヘテロアリール、又はアリールであり、R1の任意の2つ、R2の任意の2つ、及びR3の任意の2つは、場合によっては結合しており;
Y1aは、O、S、NR2a、C、CR2a、CR2bR2c、PR2a、AsR2a、BR2a、又はSiR2dR2eであり、ここで、R2a、R2b、R2c、R2d、及びR2eのそれぞれは、独立して、水素、ハロゲン、又は置換若しくは非置換のアルキル、アルケニル、アルキニル、又はアリールであり;
Y1bは、O、S、NR3a、C、CR3a、CR3bR3c、PR2a、AsR2a、BR2a、P(O)R2a、As(O)R2a、又はSiR3dR3eであり、ここで、R3a、R3b、R3c、R3d、及びR3eのそれぞれは、独立して、水素、ハロゲン、又は置換若しくは非置換のアルキル、アルケニル、アルキニル、又はアリールであり;
Y2a及びY2dのそれぞれは、独立して、C、N、NR4a、又はCR4bであり、ここで、R4a及びR4bのそれぞれは、独立して、水素、ヒドロキシル、アミノ、ニトロ、チオール、又は置換若しくは非置換のC1〜C4アルキル、アルコキシ、又はアリールであり;
Y2b及びY2cのそれぞれは、独立してC又はNであり;
Y3a、Y3b、Y3c、Y3d、及びY3eのそれぞれは、独立して、C、N、O、S、NR5a、PR5b、AsR5c、SiR5dR5e、BR5f、又はCR5gであり、ここで、R5a、R5b、R5c、R5d、R5e、R5f、及びR5gのそれぞれは、独立して、水素、又は置換若しくは非置換のC1〜C4アルキル、又はアリール;或いはZR6aR6bであり;ZはC又はSiであり;R6a及びR6bのそれぞれは、独立して置換若しくは非置換のC1〜C4アルキル、又はアリールであり;
Y4a、Y4b、Y4c、及びY4dのそれぞれは、独立して、N、NR4e、C、又はCR4fであり、ここで、R4e及びR4fのそれぞれは、独立して、水素、ヒドロキシル、アミノ、ニトロ、チオール、又は置換若しくは非置換のC1〜C4アルキル、アルコキシ、又はアリールであり;
L1、L2、L3、及びL4のそれぞれは、独立して存在するか又は存在せず、存在する場合には、それぞれは独立して、置換若しくは非置換の5員のヘテロアリール、6員のアリール、6員のヘテロアリール、又はこれらの任意の縮合した組み合わせを表し;
Yは、ハロゲン、OCOR7a、OR7b、SR7c、NR7dR7e、CO、NR7f、PR7g、AsR7hR7iR7j、C≡CR7k;或いは置換若しくは非置換のピリジン、イミダゾール、ピラゾール、オキサゾール、チアゾール、イソオキサゾール、又はキノリンであり;ここで、R7a、R7b、R7c、R7d、R7e、R7f、R7g、R7h、R7i、R7j、及びR7kのそれぞれは、独立して、アセチルアセトネート、ピリジン、イミダゾール、置換若しくは非置換のアルキル、アルケニル、アルキニル、アリール、又は三置換ホスフィンである)
の錯体が開示される。
Xは、O、S、NR、PR、AsR、CR2、SiR2、又はBRであり;
Aは、O、S、NR、PR、AsR、CR2、SiR2、又はBRであり;
Uは、O、S、NR、PR、AsR、CR2、SiR2、又はBRであり;
Mは、Pt(II)又はPd(II)であり;
それぞれのRは、独立して、水素、ハロゲン、置換若しくは非置換のアルキル、アルケニル、アルキニル、及びアリールであり;
Ar1及びAr2のそれぞれは、独立して、置換若しくは非置換の5員のヘテロアリール又は6員のアリール若しくはヘテロアリールを表す)
[0083]
Yは、Cl、Br、I、OR、OCOR、SR、NRR、又はC≡Rであり、
それぞれのRは、独立して、水素、ハロゲン、置換若しくは非置換のアルキル、アルケニル、アルキニル、又はアリールである。
Yは、Cl、Br、I、OR、OCOR、SR、NRR、又はC≡Rであり、
それぞれのR及びR’は、独立して、水素、ハロゲン、置換若しくは非置換のアルキル、アルケニル、アルキニル、又はアリールである。
Yは、CO、NR3、PR3、AsR3、置換若しくは非置換のピリジン、イミダゾール、ピラゾール、オキサゾール、チアゾール、イソオキサゾールであり、
それぞれのRは、独立して、水素、置換若しくは非置換のアルキル、アルケニル、アルキニル、又はアリールである。
Xは、O、S、NR、PR、AsR、CR2、SiR2、又はBRであり;
Aは、O、S、NR、PR、AsR、CR2、SiR2、又はBRであり;
Uは、O、S、NR、PR、AsR、CR2、SiR2、又はBRであり;
Mは、Rh(I)又はIr(I)であり;
それぞれのRは、独立して、水素、ハロゲン、置換若しくは非置換のアルキル、アルケニル、アルキニル、又はアリールであり;
Ar1及びAr2のそれぞれは、独立して、置換若しくは非置換の5員のヘテロアリール又は6員のアリール若しくはヘテロアリールである)
の1つを有する。
Yは、CO、NR3、PR3、AsR3、置換若しくは非置換のピリジン、イミダゾール、又はキノリンであり、
それぞれのRは、独立して、水素、置換若しくは非置換のアルキル、アルケニル、アルキニル、又はアリールである。
Xは、O、S、NR、PR、AsR、CR2、SiR2、又はBRであり;
Aは、O、S、NR、PR、AsR、CR2、SiR2、又はBRであり;
Uは、O、S、NR、PR、AsR、CR2、SiR2、又はBRであり;
Mは、Au(III)であり;
Ar1、Ar2、及びAr3のそれぞれは、独立して、置換若しくは非置換の5員のヘテロアリール又は6員のアリール若しくはヘテロアリールであり、
それぞれのRは、独立して、水素、ハロゲン、置換若しくは非置換のアルキル、アルケニル、アルキニル、又はアリールである)
の1つを有する。
Yは、Cl、Br、I、OR、OCOR、SR、NRR、又はC≡Rであり、
それぞれのRは、独立して、水素、ハロゲン、置換若しくは非置換のアルキル、アルケニル、アルキニル、又はアリールである。
Claims (20)
- 一般式I:
Mは、Pt(II)、Pd(II)、Ir(I)、Rh(I)、又はAu(II)であり;
x=0又は1であり、x=0の場合にはY3eはY3bに直接結合しており;
y=0又は1であり、y=0の場合にはY2aはY4bに直接結合しており;
z=0又は1であり、m=0の場合にはY2cはY2dに直接結合しており;
Ar1、Ar2、及びAr3のそれぞれは、独立して5員のヘテロアリール又は6員のアリール若しくはヘテロアリールを表し;
それぞれのnは、価数が許すならば独立して1〜4の整数であり;
それぞれのR1、R2、及びR3は、独立して、水素、ハロゲン、ヒドロキシル、アミノ、ニトロ、チオール、又は置換若しくは非置換のアルキル、アルコキシル、アルケニル、アルキニル、ヘテロアリール、又はアリールであり、R1の任意の2つ、R2の任意の2つ、及びR3の任意の2つは、場合によっては結合しており;
Y1aは、O、S、NR2a、C、CR2a、CR2bR2c、PR2a、AsR2a、BR2a、又はSiR2dR2eであり、ここで、R2a、R2b、R2c、R2d、及びR2eのそれぞれは、独立して、水素、ハロゲン、又は置換若しくは非置換のアルキル、アルケニル、アルキニル、又はアリールであり;
Y1bは、O、S、NR3a、C、CR3a、CR3bR3c、PR2a、AsR2a、BR2a、P(O)R2a、As(O)R2a、又はSiR3dR3eであり、ここで、R3a、R3b、R3c、R3d、及びR3eのそれぞれは、独立して、水素、ハロゲン、又は置換若しくは非置換のアルキル、アルケニル、アルキニル、又はアリールであり;
Y2a及びY2dのそれぞれは、独立して、C、N、NR4a、又はCR4bであり、ここで、R4a及びR4bのそれぞれは、独立して、水素、ヒドロキシル、アミノ、ニトロ、チオール、又は置換若しくは非置換のC1〜C4アルキル、アルコキシ、又はアリールであり;
Y2b及びY2cのそれぞれは、独立してC又はNであり;
Y3a、Y3b、Y3c、Y3d、及びY3eのそれぞれは、独立して、C、N、O、S、NR5a、PR5b、AsR5c、SiR5dR5e、BR5f、又はCR5gであり、ここで、R5a、R5b、R5c、R5d、R5e、R5f、及びR5gのそれぞれは、独立して、水素、又は置換若しくは非置換のC1〜C4アルキル、又はアリール;或いはZR6aR6bであり;ZはC又はSiであり;R6a及びR6bのそれぞれは、独立して置換若しくは非置換のC1〜C4アルキル、又はアリールであり;
Y4a、Y4b、Y4c、及びY4dのそれぞれは、独立して、N、NR4e、C、又はCR4fであり、ここで、R4e及びR4fのそれぞれは、独立して、水素、ヒドロキシル、アミノ、ニトロ、チオール、又は置換若しくは非置換のC1〜C4アルキル、アルコキシ、又はアリールであり;
L1、L2、L3、及びL4のそれぞれは、独立して存在するか又は存在せず、存在する場合には、それぞれは独立して、置換若しくは非置換の5員のヘテロアリール、6員のアリール、6員のヘテロアリール、又はこれらの任意の縮合した組み合わせを表し;
Yは、ハロゲン、OCOR7a、OR7b、SR7c、NR7dR7e、CO、NR7f、PR7g、AsR7hR7iR7j、C≡CR7k;置換若しくは非置換のピリジン、イミダゾール、ピラゾール、オキサゾール、チアゾール、イソオキサゾール、又はキノリンであり;ここで、R7a、R7b、R7c、R7d、R7e、R7f、R7g、R7h、R7i、R7j、及びR7kのそれぞれは、独立して、アセチルアセトネート、ピリジン、イミダゾール、又は置換若しくは非置換のアルキル、アルケニル、アルキニル、アリール、又は三置換ホスフィンである)
によって表される錯体。 - 請求項1〜14のいずれか1項に記載の錯体を含む発光デバイス。
- 請求項1〜14のいずれか1項に記載の錯体を含むOLEDデバイス。
- リン光OLEDデバイスである、請求項16に記載のOLEDデバイス。
- 請求項1〜14のいずれか1項に記載の錯体を含む光起電力デバイス。
- 請求項1〜14のいずれか1項に記載の錯体を含むルミネセンスディスプレイデバイス。
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2015
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- 2015-07-28 JP JP2015148801A patent/JP6595834B2/ja active Active
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JP2016216448A (ja) * | 2015-05-20 | 2016-12-22 | 株式会社半導体エネルギー研究所 | 有機金属錯体、発光素子、発光装置、電子機器、および照明装置 |
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US9502671B2 (en) | 2016-11-22 |
US9985224B2 (en) | 2018-05-29 |
JP6595834B2 (ja) | 2019-10-23 |
US20170125708A1 (en) | 2017-05-04 |
US10411202B2 (en) | 2019-09-10 |
US20160028029A1 (en) | 2016-01-28 |
US10964897B2 (en) | 2021-03-30 |
US20180277777A1 (en) | 2018-09-27 |
US20200006678A1 (en) | 2020-01-02 |
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