CN107805264A - New organo-metallic compound and utilize its organic illuminating element - Google Patents
New organo-metallic compound and utilize its organic illuminating element Download PDFInfo
- Publication number
- CN107805264A CN107805264A CN201710804805.5A CN201710804805A CN107805264A CN 107805264 A CN107805264 A CN 107805264A CN 201710804805 A CN201710804805 A CN 201710804805A CN 107805264 A CN107805264 A CN 107805264A
- Authority
- CN
- China
- Prior art keywords
- mentioned
- manufacture
- layer
- compound
- organo
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000002902 organometallic compounds Chemical class 0.000 title claims abstract description 36
- 150000001875 compounds Chemical class 0.000 claims description 60
- 239000000126 substance Substances 0.000 claims description 48
- -1 nitro, amino Chemical group 0.000 claims description 44
- 239000005416 organic matter Substances 0.000 claims description 35
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 239000002019 doping agent Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 238000006467 substitution reaction Methods 0.000 claims description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 6
- 229910052805 deuterium Inorganic materials 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 229910052741 iridium Inorganic materials 0.000 claims description 5
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical group [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000010936 titanium Substances 0.000 claims description 5
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- 229910052719 titanium Inorganic materials 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052735 hafnium Inorganic materials 0.000 claims description 2
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052762 osmium Inorganic materials 0.000 claims description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 2
- VSZWPYCFIRKVQL-UHFFFAOYSA-N selanylidenegallium;selenium Chemical compound [Se].[Se]=[Ga].[Se]=[Ga] VSZWPYCFIRKVQL-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 description 181
- 239000010410 layer Substances 0.000 description 121
- 238000000034 method Methods 0.000 description 121
- 239000000463 material Substances 0.000 description 31
- 230000015572 biosynthetic process Effects 0.000 description 27
- 238000003786 synthesis reaction Methods 0.000 description 26
- 229940125904 compound 1 Drugs 0.000 description 24
- 229910052799 carbon Inorganic materials 0.000 description 23
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 22
- 238000002347 injection Methods 0.000 description 18
- 239000007924 injection Substances 0.000 description 18
- 239000000758 substrate Substances 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 230000005540 biological transmission Effects 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 12
- 230000027756 respiratory electron transport chain Effects 0.000 description 11
- 125000000217 alkyl group Chemical group 0.000 description 10
- 238000001704 evaporation Methods 0.000 description 10
- PCMMSLVJMKQWMQ-UHFFFAOYSA-N 2,4-dibromopyridine Chemical class BrC1=CC=NC(Br)=C1 PCMMSLVJMKQWMQ-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 239000004411 aluminium Substances 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 150000004982 aromatic amines Chemical class 0.000 description 6
- 125000000707 boryl group Chemical group B* 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 239000010405 anode material Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 5
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 150000004696 coordination complex Chemical class 0.000 description 4
- 238000004770 highest occupied molecular orbital Methods 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000007738 vacuum evaporation Methods 0.000 description 4
- LSZMVESSGLHDJE-UHFFFAOYSA-N 2-bromo-4-methylpyridine Chemical class CC1=CC=NC(Br)=C1 LSZMVESSGLHDJE-UHFFFAOYSA-N 0.000 description 3
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 125000005018 aryl alkenyl group Chemical group 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 239000010408 film Substances 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
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 229910052733 gallium Inorganic materials 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 125000002971 oxazolyl group Chemical group 0.000 description 3
- 229960003540 oxyquinoline Drugs 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 238000005240 physical vapour deposition Methods 0.000 description 3
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 125000005504 styryl group Chemical group 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-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
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 150000005762 2-bromopyridine Chemical class 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N CHCl3 Substances ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 2
- LWLSVNFEVKJDBZ-UHFFFAOYSA-N N-[4-(trifluoromethoxy)phenyl]-4-[[3-[5-(trifluoromethyl)pyridin-2-yl]oxyphenyl]methyl]piperidine-1-carboxamide Chemical compound FC(OC1=CC=C(C=C1)NC(=O)N1CCC(CC1)CC1=CC(=CC=C1)OC1=NC=C(C=C1)C(F)(F)F)(F)F LWLSVNFEVKJDBZ-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000001769 aryl amino group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical compound C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 2
- 229940049706 benzodiazepine Drugs 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 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 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 125000003003 spiro group Chemical group 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical group [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 2
- 125000001425 triazolyl group Chemical group 0.000 description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 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 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 1
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- GOXICVKOZJFRMB-UHFFFAOYSA-N (3-phenylphenyl)boronic acid Chemical class OB(O)C1=CC=CC(C=2C=CC=CC=2)=C1 GOXICVKOZJFRMB-UHFFFAOYSA-N 0.000 description 1
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 1
- XPEIJWZLPWNNOK-UHFFFAOYSA-N (4-phenylphenyl)boronic acid Chemical class C1=CC(B(O)O)=CC=C1C1=CC=CC=C1 XPEIJWZLPWNNOK-UHFFFAOYSA-N 0.000 description 1
- UVNPEUJXKZFWSJ-LMTQTHQJSA-N (R)-N-[(4S)-8-[6-amino-5-[(3,3-difluoro-2-oxo-1H-pyrrolo[2,3-b]pyridin-4-yl)sulfanyl]pyrazin-2-yl]-2-oxa-8-azaspiro[4.5]decan-4-yl]-2-methylpropane-2-sulfinamide Chemical compound CC(C)(C)[S@@](=O)N[C@@H]1COCC11CCN(CC1)c1cnc(Sc2ccnc3NC(=O)C(F)(F)c23)c(N)n1 UVNPEUJXKZFWSJ-LMTQTHQJSA-N 0.000 description 1
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OTEKOJQFKOIXMU-UHFFFAOYSA-N 1,4-bis(trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=C(C(Cl)(Cl)Cl)C=C1 OTEKOJQFKOIXMU-UHFFFAOYSA-N 0.000 description 1
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004782 1-naphthols Chemical class 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- ZMYIIHDQURVDRB-UHFFFAOYSA-N 1-phenylethenylbenzene Chemical compound C=1C=CC=CC=1C(=C)C1=CC=CC=C1 ZMYIIHDQURVDRB-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- ZHXUWDPHUQHFOV-UHFFFAOYSA-N 2,5-dibromopyridine Chemical class BrC1=CC=C(Br)N=C1 ZHXUWDPHUQHFOV-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- NBYLBWHHTUWMER-UHFFFAOYSA-N 2-Methylquinolin-8-ol Chemical compound C1=CC=C(O)C2=NC(C)=CC=C21 NBYLBWHHTUWMER-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- PJKVFARRVXDXAD-UHFFFAOYSA-N 2-naphthaldehyde Chemical class C1=CC=CC2=CC(C=O)=CC=C21 PJKVFARRVXDXAD-UHFFFAOYSA-N 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 150000005360 2-phenylpyridines Chemical class 0.000 description 1
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- WDBQJSCPCGTAFG-QHCPKHFHSA-N 4,4-difluoro-N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclohexane-1-carboxamide Chemical compound FC1(CCC(CC1)C(=O)N[C@@H](CCN1CCC(CC1)N1C(=NN=C1C)C(C)C)C=1C=NC=CC=1)F WDBQJSCPCGTAFG-QHCPKHFHSA-N 0.000 description 1
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 1
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- ZYASLTYCYTYKFC-UHFFFAOYSA-N 9-methylidenefluorene Chemical compound C1=CC=C2C(=C)C3=CC=CC=C3C2=C1 ZYASLTYCYTYKFC-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KDOKHBNNNHBVNJ-UHFFFAOYSA-N C1=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12.N1C=CC=CC=C1 Chemical compound C1=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12.N1C=CC=CC=C1 KDOKHBNNNHBVNJ-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229940126657 Compound 17 Drugs 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 108010034984 D3 compound Proteins 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- NUGPIZCTELGDOS-QHCPKHFHSA-N N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclopentanecarboxamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CC[C@@H](C=1C=NC=CC=1)NC(=O)C1CCCC1)C NUGPIZCTELGDOS-QHCPKHFHSA-N 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 101100221809 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) cpd-7 gene Proteins 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000004647 alkyl sulfenyl group Chemical group 0.000 description 1
- 125000005360 alkyl sulfoxide group Chemical group 0.000 description 1
- 125000005332 alkyl sulfoxy group Chemical group 0.000 description 1
- 125000005377 alkyl thioxy group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 238000000637 aluminium metallisation Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- HAQFCILFQVZOJC-UHFFFAOYSA-N anthracene-9,10-dione;methane Chemical compound C.C.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 HAQFCILFQVZOJC-UHFFFAOYSA-N 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000005264 aryl amine group Chemical group 0.000 description 1
- 125000005165 aryl thioxy group Chemical group 0.000 description 1
- 125000003609 aryl vinyl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 230000002457 bidirectional effect Effects 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 150000001638 boron Chemical class 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940126543 compound 14 Drugs 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 229940126142 compound 16 Drugs 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000004035 construction material Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- MMUFAGXJPKNAHT-UHFFFAOYSA-N copper;quinolin-8-ol Chemical compound [Cu].C1=CN=C2C(O)=CC=CC2=C1 MMUFAGXJPKNAHT-UHFFFAOYSA-N 0.000 description 1
- SIFHTIHFPPIGBL-UHFFFAOYSA-N ctk2i0750 Chemical class C12=C3C4=CC=CC3=CC=C2C=CC=C1C1=C4CC2=CC=CC=C21 SIFHTIHFPPIGBL-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical class C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 1
- BKMIWBZIQAAZBD-UHFFFAOYSA-N diindenoperylene Chemical compound C12=C3C4=CC=C2C2=CC=CC=C2C1=CC=C3C1=CC=C2C3=CC=CC=C3C3=CC=C4C1=C32 BKMIWBZIQAAZBD-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 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
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000005241 heteroarylamino group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 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
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- VQOXIYILDDQNTQ-UHFFFAOYSA-N manganese quinolin-8-ol Chemical compound [Mn].Oc1cccc2cccnc12 VQOXIYILDDQNTQ-UHFFFAOYSA-N 0.000 description 1
- 238000004776 molecular orbital Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000003136 n-heptyl 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])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 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
- 229910052757 nitrogen Inorganic materials 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
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].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.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 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- YEYHFKBVNARCNE-UHFFFAOYSA-N pyrido[2,3-b]pyrazine Chemical compound N1=CC=NC2=CC=CN=C21 YEYHFKBVNARCNE-UHFFFAOYSA-N 0.000 description 1
- BWESROVQGZSBRX-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine Chemical compound C1=NC=NC2=CC=CN=C21 BWESROVQGZSBRX-UHFFFAOYSA-N 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- GNHGQOQUCKGFCV-UHFFFAOYSA-N quinolin-8-ol;zinc Chemical compound [Zn].C1=CN=C2C(O)=CC=CC2=C1 GNHGQOQUCKGFCV-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon 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
- 238000006884 silylation reaction Methods 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000010025 steaming Methods 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
- UWRZIZXBOLBCON-UHFFFAOYSA-N styrylamine group Chemical group C(=CC1=CC=CC=C1)N UWRZIZXBOLBCON-UHFFFAOYSA-N 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N triphenylene Chemical compound C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- 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
-
- 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
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present invention provides new organo-metallic compound and utilizes its organic illuminating element.
Description
Technical field
With the mutual reference of related application
The application is advocated based on the korean patent application on the 9th of September in 2016 No. 10-2016-0116563 and 2017 8
The interests of the priority of month korean patent application the 10-2017-0106727th on the 23rd, the text comprising these korean patent applications
Full content as part of this specification disclosed in offering.
The present invention relates to new organo-metallic compound and the organic illuminating element for including it.
Background technology
In general, organic light emission phenomenon refers to the phenomenon for making electric energy be changed into luminous energy using organic substance.Using luminous
The organic illuminating element of phenomenon has wide viewing angle, excellent contrast, fast response time, brightness, driving voltage and response speed
Excellent is spent, so as to largely be studied.
Organic illuminating element generally has the organic matter layer comprising anode and negative electrode and between anode and negative electrode
Structure.In order to improve the efficiency of organic illuminating element and stability, often by utilizing the multilayer that each different material is formed
Structure forms above-mentioned organic matter layer, for example, can be by hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electronics
The formation such as implanted layer.For the structure of such organic illuminating element, if applying voltage between electrodes, hole
Organic matter layer is injected into from negative electrode from anode, electronics, exciton (exciton) is formed when institute's injected holes and electronics meet,
The exciton will send light when transitting to ground state again.
It is lasting to require exploitation new material for the organic matter used in organic illuminating element as described above.
Prior art literature
Patent document
Patent document 1：Korean Patent Publication No. the 10-2000-0051826th
The content of the invention
The present invention relates to new organo-metallic compound and the organic illuminating element for including it.
The present invention provides the organo-metallic compound represented by following chemical formula 1.
[chemical formula 1]
In above-mentioned chemical formula 1,
M is iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr) or hafnium (Hf),
R1To R3And R11To R13It is each independently hydrogen, deuterium, halogen, cyano group, nitro, amino, substituted or unsubstituted
C1-60Alkyl, C1-60Haloalkyl, substituted or unsubstituted C1-60Alkoxy, substituted or unsubstituted C1-60Halogenated alkoxy, take
Generation or unsubstituted C3-60Cycloalkyl, substituted or unsubstituted C2-60Alkenyl, substituted or unsubstituted C6-60Aryl, substitution or not
Substituted C6-60Aryloxy group or substituted or unsubstituted include more than the 1 heteroatomic C in N, O and S1-60Heterocycle
Base,
A1 is 0 to 7 integer,
A2 and a3 is each independently 0 to 4 integer,
B is 1 to 8 integer,
A1+b is less than 8,
N is 1,2 or 3.
In addition, the present invention a kind of organic illuminating element is provided comprising：It is first electrode, opposed with above-mentioned first electrode
And the second electrode that possesses and possess more than 1 layer of organic matter layer between above-mentioned first electrode and above-mentioned second electrode,
The organo-metallic compound represented by 1 layer of above-mentioned chemical formula 1 contained above in above-mentioned organic matter layer.
Organo-metallic compound represented by above-mentioned chemical formula 1 can be as the material of the organic matter layer of organic illuminating element
Use, efficiency can be improved in organic illuminating element, realize low driving voltage and/or improves life characteristic.Especially it is possible to
It is used as phosphorescent dopants comprising the organo-metallic compound represented by above-mentioned chemical formula 1 in luminescent layer.
Brief description of the drawings
Fig. 1 shows the example of the organic illuminating element formed by substrate 1, anode 2, luminescent layer 3, negative electrode 4.
Fig. 2 is shown by substrate 1, anode 2, hole injection layer 5, hole transmission layer 6, luminescent layer 7, the and of electron transfer layer 8
The example for the organic illuminating element that negative electrode 4 is formed.
Symbol description
1:Substrate 2:Anode
3:Luminescent layer 4:Negative electrode
5:Hole injection layer 6:Hole transmission layer
7:Luminescent layer 8:Electron transfer layer
Embodiment
Hereinafter, in order to help to understand the present invention, illustrate in more detail.
The present invention provides the compound represented by a kind of above-mentioned chemical formula 1.
In this specification,Refer to the bonding being connected with other substituents.
In this specification, " substituted or unsubstituted " this term refers to, by selected from deuterium, halogen group, itrile group, nitro,
Hydroxyl, carbonyl, ester group, imide, amino, oxidation phosphino-, alkoxy, aryloxy group, alkyl sulfenyl (
Alkyl thioxy), artyl sulfo (Aryl thioxy), alkyl sulfoxide base (
Alkyl sulfoxy), aryl sulfoxid es base (Aryl sulfoxy), silicyl, boryl, alkyl, ring
Alkyl, alkenyl, aryl, aralkyl, arylalkenyl, alkylaryl, alkyl amine group, aralkyl amido, heteroaryl amido, arylamine
More than 1 substituent substitution in base, aryl phosphino- or heteroatomic heterocyclic radical comprising more than 1 in N, O and S or
It is unsubstituted, or the substituent being formed by connecting by the substituent of more than 2 in foregoing illustrative substituent substitutes or unsubstituted.
Such as " substituent that the substituent of more than 2 is formed by connecting ", when being xenyl, xenyl can be interpreted to be taken by 1 phenyl
The substituent that the aryl in generation or 2 phenyl are formed by connecting.
In this specification, the carbon number of carbonyl is not particularly limited, but preferably carbon number is 1 to 40.Specifically,
It can be the compound of following structure, but be not limited to this.
In this specification, in ester group, the oxygen of ester group can by the straight chain of carbon number 1 to 25, side chain or cyclic alkyl or
The aryl substitution of carbon number 6 to 25.Specifically, it can be the compound of following structural formula, but be not limited to this.
In this specification, the carbon number of imide is not particularly limited, and preferably carbon number is 1 to 25.It is specific and
Speech, can be the compound of following structure, but not limited to this.
In this specification, silicyl specifically has trimethyl silyl, triethylsilyl, tertbutyldimethylsilyl chloride
Silylation, vinyldimethylsilyl, propyl-dimethyl silicyl, triphenyl-silyl, diphenylsilyl group,
Phenyl silyl groups etc., but it is not limited to this.
In this specification, boryl specifically has trimethyl boryl, triethyl group boryl, fert-butyidimethylsilyl boryl, triphen
Base boryl, phenyl boryl etc., but not limited to this.
In this specification, as the example of halogen group, there are fluorine, chlorine, bromine or iodine.
In this specification, abovementioned alkyl can be straight or branched, and carbon number is not particularly limited, but preferably 1 to
40.According to an embodiment, the carbon number of abovementioned alkyl is 1 to 20.According to another embodiment, the carbon of abovementioned alkyl
Atomicity is 1 to 10.According to another embodiment again, the carbon number of abovementioned alkyl is 1 to 6.As the concrete example of alkyl,
Have methyl, ethyl, propyl group, n-propyl, isopropyl, butyl, normal-butyl, isobutyl group, the tert-butyl group, sec-butyl, 1- methyl-butvls,
1- Ethyl-butyls, amyl group, n-pentyl, isopentyl, neopentyl, tertiary pentyl, hexyl, n-hexyl, 1- methyl amyls, 2- methylpents
Base, 4- methyl -2- amyl groups, 3,3- dimethylbutyls, 2- ethyl-butyls, heptyl, n-heptyl, 1- methylhexyls, cyclopentyl-methyl,
Cyclohexyl methyl, octyl group, n-octyl, t-octyl, 1- methylheptyls, 2- ethylhexyls, 2- propylpentyls, n-nonyl, 2,2- bis-
Methylheptyl, 1- Ethyl-propyls, 1,1- Dimethyl-propyls, isohesyl, 2- methyl amyls, 4- methylhexyls, 5- methylhexyls
Deng, but it is not limited to this.
In this specification, above-mentioned alkenyl can be straight or branched, and carbon number is not particularly limited, but preferably 2 to
40.According to an embodiment, the carbon number of above-mentioned alkenyl is 2 to 20.According to another embodiment, the carbon of above-mentioned alkenyl
Atomicity is 2 to 10.According to another embodiment again, the carbon number of above-mentioned alkenyl is 2 to 6.As concrete example, there is ethene
Base, 1- acrylic, isopropenyl, 1- cyclobutenyls, 2- cyclobutenyls, 3- cyclobutenyls, 1- pentenyls, 2- pentenyls, 3- pentenyls, 3-
Methyl isophthalic acid-cyclobutenyl, 1,3- butadienyls, pi-allyl, 1- phenylethylene -1- bases, 2- phenylethylene -1- bases, 2,2- diphenyl
Ethene -1- bases, 2- phenyl -2- (naphthalene -1- bases) ethene -1- bases, 2,2- double (hexichol -1- bases) ethene -1- bases, Stilbene base, styrene
Base etc., but it is not limited to this.
In this specification, cycloalkyl is not particularly limited, but the preferably cycloalkyl of carbon number 3 to 60, according to one
Embodiment, the carbon number of above-mentioned cycloalkyl is 3 to 30.According to another embodiment, the carbon number of above-mentioned cycloalkyl
For 3 to 20.According to another embodiment again, the carbon number of above-mentioned cycloalkyl is 3 to 6.Specifically, there are cyclopropyl, ring
Butyl, cyclopenta, 3- methylcyclopentyls, 2,3- dimethylcyclopentyls, cyclohexyl, 3- methylcyclohexyls, 4- methylcyclohexyls, 2,
3- Dimethylcyclohexyls, 3,4,5- trimethylcyclohexyls, 4- tert-butylcyclohexyls, suberyl, cyclooctyl etc., but be not limited to
This.
In this specification, aryl is not particularly limited, but the preferably aryl of carbon number 6 to 60, can be monocyclic virtue
Base or polyaromatic.According to an embodiment, the carbon number of above-mentioned aryl is 6 to 30.According to another embodiment, on
The carbon number for stating aryl is 6 to 20.Can be phenyl, xenyl, terphenyl as monocyclic aryl on above-mentioned aryl
Deng, but it is not limited to this.As above-mentioned polyaromatic, can be naphthyl, anthryl, phenanthryl, pyrenyl, base,Base, fluorenyl etc.,
But it is not limited to this.
In this specification, fluorenyl can be substituted, and 2 substituents can be bonded to each other and form spiro structure.In above-mentioned fluorenes
In the case that base is substituted, Ke Yiwei
Deng, but it is not limited to this.
In this specification, heterocyclic radical is to be used as heteroatomic heterocyclic radical, carbon atom comprising more than 1 in O, N, Si and S
Number is not particularly limited, but preferably carbon number is 2 to 60.As the example of heterocyclic radical, have thienyl, furyl, pyrrole radicals,
Imidazole radicals, thiazolyl,Oxazolyl,Di azoly, triazolyl, pyridine radicals, bipyridyl, pyrimidine radicals, triazine radical, triazolyl, a word used for translation
Piperidinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolyl, quinoxalinyl, phthalazinyl, Pyridopyrimidine base, pyrido-pyrazine base,
Pyrazine and pyrazinyl, isoquinolyl, indyl, carbazyl, benzoOxazolyl, benzimidazolyl, benzothiazolyl, benzo click
It is oxazolyl, benzothienyl, dibenzothiophenes base, benzofuranyl, phenanthroline (phenanthroline) base, thiazolyl, different
Oxazolyl,Di azoly, thiadiazolyl group, benzothiazolyl, phenothiazinyl and dibenzofuran group etc., but it is not limited to this.
In this specification, the illustration phase of aryl and above-mentioned aryl in aralkyl, arylalkenyl, alkylaryl, arylamine group
Together.In this specification, the alkyl in aralkyl, alkylaryl, alkyl amine group is identical with the illustration of abovementioned alkyl.This specification
In, the heteroaryl in heteroaryl amine can be applicable the explanation related to above-mentioned heterocyclic radical.In this specification, the alkenyl in arylalkenyl
It is identical with the illustration of above-mentioned alkenyl.In this specification, on arlydene, in addition to it is divalent group, can be applicable with it is above-mentioned
The related explanation of aryl.In this specification, on heteroarylidene, in addition to it is divalent group, it can be applicable and above-mentioned heterocycle
The related explanation of base.In this specification, on hydrocarbon ring, except its not for 1 valency group and 2 substituents with reference to being formed in addition to,
The explanation related to above-mentioned aryl or cycloalkyl can be applicable.In this specification, on heterocycle, except it is not 1 valency group and 2
Individual substituent with reference to and formed beyond, the explanation related to above-mentioned heterocyclic radical can be applicable.
On the other hand, in above-mentioned chemical formula 1, M can be iridium (Ir).
In above-mentioned chemical formula 1, R1To R3Can be hydrogen, deuterium, halogen, cyano group, nitro, amino, substitution or not independently of one another
Substituted C1-10Alkyl or substituted or unsubstituted C6-10Aryl.
For example, R1To R3Can be hydrogen, deuterium, halogen, cyano group, nitro, amino, methyl, ethyl, propyl group, just independently of one another
Propyl group, isopropyl, butyl, normal-butyl, isobutyl group, the tert-butyl group, sec-butyl, phenyl, xenyl, terphenyl or naphthyl.
Specifically, such as R1Can be hydrogen.
Specifically, such as R2And R3Can be hydrogen, methyl, ethyl or phenyl independently of one another.
In above-mentioned chemical formula 1, a1 to a3 can be 0,1,2 or 3 independently of one another.For example, a1 to a3 independently of one another may be used
Think 0 or 1.
In above-mentioned chemical formula 1, R11To R13Can be substituted or unsubstituted C independently of one another1-10Alkyl.
For example, R11To R13Independently of one another can be hydrogen, deuterium, halogen, cyano group, nitro, amino, methyl, ethyl, propyl group,
N-propyl, isopropyl, butyl, normal-butyl, isobutyl group, the tert-butyl group or sec-butyl.
Specifically, such as R11To R13It can be methyl.
In above-mentioned chemical formula 1, b can be 1,2 or 3.For example, b can be 1.
Now, a1 represents R1Number, when a1 be more than 2 when, the R of more than 21It can be same to each other or different to each other.With reference to above-mentioned
The structure of explanation and chemical formula 1 for a1, then it is appreciated that the explanation for a2 and a3.
In addition, b represents SiR11R12R13Number, when b be more than 2 when, the SiR of more than 211R12R13Can it is mutually the same or
It is different.
On the other hand, above-mentioned organo-metallic compound can be selected from following chemical formula 1-1 into the group represented by 1-8
It is any：
Above-mentioned chemical formula 1-1 into 1-8,
R1To R3And R11To R13, a1 to a3 and n it is identical with the definition in above-mentioned chemical formula 1.
For example, above-mentioned organo-metallic compound can be selected from following compounds.
Organo-metallic compound represented by above-mentioned chemical formula 1 includes the benzoquinoline with more than one silicyl and made
For part, it is improved using the life characteristic of the organic illuminating element of the organo-metallic compound and the long-life can be shown.
Now, the organo-metallic compound represented by above-mentioned chemical formula 1 for example can be such by following reaction equations 1 to 3
Ligand exchange reaction manufacture, but be not limited to this.Above-mentioned manufacture method can be more specific in Production Example described later.
[reaction equation 1]
[reaction equation 2]
[reaction equation 3]
Above-mentioned reaction can be implemented in polar solvent, specifically, can be real in the alcohol series solvents such as methanol, ethanol
Apply.
With reference to the structure of above-mentioned reaction equation 1 to 3 and chemical formula 1, initial substance is substituted as, is wanted so as to manufacture
Organo-metallic compound represented by the above-mentioned chemical formula 1 of manufacture.
In addition, the present invention provides the organic illuminating element for including the organo-metallic compound represented by above-mentioned chemical formula 1.Example
Such as, the present invention provides following organic illuminating element, and the organic illuminating element includes：First electrode and above-mentioned first electrode pair
The second electrode putting and possess and possesses more than 1 layer of organic matter between above-mentioned first electrode and above-mentioned second electrode
Layer, the organo-metallic compound represented by 1 layer of above-mentioned chemical formula 1 contained above in above-mentioned organic matter layer.
In addition, above-mentioned organic matter layer can include luminescent layer, above-mentioned luminescent layer can be included represented by above-mentioned chemical formula 1
Organo-metallic compound.In above-mentioned luminescent layer, the organo-metallic compound represented by above-mentioned chemical formula 1 can play dopant work
With.
Specifically, the phosphorescent dopants as above-mentioned luminescent layer, organic gold represented by above-mentioned chemical formula 1 can be included
Belong to compound.
Now, above-mentioned luminescent layer can be further comprising known main body.Specifically, in above-mentioned luminescent layer, above-mentioned master
The weight ratio of body and the organo-metallic compound represented by above-mentioned chemical formula 1 can be 99:1 to 80:20, but it is not limited to this.
The organic matter layer of organic illuminating element of the present invention can be formed by single layer structure, can also by be laminated with 2 layers with
The sandwich construction of upper organic matter layer is formed.For example, the organic illuminating element of the present invention can have following structure：Except luminescent layer
In addition also comprising the hole injection layer and hole transmission layer and above-mentioned luminescent layer between above-mentioned first electrode and above-mentioned luminescent layer
Electron transfer layer and electron injecting layer between above-mentioned second electrode is as organic matter layer.But the knot of organic illuminating element
Structure is not limited to this, can include the organic layer of smaller amounts or more quantity.
On the other hand, according to the organic illuminating element of the present invention can be sequentially laminated with substrate anode, more than 1 layer
Organic matter layer and negative electrode structure (standard type (normal type)) organic illuminating element.In addition, having according to the present invention
Machine light-emitting component can be that the reverse structure that negative electrode, more than 1 layer of organic matter layer and anode are sequentially laminated with substrate (is inverted
Type (inverted type)) organic illuminating element.For example, the organic illuminating element according to an embodiment of the invention
Structure be shown in Fig. 1 and 2.
Fig. 1 shows the example of the organic illuminating element formed by substrate 1, anode 2, luminescent layer 3, negative electrode 4.Such knot
The organo-metallic compound represented by above-mentioned chemical formula 1 can be included in structure, in above-mentioned luminescent layer.
Fig. 2 is shown by substrate 1, anode 2, hole injection layer 5, hole transmission layer 6, luminescent layer 7, the and of electron transfer layer 8
The example for the organic illuminating element that negative electrode 4 is formed.In such structure, above-mentioned hole injection layer, hole transmission layer, luminescent layer and
More than the 1 layer organo-metallic compound that can be included represented by above-mentioned chemical formula 1 in electron transfer layer.Preferably, luminescent layer
In can include above-mentioned chemical formula 1 represented by organo-metallic compound.
According to the organic illuminating element of the present invention except the above-mentioned institute of chemical formula 1 contained above of 1 layer in above-mentioned organic matter layer
Beyond the organo-metallic compound of expression, it can be manufactured using material known in the art and method.It is in addition, above-mentioned
In the case that organic illuminating element includes multiple organic matter layers, above-mentioned organic matter layer can be by same substance or different material shape
Into.
For example, can be by stacking gradually first electrode, organic matter on substrate according to the organic illuminating element of the present invention
Layer and second electrode and manufacture.At this point it is possible to manufacture as follows：Utilize sputtering method (sputtering) or electron-beam vapor deposition method (e-
Beam evaporation) etc PVD (physical vapor deposition method, physical Vapor Deposition), steamed on substrate
Plate metal or conductive metal oxide or their alloy and form anode, formed on the anode and noted comprising hole
Enter the organic matter layer of layer, hole transmission layer, luminescent layer and electron transfer layer, then evaporation can be used as negative electrode on the organic matter layer
Material.In addition to such method, can also on substrate successively evaporation cathode material, organic matter layer, anode material come
Manufacture organic illuminating element.
In addition, the compound represented by above-mentioned chemical formula 1, when manufacturing organic illuminating element, can not only be utilized
Vacuum vapour deposition, organic matter layer can also be formed as using solution coating method.Wherein, so-called solution coating method refers to, spin coating
Method, dip coating, knife coating, ink jet printing method, silk screen print method, spray-on process, rolling method etc., but it is not limited only to this.
In addition to method as described above, can also on substrate evaporation cathode material, organic matter layer, anode material successively
And manufacture organic illuminating element (WO 2003/012890).But manufacture method is not limited to this.
For example, above-mentioned first electrode is anode, above-mentioned second electrode is negative electrode；Or above-mentioned first electrode is negative electrode, on
It is anode to state second electrode.
As above-mentioned anode material, generally for enabling hole successfully to be injected to organic matter layer, preferably work function
Big material.As the concrete example of above-mentioned anode material, there are the metals such as vanadium, chromium, copper, zinc, gold or their alloy；Zinc oxide,
The metal oxides such as indium oxide, tin indium oxide (ITO), indium zinc oxide (IZO)；ZnO:Al or SnO2:The metals such as Sb and oxide
Combination；Poly- (3 methyl thiophene), poly- [3,4- (ethylidene -1,2- dioxies) thiophene] (PEDOT), polypyrrole and polyaniline etc. are led
Electrical macromolecule etc., but it is not limited only to this.
As above-mentioned cathode substance, generally for making electronics easily be injected to organic matter layer, preferably work function is small
Material.As the concrete example of above-mentioned cathode substance, there are the metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminium, silver, tin and lead
Or their alloy；LiF/Al or LiO2Sandwich construction material such as/Al etc., but it is not limited only to this.
Above-mentioned hole injection layer is the layer in the hole that injection carrys out self-electrode, is preferably followingization as hole injecting material
Compound：Possess the ability of transporting holes, there is the hole injection effect from anode, for the excellent of luminescent layer or luminescent material
Hole injection effect, prevent in luminescent layer caused exciton to be migrated to electron injecting layer or electron injection material, and thin
Film Forming ability is excellent.It is preferred that HOMO (highest occupied molecular orbital(HOMO), the highest occupied of hole injecting material
Molecular orbital) between the work function of anode material and the HOMO of surrounding organic matter layer.As hole infusion
The concrete example of matter, there are metalloporphyrin (porphyrin), Oligopoly thiophene, aryl amine system organic matter, the azepine benzophenanthrene system of six nitrile six to have
Machine thing, quinacridone (quinacridone) are that organic matter, (perylene) are organic matter, anthraquinone and polyaniline and polythiophene
It is electroconductive polymer etc., but is not limited only to this.
Above-mentioned hole transmission layer is to receive the hole from hole injection layer and by the layer of hole transport to luminescent layer, as
Hole transporting material, it is that can receive the hole from anode or hole injection layer and transfer them to the material of luminescent layer, it is right
The material that the mobility in hole is big is suitable.As concrete example, there are aryl amine system organic matter, electroconductive polymer, Yi Jitong
When block copolymer of conjugate moiety and non-conjugated portion etc. be present, but be not limited only to this.
It is that can receive hole and electronics respectively from hole transmission layer and electron transfer layer and make as above-mentioned luminescent substance
They with reference to and send the material of the light of visible region, preferably for the high material of the quantum efficiency of fluorescence or phosphorescence.Make
For concrete example, there is 8-hydroxyquinoline aluminum complex (Alq3)；Carbazole based compound；Two polystyrene-based (dimerized
Styryl) compound；BAlq；10- hydroxy benzo quinoline metal compounds；BenzoAzoles, benzothiazole and benzimidazole system
Compound；Poly- (to phenylene vinylidene) (PPV) is macromolecule；Loop coil (spiro) compound；Polyfluorene, rubrene etc., but not
It is only limitted to this.
As described above, above-mentioned luminescent layer can include material of main part and dopant material.Material of main part has aromatic fused ring
Derivative or nitrogen-containing heterocgcies etc..Specifically, as aromatic fused ring derivative, anthracene derivant, pyrene derivatives, naphthalene spread out
Biology, pentacene derivative, phenanthrene compound, fluoranthene compound etc., as nitrogen-containing heterocgcies, there are carbazole derivates, dibenzo
Furan derivatives, ladder type furan compoundPyrimidine derivatives etc., but it is not limited to this.
As dopant material, in addition to the organo-metallic compound represented by above-mentioned chemical formula 1, can further wrap
Containing aromatic amine derivative, styrylamine compounds, boron complexes, fluoranthene compound, metal complex etc..Specifically,
As aromatic amine derivative, it is the aromatic fused ring derivative with substituted or unsubstituted arylamino, has with aryl
The pyrene of amino, anthracene,Two indeno pyrenes (Periflanthene) etc., it is to substitute or do not taking as styrylamine compounds
Substitution has the compound of at least one aryl vinyl on the arylamine in generation, by selected from aryl, silicyl, alkyl, cycloalkyl and
1 in arylamino or more than 2 substituent substitutions or unsubstituted.Specifically, there are styryl amine, styryl two
Amine, styryl triamine, styryl tetramine etc., but it is not limited to this.In addition, as metal complex, there are complex of iridium, platinum
Complex etc., but it is not limited to this.
Above-mentioned electron transfer layer is to receive electronics and by the layer of electric transmission to luminescent layer from electron injecting layer, as electronics
Transport materials, it is that can receive electronics well from negative electrode and transfer them to the material of luminescent layer, it is big to the mobility of electronics
Material be suitable.As concrete example, there are the Al complexs of 8-hydroxyquinoline, comprising Alq3Complex, organic free radical
Compound, flavonol-metal complex etc., but it is not limited only to this.Electron transfer layer can be as used in conventional art
As be used together with the cathode substance of any desired.Particularly, the example of suitable cathode substance is with low work function
And along with aluminium lamination or the common material of silver layer.Specially caesium, barium, calcium, ytterbium and samarium, in the case of each material, along with aluminium
Layer or silver layer.
Above-mentioned electron injecting layer be injection come self-electrode electronics layer, preferably following compound：With transmission electronics
Ability, have the electron injection effect from negative electrode, the excellent electron injection effect for luminescent layer or luminescent material, prevent
Only caused exciton migrates to hole injection layer in luminescent layer, and film Forming ability is excellent.Specifically, have Fluorenone,
Anthraquinone bismethane (Anthraquinodimethane), diphenoquinone, thiopyrandioxide,Azoles,Diazole, triazole, imidazoles,
Tetrabasic carboxylic acid, fluorenylidene-methane, anthrone etc. and their derivative, metal complex and nitrogenous 5 membered ring derivatives etc., but simultaneously
Not limited to this.
As above-mentioned metal complex, have 8-hydroxyquinoline lithium, double (8-hydroxyquinoline) zinc, double (8-hydroxyquinoline) copper,
It is double (8-hydroxyquinoline) manganese, three (8-hydroxyquinoline) aluminium, three (2- methyl -8-hydroxyquinoline) aluminium, three (8-hydroxyquinoline) galliums, double
(10- hydroxy benzos [h] quinoline) beryllium, double (10- hydroxy benzos [h] quinoline) zinc, double (2- methyl -8- quinoline) gallium chlorides, double (2-
Methyl -8- quinoline) (orthoresol) gallium, double (2- methyl -8- quinoline) (1- naphthols) aluminium, double (2- methyl -8- quinoline) (beta naphthals)
Gallium etc., but it is not limited to this.
According to the present invention organic illuminating element according to used in material, can be top emission type, bottom emission type
Or bidirectional luminescence type.
In addition, can also be in organic solar batteries or organic transistor comprising above-mentioned in addition to organic illuminating element
Organo-metallic compound represented by chemical formula 1.
Organo-metallic compound represented by above-mentioned chemical formula 1 is illustrated in the examples below and comprising the organic of its
The manufacture of light-emitting component.But following embodiments are used to illustrate the present invention, the scope of the present invention not limited to this.
[Production Example]
Production Example 1-1:The compound synthesis of intermediate A 1 and B1
(1) intermediate 1-1a manufacture
By 3- bromine Benzoquinoline quinoline (54.0g, 0.21mol), 4,4,5, the 5- tetramethyls-boron of [1,3,2]-dioxane penta
Alkane (58.5g, 0.23mol), Pd (dppf) Cl2(1.53g, 2.09mmol), KOAc (61.6g, 0.62mol) are put into twoAlkane
(Dioxane) in 830mL, stir 8 hours under reflux conditions.Temperature is reduced to normal temperature, and solvent under reduced pressure is concentrated.Should
Concentrate is dissolved completely in CHCl3Afterwards, it is washed with water, the solution decompression dissolved with product is concentrated, refined using column chromatography.
So as to obtain intermediate 1-1a (52.8g, yield 82%, MS:[M+H]+=306).
(2) manufacture of intermediate A 1
Under nitrogen atmosphere, by intermediate 1-1a (52.8g, 173mmol) and trim,ethylchlorosilane
(chlorotrimethylsilane) after (20.6g, 190mmol) is dissolved in tetrahydrofuran 600mL, addition 2M potassium carbonate is water-soluble
Liquid (250ml), tetrakis triphenylphosphine palladium (3.8g, 3.46mmol) is put into, then carries out the stirring of 14 hours under reflux conditions.
React after terminating, reduction temperature, after separate aqueous layer, remove the solvent of organic layer.Use CHCl3After dissolving, it is washed with water, puts
Enter magnesium sulfate and Emathlite, filter and be concentrated under reduced pressure after stirring.Afterwards, under the conditions of hexane, by pillar layer separation,
Manufacture compound A1 (35.0g, yield 80%, MS:[M+H]+=252).
(3) intermediate 1-1b manufacture
In round-bottomed flask, iridium chloride (12g, 40.2mmol) and compound A1 (25.3g, 0.10mmol) are put into 2- second
In ethoxy-ethanol 1000ml and distilled water 330ml, and heating stirring 18 hours.Temperature is reduced to normal temperature, filtered, with ethanol 3L
Washing, so as to manufacture solid chemical compound 1-1b (30.7g, yield 52%).
(4) manufacture of intermediate B 1
By addition have intermediate 1-1b (30.7g, 0.021mol) and dichloromethane 800ml AgOTf (14.6g,
0.057mol) it is put into and is dissolved in methanol 400ml, then carries out stirring at normal temperature in the state of light is shielded.After 24 hours, filtering
The solvent in filtrate is removed afterwards, carries out toluene precipitation, not addition manufactures compound B-11 (yield 91%) refinedly.
Production Example 1-2:The compound synthesis of intermediate A 2 and B2
(1) intermediate 1-1c manufacture
Instead of 3- bromine Benzoquinoline quinoline using 6- bromine Benzoquinoline quinoline (50.0g), in addition, using with manufacture
Mesosome 1-1a method identical method, manufacture above-claimed cpd 1-1c (47.3g, yield 80%, MS:[M+H]+=306).
(2) manufacture of intermediate A 2
Intermediate 1-1c is used instead of intermediate 1-1a, it is in addition, identical using the method with manufacturing intermediate A 1
Method, manufacture above-mentioned intermediate A 2 (30.1g, yield 77%, MS:[M+H]+=252).
(3) intermediate 1-1d manufacture
Intermediate A 2 is used instead of intermediate A 1, in addition, utilizes the method identical with manufacturing intermediate 1-1b
Method, manufacture above-mentioned intermediate 1-1d (28.8g, yield 49%).
(4) manufacture of intermediate B 2
Intermediate 1-1d is used instead of intermediate 1-1b, it is in addition, identical using the method with manufacturing intermediate B 1
Method, manufacture above-mentioned intermediate B 2 (yield 90%).
Production Example 1-3:The compound synthesis of intermediate A 3 and B3
(1) intermediate 1-1e manufacture
Instead of 3- bromine Benzoquinoline quinoline using 7- bromine Benzoquinoline quinoline (50.0g), in addition, using with manufacture
Mesosome 1-1a method identical method, manufacture above-claimed cpd 1-1c (46.5g, yield 79%, MS:[M+H]+=306).
(2) manufacture of intermediate A 3
Intermediate 1-1e is used instead of intermediate 1-1a, it is in addition, identical using the method with manufacturing intermediate A 1
Method, manufacture above-mentioned intermediate A 3 (29.5g, yield 77%, MS:[M+H]+=252).
(3) intermediate 1-1f manufacture
Intermediate A 3 is used instead of intermediate A 1, utilizes the method identical method with manufacturing intermediate 1-1b, manufacture
Above-mentioned intermediate 1-1f (26.1g, yield 48%).
(4) manufacture of intermediate B 3
Intermediate 1-1f is used instead of intermediate 1-1b, it is in addition, identical using the method with manufacturing intermediate B 1
Method, manufacture above-mentioned intermediate B 3 (yield 92%).
Production Example 1-4:The compound synthesis of intermediate A 4 and B4
(1) intermediate 1-1g manufacture
Instead of 3- bromine Benzoquinoline quinoline using 8- bromine Benzoquinoline quinoline (50.0g), in addition, using with manufacture
Mesosome 1-1a method identical method, manufacture above-claimed cpd 1-1g (47.1g, yield 80%, MS:[M+H]+=306).
(2) manufacture of intermediate A 4
Intermediate 1-1g is used instead of intermediate 1-1a, it is in addition, identical using the method with manufacturing intermediate A 1
Method, manufacture above-mentioned intermediate A 4 (30.3g, yield 78%, MS:[M+H]+=252).
(3) intermediate 1-1h manufacture
Intermediate A 3 is used instead of intermediate A 1, in addition, utilizes the method identical with manufacturing intermediate 1-1b
Method, manufacture above-mentioned intermediate 1-1h (30.2g, yield 46%).
(4) manufacture of intermediate B 4
Intermediate 1-1h is used instead of intermediate 1-1b, it is in addition, identical using the method with manufacturing intermediate B 1
Method, manufacture above-mentioned intermediate B 4 (yield 91%).
Production Example 2
Production Example 2-1:Intermediate D1 compound synthesis
(1) intermediate 2-1b manufacture
Instead of intermediate A 1 using 2- phenylpyridines (compound C1), in addition, using with manufacturing intermediate 1-1b
Method identical method, manufacture above-mentioned intermediate 2-1b (20.1g, yield 50%).
(2) intermediate D1 manufacture
Intermediate 2-1b is used instead of intermediate 1-1b, it is in addition, identical using the method with manufacturing intermediate B 1
Method, manufacture above-mentioned intermediate D1 (14.2g).
Production Example 2-2:Intermediate C2 and D2 compound synthesis
(1) intermediate 3-1a manufacture
Under nitrogen atmosphere, by 2,4- dibromo pyridines (35.0g, 0.15mol) and phenylboric acid (phenylboronic
Acid after) (20.20g, 0.16mol) is dissolved in tetrahydrofuran 300mL, 1.5M wet chemicals (150mL) is added, are put into four
(triphenylphosphine) palladium (3.44g, 2.98mmol), then heating stirring 11 hours.Temperature is reduced to normal temperature, by water layer separation simultaneously
Remove, be concentrated under reduced pressure after being dried with anhydrous magnesium sulfate, recrystallized, dried using column chromatography, so as to manufacture above-mentioned intermediate
3-1a (29.1g, yield 84%, MS:[M+H]+=233).
(2) intermediate C2 manufacture
Intermediate C2 is used instead of 2,4- dibromo pyridines, in addition, utilizes the method phase with manufacturing intermediate 3-1a
Same method, manufacture above-claimed cpd C2 (23.8g, yield 83%, MS:[M+H]+=232).
(3) intermediate 3-1b manufacture
Instead of intermediate A 1 using intermediate C2 (15.8g), in addition, the method with manufacturing intermediate 1-1b is utilized
Identical method, manufacture above-mentioned intermediate 3-1b (19.1g, yield 55%).
(4) intermediate D2 manufacture
Intermediate 3-1b is used instead of intermediate 1-1b, it is in addition, identical using the method with manufacturing intermediate B 1
Method, manufacture above-mentioned intermediate D2 (11.1g).
Production Example 2-3:Intermediate C3 and D3 compound synthesis
(1) intermediate C3 manufacture
The bromo- 4- picolines of 2- are used instead of 2,4- dibromo pyridines, in addition, using with manufacture intermediate 3-1a's
Method identical method, manufacture above-claimed cpd C3 (51.0g, yield 86%, MS:[M+H]+=170).
(2) intermediate 4-1b manufacture
Instead of intermediate A 1 using intermediate C3 (26.4g), in addition, the method with manufacturing intermediate 1-1b is utilized
Identical method, manufacture above-mentioned intermediate 4-1b (32.1g, yield 50%).
(3) intermediate D3 manufacture
Intermediate 4-1b is used instead of intermediate 1-1b, it is in addition, identical using the method with manufacturing intermediate B 1
Method, manufacture above-mentioned intermediate D3 (20.0g).
Production Example 2-4:Intermediate C4 and D4 compound synthesis
(1) intermediate 4-1a manufacture
2,5- dibromo pyridines are used instead of 2,4- dibromo pyridines, in addition, utilize the side with manufacturing intermediate 3-1a
Method identical method, manufacture above-mentioned intermediate 4-1a (30.1g, yield 87%, MS:[M+H]+=234).
(2) intermediate C4 manufacture
Intermediate 4-1a is used instead of 2,4- dibromo pyridines, in addition, utilizes the method with manufacturing intermediate 3-1a
Identical method, manufacture above-claimed cpd C4 (24.9g, yield 83%, MS:[M+H]+=232).
(2) intermediate 5-1b manufacture
Instead of intermediate A 1 using intermediate C4 (15.0g), in addition, the method with manufacturing intermediate 1-1b is utilized
Identical method, manufacture above-mentioned intermediate 5-1b (17.8g, yield 49%).
(4) intermediate D4 manufacture
Intermediate 5-1b is used instead of intermediate 1-1b, it is in addition, identical using the method with manufacturing intermediate B 1
Method, manufacture above-mentioned intermediate D4 (10.3g).
Production Example 2-5:Intermediate C5 and D5 compound synthesis
(1) intermediate 5-1a manufacture
The bromo- 4- picolines of 2,5- bis- are used instead of 2,4- dibromo pyridines, in addition, using with manufacturing intermediate 3-
1a method identical method, manufacture above-mentioned intermediate 5-1a (30.4g, yield 88%, MS:[M+H]+=248).
(2) intermediate C5 manufacture
Intermediate 5-1a is used instead of 2,4- dibromo pyridines, in addition, utilizes the method with manufacturing intermediate 3-1a
Identical method, manufacture above-claimed cpd C5 (24.2g, yield 81%, MS:[M+H]+=246).
(3) intermediate 6-1b manufacture
Instead of intermediate A 1 using intermediate C5 (15.0g), in addition, the method with manufacturing intermediate 1-1b is utilized
Identical method, manufacture above-mentioned intermediate 6-1b (16.5g, yield 48%).
(4) intermediate D5 manufacture
Intermediate 6-1b is used instead of intermediate 1-1b, it is in addition, identical using the method with manufacturing intermediate B 1
Method, manufacture above-mentioned intermediate D5 (9.8g).
Production Example 2-6:Intermediate C6 and D6 compound synthesis
(1) intermediate C6 manufacture
Instead of 2,4- dibromo pyridines and phenylboric acid using 2- bromopyridines and [1,1'- biphenyl] -4- ylboronic acids, except this it
Outside, the method identical method with manufacturing intermediate 3-1a, manufacture above-claimed cpd C6 (36.2g, yield 82%, MS are utilized:[M
+H]+=232).
(2) intermediate 7-1b manufacture
Instead of intermediate A 1 using intermediate C6 (15.5g), the method identical side with manufacturing intermediate 1-1b is utilized
Method, manufacture above-mentioned intermediate 7-1b (19.0g, yield 51%).
(3) intermediate D6 manufacture
Intermediate 7-1b is used instead of intermediate 1-1b, it is in addition, identical using the method with manufacturing intermediate B 1
Method, manufacture above-mentioned intermediate D6 (11.2g).
Production Example 2-7:Intermediate C7 and D7 compound synthesis
(1) intermediate C7 manufacture
Instead of 2,4- dibromo pyridines and phenylboric acid using 2- bromopyridines and [1,1'- biphenyl] -3- ylboronic acids, except this it
Outside, the method identical method with manufacturing intermediate 3-1a, manufacture above-claimed cpd C7 (37.5g, yield 85%, MS are utilized:[M
+H]+=232).
(2) intermediate 8-1b manufacture
Instead of intermediate A 1 using intermediate C7 (14.6g), in addition, the method with manufacturing intermediate 1-1b is utilized
Identical method, manufacture above-mentioned intermediate 8-1b (18.4g, yield 53%).
(3) intermediate D7 manufacture
Intermediate 8-1b is used instead of intermediate 1-1b, it is in addition, identical using the method with manufacturing intermediate B 1
Method, manufacture above-mentioned intermediate D7 (10.2g).
Production Example 3-1:The compound synthesis of compound 1
Under nitrogen atmosphere, compound B-11 (8.5g, 9.40mmol) and compound C1 (3.6g, 23.5mmol), 55ml are put into
MeOH, 55ml EtOH, stirred 48 hours at 90 DEG C of reaction temperature.After reaction terminates, filtering, in ethyl acetate：Hexane
=1:Pass through pillar layer separation, manufacture compound 1 (yield 41%) under the conditions of 6.
Production Example 3-2:The compound synthesis of compound 2
Intermediate C5 is used instead of intermediate C1, in addition, utilizes the method identical side with manufacturing compound 1
Method, manufacture above-claimed cpd 2 (yield 39%).
Production Example 3-3:The compound synthesis of compound 3
Intermediate C7 is used instead of intermediate C1, in addition, utilizes the method identical side with manufacturing compound 1
Method, manufacture above-claimed cpd 3 (yield 42%).
Production Example 3-4:The compound synthesis of compound 4
Instead of intermediate B 1 and intermediate C1 use intermediate B 2 and intermediate C2, in addition, using with manufactureization
The method identical method of compound 1, manufacture above-claimed cpd 4 (yield 37%).
Production Example 3-5:The compound synthesis of compound 5
Instead of intermediate B 1 and intermediate C1 use intermediate B 3 and intermediate C4, in addition, using with manufactureization
The method identical method of compound 1, manufacture above-claimed cpd 5 (yield 39%).
Production Example 3-6:The compound synthesis of compound 6
Instead of intermediate B 1 and intermediate C1 use intermediate B 4 and intermediate C3, in addition, using with manufactureization
The method identical method of compound 1, manufacture above-claimed cpd 6 (yield 38%).
Production Example 3-7:The compound synthesis of compound 7
Instead of intermediate B 1 and intermediate C1 use intermediate D1 and intermediate A 1, in addition, using with manufactureization
The method identical method of compound 1, manufacture above-claimed cpd 7 (yield 37%).
Production Example 3-8:The compound synthesis of compound 8
Instead of intermediate B 1 and intermediate C1 use intermediate D2 and intermediate A 1, in addition, using with manufactureization
The method identical method of compound 1, manufacture above-claimed cpd 8 (yield 40%).
Production Example 3-9:The compound synthesis of compound 9
Instead of intermediate B 1 and intermediate C1 use intermediate D3 and intermediate A 1, in addition, using with manufactureization
The method identical method of compound 1, manufacture above-claimed cpd 9 (yield 38%).
Production Example 3-10:The compound synthesis of compound 10
Instead of intermediate B 1 and intermediate C1 use intermediate D4 and intermediate A 1, in addition, using with manufactureization
The method identical method of compound 1, manufacture above-claimed cpd 10 (yield 42%).
Production Example 3-11:The compound synthesis of compound 11
Instead of intermediate B 1 and intermediate C1 use intermediate D2 and intermediate A 2, in addition, using with manufactureization
The method identical method of compound 1, manufacture above-claimed cpd 11 (yield 40%).
Production Example 3-12:The compound synthesis of compound 12
Instead of intermediate B 1 and intermediate C1 use intermediate D5 and intermediate A 2, in addition, using with manufactureization
The method identical method of compound 1, manufacture above-claimed cpd 12 (yield 42%).
Production Example 3-13:The compound synthesis of compound 13
Instead of intermediate B 1 and intermediate C1 use intermediate D6 and intermediate A 2, in addition, using with manufactureization
The method identical method of compound 1, manufacture above-claimed cpd 13 (yield 40%).
Production Example 3-14:The compound synthesis of compound 14
Instead of intermediate B 1 and intermediate C1 use intermediate D3 and intermediate A 3, in addition, using with manufactureization
The method identical method of compound 1, manufacture above-claimed cpd 14 (yield 37%).
Production Example 3-15:The compound synthesis of compound 15
Instead of intermediate B 1 and intermediate C1 use intermediate D5 and intermediate A 3, in addition, using with manufactureization
The method identical method of compound 1, manufacture above-claimed cpd 15 (yield 39%).
Production Example 3-16:The compound synthesis of compound 16
Instead of intermediate B 1 and intermediate C1 use intermediate D7 and intermediate A 3, in addition, using with manufactureization
The method identical method of compound 1, manufacture above-claimed cpd 16 (yield 38%).
Production Example 3-17:The compound synthesis of compound 17
Instead of intermediate B 1 and intermediate C1 use intermediate D1 and intermediate A 4, in addition, using with manufactureization
The method identical method of compound 1, manufacture above-claimed cpd 17 (yield 35%).
Production Example 3-18:The compound synthesis of compound 18
Instead of intermediate B 1 and intermediate C1 use intermediate D4 and intermediate A 4, in addition, using with manufactureization
The method identical method of compound 1, manufacture above-claimed cpd 18 (yield 39%).
Production Example 3-19:The compound synthesis of compound 19
Intermediate A 1 is used instead of intermediate C1, in addition, utilizes the method identical side with manufacturing compound 1
Method, manufacture above-claimed cpd 19 (yield 43%).
Production Example 3-20:The compound synthesis of compound 20
Instead of intermediate B 1 and intermediate C1 use intermediate B 3 and intermediate A 3, in addition, using with manufactureization
The method identical method of compound 1, manufacture above-claimed cpd 20 (yield 44%).
Embodiment 1
Will be withThe glass substrate that thickness thin film is coated with ITO (tin indium oxide) is put into the steaming dissolved with detergent
In distilled water, washed using ultrasonic wave.Now, detergent uses the product of Fei Xier companies (Fischer Co.), distilled water
Distilled water after being filtered 2 times using the filter (Filter) manufactured by Millipore Corp. (Millipore Co.).ITO is washed
After washing 30 minutes, with distilled water 2 ultrasonic washings for carrying out 10 minutes repeatedly.After distillation water washing terminates, isopropyl is used successively
After alcohol, acetone, methanol solvate carry out ultrasonic washing and dried, plasma washing machine is delivered to.In addition, utilize oxygen plasma
Body, after aforesaid substrate is cleaned 5 minutes, deliver the substrate to vacuum evaporation plating machine.
On the ito transparent electrode prepared as described above withThickness thermal vacuum the following azepine of six nitrile six is deposited
Benzophenanthrene (hexanitrile hexaazatriphenylene；HAT hole injection layer) is formed.Over the hole-injecting layer
WithThickness thermal vacuum evaporation join as the 4-4'- double [N- (1- naphthyls)-N- phenyl aminos] of the material of transporting holes
Benzene (NPB；HT-1) form hole transmission layer, in HT-1 evaporation films withThickness vacuum evaporation HT-2 compounds and
Form electronic barrier layer.Then, with 44 in above-mentioned HT-2 evaporation films:44:12 weight is than chemical combination of the common evaporation as main body
The compound 1 as phosphorescent dopants manufactured in thing H1 and H2 and Production Example 3-1, so as to be formedThe hair of thickness
Photosphere.On above-mentioned luminescent layer withThickness vacuum evaporation ET-1 materials, further by ET-2 materials and 2% weight ratio
Li withThickness is deposited and forms electron transfer layer and electron injecting layer altogether.On above-mentioned electron injecting layer withThickness AM aluminum metallization and form negative electrode.
In said process, the evaporation rate of organic matter maintainsAluminium maintainsEvaporation speed
Degree, during evaporation, vacuum maintains 1 × 10-7~5 × 10-8Torr, make organic illuminating element.
Embodiment 2 to 9
When forming luminescent layer, as phosphorescent dopants, each compound described in table 1 below is used instead of compound 1,
In addition, the organic illuminating element with the identical method of above-described embodiment 1, respectively manufacture embodiment 2 to 9 is implemented.
Comparative example 1 to 3
When forming luminescent layer, as dopant, instead of compound 1 using each compound described in table 1 below, except this
Outside, implement the organic illuminating element with the identical method of above-described embodiment 1, respectively manufacture comparative example 1 to 3.
Experimental example 1
Apply electric current, measure voltage, effect to the organic illuminating element made in above-described embodiment 1 to 9 and comparative example 1 to 3
Rate, chromaticity coordinates and life-span, and the results are shown in table 1 below.
T95 refers to that brightness was reduced to the time needed for the 95% of original intensity.
[table 1]
Can be confirmed by above-mentioned table 1, use the present invention compound as phosphorescent dopants in the case of, with use E1 and
The comparative example of E2 compound is compared, and excellent characteristic is shown in terms of the life-span.Thus can confirm, TMS substituents produce to the life-span
It is raw to influence.In addition, in the case of embodiment 2 to 4,6 and 8, more than about 2 times of life characteristic increase compared with comparative example 2.By this
The result of sample can confirm, notable according to the difference of the presence or absence of silyl substitution radicals He the position of substitution, aging variation.
Claims (9)
1. a kind of organo-metallic compound, it is represented by following chemical formula 1：
Chemical formula 1
In the chemical formula 1,
M is iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr) or hafnium (Hf),
R1To R3And R11To R13It is each independently hydrogen, deuterium, halogen, cyano group, nitro, amino, substituted or unsubstituted C1-60Alkane
Base, C1-60Haloalkyl, substituted or unsubstituted C1-60Alkoxy, substituted or unsubstituted C1-60Halogenated alkoxy, substitution or not
Substituted C3-60Cycloalkyl, substituted or unsubstituted C2-60Alkenyl, substituted or unsubstituted C6-60It is aryl, substituted or unsubstituted
C6-60Aryloxy group or substituted or unsubstituted include more than the 1 heteroatomic C in N, O and S1-60Heterocyclic radical,
A1 is 0 to 7 integer,
A2 and a3 is each independently 0 to 4 integer,
B is 1 to 8 integer,
A1+b is less than 8,
N is 1,2 or 3.
2. organo-metallic compound according to claim 1, wherein, M is iridium (Ir).
3. organo-metallic compound according to claim 1, wherein, R1For hydrogen.
4. organo-metallic compound according to claim 1, wherein, R2And R3Be each independently hydrogen, methyl, ethyl or
Phenyl.
5. organo-metallic compound according to claim 1, wherein, R11To R13For methyl.
6. organo-metallic compound according to claim 1, wherein, the compound be selected from following chemical formula 1-1 extremely
Any of group represented by 1-8：
The chemical formula 1-1 into 1-8,
R1To R3And R11To R13, a1 to a3 and n it is identical with the definition in claim 1.
7. organo-metallic compound according to claim 1, wherein, the compound is appointing in following compounds
It is a kind of：
8. a kind of organic illuminating element comprising：First electrode, it is opposed with the first electrode and possess second electrode,
And possess more than 1 layer of organic matter layer between the first electrode and the second electrode, 1 in the organic matter layer
Organo-metallic compound any one of layer claim 1 to 7 contained above.
9. organic illuminating element according to claim 8, wherein, the organic matter layer includes luminescent layer,
Include the phosphorescent dopants organo-metallic compound as the luminescent layer.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2016-0116563 | 2016-09-09 | ||
| KR20160116563 | 2016-09-09 | ||
| KR1020170106727A KR101966280B1 (en) | 2016-09-09 | 2017-08-23 | Novel organometallic compound and organic light emitting device comprising the same |
| KR10-2017-0106727 | 2017-08-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN107805264A true CN107805264A (en) | 2018-03-16 |
| CN107805264B CN107805264B (en) | 2020-07-07 |
Family
ID=61576559
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710804805.5A Active CN107805264B (en) | 2016-09-09 | 2017-09-08 | Novel organometallic compound and organic light-emitting element using same |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN107805264B (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030162299A1 (en) * | 2002-02-08 | 2003-08-28 | Canon Kabushiki Kaisha | Light emissive iridium (III) complexes |
| CN103827119A (en) * | 2011-07-21 | 2014-05-28 | 罗门哈斯电子材料韩国有限公司 | Novel organic electroluminescence compounds and organic electroluminescence device using the same |
-
2017
- 2017-09-08 CN CN201710804805.5A patent/CN107805264B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030162299A1 (en) * | 2002-02-08 | 2003-08-28 | Canon Kabushiki Kaisha | Light emissive iridium (III) complexes |
| CN103827119A (en) * | 2011-07-21 | 2014-05-28 | 罗门哈斯电子材料韩国有限公司 | Novel organic electroluminescence compounds and organic electroluminescence device using the same |
Non-Patent Citations (1)
| Title |
|---|
| JAEMIN LEE等: "Improved performance of solution-processable OLEDs by silyl substitution to phosphorescent iridium complexe", 《SYNTHETIC METALS》 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN107805264B (en) | 2020-07-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN110492011B (en) | Organic light emitting device | |
| CN107840835B (en) | Novel heterocyclic compound and organic light-emitting element using same | |
| CN109564974A (en) | Organic luminescent device | |
| CN109564973B (en) | Organic light emitting device | |
| CN107759638A (en) | New organo-metallic compound and utilize its organic illuminating element | |
| CN109071513A (en) | New heterocyclic compound and the organic luminescent device comprising it | |
| CN107406391A (en) | Spiro-compound and the organic illuminating element for including it | |
| CN110709403A (en) | Novel heterocyclic compound and organic light emitting device using the same | |
| CN108250189A (en) | Novel heterocyclic compounds and utilize its organic illuminating element | |
| CN105431423A (en) | Heterocyclic compound and organic light-emitting device comprising same | |
| CN109476597A (en) | New compound and the organic illuminating element for utilizing it | |
| CN107635978A (en) | Heterocyclic compound and the organic luminescent device for including it | |
| CN110267942A (en) | New heterocyclic compound and the organic luminescent device using it | |
| CN107778260A (en) | Novel organic luminescent material and the organic illuminating element for including it | |
| CN107619410A (en) | Compound and the organic electronic element for including it | |
| CN108884086A (en) | Novel heterocyclic compounds and the organic illuminating element for utilizing it | |
| CN107311987A (en) | Compound and the organic electronic element comprising it | |
| KR20200065952A (en) | Organic light emitting device | |
| CN112654615A (en) | Novel heterocyclic compound and organic light-emitting device comprising same | |
| CN110536887A (en) | New compound and organic luminescent device comprising it | |
| CN112424191A (en) | Novel compound and organic light emitting device comprising the same | |
| CN109836419A (en) | Novel heterocyclic compounds and the organic illuminating element for utilizing it | |
| CN110573498A (en) | Novel heterocyclic compound and organic light-emitting device comprising same | |
| CN109415374A (en) | Heterocyclic compound and organic illuminating element comprising it | |
| CN107406350A (en) | New compound and the organic illuminating element for including it |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |