JP2014088399A - 置換されたトリフェニレン環構造を有する化合物および有機エレクトロルミネッセンス素子 - Google Patents
置換されたトリフェニレン環構造を有する化合物および有機エレクトロルミネッセンス素子 Download PDFInfo
- Publication number
- JP2014088399A JP2014088399A JP2013256692A JP2013256692A JP2014088399A JP 2014088399 A JP2014088399 A JP 2014088399A JP 2013256692 A JP2013256692 A JP 2013256692A JP 2013256692 A JP2013256692 A JP 2013256692A JP 2014088399 A JP2014088399 A JP 2014088399A
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- group
- compound
- atom
- different
- 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
- 150000001875 compounds Chemical class 0.000 title claims abstract description 92
- 125000005580 triphenylene group Chemical group 0.000 title claims abstract description 53
- 239000000463 material Substances 0.000 claims abstract description 64
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims abstract description 54
- 239000012044 organic layer Substances 0.000 claims abstract description 33
- 238000002347 injection Methods 0.000 claims abstract description 24
- 239000007924 injection Substances 0.000 claims abstract description 24
- 239000000470 constituent Substances 0.000 claims abstract description 8
- 239000010410 layer Substances 0.000 claims description 121
- 125000001424 substituent group Chemical group 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 17
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 229910052805 deuterium Inorganic materials 0.000 claims description 16
- 125000004431 deuterium atom Chemical group 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 125000001153 fluoro group Chemical group F* 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 238000005401 electroluminescence Methods 0.000 claims description 4
- 239000000243 solution Substances 0.000 abstract description 11
- 150000002894 organic compounds Chemical class 0.000 abstract description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 42
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- 239000012043 crude product Substances 0.000 description 36
- -1 anode Substances 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 31
- 239000000843 powder Substances 0.000 description 31
- 230000000052 comparative effect Effects 0.000 description 28
- 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 28
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 238000000034 method Methods 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 238000005259 measurement Methods 0.000 description 22
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 230000000903 blocking effect Effects 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- 239000000741 silica gel Substances 0.000 description 18
- 229910002027 silica gel Inorganic materials 0.000 description 18
- 238000001816 cooling Methods 0.000 description 17
- 239000002244 precipitate Substances 0.000 description 17
- 238000003756 stirring Methods 0.000 description 17
- 238000001914 filtration Methods 0.000 description 16
- 239000010409 thin film Substances 0.000 description 16
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 15
- 238000005160 1H NMR spectroscopy Methods 0.000 description 15
- 238000004440 column chromatography Methods 0.000 description 15
- 230000005525 hole transport Effects 0.000 description 15
- 239000003480 eluent Substances 0.000 description 14
- 229940126214 compound 3 Drugs 0.000 description 13
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- 238000000926 separation method Methods 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 239000010408 film Substances 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- 238000007740 vapor deposition Methods 0.000 description 11
- 238000002156 mixing Methods 0.000 description 10
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 8
- 238000000151 deposition Methods 0.000 description 8
- 230000008021 deposition Effects 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 7
- 230000009477 glass transition Effects 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 150000001721 carbon Chemical group 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 6
- 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 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 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 5
- SNRCKKQHDUIRIY-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloromethane;dichloropalladium;iron(2+) Chemical compound [Fe+2].ClCCl.Cl[Pd]Cl.C1=C[CH-]C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.C1=C[CH-]C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 SNRCKKQHDUIRIY-UHFFFAOYSA-L 0.000 description 5
- 239000002198 insoluble material Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000002808 molecular sieve Substances 0.000 description 5
- 235000011056 potassium acetate Nutrition 0.000 description 5
- 239000002356 single layer Substances 0.000 description 5
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 5
- NCRIDSGPLISUEU-UHFFFAOYSA-N 2-bromo-6-pyridin-2-ylpyridine Chemical compound BrC1=CC=CC(C=2N=CC=CC=2)=N1 NCRIDSGPLISUEU-UHFFFAOYSA-N 0.000 description 4
- ZVFQEOPUXVPSLB-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-4-phenyl-5-(4-phenylphenyl)-1,2,4-triazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N1C=2C=CC=CC=2)=NN=C1C1=CC=C(C=2C=CC=CC=2)C=C1 ZVFQEOPUXVPSLB-UHFFFAOYSA-N 0.000 description 4
- WYFCZWSWFGJODV-MIANJLSGSA-N 4-[[(1s)-2-[(e)-3-[3-chloro-2-fluoro-6-(tetrazol-1-yl)phenyl]prop-2-enoyl]-5-(4-methyl-2-oxopiperazin-1-yl)-3,4-dihydro-1h-isoquinoline-1-carbonyl]amino]benzoic acid Chemical compound O=C1CN(C)CCN1C1=CC=CC2=C1CCN(C(=O)\C=C\C=1C(=CC=C(Cl)C=1F)N1N=NN=C1)[C@@H]2C(=O)NC1=CC=C(C(O)=O)C=C1 WYFCZWSWFGJODV-MIANJLSGSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 4
- 238000001179 sorption measurement Methods 0.000 description 4
- 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 3
- GZOLRAQBGRLGHQ-UHFFFAOYSA-N 1,2-bis(3-bromophenyl)benzene Chemical group BrC1=CC=CC(C=2C(=CC=CC=2)C=2C=C(Br)C=CC=2)=C1 GZOLRAQBGRLGHQ-UHFFFAOYSA-N 0.000 description 3
- IPFDSCVIIKPNHE-UHFFFAOYSA-N 2-pyridin-2-yl-6-[11-(6-pyridin-2-ylpyridin-2-yl)triphenylen-2-yl]pyridine Chemical group N1=CC=CC=C1C1=CC=CC(C=2C=C3C4=CC(=CC=C4C4=CC=CC=C4C3=CC=2)C=2N=C(C=CC=2)C=2N=CC=CC=2)=N1 IPFDSCVIIKPNHE-UHFFFAOYSA-N 0.000 description 3
- UZYOWEBSRYQJJO-UHFFFAOYSA-N 2-pyridin-2-yl-6-[7-(6-pyridin-2-ylpyridin-2-yl)triphenylen-2-yl]pyridine Chemical group N1=CC=CC=C1C1=CC=CC(C=2C=C3C4=CC=CC=C4C4=CC(=CC=C4C3=CC=2)C=2N=C(C=CC=2)C=2N=CC=CC=2)=N1 UZYOWEBSRYQJJO-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229910001316 Ag alloy Inorganic materials 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229940125797 compound 12 Drugs 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 239000007772 electrode material Substances 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 3
- 125000005956 isoquinolyl group Chemical group 0.000 description 3
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000005561 phenanthryl group Chemical group 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 125000003226 pyrazolyl group Chemical group 0.000 description 3
- 125000001725 pyrenyl group Chemical group 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 125000005493 quinolyl group Chemical group 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 235000010265 sodium sulphite Nutrition 0.000 description 3
- 125000005504 styryl group Chemical group 0.000 description 3
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- CJNMHWJZCGSVQG-UHFFFAOYSA-N 1,2-bis(4-bromophenyl)benzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1C1=CC=C(Br)C=C1 CJNMHWJZCGSVQG-UHFFFAOYSA-N 0.000 description 2
- BBOLNFYSRZVALD-UHFFFAOYSA-N 1,2-diiodobenzene Chemical compound IC1=CC=CC=C1I BBOLNFYSRZVALD-UHFFFAOYSA-N 0.000 description 2
- ZHXUWDPHUQHFOV-UHFFFAOYSA-N 2,5-dibromopyridine Chemical compound BrC1=CC=C(Br)N=C1 ZHXUWDPHUQHFOV-UHFFFAOYSA-N 0.000 description 2
- BPGPBYGXGRDFQG-UHFFFAOYSA-N 2,7-dibromotriphenylene Chemical group C1=CC=C2C3=CC(Br)=CC=C3C3=CC=C(Br)C=C3C2=C1 BPGPBYGXGRDFQG-UHFFFAOYSA-N 0.000 description 2
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 2
- FXYAAAYRITXMCM-UHFFFAOYSA-N 2-bromo-1-(2-bromo-3-methoxyphenyl)-3-methoxybenzene Chemical group COC1=CC=CC(C=2C(=C(OC)C=CC=2)Br)=C1Br FXYAAAYRITXMCM-UHFFFAOYSA-N 0.000 description 2
- VEKIYFGCEAJDDT-UHFFFAOYSA-N 2-pyridin-3-ylpyridine Chemical group N1=CC=CC=C1C1=CC=CN=C1 VEKIYFGCEAJDDT-UHFFFAOYSA-N 0.000 description 2
- ZDCWLNFPCAAJKO-UHFFFAOYSA-N 2-pyridin-4-yl-5-[7-(6-pyridin-4-ylpyridin-3-yl)triphenylen-2-yl]pyridine Chemical group C=1C=CC=C(C2=C3)C=1C1=CC(C=4C=NC(=CC=4)C=4C=CN=CC=4)=CC=C1C2=CC=C3C(C=N1)=CC=C1C1=CC=NC=C1 ZDCWLNFPCAAJKO-UHFFFAOYSA-N 0.000 description 2
- RMHQDKYZXJVCME-UHFFFAOYSA-N 2-pyridin-4-ylpyridine Chemical group N1=CC=CC=C1C1=CC=NC=C1 RMHQDKYZXJVCME-UHFFFAOYSA-N 0.000 description 2
- OBAJPWYDYFEBTF-UHFFFAOYSA-N 2-tert-butyl-9,10-dinaphthalen-2-ylanthracene Chemical compound C1=CC=CC2=CC(C3=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C4=CC=C(C=C43)C(C)(C)C)=CC=C21 OBAJPWYDYFEBTF-UHFFFAOYSA-N 0.000 description 2
- JMYWOTUPHRLJMO-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-[11-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)triphenylen-2-yl]-1,3,2-dioxaborolane Chemical group O1C(C)(C)C(C)(C)OB1C1=CC=C(C=2C(=CC=CC=2)C=2C3=CC(=CC=2)B2OC(C)(C)C(C)(C)O2)C3=C1 JMYWOTUPHRLJMO-UHFFFAOYSA-N 0.000 description 2
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 2
- AWJPULCSDFBFDR-UHFFFAOYSA-N 5-bromo-2-pyridin-2-ylpyridine Chemical compound N1=CC(Br)=CC=C1C1=CC=CC=N1 AWJPULCSDFBFDR-UHFFFAOYSA-N 0.000 description 2
- SPRDWKWZBQDQNI-UHFFFAOYSA-N 5-bromo-2-pyridin-4-ylpyridine Chemical compound N1=CC(Br)=CC=C1C1=CC=NC=C1 SPRDWKWZBQDQNI-UHFFFAOYSA-N 0.000 description 2
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 2
- 0 CCCC(C)(C)c1cc2c(C=C(C(C)(C)CCC3CC3)C=*=C3)c3c(C=[Tl]C=C3)c3c2cc1 Chemical compound CCCC(C)(C)c1cc2c(C=C(C(C)(C)CCC3CC3)C=*=C3)c3c(C=[Tl]C=C3)c3c2cc1 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 description 2
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 2
- BAHGLTLEMLDWAA-UHFFFAOYSA-N [11-(trifluoromethylsulfonyloxy)triphenylen-2-yl] trifluoromethanesulfonate Chemical compound C1=C(OS(=O)(=O)C(F)(F)F)C=C2C3=CC(OS(=O)(=O)C(F)(F)F)=CC=C3C3=CC=CC=C3C2=C1 BAHGLTLEMLDWAA-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N c1ccncc1 Chemical compound c1ccncc1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 150000001716 carbazoles Chemical class 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000006880 cross-coupling reaction Methods 0.000 description 2
- 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 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000007978 oxazole derivatives Chemical class 0.000 description 2
- 150000005041 phenanthrolines Chemical class 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 150000004322 quinolinols Chemical class 0.000 description 2
- 230000027756 respiratory electron transport chain Effects 0.000 description 2
- 150000003918 triazines Chemical class 0.000 description 2
- 239000013638 trimer Substances 0.000 description 2
- AZSDXVAHZQWAEJ-UHFFFAOYSA-N trimethyl-[3-[2-(3-trimethylsilylphenyl)phenyl]phenyl]silane Chemical group C[Si](C)(C)C1=CC=CC(C=2C(=CC=CC=2)C=2C=C(C=CC=2)[Si](C)(C)C)=C1 AZSDXVAHZQWAEJ-UHFFFAOYSA-N 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
- DETFWTCLAIIJRZ-UHFFFAOYSA-N triphenyl-(4-triphenylsilylphenyl)silane Chemical compound C1=CC=CC=C1[Si](C=1C=CC(=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 DETFWTCLAIIJRZ-UHFFFAOYSA-N 0.000 description 2
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 2
- 125000006617 triphenylamine group Chemical group 0.000 description 2
- AMBHXBFZKPCREF-UHFFFAOYSA-N triphenylene-2,11-diol Chemical compound C1=C(O)C=C2C3=CC(O)=CC=C3C3=CC=CC=C3C2=C1 AMBHXBFZKPCREF-UHFFFAOYSA-N 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- ZQJYTTPJYLKTTI-UHFFFAOYSA-M zinc;2h-pyridin-2-ide;bromide Chemical compound Br[Zn+].C1=CC=N[C-]=C1 ZQJYTTPJYLKTTI-UHFFFAOYSA-M 0.000 description 2
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 1
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 1
- 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
- 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
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 1
- YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 description 1
- VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 description 1
- ITOFPJRDSCGOSA-KZLRUDJFSA-N (2s)-2-[[(4r)-4-[(3r,5r,8r,9s,10s,13r,14s,17r)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H](CC[C@]13C)[C@@H]2[C@@H]3CC[C@@H]1[C@H](C)CCC(=O)N[C@H](C(O)=O)CC1=CNC2=CC=CC=C12 ITOFPJRDSCGOSA-KZLRUDJFSA-N 0.000 description 1
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 1
- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 1
- REMKRZLFPLDTKR-UHFFFAOYSA-N (3-trimethylsilylphenyl)boronic acid Chemical compound C[Si](C)(C)C1=CC=CC(B(O)O)=C1 REMKRZLFPLDTKR-UHFFFAOYSA-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
- UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 description 1
- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 1
- MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 description 1
- OMBVEVHRIQULKW-DNQXCXABSA-M (3r,5r)-7-[3-(4-fluorophenyl)-8-oxo-7-phenyl-1-propan-2-yl-5,6-dihydro-4h-pyrrolo[2,3-c]azepin-2-yl]-3,5-dihydroxyheptanoate Chemical compound O=C1C=2N(C(C)C)C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C(C=3C=CC(F)=CC=3)C=2CCCN1C1=CC=CC=C1 OMBVEVHRIQULKW-DNQXCXABSA-M 0.000 description 1
- NRPZMSUGPMYBCQ-UHFFFAOYSA-N (4-trimethylsilylphenyl)boronic acid Chemical compound C[Si](C)(C)C1=CC=C(B(O)O)C=C1 NRPZMSUGPMYBCQ-UHFFFAOYSA-N 0.000 description 1
- YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 description 1
- ZYZCALPXKGUGJI-DDVDASKDSA-M (e,3r,5s)-7-[3-(4-fluorophenyl)-2-phenyl-5-propan-2-ylimidazol-4-yl]-3,5-dihydroxyhept-6-enoate Chemical compound C=1C=C(F)C=CC=1N1C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C(C(C)C)N=C1C1=CC=CC=C1 ZYZCALPXKGUGJI-DDVDASKDSA-M 0.000 description 1
- DIOHEXPTUTVCNX-UHFFFAOYSA-N 1,1,1-trifluoro-n-phenyl-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)N(S(=O)(=O)C(F)(F)F)C1=CC=CC=C1 DIOHEXPTUTVCNX-UHFFFAOYSA-N 0.000 description 1
- WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical compound BrC1=CC=CC=C1Br WQONPSCCEXUXTQ-UHFFFAOYSA-N 0.000 description 1
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 1
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-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
- UCHNVSDXSPIKRG-UHFFFAOYSA-N 1-methoxy-3-(3-methoxyphenyl)benzene Chemical group COC1=CC=CC(C=2C=C(OC)C=CC=2)=C1 UCHNVSDXSPIKRG-UHFFFAOYSA-N 0.000 description 1
- XNCMQRWVMWLODV-UHFFFAOYSA-N 1-phenylbenzimidazole Chemical compound C1=NC2=CC=CC=C2N1C1=CC=CC=C1 XNCMQRWVMWLODV-UHFFFAOYSA-N 0.000 description 1
- GTPBIVBFUOMIBT-UHFFFAOYSA-N 2,11-dimethoxytriphenylene Chemical group C1=C(OC)C=C2C3=CC(OC)=CC=C3C3=CC=CC=C3C2=C1 GTPBIVBFUOMIBT-UHFFFAOYSA-N 0.000 description 1
- FEYDZHNIIMENOB-UHFFFAOYSA-N 2,6-dibromopyridine Chemical compound BrC1=CC=CC(Br)=N1 FEYDZHNIIMENOB-UHFFFAOYSA-N 0.000 description 1
- FQMZXMVHHKXGTM-UHFFFAOYSA-N 2-(1-adamantyl)-n-[2-[2-(2-hydroxyethylamino)ethylamino]quinolin-5-yl]acetamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=CC=CC2=NC(NCCNCCO)=CC=C21 FQMZXMVHHKXGTM-UHFFFAOYSA-N 0.000 description 1
- GGFGKPIRBWSNSY-UHFFFAOYSA-N 2-(2h-pyridin-1-yl)pyridine Chemical compound C1C=CC=CN1C1=CC=CC=N1 GGFGKPIRBWSNSY-UHFFFAOYSA-N 0.000 description 1
- RIKNNBBGYSDYAX-UHFFFAOYSA-N 2-[1-[2-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]-n,n-bis(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C(=CC=CC=1)C1(CCCCC1)C=1C(=CC=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 RIKNNBBGYSDYAX-UHFFFAOYSA-N 0.000 description 1
- BDOYKFSQFYNPKF-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]ethyl-(carboxymethyl)amino]acetic acid;sodium Chemical compound [Na].[Na].OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O BDOYKFSQFYNPKF-UHFFFAOYSA-N 0.000 description 1
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 1
- PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 description 1
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 1
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 1
- NPRYCHLHHVWLQZ-TURQNECASA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one Chemical compound NC1=NC=C2N(C(N(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C NPRYCHLHHVWLQZ-TURQNECASA-N 0.000 description 1
- LFOIDLOIBZFWDO-UHFFFAOYSA-N 2-methoxy-6-[6-methoxy-4-[(3-phenylmethoxyphenyl)methoxy]-1-benzofuran-2-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(C=1)=CC=CC=1OCC1=CC=CC=C1 LFOIDLOIBZFWDO-UHFFFAOYSA-N 0.000 description 1
- WXNYCQRAJCGMGJ-UHFFFAOYSA-N 2-phenyl-n-(2-phenylphenyl)-n-[4-[4-(2-phenyl-n-(2-phenylphenyl)anilino)phenyl]phenyl]aniline Chemical compound C1=CC=CC=C1C1=CC=CC=C1N(C=1C(=CC=CC=1)C=1C=CC=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C(=CC=CC=2)C=2C=CC=CC=2)C=2C(=CC=CC=2)C=2C=CC=CC=2)C=C1 WXNYCQRAJCGMGJ-UHFFFAOYSA-N 0.000 description 1
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 1
- UVWDAPYWHSWYFZ-UHFFFAOYSA-N 2-pyridin-2-yl-5-[11-(6-pyridin-2-ylpyridin-3-yl)triphenylen-2-yl]pyridine Chemical group N1=CC=CC=C1C1=CC=C(C=2C=C3C4=CC(=CC=C4C4=CC=CC=C4C3=CC=2)C=2C=NC(=CC=2)C=2N=CC=CC=2)C=N1 UVWDAPYWHSWYFZ-UHFFFAOYSA-N 0.000 description 1
- YAELXYZSNJSOCR-UHFFFAOYSA-N 2-pyridin-2-yl-5-[7-(6-pyridin-2-ylpyridin-3-yl)triphenylen-2-yl]pyridine Chemical group N1=CC=CC=C1C1=CC=C(C=2C=C3C4=CC=CC=C4C4=CC(=CC=C4C3=CC=2)C=2C=NC(=CC=2)C=2N=CC=CC=2)C=N1 YAELXYZSNJSOCR-UHFFFAOYSA-N 0.000 description 1
- VVJKFZOOFYHKRU-UHFFFAOYSA-N 2-tert-butyl-9,10-diphenylanthracene Chemical compound C=12C=CC=CC2=C(C=2C=CC=CC=2)C2=CC(C(C)(C)C)=CC=C2C=1C1=CC=CC=C1 VVJKFZOOFYHKRU-UHFFFAOYSA-N 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 1
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 1
- VCTMQXIOUDZIGS-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=CC=C1B1OC(C)(C)C(C)(C)O1 VCTMQXIOUDZIGS-UHFFFAOYSA-N 0.000 description 1
- PGKQJNOISHJIBI-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-[7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)triphenylen-2-yl]-1,3,2-dioxaborolane Chemical group O1C(C)(C)C(C)(C)OB1C1=CC=C(C=2C(=CC(=CC=2)B2OC(C)(C)C(C)(C)O2)C=2C3=CC=CC=2)C3=C1 PGKQJNOISHJIBI-UHFFFAOYSA-N 0.000 description 1
- FJXNABNMUQXOHX-UHFFFAOYSA-N 4-(9h-carbazol-1-yl)-n,n-bis[4-(9h-carbazol-1-yl)phenyl]aniline Chemical compound C12=CC=CC=C2NC2=C1C=CC=C2C(C=C1)=CC=C1N(C=1C=CC(=CC=1)C=1C=2NC3=CC=CC=C3C=2C=CC=1)C(C=C1)=CC=C1C1=C2NC3=CC=CC=C3C2=CC=C1 FJXNABNMUQXOHX-UHFFFAOYSA-N 0.000 description 1
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 1
- HCCNBKFJYUWLEX-UHFFFAOYSA-N 7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)-3-(pyrazin-2-ylmethylamino)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NCC1=CN=CC=N1 HCCNBKFJYUWLEX-UHFFFAOYSA-N 0.000 description 1
- MZYDBGLUVPLRKR-UHFFFAOYSA-N 9-(3-carbazol-9-ylphenyl)carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=CC=C1 MZYDBGLUVPLRKR-UHFFFAOYSA-N 0.000 description 1
- FOUNKDBOYUMWNP-UHFFFAOYSA-N 9-[4-[2-(4-carbazol-9-ylphenyl)-2-adamantyl]phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C(C=C1)=CC=C1C1(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C(C2)CC3CC1CC2C3 FOUNKDBOYUMWNP-UHFFFAOYSA-N 0.000 description 1
- GFEWJHOBOWFNRV-UHFFFAOYSA-N 9-[4-[9-(4-carbazol-9-ylphenyl)fluoren-9-yl]phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C(C=C1)=CC=C1C1(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C2=CC=CC=C2C2=CC=CC=C12 GFEWJHOBOWFNRV-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- ISMDILRWKSYCOD-GNKBHMEESA-N C(C1=CC=CC=C1)[C@@H]1NC(OCCCCCCCCCCCNC([C@@H](NC(C[C@@H]1O)=O)C(C)C)=O)=O Chemical compound C(C1=CC=CC=C1)[C@@H]1NC(OCCCCCCCCCCCNC([C@@H](NC(C[C@@H]1O)=O)C(C)C)=O)=O ISMDILRWKSYCOD-GNKBHMEESA-N 0.000 description 1
- NVPCUINUAGDUMY-UHFFFAOYSA-N C1=CC(c(cc2)cc3c2c(cccc2)c2c(cc2)c3cc2-c2cnc(C(C=C3)NC=C3c(cc3)ncc3-c3ccccn3)cc2)=C[N-]C1c(nc1)ccc1-c(cc1)ncc1-c1ccccn1 Chemical compound C1=CC(c(cc2)cc3c2c(cccc2)c2c(cc2)c3cc2-c2cnc(C(C=C3)NC=C3c(cc3)ncc3-c3ccccn3)cc2)=C[N-]C1c(nc1)ccc1-c(cc1)ncc1-c1ccccn1 NVPCUINUAGDUMY-UHFFFAOYSA-N 0.000 description 1
- DWVYSEVIUODICL-UHFFFAOYSA-N C1=CC=C(c2ccc(c(ccc(-c3nc(-c4ccccn4)ccc3)c3)c3c3ccccc33)c3c2)[N-]C1c1ccccn1 Chemical compound C1=CC=C(c2ccc(c(ccc(-c3nc(-c4ccccn4)ccc3)c3)c3c3ccccc33)c3c2)[N-]C1c1ccccn1 DWVYSEVIUODICL-UHFFFAOYSA-N 0.000 description 1
- XSRPBXCRFJQHQD-UHFFFAOYSA-N C1=CC=C[N-]C1c(cc1)cnc1-c1ccc(c2ccccc2c(cc2)c3cc2-c(cc2)ncc2-c2ccccn2)c3c1 Chemical compound C1=CC=C[N-]C1c(cc1)cnc1-c1ccc(c2ccccc2c(cc2)c3cc2-c(cc2)ncc2-c2ccccn2)c3c1 XSRPBXCRFJQHQD-UHFFFAOYSA-N 0.000 description 1
- YXBSPEDTBVJVAY-UHFFFAOYSA-N C1=CN=[I]C=C1 Chemical compound C1=CN=[I]C=C1 YXBSPEDTBVJVAY-UHFFFAOYSA-N 0.000 description 1
- OJRUSAPKCPIVBY-KQYNXXCUSA-N C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N Chemical compound C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N OJRUSAPKCPIVBY-KQYNXXCUSA-N 0.000 description 1
- LOMYJZJZVWSPLK-UHFFFAOYSA-N C1[N-]C(c2ccc(C3=CC=C(c4cccnc4)[N-]C3)nc2)=CC=C1c(cc1)cc2c1c(ccc(-c1ccc(-c(cc3)cnc3-c3ccc(-c4cnccc4)nc3)nc1)c1)c1c1c2cccc1 Chemical compound C1[N-]C(c2ccc(C3=CC=C(c4cccnc4)[N-]C3)nc2)=CC=C1c(cc1)cc2c1c(ccc(-c1ccc(-c(cc3)cnc3-c3ccc(-c4cnccc4)nc3)nc1)c1)c1c1c2cccc1 LOMYJZJZVWSPLK-UHFFFAOYSA-N 0.000 description 1
- MCJYCSYDFGHJDH-UHFFFAOYSA-N C=[I-]1[NH+]=C=CC=C1 Chemical compound C=[I-]1[NH+]=C=CC=C1 MCJYCSYDFGHJDH-UHFFFAOYSA-N 0.000 description 1
- SBDMPLDJOXSUPO-UHFFFAOYSA-N CC1(c(cc2)cnc2-c2cnccc2)N=CC(c2cc3c(cc(cc4)-c5ccc(-c(cc6)cnc6-c6cccnc6)nc5)c4c(cccc4)c4c3cc2)=CC1 Chemical compound CC1(c(cc2)cnc2-c2cnccc2)N=CC(c2cc3c(cc(cc4)-c5ccc(-c(cc6)cnc6-c6cccnc6)nc5)c4c(cccc4)c4c3cc2)=CC1 SBDMPLDJOXSUPO-UHFFFAOYSA-N 0.000 description 1
- KCBAMQOKOLXLOX-BSZYMOERSA-N CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O Chemical compound CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O KCBAMQOKOLXLOX-BSZYMOERSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical class [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 1
- 229940126657 Compound 17 Drugs 0.000 description 1
- 229940126639 Compound 33 Drugs 0.000 description 1
- 229940127007 Compound 39 Drugs 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 229910000846 In alloy Inorganic materials 0.000 description 1
- 229910000861 Mg alloy Inorganic materials 0.000 description 1
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 1
- 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 1
- 239000007983 Tris buffer Substances 0.000 description 1
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 1
- SPXSEZMVRJLHQG-XMMPIXPASA-N [(2R)-1-[[4-[(3-phenylmethoxyphenoxy)methyl]phenyl]methyl]pyrrolidin-2-yl]methanol Chemical compound C(C1=CC=CC=C1)OC=1C=C(OCC2=CC=C(CN3[C@H](CCC3)CO)C=C2)C=CC=1 SPXSEZMVRJLHQG-XMMPIXPASA-N 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
- PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 description 1
- MJOQJPYNENPSSS-XQHKEYJVSA-N [(3r,4s,5r,6s)-4,5,6-triacetyloxyoxan-3-yl] acetate Chemical compound CC(=O)O[C@@H]1CO[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O MJOQJPYNENPSSS-XQHKEYJVSA-N 0.000 description 1
- FUHDUDFIRJUPIV-UHFFFAOYSA-N [4-[9-(4-carbazol-9-ylphenyl)fluoren-9-yl]phenyl]-triphenylsilane Chemical compound C1=CC=CC=C1[Si](C=1C=CC(=CC=1)C1(C2=CC=CC=C2C2=CC=CC=C21)C=1C=CC(=CC=1)N1C2=CC=CC=C2C2=CC=CC=C21)(C=1C=CC=CC=1)C1=CC=CC=C1 FUHDUDFIRJUPIV-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 description 1
- 125000004062 acenaphthenyl group Chemical group C1(CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 1
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- 150000001454 anthracenes Chemical class 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
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 150000001562 benzopyrans Chemical class 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- PGMDUIGGQGCZIX-UHFFFAOYSA-N c(cc1c2c3)ccc1c(cc(cc1)-c4cc(-c5ncccc5)cnc4)c1c2ccc3-c1cc(-c2ncccc2)cnc1 Chemical compound c(cc1c2c3)ccc1c(cc(cc1)-c4cc(-c5ncccc5)cnc4)c1c2ccc3-c1cc(-c2ncccc2)cnc1 PGMDUIGGQGCZIX-UHFFFAOYSA-N 0.000 description 1
- IAVZDVZJDQUERS-UHFFFAOYSA-N c1cc(-c(nc2)ccc2-c2cc3c(ccc(-c(cc4)cnc4-c4ncccc4)c4)c4c(ccc(-c4ccc(-c5ncccc5)nc4)c4)c4c3cc2)ncc1 Chemical compound c1cc(-c(nc2)ccc2-c2cc3c(ccc(-c(cc4)cnc4-c4ncccc4)c4)c4c(ccc(-c4ccc(-c5ncccc5)nc4)c4)c4c3cc2)ncc1 IAVZDVZJDQUERS-UHFFFAOYSA-N 0.000 description 1
- DRKGVUORUFOUDU-UHFFFAOYSA-N c1ccnc(-c(cc2)ncc2-c(nc2)ccc2-c2cc3c(ccc(-c(cc4)cnc4-c4ccc(-c5ccccn5)nc4)c4)c4c(ccc(-c4ccc(-c(cc5)cnc5-c5ccccn5)nc4)c4)c4c3cc2)c1 Chemical compound c1ccnc(-c(cc2)ncc2-c(nc2)ccc2-c2cc3c(ccc(-c(cc4)cnc4-c4ccc(-c5ccccn5)nc4)c4)c4c(ccc(-c4ccc(-c(cc5)cnc5-c5ccccn5)nc4)c4)c4c3cc2)c1 DRKGVUORUFOUDU-UHFFFAOYSA-N 0.000 description 1
- BEGQASDMOHAXHQ-UHFFFAOYSA-N c1cncc(-c(cc2)cnc2-c(nc2)ccc2-c(cc2)cc3c2c(cc(cc2)-c(cc4)cnc4-c(nc4)ccc4-c4cnccc4)c2c2c3ccc(-c3ccc(-c(cc4)ncc4-c4cccnc4)nc3)c2)c1 Chemical compound c1cncc(-c(cc2)cnc2-c(nc2)ccc2-c(cc2)cc3c2c(cc(cc2)-c(cc4)cnc4-c(nc4)ccc4-c4cnccc4)c2c2c3ccc(-c3ccc(-c(cc4)ncc4-c4cccnc4)nc3)c2)c1 BEGQASDMOHAXHQ-UHFFFAOYSA-N 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
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940125773 compound 10 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
- 229940126086 compound 21 Drugs 0.000 description 1
- 229940126208 compound 22 Drugs 0.000 description 1
- 229940125833 compound 23 Drugs 0.000 description 1
- 229940125961 compound 24 Drugs 0.000 description 1
- 229940125846 compound 25 Drugs 0.000 description 1
- 229940125851 compound 27 Drugs 0.000 description 1
- 229940127204 compound 29 Drugs 0.000 description 1
- 229940125877 compound 31 Drugs 0.000 description 1
- 229940125878 compound 36 Drugs 0.000 description 1
- 229940125807 compound 37 Drugs 0.000 description 1
- 229940127573 compound 38 Drugs 0.000 description 1
- 229940126540 compound 41 Drugs 0.000 description 1
- 229940125936 compound 42 Drugs 0.000 description 1
- 229940125844 compound 46 Drugs 0.000 description 1
- 229940127271 compound 49 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 229940126545 compound 53 Drugs 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- PDKHNCYLMVRIFV-UHFFFAOYSA-H molybdenum;hexachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mo] PDKHNCYLMVRIFV-UHFFFAOYSA-H 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 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
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 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
- XEXYATIPBLUGSF-UHFFFAOYSA-N phenanthro[9,10-b]pyridine-2,3,4,5,6,7-hexacarbonitrile Chemical group N1=C(C#N)C(C#N)=C(C#N)C2=C(C(C#N)=C(C(C#N)=C3)C#N)C3=C(C=CC=C3)C3=C21 XEXYATIPBLUGSF-UHFFFAOYSA-N 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- QLULGIRFKAWHOJ-UHFFFAOYSA-N pyridin-4-ylboronic acid Chemical compound OB(O)C1=CC=NC=C1 QLULGIRFKAWHOJ-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical class [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 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
- 150000003839 salts Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 150000003967 siloles Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [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 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/22—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing two or more pyridine rings directly linked together, e.g. bipyridyl
-
- 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
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- 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
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
-
- 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]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
- H10K50/165—Electron transporting layers comprising dopants
-
- 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]
- H10K50/17—Carrier injection layers
- H10K50/171—Electron injection 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/18—Bridged systems
-
- 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
- C09K2211/14—Macromolecular compounds
- C09K2211/1408—Carbocyclic compounds
- C09K2211/1425—Non-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Pyridine Compounds (AREA)
Abstract
Description
ここで、R1〜R8、R19〜R27、R40〜R47で表される、「置換もしくは無置換の芳香族複素環基」として、置換もしくは無置換のピリジル基が好ましく、電子注入特性の向上が期待できる。
ここで、トリフェニレン環に結合するビピリジル基(一般式(1)もしくは一般式(2)において、n1〜n5が2である場合)としては、2,2’−ビピリジル基、2,3’−ビピリジル基、2,4’−ビピリジル基、3,2’−ビピリジル基が好ましく、2,2’−ビピリジル基、2,4’−ビピリジル基が特に好ましい。
一方、種々の置換基を有するハロゲノビピリジンをビス(ピナコラート)ジボロンなどによるボロン酸エステル化を行うことによって、種々の置換基を有するビピリジンのボロン酸エステル体を合成し、さらに、この種々の置換基を有するビピリジンのボロン酸エステル体と相当するトリフェニレン化合物のジハライドとをSuzukiカップリングなどのクロスカップリング反応を行うことによって、置換されたビピリジル基とトリフェニレン環構造を有する化合物を合成することができる。
窒素置換した反応容器に、2,5−ジブロモピリジン19.5g、2−ピリジルジンクブロマイド150ml、テトラヒドロフラン90ml、テトラキス(トリフェニルホスフィン)パラジウム(0)4.33gを加えて冷却し、0℃で2時間攪拌した後、さらに室温で3時間攪拌した。反応溶液を10%エチレンジアミン四酢酸二水素二ナトリウム水溶液に加えて6時間攪拌した後、クロロホルム300mlを加え、分液操作を行うことによって有機層を採取した。有機層を無水硫酸マグネシウムで脱水した後、濃縮することによって粗製物を得た。粗製物をカラムクロマトグラフ(担体:シリカゲル、溶離液:トルエン)によって精製し、5−ブロモ−2,2’−ビピリジンの白色粉末11.1g(収率63%)を得た。
窒素置換した反応容器に、2,6−ジブロモピリジン19.5g、2−ピリジルジンクブロマイド150ml、テトラヒドロフラン90ml、テトラキス(トリフェニルホスフィン)パラジウム(0)4.33gを加えて冷却し、0℃で2時間攪拌した後、さらに室温で3時間攪拌した。反応溶液を10%エチレンジアミン四酢酸二水素二ナトリウム水溶液に加えて6時間撹拌した後、クロロホルム300mlを加え、分液操作を行うことによって有機層を採取した。有機層を無水硫酸マグネシウムで脱水した後、濃縮することによって粗製物を得た。粗製物をカラムクロマトグラフ(担体:シリカゲル、溶離液:トルエン)によって精製し、6−ブロモ−2,2’−ビピリジンの白色粉末11.1g(収率63%)を得た。
窒素置換した反応容器に、1,2−ジブロモベンゼン10g、ビス(ピナコラート)ジボロン23.7g、酢酸カリウム12.5g、予めモレキュラーシーブス4Aで脱水した1,4−ジオキサン150ml、[1,1’−ビス(ジフェニルホスフィノ)フェロセン]パラジウム(II)ジクロリド−ジクロロメタン錯体(1:1)1.0gを加えて加熱し、80℃で10時間攪拌した。50℃まで冷却した後、クロロホルム150mlを加え、30分攪拌した。ろ過によって不溶物を除き、濃縮することによって粗製物を得た。粗製物をカラムクロマトグラフ[担体:シリカゲル、溶離液:酢酸エチル/n−ヘキサン=1/4(v/v)]によって精製し、1,2−ビス(4,4,5,5−テトラメチル−[1,3,2]ジオキサボロラン−2−イル)ベンゼンの白色粉末7.2g(収率54%)を得た。
実施例3で合成した2,11−ビス(4,4,5,5−テトラメチル−[1,3,2]ジオキサボロラン−2−イル)トリフェニレン0.8g、実施例2で合成した6−ブロモ−2,2’−ビピリジン0.8g、2M炭酸カリウム水溶液2.3ml、テトラキス(トリフェニルホスフィン)パラジウム(0)0.1g、トルエン40ml、エタノール10mlを窒素置換した反応容器に加えて加熱し、攪拌しながら9時間還流した。室温まで冷却し、析出物をろ過によって採取した。析出物にクロロホルム1300mlを加え、不溶物をろ過によって除いた後、1,2−ジクロロベンゼンによる再結晶によって精製し、2,11−ビス(2,2’−ビピリジン−6−イル)トリフェニレン(化合物12)の淡黄白色粉末0.6g(収率71%)を得た。
窒素置換した反応容器に、2,5−ジブロモピリジン9.6g、4−ピリジンボロン酸2.5g、トルエン50ml、エタノール40ml、2M炭酸カリウム水溶液15.2ml、テトラキス(トリフェニルホスフィン)パラジウム(0)1.50gを加えて加熱し、攪拌しながら24時間還流した。室温まで冷却した後、クロロホルム500mlと水300mlを加え、分液操作を行うことによって有機層を採取した。有機層を水100mlで2回洗浄した後、無水硫酸マグネシウムで脱水した後、濃縮することによって粗製物を得た。粗製物をカラムクロマトグラフ[担体:シリカゲル、溶離液:トルエン:酢酸エチル=1:1(v/v)]によって精製し、5−ブロモ−2,4’−ビピリジンの白色粉末3.3g(収率69%)を得た。
元素分析、測定値:C;85.08、H;4.42、N;10.39、計算値(C38H24N4):C;85.05、H;4.51、N;10.44。
<3,3’’−ビス(2,2’−ビピリジン−5−イル)−1,1’:2’,1’’−ターフェニル(比較化合物1)の合成>
1H−NMR(CDCl3)で以下の26個の水素のシグナルを検出した。δ(ppm)=8.65−8.66(2H)、8.51−8.53(2H)、8.31−8.33(2H)、8.08(2H)、7.99−8.01(2H)、7.71−7.79(4H)、7.59−7.61(2H)、7.54−7.56(2H)、7.50−7.52(2H)、7.34−7.38(2H)、7.25−7.28(4H)。
<3,3’’−ビス(2,2’−ビピリジン−6−イル)−1,1’:2’,1’’−ターフェニル(比較化合物2)の合成>
1H−NMR(CDCl3)で以下の26個の水素のシグナルを検出した。δ(ppm)=8.66−8.68(4H)、8.35−8.40(4H)、7.79−7.83(2H)、7.69−7.72(2H)、7.45−7.58(8H)、7.35−7.39(4H)、7.28−7.31(2H)。
<4,4’’−ビス(2,2’−ビピリジン−6−イル)−1,1’:2’,1’’−ターフェニル(比較化合物3)の合成>
1H−NMR(CDCl3)で以下の26個の水素のシグナルを検出した。δ(ppm)=8.67(2H)、8.60(2H)、8.33(2H),8.06(4H)、7.78−7.86(4H)、7.74(2H)、7.53−7.48(4H)、7.36(4H)、7.30−7.28(2H)。
融点 ガラス転移点
本発明実施例1の化合物 338℃ なし
本発明実施例2の化合物 285℃ なし
仕事関数
本発明実施例1の化合物 5.74eV
本発明実施例2の化合物 5.69eV
本発明実施例3の化合物 5.82eV
本発明実施例4の化合物 5.73eV
本発明実施例5の化合物 6.21eV
比較のために、実施例8における電子輸送層5の材料をAlq3に代え、実施例8と同様の条件で有機EL素子を作製した。作製した有機EL素子について、大気中、常温で特性測定を行なった。作製した有機EL素子に直流電圧を印加したときの発光特性の測定結果を表1にまとめて示した。
比較のために、実施例8における電子輸送層5の材料を前記比較化合物1に代え、実施例8と同様の条件で有機EL素子を作製した。作製した有機EL素子について、大気中、常温で特性測定を行なった。作製した有機EL素子に直流電圧を印加したときの発光特性の測定結果を表1にまとめて示した。
比較のために、実施例8における電子輸送層5の材料を前記比較化合物2に代え、実施例8と同様の条件で有機EL素子を作製した。作製した有機EL素子について、大気中、常温で特性測定を行なった。作製した有機EL素子に直流電圧を印加したときの発光特性の測定結果を表1にまとめて示した。
比較のために、実施例8における電子輸送層5の材料を前記比較化合物3に代え、実施例8と同様の条件で有機EL素子を作製した。作製した有機EL素子について、大気中、常温で特性測定を行なった。作製した有機EL素子に直流電圧を印加したときの発光特性の測定結果を表1にまとめて示した。
比較のために、実施例11における電子輸送層5の材料をAlq3に代え、実施例11と同様の条件で有機EL素子を作製した。作製した有機EL素子について、大気中、常温で特性測定を行なった。作製した有機EL素子に直流電圧を印加したときの発光特性の測定結果を表2にまとめて示した。
2 透明陽極
3 正孔輸送層
4 発光層
5 電子輸送層
6 電子注入層
7 陰極
Claims (9)
- 下記一般式(1)または(2)で表される、置換されたビピリジル基とトリフェニレン環構造を有する化合物。
(式中、R1〜R18は、同一でも異なってもよく水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、トリフルオロメチル基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキル基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、n1、n2は、同一でも異なってもよく2または3を表す。n1、n2が2の場合はトリフェニレン環構造が2,2’−ビピリジル基で置換されたものでないものとする。ここで、複数個存在するR3〜R8はそれぞれ互いに同一でも異なってもよい。)
(式中、R19〜R39は、同一でも異なってもよく水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、トリフルオロメチル基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキル基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、n3、n4、n5は、同一でも異なってもよく2または3を表す。n3、n4、n5が2の場合はトリフェニレン環構造が2,2’−ビピリジル基で置換されたものでないものとする。ここで、複数個存在するR22〜R30はそれぞれ互いに同一でも異なってもよい。) - 下記一般式(1’)で表される、請求項1記載の置換されたビピリジル基とトリフェニレン環構造を有する化合物。
(式中、R1〜R18は、同一でも異なってもよく水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、トリフルオロメチル基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキル基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、n1、n2は、同一でも異なってもよく2または3を表す。n1、n2が2の場合はトリフェニレン環構造が2,2’−ビピリジル基で置換されたものでないものとする。ここで、複数個存在するR3〜R8はそれぞれ互いに同一でも異なってもよい。) - 下記一般式(1’’)で表される、請求項1記載の置換されたビピリジル基とトリフェニレン環構造を有する化合物。
(式中、R1〜R18は、同一でも異なってもよく水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、トリフルオロメチル基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキル基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、n1、n2は、同一でも異なってもよく2または3を表す。n1、n2が2の場合はトリフェニレン環構造が2,2’−ビピリジル基で置換されたものでないものとする。ここで、複数個存在するR3〜R8はそれぞれ互いに同一でも異なってもよい。) - 下記一般式(2’)で表される、請求項1記載の置換されたビピリジル基とトリフェニレン環構造を有する化合物。
(式中、R19〜R39は、同一でも異なってもよく水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、トリフルオロメチル基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキル基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、n3、n4、n5は、同一でも異なってもよく2または3を表す。n3、n4、n5が2の場合はトリフェニレン環構造が2,2’−ビピリジル基で置換されたものでないものとする。ここで、複数個存在するR22〜R30はそれぞれ互いに同一でも異なってもよい。) - 一対の電極とその間に挟まれた少なくとも一層の有機層を有する有機エレクトロルミネッセンス素子において、下記一般式(1)または(2)で表される、置換されたビピリジル基とトリフェニレン環構造を有する化合物が、少なくとも1つの有機層の構成材料として用いられていることを特徴とする有機エレクトロルミネッセンス素子。
(式中、R1〜R18は、同一でも異なってもよく水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、トリフルオロメチル基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキル基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、n1、n2は、同一でも異なってもよく2または3を表す。n1、n2が2の場合はトリフェニレン環構造が2,2’−ビピリジル基で置換されたものでないものとする。ここで、複数個存在するR3〜R8はそれぞれ互いに同一でも異なってもよい。)
(式中、R19〜R39は、同一でも異なってもよく水素原子、重水素原子、フッ素原子、塩素原子、シアノ基、トリフルオロメチル基、置換基を有していてもよい炭素原子数1ないし6の直鎖状もしくは分岐状のアルキル基、置換もしくは無置換の芳香族炭化水素基、置換もしくは無置換の芳香族複素環基または置換もしくは無置換の縮合多環芳香族基を表し、n3、n4、n5は、同一でも異なってもよく2または3を表す。n3、n4、n5が2の場合はトリフェニレン環構造が2,2’−ビピリジル基で置換されたものでないものとする。ここで、複数個存在するR22〜R30はそれぞれ互いに同一でも異なってもよい。) - 前記した有機層が電子輸送層であり、上記一般式(1)または(2)で表される化合物が、該電子輸送層中に、少なくとも一つの構成材料として用いられていることを特徴とする請求項6記載の有機エレクトロルミネッセンス素子。
- 前記した有機層が電子注入層であり、上記一般式(1)または(2)で表される化合物が、該電子注入層中に、少なくとも一つの構成材料として用いられていることを特徴とする請求項6記載の有機エレクトロルミネッセンス素子。
- 前記した有機層が発光層であり、上記一般式(1)または(2)で表される化合物が、該発光層中に、少なくとも一つの構成材料として用いられていることを特徴とする請求項6記載の有機エレクトロルミネッセンス素子。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2013256692A JP5861843B2 (ja) | 2011-02-23 | 2013-12-12 | 置換されたトリフェニレン環構造を有する化合物および有機エレクトロルミネッセンス素子 |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2011037322 | 2011-02-23 | ||
JP2011037322 | 2011-02-23 | ||
JP2013256692A JP5861843B2 (ja) | 2011-02-23 | 2013-12-12 | 置換されたトリフェニレン環構造を有する化合物および有機エレクトロルミネッセンス素子 |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2013500895A Division JP5453621B2 (ja) | 2011-02-23 | 2012-02-23 | 置換されたトリフェニレン環構造を有する化合物および有機エレクトロルミネッセンス素子 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2014088399A true JP2014088399A (ja) | 2014-05-15 |
JP5861843B2 JP5861843B2 (ja) | 2016-02-16 |
Family
ID=46720537
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2013500895A Active JP5453621B2 (ja) | 2011-02-23 | 2012-02-23 | 置換されたトリフェニレン環構造を有する化合物および有機エレクトロルミネッセンス素子 |
JP2013256692A Active JP5861843B2 (ja) | 2011-02-23 | 2013-12-12 | 置換されたトリフェニレン環構造を有する化合物および有機エレクトロルミネッセンス素子 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2013500895A Active JP5453621B2 (ja) | 2011-02-23 | 2012-02-23 | 置換されたトリフェニレン環構造を有する化合物および有機エレクトロルミネッセンス素子 |
Country Status (7)
Country | Link |
---|---|
US (3) | US9685612B2 (ja) |
EP (2) | EP2679581B1 (ja) |
JP (2) | JP5453621B2 (ja) |
KR (1) | KR101975067B1 (ja) |
CN (1) | CN103402981A (ja) |
TW (1) | TWI508958B (ja) |
WO (1) | WO2012114745A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10957857B2 (en) | 2016-07-27 | 2021-03-23 | Lg Chem Ltd. | Multicyclic compound and organic light emitting device including the same |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH1144632A (ja) * | 1997-07-28 | 1999-02-16 | Toa Medical Electronics Co Ltd | 粒子計測装置のデータ異常判定方法 |
KR101975067B1 (ko) * | 2011-02-23 | 2019-05-03 | 호도가야 가가쿠 고교 가부시키가이샤 | 치환된 트리페닐렌환 구조를 가지는 화합물 및 유기 일렉트로루미네선스 소자 |
JP6126577B2 (ja) * | 2012-02-28 | 2017-05-10 | 保土谷化学工業株式会社 | 置換基を有するピリジル基とトリフェニレン環構造を有する化合物および有機エレクトロルミネッセンス素子 |
KR20140135525A (ko) | 2013-05-16 | 2014-11-26 | 제일모직주식회사 | 유기 광전자 소자용 발광 재료, 유기 광전자 소자 및 표시 장치 |
KR101618683B1 (ko) * | 2013-05-16 | 2016-05-09 | 제일모직 주식회사 | 유기 화합물, 유기 광전자 소자 및 표시 장치 |
KR101779110B1 (ko) * | 2013-10-11 | 2017-09-18 | 제일모직 주식회사 | 유기 광전자 소자 및 표시 장치 |
JP6354157B2 (ja) * | 2013-12-26 | 2018-07-11 | 日立化成株式会社 | 電荷輸送性材料、該材料を用いたインク組成物、有機エレクトロニクス素子、有機エレクトロルミネセンス素子、表示素子、表示装置及び照明装置 |
KR102255197B1 (ko) | 2014-05-02 | 2021-05-25 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
KR102245164B1 (ko) * | 2014-08-22 | 2021-04-27 | 엘지디스플레이 주식회사 | 유기 발광 소자 및 그의 제조 방법 |
JP7002925B2 (ja) * | 2017-11-13 | 2022-01-20 | 東ソー株式会社 | ジナフトテトラフェニレン化合物を含む有機エレクトロルミネッセンス素子 |
CN109575937A (zh) * | 2018-12-01 | 2019-04-05 | 四川师范大学 | 一种吐昔烯酮-苯并菲盘状液晶化合物及其制备方法 |
CN112409374B (zh) * | 2020-11-20 | 2022-10-14 | 四川师范大学 | 一种刚性核直连的类石墨烯苯并菲盘状液晶的制备方法及介晶性 |
Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007029696A1 (ja) * | 2005-09-05 | 2007-03-15 | Chisso Corporation | 電子輸送材料およびこれを用いた有機電界発光素子 |
JP2007223904A (ja) * | 2005-02-15 | 2007-09-06 | Tosoh Corp | カルド構造を有するπ共役化合物並びにその製造方法及び用途 |
JP2008150365A (ja) * | 2006-11-20 | 2008-07-03 | Chisso Corp | 電子輸送材料およびこれを用いた有機電界発光素子 |
JP2008156266A (ja) * | 2006-12-22 | 2008-07-10 | Chisso Corp | 電子輸送材料およびこれを用いた有機電界発光素子 |
JP2008214307A (ja) * | 2007-03-07 | 2008-09-18 | Chisso Corp | 電子輸送材料およびこれを用いた有機電界発光素子 |
JP2008214306A (ja) * | 2007-03-07 | 2008-09-18 | Chisso Corp | 電子輸送材料およびこれを用いた有機電界発光素子 |
JP2008247895A (ja) * | 2007-03-07 | 2008-10-16 | Chisso Corp | 電子輸送材料およびこれを用いた有機電界発光素子 |
JP2010059158A (ja) * | 2008-09-04 | 2010-03-18 | Gracel Display Inc | 新規な有機電界発光化合物およびこれを用いる有機電界発光素子 |
JP5453621B2 (ja) * | 2011-02-23 | 2014-03-26 | 保土谷化学工業株式会社 | 置換されたトリフェニレン環構造を有する化合物および有機エレクトロルミネッセンス素子 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2734341B2 (ja) | 1993-03-26 | 1998-03-30 | 住友電気工業株式会社 | 有機エレクトロルミネッセンス素子 |
JP3194657B2 (ja) | 1993-11-01 | 2001-07-30 | 松下電器産業株式会社 | 電界発光素子 |
JP3828595B2 (ja) | 1994-02-08 | 2006-10-04 | Tdk株式会社 | 有機el素子 |
KR100691543B1 (ko) | 2002-01-18 | 2007-03-09 | 주식회사 엘지화학 | 새로운 전자 수송용 물질 및 이를 이용한 유기 발광 소자 |
JP4843321B2 (ja) * | 2006-01-31 | 2011-12-21 | Jnc株式会社 | クマリン系化合物、発光素子用材料及び有機電界発光素子 |
-
2012
- 2012-02-23 KR KR1020137024211A patent/KR101975067B1/ko active IP Right Grant
- 2012-02-23 EP EP12749099.3A patent/EP2679581B1/en active Active
- 2012-02-23 TW TW101106043A patent/TWI508958B/zh active
- 2012-02-23 JP JP2013500895A patent/JP5453621B2/ja active Active
- 2012-02-23 US US14/001,041 patent/US9685612B2/en active Active
- 2012-02-23 CN CN2012800104052A patent/CN103402981A/zh active Pending
- 2012-02-23 EP EP17001154.8A patent/EP3255040A1/en not_active Withdrawn
- 2012-02-23 WO PCT/JP2012/001217 patent/WO2012114745A1/ja active Application Filing
-
2013
- 2013-12-12 JP JP2013256692A patent/JP5861843B2/ja active Active
-
2017
- 2017-05-24 US US15/604,088 patent/US10797242B2/en active Active
- 2017-05-24 US US15/604,075 patent/US10026903B2/en active Active
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007223904A (ja) * | 2005-02-15 | 2007-09-06 | Tosoh Corp | カルド構造を有するπ共役化合物並びにその製造方法及び用途 |
WO2007029696A1 (ja) * | 2005-09-05 | 2007-03-15 | Chisso Corporation | 電子輸送材料およびこれを用いた有機電界発光素子 |
JP2008150365A (ja) * | 2006-11-20 | 2008-07-03 | Chisso Corp | 電子輸送材料およびこれを用いた有機電界発光素子 |
JP2008156266A (ja) * | 2006-12-22 | 2008-07-10 | Chisso Corp | 電子輸送材料およびこれを用いた有機電界発光素子 |
JP2008214307A (ja) * | 2007-03-07 | 2008-09-18 | Chisso Corp | 電子輸送材料およびこれを用いた有機電界発光素子 |
JP2008214306A (ja) * | 2007-03-07 | 2008-09-18 | Chisso Corp | 電子輸送材料およびこれを用いた有機電界発光素子 |
JP2008247895A (ja) * | 2007-03-07 | 2008-10-16 | Chisso Corp | 電子輸送材料およびこれを用いた有機電界発光素子 |
JP2010059158A (ja) * | 2008-09-04 | 2010-03-18 | Gracel Display Inc | 新規な有機電界発光化合物およびこれを用いる有機電界発光素子 |
JP5453621B2 (ja) * | 2011-02-23 | 2014-03-26 | 保土谷化学工業株式会社 | 置換されたトリフェニレン環構造を有する化合物および有機エレクトロルミネッセンス素子 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10957857B2 (en) | 2016-07-27 | 2021-03-23 | Lg Chem Ltd. | Multicyclic compound and organic light emitting device including the same |
Also Published As
Publication number | Publication date |
---|---|
EP2679581B1 (en) | 2017-08-09 |
JP5861843B2 (ja) | 2016-02-16 |
JPWO2012114745A1 (ja) | 2014-07-07 |
EP2679581A1 (en) | 2014-01-01 |
KR101975067B1 (ko) | 2019-05-03 |
EP3255040A1 (en) | 2017-12-13 |
US20140034936A1 (en) | 2014-02-06 |
US20170338417A1 (en) | 2017-11-23 |
US10026903B2 (en) | 2018-07-17 |
JP5453621B2 (ja) | 2014-03-26 |
KR20140047592A (ko) | 2014-04-22 |
TWI508958B (zh) | 2015-11-21 |
US20170271595A1 (en) | 2017-09-21 |
EP2679581A4 (en) | 2014-08-13 |
CN103402981A (zh) | 2013-11-20 |
US9685612B2 (en) | 2017-06-20 |
TW201240989A (en) | 2012-10-16 |
WO2012114745A1 (ja) | 2012-08-30 |
US10797242B2 (en) | 2020-10-06 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5861843B2 (ja) | 置換されたトリフェニレン環構造を有する化合物および有機エレクトロルミネッセンス素子 | |
TWI676623B (zh) | 嘧啶衍生物及有機電致發光元件 | |
WO2011105373A1 (ja) | 置換されたピリジル化合物および有機エレクトロルミネッセンス素子 | |
TWI627172B (zh) | 新穎之嘧啶衍生物及有機電致發光元件 | |
JPWO2016117429A1 (ja) | ピリミジン誘導体および有機エレクトロルミネッセンス素子 | |
WO2014024446A1 (ja) | トリフェニレン環構造を有する化合物および有機エレクトロルミネッセンス素子 | |
JPWO2009107651A1 (ja) | 置換されたビピリジル化合物および有機エレクトロルミネッセンス素子 | |
JP5955228B2 (ja) | 置換されたビピリジル基とピリドインドール環構造を有する化合物および有機エレクトロルミネッセンス素子 | |
JP2015071619A (ja) | ベンゾピリドインドール誘導体および有機エレクトロルミネッセンス素子 | |
JP6294866B2 (ja) | 新規なナフトトリアゾール誘導体および有機エレクトロルミネッセンス素子 | |
WO2014024447A1 (ja) | トリフェニレン環構造を有する化合物および有機エレクトロルミネッセンス素子 | |
JP5870346B2 (ja) | 置換されたオルトターフェニル構造を有する化合物および有機エレクトロルミネッセンス素子 | |
JP6126577B2 (ja) | 置換基を有するピリジル基とトリフェニレン環構造を有する化合物および有機エレクトロルミネッセンス素子 | |
JP6479770B2 (ja) | キノリノトリアゾール誘導体および有機エレクトロルミネッセンス素子 | |
JP5499227B1 (ja) | トリフェニルシリルピリジル基とカルバゾール環構造を有する化合物および有機エレクトロルミネッセンス素子 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20150203 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20150203 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20150903 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20150908 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20151102 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20151201 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20151208 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5861843 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
S531 | Written request for registration of change of domicile |
Free format text: JAPANESE INTERMEDIATE CODE: R313531 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
S531 | Written request for registration of change of domicile |
Free format text: JAPANESE INTERMEDIATE CODE: R313531 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |