JP2014508778A - ピリジルカルベンリン光発光体 - Google Patents
ピリジルカルベンリン光発光体 Download PDFInfo
- Publication number
- JP2014508778A JP2014508778A JP2013557759A JP2013557759A JP2014508778A JP 2014508778 A JP2014508778 A JP 2014508778A JP 2013557759 A JP2013557759 A JP 2013557759A JP 2013557759 A JP2013557759 A JP 2013557759A JP 2014508778 A JP2014508778 A JP 2014508778A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- mmol
- group
- ligand
- added
- 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
- 239000000463 material Substances 0.000 title description 77
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 114
- 239000003446 ligand Substances 0.000 claims abstract description 109
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims abstract description 44
- 239000010410 layer Substances 0.000 claims description 88
- 229910052757 nitrogen Inorganic materials 0.000 claims description 79
- -1 amino, silyl Chemical group 0.000 claims description 45
- 239000012044 organic layer Substances 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 229910052751 metal Inorganic materials 0.000 claims description 27
- 239000002184 metal Substances 0.000 claims description 27
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- 125000004104 aryloxy group Chemical group 0.000 claims description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 125000003342 alkenyl group Chemical group 0.000 claims description 21
- 125000000304 alkynyl group Chemical group 0.000 claims description 21
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 20
- 125000002252 acyl group Chemical group 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 20
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 20
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 20
- 229910052805 deuterium Inorganic materials 0.000 claims description 20
- 150000002148 esters Chemical class 0.000 claims description 20
- 150000004820 halides Chemical class 0.000 claims description 20
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 20
- 150000002431 hydrogen Chemical class 0.000 claims description 20
- 150000002527 isonitriles Chemical class 0.000 claims description 20
- 150000002825 nitriles Chemical class 0.000 claims description 20
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims description 20
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 20
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 20
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 20
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 238000006467 substitution reaction Methods 0.000 claims description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- 239000002019 doping agent Substances 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 150000004696 coordination complex Chemical group 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 229910052741 iridium Inorganic materials 0.000 claims description 7
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 6
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 6
- 229910052697 platinum Inorganic materials 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000001769 aryl amino group Chemical group 0.000 claims description 3
- 125000003636 chemical group Chemical group 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract description 83
- 125000002883 imidazolyl group Chemical group 0.000 abstract description 19
- 150000002902 organometallic compounds Chemical class 0.000 abstract description 16
- 230000005281 excited state Effects 0.000 abstract description 10
- 238000005424 photoluminescence Methods 0.000 abstract description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 7
- 238000000295 emission spectrum Methods 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 245
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 165
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 149
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 131
- 230000015572 biosynthetic process Effects 0.000 description 94
- 238000003786 synthesis reaction Methods 0.000 description 94
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 77
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 71
- 239000011541 reaction mixture Substances 0.000 description 60
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 57
- 235000019439 ethyl acetate Nutrition 0.000 description 57
- 239000000203 mixture Substances 0.000 description 53
- 239000007787 solid Substances 0.000 description 52
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 44
- 239000000243 solution Substances 0.000 description 38
- 238000006243 chemical reaction Methods 0.000 description 35
- 239000002904 solvent Substances 0.000 description 34
- 238000004440 column chromatography Methods 0.000 description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 238000010992 reflux Methods 0.000 description 27
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 23
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
- 239000000706 filtrate Substances 0.000 description 21
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 15
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 15
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 238000001914 filtration Methods 0.000 description 14
- 235000019253 formic acid Nutrition 0.000 description 14
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 14
- 238000004770 highest occupied molecular orbital Methods 0.000 description 13
- 230000032258 transport Effects 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 230000000903 blocking effect Effects 0.000 description 12
- 239000007924 injection Substances 0.000 description 12
- 238000002347 injection Methods 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- 229910001923 silver oxide Inorganic materials 0.000 description 12
- 150000003384 small molecules Chemical class 0.000 description 12
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 11
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
- 235000019341 magnesium sulphate Nutrition 0.000 description 11
- 239000002243 precursor Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 9
- 230000005525 hole transport Effects 0.000 description 9
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 9
- VFWRGKJLLYDFBY-UHFFFAOYSA-N silver;hydrate Chemical compound O.[Ag].[Ag] VFWRGKJLLYDFBY-UHFFFAOYSA-N 0.000 description 9
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 8
- UUOLETYDNTVQDY-UHFFFAOYSA-N 2-chloro-3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1Cl UUOLETYDNTVQDY-UHFFFAOYSA-N 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 238000000151 deposition Methods 0.000 description 7
- 238000005984 hydrogenation reaction Methods 0.000 description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 6
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 6
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 125000005331 diazinyl group Chemical group N1=NC(=CC=C1)* 0.000 description 6
- 239000011368 organic material Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 6
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 239000000412 dendrimer Substances 0.000 description 5
- 229920000736 dendritic polymer Polymers 0.000 description 5
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 5
- 239000000539 dimer Substances 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 239000011888 foil Substances 0.000 description 5
- 150000002460 imidazoles Chemical class 0.000 description 5
- 150000002503 iridium Chemical class 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 230000005693 optoelectronics Effects 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 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 4
- 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 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- OLQLKEGDKARDNO-UHFFFAOYSA-N 2-n-phenylpyridine-2,3-diamine Chemical compound NC1=CC=CN=C1NC1=CC=CC=C1 OLQLKEGDKARDNO-UHFFFAOYSA-N 0.000 description 4
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 4
- 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 4
- DJEFHNHKOJTDHM-UHFFFAOYSA-N 4-phenylpyridine-2,3-diamine Chemical compound NC1=NC=CC(C=2C=CC=CC=2)=C1N DJEFHNHKOJTDHM-UHFFFAOYSA-N 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-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
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 4
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 4
- 229940125810 compound 20 Drugs 0.000 description 4
- 229940125846 compound 25 Drugs 0.000 description 4
- 230000021615 conjugation Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 238000000859 sublimation Methods 0.000 description 4
- 230000008022 sublimation Effects 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 3
- MLCNOCRGSBCAGH-UHFFFAOYSA-N 2,3-dichloropyrazine Chemical compound ClC1=NC=CN=C1Cl MLCNOCRGSBCAGH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 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 3
- WCDCAXVNBOLWNO-UHFFFAOYSA-N 2-fluoro-3-iodopyridine Chemical compound FC1=NC=CC=C1I WCDCAXVNBOLWNO-UHFFFAOYSA-N 0.000 description 3
- CLVOWQGBRGLTBC-UHFFFAOYSA-N 3-chloro-n-methylpyrazin-2-amine Chemical compound CNC1=NC=CN=C1Cl CLVOWQGBRGLTBC-UHFFFAOYSA-N 0.000 description 3
- QEORHYXDOJMCEV-UHFFFAOYSA-N 3-chloro-n-phenylpyrazin-2-amine Chemical compound ClC1=NC=CN=C1NC1=CC=CC=C1 QEORHYXDOJMCEV-UHFFFAOYSA-N 0.000 description 3
- VHCWENVIQSXOQV-UHFFFAOYSA-N 3-chloro-n-propan-2-ylpyrazin-2-amine Chemical compound CC(C)NC1=NC=CN=C1Cl VHCWENVIQSXOQV-UHFFFAOYSA-N 0.000 description 3
- MVFOZPUJBFFGFO-UHFFFAOYSA-N 3-iodo-n-methylpyridin-2-amine Chemical compound CNC1=NC=CC=C1I MVFOZPUJBFFGFO-UHFFFAOYSA-N 0.000 description 3
- PCCSYAWZVABITQ-UHFFFAOYSA-N 3-nitro-n-phenylpyridin-2-amine Chemical compound [O-][N+](=O)C1=CC=CN=C1NC1=CC=CC=C1 PCCSYAWZVABITQ-UHFFFAOYSA-N 0.000 description 3
- NQBCVEFNJWVJMX-UHFFFAOYSA-M 3-phenyl-1-propan-2-ylimidazo[4,5-b]pyridin-1-ium;chloride Chemical compound [Cl-].C12=NC=CC=C2[N+](C(C)C)=CN1C1=CC=CC=C1 NQBCVEFNJWVJMX-UHFFFAOYSA-M 0.000 description 3
- IODANHRTJVJLSC-UHFFFAOYSA-N 5-(3-methylphenyl)pyrazine-2,3-diamine Chemical compound C1(=CC(=CC=C1)C=1N=C(C(=NC=1)N)N)C IODANHRTJVJLSC-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 229940126657 Compound 17 Drugs 0.000 description 3
- 229940126062 Compound A Drugs 0.000 description 3
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 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 3
- 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 3
- 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 3
- 230000008901 benefit Effects 0.000 description 3
- 238000007664 blowing Methods 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 229940126543 compound 14 Drugs 0.000 description 3
- 229940125758 compound 15 Drugs 0.000 description 3
- 229940126142 compound 16 Drugs 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 229940126086 compound 21 Drugs 0.000 description 3
- 229940126208 compound 22 Drugs 0.000 description 3
- 229940125961 compound 24 Drugs 0.000 description 3
- 229940127204 compound 29 Drugs 0.000 description 3
- 229940125877 compound 31 Drugs 0.000 description 3
- 239000013058 crude material Substances 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical class C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- CCCXKBLCIOUOGA-UHFFFAOYSA-N n-(1,3-benzodioxol-5-yl)-3-nitropyridin-2-amine Chemical compound [O-][N+](=O)C1=CC=CN=C1NC1=CC=C(OCO2)C2=C1 CCCXKBLCIOUOGA-UHFFFAOYSA-N 0.000 description 3
- 239000011241 protective layer Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000002207 thermal evaporation Methods 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 3
- 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 2
- 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 2
- 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 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 2
- 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 2
- BNRDGHFESOHOBF-UHFFFAOYSA-N 1-benzoselenophene Chemical compound C1=CC=C2[se]C=CC2=C1 BNRDGHFESOHOBF-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 2
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 2
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 2
- HXPMAXVNRZGKOB-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-1H-pyridine-2,3-diamine Chemical compound O1COC2=C1C=CC(=C2)C2(NC=CC=C2N)N HXPMAXVNRZGKOB-UHFFFAOYSA-N 0.000 description 2
- YJRUTQNPPWLFRM-UHFFFAOYSA-N 2-n-(3-methylphenyl)-3-n-propan-2-ylpyrazine-2,3-diamine Chemical compound CC(C)NC1=NC=CN=C1NC1=CC=CC(C)=C1 YJRUTQNPPWLFRM-UHFFFAOYSA-N 0.000 description 2
- ZFQMBPLMVOTTFG-UHFFFAOYSA-N 2-n-ethyl-3-n-phenylpyridine-2,3-diamine Chemical compound CCNC1=NC=CC=C1NC1=CC=CC=C1 ZFQMBPLMVOTTFG-UHFFFAOYSA-N 0.000 description 2
- UQXRQVGWVGDXMS-UHFFFAOYSA-N 2-n-ethylpyridine-2,3-diamine Chemical compound CCNC1=NC=CC=C1N UQXRQVGWVGDXMS-UHFFFAOYSA-N 0.000 description 2
- YLNGBXBRRZCMCW-UHFFFAOYSA-N 2-n-methyl-3-n-[3-(n-phenylanilino)phenyl]pyridine-2,3-diamine Chemical compound CNC1=NC=CC=C1NC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 YLNGBXBRRZCMCW-UHFFFAOYSA-N 0.000 description 2
- UEPLCTHKRSEKLE-UHFFFAOYSA-N 2-n-methyl-3-n-phenylpyrazine-2,3-diamine Chemical compound CNC1=NC=CN=C1NC1=CC=CC=C1 UEPLCTHKRSEKLE-UHFFFAOYSA-N 0.000 description 2
- CTPZYIKPTSKZFD-UHFFFAOYSA-N 2-n-phenyl-3-n-propan-2-ylpyridine-2,3-diamine Chemical compound CC(C)NC1=CC=CN=C1NC1=CC=CC=C1 CTPZYIKPTSKZFD-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- OLGGLCIDAMICTA-UHFFFAOYSA-N 2-pyridin-2-yl-1h-indole Chemical compound N1C2=CC=CC=C2C=C1C1=CC=CC=N1 OLGGLCIDAMICTA-UHFFFAOYSA-N 0.000 description 2
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 2
- ZFRYGQMBTZFBHB-UHFFFAOYSA-M 3-(1,3-benzodioxol-5-yl)-1-propan-2-ylimidazo[4,5-b]pyridin-1-ium;chloride Chemical compound [Cl-].C12=NC=CC=C2[N+](C(C)C)=CN1C1=CC=C(OCO2)C2=C1 ZFRYGQMBTZFBHB-UHFFFAOYSA-M 0.000 description 2
- BVSSLWSVVVVYMO-UHFFFAOYSA-N 3-n-methyl-2-n-phenylpyridine-2,3-diamine Chemical compound CNC1=CC=CN=C1NC1=CC=CC=C1 BVSSLWSVVVVYMO-UHFFFAOYSA-N 0.000 description 2
- RPOZPZAEUYGBDA-UHFFFAOYSA-N 3-nitro-n,n-diphenylaniline Chemical compound [O-][N+](=O)C1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 RPOZPZAEUYGBDA-UHFFFAOYSA-N 0.000 description 2
- WIKRPGQJJRWTJB-UHFFFAOYSA-N 3-nitro-n-(3-phenylphenyl)pyridin-2-amine Chemical compound [O-][N+](=O)C1=CC=CN=C1NC1=CC=CC(C=2C=CC=CC=2)=C1 WIKRPGQJJRWTJB-UHFFFAOYSA-N 0.000 description 2
- MUNOBADFTHUUFG-UHFFFAOYSA-N 3-phenylaniline Chemical compound NC1=CC=CC(C=2C=CC=CC=2)=C1 MUNOBADFTHUUFG-UHFFFAOYSA-N 0.000 description 2
- BWCDLEQTELFBAW-UHFFFAOYSA-N 3h-dioxazole Chemical compound N1OOC=C1 BWCDLEQTELFBAW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- DEUFNSJMHLSSES-UHFFFAOYSA-N 4-(3-methylphenyl)pyridine-2,3-diamine Chemical compound CC1=CC=CC(C=2C(=C(N)N=CC=2)N)=C1 DEUFNSJMHLSSES-UHFFFAOYSA-N 0.000 description 2
- DEZNHSJVTMBPNL-UHFFFAOYSA-N 4-azidodibenzofuran Chemical compound C12=CC=CC=C2OC2=C1C=CC=C2N=[N+]=[N-] DEZNHSJVTMBPNL-UHFFFAOYSA-N 0.000 description 2
- MEMYDMQBHRNQCS-UHFFFAOYSA-N 4-dibenzofuran-4-ylpyridine-2,3-diamine Chemical compound NC1=NC=CC(C=2C=3OC4=CC=CC=C4C=3C=CC=2)=C1N MEMYDMQBHRNQCS-UHFFFAOYSA-N 0.000 description 2
- FOWPHNVIKXNDBS-UHFFFAOYSA-N 5-methyl-2-n-(3-methylphenyl)pyridine-2,3-diamine Chemical compound CC1=CC=CC(NC=2C(=CC(C)=CN=2)N)=C1 FOWPHNVIKXNDBS-UHFFFAOYSA-N 0.000 description 2
- ADXFGWMAALDJSF-UHFFFAOYSA-N 5-methyl-n-(3-methylphenyl)-3-nitropyridin-2-amine Chemical compound CC1=CC=CC(NC=2C(=CC(C)=CN=2)[N+]([O-])=O)=C1 ADXFGWMAALDJSF-UHFFFAOYSA-N 0.000 description 2
- XYEVAHUAWWCGGQ-UHFFFAOYSA-N 6-chloro-3-nitro-n-phenylpyridin-2-amine Chemical compound [O-][N+](=O)C1=CC=C(Cl)N=C1NC1=CC=CC=C1 XYEVAHUAWWCGGQ-UHFFFAOYSA-N 0.000 description 2
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- KMNAHTYMPWDZEY-UHFFFAOYSA-N C12=CC=CN=C2[N+](CC)(Cl)[CH-]N1C1=CC=CC=C1 Chemical compound C12=CC=CN=C2[N+](CC)(Cl)[CH-]N1C1=CC=CC=C1 KMNAHTYMPWDZEY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 2
- QZLAKPGRUFFNRD-UHFFFAOYSA-N [1]benzoselenolo[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3[se]C2=C1 QZLAKPGRUFFNRD-UHFFFAOYSA-N 0.000 description 2
- WIUZHVZUGQDRHZ-UHFFFAOYSA-N [1]benzothiolo[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3SC2=C1 WIUZHVZUGQDRHZ-UHFFFAOYSA-N 0.000 description 2
- UHMKIFCZHWQCTK-UHFFFAOYSA-N [8-(8-diphenylphosphanylnaphthalen-1-yl)naphthalen-1-yl]-diphenylphosphane Chemical compound C1=CC=CC=C1P(C=1C2=C(C=3C4=C(P(C=5C=CC=CC=5)C=5C=CC=CC=5)C=CC=C4C=CC=3)C=CC=C2C=CC=1)C1=CC=CC=C1 UHMKIFCZHWQCTK-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 229940125797 compound 12 Drugs 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- QKBTTXJHJNXCOQ-UHFFFAOYSA-N dibenzofuran-4-amine Chemical compound O1C2=CC=CC=C2C2=C1C(N)=CC=C2 QKBTTXJHJNXCOQ-UHFFFAOYSA-N 0.000 description 2
- DHFABSXGNHDNCO-UHFFFAOYSA-N dibenzoselenophene Chemical compound C1=CC=C2C3=CC=CC=C3[se]C2=C1 DHFABSXGNHDNCO-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 2
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 2
- 229960005544 indolocarbazole Drugs 0.000 description 2
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 2
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- XQYXDWHVXPNULZ-UHFFFAOYSA-N n-(3-methylphenyl)-3-nitropyridin-2-amine Chemical compound CC1=CC=CC(NC=2C(=CC=CN=2)[N+]([O-])=O)=C1 XQYXDWHVXPNULZ-UHFFFAOYSA-N 0.000 description 2
- YYRIVURSZLOFLJ-UHFFFAOYSA-N n-dibenzofuran-4-yl-3-nitropyridin-2-amine Chemical compound [O-][N+](=O)C1=CC=CN=C1NC1=CC=CC2=C1OC1=CC=CC=C21 YYRIVURSZLOFLJ-UHFFFAOYSA-N 0.000 description 2
- DDBQQNCEHLMYGB-UHFFFAOYSA-N n-ethyl-3-nitropyridin-2-amine Chemical compound CCNC1=NC=CC=C1[N+]([O-])=O DDBQQNCEHLMYGB-UHFFFAOYSA-N 0.000 description 2
- SILGRKFIVIVPKA-UHFFFAOYSA-N n-methyl-3-nitropyridin-2-amine Chemical compound CNC1=NC=CC=C1[N+]([O-])=O SILGRKFIVIVPKA-UHFFFAOYSA-N 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
- AZHVQJLDOFKHPZ-UHFFFAOYSA-N oxathiazine Chemical compound O1SN=CC=C1 AZHVQJLDOFKHPZ-UHFFFAOYSA-N 0.000 description 2
- CQDAMYNQINDRQC-UHFFFAOYSA-N oxatriazole Chemical compound C1=NN=NO1 CQDAMYNQINDRQC-UHFFFAOYSA-N 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 238000000059 patterning Methods 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 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 2
- XDJOIMJURHQYDW-UHFFFAOYSA-N phenalene Chemical compound C1=CC(CC=C2)=C3C2=CC=CC3=C1 XDJOIMJURHQYDW-UHFFFAOYSA-N 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 2
- CRTBNOWPBHJICM-UHFFFAOYSA-N pyrazine Chemical compound C1=CN=CC=N1.C1=CN=CC=N1 CRTBNOWPBHJICM-UHFFFAOYSA-N 0.000 description 2
- ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical compound NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 2
- YMXFJTUQQVLJEN-UHFFFAOYSA-N pyrimidine Chemical compound C1=CN=CN=C1.C1=CN=CN=C1 YMXFJTUQQVLJEN-UHFFFAOYSA-N 0.000 description 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 2
- 238000010129 solution processing Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 230000001052 transient effect Effects 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- 125000005580 triphenylene group Chemical group 0.000 description 2
- XGNXYCFREOZBOL-UHFFFAOYSA-N 1,3-benzodioxol-5-amine Chemical compound NC1=CC=C2OCOC2=C1 XGNXYCFREOZBOL-UHFFFAOYSA-N 0.000 description 1
- IOJZNPWLWBKJCK-UHFFFAOYSA-M 1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-methylimidazo[4,5-b]pyridin-3-ium;chloride Chemical compound [Cl-].C12=CC=CN=C2[N+](C)=CN1C1=CC=C(OCCO2)C2=C1 IOJZNPWLWBKJCK-UHFFFAOYSA-M 0.000 description 1
- CBYAZOKPJYBCHE-UHFFFAOYSA-N 1-iodo-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(I)=C1 CBYAZOKPJYBCHE-UHFFFAOYSA-N 0.000 description 1
- FYRPEHRWMVMHQM-UHFFFAOYSA-N 1-nitro-3-phenylbenzene Chemical group [O-][N+](=O)C1=CC=CC(C=2C=CC=CC=2)=C1 FYRPEHRWMVMHQM-UHFFFAOYSA-N 0.000 description 1
- SEULWJSKCVACTH-UHFFFAOYSA-N 1-phenylimidazole Chemical compound C1=NC=CN1C1=CC=CC=C1 SEULWJSKCVACTH-UHFFFAOYSA-N 0.000 description 1
- SHCWQWRTKPNTEM-UHFFFAOYSA-N 2,6-dichloro-3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=C(Cl)N=C1Cl SHCWQWRTKPNTEM-UHFFFAOYSA-N 0.000 description 1
- PCDAZIGBFBVXCV-UHFFFAOYSA-N 2-(3-phenylphenyl)-1H-pyridine-2,3-diamine Chemical compound C1(=CC(=CC=C1)C1(NC=CC=C1N)N)C1=CC=CC=C1 PCDAZIGBFBVXCV-UHFFFAOYSA-N 0.000 description 1
- LUAJUWOJEFFNFE-UHFFFAOYSA-N 2-chloro-5-methyl-3-nitropyridine Chemical compound CC1=CN=C(Cl)C([N+]([O-])=O)=C1 LUAJUWOJEFFNFE-UHFFFAOYSA-N 0.000 description 1
- TYCCWRAOMPWADQ-UHFFFAOYSA-N 2-dibenzofuran-4-yl-3-N-methyl-1H-pyridine-2,3-diamine Chemical compound C1=CC=C(C=2OC3=C(C=21)C=CC=C3)C1(NC=CC=C1NC)N TYCCWRAOMPWADQ-UHFFFAOYSA-N 0.000 description 1
- MTAODLNXWYIKSO-UHFFFAOYSA-N 2-fluoropyridine Chemical compound FC1=CC=CC=N1 MTAODLNXWYIKSO-UHFFFAOYSA-N 0.000 description 1
- CPGACJMMQLDUAD-UHFFFAOYSA-N 2-n-(1,3-benzodioxol-5-yl)-3-n-propan-2-ylpyridine-2,3-diamine Chemical compound CC(C)NC1=CC=CN=C1NC1=CC=C(OCO2)C2=C1 CPGACJMMQLDUAD-UHFFFAOYSA-N 0.000 description 1
- OWROLTVNXRCEDW-UHFFFAOYSA-N 2-n-(3-methylphenyl)pyridine-2,3-diamine Chemical compound CC1=CC=CC(NC=2C(=CC=CN=2)N)=C1 OWROLTVNXRCEDW-UHFFFAOYSA-N 0.000 description 1
- ZBWDHVAPJVHHCZ-UHFFFAOYSA-N 2-n-methyl-3-n-(3-methylphenyl)pyrazine-2,3-diamine Chemical compound CNC1=NC=CN=C1NC1=CC=CC(C)=C1 ZBWDHVAPJVHHCZ-UHFFFAOYSA-N 0.000 description 1
- WSAKJYKPYLLCPZ-UHFFFAOYSA-N 2-n-methyl-3-n-phenylpyridine-2,3-diamine Chemical compound CNC1=NC=CC=C1NC1=CC=CC=C1 WSAKJYKPYLLCPZ-UHFFFAOYSA-N 0.000 description 1
- COANMWJRJDRXNS-UHFFFAOYSA-N 2-n-methylpyridine-2,3-diamine Chemical compound CNC1=NC=CC=C1N COANMWJRJDRXNS-UHFFFAOYSA-N 0.000 description 1
- 150000005360 2-phenylpyridines Chemical class 0.000 description 1
- QMEQBOSUJUOXMX-UHFFFAOYSA-N 2h-oxadiazine Chemical compound N1OC=CC=N1 QMEQBOSUJUOXMX-UHFFFAOYSA-N 0.000 description 1
- JEALZUTXUILDRK-UHFFFAOYSA-N 3-(3-methylimidazo[4,5-b]pyridin-3-ium-1-yl)-n,n-diphenylaniline Chemical compound C12=CC=CN=C2[N+](C)=CN1C(C=1)=CC=CC=1N(C=1C=CC=CC=1)C1=CC=CC=C1 JEALZUTXUILDRK-UHFFFAOYSA-N 0.000 description 1
- XRTPDOGLOZNFAT-UHFFFAOYSA-M 3-(3-methylimidazo[4,5-b]pyridin-3-ium-1-yl)-n,n-diphenylaniline;chloride Chemical compound [Cl-].C12=CC=CN=C2[N+](C)=CN1C(C=1)=CC=CC=1N(C=1C=CC=CC=1)C1=CC=CC=C1 XRTPDOGLOZNFAT-UHFFFAOYSA-M 0.000 description 1
- MCXOPHLCNMBLPI-UHFFFAOYSA-N 3-N-methyl-2-(3-phenylphenyl)-1H-pyridine-2,3-diamine Chemical compound C1(=CC(=CC=C1)C1(NC=CC=C1NC)N)C1=CC=CC=C1 MCXOPHLCNMBLPI-UHFFFAOYSA-N 0.000 description 1
- RSPHWOYYWACCJK-UHFFFAOYSA-N 3-n,3-n-diphenylbenzene-1,3-diamine Chemical compound NC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 RSPHWOYYWACCJK-UHFFFAOYSA-N 0.000 description 1
- JSQSJAKLSSCKND-UHFFFAOYSA-N 3-n-methyl-2-n-(3-methylphenyl)pyridine-2,3-diamine Chemical compound CNC1=CC=CN=C1NC1=CC=CC(C)=C1 JSQSJAKLSSCKND-UHFFFAOYSA-N 0.000 description 1
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical group C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 1
- FJNSSRRFFJIVJQ-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)pyridine-2,3-diamine Chemical compound NC1=NC=CC(C=2C=C3OCOC3=CC=2)=C1N FJNSSRRFFJIVJQ-UHFFFAOYSA-N 0.000 description 1
- OQWNNAWQMWLBGL-UHFFFAOYSA-N 4-ethylpyridine-2,3-diamine Chemical compound CCC1=CC=NC(N)=C1N OQWNNAWQMWLBGL-UHFFFAOYSA-N 0.000 description 1
- ADLVDYMTBOSDFE-UHFFFAOYSA-N 5-chloro-6-nitroisoindole-1,3-dione Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC2=C1C(=O)NC2=O ADLVDYMTBOSDFE-UHFFFAOYSA-N 0.000 description 1
- ZIIKKNNQZLDMFD-UHFFFAOYSA-N 5-phenylpyrazine-2,3-diamine Chemical compound N1=C(N)C(N)=NC=C1C1=CC=CC=C1 ZIIKKNNQZLDMFD-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- XOCKBANQJSRNCA-UHFFFAOYSA-N C12=CC=CN=C2[N+](C(C)C)(Cl)[CH-]N1C1=CC=CC=C1 Chemical compound C12=CC=CN=C2[N+](C(C)C)(Cl)[CH-]N1C1=CC=CC=C1 XOCKBANQJSRNCA-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
- 235000019502 Orange oil Nutrition 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- FBVBNCGJVKIEHH-UHFFFAOYSA-N [1]benzofuro[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3OC2=C1 FBVBNCGJVKIEHH-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000007080 aromatic substitution reaction Methods 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 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
- DYEGEQTYEIHCSO-UHFFFAOYSA-N n-diazo-4-dodecylbenzenesulfonamide Chemical compound CCCCCCCCCCCCC1=CC=C(S(=O)(=O)N=[N+]=[N-])C=C1 DYEGEQTYEIHCSO-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 229910052762 osmium Inorganic materials 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
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 150000004033 porphyrin derivatives Chemical class 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 230000008054 signal transmission Effects 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- RMNIZOOYFMNEJJ-UHFFFAOYSA-K tripotassium;phosphate;hydrate Chemical compound O.[K+].[K+].[K+].[O-]P([O-])([O-])=O RMNIZOOYFMNEJJ-UHFFFAOYSA-K 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
- UGOMMVLRQDMAQQ-UHFFFAOYSA-N xphos Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 UGOMMVLRQDMAQQ-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- 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
- H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
-
- 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
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/30—Devices specially adapted for multicolour light emission
- H10K59/35—Devices specially adapted for multicolour light emission comprising red-green-blue [RGB] subpixels
-
- 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
-
- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Manufacturing & Machinery (AREA)
- Electroluminescent Light Sources (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
有機発光デバイス中の特定の層に有用として本明細書において記述されている材料は、デバイス中に存在する多種多様な他の材料と組み合わせて使用され得る。例えば、本明細書において開示されている発光性ドーパントは、多種多様なホスト、輸送層、ブロッキング層、注入層、電極、及び存在し得る他の層と併せて使用され得る。以下で記述又は参照される材料は、本明細書において開示されている化合物と組み合わせて有用となり得る材料の非限定的な例であり、当業者であれば、組み合わせて有用となり得る他の材料を特定するための文献を容易に閲覧することができる。
HIL/HTL:
ホスト:
HBL:
ETL:
実施例1. 化合物1及び化合物2の合成
デバイス実施例
110 基板
115 アノード
120 正孔注入層
125 正孔輸送層
130 電子ブロッキング層
135 発光層
140 正孔ブロッキング層
145 電子輸送層
150 電子注入層
155 保護層
160 カソード
162 第一の導電層
164 第二の導電層
200 反転させたOLED、デバイス
210 基板
215 カソード
220 発光層
225 正孔輸送層
230 アノード
Claims (26)
- 下記の式を有する配位子Lを含むことを特徴とする化合物。
R2及びRAは、モノ、ジ、トリ又はテトラ置換を表し;
R1、R2及びRAは、それぞれ独立して、水素、重水素、ハライド、アルキル、シクロアルキル、ヘテロアルキル、アリールアルキル、アルコキシ、アリールオキシ、アミノ、シリル、アルケニル、シクロアルケニル、ヘテロアルケニル、アルキニル、アリール、ヘテロアリール、アシル、カルボニル、カルボン酸、エステル、ニトリル、イソニトリル、スルファニル、スルフィニル、スルフォニル、ホスフィノ及びこれらの組み合わせからなる群から選択され;
R2及びRAの2つの隣接する置換基は、結合して縮合環を形成していてもよく;
X1、X2、X3及びX4は、それぞれ独立して、C及びNからなる群から選択され;
X1、X2、X3及びX4のうちの少なくとも2つは、Nであり;
前記配位子Lは、40超の原子番号を有する金属Mに配位しており;
二座配位子は、他の配位子と結合して、三座、四座、五座又は六座配位子を形成していてもよい。) - Aがベンゼンである請求項1に記載の化合物。
- 金属MがIr又はPtである請求項1に記載の化合物。
- 金属MがIrである請求項1に記載の化合物。
- R1がアルキル又はシクロアルキルである請求項1に記載の化合物。
- R1がアリールである請求項1に記載の化合物。
- RAが0未満のハメットシグマ定数を有する電子供与性基である請求項1に記載の化合物。
- RAがアルキル、アリールアミノ、アルキルアミノ、アリールオキシル、及びアルキルオキシルからなる群から選択される請求項7に記載の化合物。
- 配位子Lが下記からなる群から選択される請求項1に記載の化合物。
R3は、水素、重水素、ハライド、アルキル、シクロアルキル、ヘテロアルキル、アリールアルキル、アルコキシ、アリールオキシ、アミノ、シリル、アルケニル、シクロアルケニル、ヘテロアルケニル、アルキニル、アリール、ヘテロアリール、アシル、カルボニル、カルボン酸、エステル、ニトリル、イソニトリル、スルファニル、スルフィニル、スルフォニル、ホスフィノ及びこれらの組み合わせからなる群から選択され;
R3の2つの隣接する置換基は、結合して縮合環を形成していてもよい。) - 化合物がホモレプティックである請求項1に記載の化合物。
- 化合物がヘテロレプティックである請求項1に記載の化合物。
- 化合物が下記からなる群から選択される式を有する請求項1に記載の化合物。
mは、1、2、又は3である。) - mが3である請求項12に記載の化合物。
- L’がモノアニオン性二座配位子である請求項12に記載の化合物。
- L’が下記からなる群から選択される請求項12に記載の化合物。
Ra、Rb、及びRcは、独立して、水素、重水素、ハライド、アルキル、シクロアルキル、ヘテロアルキル、アリールアルキル、アルコキシ、アリールオキシ、アミノ、シリル、アルケニル、シクロアルケニル、ヘテロアルケニル、アルキニル、アリール、ヘテロアリール、アシル、カルボニル、カルボン酸、エステル、ニトリル、イソニトリル、スルファニル、スルフィニル、スルフォニル、ホスフィノ及びこれらの組み合わせからなる群から選択され;
Ra、Rb、及びRcの2つの隣接する置換基は、結合して縮合環を形成していてもよい。) - 化合物が下記からなる群から選択される請求項1に記載の化合物。
- 下記からなる群から選択されることを特徴とする化合物。
- 有機発光デバイスを含む第1のデバイスであって、アノードと、カソードと、前記アノードと前記カソードとの間に配置された有機層とを更に含み、前記有機層は、下記の式の配位子Lを含む化合物を更に含むことを特徴とする第1のデバイス。
R2及びRAは、モノ、ジ、トリ又はテトラ置換を表し;
R1、R2及びRAは、それぞれ独立して、水素、重水素、ハライド、アルキル、シクロアルキル、ヘテロアルキル、アリールアルキル、アルコキシ、アリールオキシ、アミノ、シリル、アルケニル、シクロアルケニル、ヘテロアルケニル、アルキニル、アリール、ヘテロアリール、アシル、カルボニル、カルボン酸、エステル、ニトリル、イソニトリル、スルファニル、スルフィニル、スルフォニル、ホスフィノ及びこれらの組み合わせからなる群から選択され;
R2及びRAの2つの隣接する置換基は、結合して縮合環を形成していてもよく;
X1、X2、X3及びX4は、それぞれ独立して、C及びNからなる群から選択され;
X1、X2、X3及びX4のうちの少なくとも2つは、Nであり;
前記配位子Lは、40超の原子番号を有する金属Mに配位しており;
二座配位子は、他の配位子と結合して、三座、四座、五座又は六座配位子を形成していてもよい。) - 有機層が発光層であり、配位子Lを含む化合物が発光性ドーパントである請求項18に記載の第1のデバイス。
- 有機層がホストを更に含む請求項19に記載の第1のデバイス。
- ホストが下記からなる群から選択される化学基の少なくとも1つを含む請求項20に記載の第1のデバイス。
kは、0から20の整数であり;
X1、X2、X3、X4、X5、X6、X7及びX8は、それぞれ独立して、CH及びNからなる群から選択される。) - ホストが金属錯体である請求項20に記載の第1のデバイス。
- ホストが金属カルベン錯体である請求項20に記載の第1のデバイス。
- 有機発光デバイスである請求項18に記載の第1のデバイス。
- 消費者製品である請求項18に記載の第1のデバイス。
- 有機発光デバイスを含む第1のデバイスであって、アノードと、カソードと、前記アノードと前記カソードとの間に配置された有機層とを更に含み、前記有機層は、下記のからなる群から選択させる化合物を更に含むことを特徴とする第1のデバイス。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US13/043,180 | 2011-03-08 | ||
US13/043,180 US8883322B2 (en) | 2011-03-08 | 2011-03-08 | Pyridyl carbene phosphorescent emitters |
PCT/US2012/027044 WO2012121936A2 (en) | 2011-03-08 | 2012-02-28 | Pyridyl carbene phosphorescent emitters |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2016143865A Division JP6316351B2 (ja) | 2011-03-08 | 2016-07-22 | ピリジルカルベンリン光発光体 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2014508778A true JP2014508778A (ja) | 2014-04-10 |
JP6073819B2 JP6073819B2 (ja) | 2017-02-01 |
Family
ID=45814688
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2013557759A Active JP6073819B2 (ja) | 2011-03-08 | 2012-02-28 | ピリジルカルベンリン光発光体 |
JP2016143865A Active JP6316351B2 (ja) | 2011-03-08 | 2016-07-22 | ピリジルカルベンリン光発光体 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2016143865A Active JP6316351B2 (ja) | 2011-03-08 | 2016-07-22 | ピリジルカルベンリン光発光体 |
Country Status (6)
Country | Link |
---|---|
US (4) | US8883322B2 (ja) |
EP (3) | EP3936512A1 (ja) |
JP (2) | JP6073819B2 (ja) |
KR (2) | KR20140017591A (ja) |
TW (2) | TWI638820B (ja) |
WO (1) | WO2012121936A2 (ja) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2013045923A (ja) * | 2011-08-25 | 2013-03-04 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子、照明装置及び表示装置 |
JP2013045865A (ja) * | 2011-08-24 | 2013-03-04 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子 |
JP2014523874A (ja) * | 2011-06-14 | 2014-09-18 | ビーエーエスエフ ソシエタス・ヨーロピア | アザベンズイミダゾールカルベン配位子を有する金属錯体および有機発光ダイオードにおける当該金属錯体の使用 |
JP2017216454A (ja) * | 2017-06-15 | 2017-12-07 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子、照明装置及び表示装置 |
JP2020102633A (ja) * | 2015-06-03 | 2020-07-02 | ユー・ディー・シー アイルランド リミテッド | 減衰時間がきわめて短く高度に効率的なoledデバイス |
Families Citing this family (83)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8883322B2 (en) | 2011-03-08 | 2014-11-11 | Universal Display Corporation | Pyridyl carbene phosphorescent emitters |
KR20120135363A (ko) * | 2011-06-01 | 2012-12-13 | 엘지디스플레이 주식회사 | 청색 인광 화합물 및 이를 이용한 유기전계 발광소자 |
US9315724B2 (en) * | 2011-06-14 | 2016-04-19 | Basf Se | Metal complexes comprising azabenzimidazole carbene ligands and the use thereof in OLEDs |
KR101673521B1 (ko) * | 2012-03-02 | 2016-11-08 | 삼성디스플레이 주식회사 | 파이렌계 화합물, 이를 포함한 유기 발광 소자 및 이를 포함한 유기 발광 장치 |
WO2013137089A1 (en) * | 2012-03-14 | 2013-09-19 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element, light-emitting device, display device, electronic device, and lighting device |
JP6217642B2 (ja) | 2012-08-24 | 2017-10-25 | コニカミノルタ株式会社 | 透明電極、電子デバイス、および透明電極の製造方法 |
EP3318566B1 (en) | 2012-09-20 | 2020-06-24 | UDC Ireland Limited | Azadibenzofurans for electronic applications |
WO2014072320A1 (en) | 2012-11-06 | 2014-05-15 | Basf Se | Phenoxasiline based compounds for electronic application |
US8946697B1 (en) * | 2012-11-09 | 2015-02-03 | Universal Display Corporation | Iridium complexes with aza-benzo fused ligands |
KR102008321B1 (ko) * | 2012-11-13 | 2019-08-07 | 엘지디스플레이 주식회사 | 청색 인광 화합물 및 이를 이용하는 유기발광다이오드소자 |
US20150340612A1 (en) * | 2013-01-03 | 2015-11-26 | Merck Patent Gmbh | Uv emitters comprising a multiple bond |
TWI609022B (zh) | 2013-03-20 | 2017-12-21 | Udc愛爾蘭責任有限公司 | 在有機發光二極體中作爲增效劑之氮雜苯并咪唑碳烯錯合物 |
KR102098340B1 (ko) | 2013-04-29 | 2020-04-13 | 유디씨 아일랜드 리미티드 | 카르벤 리간드를 갖는 전이 금속 착물 및 oled에서의 그의 용도 |
KR102086554B1 (ko) * | 2013-06-12 | 2020-03-10 | 삼성디스플레이 주식회사 | 이리듐 착물 및 이를 포함한 유기 발광 소자 |
WO2015000955A1 (en) | 2013-07-02 | 2015-01-08 | Basf Se | Monosubstituted diazabenzimidazole carbene metal complexes for use in organic light emitting diodes |
US20150028290A1 (en) * | 2013-07-25 | 2015-01-29 | Universal Display Corporation | Heteroleptic osmium complex and method of making the same |
WO2015014835A1 (en) | 2013-07-31 | 2015-02-05 | Basf Se | Luminescent diazabenzimidazole carbene metal complexes |
EP3063153B1 (en) | 2013-10-31 | 2018-03-07 | Idemitsu Kosan Co., Ltd. | Azadibenzothiophenes for electronic applications |
CN105993083B (zh) | 2013-12-20 | 2018-07-03 | Udc 爱尔兰有限责任公司 | 具有极短衰变时间的高效oled装置 |
KR102330660B1 (ko) | 2014-03-31 | 2021-11-24 | 유디씨 아일랜드 리미티드 | o-치환된 비-사이클로메탈화 아릴 그룹을 갖는 카르벤 리간드를 포함하는 금속 착체 및 유기 발광 다이오드에서의 이의 용도 |
US10862053B2 (en) * | 2014-04-04 | 2020-12-08 | Konica Minolta, Inc. | Method for synthesizing organic metal complex and organic electroluminescent element using compound synthesized by said synthesis method |
WO2016016791A1 (en) | 2014-07-28 | 2016-02-04 | Idemitsu Kosan Co., Ltd (Ikc) | 2,9-functionalized benzimidazolo[1,2-a]benzimidazoles as hosts for organic light emitting diodes (oleds) |
US10341968B2 (en) * | 2014-08-07 | 2019-07-02 | Intel IP Corporation | Resource allocation and UE behavior for D2D synchronization signal transmission for inter-cell D2D discovery |
EP2982676B1 (en) | 2014-08-07 | 2018-04-11 | Idemitsu Kosan Co., Ltd. | Benzimidazo[2,1-B]benzoxazoles for electronic applications |
TWI690534B (zh) | 2014-08-08 | 2020-04-11 | 愛爾蘭商Udc愛爾蘭責任有限公司 | 電致發光咪唑并喹噁啉碳烯金屬錯合物 |
EP2993215B1 (en) | 2014-09-04 | 2019-06-19 | Idemitsu Kosan Co., Ltd. | Azabenzimidazo[2,1-a]benzimidazoles for electronic applications |
EP3015469B1 (en) | 2014-10-30 | 2018-12-19 | Idemitsu Kosan Co., Ltd. | 5-(benzimidazol-2-yl)benzimidazo[1,2-a]benzimidazoles for electronic applications |
WO2016079667A1 (en) | 2014-11-17 | 2016-05-26 | Idemitsu Kosan Co., Ltd. | Indole derivatives for electronic applications |
WO2016079169A1 (en) | 2014-11-18 | 2016-05-26 | Basf Se | Pt- or pd-carbene complexes for use in organic light emitting diodes |
EP3034507A1 (en) | 2014-12-15 | 2016-06-22 | Idemitsu Kosan Co., Ltd | 1-functionalized dibenzofurans and dibenzothiophenes for organic light emitting diodes (OLEDs) |
EP3034506A1 (en) | 2014-12-15 | 2016-06-22 | Idemitsu Kosan Co., Ltd | 4-functionalized carbazole derivatives for electronic applications |
EP3054498B1 (en) | 2015-02-06 | 2017-09-20 | Idemitsu Kosan Co., Ltd. | Bisimidazodiazocines |
EP3053918B1 (en) | 2015-02-06 | 2018-04-11 | Idemitsu Kosan Co., Ltd. | 2-carbazole substituted benzimidazoles for electronic applications |
EP3061759B1 (en) | 2015-02-24 | 2019-12-25 | Idemitsu Kosan Co., Ltd | Nitrile substituted dibenzofurans |
US11056657B2 (en) * | 2015-02-27 | 2021-07-06 | University Display Corporation | Organic electroluminescent materials and devices |
GB2536212A (en) * | 2015-03-04 | 2016-09-14 | Cambridge Display Tech Ltd | Light-emitting material and organic light-emitting device |
EP3070144B1 (en) | 2015-03-17 | 2018-02-28 | Idemitsu Kosan Co., Ltd. | Seven-membered ring compounds |
EP3072943B1 (en) | 2015-03-26 | 2018-05-02 | Idemitsu Kosan Co., Ltd. | Dibenzofuran/carbazole-substituted benzonitriles |
EP3075737B1 (en) | 2015-03-31 | 2019-12-04 | Idemitsu Kosan Co., Ltd | Benzimidazolo[1,2-a]benzimidazole carrying aryl- or heteroarylnitril groups for organic light emitting diodes |
US20180269407A1 (en) | 2015-10-01 | 2018-09-20 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazole carrying triazine groups for organic light emitting diodes |
EP3150604B1 (en) | 2015-10-01 | 2021-07-14 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazole carrying benzimidazolo[1,2-a]benzimidazolylyl groups, carbazolyl groups, benzofurane groups or benzothiophene groups for organic light emitting diodes |
EP3356368B1 (en) | 2015-10-01 | 2021-07-21 | Idemitsu Kosan Co., Ltd | Benzimidazolo[1,2-a]benzimidazole carrying benzimidazolo[1,2-a]benzimidazolyl groups, carbazolyl groups, benzofurane groups or benzothiophene groups for organic light emitting diodes |
EP3150606B1 (en) | 2015-10-01 | 2019-08-14 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazoles carrying benzofurane or benzothiophene groups for organic light emitting diodes |
KR20180079328A (ko) | 2015-11-04 | 2018-07-10 | 이데미쓰 고산 가부시키가이샤 | 벤즈이미다졸 축합 헤테로아릴 |
US11174258B2 (en) | 2015-12-04 | 2021-11-16 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazole derivatives for organic light emitting diodes |
KR102684614B1 (ko) | 2015-12-21 | 2024-07-15 | 유디씨 아일랜드 리미티드 | 삼각형 리간드를 갖는 전이 금속 착체 및 oled에서의 이의 용도 |
JP6788314B2 (ja) | 2016-01-06 | 2020-11-25 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子、有機エレクトロルミネッセンス素子の製造方法、表示装置及び照明装置 |
WO2017178864A1 (en) | 2016-04-12 | 2017-10-19 | Idemitsu Kosan Co., Ltd. | Seven-membered ring compounds |
KR102671041B1 (ko) | 2016-10-20 | 2024-06-03 | 삼성디스플레이 주식회사 | 유기금속 화합물 및 이를 포함한 유기 발광 소자 |
KR102693423B1 (ko) * | 2016-10-26 | 2024-08-09 | 삼성전자주식회사 | 유기금속 화합물 및 이를 포함한 유기 발광 소자 |
US10396298B2 (en) * | 2017-01-25 | 2019-08-27 | National Tsing Hua University | Iridium complex and organic light-emitting diode using the same |
KR102606281B1 (ko) | 2017-07-14 | 2023-11-27 | 삼성디스플레이 주식회사 | 유기금속 화합물 및 이를 포함하는 유기 발광 소자 |
KR102474204B1 (ko) | 2017-07-21 | 2022-12-06 | 삼성디스플레이 주식회사 | 유기금속 화합물 및 이를 포함하는 유기 발광 소자 |
KR20190011866A (ko) * | 2017-07-25 | 2019-02-08 | 삼성디스플레이 주식회사 | 유기금속 화합물 및 이를 포함한 유기 발광 소자 |
KR102456073B1 (ko) | 2017-07-28 | 2022-10-19 | 삼성디스플레이 주식회사 | 유기금속 화합물 및 이를 포함한 유기 발광 소자 |
WO2020053150A1 (en) | 2018-09-12 | 2020-03-19 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
TW202030902A (zh) | 2018-09-12 | 2020-08-16 | 德商麥克專利有限公司 | 電致發光裝置 |
TWI826522B (zh) | 2018-09-12 | 2023-12-21 | 德商麥克專利有限公司 | 電致發光裝置 |
KR102285174B1 (ko) * | 2018-10-29 | 2021-08-03 | 고려대학교 산학협력단 | 직각구조의 아릴-작용기가 결합된 청색 인광 화합물 및 이를 이용한 유기발광소자 |
WO2020091344A1 (ko) * | 2018-10-29 | 2020-05-07 | 고려대학교 산학협력단 | 직각구조의 아릴-작용기가 결합된 청색 인광 화합물 및 이를 이용한 유기발광소자 |
US20220127286A1 (en) | 2019-03-04 | 2022-04-28 | Merck Patent Gmbh | Ligands for nano-sized materials |
KR102188262B1 (ko) * | 2019-03-11 | 2020-12-08 | 부산대학교 산학협력단 | 진청색 이리듐 착화합물 및 이를 포함하는 유기전계발광소자 |
EP3947338A4 (en) * | 2019-03-27 | 2023-01-04 | Kemin Industries, Inc. | PROCESS FOR THE PREPARATION OF METAL CARBOXYLATES IN A ONE-POT REACTION |
KR20200118943A (ko) | 2019-04-08 | 2020-10-19 | 삼성디스플레이 주식회사 | 유기금속 화합물 및 이를 포함한 유기 발광 소자 |
KR20210151882A (ko) | 2019-04-11 | 2021-12-14 | 메르크 파텐트 게엠베하 | 유기 전계 발광 디바이스용 재료 |
KR20200121424A (ko) * | 2019-04-15 | 2020-10-26 | 삼성디스플레이 주식회사 | 유기금속 화합물, 이를 포함하는 유기 발광 소자 및 이를 포함하는 장치 |
KR102698885B1 (ko) | 2019-05-10 | 2024-08-28 | 삼성디스플레이 주식회사 | 유기금속 화합물 및 이를 포함한 유기 발광 소자 |
KR20200143621A (ko) | 2019-06-14 | 2020-12-24 | 삼성디스플레이 주식회사 | 유기 발광 소자 및 유기금속 화합물 |
KR102307305B1 (ko) * | 2019-06-20 | 2021-09-29 | 고려대학교 세종산학협력단 | 청색 인광 화합물 및 이를 포함하는 유기발광소자 |
US11820783B2 (en) * | 2019-09-06 | 2023-11-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN112457349A (zh) * | 2019-09-06 | 2021-03-09 | 环球展览公司 | 有机电致发光材料和装置 |
KR20220092590A (ko) | 2019-11-04 | 2022-07-01 | 메르크 파텐트 게엠베하 | 유기 전계 발광 디바이스용 재료 |
TW202134252A (zh) | 2019-11-12 | 2021-09-16 | 德商麥克專利有限公司 | 有機電致發光裝置用材料 |
KR102373027B1 (ko) * | 2019-11-13 | 2022-03-11 | 고려대학교 산학협력단 | 청색 인광소재, 그 제조 방법, 및 이의 광물리적 특성 |
TW202136181A (zh) | 2019-12-04 | 2021-10-01 | 德商麥克專利有限公司 | 有機電致發光裝置用的材料 |
CN115052865A (zh) | 2020-01-29 | 2022-09-13 | 默克专利有限公司 | 苯并咪唑衍生物 |
US20230337537A1 (en) | 2020-03-23 | 2023-10-19 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
KR20210119003A (ko) | 2020-03-23 | 2021-10-05 | 삼성디스플레이 주식회사 | 유기금속 화합물 및 이를 포함하는 유기 발광 소자 |
KR20210142032A (ko) | 2020-05-14 | 2021-11-24 | 삼성디스플레이 주식회사 | 유기금속 화합물 및 이를 포함한 유기 발광 소자 |
KR20220007827A (ko) * | 2020-07-10 | 2022-01-19 | 삼성디스플레이 주식회사 | 발광 소자 재료의 정제 방법 및 상기 방법으로 정제된 재료를 포함하는 발광 소자 |
CN114213374B (zh) * | 2021-12-28 | 2024-05-31 | 棓诺(苏州)新材料有限公司 | 4-氨基氧芴的合成方法 |
KR20240016819A (ko) * | 2022-07-29 | 2024-02-06 | 삼성전자주식회사 | 유기금속 화합물, 이를 포함한 유기 발광 소자 및 상기 유기 발광 소자를 포함한 전자 장치 |
WO2024105066A1 (en) | 2022-11-17 | 2024-05-23 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
Citations (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20050260447A1 (en) * | 2004-05-18 | 2005-11-24 | Jason Brooks | Cyclometallated iridium carbene complexes for use as hosts |
US20050260448A1 (en) * | 2004-05-18 | 2005-11-24 | Chun Lin | Novel organometallic compounds for use in electroluminescent devices |
WO2006114966A1 (ja) * | 2005-04-18 | 2006-11-02 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
JP2008521946A (ja) * | 2004-11-25 | 2008-06-26 | ビーエーエスエフ ソシエタス・ヨーロピア | 有機発光ダイオード(oled)における遷移金属−カルベン錯体の使用 |
US20080200686A1 (en) * | 2005-06-14 | 2008-08-21 | Basf Aktiengesellschaft | Method for the Isomerisation of Transition Metal Complexes Containing Cyclometallated, Carbene Ligands |
WO2009070382A1 (en) * | 2007-11-27 | 2009-06-04 | The Regents Of The University Of Michigan | Organic light emitting device having multiple separate emissive layers |
JP2009525299A (ja) * | 2006-01-31 | 2009-07-09 | ビーエーエスエフ ソシエタス・ヨーロピア | 遷移金属カルベン錯体の製造方法 |
JP2009532431A (ja) * | 2006-04-05 | 2009-09-10 | ビーエーエスエフ ソシエタス・ヨーロピア | ヘテロレプティックな遷移金属−カルベン錯体及びそれを有機発光ダイオード(oled)において用いる使用 |
JP2010515255A (ja) * | 2006-12-28 | 2010-05-06 | ユニバーサル ディスプレイ コーポレイション | 長寿命リン光発光有機発光デバイス(oled)構造 |
WO2010062643A1 (en) * | 2008-10-28 | 2010-06-03 | The Regents Of The University Of Michigan | Stacked white oled having separate red, green and blue sub-elements |
WO2010068330A1 (en) * | 2008-12-12 | 2010-06-17 | Universal Display Corporation | Improved oled stability via doped hole transport layer |
JP2010532400A (ja) * | 2007-07-05 | 2010-10-07 | ビーエーエスエフ ソシエタス・ヨーロピア | カルベン遷移金属錯体発光体、ならびにジシリルカルバゾール、ジシリルジベンゾフラン、ジシリルジベンゾチオフェン、ジシリルジベンゾホスホール、ジシリルジベンゾチオフェンs−オキシドおよびジシリルジベンゾチオフェンs,s−ジオキシドから選択される少なくとも1つの化合物を含む有機発光ダイオード |
WO2010129323A1 (en) * | 2009-04-28 | 2010-11-11 | Universal Display Corporation | Iridium complex with methyl-d3 substitution |
JP2010540656A (ja) * | 2007-10-04 | 2010-12-24 | ユニバーサル ディスプレイ コーポレイション | 三座配位子をもつ錯体 |
WO2011157790A1 (en) * | 2010-06-18 | 2011-12-22 | Basf Se | Organic electronic devices comprising a layer of a dibenzofurane compound and a 8-hydroxyquinolinolato earth alkaline metal, or alkali metal complex |
WO2011158204A1 (en) * | 2010-06-18 | 2011-12-22 | Basf Se | Organic electronic devices comprising the layer containing at least one metal organic compound and at least one metal oxide |
Family Cites Families (128)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4769292A (en) | 1987-03-02 | 1988-09-06 | Eastman Kodak Company | Electroluminescent device with modified thin film luminescent zone |
GB8909011D0 (en) | 1989-04-20 | 1989-06-07 | Friend Richard H | Electroluminescent devices |
US5061569A (en) | 1990-07-26 | 1991-10-29 | Eastman Kodak Company | Electroluminescent device with organic electroluminescent medium |
DE69412567T2 (de) | 1993-11-01 | 1999-02-04 | Hodogaya Chemical Co., Ltd., Tokio/Tokyo | Aminverbindung und sie enthaltende Elektrolumineszenzvorrichtung |
US5707745A (en) | 1994-12-13 | 1998-01-13 | The Trustees Of Princeton University | Multicolor organic light emitting devices |
US5703436A (en) | 1994-12-13 | 1997-12-30 | The Trustees Of Princeton University | Transparent contacts for organic devices |
US6939625B2 (en) | 1996-06-25 | 2005-09-06 | Nôrthwestern University | Organic light-emitting diodes and methods for assembly and enhanced charge injection |
US5844363A (en) | 1997-01-23 | 1998-12-01 | The Trustees Of Princeton Univ. | Vacuum deposited, non-polymeric flexible organic light emitting devices |
US6091195A (en) | 1997-02-03 | 2000-07-18 | The Trustees Of Princeton University | Displays having mesa pixel configuration |
US5834893A (en) | 1996-12-23 | 1998-11-10 | The Trustees Of Princeton University | High efficiency organic light emitting devices with light directing structures |
US6013982A (en) | 1996-12-23 | 2000-01-11 | The Trustees Of Princeton University | Multicolor display devices |
US6303238B1 (en) | 1997-12-01 | 2001-10-16 | The Trustees Of Princeton University | OLEDs doped with phosphorescent compounds |
US6337102B1 (en) | 1997-11-17 | 2002-01-08 | The Trustees Of Princeton University | Low pressure vapor phase deposition of organic thin films |
US6087196A (en) | 1998-01-30 | 2000-07-11 | The Trustees Of Princeton University | Fabrication of organic semiconductor devices using ink jet printing |
US6528187B1 (en) | 1998-09-08 | 2003-03-04 | Fuji Photo Film Co., Ltd. | Material for luminescence element and luminescence element using the same |
US6830828B2 (en) | 1998-09-14 | 2004-12-14 | The Trustees Of Princeton University | Organometallic complexes as phosphorescent emitters in organic LEDs |
US6097147A (en) | 1998-09-14 | 2000-08-01 | The Trustees Of Princeton University | Structure for high efficiency electroluminescent device |
US6294398B1 (en) | 1999-11-23 | 2001-09-25 | The Trustees Of Princeton University | Method for patterning devices |
US6458475B1 (en) | 1999-11-24 | 2002-10-01 | The Trustee Of Princeton University | Organic light emitting diode having a blue phosphorescent molecule as an emitter |
KR100377321B1 (ko) | 1999-12-31 | 2003-03-26 | 주식회사 엘지화학 | 피-형 반도체 성질을 갖는 유기 화합물을 포함하는 전기소자 |
US20020121638A1 (en) | 2000-06-30 | 2002-09-05 | Vladimir Grushin | Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds |
WO2002015645A1 (en) | 2000-08-11 | 2002-02-21 | The Trustees Of Princeton University | Organometallic compounds and emission-shifting organic electrophosphorescence |
US6579630B2 (en) | 2000-12-07 | 2003-06-17 | Canon Kabushiki Kaisha | Deuterated semiconducting organic compounds used for opto-electronic devices |
JP3812730B2 (ja) | 2001-02-01 | 2006-08-23 | 富士写真フイルム株式会社 | 遷移金属錯体及び発光素子 |
JP4307000B2 (ja) | 2001-03-08 | 2009-08-05 | キヤノン株式会社 | 金属配位化合物、電界発光素子及び表示装置 |
JP4310077B2 (ja) | 2001-06-19 | 2009-08-05 | キヤノン株式会社 | 金属配位化合物及び有機発光素子 |
ATE431970T1 (de) | 2001-06-20 | 2009-06-15 | Showa Denko Kk | Licht emittierendes material und organische leuchtdiode |
US7071615B2 (en) | 2001-08-20 | 2006-07-04 | Universal Display Corporation | Transparent electrodes |
US7250226B2 (en) | 2001-08-31 | 2007-07-31 | Nippon Hoso Kyokai | Phosphorescent compound, a phosphorescent composition and an organic light-emitting device |
US7431968B1 (en) | 2001-09-04 | 2008-10-07 | The Trustees Of Princeton University | Process and apparatus for organic vapor jet deposition |
US6835469B2 (en) | 2001-10-17 | 2004-12-28 | The University Of Southern California | Phosphorescent compounds and devices comprising the same |
US7166368B2 (en) | 2001-11-07 | 2007-01-23 | E. I. Du Pont De Nemours And Company | Electroluminescent platinum compounds and devices made with such compounds |
US6863997B2 (en) | 2001-12-28 | 2005-03-08 | The Trustees Of Princeton University | White light emitting OLEDs from combined monomer and aggregate emission |
KR100691543B1 (ko) | 2002-01-18 | 2007-03-09 | 주식회사 엘지화학 | 새로운 전자 수송용 물질 및 이를 이용한 유기 발광 소자 |
US6878975B2 (en) | 2002-02-08 | 2005-04-12 | Agilent Technologies, Inc. | Polarization field enhanced tunnel structures |
US20030230980A1 (en) | 2002-06-18 | 2003-12-18 | Forrest Stephen R | Very low voltage, high efficiency phosphorescent oled in a p-i-n structure |
US7189989B2 (en) | 2002-08-22 | 2007-03-13 | Fuji Photo Film Co., Ltd. | Light emitting element |
CN100439469C (zh) | 2002-08-27 | 2008-12-03 | 富士胶片株式会社 | 有机金属配位化合物、有机el元件及有机el显示器 |
US6687266B1 (en) | 2002-11-08 | 2004-02-03 | Universal Display Corporation | Organic light emitting materials and devices |
JP4365196B2 (ja) | 2002-12-27 | 2009-11-18 | 富士フイルム株式会社 | 有機電界発光素子 |
JP4365199B2 (ja) | 2002-12-27 | 2009-11-18 | 富士フイルム株式会社 | 有機電界発光素子 |
CN100387607C (zh) | 2003-03-24 | 2008-05-14 | 南加利福尼亚大学 | Ir的苯基-吡唑配合物 |
US7090928B2 (en) | 2003-04-01 | 2006-08-15 | The University Of Southern California | Binuclear compounds |
EP1717291A3 (de) | 2003-04-15 | 2007-03-21 | Merck Patent GmbH | Mischungen von organischen, zur Emission befähigten Halbleitern und Maxtrixmaterialien, deren Verwendung und diese Mischungen enthaltende Elektronikbauteile |
US7029765B2 (en) | 2003-04-22 | 2006-04-18 | Universal Display Corporation | Organic light emitting devices having reduced pixel shrinkage |
US20060186791A1 (en) | 2003-05-29 | 2006-08-24 | Osamu Yoshitake | Organic electroluminescent element |
JP2005011610A (ja) | 2003-06-18 | 2005-01-13 | Nippon Steel Chem Co Ltd | 有機電界発光素子 |
US20050025993A1 (en) | 2003-07-25 | 2005-02-03 | Thompson Mark E. | Materials and structures for enhancing the performance of organic light emitting devices |
TWI390006B (zh) | 2003-08-07 | 2013-03-21 | Nippon Steel Chemical Co | Organic EL materials with aluminum clamps |
DE10338550A1 (de) | 2003-08-19 | 2005-03-31 | Basf Ag | Übergangsmetallkomplexe mit Carbenliganden als Emitter für organische Licht-emittierende Dioden (OLEDs) |
US20060269780A1 (en) | 2003-09-25 | 2006-11-30 | Takayuki Fukumatsu | Organic electroluminescent device |
JP4822687B2 (ja) | 2003-11-21 | 2011-11-24 | 富士フイルム株式会社 | 有機電界発光素子 |
US7332232B2 (en) | 2004-02-03 | 2008-02-19 | Universal Display Corporation | OLEDs utilizing multidentate ligand systems |
KR100834327B1 (ko) | 2004-03-11 | 2008-06-02 | 미쓰비시 가가꾸 가부시키가이샤 | 전하 수송막용 조성물 및 이온 화합물, 이를 이용한 전하수송막 및 유기 전계 발광 장치, 및 유기 전계 발광 장치의제조 방법 및 전하 수송막의 제조 방법 |
TW200531592A (en) | 2004-03-15 | 2005-09-16 | Nippon Steel Chemical Co | Organic electroluminescent device |
JP4869565B2 (ja) | 2004-04-23 | 2012-02-08 | 富士フイルム株式会社 | 有機電界発光素子 |
WO2005113704A2 (en) | 2004-05-18 | 2005-12-01 | The University Of Southern California | Luminescent compounds with carbene ligands |
US7491823B2 (en) | 2004-05-18 | 2009-02-17 | The University Of Southern California | Luminescent compounds with carbene ligands |
US7445855B2 (en) | 2004-05-18 | 2008-11-04 | The University Of Southern California | Cationic metal-carbene complexes |
US7279704B2 (en) | 2004-05-18 | 2007-10-09 | The University Of Southern California | Complexes with tridentate ligands |
US7393599B2 (en) | 2004-05-18 | 2008-07-01 | The University Of Southern California | Luminescent compounds with carbene ligands |
WO2005123873A1 (ja) | 2004-06-17 | 2005-12-29 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
JP5000496B2 (ja) | 2004-06-28 | 2012-08-15 | チバ ホールディング インコーポレーテッド | トリアゾールとベンゾトリアゾールのエレクトロルミネセンス金属錯体 |
US20060008670A1 (en) | 2004-07-06 | 2006-01-12 | Chun Lin | Organic light emitting materials and devices |
US7504657B2 (en) | 2004-07-23 | 2009-03-17 | Konica Minolta Holdings, Inc. | Organic electroluminescent element, display and illuminator |
JP2008526766A (ja) | 2004-12-30 | 2008-07-24 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 有機金属錯体 |
US8377571B2 (en) | 2005-02-04 | 2013-02-19 | Konica Minolta Holdings, Inc. | Material for organic electroluminescence element, organic electroluminescence element, display device and lighting device |
KR100803125B1 (ko) | 2005-03-08 | 2008-02-14 | 엘지전자 주식회사 | 적색 인광 화합물 및 이를 사용한 유기전계발광소자 |
WO2006098120A1 (ja) | 2005-03-16 | 2006-09-21 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子 |
DE102005014284A1 (de) | 2005-03-24 | 2006-09-28 | Basf Ag | Verwendung von Verbindungen, welche aromatische oder heteroaromatische über Carbonyl-Gruppen enthaltende Gruppen verbundene Ringe enthalten, als Matrixmaterialien in organischen Leuchtdioden |
JPWO2006103874A1 (ja) | 2005-03-29 | 2008-09-04 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
US7807275B2 (en) | 2005-04-21 | 2010-10-05 | Universal Display Corporation | Non-blocked phosphorescent OLEDs |
TWI418606B (zh) * | 2005-04-25 | 2013-12-11 | Udc Ireland Ltd | 有機電致發光裝置 |
JP4533796B2 (ja) | 2005-05-06 | 2010-09-01 | 富士フイルム株式会社 | 有機電界発光素子 |
US9051344B2 (en) | 2005-05-06 | 2015-06-09 | Universal Display Corporation | Stability OLED materials and devices |
EP1888708B1 (en) | 2005-05-31 | 2012-11-21 | Universal Display Corporation | Triphenylene hosts in phosphorescent light emitting diodes |
US8709614B2 (en) | 2005-06-07 | 2014-04-29 | Nippon Steel & Sumikin Chemical Co., Ltd. | Organic metal complex and its use in organic electroluminescent device |
WO2007002683A2 (en) | 2005-06-27 | 2007-01-04 | E. I. Du Pont De Nemours And Company | Electrically conductive polymer compositions |
WO2007004380A1 (ja) | 2005-07-01 | 2007-01-11 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
WO2007028417A1 (en) | 2005-09-07 | 2007-03-15 | Technische Universität Braunschweig | Triplett emitter having condensed five-membered rings |
JP4887731B2 (ja) | 2005-10-26 | 2012-02-29 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
US7993760B2 (en) | 2005-12-01 | 2011-08-09 | Nippon Steel Chemical Co., Ltd. | Compound for use in organic electroluminescent device and organic electroluminescent device |
JPWO2007063796A1 (ja) | 2005-12-01 | 2009-05-07 | 新日鐵化学株式会社 | 有機電界発光素子 |
JPWO2007069542A1 (ja) * | 2005-12-15 | 2009-05-21 | 出光興産株式会社 | 遷移金属錯体化合物及びそれを用いた有機エレクトロルミネッセンス素子 |
KR20160030582A (ko) | 2006-02-10 | 2016-03-18 | 유니버셜 디스플레이 코포레이션 | 시클로금속화 이미다조[1,2-f]페난트리딘 및 디이미다조[1,2-a:1'',2''-c]퀴나졸린 리간드, 및 이의 등전자성 및 벤즈고리화된 유사체의 금속 착체 |
US8142909B2 (en) | 2006-02-10 | 2012-03-27 | Universal Display Corporation | Blue phosphorescent imidazophenanthridine materials |
JP4823730B2 (ja) | 2006-03-20 | 2011-11-24 | 新日鐵化学株式会社 | 発光層化合物及び有機電界発光素子 |
WO2007123392A1 (en) | 2006-04-24 | 2007-11-01 | Erasmus Universiteit Rotterdam | Determining the replicative history of lymphocytes |
EP2011790B1 (en) | 2006-04-26 | 2016-06-29 | Idemitsu Kosan Co., Ltd. | Aromatic amine derivative, and organic electroluminescence element using the same |
WO2007132678A1 (ja) | 2006-05-11 | 2007-11-22 | Idemitsu Kosan Co., Ltd. | 有機エレクトロルミネッセンス素子 |
CN101461074B (zh) | 2006-06-02 | 2011-06-15 | 出光兴产株式会社 | 有机电致发光元件用材料及使用了它的有机电致发光元件 |
KR20090040896A (ko) | 2006-08-23 | 2009-04-27 | 이데미쓰 고산 가부시키가이샤 | 방향족 아민 유도체 및 이들을 이용한 유기 전기발광 소자 |
JP5589251B2 (ja) | 2006-09-21 | 2014-09-17 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子材料 |
EP2080762B1 (en) | 2006-11-09 | 2016-09-14 | Nippon Steel & Sumikin Chemical Co., Ltd. | Compound for organic electroluminescent device and organic electroluminescent device |
KR101347519B1 (ko) | 2006-11-24 | 2014-01-03 | 이데미쓰 고산 가부시키가이샤 | 방향족 아민 유도체 및 그것을 이용한 유기 전기발광 소자 |
US8119255B2 (en) | 2006-12-08 | 2012-02-21 | Universal Display Corporation | Cross-linkable iridium complexes and organic light-emitting devices using the same |
WO2008101842A1 (en) | 2007-02-23 | 2008-08-28 | Basf Se | Electroluminescent metal complexes with benzotriazoles |
CN101687893B (zh) | 2007-04-26 | 2014-01-22 | 巴斯夫欧洲公司 | 含有吩噻嗪s-氧化物或吩噻嗪s,s-二氧化物基团的硅烷及其在oled中的用途 |
EP2170911B1 (en) | 2007-06-22 | 2018-11-28 | UDC Ireland Limited | Light emitting cu(i) complexes |
WO2009008205A1 (ja) | 2007-07-07 | 2009-01-15 | Idemitsu Kosan Co., Ltd. | 有機エレクトロルミネッセンス素子および有機エレクトロルミネッセンス素子用材料 |
US8779655B2 (en) | 2007-07-07 | 2014-07-15 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and material for organic electroluminescence device |
US8021574B2 (en) | 2007-07-07 | 2011-09-20 | Idemitsu Kosan Co., Ltd. | Naphthalene derivative, material for organic electroluminescence device, and organic electroluminescence device using the same |
US20090045731A1 (en) | 2007-07-07 | 2009-02-19 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and material for organic electroluminescence device |
JP5473600B2 (ja) | 2007-07-07 | 2014-04-16 | 出光興産株式会社 | クリセン誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
US8080658B2 (en) | 2007-07-10 | 2011-12-20 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescent element and organic electroluminescent element employing the same |
US8114530B2 (en) | 2007-07-10 | 2012-02-14 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescence device and organic electroluminescence device utilizing the same |
EP2173811A1 (en) | 2007-07-27 | 2010-04-14 | E. I. du Pont de Nemours and Company | Aqueous dispersions of electrically conducting polymers containing inorganic nanoparticles |
KR20160086983A (ko) | 2007-08-08 | 2016-07-20 | 유니버셜 디스플레이 코포레이션 | 트리페닐렌기를 포함하는 벤조 융합 티오펜 또는 벤조 융합 푸란 화합물 |
JP2009040728A (ja) | 2007-08-09 | 2009-02-26 | Canon Inc | 有機金属錯体及びこれを用いた有機発光素子 |
US8383249B2 (en) * | 2007-10-04 | 2013-02-26 | Universal Display Corporation | Complexes with tridentate ligands |
KR101642030B1 (ko) | 2007-10-17 | 2016-07-25 | 바스프 에스이 | 가교된 카르벤 리간드를 포함하는 전이 금속 착물 및 이의 용도 |
US20090101870A1 (en) | 2007-10-22 | 2009-04-23 | E. I. Du Pont De Nemours And Company | Electron transport bi-layers and devices made with such bi-layers |
US7914908B2 (en) | 2007-11-02 | 2011-03-29 | Global Oled Technology Llc | Organic electroluminescent device having an azatriphenylene derivative |
DE102007053771A1 (de) | 2007-11-12 | 2009-05-14 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtungen |
EP2216313B1 (en) | 2007-11-15 | 2013-02-20 | Idemitsu Kosan Co., Ltd. | Benzochrysene derivative and organic electroluminescent device using the same |
JP5270571B2 (ja) | 2007-11-22 | 2013-08-21 | 出光興産株式会社 | 有機el素子 |
EP2221897A4 (en) | 2007-11-22 | 2012-08-08 | Idemitsu Kosan Co | ORGANIC EL ELEMENT AND ORGANIC EL-MATERIAL SOLUTION |
WO2009073245A1 (en) | 2007-12-06 | 2009-06-11 | Universal Display Corporation | Light-emitting organometallic complexes |
US8221905B2 (en) | 2007-12-28 | 2012-07-17 | Universal Display Corporation | Carbazole-containing materials in phosphorescent light emitting diodes |
WO2009085344A2 (en) | 2007-12-28 | 2009-07-09 | Universal Display Corporation | Dibenzothiophene-containing materials in phosphorescent light emitting diodes |
US8471248B2 (en) | 2008-02-12 | 2013-06-25 | Basf Se | Electroluminiscent metal complexes with dibenzo[f,h] quinoxalines |
JP5882223B2 (ja) | 2009-12-14 | 2016-03-09 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | ジアザベンゾイミダゾールカルベン配位子を含む金属錯体及び該錯体をoledにおいて用いる使用 |
US9142792B2 (en) * | 2010-06-18 | 2015-09-22 | Basf Se | Organic electronic devices comprising a layer comprising at least one metal organic compound and at least one metal oxide |
US8748011B2 (en) * | 2011-02-23 | 2014-06-10 | Universal Display Corporation | Ruthenium carbene complexes for OLED material |
US8883322B2 (en) | 2011-03-08 | 2014-11-11 | Universal Display Corporation | Pyridyl carbene phosphorescent emitters |
WO2012170461A1 (en) * | 2011-06-08 | 2012-12-13 | Universal Display Corporation | Heteroleptic iridium carbene complexes and light emitting device using them |
US9315724B2 (en) * | 2011-06-14 | 2016-04-19 | Basf Se | Metal complexes comprising azabenzimidazole carbene ligands and the use thereof in OLEDs |
GB2536212A (en) * | 2015-03-04 | 2016-09-14 | Cambridge Display Tech Ltd | Light-emitting material and organic light-emitting device |
-
2011
- 2011-03-08 US US13/043,180 patent/US8883322B2/en active Active
-
2012
- 2012-02-28 KR KR1020137026567A patent/KR20140017591A/ko not_active Application Discontinuation
- 2012-02-28 EP EP21189954.7A patent/EP3936512A1/en active Pending
- 2012-02-28 JP JP2013557759A patent/JP6073819B2/ja active Active
- 2012-02-28 EP EP12708222.0A patent/EP2683728B1/en active Active
- 2012-02-28 EP EP18187166.6A patent/EP3424935B1/en active Active
- 2012-02-28 WO PCT/US2012/027044 patent/WO2012121936A2/en active Application Filing
- 2012-02-28 KR KR1020187030629A patent/KR101979179B1/ko active IP Right Grant
- 2012-03-08 TW TW105118036A patent/TWI638820B/zh active
- 2012-03-08 TW TW101107956A patent/TWI624471B/zh active
-
2014
- 2014-10-10 US US14/511,689 patent/US9972793B2/en active Active
-
2016
- 2016-07-22 JP JP2016143865A patent/JP6316351B2/ja active Active
-
2018
- 2018-04-10 US US15/949,601 patent/US10873038B2/en active Active
-
2020
- 2020-11-02 US US17/086,769 patent/US11600791B2/en active Active
Patent Citations (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20050260448A1 (en) * | 2004-05-18 | 2005-11-24 | Chun Lin | Novel organometallic compounds for use in electroluminescent devices |
US20050260447A1 (en) * | 2004-05-18 | 2005-11-24 | Jason Brooks | Cyclometallated iridium carbene complexes for use as hosts |
JP2008521946A (ja) * | 2004-11-25 | 2008-06-26 | ビーエーエスエフ ソシエタス・ヨーロピア | 有機発光ダイオード(oled)における遷移金属−カルベン錯体の使用 |
WO2006114966A1 (ja) * | 2005-04-18 | 2006-11-02 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
US20080200686A1 (en) * | 2005-06-14 | 2008-08-21 | Basf Aktiengesellschaft | Method for the Isomerisation of Transition Metal Complexes Containing Cyclometallated, Carbene Ligands |
JP2009525299A (ja) * | 2006-01-31 | 2009-07-09 | ビーエーエスエフ ソシエタス・ヨーロピア | 遷移金属カルベン錯体の製造方法 |
JP2009532431A (ja) * | 2006-04-05 | 2009-09-10 | ビーエーエスエフ ソシエタス・ヨーロピア | ヘテロレプティックな遷移金属−カルベン錯体及びそれを有機発光ダイオード(oled)において用いる使用 |
JP2010515255A (ja) * | 2006-12-28 | 2010-05-06 | ユニバーサル ディスプレイ コーポレイション | 長寿命リン光発光有機発光デバイス(oled)構造 |
JP2010532400A (ja) * | 2007-07-05 | 2010-10-07 | ビーエーエスエフ ソシエタス・ヨーロピア | カルベン遷移金属錯体発光体、ならびにジシリルカルバゾール、ジシリルジベンゾフラン、ジシリルジベンゾチオフェン、ジシリルジベンゾホスホール、ジシリルジベンゾチオフェンs−オキシドおよびジシリルジベンゾチオフェンs,s−ジオキシドから選択される少なくとも1つの化合物を含む有機発光ダイオード |
JP2010540656A (ja) * | 2007-10-04 | 2010-12-24 | ユニバーサル ディスプレイ コーポレイション | 三座配位子をもつ錯体 |
WO2009070382A1 (en) * | 2007-11-27 | 2009-06-04 | The Regents Of The University Of Michigan | Organic light emitting device having multiple separate emissive layers |
WO2010062643A1 (en) * | 2008-10-28 | 2010-06-03 | The Regents Of The University Of Michigan | Stacked white oled having separate red, green and blue sub-elements |
WO2010068330A1 (en) * | 2008-12-12 | 2010-06-17 | Universal Display Corporation | Improved oled stability via doped hole transport layer |
WO2010129323A1 (en) * | 2009-04-28 | 2010-11-11 | Universal Display Corporation | Iridium complex with methyl-d3 substitution |
WO2011157790A1 (en) * | 2010-06-18 | 2011-12-22 | Basf Se | Organic electronic devices comprising a layer of a dibenzofurane compound and a 8-hydroxyquinolinolato earth alkaline metal, or alkali metal complex |
WO2011158204A1 (en) * | 2010-06-18 | 2011-12-22 | Basf Se | Organic electronic devices comprising the layer containing at least one metal organic compound and at least one metal oxide |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014523874A (ja) * | 2011-06-14 | 2014-09-18 | ビーエーエスエフ ソシエタス・ヨーロピア | アザベンズイミダゾールカルベン配位子を有する金属錯体および有機発光ダイオードにおける当該金属錯体の使用 |
JP2018024696A (ja) * | 2011-06-14 | 2018-02-15 | ユー・ディー・シー アイルランド リミテッド | アザベンズイミダゾールカルベン配位子を有する金属錯体および有機発光ダイオードにおける当該金属錯体の使用 |
JP2013045865A (ja) * | 2011-08-24 | 2013-03-04 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子 |
JP2013045923A (ja) * | 2011-08-25 | 2013-03-04 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子、照明装置及び表示装置 |
US9260658B2 (en) | 2011-08-25 | 2016-02-16 | Konica Minolta, Inc. | Organic electroluminescence element, lighting device and display device |
JP2020102633A (ja) * | 2015-06-03 | 2020-07-02 | ユー・ディー・シー アイルランド リミテッド | 減衰時間がきわめて短く高度に効率的なoledデバイス |
JP2017216454A (ja) * | 2017-06-15 | 2017-12-07 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子、照明装置及び表示装置 |
Also Published As
Publication number | Publication date |
---|---|
EP2683728A2 (en) | 2014-01-15 |
KR20180118253A (ko) | 2018-10-30 |
US20150021590A1 (en) | 2015-01-22 |
US20120228583A1 (en) | 2012-09-13 |
WO2012121936A2 (en) | 2012-09-13 |
TW201634475A (zh) | 2016-10-01 |
EP3424935B1 (en) | 2021-08-11 |
KR101979179B1 (ko) | 2019-05-15 |
US10873038B2 (en) | 2020-12-22 |
WO2012121936A4 (en) | 2013-02-28 |
US11600791B2 (en) | 2023-03-07 |
JP6073819B2 (ja) | 2017-02-01 |
EP3936512A1 (en) | 2022-01-12 |
JP2017008063A (ja) | 2017-01-12 |
US9972793B2 (en) | 2018-05-15 |
TWI638820B (zh) | 2018-10-21 |
EP3424935A1 (en) | 2019-01-09 |
JP6316351B2 (ja) | 2018-04-25 |
TWI624471B (zh) | 2018-05-21 |
KR20140017591A (ko) | 2014-02-11 |
US20210050530A1 (en) | 2021-02-18 |
WO2012121936A3 (en) | 2012-11-22 |
EP2683728B1 (en) | 2018-09-05 |
US20190109287A1 (en) | 2019-04-11 |
TW201241002A (en) | 2012-10-16 |
US8883322B2 (en) | 2014-11-11 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6316351B2 (ja) | ピリジルカルベンリン光発光体 | |
KR102505876B1 (ko) | 도펀트로서 헤테로렙틱 이리듐 착물 | |
JP6581169B2 (ja) | 燐光性物質 | |
JP6219466B2 (ja) | リン光物質 | |
JP6251299B2 (ja) | リン光物質 | |
JP6332904B2 (ja) | 新規有機発光材料 | |
EP3473634B1 (en) | Heteroleptic iridium carbene complexes and light emitting device using them | |
JP2013056880A (ja) | 有機発光ダイオードのための材料 | |
JP6473437B2 (ja) | 高効率リン光材料 | |
JP6062741B2 (ja) | 高効率リン光材料 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140204 |
|
A072 | Dismissal of procedure [no reply to invitation to correct request for examination] |
Free format text: JAPANESE INTERMEDIATE CODE: A072 Effective date: 20140304 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20140828 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20150428 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20150512 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20150730 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20151019 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20160405 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20160722 |
|
A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20160729 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20161004 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20161124 |
|
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: 20161220 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20170105 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6073819 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
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 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |