TW200848412A - Electroluminescent metal complex - Google Patents
Electroluminescent metal complex Download PDFInfo
- Publication number
- TW200848412A TW200848412A TW097104992A TW97104992A TW200848412A TW 200848412 A TW200848412 A TW 200848412A TW 097104992 A TW097104992 A TW 097104992A TW 97104992 A TW97104992 A TW 97104992A TW 200848412 A TW200848412 A TW 200848412A
- Authority
- TW
- Taiwan
- Prior art keywords
- group
- substituted
- alkyl
- unsubstituted
- aryl
- Prior art date
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- 150000004696 coordination complex Chemical class 0.000 title claims description 12
- 239000003446 ligand Substances 0.000 claims abstract description 75
- 229910052751 metal Inorganic materials 0.000 claims abstract description 39
- 239000002184 metal Substances 0.000 claims abstract description 39
- 239000000539 dimer Substances 0.000 claims abstract description 11
- 229910052741 iridium Inorganic materials 0.000 claims abstract description 11
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 202
- 125000003118 aryl group Chemical group 0.000 claims description 132
- -1 atom oximes Chemical class 0.000 claims description 83
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 78
- 229910052739 hydrogen Inorganic materials 0.000 claims description 75
- 239000001257 hydrogen Substances 0.000 claims description 75
- 125000003545 alkoxy group Chemical group 0.000 claims description 73
- 229910052736 halogen Inorganic materials 0.000 claims description 53
- 150000001875 compounds Chemical class 0.000 claims description 52
- 150000002367 halogens Chemical group 0.000 claims description 51
- 125000001072 heteroaryl group Chemical group 0.000 claims description 40
- 150000002431 hydrogen Chemical group 0.000 claims description 39
- 125000003342 alkenyl group Chemical group 0.000 claims description 36
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 36
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 35
- 125000001424 substituent group Chemical group 0.000 claims description 34
- 229910052757 nitrogen Inorganic materials 0.000 claims description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
- 229910052799 carbon Inorganic materials 0.000 claims description 27
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 25
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 25
- 229910052707 ruthenium Inorganic materials 0.000 claims description 25
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 22
- 125000004414 alkyl thio group Chemical group 0.000 claims description 22
- 125000004429 atom Chemical group 0.000 claims description 18
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 17
- 150000001721 carbon Chemical group 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 10
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
- 125000006413 ring segment Chemical group 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 9
- 239000007789 gas Substances 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 9
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 9
- 239000004305 biphenyl Substances 0.000 claims description 8
- 125000002837 carbocyclic group Chemical group 0.000 claims description 8
- 229910052703 rhodium Inorganic materials 0.000 claims description 8
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 229910052759 nickel Inorganic materials 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 229910052763 palladium Inorganic materials 0.000 claims description 7
- 229910052697 platinum Inorganic materials 0.000 claims description 7
- 239000007983 Tris buffer Substances 0.000 claims description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 6
- 229910052742 iron Inorganic materials 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 229910052738 indium Inorganic materials 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 150000002923 oximes Chemical group 0.000 claims description 5
- 229910052727 yttrium Inorganic materials 0.000 claims description 5
- 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 4
- 229910052797 bismuth Inorganic materials 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 229910052737 gold Inorganic materials 0.000 claims description 4
- 230000005525 hole transport Effects 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 229910052715 tantalum Inorganic materials 0.000 claims description 4
- 229910052718 tin Inorganic materials 0.000 claims description 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- 229910052787 antimony Inorganic materials 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 230000008033 biological extinction Effects 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052745 lead Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
- 229910052702 rhenium Inorganic materials 0.000 claims description 3
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 claims description 3
- 229910052720 vanadium Inorganic materials 0.000 claims description 3
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 claims description 2
- 125000000172 C5-C10 aryl group Chemical group 0.000 claims description 2
- 229910021554 Chromium(II) chloride Inorganic materials 0.000 claims description 2
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 2
- 229910007161 Si(CH3)3 Inorganic materials 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 238000004166 bioassay Methods 0.000 claims description 2
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 2
- 229910052805 deuterium Inorganic materials 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 230000003068 static effect Effects 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 229940124530 sulfonamide Drugs 0.000 claims description 2
- 150000003456 sulfonamides Chemical class 0.000 claims description 2
- 238000012360 testing method Methods 0.000 claims description 2
- 229910052721 tungsten Inorganic materials 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims 3
- WXAIEIRYBSKHDP-UHFFFAOYSA-N 4-phenyl-n-(4-phenylphenyl)-n-[4-[4-(4-phenyl-n-(4-phenylphenyl)anilino)phenyl]phenyl]aniline Chemical compound C1=CC=CC=C1C1=CC=C(N(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC=CC=2)C=C1 WXAIEIRYBSKHDP-UHFFFAOYSA-N 0.000 claims 2
- 101150072608 CVC1 gene Proteins 0.000 claims 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 2
- 229920001690 polydopamine Polymers 0.000 claims 2
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- PHZFJRZBZBRNFK-UHFFFAOYSA-N 1,1'-biphenyl;9h-fluorene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C1=CC=C2CC3=CC=CC=C3C2=C1 PHZFJRZBZBRNFK-UHFFFAOYSA-N 0.000 claims 1
- YBQZXXMEJHZYMB-UHFFFAOYSA-N 1,2-diphenylhydrazine Chemical compound C=1C=CC=CC=1NNC1=CC=CC=C1 YBQZXXMEJHZYMB-UHFFFAOYSA-N 0.000 claims 1
- PGDARWFJWJKPLY-UHFFFAOYSA-N 4-[2-[3-[4-(diethylamino)phenyl]-2-phenyl-1,3-dihydropyrazol-5-yl]ethenyl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C=CC1=CC(C=2C=CC(=CC=2)N(CC)CC)N(C=2C=CC=CC=2)N1 PGDARWFJWJKPLY-UHFFFAOYSA-N 0.000 claims 1
- XTOMFMNDPPZOCN-UHFFFAOYSA-N C1(=CC=CC=C1)NNC1=CC=CC=C1.C(C)N(C1=CC=C(C=O)C=C1)CC Chemical compound C1(=CC=CC=C1)NNC1=CC=CC=C1.C(C)N(C1=CC=C(C=O)C=C1)CC XTOMFMNDPPZOCN-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 241000206607 Porphyra umbilicalis Species 0.000 claims 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000005110 aryl thio group Chemical group 0.000 claims 1
- 125000000732 arylene group Chemical group 0.000 claims 1
- BMHBMLLQKJESDS-UHFFFAOYSA-N benzene;formaldehyde Chemical group O=C.C1=CC=CC=C1 BMHBMLLQKJESDS-UHFFFAOYSA-N 0.000 claims 1
- XBWRJSSJWDOUSJ-UHFFFAOYSA-L chromium(ii) chloride Chemical compound Cl[Cr]Cl XBWRJSSJWDOUSJ-UHFFFAOYSA-L 0.000 claims 1
- 229910052748 manganese Inorganic materials 0.000 claims 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims 1
- CBHCDHNUZWWAPP-UHFFFAOYSA-N pecazine Chemical compound C1N(C)CCCC1CN1C2=CC=CC=C2SC2=CC=CC=C21 CBHCDHNUZWWAPP-UHFFFAOYSA-N 0.000 claims 1
- 229920006389 polyphenyl polymer Polymers 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 abstract description 5
- 229910052740 iodine Inorganic materials 0.000 abstract description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 abstract description 3
- 239000010410 layer Substances 0.000 description 126
- 239000000463 material Substances 0.000 description 42
- 239000002585 base Substances 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 238000000034 method Methods 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 238000002347 injection Methods 0.000 description 11
- 239000007924 injection Substances 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000005229 chemical vapour deposition Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000004528 spin coating Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 125000002541 furyl group Chemical group 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 125000001544 thienyl group Chemical group 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 5
- 238000005240 physical vapour deposition Methods 0.000 description 5
- 238000007639 printing Methods 0.000 description 5
- 238000005215 recombination Methods 0.000 description 5
- 230000006798 recombination Effects 0.000 description 5
- 241000894007 species Species 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 229910052762 osmium Inorganic materials 0.000 description 4
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 125000000547 substituted alkyl group Chemical group 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 150000003573 thiols Chemical group 0.000 description 4
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
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- 238000007641 inkjet printing Methods 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 238000000059 patterning Methods 0.000 description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 239000011135 tin Substances 0.000 description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- MVVGSPCXHRFDDR-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)phenol Chemical compound OC1=CC=CC=C1C1=NC2=CC=CC=C2S1 MVVGSPCXHRFDDR-UHFFFAOYSA-N 0.000 description 2
- GHGZVWOTJDLREY-UHFFFAOYSA-N 2-(1,3-benzoxazol-2-yl)phenol Chemical compound OC1=CC=CC=C1C1=NC2=CC=CC=C2O1 GHGZVWOTJDLREY-UHFFFAOYSA-N 0.000 description 2
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 description 2
- DHLFXZQEAWYQLC-UHFFFAOYSA-N 4-(dimethylamino)-2-nitrobenzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C([N+]([O-])=O)=C1 DHLFXZQEAWYQLC-UHFFFAOYSA-N 0.000 description 2
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 125000000041 C6-C10 aryl group Chemical group 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
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- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
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- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
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- 238000007740 vapor deposition Methods 0.000 description 1
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Classifications
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- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
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- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
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- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07102336 | 2007-02-14 | ||
| EP07107611 | 2007-05-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW200848412A true TW200848412A (en) | 2008-12-16 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW097104992A TW200848412A (en) | 2007-02-14 | 2008-02-13 | Electroluminescent metal complex |
Country Status (7)
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| US (1) | US9284278B2 (enExample) |
| EP (1) | EP2139907B1 (enExample) |
| JP (1) | JP5606075B2 (enExample) |
| KR (1) | KR101516441B1 (enExample) |
| CN (1) | CN101652375B (enExample) |
| TW (1) | TW200848412A (enExample) |
| WO (1) | WO2008098851A1 (enExample) |
Families Citing this family (8)
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| KR101539789B1 (ko) * | 2007-06-22 | 2015-07-27 | 바스프 에스이 | 발광 ｃｕ(ｉ) 착물 |
| US8324385B2 (en) | 2008-10-30 | 2012-12-04 | Madrigal Pharmaceuticals, Inc. | Diacylglycerol acyltransferase inhibitors |
| US8530687B2 (en) | 2010-09-07 | 2013-09-10 | University Of Florida Research Foundation, Inc. | Catalysts, methods of making catalysts, and methods of use |
| EP2991997B1 (en) | 2013-04-29 | 2018-02-21 | UDC Ireland Limited | Transition metal complexes with carbene ligands and the use thereof in oleds |
| KR102079250B1 (ko) | 2013-05-02 | 2020-02-20 | 삼성디스플레이 주식회사 | 유기금속 화합물 및 이를 포함한 유기 발광 소자 |
| WO2019194220A1 (ja) * | 2018-04-06 | 2019-10-10 | 日本曹達株式会社 | （ヘテロ）アリールスルホンアミド化合物および有害生物防除剤 |
| CN112079875B (zh) * | 2020-09-07 | 2023-04-18 | 奥来德(上海)光电材料科技有限公司 | 一种有机电致发光材料及其制备方法和有机电致发光器件 |
| CN114591264A (zh) * | 2020-12-04 | 2022-06-07 | 湖南超亟检测技术有限责任公司 | 一种指示pH值的荧光探针及其制备方法和应用 |
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| NL7109150A (enExample) * | 1970-07-06 | 1972-01-10 | ||
| CZ302691B6 (cs) * | 1998-07-08 | 2011-09-07 | Sanofi - Aventis Deutschland GmbH | N-Arylamidová sloucenina, zpusob její prípravy, farmaceutický prostredek tuto slouceninu obsahující, tato sloucenina pro použití jako aktivátor a pro použití k terapii nebo profylaxi |
| JP2000355687A (ja) * | 1999-04-15 | 2000-12-26 | Fuji Photo Film Co Ltd | 新規アゾール誘導体、発光素子材料およびそれを使用した発光素子 |
| JP3968966B2 (ja) * | 1999-07-05 | 2007-08-29 | 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 |
| US6420057B1 (en) * | 1999-07-05 | 2002-07-16 | Konica Corporation | Organic electroluminescent element |
| JP5278983B2 (ja) * | 1999-11-17 | 2013-09-04 | 塩野義製薬株式会社 | アミド化合物の新規用途 |
| US6790540B2 (en) * | 2000-06-01 | 2004-09-14 | Nippon Steel Chemical Co., Ltd. | Organic electroluminescent element material and organic electroluminescent element |
| CA2413086C (en) * | 2000-06-21 | 2011-06-28 | Alexander Alanine | Benzothiazole derivatives |
| JP3949391B2 (ja) | 2001-05-14 | 2007-07-25 | 富士フイルム株式会社 | 発光素子 |
| US7119112B2 (en) | 2002-02-28 | 2006-10-10 | Icagen, Inc. | Sulfonamides as potassium channel blockers |
| JP3963811B2 (ja) * | 2002-09-30 | 2007-08-22 | 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 |
| EP1680431A1 (en) | 2003-10-17 | 2006-07-19 | Rigel Pharmaceuticals, Inc. | Benzothiazole and thiazole'5,5-b!pyridine compositions and their use as ubiquitin ligase inhibitors |
| CN101379559A (zh) * | 2004-05-05 | 2009-03-04 | 西巴特殊化学品控股有限公司 | 金属螯合物以及其在高存储能力的光记录介质中的应用 |
| EP1893718B1 (en) * | 2004-06-28 | 2018-10-03 | UDC Ireland Limited | Electroluminescent metal complexes with triazoles and benotriazoles |
| JP2006152101A (ja) * | 2004-11-29 | 2006-06-15 | 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 |
| EP1841834B1 (en) * | 2004-12-23 | 2009-05-06 | Ciba Holding Inc. | Electroluminescent metal complexes with nucleophilic carbene ligands |
| JP2007099962A (ja) * | 2005-10-06 | 2007-04-19 | 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 |
| JP5234965B2 (ja) * | 2005-12-28 | 2013-07-10 | チバ ホールディング インコーポレーテッド | トリアゾールとのエレクトロルミネセンス金属錯体 |
-
2008
- 2008-02-04 US US12/526,069 patent/US9284278B2/en active Active
- 2008-02-04 KR KR1020097019035A patent/KR101516441B1/ko active Active
- 2008-02-04 CN CN200880005175.4A patent/CN101652375B/zh active Active
- 2008-02-04 JP JP2009549393A patent/JP5606075B2/ja active Active
- 2008-02-04 EP EP08708612.0A patent/EP2139907B1/en active Active
- 2008-02-04 WO PCT/EP2008/051308 patent/WO2008098851A1/en not_active Ceased
- 2008-02-13 TW TW097104992A patent/TW200848412A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2010518136A (ja) | 2010-05-27 |
| EP2139907A1 (en) | 2010-01-06 |
| US20100044688A1 (en) | 2010-02-25 |
| CN101652375B (zh) | 2016-08-24 |
| JP5606075B2 (ja) | 2014-10-15 |
| EP2139907B1 (en) | 2013-08-14 |
| US9284278B2 (en) | 2016-03-15 |
| CN101652375A (zh) | 2010-02-17 |
| KR101516441B1 (ko) | 2015-05-07 |
| WO2008098851A1 (en) | 2008-08-21 |
| KR20090109591A (ko) | 2009-10-20 |
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