KR100729737B1 - 금속 화합물 및 이를 포함하는 유기 전계 발광 소자 - Google Patents
금속 화합물 및 이를 포함하는 유기 전계 발광 소자 Download PDFInfo
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- KR100729737B1 KR100729737B1 KR1020060001727A KR20060001727A KR100729737B1 KR 100729737 B1 KR100729737 B1 KR 100729737B1 KR 1020060001727 A KR1020060001727 A KR 1020060001727A KR 20060001727 A KR20060001727 A KR 20060001727A KR 100729737 B1 KR100729737 B1 KR 100729737B1
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- 238000005401 electroluminescence Methods 0.000 title description 2
- 229910000765 intermetallic Inorganic materials 0.000 title 1
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 19
- 125000005843 halogen group Chemical group 0.000 claims abstract description 17
- 125000001424 substituent group Chemical group 0.000 claims abstract description 17
- 125000003118 aryl group Chemical group 0.000 claims abstract description 9
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 9
- -1 acetylenyl group Chemical group 0.000 claims abstract description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 8
- 150000002736 metal compounds Chemical class 0.000 claims abstract description 8
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 5
- 229910052741 iridium Inorganic materials 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 5
- 229910052762 osmium Inorganic materials 0.000 claims abstract description 3
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 3
- 229910052702 rhenium Inorganic materials 0.000 claims abstract description 3
- 229910052703 rhodium Inorganic materials 0.000 claims abstract description 3
- 229910052711 selenium Inorganic materials 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- 229910052727 yttrium Inorganic materials 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 4
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 abstract 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 80
- 230000015572 biosynthetic process Effects 0.000 description 61
- 238000003786 synthesis reaction Methods 0.000 description 61
- 238000006243 chemical reaction Methods 0.000 description 50
- 239000012299 nitrogen atmosphere Substances 0.000 description 49
- 239000011541 reaction mixture Substances 0.000 description 47
- 238000004440 column chromatography Methods 0.000 description 45
- 239000000706 filtrate Substances 0.000 description 40
- 229910000027 potassium carbonate Inorganic materials 0.000 description 40
- 238000010992 reflux Methods 0.000 description 40
- 239000000203 mixture Substances 0.000 description 25
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 24
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 16
- 239000002002 slurry Substances 0.000 description 16
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 16
- 239000000463 material Substances 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 14
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- SHXHPUAKLCCLDV-UHFFFAOYSA-N 1,1,1-trifluoropentane-2,4-dione Chemical compound CC(=O)CC(=O)C(F)(F)F SHXHPUAKLCCLDV-UHFFFAOYSA-N 0.000 description 8
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 8
- 229940093475 2-ethoxyethanol Drugs 0.000 description 8
- RVSSIWMPYJUUFJ-UHFFFAOYSA-N 5-(dimethylamino)pyridine-2-carboxylic acid Chemical compound CN(C)C1=CC=C(C(O)=O)N=C1 RVSSIWMPYJUUFJ-UHFFFAOYSA-N 0.000 description 8
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 230000020169 heat generation Effects 0.000 description 8
- QAMFBRUWYYMMGJ-UHFFFAOYSA-N hexafluoroacetylacetone Chemical compound FC(F)(F)C(=O)CC(=O)C(F)(F)F QAMFBRUWYYMMGJ-UHFFFAOYSA-N 0.000 description 8
- 239000003446 ligand Substances 0.000 description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 8
- 229940081066 picolinic acid Drugs 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000011592 zinc chloride Substances 0.000 description 8
- 235000005074 zinc chloride Nutrition 0.000 description 8
- QNDGTSQNWUXVEA-UHFFFAOYSA-N 4-chloro-1,3-benzoxazole Chemical compound ClC1=CC=CC2=C1N=CO2 QNDGTSQNWUXVEA-UHFFFAOYSA-N 0.000 description 5
- 230000005525 hole transport Effects 0.000 description 5
- 150000003623 transition metal compounds Chemical class 0.000 description 5
- IFEPGHPDQJOYGG-UHFFFAOYSA-N 4-chloro-1,3-benzothiazole Chemical class ClC1=CC=CC2=C1N=CS2 IFEPGHPDQJOYGG-UHFFFAOYSA-N 0.000 description 4
- 150000003624 transition metals Chemical group 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 2
- 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 2
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 2
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 2
- 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
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 2
- 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 2
- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 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
- 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 2
- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 2
- ZYZCALPXKGUGJI-DDVDASKDSA-M (e,3r,5s)-7-[3-(4-fluorophenyl)-2-phenyl-5-propan-2-ylimidazol-4-yl]-3,5-dihydroxyhept-6-enoate Chemical compound C=1C=C(F)C=CC=1N1C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C(C(C)C)N=C1C1=CC=CC=C1 ZYZCALPXKGUGJI-DDVDASKDSA-M 0.000 description 2
- 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 2
- 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 2
- 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 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
- ZBTMRBYMKUEVEU-UHFFFAOYSA-N 1-bromo-4-methylbenzene Chemical compound CC1=CC=C(Br)C=C1 ZBTMRBYMKUEVEU-UHFFFAOYSA-N 0.000 description 2
- 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 2
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 2
- 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 2
- 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 2
- GAACTGUSQIEVLX-UHFFFAOYSA-N 4-(4-methylphenyl)-1,3-benzothiazole Chemical compound C1=CC(C)=CC=C1C1=CC=CC2=C1N=CS2 GAACTGUSQIEVLX-UHFFFAOYSA-N 0.000 description 2
- HPZHWXDNBQMYSM-UHFFFAOYSA-N 4-(4-methylphenyl)-1,3-benzoxazole Chemical compound C1=CC(C)=CC=C1C1=CC=CC2=C1N=CO2 HPZHWXDNBQMYSM-UHFFFAOYSA-N 0.000 description 2
- KVDVBHKCRWZPRC-UHFFFAOYSA-N 4-[4-(1,1,1,3,3,3-hexafluoropropan-2-yl)phenyl]-1,3-benzothiazole Chemical compound C1=CC(C(C(F)(F)F)C(F)(F)F)=CC=C1C1=CC=CC2=C1N=CS2 KVDVBHKCRWZPRC-UHFFFAOYSA-N 0.000 description 2
- FZTOESCXYUOLHU-UHFFFAOYSA-N 4-[4-(1,1,1,3,3,3-hexafluoropropan-2-yl)phenyl]-1,3-benzoxazole Chemical compound C1=CC(C(C(F)(F)F)C(F)(F)F)=CC=C1C1=CC=CC2=C1N=CO2 FZTOESCXYUOLHU-UHFFFAOYSA-N 0.000 description 2
- PLZPKFNKGVCVPS-UHFFFAOYSA-N 4-[4-(trifluoromethyl)phenyl]-1,3-benzothiazole Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC2=C1N=CS2 PLZPKFNKGVCVPS-UHFFFAOYSA-N 0.000 description 2
- RILRYAJSOCTFBV-UHFFFAOYSA-N 4-phenyl-1,3-benzothiazole Chemical compound C1=CC=C2SC=NC2=C1C1=CC=CC=C1 RILRYAJSOCTFBV-UHFFFAOYSA-N 0.000 description 2
- JJOWJPHHDSCECU-UHFFFAOYSA-N 4-phenyl-1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1C1=CC=CC=C1 JJOWJPHHDSCECU-UHFFFAOYSA-N 0.000 description 2
- ISMDILRWKSYCOD-GNKBHMEESA-N C(C1=CC=CC=C1)[C@@H]1NC(OCCCCCCCCCCCNC([C@@H](NC(C[C@@H]1O)=O)C(C)C)=O)=O Chemical compound C(C1=CC=CC=C1)[C@@H]1NC(OCCCCCCCCCCCNC([C@@H](NC(C[C@@H]1O)=O)C(C)C)=O)=O ISMDILRWKSYCOD-GNKBHMEESA-N 0.000 description 2
- KCBAMQOKOLXLOX-BSZYMOERSA-N CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O Chemical compound CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O KCBAMQOKOLXLOX-BSZYMOERSA-N 0.000 description 2
- 229940126657 Compound 17 Drugs 0.000 description 2
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- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
상기 화학식 3에서 * 표시된 부분과 전이 금속 M은 공유결합하고, 인접의 N 또는 P와 배위결합을 통해 착화합물을 이룬다. 상기 화학식 4 및 5에서 Z 및 W는 서로 같거나 다르며, 각각 O, N, S 및 P에서 선택된 헤테로 원자이다. 화학식 3, 4 및 5에서 R15~R28 는 서로 같거나 다르며, 각각 수소, 탄소수 1~20의 알킬, 아릴, 사이클로알킬, 할로겐기, 하나 이상의 할로겐 원자를 함유하는 선형 또는 가지형 치환기; 하나 이상의 헤테로 원자를 함유하고 있는 선형 또는 가지형 치환기; 카보닐기; 바이닐기; 아세틸레닐기에서 선택되며, 고리를 이루는 형태를 포함한다.
대표적인 리간드의 예들은 하기의 화학식 6 와 같다.
[화학식 6]
상기 화학식 중 전이금속 화합물은 대표적인 하기와 같은 합성과정을 통해 합성할 수 있는데, 반응식 1과 2는 리간드 합성을 나타내며, 반응식 3은 메탈레이션(metalation)과정을 설명하였다.
[반응식 1]
대표적인 메탈레이션(Metalation) 반응인 상기 반응식 3에서 보는 바와 같이 페닐렌 벤조옥사졸 유도체와 수화된 삼염화 이리듐을 질소대기 하에서 반응시키면 두개의 이리듐 금속이 Cl 리간드를 서로 공유하는 다이머(dimer) 형태의 중간체를 쉽게 제조할 수 있으며, 이 중간체는 약염기가 포함된 용매 중에서 보조리간드와 반응하여 화학식 1의 전이금속화합물을 형성한다.
[실시예 1]
[실시예 2]
[실시예 3]
[실시예 4]
[실시예 5]
[실시예 6]
[실시예 7]
[실시예 8]
[실시예 9]
[실시예 10]
[실시예 11]
[실시예 12]
[실시예 13]
[실시예 14]
[실시예 15]
[실시예 16]
[실시예 17]
[실시예 18]
[실시예 19]
[실시예 20]
[실시예 21]
[실시예 22]
[실시예 23]
[실시예 24]
[실시예 25]
[실시예 26]
[실시예 27]
[실시예 28]
[실시예 29]
[실시예 30]
[실시예 31]
[실시예 32]
[실시예 33]
[실시예 34]
[실시예 35]
[실시예 36]
[실시예 37]
[실시예 38]
[실시예 40]
상기 과정에 따라 얻은 화합물의 PL 스펙트럼을 조사하였고, 그 결과는 하기 표 1에 나타난 바와 같다.
[표 1]
화합물 | 수율 | PL(nm) | 화합물 | PL(nm) | |
화합물1 | 88% | 579 | 화합물21 | 90% | 558 |
화합물2 | 91% | 573 | 화합물22 | 89% | 552 |
화합물3 | 89% | 570 | 화합물23 | 90% | 551 |
화합물4 | 87% | 576 | 화합물24 | 91% | 554 |
화합물5 | 88% | 572 | 화합물25 | 93% | 551 |
화합물6 | 90% | 602 | 화합물26 | 92% | 547 |
화합물7 | 92% | 595 | 화합물27 | 85% | 544 |
화합물8 | 88% | 593 | 화합물28 | 87% | 541 |
화합물9 | 87% | 596 | 화합물29 | 90% | 545 |
화합물10 | 89% | 594 | 화합물30 | 92% | 540 |
화합물11 | 90% | 582 | 화합물31 | 85% | 604 |
화합물12 | 92% | 579 | 화합물32 | 89% | 595 |
화합물13 | 91% | 577 | 화합물33 | 87% | 594 |
화합물14 | 91% | 579 | 화합물34 | 92% | 597 |
화합물15 | 90% | 575 | 화합물35 | 91% | 594 |
화합물16 | 88% | 569 | 화합물36 | 84% | 579 |
화합물17 | 84% | 562 | 화합물37 | 81% | 574 |
화합물18 | 83% | 561 | 화합물38 | 82% | 571 |
화합물19 | 85% | 564 | 화합물39 | 92% | 577 |
화합물20 | 89% | 561 | 화합물40 | 88% | 572 |
[실시예 41]
Claims (2)
- 하기 화학식 1:[화학식 1]로 표현되며,여기서 M은 Ir, Pt, Rh, Re 및 Os에서 선택된 하나이고, m은 2 또는 3이고, n은 0 또는 1이며, m과 n의 합은 3이고, 단 M이 Pt 일 때 m과 n의 합은 2이고, X는 N 또는 P이며, Y 는 O, S 및 Se에서 선택된 하나이고,[화학식 2]로 표현되는 구조식에서 선택된 하나이고,상기 화학식 2에서 * 표시 부분과 인접 방향족 부분이 공유 결합하며,상기 화학식 1에서의 M은 화학식 2에서 a로 표시된 부분과 공유결합하고 상기 화학식 1에서의 X 부분과 배위 결합하며,상기 R1~R3 및 R5~R14는 서로 같거나 다르며, 각각 수소, 탄소 수 1~20의 알킬, 아릴, 사이클로알킬, 할로겐기, 하나 이상의 할로겐원자를 함유하는 선형 또는 가지형 치환기, 하나 이상의 헤테로 원자를 함유하고 있는 선형 또는 가지형 치환기, 카보닐기, 바이닐기, 아세틸레닐기에서 선택되며, 고리를 이루는 형태를 포함하며,상기 R4 는 수소, 방향족 고리 치환체를 제외한 탄소수 1~20의 알킬, 사이클로알킬, 할로겐기, 하나 이상의 할로겐원자를 함유하는 선형 또는 가지형 치환기, 하나 이상의 헤테로 원자를 함유하고 있는 선형 또는 가지형 치환기이고,상기 화학식 1에서 L2는 하기의 화학식 3, 4, 5:[화학식 3][화학식 4] [화학식 5]로 표현되는 구조식에서 선택된 하나이고,상기 화학식 3에서 * 로 표시된 부분과 상기 화학식 1에서 M은 공유결합하고, 인접의 N 또는 P와 배위 결합을 통해 착화합물을 이루고,상기 화학식 4 및 5에서 Z 및 W는 서로 같거나 다르며 각각 O, N, S 및 P에서 선택되며,상기 화학식 3, 4 및 5에서 상기 R15~R28 는 서로 같거나 다르며, 각각 수소, 탄소수 1~20의 알킬, 아릴, 사이클로알킬, 할로겐기, 하나 이상의 할로겐 원자를 함유하는 선형 또는 가지형 치환기, 하나 이상의 헤테로 원자를 함유하고 있는 선형 또는 가지형 치환기, 카보닐기, 바이닐기, 아세틸레닐기에서 선택되며, 고리를 이루는 형태를 포함하는금속 화합물.
- 제1항에 따른 금속 화합물을 포함하는 유기 전계 발광 소자.
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US11/913,192 US7939669B2 (en) | 2006-01-06 | 2007-01-08 | Metallic compound and organic electroluminescence device comprising the same |
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KR20190068676A (ko) * | 2017-12-08 | 2019-06-19 | 삼성디스플레이 주식회사 | 유기 전계 발광 소자 및 유기 전계 발광 소자용 유기 금속 착물 |
KR20190095308A (ko) * | 2016-12-21 | 2019-08-14 | 고쿠리쓰다이가쿠호진 규슈다이가쿠 | 발광 재료, 화합물 및 유기 발광 소자 |
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