KR20150137265A - An electroluminescent compound and an electroluminescent device comprising the same - Google Patents
An electroluminescent compound and an electroluminescent device comprising the same Download PDFInfo
- Publication number
- KR20150137265A KR20150137265A KR1020140064831A KR20140064831A KR20150137265A KR 20150137265 A KR20150137265 A KR 20150137265A KR 1020140064831 A KR1020140064831 A KR 1020140064831A KR 20140064831 A KR20140064831 A KR 20140064831A KR 20150137265 A KR20150137265 A KR 20150137265A
- Authority
- KR
- South Korea
- Prior art keywords
- group
- substituted
- unsubstituted
- carbon atoms
- layer
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 65
- 239000000126 substance Substances 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 48
- -1 ester group compound Chemical class 0.000 claims description 47
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 239000011368 organic material Substances 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000003367 polycyclic group Chemical group 0.000 claims description 12
- 238000002347 injection Methods 0.000 claims description 10
- 239000007924 injection Substances 0.000 claims description 10
- 125000002723 alicyclic group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000005264 aryl amine group Chemical group 0.000 claims description 7
- 125000005549 heteroarylene group Chemical group 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 150000001721 carbon Chemical class 0.000 claims description 6
- 239000002019 doping agent Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 3
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000000732 arylene group Chemical group 0.000 claims description 3
- 229910052805 deuterium Inorganic materials 0.000 claims description 3
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 2
- 125000006746 (C1-C60) alkoxy group Chemical group 0.000 claims description 2
- 125000006743 (C1-C60) alkyl group Chemical group 0.000 claims description 2
- 125000006818 (C3-C60) cycloalkyl group Chemical group 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000004419 alkynylene group Chemical group 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 125000005104 aryl silyl group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000001033 ether group Chemical group 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical group [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 claims description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims 1
- 125000000962 organic group Chemical group 0.000 claims 1
- 229910052711 selenium Inorganic materials 0.000 claims 1
- 229910052714 tellurium Inorganic materials 0.000 claims 1
- 239000010410 layer Substances 0.000 description 124
- 230000015572 biosynthetic process Effects 0.000 description 65
- 238000003786 synthesis reaction Methods 0.000 description 65
- 239000000463 material Substances 0.000 description 43
- 238000004519 manufacturing process Methods 0.000 description 42
- 238000005160 1H NMR spectroscopy Methods 0.000 description 15
- 239000000758 substrate Substances 0.000 description 15
- 230000032258 transport Effects 0.000 description 10
- 229940125904 compound 1 Drugs 0.000 description 7
- 238000000151 deposition Methods 0.000 description 7
- 230000005525 hole transport Effects 0.000 description 7
- 238000005401 electroluminescence Methods 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 230000008021 deposition Effects 0.000 description 5
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 5
- 125000002950 monocyclic group Chemical group 0.000 description 5
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 4
- FIHILUSWISKVSR-UHFFFAOYSA-N 3,6-dibromo-9h-carbazole Chemical compound C1=C(Br)C=C2C3=CC(Br)=CC=C3NC2=C1 FIHILUSWISKVSR-UHFFFAOYSA-N 0.000 description 4
- QOVYHDHLFPKQQG-NDEPHWFRSA-N N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O Chemical compound N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O QOVYHDHLFPKQQG-NDEPHWFRSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 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
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- 229940126657 Compound 17 Drugs 0.000 description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 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
- 239000010406 cathode material Substances 0.000 description 3
- 229940126543 compound 14 Drugs 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 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
- GCTFTMWXZFLTRR-GFCCVEGCSA-N (2r)-2-amino-n-[3-(difluoromethoxy)-4-(1,3-oxazol-5-yl)phenyl]-4-methylpentanamide Chemical compound FC(F)OC1=CC(NC(=O)[C@H](N)CC(C)C)=CC=C1C1=CN=CO1 GCTFTMWXZFLTRR-GFCCVEGCSA-N 0.000 description 2
- UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 description 2
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 2
- SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 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
- 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
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical group C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- 125000005979 2-naphthyloxy group Chemical group 0.000 description 2
- JEYLGFCAZBGCMC-UHFFFAOYSA-N 3-(4-bromophenyl)-9-phenylcarbazole Chemical compound C1=CC(Br)=CC=C1C1=CC=C(N(C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 JEYLGFCAZBGCMC-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- YHIWBVHIGCRVLE-UHFFFAOYSA-N 3-bromo-1h-indole Chemical compound C1=CC=C2C(Br)=CNC2=C1 YHIWBVHIGCRVLE-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
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000005332 alkyl sulfoxy group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
- 150000003974 aralkylamines Chemical group 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000005165 aryl thioxy group Chemical group 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 2
- 229940126142 compound 16 Drugs 0.000 description 2
- 229940125877 compound 31 Drugs 0.000 description 2
- 229940125936 compound 42 Drugs 0.000 description 2
- 229940125900 compound 59 Drugs 0.000 description 2
- BJXYHBKEQFQVES-NWDGAFQWSA-N enpatoran Chemical compound N[C@H]1CN(C[C@H](C1)C(F)(F)F)C1=C2C=CC=NC2=C(C=C1)C#N BJXYHBKEQFQVES-NWDGAFQWSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 239000007773 negative electrode material Substances 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- YWDUZLFWHVQCHY-UHFFFAOYSA-N 1,3,5-tribromobenzene Chemical compound BrC1=CC(Br)=CC(Br)=C1 YWDUZLFWHVQCHY-UHFFFAOYSA-N 0.000 description 1
- 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 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- FNKCOUREFBNNHG-UHFFFAOYSA-N 1,3-dibromo-5-chlorobenzene Chemical compound ClC1=CC(Br)=CC(Br)=C1 FNKCOUREFBNNHG-UHFFFAOYSA-N 0.000 description 1
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 description 1
- KEURHSDOWCBXFX-UHFFFAOYSA-N 1-(2-bromophenyl)-2-nitrobenzene Chemical group [O-][N+](=O)C1=CC=CC=C1C1=CC=CC=C1Br KEURHSDOWCBXFX-UHFFFAOYSA-N 0.000 description 1
- GCXKAMCPXWZWGS-UHFFFAOYSA-N 1-(4-bromophenyl)-3,5-dichlorobenzene Chemical group ClC1=CC(Cl)=CC(C=2C=CC(Br)=CC=2)=C1 GCXKAMCPXWZWGS-UHFFFAOYSA-N 0.000 description 1
- INRKYQLNSZXVTC-UHFFFAOYSA-N 1-(4-bromophenyl)dibenzothiophene Chemical compound BrC1=CC=C(C=C1)C1=CC=CC=2SC3=C(C=21)C=CC=C3 INRKYQLNSZXVTC-UHFFFAOYSA-N 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- DZHFFMWJXJBBRG-UHFFFAOYSA-N 1-bromo-3,5-dichlorobenzene Chemical compound ClC1=CC(Cl)=CC(Br)=C1 DZHFFMWJXJBBRG-UHFFFAOYSA-N 0.000 description 1
- JESBGFNZNSEZMR-UHFFFAOYSA-N 1-bromodibenzothiophene Chemical compound S1C2=CC=CC=C2C2=C1C=CC=C2Br JESBGFNZNSEZMR-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical group C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 1
- WZYVDGDZBNQVCF-UHFFFAOYSA-N 2,4,6-tris(4-bromophenyl)-1,3,5-triazine Chemical compound C1=CC(Br)=CC=C1C1=NC(C=2C=CC(Br)=CC=2)=NC(C=2C=CC(Br)=CC=2)=N1 WZYVDGDZBNQVCF-UHFFFAOYSA-N 0.000 description 1
- BQMVEDWWKBFYJC-UHFFFAOYSA-N 2,4-dibromo-6-chloro-1,3,5-triazine Chemical compound ClC1=NC(=NC(=N1)Br)Br BQMVEDWWKBFYJC-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- WONYVCKUEUULQN-UHFFFAOYSA-N 2-methyl-n-(2-methylphenyl)aniline Chemical group CC1=CC=CC=C1NC1=CC=CC=C1C WONYVCKUEUULQN-UHFFFAOYSA-N 0.000 description 1
- JTMODJXOTWYBOZ-UHFFFAOYSA-N 2-methyl-n-phenylaniline Chemical group CC1=CC=CC=C1NC1=CC=CC=C1 JTMODJXOTWYBOZ-UHFFFAOYSA-N 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- DWYHDSLIWMUSOO-UHFFFAOYSA-N 2-phenyl-1h-benzimidazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2N1 DWYHDSLIWMUSOO-UHFFFAOYSA-N 0.000 description 1
- MUKXTNPYJPZHHI-UHFFFAOYSA-N 2-phenyl-1h-imidazo[4,5-d]pyridazine Chemical compound C1=CC=CC=C1C1=NC2=CN=NC=C2N1 MUKXTNPYJPZHHI-UHFFFAOYSA-N 0.000 description 1
- 125000006607 3,3-dimethylbutyloxy group Chemical group 0.000 description 1
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 1
- DYTMTLPTFUWUSO-UHFFFAOYSA-N 3-bromo-5-chloro-1h-indole Chemical compound ClC1=CC=C2NC=C(Br)C2=C1 DYTMTLPTFUWUSO-UHFFFAOYSA-N 0.000 description 1
- LTBWKAYPXIIVPC-UHFFFAOYSA-N 3-bromo-9h-carbazole Chemical compound C1=CC=C2C3=CC(Br)=CC=C3NC2=C1 LTBWKAYPXIIVPC-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical group CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 1
- FIAXBPCUAUSGJH-UHFFFAOYSA-N 4-(4-bromophenyl)dibenzothiophene Chemical compound C1=CC(Br)=CC=C1C1=CC=CC2=C1SC1=CC=CC=C21 FIAXBPCUAUSGJH-UHFFFAOYSA-N 0.000 description 1
- MQFYUZCANYLWEI-UHFFFAOYSA-N 4-methylnaphthalen-1-amine Chemical group C1=CC=C2C(C)=CC=C(N)C2=C1 MQFYUZCANYLWEI-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- XSDKKRKTDZMKCH-UHFFFAOYSA-N 9-(4-bromophenyl)carbazole Chemical compound C1=CC(Br)=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 XSDKKRKTDZMKCH-UHFFFAOYSA-N 0.000 description 1
- GZSUIHUAFPHZSU-UHFFFAOYSA-N 9-ethyl-2,3-dihydro-1h-carbazol-4-one Chemical compound C12=CC=CC=C2N(CC)C2=C1C(=O)CCC2 GZSUIHUAFPHZSU-UHFFFAOYSA-N 0.000 description 1
- QXDWMAODKPOTKK-UHFFFAOYSA-N 9-methylanthracen-1-amine Chemical group C1=CC(N)=C2C(C)=C(C=CC=C3)C3=CC2=C1 QXDWMAODKPOTKK-UHFFFAOYSA-N 0.000 description 1
- WGUUKVJNVYAFFI-UHFFFAOYSA-N 9h-carbazol-3-ylboronic acid Chemical compound C1=CC=C2C3=CC(B(O)O)=CC=C3NC2=C1 WGUUKVJNVYAFFI-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical group C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 1
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 1
- 101150003085 Pdcl gene Proteins 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- JBIZULNJEBTYOY-UHFFFAOYSA-N [2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]boronic acid Chemical compound C1(=CC=CC=C1)C1=NC(=NC(=N1)C1=CC=CC=C1)C1=C(C=CC=C1)B(O)O JBIZULNJEBTYOY-UHFFFAOYSA-N 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- YUENFNPLGJCNRB-UHFFFAOYSA-N anthracen-1-amine Chemical group C1=CC=C2C=C3C(N)=CC=CC3=CC2=C1 YUENFNPLGJCNRB-UHFFFAOYSA-N 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical group C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 125000006616 biphenylamine group Chemical group 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PHHHJXDXNMUSAB-UHFFFAOYSA-N c([n](c1ccccc11)-c2ccccc2)c1-c(cc1c2c3ccc(-c(c4ccccc44)c[n]4-c4ccccc4)c2)ccc1[n]3-c(cc1)ccc1-c(cc1)cc(c2c3cccc2)c1[n]3-c1ccccc1 Chemical compound c([n](c1ccccc11)-c2ccccc2)c1-c(cc1c2c3ccc(-c(c4ccccc44)c[n]4-c4ccccc4)c2)ccc1[n]3-c(cc1)ccc1-c(cc1)cc(c2c3cccc2)c1[n]3-c1ccccc1 PHHHJXDXNMUSAB-UHFFFAOYSA-N 0.000 description 1
- ZRBFJAYTPGRLLL-UHFFFAOYSA-N c([n](c1ccccc11)-c2ccccc2)c1-c1ccc2[nH]c(ccc(-c(c3ccccc33)c[n]3-c3ccccc3)c3)c3c2c1 Chemical compound c([n](c1ccccc11)-c2ccccc2)c1-c1ccc2[nH]c(ccc(-c(c3ccccc33)c[n]3-c3ccccc3)c3)c3c2c1 ZRBFJAYTPGRLLL-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000005266 diarylamine group Chemical group 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical group C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005241 heteroarylamino group Chemical group 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000005921 isopentoxy group Chemical group 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- YGBMCLDVRUGXOV-UHFFFAOYSA-N n-[6-[6-chloro-5-[(4-fluorophenyl)sulfonylamino]pyridin-3-yl]-1,3-benzothiazol-2-yl]acetamide Chemical compound C1=C2SC(NC(=O)C)=NC2=CC=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=C(F)C=C1 YGBMCLDVRUGXOV-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000006608 n-octyloxy group Chemical group 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 description 1
- 125000005484 neopentoxy group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000003748 selenium group Chemical group *[Se]* 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000005649 substituted arylene group Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical group 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic Table
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
Description
본 발명은 유기발광 화합물에 관한 것으로서, 보다 구체적으로는 유기전계발광소자의 발광층 호스트 화합물로 채용되는 유기발광 화합물 및 이를 채용하여 장수명 및 발광 효율이 현저히 향상된 유기전계발광소자에 관한 것이다.The present invention relates to an organic light emitting compound, and more particularly, to an organic light emitting compound that is employed as a host compound of a light emitting layer of an organic electroluminescent device, and an organic electroluminescent device using the same.
유기전계발광소자는 투명 기판 위에도 소자를 형성할 수 있을 뿐 아니라, 플라즈마 디스플레이 패널(Plasma Display Panel)이나 무기 전계 발광(EL) 디스플레이에 비해 10 V 이하의 저전압 구동이 가능하고, 전력 소모가 비교적 적으며, 색감이 뛰어나다는 장점이 있고, 녹색, 청색, 적색의 3가지 색을 나타낼 수가 있어 최근에 차세대 디스플레이 소자로 많은 관심의 대상이 되고 있다.The organic electroluminescent device can not only form an element on a transparent substrate but also can operate at a low voltage of 10 V or less as compared with a plasma display panel (Plasma Display Panel) or an inorganic electroluminescence (EL) display, It has the advantage of excellent color and has three colors of green, blue, and red. It has recently become a subject of interest as a next generation display device.
다만, 이러한 유기전계발광소자가 상기와 같은 특징으로 발휘하기 위해서는 소자 내 유기층을 이루는 물질인 정공주입 물질, 정공수송 물질, 발광 물질, 전자수송 물질, 전자주입 물질 등이 안정하고 효율적인 재료에 의하여 뒷받침되는 것이 선행되어야 하나, 아직까지는 안정하고 효율적인 유기 전계발광 소자자용 유기물층 재료의 개발이 충분히 이루어지지 않은 상태이다. 따라서, 저전압 구동, 고효율 및 장수명을 갖는 새로운 재료의 개발이 계속 요구되고 있는 실정이다.However, in order for such an organic electroluminescent device to exhibit such characteristics, a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, and an electron injecting material, which are materials forming an organic layer in a device, However, until now, stable and efficient development of an organic layer material for an organic electroluminescence element has not been sufficiently developed yet. Therefore, there is a continuing demand for development of new materials having low-voltage driving, high efficiency and long life.
또한, 유기 발광 소자에서 발광효율을 결정하는 가장 중요한 요인은 발광 재료이다. 발광 재료로는 현재 형광 재료가 널리 사용되고 있으나, 발광 메커니즘 상 인광 재료의 개발이 이론적으로 발광 효율을 보다 개선시킬 수 있는 방법 중의 하나이고, 이에 따라 현재까지 다양한 인광 재료에 대해서 개발이 이루어지고 있으며, 특히 인광 발광 호스트 재료로는 현재까지 CBP가 가장 널리 알려져 있고, BALq 유도체를 호스트로 이용한 유기 발광 소자가 공지되어 있다.Further, the most important factor for determining the luminous efficiency in an organic light emitting device is a light emitting material. However, the development of a phosphorescent material on a light-emitting mechanism is one of the ways that the luminous efficiency can be improved more theoretically. Accordingly, a variety of phosphorescent materials have been developed to date, In particular, CBP is the most widely known phosphorescent host material, and an organic light emitting device using a BALq derivative as a host is known.
그러나, 인광 발광 재료를 사용한 유기 발광 소자는 형광 발광 재료를 사용한 소자에 비해 전류 효율이 상당히 높으나, 인광 발광 재료의 호스트로 BAlq, CBP 등의 재료를 사용할 경우, 형광재료를 사용한 소자에 비해 구동 전압이 높아서 전력 효율면에서 큰 이점이 없고, 또한, 소자의 수명 측면에서도 만족할만한 수준이 되질 못하여 더욱 안정적이고, 고성능의 호스트 재료의 개발이 요구되고 있다.However, in the case of using a material such as BAlq or CBP as a host of a phosphorescent material, the organic electroluminescent device using the phosphorescent material has a higher current efficiency than the device using the fluorescent material, There is no great advantage in terms of power efficiency, and the life of the device can not be satisfactory. Thus, development of a more stable and high-performance host material is required.
본 발명은 유기전계발광소자의 발광층에 채용되어 우수한 발광 특성을 구현할 수 있는 신규한 유기발광 화합물 및 이를 포함하는 유기전계발광소자를 제공하고자 한다.The present invention provides a novel organic light emitting compound and an organic electroluminescent device including the same that can be used in a light emitting layer of an organic electroluminescent device to realize excellent light emitting characteristics.
본 발명은 상기 과제를 해결하기 위하여, 하기 [화학식 1]로 표시되는 유기발광 화합물 및 이를 포함하는 유기전계발광소자를 제공한다.The present invention provides an organic light emitting compound represented by the following
[화학식 1][Chemical Formula 1]
상기 [화학식 1]에 따른 유기발광 화합물의 구체적인 구조 및 치환기에 대해서는 후술한다.The specific structure and substituent of the organic luminescent compound according to the
본 발명에 따른 유기발광 화합물은 구조 평판도가 우수하고, 높은 삼중항(triplet) 상태를 가져서 종래 인광 호스트 화합물에 비하여 보다 향상된 발광 효율과 장수명 특성의 구현이 가능하여 이를 채용한 유기전계발광소자는 다양한 디스플레이 소자에 유용하여 사용될 수 있다.The organic luminescent compound according to the present invention has excellent structure flatness and has a high triplet state, so that the luminescent efficiency and the longevity characteristics can be improved as compared with the conventional phosphorescent host compound, And can be used for display devices.
도 1 내지 5는 본 발명의 일 실시예에 따른 유기전계발광소자의 구조를 예시한 단면도이다.1 to 5 are cross-sectional views illustrating the structure of an organic electroluminescent device according to an embodiment of the present invention.
이하, 본 발명을 보다 구체적으로 설명한다.Hereinafter, the present invention will be described more specifically.
본 발명은 하기 [화학식 1]로 표시되는 신규한 유기발광 화합물에 관한 것이다.The present invention relates to a novel organic luminescent compound represented by the following formula (1).
[화학식 1][Chemical Formula 1]
상기 [화학식 1]에서,In the above formula (1)
X1은 CR2R3 또는 NR4이고, X2 내지 X4는 서로 동일하거나 상이하며, 각각 독립적으로 CR5 또는 N이다.X 1 is CR 2 R 3 or NR 4 , and X 2 to X 4 are the same or different and are each independently CR 5 or N;
R1 및 상기 R2 내지 R5는 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 30의 알킬기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기, 치환 또는 비치환된 탄소수 5 내지 50의 아릴기, 치환 또는 비치환된 탄소수 2 내지 50의 헤테로아릴기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬이 하나 이상 융합된 치환 또는 비치환된 탄소수 5 내지 50의 아릴기 및 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬이 하나 이상 융합된 치환 또는 비치환된 탄소수 2 내지 50의 헤테로아릴기 중에서 선택된다.R 1 and R 2 To R 5 each independently represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted carbon number A substituted or unsubstituted aryl group having 5 to 50 carbon atoms, and a substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms, wherein the substituted or unsubstituted C3 to C30 heteroaryl group, the substituted or unsubstituted C3 to C30 cycloalkyl, Is a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms.
L은 치환 또는 비치환된 탄소수 1 내지 30의 알킬렌기, 치환 또는 비치환된 탄소수 2 내지 30의 알케닐렌기, 치환 또는 비치환된 탄소수 2 내지 30의 알키닐렌기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬렌기, 치환 또는 비치환된 탄소수 5 내지 50의 아릴렌기, 치환 또는 비치환된 탄소수 2 내지 50의 헤테로아릴렌기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬이 하나 이상 융합된 치환 또는 비치환된 탄소수 5 내지 50의 아릴렌기 및 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬이 하나 이상 융합된 치환 또는 비치환된 탄소수 2 내지 50의 헤테로아릴렌기 중에서 선택된다.L is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted group having 2 to 30 carbon atoms A substituted or unsubstituted C2-C30 alkynylene group, a substituted or unsubstituted C3-C30 A substituted or unsubstituted C2 to C30 heteroarylene group, a substituted or unsubstituted C3 to C30 cycloalkyl, a substituted or unsubstituted C1 to C50 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, A substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms in which at least one unsubstituted or substituted unsubstituted arylene group having 5 to 50 carbon atoms and a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms is fused.
n, o 및 p는 각각 독립적으로 1 내지 3의 정수이고, 상기 n, o 및 p가 각각 2 이상인 경우 복수의 L, R1 및 [ ]는 각각 서로 동일하거나 상이할 수 있다.n, o and p are each independently an integer of 1 to 3, and when n, o and p are each 2 or more, a plurality of L, R 1 and [] may be the same or different from each other.
또한, 상기 L, R1 내지 R5 및 이들의 치환기는 서로 결합하거나 인접한 치환기와 연결되어 지환족, 방향족의 단일환 또는 다환 고리를 형성할 수 있으며, 상기 형성된 지환족, 방향족의 단일환 또는 다환 고리의 탄소원자는 N, S 및 O 중에서 선택되는 어느 하나 이상의 헤테로원자로 치환될 수 있다.The above-mentioned L, R < 1 > R 5 and the substituents thereof may be bonded to each other or may be connected with adjacent substituents to form a single alicyclic or aromatic ring or polycyclic ring, and the carbon atom of the alicyclic or aromatic monocyclic or polycyclic ring formed may be N, S, Lt; / RTI > may be substituted with any one or more heteroatoms selected from < RTI ID = 0.0 >
본 발명의 바람직한 구현예에 의하면, 상기 L은 각각 독립적으로 하기 [구조식 1] 중에서 선택될 수 있다.According to a preferred embodiment of the present invention, each L may independently be selected from the following [formula 1].
[구조식 1][Structural formula 1]
상기 [구조식 1]에서,In the
Z는 CR6, NR7, CR8R9, SiR10R11, GeR12R13, PR14, BR15, Te, O 및 S 중에서 선택되고, 상기 R6 내지 R15는 수소, 중수소, 할로겐기, 시아노기, 히드록실기, 니트로기, 아미노기, 치환 또는 비치환된 탄소수 1 내지 60의 알킬기, 치환 또는 비치환된 탄소수 3 내지 60의 시클로알킬기, 치환 또는 비치환된 탄소수 6 내지 60의 아릴기, 치환 또는 비치환된 탄소수 3 내지 60의 헤테로아릴기, 치환 또는 비치환된 탄소수 1 내지 60의 알콕시기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴옥시기, 치환 또는 비치환된 탄소수 1 내지 20의 알킬아미노기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴아미노기, 치환 또는 비치환된 탄소수 1 내지 20의 알킬실릴기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴실릴기, 치환 또는 비치환된 탄소수 1 내지 50의 아릴알킬아미노기, 치환 또는 비치환된 탄소수 5 내지 60의 아릴싸이오기, 치환 또는 비치환된 탄소수 2 내지 60의 알케닐기 및 치환 또는 비치환된 탄소수 2 내지 60의 알키닐기 중에서 선택된다.Z is selected from the group consisting of CR 6 , NR 7 , CR 8 R 9 , SiR 10 R 11 , GeR 12 R 13 , PR 14 , BR 15 , Te, O and S, and R 6 to R 15 are selected from the group consisting of hydrogen, A substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C3-C60 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryl group, A substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1- A substituted or unsubstituted C1-C20 alkylamino group, a substituted or unsubstituted C6-C30 arylamino group, a substituted or unsubstituted C1-C20 alkylsilyl group, a substituted or unsubstituted C6-C30 arylsilyl group, A substituted arylalkylamino group having 1 to 50 carbon atoms, a substituted Or an unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, and a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms.
또한, 상기 R1 내지 R10 및 이들의 치환기는 서로 결합하거나 인접한 치환기와 연결되어 지환족, 방향족의 단일환 또는 다환 고리를 형성할 수 있으며, 상기 형성된 지환족, 방향족의 단일환 또는 다환 고리의 탄소원자는 N, S 및 O 중에서 선택되는 어느 하나 이상의 헤테로원자로 치환될 수 있다.R 1 to R 10 and substituents thereof may be bonded to each other or may be connected to adjacent substituents to form a single ring or polycyclic ring of an alicyclic or aromatic group and may form a single ring or multicyclic ring of the formed alicyclic or aromatic ring The carbon atom may be substituted with any one or more heteroatoms selected from N, S and O.
상기 L, R1 내지 R10은 각각 독립적으로 1종 이상의 치환기로 더 치환될 수 있고, 상기 1종 이상의 치환기는 수소, 중수소, 치환 또는 비치환된 탄소수 1 내지 30의 알킬기, 치환 또는 비치환된 탄소수 2 내지 30의 알케닐기, 치환 또는 비치환된 탄소수 2 내지 30의 알키닐기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기, 치환 또는 비치환된 탄소수 2 내지 30의 헤테로시클로알킬기, 치환 또는 비치환된 탄소수 5 내지 30의 시클로알케닐기, 치환 또는 비치환된 탄소수 1 내지 30의 알콕시기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴옥시기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬티옥시기, 치환 또는 비치환된 탄소수 5 내지 30의 아릴티옥시기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬아민기, 치환 또는 비치환된 탄소수 5 내지 30의 아릴아민기, 치환 또는 비치환된 탄소수 5 내지 50의 아릴기, 치환 또는 비치환된 탄소수 3 내지 50의 헤테로아릴기, 치환 또는 비치환된 실릴기, 치환 또는 비치환된 게르마늄기, 치환 또는 비치환된 붕소기, 치환 또는 비치환된 알루미늄기, 카르보닐기, 포스포릴기, 아미노기, 싸이올기, 시아노기, 히드록시기, 니트로기, 할로겐기, 셀레늄기, 텔루륨기, 아미드기, 에테르기 및 에스테르기 중에서 선택될 수 있다.
The L, R < 1 > R 10 may be independently substituted with at least one substituent, and the at least one substituent may be selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms Substituted or unsubstituted C2-C30 alkynyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C2-C30 heterocycloalkyl, substituted or unsubstituted C5- A substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C1-C30 alkoxy group, A substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 30 carbon atoms, A substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted germanium group, a substituted or unsubstituted boron group, An amino group, a thiol group, a cyano group, a hydroxy group, a nitro group, a halogen group, a selenium group, a tellurium group, an amide group, an ether group and an ester group.
본 발명에 있어서, 상기 치환기들의 예시들에 대해서 아래에서 구체적으로 설명하나, 이에 한정되는 것은 아니다.In the present invention, examples of the substituents will be specifically described below, but the present invention is not limited thereto.
본 발명에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 50인 것이 바람직하다. 구체적인 예로는 메틸기, 에틸기, 프로필기, n-프로필기, 이소프로필기, 부틸기, n-부틸기, 이소부틸기, tert-부틸기, sec-부틸기, 1-메틸-부틸기, 1-에틸-부틸기, 펜틸기, n-펜틸기, 이소펜틸기, 네오펜틸기, tert-펜틸기, 헥실기, n-헥실기, 1-메틸펜틸기, 2-메틸펜틸기, 4-메틸-2-펜틸기, 3,3-디메틸부틸기, 2-에틸부틸기, 헵틸기, n-헵틸기, 1-메틸헥실기, 시클로펜틸메틸기, 시클로헥틸메틸기, 옥틸기, n-옥틸기, tert-옥틸기, 1-메틸헵틸기, 2-에틸헥실기, 2-프로필펜틸기, n-노닐기, 2,2-디메틸헵틸기, 1-에틸-프로필기, 1,1-디메틸-프로필기, 이소헥실기, 2-메틸펜틸기, 4-메틸헥실기, 5-메틸헥실기 등이 있으나, 이들에 한정되지 않는다.In the present invention, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 50. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, Ethyl, propyl, isopropyl, n-butyl, isobutyl, isobutyl, isobutyl, A tert-butyl group, a tert-butyl group, a 2-pentyl group, a 3,3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, Ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group , Isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group and the like, but are not limited thereto.
본 발명에 있어서, 알콕시기는 직쇄 또는 분지쇄일 수 있다. 알콕시기의 탄소수는 특별히 한정되지 않으나, 입체적 방해를 주지 않는 범위인 1 내지 30개인 것이 바람직하다. 구체적으로, 메톡시기, 에톡시기, n-프로폭시기, 이소프로폭시기, i-프로필옥시기, n-부톡시기, 이소부톡시기, tert-부톡시기, sec-부톡시기, n-펜틸옥시기, 네오펜틸옥시기, 이소펜틸옥시기, n-헥실옥시기, 3,3-디메틸부틸옥시기, 2-에틸부틸옥시기, n-옥틸옥시기, n-노닐옥시기, n-데실옥시기, 벤질옥시기, p-메틸벤질옥시기 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present invention, the alkoxy group may be linear or branched. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably in the range of 1 to 30, which does not cause steric hindrance. Specific examples thereof include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an i-propyloxy group, a n-butoxy group, an isobutoxy group, a tert- , Neopentyloxy group, isopentyloxy group, n-hexyloxy group, 3,3-dimethylbutyloxy group, 2-ethylbutyloxy group, n-octyloxy group, n- , A benzyloxy group, a p-methylbenzyloxy group, and the like, but are not limited thereto.
본 발명에 있어서, 상기 알케닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 40인 것이 바람직하다. 구체적인 예로는 비닐기, 1-프로페닐기, 이소프로페닐기, 1-부테닐기, 2-부테닐기, 3-부테닐기, 1-펜테닐기, 2-펜테닐기, 3-펜테닐기, 3-메틸-1-부테닐기, 1,3-부타디에닐기, 알릴기, 1-페닐비닐-1-일기, 2-페닐비닐-1-일기, 2,2-디페닐비닐-1-일기, 2-페닐-2-(나프틸-1-일)비닐-1-일기, 2,2-비스(디페닐-1-일)비닐-1-일기, 스틸베닐기, 스티레닐기 등이 있으나 이들에 한정되지 않는다.In the present invention, the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. Specific examples include a vinyl group, a 1-propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2-yl group, But are not limited to, - (naphthyl-1-yl) vinyl-1-yl group, 2,2-bis (diphenyl-1-yl) vinyl-1-yl group, stilbenyl group, styrenyl group and the like.
본 발명에 있어서, 아릴기는 단환식 또는 다환식일 수 있고, 탄소수는 특별히 한정되지 않으나 6 내지 60인 것이 바람직하다. 단환식 아릴기의 예로는 페닐기, 비페닐기, 터페닐기, 스틸벤기 등이 있고, 다환식 아릴기의 예로는 나프틸기, 안트라세닐기, 페난트레닐기, 파이레닐기, 페릴레닐기, 테트라세닐기, 크라이세닐기, 플루오레닐기, 아세나프타센닐기, 트리페닐렌기, 플루오안트렌(fluoranthrene)기 등이 있으나, 본 발명의 범위가 이들 예로만 한정되는 것은 아니다.In the present invention, the aryl group may be monocyclic or polycyclic, and the number of carbon atoms is not particularly limited, but is preferably 6 to 60. [ Examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group and a stilbene group. Examples of the polycyclic aryl group include a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, , A chlorenyl group, a fluorenyl group, an acenaphthacenyl group, a triphenylene group, and a fluororanthrene group, but the scope of the present invention is not limited to these examples.
본 발명에 있어서, 헤테로고리기는 이종원자로 O, N 또는 S를 포함하는 헤테로고리기로서, 탄소수는 특별히 한정되지 않으나 탄소수 2 내지 60인 것이 바람직하다. 헤테로고리기의 예로는 티오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 트리아졸기, 피리딜기, 비피리딜기, 피리미딜기, 트리아진기, 트리아졸기, 아크리딜기, 피리다진기, 피라지닐기, 퀴놀리닐기, 퀴나졸린기, 퀴녹살리닐기, 프탈라지닐기, 피리도 피리미디닐기, 피리도 피라지닐기, 피라지노 피라지닐기, 이소퀴놀린기, 인돌기, 카바졸기, 벤조옥사졸기, 벤조이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨라닐기, 디벤조퓨라닐기, 페난트롤린기, 티아졸릴기, 이소옥사졸릴기, 옥사디아졸릴기, 티아디아졸릴기, 벤조티아졸릴기, 페노티아지닐기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present invention, the heterocyclic group is a heterocyclic group containing O, N or S as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furane group, a furyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A pyridazinyl group, a pyrazinopyrazinyl group, an isoquinoline group, an isoquinolinyl group, an isoquinolinyl group, an isoquinolinyl group, an isoquinolinyl group, an isoquinolyl group, , An indole group, a carbazole group, a benzoxazole group, a benzoimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a dibenzofurancyl group, a phenanthroline group, An isothiazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group and the like, but is not limited thereto.
본 발명에 있어서, 아릴옥시기, 아릴티옥시기, 아릴술폭시기 및 아랄킬아민기 중의 아릴기는 전술한 아릴기의 예시와 같다. 구체적으로 아릴옥시기로는 페녹시기, p-토릴옥시기, m-토릴옥시기, 3,5-디메틸-페녹시기, 2,4,6-트리메틸페녹시기, ptert-부틸페녹시기, 3-비페닐옥시기, 4-비페닐옥시기, 1-나프틸옥시기, 2-나프틸옥시기, 4-메틸-1-나프틸옥시기, 5-메틸-2-나프틸옥시기, 1-안트릴옥시기, 2-안트릴옥시기, 9-안트릴옥시기, 1-페난트릴옥시기, 3-페난트릴옥시기, 9-페난트릴옥시기 등이 있고, 아릴티옥시기로는 페닐티옥시기기, 2－메틸페닐티옥시기, 4－tert－부틸페닐티옥시기 등이 있으며, 아릴술폭시기로는 벤젠술폭시기, p－톨루엔술폭시기 등이 있으나, 이에 한정되지 않는다.In the present invention, the aryl group in the aryloxy group, arylthioxy group, arylsulfoxy group and aralkylamine group is the same as the aforementioned aryl group. Specific examples of the aryloxy group include a phenoxy group, a p-tolyloxy group, an m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6-trimethylphenoxy group, a ptert- Anthryloxy group, 2-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, Anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group, 9-phenanthryloxy group and the like. Examples of the arylthioxy group include phenylthioxy group, 2- A 4-tert-butylphenyloxy group, and the like. Examples of the arylsulfoxy group include benzene sulfoxy group and p-toluenesulfoxy group. However, the present invention is not limited thereto.
본 발명에 있어서, 시클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 60인 것이 바람직하며, 구체적으로 시클로프로필기 시클로부틸기 시클로펜틸기 3-메틸시클로펜틸기 2,3-디메틸시클로펜틸기, 시클로헥실기, 3-메틸시클로헥실기, 4-메틸시클로헥실기, 2,3-디메틸시클로헥실기, 3,4,5-트리메틸시클로헥실기, 4-tert-부틸시클로헥실기, 시클로헵틸기, 시클로옥틸기 등이 있으나, 이에 한정되지 않는다.In the present invention, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and specifically includes cyclopropyl group, cyclobutyl group, cyclopentyl group, 3-methylcyclopentyl group, 2,3-dimethylcyclopentyl group, Methylcyclohexyl group, 2,3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclo An octyl group, and the like, but are not limited thereto.
본 발명에 있어서, 할로겐기의 예로는 불소, 염소, 브롬 또는 요오드가 있다.In the present invention, examples of the halogen group include fluorine, chlorine, bromine or iodine.
본 발명에 있어서, 아릴아민기의 예로는 치환 또는 비치환된 모노아릴아민기, 치환 또는 비치환된 디아릴아민기, 또는 치환 또는 비치환된 트리아릴아민기가 있다. 상기 아릴아민기 중의 아릴기는 단환식 아릴기일 수 있고, 다환식 아릴기일 수 있다. 상기 아릴기가 2 이상을 포함하는 아릴아민기는 단환식 아릴기, 다환식 아릴기, 또는 단환식아릴기와 다환식 아릴기를 동시에 포함할 수 있다.In the present invention, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group having at least two aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.
상기 아릴아민기의 구체적인 예로는 페닐아민기, 나프틸아민기, 비페닐아민기, 안트라세닐아민기, 3-메틸-페닐아민기, 4-메틸-나프틸아민기, 2-메틸-비페닐아민기, 9-메틸-안트라세닐아민기, 디페닐 아민기, 페닐 나프틸 아민기, 디톨릴 아민기, 페닐 톨릴 아민기, 카바졸기 및 트리페닐 아민기 등이 있으나, 이에 한정되는 것은 아니다.Specific examples of the arylamine group include a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a 3-methylphenylamine group, a 4-methylnaphthylamine group, But are not limited to, an amine group, a 9-methyl-anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a carbazole group and a triphenylamine group.
본 발명에 있어서, 실릴기는 구체적으로 트리메틸실릴기, 트리에틸실릴기, t-부틸디메틸실릴기, 비닐디메틸실릴기, 프로필디메틸실릴기, 트리페닐실릴기, 디페닐실릴기, 페닐실릴기 등이 있으나 이에 한정되지 않는다.In the present invention, the silyl group is specifically exemplified by trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, But are not limited thereto.
본 발명에 있어서, 헤테로아릴아민기 중의 헤테로 아릴기는 전술한 헤테로고리기의 예시 중에서 선택될 수 있다.In the present invention, the heteroaryl group in the heteroarylamine group can be selected from the examples of the above-mentioned heterocyclic group.
본 발명에 있어서, 알킬티옥시기, 알킬술폭시기 중의 알킬기는 전술한 알킬기의 예시와 같다. 구체적으로 알킬티옥시기로는 메틸티옥시기, 에틸티옥시기, tert－부틸티옥시기, 헥실티옥시기, 옥틸티옥시기 등이 있고, 알킬술폭시기로는 메실, 에틸술폭시기, 프로필술폭시기, 부틸술폭시기 등이 있으나, 이에 한정되지 않는다.In the present invention, the alkyloxy group in the alkylthio group and the alkyl group in the alkylsulfoxy group are the same as the aforementioned alkyl groups. Specific examples of the alkyloxy group include a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group and an octylthio group. Examples of the alkylsulfoxy group include a mesyl group, an ethylsulfoxy group, a propylsulfoxy group, But are not limited thereto.
본 발명에 있어서, "치환 또는 비치환된"이란, 중수소, 할로겐기, 니트릴기, 니트로기, 히드록시기, 알킬기, 시클로알킬기, 알콕시기, 아릴옥시기, 알킬티옥시기, 아릴티옥시기, 알킬술폭시기, 아릴술폭시기, 알케닐기, 실릴기, 붕소기, 알킬아민기, 아랄킬아민기, 아릴아민기, 아릴기, 플루오레닐기, 카바졸기 및 N, O 및 S 원자 중 1개 이상을 포함하는 헤테로고리기 중 적어도 하나의 치환기로 치환 또는 비치환된 것을 의미한다.In the present invention, the "substituted or unsubstituted" means a group selected from the group consisting of deuterium, halogen, nitrile, nitro, hydroxy, alkyl, cycloalkyl, , An arylsulfoxy group, an alkenyl group, a silyl group, a boron group, an alkylamine group, an aralkylamine group, an arylamine group, an aryl group, a fluorenyl group, a carbazole group and at least one of N, O and S atoms Substituted or unsubstituted with at least one substituent in the heterocyclic group.
본 발명에 있어서, 치환된 아릴렌기라 함은, 페닐기, 비페닐기, 나프탈렌기, 플루오레닐기, 파이레닐기, 페난트레닐기, 페릴렌기, 테트라세닐기. 안트라센닐기 등이 다른 치환기로 치환된 것을 의미한다.In the present invention, the substituted arylene group means a phenyl group, a biphenyl group, a naphthalene group, a fluorenyl group, a pyrenyl group, a phenanthrenyl group, a perylene group, a tetracenyl group. Anthracenyl group and the like are substituted with other substituents.
본 발명에 있어서, 치환된 헤테로아릴렌기라 함은, 피리딜기, 티오페닐기, 트리아진기, 퀴놀린기, 페난트롤린기, 이미다졸기, 티아졸기, 옥사졸기, 카바졸기 및 이들의 축합헤테로고리기, 예컨대 벤즈퀴놀린기, 벤즈이미다졸기, 벤즈옥사졸기, 벤즈티아졸기, 벤즈카바졸기, 디벤조티오페닐기, 디벤조퓨란기 등이 다른 치환기로 치환된 것을 의미한다.
In the present invention, the substituted heteroarylene group includes a pyridyl group, a thiophenyl group, a triazine group, a quinoline group, a phenanthroline group, an imidazole group, a thiazole group, an oxazole group, a carbazole group and condensed heterocyclic groups, Such as a benzoquinoline group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzzcarbazole group, a dibenzothiophenyl group, a dibenzofurane group and the like are substituted with other substituents.
상기 [화학식 1]로 표시되는 본 발명에 따른 유기발광 화합물은 그 구조적 특이성으로 인하여 유기전계발광소자의 유기물층으로 사용될 수 있고, 보다 구체적으로 유기물층 내의 발광층에 인광 호스트 화합물로 사용될 수 있다.The organic luminescent compound according to the present invention represented by
특히, 본 발명에 따른 [화학식 1]로 표시되는 발광층의 인광 호스트 화합물에 채용될 수 있는 유기발광 화합물의 구체적인 예로는 하기 화합물들이 있으나, 이들에만 한정되는 것은 아니다.Particularly, specific examples of the organic luminescent compound that can be employed in the phosphorescent host compound of the luminescent layer represented by
상기와 같은 구조의 코어 구조에 다양한 치환기를 도입함으로써 도입된 치환기의 고유 특성을 갖는 유기발광 화합물을 합성할 수 있다. 예컨대, 유기전계발광소자의 제조시 사용되는 정공 주입층 물질, 정공 수송층 물질, 발광층 물질, 및 전자 수송층 물질에 사용되는 치환기를 상기 구조에 도입함으로써 각 유기물층에서 요구하는 조건들을 충족시키는 물질을 제조할 수 있다.An organic luminescent compound having the intrinsic characteristics of the substituent introduced by introducing various substituents into the core structure having the above structure can be synthesized. For example, by introducing a substituent used in a hole injecting layer material, a hole transporting layer material, a light emitting layer material, and an electron transporting layer material used in manufacturing an organic electroluminescent device into the structure, a material meeting the requirements of each organic material layer is manufactured .
특히, 본 발명에 따른 [화학식 1]로 표시되는 유기발광 화합물은 상기에서 살펴본 바와 같이, 특징적 코어 구조체에 치환기를 도입한 결과 평판 구조도가 우수하고, 높은 삼중항(triplet) 상태를 가짐을 확인하였는 바, 이를 유기전계발광소자의 발광층 호스트 화합물에 채용시 효율, 구동전압, 수명 등에서 우수한 특성을 나타내는 유기전계발광소자의 구현이 가능하다.
In particular, as described above, the organic luminescent compound represented by
본 발명의 화합물은 유기전계발광소자의 통상의 제조방법에 따라 소자에 적용할 수 있다.The compound of the present invention can be applied to a device according to a conventional method of manufacturing an organic electroluminescent device.
본 발명의 하나의 실시예에 따른 유기전계발광소자는 제1 전극과 제2 전극 및 이 사이에 배치된 유기물층을 포함하는 구조로 이루어질 수 있으며, 본 발명에 따른 유기발광 화합물을 소자의 유기물층에 사용한다는 것을 제외하고는 통상의 소자의 제조 방법 및 재료를 사용하여 제조될 수 있다.The organic electroluminescent device according to one embodiment of the present invention may have a structure including a first electrode, a second electrode and an organic material layer disposed therebetween, and the organic electroluminescent compound according to the present invention may be used for an organic material layer And can be manufactured using conventional device manufacturing methods and materials.
본 발명에 따른 유기전계발광소자의 유기물층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 정공 주입층, 정공 수송층, 발광층, 전자 수송층, 전자 주입층 등을 포함하는 구조를 가질 수 있다. 그러나, 이에 한정되지 않고 더 적은 수의 유기물층을 포함할 수도 있다.The organic material layer of the organic electroluminescent device according to the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer. However, it is not limited to this and may include a smaller number of organic layers.
따라서, 본 발명의 유기전계발광소자에서, 상기 유기물층은 정공 주입층, 정공 수송층, 전자 수송층, 전자 주입층, 정공 주입 및 정공 수송을 동시에 하는 층, 전자 주입 및 전자수송을 동시에 하는 층 및 발광층 중 1층 이상을 포함할 수 있고, 상기 층들 중 1층 이상이 상기 [화학식 1]로 표시되는 화합물을 포함할 수 있다.Therefore, in the organic electroluminescent device of the present invention, the organic material layer may be a hole injecting layer, a hole transporting layer, an electron transporting layer, an electron injecting layer, a layer simultaneously injecting and transporting holes, a layer simultaneously performing electron injection and electron transporting, One or more layers may be included, and at least one of the layers may include a compound represented by the above formula (1).
특히, 본 발명에 따른 유기발광 화합물은 발광층 내 호스트 물질로서 포함될 수 있다.In particular, the organic luminescent compound according to the present invention can be included as a host material in the luminescent layer.
상기 [화학식 1]로 표시되는 화합물이 발광층 내 호스트 물질로서 포함되는 경우에, 상기 발광층은 1종 이상의 인광 도펀트를 포함할 수 있으며, 상기 발광층이 호스트 및 도펀트를 포함할 경우, 도펀트의 함량은 통상적으로 호스트 약 100 중량부를 기준으로 하여 약 0.01 내지 약 20 중량부의 범위에서 선택될 수 있다.In the case where the compound represented by
본 발명의 일 실시예에 의하면, 상기 발광층에 본 발명에 따른 [화학식 1]로 표시되는 호스트 화합물과 하기의 [구조식 2] 내지 [구조식 8] 중에서 선택되는 도펀트 화합물을 1종 이상 더 포함할 수 있다.According to an embodiment of the present invention, the light emitting layer may further contain at least one dopant compound selected from the following [structural formulas 2] to [structural formula 8] in the host compound represented by the general formula [1] have.
[구조식 2][Structural formula 2]
[구조식 3][Structural Formula 3]
[구조식 4][Structural Formula 4]
[구조식 5][Structural Formula 5]
[구조식 6][Structural Formula 6]
[구조식 7][Structural Formula 7]
[구조식 8][Structural formula 8]
이와 같은 다층 구조의 유기물층에서 상기 [화학식 1]로 표시되는 화합물은 바람직하게는 발광층이지만, 정공 주입/정공 수송과 발광을 동시에 하는 층, 정공 수송과 발광을 동시에 하는 층, 또는 전자 수송과 발광을 동시에 하는 층 등에도 포함될 수 있다.In the organic compound layer having such a multi-layer structure, the compound represented by the formula (1) is preferably a light emitting layer, but may be a layer that simultaneously transports holes and holes, a layer that simultaneously transports holes and emits light, It may be included at the same time.
예컨대, 본 발명에 따른 유기 전자 소자의 구조는 도 1 내지 5에 예시되어 있다.For example, the structure of an organic electronic device according to the present invention is illustrated in Figs.
도 1에는 기판(1) 위에 양극(2), 정공 주입층(3), 정공 수송층(4), 발광층(5), 전자 수송층(6) 및 음극(7)이 순차적으로 적층된 유기 전자 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 정공 주입층(3), 정공 수송층(4), 발광층(5) 또는 전자 수송층(6)에 포함될 수 있다.1 shows an organic electronic device in which an
도 2에는 기판(1) 위에 양극(2), 정공 주입층(3), 정공 수송층(4), 발광층(5) 및 음극(7)이 순차적으로 적층된 유기 전자 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 정공 주입층(3), 정공 수송층(4) 또는 전자 수송층(6)에 포함될 수 있다.2 shows the structure of an organic electronic device in which an
도 3에는 기판(1) 위에 양극(2), 정공 수송층(4), 발광층(5), 전자 수송층(6) 및 음극(7)이 순차적으로 적층된 유기 전자 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 정공 수송층(4), 발광층(5) 또는 전자 수송층(6)에 포함될 수 있다.3 illustrates the structure of an organic electronic device in which an
도 4에는 기판(1) 위에 양극(2), 발광층(5), 전자 수송층(6) 및 음극(7)이 순차적으로 적층된 유기 전자 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 발광층(5) 또는 전자 수송층(6)에 포함될 수 있다.4 illustrates the structure of an organic electronic device in which an
도 5에는 기판(1) 위에 양극(2), 발광층(5) 및 음극(7)이 순차적으로 적층된 유기 전자 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 발광층(5)에 포함될 수 있다.5 illustrates the structure of an organic electronic device in which an
예컨대, 본 발명에 따른 유기 전자 소자의 구조는 도 1 내지 5에 예시되어 있다.For example, the structure of an organic electronic device according to the present invention is illustrated in Figs.
도 1에는 기판(1) 위에 양극(2), 정공 주입층(3), 정공 수송층(4), 발광층(5), 전자 수송층(6) 및 음극(7)이 순차적으로 적층된 유기전계발광소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 [화학식 1]로 표시되는 화합물은 상기 정공 주입층(3), 정공 수송층(4), 발광층(5) 또는 전자 수송층(6)에 포함될 수 있다.1 shows an
도 2에는 기판(1) 위에 양극(2), 정공 주입층(3), 정공 수송층(4), 발광층(5) 및 음극(7)이 순차적으로 적층된 유기전계발광소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 [화학식 1]로 표시되는 화합물은 상기 정공 주입층(3), 정공 수송층(4) 또는 전자 수송층(6)에 포함될 수 있다.2 shows a structure of an organic electroluminescent device in which an
도 3에는 기판(1) 위에 양극(2), 정공 수송층(4), 발광층(5), 전자 수송층(6) 및 음극(7)이 순차적으로 적층된 유기전계발광소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 [화학식 1]로 표시되는 화합물은 상기 정공 수송층(4), 발광층(5) 또는 전자 수송층(6)에 포함될 수 있다.3 illustrates the structure of an organic electroluminescent device in which an
도 4에는 기판(1) 위에 양극(2), 발광층(5), 전자 수송층(6) 및 음극(7)이 순차적으로 적층된 유기전계발광소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 [화학식 1]로 표시되는 화합물은 상기 발광층(5) 또는 전자 수송층(6)에 포함될 수 있다.4 shows the structure of an organic electroluminescent device in which an
도 5에는 기판(1) 위에 양극(2), 발광층(5) 및 음극(7)이 순차적으로 적층된 유기전계발광소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 [화학식 1]로 표시되는 화합물은 상기 발광층(5)에 포함될 수 있다.5 illustrates the structure of an organic electroluminescent device in which an
예컨대, 본 발명에 따른 유기전계발광소자는 스퍼터링(sputtering)이나 전자빔 증발(e-beam evaporation)과 같은 PVD(physical vapor deposition) 방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 정공 주입층, 정공 수송층, 발광층, 전자 수송층을 포함하는 유기물층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다.For example, the organic electroluminescent device according to the present invention can be manufactured by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form a metal oxide or a conductive metal oxide on the substrate, An anode is formed by depositing an alloy on the anode, and an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer is formed on the anode, and then a substance usable as a cathode is deposited thereon.
이와 같은 방법 외에도, 기판 상에 음극 물질부터 유기물층, 양극 물질을 차례로 증착시켜 유기전계발광소자를 만들 수도 있다. 상기 유기물층은 정공 주입층, 정공 수송층, 발광층 및 전자 수송층 등을 포함하는 다층 구조일 수도 있으나, 이에 한정되지 않고 단층 구조일 수 있다. 또한, 상기 유기물층은 다양한 고분자 소재를 사용하여 증착법이 아닌 솔벤트 프로세스(solvent process), 예컨대 스핀 코팅, 딥 코팅, 닥터 블레이딩, 스크린 프린팅, 잉크젯 프린팅 또는 열 전사법 등의 방법에 의하여 더 적은 수의 층으로 제조할 수 있다.In addition to such a method, an organic electroluminescent device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate. The organic material layer may have a multi-layer structure including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, but is not limited thereto and may have a single layer structure. In addition, the organic material layer may be formed using a variety of polymer materials by a solvent process such as a spin coating process, a dip coating process, a doctor blading process, a screen printing process, an inkjet printing process or a thermal transfer process, Layer.
상기 양극 물질로는 통상 유기물층으로 정공주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 본 발명에서 사용될 수 있는 양극 물질의 구체적인 예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금, 아연 산화물, 인듐 산화물, 인듐 주석 산화물(ITO), 인듐 아연 산화물(IZO)과 같은 금속 산화물, ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합, 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다.As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer. Specific examples of the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof, zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO) metal oxides, ZnO: Al or SnO 2: a combination of a metal and an oxide such as Sb, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT) , Conductive polymers such as polypyrrole and polyaniline, but are not limited thereto.
상기 음극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 음극 물질의 구체적인 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 타이타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석 및 납과 같은 금속 또는 이들의 합금, LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이들에만 한정되는 것은 아니다.The negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or an alloy thereof, a multilayer such as LiF / Al or LiO 2 / Structural materials, and the like, but are not limited thereto.
정공 주입 물질로는 낮은 전압에서 양극으로부터 정공을 잘 주입받을 수 있는 물질로서, 정공 주입 물질의 HOMO(highest occupied molecular orbital)가 양극 물질의 일함수와 주변 유기물층의 HOMO 사이인 것이 바람직하다. 정공 주입 물질의 구체적인 예로는 금속 포피린(porphyrine), 올리고티오펜, 아릴아민 계열의 유기물, 헥사니트릴 헥사아자트리페닐렌, 퀴나크리돈(quinacridone) 계열의 유기물, 페릴렌(perylene) 계열의 유기물, 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다.As the hole injecting material, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene, quinacridone-based organic materials, perylene-based organic materials, Anthraquinone, polyaniline and a polythiophene-based conductive polymer, but are not limited thereto.
정공 수송 물질로는 양극이나 정공 주입층으로부터 정공을 수송 받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 아릴아민 계열의 유기물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이들에만 한정되는 것은 아니다.As the hole transporting material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer and having high mobility to holes is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
발광 물질로는 정공 수송층과 전자 수송층으로부터 정공과 전자를 각각 수송받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 형광이나 인광에 대한 양자효율이 좋은 물질이 바람직하다. 구체적인 예로는 8-히드록시-퀴놀린 알루미늄 착물(Alq3), 카르바졸 계열 화합물, 이량체화 스티릴(dimerized styryl) 화합물, BAlq, 10-히드록시벤조 퀴놀린-금속 화합물, 벤족사졸, 벤즈티아졸 및 벤즈이미다졸 계열의 화합물, 폴리(p-페닐렌비닐렌)(PPV) 계열의 고분자, 스피로(spiro) 화합물, 폴리플루오렌, 루브렌 등이 있으나, 이들에만 한정되는 것은 아니다.The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and combining holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having a high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ), carbazol-based compounds, dimerized styryl compounds, BAlq, 10-hydroxybenzoquinoline-metal compounds, benzoxazole, benzthiazole and A benzimidazole-based compound, a poly (p-phenylene vinylene) (PPV) -based polymer, a spiro compound, polyfluorene, rubrene, and the like.
전자 수송 물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 8-히드록시퀴놀린의 Al 착물, Alq3를 포함한 착물, 유기 라디칼 화합물, 히드록시플라본-금속 착물 등이 있으나, 이들에만 한정되는 것은 아니다.
As the electron transporting material, a material capable of transferring electrons from the cathode well into the light emitting layer, which is highly mobile, is suitable. Specific examples thereof include, but are not limited to, an Al complex of 8-hydroxyquinoline, a complex containing Alq 3 , an organic radical compound, and a hydroxyflavone-metal complex.
본 발명에 따른 유기전계발광소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic electroluminescent device according to the present invention may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.
또한, 본 발명에 따른 유기발광 화합물은 유기 태양 전지, 유기 감광체, 유기 트랜지스터 등을 비롯한 유기 전자 소자에서도 유기전계발광소자에 적용되는 것과 유사한 원리로 작용할 수 있다.
In addition, the organic electroluminescent compound according to the present invention can act on a principle similar to that applied to an organic electroluminescent device in an organic electronic device including an organic solar cell, an organophotoreceptor, an organic transistor and the like.
이하, 본 발명의 이해를 돕기 위하여 바람직한 실시예를 제시한다. 그러나, 하기의 실시예는 본 발명을 예시하기 위한 것이며, 이에 의하여 본 발명의 범위가 한정되는 것은 아니다.
Hereinafter, preferred embodiments of the present invention will be described in order to facilitate understanding of the present invention. However, the following examples are intended to illustrate the invention and are not intended to limit the scope of the invention.
실시예Example
1 : 화합물 1의 합성 1: Synthesis of
(1) (One) 제조예Manufacturing example 1 : 중간체 1-1의 합성 1: Synthesis of intermediate 1-1
3-bromo-1H-indole(2.0 g, 0.010 mol)에 bromobenzene(1.6 g, 0.010 mol), Pd(dba)2(0.5 g, 0.0005 mol), sodium-tert-butoxide(1.9 g, 0.020 mol)에 TOL 70 mL를 넣고 95 ℃에서 4시간 교반하여 반응시켰다. 반응종료 후 H20:MC에 층분리 후 컬럼정제(n-HEXANE:MC)하여 중간체 1-1를 2.1 g (79%)수득하였다 (m/z=272)
To a solution of bromobenzene (1.6 g, 0.010 mol), Pd (dba) 2 (0.5 g, 0.0005 mol) and sodium tert-butoxide (1.9 g, 0.020 mol) in 3-bromo-1H- indole TOL (70 mL) was added, and the mixture was reacted at 95 DEG C for 4 hours with stirring. After completion of the reaction H 2 0: after separation layer MC column purification: yield (n-HEXANE MC) and 2.1 g (79%) of Intermediate 1-1 (m / z = 272)
(2) (2) 제조예Manufacturing example 2 : 중간체 1-2의 합성 2: Synthesis of intermediate 1-2
중간체 1-1(3.0 g, 0.011 mol)에 bis(pinacolato)dibron(3.3 g, 0.013 mol), PdCl2(dppf)(0.4 g, 0.0005 mol), potassium-acetate(3.0 g, 0.022 mol)에 1,4-dioxane 100 mL를 넣고 95 ℃에서 24시간 교반하여 반응시켰다. 반응 종료 후 냉각하여 H20:MC에 층분리 후 컬럼정제(n-Hexane:MC)하여 중간체 1-2를 2.5 g (수율71%) 수득하였다. (m/z=319)
To pinacolato dibron (3.3 g, 0.013 mol), PdCl 2 (dppf) (0.4 g, 0.0005 mol) and potassium acetate (3.0 g, 0.022 mol) were added to Intermediate 1-1 (3.0 g, 0.011 mol) , 4-dioxane (100 mL), and the mixture was reacted at 95 ° C for 24 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H 2 O: MC and subjected to column purification (n-hexane: MC) to obtain 2.5 g (yield 71%) of intermediate 1-2. (m / z = 319)
(3) (3) 제조예Manufacturing example 3 : 중간체 1-3의 합성 3: Synthesis of intermediate 1-3
4'-bromo-3,5-dichlorobiphenyl(3.0 g, 0.010 mol)에 2-phenyl-1H-benzo[d]imidazole(1.9 g, 0.010 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <중간체 1-3> 3.2 g (수율 76%)을 얻었다.(m/z=415)
(1.9 g, 0.010 mol) was added to 4'-bromo-3,5-dichlorobiphenyl (3.0 g, 0.010 mol) and 2-phenyl-1H-benzo [d] imidazole 3.2 g (yield 76%) of Intermediate 1-3 was obtained (m / z = 415)
(4) (4)
제조예Manufacturing example
4 : 화합물 1의 합성 4: Synthesis of
중간체 1-2(6.0 g, 0.018 mol)에 중간체 1-3(3.3 g, 0.008 mol), Pd(pph3)4(1.0 g, 0.0009 mol), potassium carbonate(6.5 g, 0.036 mol)에 THF 130 mL를 넣고 65 ℃에서 4시간 교반하여 반응시켰다. 반응종료 후 H20:MC에 층분리 후 컬럼정제(n-HEXANE:MC)하여 화합물 1을 9.3 g (71%)수득하였다.Intermediate 1-2 (6.0 g, 0.018 mol) in intermediate 1-3 (3.3 g, 0.008 mol) , Pd (pph 3) THF in 4 (1.0 g, 0.0009 mol) , potassium carbonate (6.5 g, 0.036 mol) 130 mL, and the mixture was reacted at 65 ° C for 4 hours with stirring. After completion of the reaction, the reaction mixture was separated into H 2 O: MC and column-purified (n-HEXANE: MC) to obtain 9.3 g (71%) of
H-NMR (200MHz, CDCl3):δ ppm, 1H(8.56/d, 7.59/d, 7.41/m) 2H(8.28/d, 8.17/d, 7.79/d, 7.71/d, 7.68/d, 7.51/m, 7.45/m, 7.36/s, 7.22/m) 3H(7.66/s) 4H(7.58/m, 7.50/d, 7.42/m) H-NMR (200MHz, CDCl 3 ): δ ppm, 1H (8.56 / d, 7.59 / d, 7.41 / m) 2H (8.28 / d, 8.17 / d, 7.79 / d, 7.71 / d, 7.68 / d, 7.51 7.46 / s, 7.22 / m) 3H (7.66 / s) 4H (7.58 / m, 7.50 / d, 7.42 /
LC/MS: m/z= 729[(M+1)+]
LC / MS: m / z = 729 [(M + 1) < + &
실시예Example
2 : 화합물 5의 합성 2: Synthesis of
(1) (One) 제조예Manufacturing example 1 : 중간체 5-1의 합성 1: Synthesis of intermediate 5-1
중간체 1-2(6.0 g, 0.018 mol)에 3,6-dibromo-9H-carbazole(2.6 g, 0.008 mol)를 넣고 실시예 1-제조예 (4)에서 사용된 동일한 방법으로 합성하여 <중간체 5-1> 3.1 g (수율 71%)을 얻었다.(m/z=549)
Synthesis was conducted in the same manner as in Example 1 (4) except that 3,6-dibromo-9H-carbazole (2.6 g, 0.008 mol) was added to Intermediate 1-2 (6.0 g, 0.018 mol) -1> 3.1 g (yield: 71%). (M / z = 549)
(2) (2)
제조예Manufacturing example
2 : 화합물 5의 합성 2: Synthesis of
중간체 5-1(5.0 g, 0.009 mol)에 bromobenzene(1.4 g, 0.009 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <화합물 5> 4.5 g (수율 80%)을 얻었다.4.5 g (80% yield) of
H-NMR (200MHz, CDCl3):δ ppm, 1H (8.18/d, 8.00/d, 7.87/d, 7.69/d) 2H(8.17/d, 7.77/s, 7.71/d, 7.36/s) 3H(7.45/m) 4H(7.42/m) 6H(7.58/m, 7.50/d) H-NMR (200MHz, CDCl 3 ): δ ppm, 1H (8.18 / d, 8.00 / d, 7.87 / d, 7.69 / d) 2H (8.17 / d, 7.77 / s, 7.71 / d, 7.36 / s) 3H (7.45 / m) 4H (7.42 / m) 6H (7.58 / m, 7.50 / d)
LC/MS: m/z= 626[(M+1)+]
LC / MS: m / z = 626 [(M + 1) < + &
실시예Example
3 : 화합물 6의 합성 3: Synthesis of
(1) (One) 제조예Manufacturing example 1 : 중간체 6-1의 합성 1: Synthesis of intermediate 6-1
1,4-dibromobenzene(1.9 g, 0.008 mol)에 triphenylen-2-ylboronic acid(2.7 g, 0.010 mol)를 넣고 실시예 1-제조예 (4)에서 사용된 동일한 방법으로 합성하여 <중간체 6-1> 2.1 g (수율 69%)을 얻었다.(m/z=383)
2-ylboronic acid (2.7 g, 0.010 mol) was added to 1,4-dibromobenzene (1.9 g, 0.008 mol) and the intermediate <6-1 > 2.1 g (yield 69%). (M / z = 383)
(2) (2)
제조예Manufacturing example
2 : 화합물 6의 합성 2: Synthesis of
중간체 5-1(5.0 g, 0.009 mol)에 중간체 6-1(3.4 g, 0.009 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <화합물 6> 5.8 g (수율 76%)을 얻었다.Synthesis was conducted in the same manner as in Example 1 (1), except that Intermediate 6-1 (3.4 g, 0.009 mol) was added to Intermediate 5-1 (5.0 g, 0.009 mol) 76%).
H-NMR (200MHz, CDCl3):δ ppm, 1H(9.15/s, 8.18/d, 8.17/d, 8.04/d, 8.00/d, 7.87/d, 7.69/d) 2H(8.93/d, 8.17/d, 8.12/d, 7.88/m, 7.82/m, 7.79/d, 7.77/s, 7.71/d, 7.68/d, 7.45/m, 7.36/s) 4H(7.58/m, 7.50/d, 7.42/m) H-NMR (200MHz, CDCl 3 ): δ ppm, 1H (9.15 / s, 8.18 / d, 8.17 / d, 8.04 / d, 8.00 / d, 7.87 / d, 7.69 / d) 2H (8.93 / d, 8.17 m, 7.50 / d, 7.47 / s, 7.71 / d, 7.68 / d, 7.45 / m, 7.36 / / m)
LC/MS: m/z=853[(M+1)+]
LC / MS: m / z = 853 [(M + 1) < + &
실시예Example
4 : 화합물 7의 합성 4: Synthesis of
(1) (One)
제조예Manufacturing example
1 : 화합물 7의 합성 1: Synthesis of
중간체 5-1(5.0 g, 0.009 mol)에 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine(3.1 g, 0.009 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <화합물 7> 6.0 g (수율 78%)을 얻었다.(3.1 g, 0.009 mol) was added to Intermediate 5-1 (5.0 g, 0.009 mol) and 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5- ) To obtain 6.0 g (yield 78%) of <
H-NMR (200MHz, CDCl3):δ ppm, 1H(8.18/d, 8.00/d, 7.87/d, 7.69/d) 2H(8.17/d, 7.79/d, 7.77/s, 7.71/d, 7.68/d, 7.45/m, 7.41/m, 7.36/s) 4H(8.28/d, 7.58/m, 7.51/m, 7.50/d, 7.42/m) H-NMR (200MHz, CDCl 3 ): δ ppm, 1H (8.18 / d, 8.00 / d, 7.87 / d, 7.69 / d) 2H (8.17 / d, 7.79 / d, 7.77 / s, 7.71 / d, 7.68 7.58 / m, 7.41 / m, 7.36 / s) 4H (8.28 / d, 7.58 /
LC/MS: m/z=858 [(M+1)+]
LC / MS: m / z = 858 [(M + 1) < + &
실시예Example 5 : 화합물 14의 합성 5: Synthesis of Compound 14
(1) (One) 제조예Manufacturing example 1 : 화합물 14의 합성 1: Synthesis of Compound 14
중간체 5-1(5.0 g, 0.009 mol)에 9-(4-bromophenyl)-9H-carbazole(2.9 g, 0.009 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <화합물 14> 5.8 g (수율 82%)을 얻었다.Synthesis was conducted in the same manner as in Example 1 (1) except that 9- (4-bromophenyl) -9H-carbazole (2.9 g, 0.009 mol) was added to Intermediate 5-1 (5.0 g, 0.009 mol) To obtain 5.8 g (yield 82%) of Compound 14.
H-NMR (200MHz, CDCl3):δ ppm, 1H(8.55/d, 8.18/d, 8.12/d, 8.00/d, 7.94/d, 7.87/d, 7.69/d, 7.63/d, 7.50/m, 7.33/m, 7.29/m, 7.25/m) 2H(8.17/d, 7.77/s, 7.71/d, 7.45/m, 7.36/s) 4H(7.62/d, 7.58/m, 7.50/d, 7.42/m) H-NMR (200MHz, CDCl 3 ): δ ppm, 1H (8.55 / d, 8.18 / d, 8.12 / d, 8.00 / d, 7.94 / d, 7.87 / d, 7.69 / d, 7.63 / d, 7.50 / m M, 7.25 / m) 2H (8.17 / d, 7.77 / s, 7.71 / d, 7.45 / m, 7.36 / / m)
LC/MS: m/z= 791[(M+1)+]
LC / MS: m / z = 791 [(M + 1) < + &
실시예Example 6 : 화합물 16의 합성 6: Synthesis of Compound 16
(1) (One) 제조예Manufacturing example 1 : 화합물 16의 합성 1: Synthesis of Compound (16)
중간체 5-1(5.0 g, 0.009 mol)에 3-(4-bromophenyl)-9-phenyl-9H-carbazole(3.6 g, 0.009 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <화합물 16> 6.2 g (수율 79%)을 얻었다.The same procedure as in Example 1 (1) (1) was performed except that 3- (4-bromophenyl) -9-phenyl-9H-carbazole (3.6 g, 0.009 mol) was added to Intermediate 5-1 To obtain 6.2 g (yield 79%) of < Compound 16 >.
H-NMR (200MHz, CDCl3):δ ppm, 1H(8.55/d, 8.18/d, 8.00/d, 7.94/d, 7.33/m, 7.25/m) 2H(8.17/d, 7.87/d, 7.79/d, 7.71/d, 7.69/d, 7.68/d, 7.36/s) 3H(7.77/s, 7.45/m) 4H(7.42/m) 6H(7.58/m, 7.50/d) H-NMR (200MHz, CDCl 3 ): δ ppm, 1H (8.55 / d, 8.18 / d, 8.00 / d, 7.94 / d, 7.33 / m, 7.25 / m) 2H (8.17 / d, 7.87 / d, 7.79 (7.58 / m, 7.50 / d), 7.71 / d, 7.69 / d, 7.68 / d, 7.36 /
LC/MS: m/z=868 [(M+1)+]
LC / MS: m / z = 868 [(M + 1) < + &
실시예Example 7 : 화합물 17의 합성 7: Synthesis of Compound 17
(1) (One) 제조예Manufacturing example 1 : 화합물 17의 합성 1: Synthesis of Compound 17
중간체 5-1(5.0 g, 0.009 mol)에 4-(4-bromophenyl)dibenzo[b,d]thiophene (3.1 g, 0.009 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <화합물 17> 5.5 g (수율 76%)을 얻었다.(3.1 g, 0.009 mol) was added to Intermediate 5-1 (5.0 g, 0.009 mol) and 4- (4-bromophenyl) dibenzo [b, d] thiophene To obtain 5.5 g (yield 76%) of < Compound 17 >.
H-NMR (200MHz, CDCl3):δ ppm, 1H(8.45/d, 8.41/d, 8.20/d, 8.18/d, 8.00/d, 7.98/d, 7.87/d, 7.69/d, 7.58/m, 7.52/m, 7.50/m) 2H(8.17/d, 7.79/d, 7.77/s, 7.71/d, 7.68/d, 7.45/m, 7.36/s) 4H(7.58/m, 7.50/d, 7.42/m) H-NMR (200MHz, CDCl 3 ): δ ppm, 1H (8.45 / d, 8.41 / d, 8.20 / d, 8.18 / d, 8.00 / d, 7.98 / d, 7.87 / d, 7.69 / d, 7.58 / m M, 7.50 / d, 7.42 / m, 7.50 / m) 2H (8.17 / d, 7.79 / d, 7.77 / s, 7.71 / d, 7.68 / / m)
LC/MS: m/z=809 [(M+1)+]
LC / MS: m / z = 809 [(M + 1) < + &
실시예Example 8 : 화합물 28의 합성 8: Synthesis of Compound 28
(1) (One) 제조예Manufacturing example 1 : 중간체 28-1의 합성 1: Synthesis of intermediate 28-1
3-bromo-9H-carbazole(3.0 g, 0.012 mol)에 1-bromodibenzo[b,d]thiophene (3.2 g, 0.012 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <중간체 28-1> 3.9 g (수율 76%)을 얻었다.(m/z=428)
Synthesis was conducted in the same manner as in Example 1 (1) except that 1-bromodibenzo [b, d] thiophene (3.2 g, 0.012 mol) was added to 3-bromo-9H-carbazole (3.0 g, 0.012 mol) (M / z = 428) of <Intermediate 28-1> (yield: 76%).
(2) (2) 제조예Manufacturing example 2 : 중간체 28-1-1의 합성 2: Synthesis of intermediate 28-1-1
중간체 28-1(4.3 g, 0.010 mol)에 bis(pinacolato)dibron(3.0 g, 0.012 mol) 를 넣고 실시예 1-제조예 (2)에서 사용된 동일한 방법으로 합성하여 <중간체 28-1-1> 3.4 g (수율 71%)을 얻었다.(m/z=475)
The intermediate 28-1 (4.3 g, 0.010 mol) was synthesized in the same manner as in Example 1 (2) except that bis (pinacolato) dibron (3.0 g, 0.012 mol) > 3.4 g (yield 71%). (M / z = 475)
(3) (3) 제조예Manufacturing example 3 : 중간체 28-2의 합성 3: Synthesis of intermediate 28-2
중간체 28-1-1(4.8 g, 0.010 mol)에 1-bromo-3,5-dichlorobenzene(1.8 g, 0.008 mol)를 넣고 실시예 1-제조예 (4)에서 사용된 동일한 방법으로 합성하여 <중간체 28-2> 2.8 g (수율 71%)을 얻었다.(m/z=494)
3,5-dichlorobenzene (1.8 g, 0.008 mol) was added to Intermediate 28-1-1 (4.8 g, 0.010 mol) in the same manner as in Example 1 (4) To obtain 2.8 g (yield 71%) of intermediate 28-2 (m / z = 494)
(3) (3) 제조예Manufacturing example 3 : 화합물 28의 합성 3: Synthesis of Compound 28
중간체 1-2(6.0 g, 0.018 mol)에 중간체 28-2(4.0 g, 0.008 mol)를 넣고 실시예 1-제조예 (4)에서 사용된 동일한 방법으로 합성하여 <화합물 28> 4.8 g (수율 74%)을 얻었다.Synthesis was conducted in the same manner as in Example 1 (4), except that Intermediate 28-2 (4.0 g, 0.008 mol) was added to Intermediate 1-2 (6.0 g, 0.018 mol) 74%).
H-NMR (200MHz, CDCl3):δ ppm, 1H(8.55/d, 8.45/d, 7.94/d, 7.87/d, 7.77/s, 7.69/d, 7.52/m, 7.33/m, 7.30/d, 7.25/m) 2H(8.17/d, 7.98/d, 7.71/d, 7.45/m, 7.36/s) 3H(7.66/s) 4H(7.58/m, 7.42/m) 6H(7.50/d) H-NMR (200MHz, CDCl 3 ): δ ppm, 1H (8.55 / d, 8.45 / d, 7.94 / d, 7.87 / d, 7.77 / s, 7.69 / d, 7.52 / m, 7.33 / m, 7.30 / d M, 7,25 / m) 2H (8.17 / d, 7.98 / d, 7.71 / d, 7.45 / m, 7.36 /
LC/MS: m/z=809 [(M+1)+]
LC / MS: m / z = 809 [(M + 1) < + &
실시예Example 9 : 화합물 31의 합성 9: Synthesis of Compound 31
(1) (One) 제조예Manufacturing example 1 : 중간체 31-1의 합성 1: Synthesis of intermediate 31-1
2-bromo-2'-nitrobiphenyl(5.0 g, 0.017 mol)에 triphenylphosphine(4.5 g, 0.017 mol)에 1,2-dichlorobenzene 100 mL를 넣고 180 ℃에서 24시간 교반하여 반응시켰다. 반응 종료 후 냉각하여 H20:MC에 층분리 후 컬럼정제(n-Hexane:MC)하여 중간체 31-1을 4.2 g (수율 83%)수득하였다.(m/z=246)
100 mL of 1,2-dichlorobenzene was added to triphenylphosphine (4.5 g, 0.017 mol) in 2-bromo-2'-nitrobiphenyl (5.0 g, 0.017 mol) and the mixture was reacted at 180 ° C for 24 hours with stirring. After completion of the reaction, the reaction mixture was cooled, and the product was separated into H 2 O: MC and subjected to column purification (n-hexane: MC) to obtain 4.2 g (m / z = 246)
(2) (2) 제조예Manufacturing example 2 : 중간체 31-2의 합성 2: Synthesis of intermediate 31-2
중간체 31-1(3.0 g, 0.012 mol)에 bromobenzene(1.9 g, 0.012 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <중간체 31-2> 2.9 g (수율 76%)을 얻었다.(m/z=322)
(1.9 g, 0.012 mol) was added to Intermediate 31-1 (3.0 g, 0.012 mol), and 2.9 g (yield: 76%) of Intermediate 31-2 was synthesized in the same manner as in Example 1- %). (M / z = 322)
(3) (3) 제조예Manufacturing example 3 : 중간체 31-3의 합성 3: Synthesis of intermediate 31-3
중간체 31-2(3.0 g, 0.009 mol)에 9H-carbazol-3-ylboronic acid(1.9 g, 0.009 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <중간체 31-3> 3.2 g (수율 79%)을 얻었다.(m/z=452)
Synthesis of Intermediate 31-2 (3.0 g, 0.009 mol) was carried out in the same manner as in Example 1 (1) except that 9H-carbazol-3-ylboronic acid (1.9 g, 0.009 mol) 3> 3.2 g (yield 79%). (M / z = 452)
(4) (4) 제조예Manufacturing example 4 : 중간체 31-4의 합성 4: Synthesis of intermediate 31-4
중간체 1-2(6.0 g, 0.018 mol)에 1,3-dibromo-5-chlorobenzene(2.2 g, 0.008 mol)를 넣고 실시예 1-제조예 (4)에서 사용된 동일한 방법으로 합성하여 <중간체 31-4> 2.9 g (수율 72%)을 얻었다.(m/z=495)
Synthesis was conducted in the same manner as in Example 1 (4), except that 1,3-dibromo-5-chlorobenzene (2.2 g, 0.008 mol) was added to Intermediate 1-2 (6.0 g, 0.018 mol) -4> 2.9 g (yield 72%). (M / z = 495)
(5) (5) 제조예Manufacturing example 5 : 화합물 31의 합성 5: Synthesis of Compound 31
중간체 31-4(5.0 g, 0.010 mol)에 중간체 31-3(3.9 g, 0.008 mol)를 넣고 실시예 1-제조예 (4)에서 사용된 동일한 방법으로 합성하여 <화합물 31> 4.9 g (수율 70%)을 얻었다.Synthesis was conducted in the same manner as in Example 1 (4), except that Intermediate 31-3 (3.9 g, 0.008 mol) was added to Intermediate 31-4 (5.0 g, 0.010 mol) 70%).
H-NMR (200MHz, CDCl3):δ ppm, 1H(7.87/d, 7.77/s, 7.69/d, 7.63/d, 7.37/m, 7.23/d) 2H(8.55/d, 8.17/d, 7.94/d, 7.71/d, 7.36/s, 7.33/m, 7.25/m) 3H(7.66/s, 7.45/m) 4H(7.42/m) 6H(7.58/m, 7.50/d) H-NMR (200MHz, CDCl 3 ): δ ppm, 1H (7.87 / d, 7.77 / s, 7.69 / d, 7.63 / d, 7.37 / m, 7.23 / d) 2H (8.55 / d, 8.17 / d, 7.94 (7.58 / m, 7.50 / d), 7.71 / d, 7.36 / s, 7.33 /
LC/MS: m/z= 868[(M+1)+]
LC / MS: m / z = 868 [(M + 1) < + &
실시예Example 10 : 화합물 42의 합성 10: Synthesis of Compound 42
(1) (One) 제조예Manufacturing example 1 : 중간체 42-1의 합성 1: Synthesis of intermediate 42-1
1,3,5-tribromobenzene(3.4 g, 0.011 mol)에 4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenylboronic acid(4.6 g, 0.013 mol)를 넣고 실시예 1-제조예 (4)에서 사용된 동일한 방법으로 합성하여 <중간체 42-1> 4.3 g (수율 72%)을 얻었다.(m/z=543)
(4,6-diphenyl-1,3,5-triazin-2-yl) phenylboronic acid (4.6 g, 0.013 mol) was added to 1,3,5-tribromobenzene (3.4 g, 0.011 mol) (M / z = 543) (yield: 72%) was obtained by the same method as in the Production Example (4)
(2) (2) 제조예Manufacturing example 2 : 화합물 42의 합성 2: Synthesis of Compound 42
중간체 1-2(6.0 g, 0.018 mol)에 중간체 42-1(4.3 g, 0.008 mol)를 넣고 실시예 1-제조예 (4)에서 사용된 동일한 방법으로 합성하여 <화합물 42> 4.4 g (수율 71%)을 얻었다.Synthesis was conducted in the same manner as in Example 1 (4), except that Intermediate 42-1 (4.3 g, 0.008 mol) was added to Intermediate 1-2 (6.0 g, 0.018 mol) 71%).
H-NMR (200MHz, CDCl3):δ ppm, 2H(8.17/d, 7.87/d, 7.71/d, 7.45/m, 7.41/m, 7.36/s, 7.25/d) 3H(7.66/s) 4H(8.28/d, 7.58/m, 7.51/m, 7.50/d, 7.42/m) H-NMR (200MHz, CDCl 3 ): δ ppm, 2H (8.17 / d, 7.87 / d, 7.71 / d, 7.45 / m, 7.41 / m, 7.36 / s, 7.25 / d) 3H (7.66 / s) 4H (8.28 / d, 7.58 / m, 7.51 / m, 7.50 / d, 7.42 / m)
LC/MS: m/z= 768[(M+1)+]
LC / MS: m / z = 768 [(M + 1) < + &
실시예Example 11 : 화합물 59의 합성 11: Synthesis of Compound 59
(1) (One) 제조예Manufacturing example 1 : 중간체 59-1의 합성 1: Synthesis of intermediate 59-1
중간체 1-2(6.0 g, 0.018 mol)에 1-bromo-3,5-dichlorobenzene(1.8 g, 0.008 mol)를 넣고 실시예 1-제조예 (4)에서 사용된 동일한 방법으로 합성하여 <중간체 59-1> 3.1 g (수율 73%)을 얻었다.(m/z=539)
Synthesis was conducted in the same manner as in Example 1 (4), except that 1-bromo-3,5-dichlorobenzene (1.8 g, 0.008 mol) was added to Intermediate 1-2 (6.0 g, 0.018 mol) -1> 3.1 g (yield: 73%). (M / z = 539)
(2) (2) 제조예Manufacturing example 2 : 중간체 59-2의 합성 2: Synthesis of intermediate 59-2
3,6-dibromo-9H-carbazole(3.0 g, 0.009 mol)에 2-phenyl-1H-imidazo[4,5-d]pyridazine(3.6 g, 0.018 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <중간체 59-2> 3.9 g (수율 78%)을 얻었다.(m/z=555)
(1) was prepared by adding 2-phenyl-1H-imidazo [4,5-d] pyridazine (3.6 g, 0.018 mol) to 3,6-dibromo-9H-carbazole (3.0 g, (M / z = 555) (Intermediate 59-2) (3.9 g, yield 78%).
(3) (3) 제조예Manufacturing example 3 : 화합물 59의 합성 3: Synthesis of Compound 59
중간체 59-1(5.0 g, 0.009 mol)에 중간체 59-2(5.0 g, 0.009 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <화합물 59> 6.9 g (수율 75%)을 얻었다.Synthesis was conducted in the same manner as in Example 1 (1) to obtain Intermediate 59-1 (5.0 g, 0.009 mol) and Intermediate 59-2 (5.0 g, 0.009 mol) 75%).
H-NMR (200MHz, CDCl3):δ ppm, 1H(7.94/d, 7.70/s, 7.63/d, 7.62/d, 7.31/d) 2H(8.17/d, 8.05/s, 7.71/d, 7.50/s, 7.45/m, 7.41/m, 7.36/s) 4H(9.24/s, 8.28/d, 7.58/m, 7.51/m, 7.50/d, 7.42/m) H-NMR (200MHz, CDCl 3 ): δ ppm, 1H (7.94 / d, 7.70 / s, 7.63 / d, 7.62 / d, 7.31 / d) 2H (8.17 / d, 8.05 / s, 7.71 / d, 7.50 7.45 / m, 7.46 / s) 4H (9.24 / s, 8.28 / d, 7.58 / m, 7.51 / m, 7.50 /
LC/MS: m/z= 1015[(M+1)+]
LC / MS: m / z = 1015 [(M + 1) < + &
실시예Example 12 : 화합물 63의 합성 12: Synthesis of Compound 63
(1) (One) 제조예Manufacturing example 1 : 화합물 63의 합성 1: Synthesis of Compound 63
중간체 59-1(5.4 g, 0.010 mol)에 bis(pinacolato)dibron(3.0 g, 0.012 mol)를 넣고 실시예 1-제조예 (2)에서 사용된 동일한 방법으로 합성하여 <중간체 63-1> 4.2 g (수율 72%)을 얻었다.(m/z=586)
Synthesis was conducted in the same manner as in Example 1-Preparation Example (2), except that bis (pinacolato) dibron (3.0 g, 0.012 mol) was added to Intermediate 59-1 (5.4 g, 0.010 mol) g (yield: 72%). (m / z = 586)
(2) (2) 제조예Manufacturing example 2 : 화합물 63의 합성 2: Synthesis of Compound 63
중간체 63-1(5.9 g, 0.010 mol)에 4-(4-bromophenyl)dibenzo[b,d]thiophene (2.7 g, 0.008 mol)를 넣고 실시예 1-제조예 (4)에서 사용된 동일한 방법으로 합성하여 <화합물 63> 4.1 g (수율 72%)을 얻었다.(4-bromophenyl) dibenzo [b, d] thiophene (2.7 g, 0.008 mol) was added to Intermediate 63-1 (5.9 g, 0.010 mol) in the same manner as in Example 1- To obtain 4.1 g (yield 72%) of < Compound 63 >.
H-NMR (200MHz, CDCl3):δ ppm, 1H(8.45/d, 8.41/d, 8.20/d, 7.98/d, 7.58/m, 7.52/m, 7.50/m) 2H(8.17/d, 7.71/d, 7.45/m, 7.36/s) 3H(7.66/s) 4H(7.58/m, 7.50/d, 7.42/m, 7.25/d) H-NMR (200MHz, CDCl 3 ): δ ppm, 1H (8.45 / d, 8.41 / d, 8.20 / d, 7.98 / d, 7.58 / m, 7.52 / m, 7.50 / m) 2H (8.17 / d, 7.71 (7.58 / m, 7.50 / d, 7.42 / m, 7.25 / d)
LC/MS: m/z=719 [(M+1)+]
LC / MS: m / z = 719 [(M + 1) < + &
실시예Example 13 : 화합물 73의 합성 13: Synthesis of Compound 73
(1) (One) 제조예Manufacturing example 1 : 중간체 73-1의 합성 1: Synthesis of intermediate 73-1
3-bromo-5-chloro-1H-indole(3.0 g, 0.013 mol)에 phenyl boronic acid(1.9 g, 0.016 mol)를 넣고 실시예 1-제조예 (4)에서 사용된 동일한 방법으로 합성하여 <중간체 73-1> 2.2 g (수율 73%)을 얻었다.(m/z=227)
Was synthesized in the same manner as in Example 1 (4), except that phenyl boronic acid (1.9 g, 0.016 mol) was added to 3-bromo-5-chloro-1H- indole (3.0 g, 0.013 mol) 73-1> 2.2 g (yield: 73%). (M / z = 227)
(2) (2) 제조예Manufacturing example 2 : 중간체 73-2의 합성 2: Synthesis of Intermediate 73-2
중간체 73-1(3.0 g, 0.013 mol)에 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine(4.5 g, 0.013 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <중간체 73-2> 5.4 g (수율 78%)을 얻었다.(m/z=535)
(4.5 g, 0.013 mol) was added to Intermediate 73-1 (3.0 g, 0.013 mol) in the same manner as in Example 1 (1), except that 2- (4-chlorophenyl) -4,6-diphenyl- ) To obtain 5.4 g (yield 78%) of Intermediate 73-2 (m / z = 535)
(3) (3) 제조예Manufacturing example 3 : 화합물 73의 합성 3: Synthesis of Compound 73
중간체 63-1(5.8 g, 0.010 mol)에 중간체 73-2(4.3 g, 0.008 mol)를 넣고 실시예 1-제조예 (4)에서 사용된 동일한 방법으로 합성하여 <화합물 73> 5.5 g (수율 71%)을 얻었다.Synthesis was conducted in the same manner as in Example 1 (4), except that Intermediate 73-2 (4.3 g, 0.008 mol) was added to Intermediate 63-1 (5.8 g, 0.010 mol) 71%).
H-NMR (200MHz, CDCl3):δ ppm, 1H(8.27/d ,7.77/d ,7.39/s ) 2H(8.17/d ,7.79/d ,7.71/d ,7.68/d ,7.52/d ,7.45/m ) 3H(7.66/s ,7.41/m ,7.36/s ) 4H(8.28/d ,7.58/m ,7.50/d ,7.42/m ) 6H(7.51/m ) H-NMR (200MHz, CDCl 3 ): δ ppm, 1H (8.27 / d, 7.77 / d, 7.39 / s) 2H (8.17 / d, 7.79 / d, 7.71 / d, 7.68 / d, 7.52 / d, 7.45 m) 3H (7.66 / s, 7.41 / m, 7.36 / s) 4H (8.28 / d, 7.58 / m, 7.50 / d, 7.42 /
LC/MS: m/z= 960[(M+1)+]
LC / MS: m / z = 960 [(M + 1) < + &
실시예Example 14 : 화합물 79의 합성 14: Synthesis of Compound 79
(1) (One) 제조예Manufacturing example 1 : 중간체 79-1의 합성 1: Synthesis of intermediate 79-1
1,4-dibromobenzene(2.4 g, 0.010 mol)에 triphenylen-2-ylboronic acid(3.3 g, 0.012 mol)를 넣고 실시예 1-제조예 (4)에서 사용된 동일한 방법으로 합성하여 <중간체 79-1> 2.8 g (수율 72%)을 얻었다.(m/z=383)
2-ylboronic acid (3.3 g, 0.012 mol) was added to 1,4-dibromobenzene (2.4 g, 0.010 mol), and the title compound was synthesized by the same method as in Example 1- > 2.8 g (yield 72%). (M / z = 383)
(2) (2) 제조예Manufacturing example 2 : 중간체 79-2의 합성 2: Synthesis of intermediate 79-2
중간체 1-2(6.0 g, 0.018 mol)에 2,4-dibromo-6-chloro-1,3,5-triazine (2.2 g, 0.008 mol)를 넣고 실시예 1-제조예 (4)에서 사용된 동일한 방법으로 합성하여 <중간체 79-2> 2.8 g (수율 70%)을 얻었다.(m/z=497)
To the intermediate 1-2 (6.0 g, 0.018 mol) was added 2,4-dibromo-6-chloro-1,3,5-triazine (2.2 g, 0.008 mol) (M / z = 497) (Intermediate 79-2) (2.8 g, yield 70%).
(3) (3) 제조예Manufacturing example 3 : 중간체 79-3의 합성 3: Synthesis of intermediate 79-3
중간체 79-2(5.0 g, 0.010 mol)에 bis(pinacolato)dibron(3.0 g, 0.012 mol)를 넣고 실시예 1-제조예 (2)에서 사용된 동일한 방법으로 합성하여 <화합물 79> 4.3 g (수율 73%)을 얻었다.(m/z=589)
4.3 g (Compound 79) was synthesized in the same manner as in Example 1 (2) except that bis (pinacolato) dibron (3.0 g, 0.012 mol) was added to Intermediate 79-2 (5.0 g, 0.010 mol) Yield: 73%). (M / z = 589)
(4) (4) 제조예Manufacturing example 4 : 화합물 79의 합성 4: Synthesis of Compound 79
중간체 79-3(5.9 g, 0.010 mol)에 중간체 79-1(2.8 g, 0.008 mol)를 넣고 실시예 1-제조예 (4)에서 사용된 동일한 방법으로 합성하여 <화합물 79> 4.5 g (수율 73%)을 얻었다.Synthesis was conducted in the same manner as in Example 1 (4), except that Intermediate 79-1 (2.8 g, 0.008 mol) was added to Intermediate 79-3 (5.9 g, 0.010 mol) 73%).
H-NMR (200MHz, CDCl3):δ ppm, 1H(9.15/s, 8.18/d, 8.04/d) 2H(8.93/d, 8.55/d, 8.12/d, 7.94/d, 7.88/m, 7.85/d, 7.82/m, 7.60/s, 7.45/m, 7.33/m, 7.25/d, 7.25/m) 4H(7.58/m, 7.50/d) H-NMR (200MHz, CDCl 3 ): δ ppm, 1H (9.15 / s, 8.18 / d, 8.04 / d) 2H (8.93 / d, 8.55 / d, 8.12 / d, 7.94 / d, 7.88 / m, 7.85 m), 7.45 / m, 7.33 / m, 7.25 / d, 7.25 / m) 4H (7.58 / m, 7.50 /
LC/MS: m/z= 766[(M+1)+]
LC / MS: m / z = 766 [(M + 1) < + &
실시예Example 15 : 화합물 82의 합성 15: Synthesis of Compound 82
(1) (One) 제조예Manufacturing example 1 : 중간체 82-1의 합성 1: Synthesis of intermediate 82-1
중간체 1-2(6.0 g, 0.018 mol)에 2,4,6-tris(4-bromophenyl)-1,3,5-triazine(4.4 g, 0.008 mol)를 넣고 실시예 1-제조예 (4)에서 사용된 동일한 방법으로 합성하여 <중간체 82-1> 4.4 g (수율 72%)을 얻었다.(m/z=770)
(4) was obtained by adding 2,4,6-tris (4-bromophenyl) -1,3,5-triazine (4.4 g, 0.008 mol) to Intermediate 1-2 (6.0 g, (M / z = 770) (yield: 72%). ≪ Synthesis of Intermediate 82-1 &
(2) (2) 제조예Manufacturing example 2 : 화합물 82의 합성 2: Synthesis of Compound (82)
중간체 82-1(5.0 g, 0.006 mol)에 phenyl boronic acid(0.9 g, 0.008 mol)를 넣고 실시예 1-제조예 (4)에서 사용된 동일한 방법으로 합성하여 <화합물 82> 3.5 g (수율 75%)을 얻었다.3.5 g (yield 75%) was prepared by the same method as in Example 1 (4), with phenyl boronic acid (0.9 g, 0.008 mol) added to Intermediate 82-1 (5.0 g, 0.006 mol) %).
H-NMR (200MHz, CDCl3):δ ppm, 2H(8.17/d, 7.85/d, 7.71/d, 7.36/s, 7.25/d) 3H(7.41/m) 4H(7.79/d, 7.68/d, 7.42/m) 6H(7.52/d, 7.51/m) H-NMR (200MHz, CDCl 3 ): δ ppm, 2H (8.17 / d, 7.85 / d, 7.71 / d, 7.36 / s, 7.25 / d) 3H (7.41 / m) 4H (7.79 / d, 7.68 / d , 7.42 / m) 6H (7.52 / d, 7.51 / m)
LC/MS: m/z=768 [(M+1)+]
LC / MS: m / z = 768 [(M + 1) < + &
소자 device
실시예Example
1 : 화합물 1을 1:
ITO로 코팅된 유리기판 위에 NPB를 증착하여 120 nm의 정공수송층을 형성하였으며, 이어서 Ir(ppy)3을 도펀트로 하여 화합물 1의 증착속도를 0.1 nm/sec, Ir(ppy)3를 증착속도 0.009 nm/sec로 증착하고, 증착속도 비율이 9%가 되도록 Ir(ppy)3을 도핑하여 정공수송층 상에 발광층을 30 nm 두께로 형성하였다.NPB was deposited on the ITO coated glass substrate to form a hole transporting layer of 120 nm. Ir (ppy) 3 was used as a dopant to deposit the
그 위에 Balq를 10 nm 두께로 증착하여 정공이 발광층을 지나 전자수송층으로 이동하는 것을 방지하는 정공차단층을 형성하고, 그 위에 Alq3를 증착하여 40 nm의 전자수송층을 형성하였으며, 그 위에 불화리튬을 증착하여 1 nm의 전자주입층을 형성하였다. 전자주입층 상에 알루미늄을 증착하여 120 nm의 음극을 형성하여 유기전계발광소자를 제조하였다.Balq was deposited thereon to a thickness of 10 nm to form a hole blocking layer for preventing holes from moving to the electron transporting layer through the light emitting layer, and Alq 3 was deposited thereon to form an electron transporting layer of 40 nm. Lithium fluoride To form a 1 nm electron injection layer. Aluminum was deposited on the electron injection layer to form a 120 nm negative electrode, thereby fabricating an organic electroluminescent device.
이때, 각 물질의 증착속도는 화합물 1, NPB, Alq3, Balq는 0.1 nm/sec, 불화리튬은 0.01 nm/sec, 알루미늄은 0.5 nm/sec로 하였다.
At this time, the deposition rate of each material was set to
소자 device 실시예Example 2 내지 15 2 to 15
상기 화합물 1 대신 하기 [표 1]에 기재된 화합물을 사용한 것을 제외하고는 소자 실시예 1과 동일한 방법으로 소자실시예 2 내지 15의 유기전계발광소자를 제조하였다.
An organic electroluminescent device of each of the
소자 device 비교예Comparative Example 1 One
소자 비교예 1을 위한 유기발광다이오드 소자는 상기 실시예의 소자구조에서 발명에 의해 제조된 화합물 1 대신 일반적으로 인광호스트 물질로 많이 사용되고 있는 CBP를 사용한 점을 제외하고 동일하게 제작하였다.The organic light emitting diode device for Device Comparison Example 1 was fabricated in the same manner except that CBP, which is generally used as a phosphorescent host material, was used instead of the
상기에서 사용된 Ir(ppy)3, CBP 및 NPB의 구조는 다음과 같다.The structures of Ir (ppy) 3 , CBP and NPB used in the above are as follows.
[표 1][Table 1]
구동전압 및 발광효율 측정Measurement of driving voltage and luminous efficiency
상기 유기전계발광소자(기판크기 : 25×25 ㎟ / 증착면적 : 2×2 ㎟)를 IVL 측정셋트(CS-2000+지그+IVL프로그램)에 고정한 후 전류를 1 mA/㎡씩 상승시키며 증착면의 발광 휘도(cd/㎡), 구동전압(V), 전류밀도(A/㎡), 발광효율(cd/A)을 측정하여 휘도가 1000 cd/㎡일 때 구동전압과 발광효율을 상기 [표 1]에 나타내었다.After fixing the organic electroluminescent device (substrate size: 25 × 25
상기 [표 1]에 따르면, 본 발명에 따른 유기전계발광소자용 화합물이 유기전계발광소자의 발광층의 호스트 물질로 사용될 때 종래의 CBP(호스트재료) 를 사용할 때보다 구동전압은 낮아지고, 발광효율은 증가됨을 볼 수 있다.According to the above Table 1, when the compound for an organic electroluminescence device according to the present invention is used as a host material of a light emitting layer of an organic electroluminescence device, the driving voltage is lower than that of the conventional CBP (host material) Is increased.
Claims (10)
[화학식 1]
상기 [화학식 1]에서,
X1은 CR2R3 또는 NR4이고, X2 내지 X4는 서로 동일하거나 상이하며, 각각 독립적으로 CR5 또는 N이고,
R1 및 상기 R2 내지 R5는 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 30의 알킬기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기, 치환 또는 비치환된 탄소수 5 내지 50의 아릴기, 치환 또는 비치환된 탄소수 2 내지 50의 헤테로아릴기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬이 하나 이상 융합된 치환 또는 비치환된 탄소수 5 내지 50의 아릴기 및 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬이 하나 이상 융합된 치환 또는 비치환된 탄소수 2 내지 50의 헤테로아릴기 중에서 선택되며,
L은 치환 또는 비치환된 탄소수 1 내지 30의 알킬렌기, 치환 또는 비치환된 탄소수 2 내지 30의 알케닐렌기, 치환 또는 비치환된 탄소수 2 내지 30의 알키닐렌기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬렌기, 치환 또는 비치환된 탄소수 5 내지 50의 아릴렌기, 치환 또는 비치환된 탄소수 2 내지 50의 헤테로아릴렌기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬이 하나 이상 융합된 치환 또는 비치환된 탄소수 5 내지 50의 아릴렌기 및 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬이 하나 이상 융합된 치환 또는 비치환된 탄소수 2 내지 50의 헤테로아릴렌기 중에서 선택되며,
n, o 및 p는 각각 독립적으로 1 내지 3의 정수이고, 상기 n, o 및 p가 각각 2 이상인 경우 복수의 L, R1 및 [ ]는 각각 서로 동일하거나 상이하다.An organic light-emitting compound represented by the following Formula 1:
[Chemical Formula 1]
In the above formula (1)
X 1 is CR 2 R 3 or NR 4 , X 2 to X 4 are the same or different and are each independently CR 5 or N,
R 1 and R 2 To R 5 each independently represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted carbon number A substituted or unsubstituted aryl group having 5 to 50 carbon atoms, and a substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms, wherein the substituted or unsubstituted C3 to C30 heteroaryl group, the substituted or unsubstituted C3 to C30 cycloalkyl, Substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms,
L is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted group having 2 to 30 carbon atoms A substituted or unsubstituted C2-C30 alkynylene group, a substituted or unsubstituted C3-C30 A substituted or unsubstituted C2 to C30 heteroarylene group, a substituted or unsubstituted C3 to C30 cycloalkyl, a substituted or unsubstituted C1 to C50 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, A substituted or unsubstituted C2 to C50 heteroarylene group in which one or more substituted or unsubstituted C 3 -C 30 cycloalkyl is fused,
n, o and p are each independently an integer of 1 to 3, and when n, o and p are each 2 or more, a plurality of L, R 1 and [] are the same or different from each other.
상기 L, R1 내지 R5는 각각 독립적으로 1종 이상의 치환기로 더 치환될 수 있고, 상기 1종 이상의 치환기는 수소, 중수소, 치환 또는 비치환된 탄소수 1 내지 30의 알킬기, 치환 또는 비치환된 탄소수 2 내지 30의 알케닐기, 치환 또는 비치환된 탄소수 2 내지 30의 알키닐기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기, 치환 또는 비치환된 탄소수 2 내지 30의 헤테로시클로알킬기, 치환 또는 비치환된 탄소수 5 내지 30의 시클로알케닐기, 치환 또는 비치환된 탄소수 1 내지 30의 알콕시기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴옥시기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬티옥시기, 치환 또는 비치환된 탄소수 5 내지 30의 아릴티옥시기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬아민기, 치환 또는 비치환된 탄소수 5 내지 30의 아릴아민기, 치환 또는 비치환된 탄소수 5 내지 50의 아릴기, 치환 또는 비치환된 탄소수 3 내지 50의 헤테로아릴기, 치환 또는 비치환된 실릴기, 치환 또는 비치환된 게르마늄기, 치환 또는 비치환된 붕소기, 치환 또는 비치환된 알루미늄기, 카르보닐기, 포스포릴기, 아미노기, 싸이올기, 시아노기, 히드록시기, 니트로기, 할로겐기, 셀레늄기, 텔루륨기, 아미드기, 에테르기 및 에스테르기 중에서 선택되는 것을 특징으로 하는 유기발광 화합물.The method according to claim 1,
The L, R < 1 > R 5 may be independently substituted with at least one substituent, and the at least one substituent may be selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms Substituted or unsubstituted C2-C30 alkynyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C2-C30 heterocycloalkyl, substituted or unsubstituted C5- A substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C1-C30 alkoxy group, A substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 30 carbon atoms, A substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted germanium group, a substituted or unsubstituted boron group, An organic group which is selected from the group consisting of a halogen atom, a hydroxyl group, a halogen atom, a selenium atom, a tellurium atom, an amide group, an ether group and an ester group compound.
상기 L, R1 내지 R5 및 이들의 치환기는 서로 결합하거나 인접한 치환기와 연결되어 지환족, 방향족의 단일환 또는 다환 고리를 형성할 수 있으며, 상기 형성된 지환족, 방향족의 단일환 또는 다환 고리의 탄소원자는 N, S 및 O 중에서 선택되는 어느 하나 이상의 헤테로원자로 치환될 수 있는 것을 특징으로 하는 유기발광 화합물.The method according to claim 1,
The L, R < 1 > R 5 and the substituents thereof may be bonded to each other or may be connected with adjacent substituents to form a single alicyclic or aromatic ring or polycyclic ring, and the carbon atom of the alicyclic or aromatic monocyclic or polycyclic ring formed may be N, S, And R < 2 > are each independently selected from the group consisting of hydrogen, fluorine, chlorine, bromine, and iodine.
상기 L은 각각 독립적으로 하기 [구조식 1] 중에서 선택되는 것을 특징으로 하는 유기발광 화합물:
[구조식 1]
상기 [구조식 1]에서,
Z는 CR6, NR7, CR8R9, SiR10R11, GeR12R13, PR14, BR15, Te, O 및 S 중에서 선택되고, 상기 R6 내지 R15는 수소, 중수소, 할로겐기, 시아노기, 히드록실기, 니트로기, 아미노기, 치환 또는 비치환된 탄소수 1 내지 60의 알킬기, 치환 또는 비치환된 탄소수 3 내지 60의 시클로알킬기, 치환 또는 비치환된 탄소수 6 내지 60의 아릴기, 치환 또는 비치환된 탄소수 3 내지 60의 헤테로아릴기, 치환 또는 비치환된 탄소수 1 내지 60의 알콕시기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴옥시기, 치환 또는 비치환된 탄소수 1 내지 20의 알킬아미노기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴아미노기, 치환 또는 비치환된 탄소수 1 내지 20의 알킬실릴기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴실릴기, 치환 또는 비치환된 탄소수 1 내지 50의 아릴알킬아미노기, 치환 또는 비치환된 탄소수 5 내지 60의 아릴싸이오기, 치환 또는 비치환된 탄소수 2 내지 60의 알케닐기 및 치환 또는 비치환된 탄소수 2 내지 60의 알키닐기 중에서 선택되며,
상기 R1 내지 R10 및 이들의 치환기는 서로 결합하거나 인접한 치환기와 연결되어 지환족, 방향족의 단일환 또는 다환 고리를 형성할 수 있으며, 상기 형성된 지환족, 방향족의 단일환 또는 다환 고리의 탄소원자는 N, S 및 O 중에서 선택되는 어느 하나 이상의 헤테로원자로 치환될수 있다.The method according to claim 1,
Wherein each L is independently selected from the following structural formula 1:
[Structural formula 1]
In the above formula 1,
Z is selected from the group consisting of CR 6 , NR 7 , CR 8 R 9 , SiR 10 R 11 , GeR 12 R 13 , PR 14 , BR 15 , Te, O and S, and R 6 to R 15 are selected from the group consisting of hydrogen, A substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C3-C60 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryl group, A substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1- A substituted or unsubstituted C1-C20 alkylamino group, a substituted or unsubstituted C6-C30 arylamino group, a substituted or unsubstituted C1-C20 alkylsilyl group, a substituted or unsubstituted C6-C30 arylsilyl group, A substituted arylalkylamino group having 1 to 50 carbon atoms, a substituted Or an unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, and a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms,
The R 1 to R 10 and substituents thereof may be bonded to each other or may be connected with adjacent substituents to form a single alicyclic or aromatic ring or polycyclic ring. The carbon atom of the formed alicyclic or aromatic monocyclic or polycyclic ring may be a N, S, and O. The term " heteroaryl "
상기 [화학식 1]은 하기 [화합물 1] 내지 [화합물 82] 중에서 선택되는 것을 특징으로 하는 유기발광 화합물:
The organic electroluminescent compound according to claim 1, wherein the organic electroluminescent compound is selected from the following compounds [1] to [82]:
상기 유기물층 중 1 층 이상은 제1항에 따른 [화학식 1]의 유기발광 화합물을 포함하는 것을 특징으로 하는 유기전계발광소자.1. An organic electroluminescent device comprising a first electrode, a second electrode, and at least one organic material layer disposed between the first electrode and the second electrode,
Wherein at least one of the organic material layers comprises an organic light emitting compound represented by Formula 1 according to Claim 1.
상기 유기물층은 정공 주입층, 정공 수송층, 정공 주입 및 정공 수송을 동시에 하는 층, 전자 수송층, 전자 주입층, 전자 수송 및 전자 주입을 동시에 하는 층 및 발광층 중 1층 이상을 포함하고, 상기 층들 중 1층 이상이 상기 [화학식 1]로 표시되는 유기발광 화합물을 포함하는 것을 특징으로 하는 유기전계발광소자.The method according to claim 6,
Wherein the organic material layer includes at least one of a hole injecting layer, a hole transporting layer, a hole injecting and transporting layer, an electron transporting layer, an electron injecting layer, a layer simultaneously performing electron transport and electron injection, and a light emitting layer, Wherein at least one layer comprises an organic light-emitting compound represented by the above formula (1).
상기 발광층이 상기 [화학식 1]로 표시되는 유기발광 화합물을 포함하는 것을 특징으로 하는 유기전계발광소자.8. The method of claim 7,
Wherein the light emitting layer comprises an organic light emitting compound represented by the following formula (1).
상기 [화학식 1]로 표시되는 유기발광 화합물은 상기 발광층 내의 호스트 화합물로 사용되고, 상기 발광층은 도판트 화합물을 1종 이상 더 포함하는 것을 특징으로 하는 유기전계발광소자.9. The method of claim 8,
The organic electroluminescent compound represented by Formula 1 is used as a host compound in the light emitting layer, and the light emitting layer further includes at least one dopant compound.
상기 유기물층에 적색, 녹색 또는 청색 발광을 하는 유기 발광층을 하나 이상을 더 포함하여 백색 발광을 하는 것을 특징으로 하는 유기전계발광소자.The method according to claim 6,
Wherein at least one of the organic light emitting layers emitting red, green or blue light is further included in the organic material layer to emit white light.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020140064831A KR101666826B1 (en) | 2014-05-29 | 2014-05-29 | An electroluminescent compound and an electroluminescent device comprising the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020140064831A KR101666826B1 (en) | 2014-05-29 | 2014-05-29 | An electroluminescent compound and an electroluminescent device comprising the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20150137265A true KR20150137265A (en) | 2015-12-09 |
| KR101666826B1 KR101666826B1 (en) | 2016-10-17 |
Family
ID=54873218
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020140064831A KR101666826B1 (en) | 2014-05-29 | 2014-05-29 | An electroluminescent compound and an electroluminescent device comprising the same |
Country Status (1)
| Country | Link |
|---|---|
| KR (1) | KR101666826B1 (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108997322A (en) * | 2018-09-25 | 2018-12-14 | 武汉天马微电子有限公司 | Nitrogen heterocyclic, display panel and display device |
| JP2019518716A (en) * | 2017-04-20 | 2019-07-04 | ジャンスー スネラ テクノロジー カンパニー リミテッドＪｉａｎｇｓｕ Ｓｕｎｅｒａ Ｔｅｃｈｎｏｌｏｇｙ Ｃｏ．，Ｌｔｄ | Organic compound having triazine and benzimidazole core and organic electroluminescent device using the compound |
| CN110452226A (en) * | 2019-08-05 | 2019-11-15 | 北京大学深圳研究生院 | A kind of organic blue-light fluorescent material and blue-light device based on azole derivatives |
| CN110669051A (en) * | 2019-09-30 | 2020-01-10 | 上海天马有机发光显示技术有限公司 | Compound, display panel and display device |
| CN110746405A (en) * | 2018-12-14 | 2020-02-04 | 广州华睿光电材料有限公司 | Pyrrole group-containing compound and application thereof in organic electronic device |
| CN110790754A (en) * | 2018-08-02 | 2020-02-14 | 昱镭光电科技股份有限公司 | Organic light-emitting device capable of generating light-emitting exciplex |
| JP2020138924A (en) * | 2019-02-27 | 2020-09-03 | 学校法人明治大学 | Compound and production method thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20110115887A (en) * | 2010-04-16 | 2011-10-24 | 에스에프씨 주식회사 | Amine-based compound and organic electroluminescent devices comprising the same |
| KR20130115161A (en) * | 2012-04-10 | 2013-10-21 | 에스에프씨 주식회사 | Heterocyclic com pounds and organic light-emitting diode including the same |
| KR20130142968A (en) * | 2012-06-20 | 2013-12-30 | 에스에프씨 주식회사 | Heterocyclic compounds and organic light-emitting diode including the same |
| KR20130142969A (en) * | 2012-06-20 | 2013-12-30 | 에스에프씨 주식회사 | Heterocyclic compounds and organic light-emitting diode including the same |
-
2014
- 2014-05-29 KR KR1020140064831A patent/KR101666826B1/en active IP Right Grant
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20110115887A (en) * | 2010-04-16 | 2011-10-24 | 에스에프씨 주식회사 | Amine-based compound and organic electroluminescent devices comprising the same |
| KR20130115161A (en) * | 2012-04-10 | 2013-10-21 | 에스에프씨 주식회사 | Heterocyclic com pounds and organic light-emitting diode including the same |
| KR20130142968A (en) * | 2012-06-20 | 2013-12-30 | 에스에프씨 주식회사 | Heterocyclic compounds and organic light-emitting diode including the same |
| KR20130142969A (en) * | 2012-06-20 | 2013-12-30 | 에스에프씨 주식회사 | Heterocyclic compounds and organic light-emitting diode including the same |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2019518716A (en) * | 2017-04-20 | 2019-07-04 | ジャンスー スネラ テクノロジー カンパニー リミテッドＪｉａｎｇｓｕ Ｓｕｎｅｒａ Ｔｅｃｈｎｏｌｏｇｙ Ｃｏ．，Ｌｔｄ | Organic compound having triazine and benzimidazole core and organic electroluminescent device using the compound |
| CN110790754A (en) * | 2018-08-02 | 2020-02-14 | 昱镭光电科技股份有限公司 | Organic light-emitting device capable of generating light-emitting exciplex |
| CN108997322A (en) * | 2018-09-25 | 2018-12-14 | 武汉天马微电子有限公司 | Nitrogen heterocyclic, display panel and display device |
| CN110746405A (en) * | 2018-12-14 | 2020-02-04 | 广州华睿光电材料有限公司 | Pyrrole group-containing compound and application thereof in organic electronic device |
| JP2020138924A (en) * | 2019-02-27 | 2020-09-03 | 学校法人明治大学 | Compound and production method thereof |
| CN110452226A (en) * | 2019-08-05 | 2019-11-15 | 北京大学深圳研究生院 | A kind of organic blue-light fluorescent material and blue-light device based on azole derivatives |
| CN110669051A (en) * | 2019-09-30 | 2020-01-10 | 上海天马有机发光显示技术有限公司 | Compound, display panel and display device |
Also Published As
| Publication number | Publication date |
|---|---|
| KR101666826B1 (en) | 2016-10-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR101825405B1 (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR101530266B1 (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR101852926B1 (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR101627691B1 (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR20170082459A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR101842013B1 (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR101626524B1 (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR101666826B1 (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR20160127429A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR101790550B1 (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR20160066308A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR101627695B1 (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR20150110101A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR101837048B1 (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR20160054870A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR101713530B1 (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR20170003472A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR20170003471A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR20160006007A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR102316570B1 (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR20180042943A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR101627693B1 (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR20180042967A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR20180042966A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR20170003470A (en) | An electroluminescent compound and an electroluminescent device comprising the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A201 | Request for examination | ||
| E902 | Notification of reason for refusal | ||
| E701 | Decision to grant or registration of patent right | ||
| GRNT | Written decision to grant |