KR20130011405A - Novel organic electroluminescence compounds and organic electroluminescence device using the same - Google Patents
Novel organic electroluminescence compounds and organic electroluminescence device using the same Download PDFInfo
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- KR20130011405A KR20130011405A KR1020110072545A KR20110072545A KR20130011405A KR 20130011405 A KR20130011405 A KR 20130011405A KR 1020110072545 A KR1020110072545 A KR 1020110072545A KR 20110072545 A KR20110072545 A KR 20110072545A KR 20130011405 A KR20130011405 A KR 20130011405A
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- South Korea
- Prior art keywords
- substituted
- unsubstituted
- alkyl
- aryl
- heteroaryl
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 118
- 238000005401 electroluminescence Methods 0.000 title abstract description 6
- -1 N-carbazolyl Chemical group 0.000 claims abstract description 71
- 125000003118 aryl group Chemical group 0.000 claims abstract description 68
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims abstract description 64
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 45
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 36
- 150000002367 halogens Chemical class 0.000 claims abstract description 36
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims abstract description 29
- 229910052805 deuterium Inorganic materials 0.000 claims abstract description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 26
- 239000001257 hydrogen Substances 0.000 claims abstract description 26
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 25
- 125000005549 heteroarylene group Chemical group 0.000 claims abstract description 8
- 125000000732 arylene group Chemical group 0.000 claims abstract description 7
- 125000002993 cycloalkylene group Chemical group 0.000 claims abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 239000002019 doping agent Substances 0.000 claims description 15
- 125000002950 monocyclic group Chemical group 0.000 claims description 15
- 125000002723 alicyclic group Chemical group 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000003367 polycyclic group Chemical group 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 125000004450 alkenylene group Chemical group 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000001769 aryl amino group Chemical group 0.000 claims description 10
- 125000005104 aryl silyl group Chemical group 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
- 229910052717 sulfur Chemical group 0.000 claims description 9
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 239000011368 organic material Substances 0.000 claims description 8
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 239000001301 oxygen Chemical group 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 229910052796 boron Inorganic materials 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000006413 ring segment Chemical group 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 229910052741 iridium Inorganic materials 0.000 claims description 2
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 2
- 150000002602 lanthanoids Chemical class 0.000 claims description 2
- 239000003446 ligand Substances 0.000 claims description 2
- 229910052762 osmium Inorganic materials 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 125000003003 spiro group Chemical group 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 229910052723 transition metal Inorganic materials 0.000 claims description 2
- 150000003624 transition metals Chemical class 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 abstract description 34
- 239000000463 material Substances 0.000 abstract description 33
- 239000000126 substance Substances 0.000 abstract description 6
- 239000010410 layer Substances 0.000 description 41
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 238000002360 preparation method Methods 0.000 description 12
- 239000012044 organic layer Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 9
- 239000012153 distilled water Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 6
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 5
- 0 C*C(*)(c1c2)c3c(*)c(*)c(**)c(*)c3-c1cc(C)c2-c1nc2c(C)c(C)c(*)c(*)c2c(*)c1* Chemical compound C*C(*)(c1c2)c3c(*)c(*)c(**)c(*)c3-c1cc(C)c2-c1nc2c(C)c(C)c(*)c(*)c2c(*)c1* 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- QBYJBZPUGVGKQQ-SJJAEHHWSA-N aldrin Chemical compound C1[C@H]2C=C[C@@H]1[C@H]1[C@@](C3(Cl)Cl)(Cl)C(Cl)=C(Cl)[C@@]3(Cl)[C@H]12 QBYJBZPUGVGKQQ-SJJAEHHWSA-N 0.000 description 4
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 4
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- 239000011259 mixed solution Substances 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 125000001725 pyrenyl group Chemical group 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 4
- 238000001771 vacuum deposition Methods 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- POFVJRKJJBFPII-UHFFFAOYSA-N N-cyclopentyl-5-[2-[[5-[(4-ethylpiperazin-1-yl)methyl]pyridin-2-yl]amino]-5-fluoropyrimidin-4-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound C1(CCCC1)NC=1SC(=C(N=1)C)C1=NC(=NC=C1F)NC1=NC=C(C=C1)CN1CCN(CC1)CC POFVJRKJJBFPII-UHFFFAOYSA-N 0.000 description 3
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 3
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 3
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 3
- 125000005872 benzooxazolyl group Chemical group 0.000 description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 3
- 150000004770 chalcogenides Chemical class 0.000 description 3
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- GOXNHPQCCUVWRO-UHFFFAOYSA-N dibenzothiophen-4-ylboronic acid Chemical compound C12=CC=CC=C2SC2=C1C=CC=C2B(O)O GOXNHPQCCUVWRO-UHFFFAOYSA-N 0.000 description 3
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000002541 furyl group Chemical group 0.000 description 3
- 125000002883 imidazolyl group Chemical group 0.000 description 3
- 125000001041 indolyl group Chemical group 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000002971 oxazolyl group Chemical group 0.000 description 3
- 125000000913 palmityl 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])C([H])([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 3
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 3
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 3
- 125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 description 3
- 239000008213 purified water Substances 0.000 description 3
- 125000003226 pyrazolyl group Chemical group 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 125000000168 pyrrolyl group Chemical group 0.000 description 3
- 125000005493 quinolyl group Chemical group 0.000 description 3
- 230000027756 respiratory electron transport chain Effects 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 125000000335 thiazolyl group Chemical group 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- ORPVVAKYSXQCJI-UHFFFAOYSA-N 1-bromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Br ORPVVAKYSXQCJI-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- BTTNYQZNBZNDOR-UHFFFAOYSA-N 2,4-dichloropyrimidine Chemical compound ClC1=CC=NC(Cl)=N1 BTTNYQZNBZNDOR-UHFFFAOYSA-N 0.000 description 2
- NXTRQJAJPCXJPY-UHFFFAOYSA-N 910058-11-6 Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C2=CC=CC=C2C=CC=1)C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1 NXTRQJAJPCXJPY-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 150000001204 N-oxides Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000004429 atom 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
- 230000000903 blocking effect Effects 0.000 description 2
- 239000010779 crude oil Substances 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- OMRRUNXAWXNVFW-UHFFFAOYSA-N fluoridochlorine Chemical compound ClF OMRRUNXAWXNVFW-UHFFFAOYSA-N 0.000 description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000002098 pyridazinyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 150000002910 rare earth metals Chemical class 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 2
- 125000004306 triazinyl group Chemical group 0.000 description 2
- IDQUIFLAFFZYEX-UHFFFAOYSA-N (3-carbazol-9-ylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=C1 IDQUIFLAFFZYEX-UHFFFAOYSA-N 0.000 description 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- 125000006651 (C3-C20) cycloalkyl group Chemical group 0.000 description 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 1
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 1
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 description 1
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- MBHPOBSZPYEADG-UHFFFAOYSA-N 2-bromo-9,9-dimethylfluorene Chemical compound C1=C(Br)C=C2C(C)(C)C3=CC=CC=C3C2=C1 MBHPOBSZPYEADG-UHFFFAOYSA-N 0.000 description 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 1
- YXVFYQXJAXKLAK-UHFFFAOYSA-M 4-phenylphenolate Chemical compound C1=CC([O-])=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-M 0.000 description 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 1
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- 230000009477 glass transition Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical class [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
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- 239000002480 mineral oil Substances 0.000 description 1
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- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
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- 125000005565 oxadiazolylene group Chemical group 0.000 description 1
- 125000005564 oxazolylene group Chemical group 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000005548 pyrenylene group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
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- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000005557 thiazolylene group Chemical group 0.000 description 1
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- 125000005730 thiophenylene group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000005559 triazolylene group 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
- 238000002061 vacuum sublimation Methods 0.000 description 1
Classifications
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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
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- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
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- C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
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Abstract
Description
본 발명은 신규한 유기 발광 화합물 및 이를 포함하고 있는 유기 전계 발광 소자 에 관한 것이다.The present invention relates to a novel organic light emitting compound and an organic electroluminescent device comprising the same.
표시 소자 중, 전기 발광 소자(electroluminescence device: EL device)는 자체 발광형 표시 소자로서 시야각이 넓고 콘트라스트가 우수할 뿐만 아니라 응답속도가 빠르다는 장점을 가지고 있다. 1987년 이스트만 코닥(Eastman Kodak)사는 발광층 형성용 재료로서 저분자인 방향족 디아민과 알루미늄 착물을 이용하고 있는 유기 EL 소자를 처음으로 개발하였다[Appl. Phys. Lett. 51, 913, 1987].Among the display elements, an electroluminescence device (EL device) is a self-luminous display element and has advantages of wide viewing angle, excellent contrast, and fast response speed. In 1987, Eastman Kodak developed for the first time an organic EL device using a low molecular weight aromatic diamine and an aluminum complex as a material for forming a light emitting layer [Appl. Phys. Lett. 51, 913, 1987].
OLED에서 발광 효율을 결정하는 가장 중요한 요인은 발광 재료이다. 발광 재료로는 현재까지 형광 재료가 널리 사용되고 있으나, 전기발광의 메커니즘 상 인광 재료의 개발은 이론적으로 4배까지 발광 효율을 개선시킬 수 있는 가장 좋은 방법 중 하나이다. 현재까지 이리듐(III)착물 계열이 인광 발광 재료로 널리 알려져 있으며, 각 RGB 별로는 (acac)Ir(btp)2, Ir(ppy)3 및 Firpic 등의 재료가 알려져 있다. 특히, 최근 일본, 구미에서 많은 인광 재료들이 연구되고 있다. The most important factor determining the luminous efficiency in OLEDs is the luminous material. Fluorescent materials are widely used as the light emitting materials to date, but the development of phosphorescent materials is one of the best ways to improve the luminous efficiency theoretically up to 4 times. To date, iridium (III) complexes are widely known as phosphorescent materials, and for each RGB, materials such as (acac) Ir (btp) 2 , Ir (ppy) 3, and Firpic are known. In particular, many phosphorescent materials have recently been studied in Japan and Europe.
인광 발광체의 호스트 재료로는 현재까지 CBP가 가장 널리 알려져 있고, BCP 및 BAlq 등의 정공차단층을 적용한 고효율의 OLED가 공지되어 있으며, 일본의 파이오니어 등에서는 BAlq 유도체를 호스트로 이용해 고성능의 OLED을 개발한 바 있다. CBP is the most widely known host material for phosphorescent emitters to date, and high-efficiency OLEDs using hole blocking layers such as BCP and BAlq are known. I've done it.
그러나 기존의 재료들은 발광 특성 측면에서는 유리한 면이 있으나, 유리전이온도가 낮고 열적 안정성이 매우 좋지 않아서, 진공 하에서 고온 증착 공정을 거칠 때, 물질이 변하는 단점을 갖고 있다. OLED에서 전력효율 = [(π/전압) × 전류효율]의 관계에 있으므로 전력효율은 전압에 반비례하고, 따라서 OLED의 소비 전력을 낮으려면 전력 효율을 높여야 한다. 실제 인광 발광 재료를 사용한 OLED는 형광 발광 재료를 사용한 OLED에 비해 전류 효율(cd/A)이 상당히 높으나, 인광 발광 재료의 호스트로 사용되던 BAlq 또는 CBP와 같은 종래재료의 경우, 형광재료를 사용한 OLED에 비해 구동 전압이 높아서 전력 효율(lm/w)면에서 큰 이점이 없었다. 또한, OLED 소자에 사용할 경우 수명 측면에서도 결코 만족스럽지 못하였다.However, existing materials have advantages in terms of luminescence properties, but the glass transition temperature is low and the thermal stability is not very good, so that the material changes when undergoing a high temperature deposition process under vacuum. In the OLED, power efficiency = [(π / voltage) × current efficiency], so power efficiency is inversely proportional to voltage. Therefore, to lower the power consumption of the OLED, power efficiency must be increased. In fact, OLEDs using phosphorescent materials have considerably higher current efficiency (cd / A) than OLEDs using fluorescent materials, but in the case of conventional materials such as BAlq or CBP used as a host of phosphorescent materials, OLEDs using fluorescent materials Compared with the higher driving voltage, there was no significant advantage in terms of power efficiency (lm / w). Also, when used in OLED devices, they were never satisfactory in terms of lifetime.
한편, 한국특허공보 제 KR0948700호에는 아릴카바졸기 골격에 질소를 포함하는 헤테로아릴이 치환된 유기전기발광 소자용 화합물을 언급하고 있다. 그러나 상기문헌에는 융합된 카바졸골격의 질소위치에 카바졸기가 치환된 헤테로아릴이 직접 또는 간접적으로 연결된 화합물을 구체적으로 개시하고 있지 않다. Meanwhile, Korean Patent Publication No. KR0948700 refers to a compound for an organic electroluminescent device in which a heteroaryl containing nitrogen is substituted in an arylcarbazole group skeleton. However, this document does not specifically disclose a compound in which a heteroaryl substituted with a carbazole group at a nitrogen position of a fused carbazole skeleton is directly or indirectly connected.
따라서 본 발명의 목적은 첫째로, 상기한 문제점들을 해결하기 위하여 기존의 재료보다 발광 효율 및 소자 수명이 좋으며, 적절한 색좌표를 갖는 우수한 골격의 유기 발광 화합물을 제공하는 것이며 둘째로, 상기 유기 발광 화합물을 발광 재료로서 채용하는 고효율 및 장수명의 유기 전계 발광 소자를 제공하는 것이다. Accordingly, an object of the present invention is to firstly provide an organic light emitting compound having excellent luminous efficiency and device life, and having an appropriate color coordinate, in order to solve the above problems, and secondly, to solve the above organic light emitting compound. It is to provide a high efficiency and long life organic electroluminescent element employed as a light emitting material.
본 발명은 하기 화학식 1로 표시되는 유기 발광 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것으로서, 본 발명에 따른 유기 발광 화합물은 기존 재료에 비해 발광 효율이 좋고 재료의 수명특성이 뛰어나 소자의 구동수명이 매우 우수할 뿐만 아니라 전력효율의 상승을 유도하여 소비전력이 개선된 OLED 소자를 제조할 수 있는 장점이 있다.The present invention relates to an organic light emitting compound represented by the following Chemical Formula 1 and an organic electroluminescent device comprising the same, the organic light emitting compound according to the present invention has better light emission efficiency and excellent life characteristics of the material than the existing material, the driving life of the device This is not only very good, but also has an advantage of manufacturing an OLED device with improved power consumption by inducing an increase in power efficiency.
[화학식 1] [Formula 1]
[상기 화학식 1에서,[In Formula 1,
L1 및 L2은 각각 독립적으로 단일결합, 치환 또는 비치환된 (C2-C30)헤테로아릴렌, 치환 또는 비치환된 (C6-C30)아릴렌, 또는 치환 또는 비치환된 (C3-C30)시클로알킬렌이고;L 1 and L 2 are each independently a single bond, substituted or unsubstituted (C2-C30) heteroarylene, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (C3-C30) Cycloalkylene;
X1 및 X2은 각각 독립적으로 CH 또는 N이며;X 1 and X 2 are Each one independently CH or N;
Y1 및 Y2는 각각 독립적으로 -O-, -S-, -CR5R6- 또는 -NR7-이며, 단, Y2 와 Y3가 동시에 존재하는 경우는 없고;Y 1 and Y 2 are each independently -O-, -S-, -CR 5 R 6 -or -NR 7- , provided that Y 2 and Y 3 are not present at the same time;
Ar은 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (C2-C30)헤테로아릴, 또는 N-카바졸릴이며;Ar is each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C2-C30) heteroaryl, or N Carbazolyl;
R1 내지 R4은 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (C2-C30)헤테로아릴, 치환 또는 비치환된 (C3-C30)시클로알킬, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된 (C6-C30)아르(C1-C30)알킬, -NR11R12, -SiR13R14R15, -SR16, -OR17 , 시아노, 나이트로 또는 하이드록시이거나, 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 치환 또는 비치환된 (C3-C30)알킬렌 또는 치환 또는 비치환된 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있으며, 상기 형성된 지환족 고리 및 단일환 또는 다환의 방향족 고리의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 치환될 수 있고;R 1 to R 4 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C2-C30) hetero Aryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C6-C30) ar (C1-C30) alkyl, -NR 11 R 12 , -SiR 13 R 14 R 15 , -SR 16 , -OR 17 , cyano, nitro or hydroxy, substituted or unsubstituted (C3-C30) with or without adjacent substituents and fused rings Alkylene or substituted or unsubstituted (C3-C30) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, and the alicyclic ring and the monocyclic or polycyclic aromatic ring The carbon atom may be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur;
R5 내지 R7 및 R11 내지 R17는 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (C2-C30)헤테로아릴, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된 (C3-C30)시클로알킬이거나, 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 치환 또는 비치환된 (C3-C30)알킬렌 또는 치환 또는 비치환된 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있으며, 상기 형성된 지환족 고리 및 단일환 또는 다환의 방향족 고리의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 치환될 수 있고;R 5 to R 7 and R 11 to R 17 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C2-C30) heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C3-C30) cycloalkyl, or a substitution with or without a fused ring with adjacent substituents, or May be linked to an unsubstituted (C3-C30) alkylene or substituted or unsubstituted (C3-C30) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, wherein the alicyclic ring and Carbon atoms of monocyclic or polycyclic aromatic rings may be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur;
a, b, c 및 d는 각각 독립적으로 1 내지 4의 정수이며, 2 이상의 정수인 경우 각각 동일하거나 상이할 수 있고;a, b, c, and d are each independently an integer of 1 to 4, and when integers of 2 or more, each may be the same or different;
상기 헤테로시클로알킬, 헤테로아릴렌 및 헤테로아릴은 B, N, O, S, P(=O), Si 및 P로부터 선택된 하나 이상의 헤테로원자를 포함한다.]
Wherein said heterocycloalkyl, heteroarylene and heteroaryl include one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P.]
본 발명에 기재된 「알킬」, 「알콕시」 및 그 외 「알킬」부분을 포함하는 치환체는 직쇄 또는 분쇄 형태를 모두 포함하고, 「시클로알킬」은 단일 고리계 뿐만 아니라 치환 또는 비치환된 아다만틸 또는 치환 또는 비치환된 (C7-C30)바이시클로알킬과 같은 여러 고리계 탄화수소도 포함한다. 본 발명에 기재된 「아릴」은 하나의 수소 제거에 의해서 방향족 탄화수소로부터 유도된 유기 라디칼로, 각 고리에 적절하게는 4 내지 7개, 바람직하게는 5 또는 6개의 고리원자를 포함하는 단일 또는 융합고리계를 포함하며, 다수개의 아릴이 단일결합으로 연결되어 있는 형태까지 포함한다. 구체적인 예로서 페닐, 나프틸, 비페닐, 터페닐, 안트릴, 인데닐(indenyl), 플루오레닐, 페난트릴, 트리페닐레닐, 피렌일, 페릴렌일, 크라이세닐, 나프타세닐, 플루오란텐일 등이 있다. 상기 나프틸은 1-나프틸 및 2-나프틸을 포함하며, 안트릴은 1-안트릴, 2-안트릴 및 9-안트릴을 포함하며, 플루오레닐은 1-플루오레닐, 2-플루오레닐, 3-플루오레닐, 4-플루오레닐 및 9-플루오레닐을 모두 포함한다. 본 발명에 기재된 「헤테로아릴」은 방향족 고리 골격 원자로서 B, N, O, S, P(=O), Si 및 P로부터 선택되는 1 내지 4개의 헤테로원자를 포함하고 나머지 방향족 고리 골격 원자가 탄소인 아릴 그룹을 의미하는 것으로, 5 내지 6원 단환 헤테로아릴, 및 하나 이상의 벤젠 환과 축합된 다환식 헤테로아릴이며, 부분적으로 포화될 수도 있다. 또한, 본 발명에서의 헤테로아릴은 하나 이상의 헤테로아릴이 단일결합으로 연결된 형태도 포함한다. 상기 헤테로아릴기는 고리내 헤테로원자가 산화되거나 사원화되어, 예를 들어 N-옥사이드 또는 4차 염을 형성하는 2가 아릴 그룹을 포함한다. 구체적인 예로서 퓨릴, 티오펜일, 피롤릴, 이미다졸릴, 피라졸릴, 티아졸릴, 티아디아졸릴, 이소티아졸릴, 이속사졸릴, 옥사졸릴, 옥사디아졸릴, 트리아진일, 테트라진일, 트리아졸릴, 퓨라잔일, 피리딜, 피라진일, 피리미딘일, 피리다진일 등의 단환 헤테로아릴, 벤조퓨란일, 벤조티오펜일, 이소벤조퓨란일, 벤조이미다졸릴, 벤조티아졸릴, 벤조이소티아졸릴, 벤조이속사졸릴, 벤조옥사졸릴, 이소인돌릴, 인돌릴, 인다졸릴, 벤조티아디아졸릴, 퀴놀릴, 이소퀴놀릴, 신놀리닐, 퀴나졸리닐, 퀴녹살리닐, 카바졸릴, 페난트리딘일, 벤조디옥솔릴, 다이벤조퓨란닐, 다이벤조싸이오페닐 등의 다환식 헤테로아릴 및 이들의 상응하는 N-옥사이드(예를 들어, 피리딜 N-옥사이드, 퀴놀릴 N-옥사이드), 이들의 4차 염 등을 들수 있다.Substituents including the "alkyl", "alkoxy" and other "alkyl" moieties described herein include all linear or pulverized forms, and "cycloalkyl" is not only a monocyclic system but also substituted or unsubstituted adamantyl Or several ring-based hydrocarbons such as substituted or unsubstituted (C7-C30) bicycloalkyl. "Aryl" described in the present invention is an organic radical derived from an aromatic hydrocarbon by one hydrogen removal, and a single or fused ring containing 4 to 7, preferably 5 or 6 ring atoms in each ring as appropriate. It includes a system, including a form in which a plurality of aryl is connected by a single bond. Specific examples include phenyl, naphthyl, biphenyl, terphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, peryleneyl, chrysenyl, naphthacenyl, fluoranthenyl and the like. There is this. Said naphthyl includes 1-naphthyl and 2-naphthyl, anthryl includes 1-anthryl, 2-anthryl and 9-anthryl, and fluorenyl is 1-fluorenyl, 2- Fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl. "Heteroaryl" described in the present invention contains 1 to 4 heteroatoms selected from B, N, O, S, P (= O), Si and P as aromatic ring skeleton atoms, and the remaining aromatic ring skeleton atoms are carbon. Means an aryl group, 5-6 membered monocyclic heteroaryl, and polycyclic heteroaryl condensed with one or more benzene rings, which may be partially saturated. In addition, heteroaryl in the present invention also includes a form in which one or more heteroaryl is connected by a single bond. Such heteroaryl groups include divalent aryl groups in which heteroatoms in the ring are oxidized or quaternized to form, for example, N-oxides or quaternary salts. Specific examples include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, Monocyclic heteroaryl such as furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, Benzoisoxazolyl, Benzooxazolyl, Isoindoleyl, Indolyl, Indazolyl, Benzothiadiazolyl, Quinolyl, Isoquinolyl, Cinolinyl, Quinazolinyl, Quinoxalinyl, Carbazolyl, Phenantridinyl, Benzo Polycyclic heteroaryls such as dioxolyl, dibenzofuranyl, dibenzothiophenyl and their corresponding N-oxides (e.g. pyridyl N-oxides, quinolyl N-oxides), quaternary salts thereof And the like.
또한, 본 발명에 기재되어 있는 ‘(C1-C30)알킬’기는 바람직하게는 (C1-C20)알킬이고, 더 바람직하게는 (C1-C10)알킬이며, ‘(C6-C30)아릴’기는 바람직하게는 (C6-C20)아릴이다. ‘(C2-C30)헤테로아릴’기는 바람직하게는 (C2-C20)헤테로아릴이다. ‘(C3-C30)시클로알킬’기는 바람직하게는 (C3-C20)시클로알킬이고, 더 바람직하게는 (C3-C7)시클로알킬이다. ‘(C2-C30)알케닐 또는 알키닐’기는 바람직하게는 (C2-C20)알케닐 또는 알키닐이고, 더 바람직하게는 (C2-C10)알케닐 또는 알키닐이다.Further, the '(C1-C30) alkyl' group described in the present invention is preferably (C1-C20) alkyl, more preferably (C1-C10) alkyl, and the '(C6-C30) aryl' group is preferred. Preferably (C6-C20) aryl. The '(C2-C30) heteroaryl' group is preferably (C2-C20) heteroaryl. The '(C3-C30) cycloalkyl' group is preferably (C3-C20) cycloalkyl, more preferably (C3-C7) cycloalkyl. The '(C2-C30) alkenyl or alkynyl' group is preferably (C2-C20) alkenyl or alkynyl, more preferably (C2-C10) alkenyl or alkynyl.
또한 본 발명에 기재되어 있는 “치환 또는 비치환”이라는 기재에서 ‘치환’은 비치환된 치환기에 더 치환되는 경우를 뜻하며, 상기 L1, L2, Ar, R1 내지 R7 및 R11 내지 R17에 더 치환되는 치환기는 각각 중수소, 할로겐, (C1-C30)알킬, 할로겐이 치환된 (C1-C30)알킬, (C6-C30)아릴, (C2-C30)헤테로아릴, (C1-C30)알킬이 치환된 (C2-C30)헤테로아릴, (C6-C30)아릴이 치환된 (C2-C30)헤테로아릴, (C3-C30)시클로알킬, 5원 내지 7원의 헤테로시클로알킬, 트리(C1-C30)알킬실릴, 트리(C6-C30)아릴실릴, 디(C1-C30)알킬(C6-C30)아릴실릴, (C1-C30)알킬디(C6-C30)아릴실릴, (C2-C30)알케닐, (C2-C30)알키닐, 시아노, N-카바졸릴, 디(C1-C30)알킬아미노, 디(C6-C30)아릴아미노, (C1-C30)알킬(C6-C30)아릴아미노, 디(C6-C30)아릴보로닐, 디(C1-C30)알킬보로닐, (C1-C30)알킬(C6-C30)아릴보로닐, (C6-C30)아르(C1-C30)알킬, (C1-C30)알킬(C6-C30)아릴, 카르복실, 니트로 및 히드록시로 이루어진 군으로부터 선택되는 하나 이상인 것을 의미한다.In addition, in the description of "substituted or unsubstituted" described in the present invention, 'substituted' means a case where is further substituted with an unsubstituted substituent, the L 1 , L 2 , Ar, R 1 to R 7 and R 11 to Substituents further substituted for R 17 are deuterium, halogen, (C 1 -C 30) alkyl, halogen substituted (C 1 -C 30) alkyl, (C 6 -C 30) aryl, (C 2 -C 30) heteroaryl, (C 1 -C 30) (C2-C30) heteroaryl substituted with alkyl, (C2-C30) heteroaryl substituted with (C6-C30) aryl, (C3-C30) cycloalkyl, heterocycloalkyl of 5- to 7-membered, tri ( C1-C30) alkylsilyl, tri (C6-C30) arylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, (C1-C30) alkyldi (C6-C30) arylsilyl, (C2-C30 Alkenyl, (C2-C30) alkynyl, cyano, N-carbazolyl, di (C1-C30) alkylamino, di (C6-C30) arylamino, (C1-C30) alkyl (C6-C30) aryl Amino, di (C6-C30) arylboronyl, di (C1-C30) alkylboronyl, (C1-C30) alkyl (C6-C30) arylboronyl, (C6-C30) ar (C1-C30) ) Alkyl, (C1-C30) alkyl (C6) -C30) at least one selected from the group consisting of aryl, carboxyl, nitro and hydroxy.
구체적으로, 상기 L1 및 L2은 각각 독립적으로 단일결합, (C2-C30)헤테로아릴렌 또는 (C6-C30)아릴렌이고; X1 및 X2은 각각 독립적으로 CH 또는 N이며; Y1 및 Y2는 각각 독립적으로 -O-, -S-, -CR5R6- 또는 -NR7-이며, 단, Y2 와 Y3가 동시에 존재하는 경우는 없고; Ar은 각각 독립적으로 수소, 중수소, 할로겐, (C1-C30)알킬, (C6-C30)아릴, (C2-C30)헤테로아릴, 또는 N-카바졸릴이며; R1 내지 R4은 각각 독립적으로 수소, 중수소, 할로겐, (C1-C30)알킬, (C6-C30)아릴, (C2-C30)헤테로아릴, N-카바졸릴 또는 -SiR13R14R15이고; R5 내지 R7는 각각 독립적으로 (C1-C30)알킬, (C6-C30)아릴 또는 (C2-C30)헤테로아릴이거나, 상기 R5와 R6는 융합고리를 포함하거나 포함하지 않는 치환 또는 비치환된 (C3-C30)알킬렌 또는 치환 또는 비치환된 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있으며, 상기 형성된 지환족 고리 및 단일환 또는 다환의 방향족 고리의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 치환될 수 있고; R13 내지 R15는 각각 독립적으로 (C1-C30)알킬, (C6-C30)아릴 또는 (C2-C30)헤테로아릴이고; 상기 L1 및 L2의 아릴렌 및 헤테로아릴렌, Ar의 알킬, 아릴, 헤테로아릴 및 N-카바졸릴, R1 내지 R4의 알킬, 아릴, 헤테로아릴 및 N-카바졸릴, R5 내지 R7 및 R13 내지 R15의 알킬, 아릴 및 헤테로아릴은 각각 중수소, 할로겐, (C1-C30)알킬, 할로겐이 치환된 (C1-C30)알킬, (C6-C30)아릴, (C2-C30)헤테로아릴, (C1-C30)알킬이 치환된 (C2-C30)헤테로아릴, (C6-C30)아릴이 치환된 (C2-C30)헤테로아릴, (C3-C30)시클로알킬, N-카바졸릴, 디(C1-C30)알킬아미노, 디(C6-C30)아릴아미노, (C1-C30)알킬(C6-C30)아릴아미노, (C6-C30)아르(C1-C30)알킬 및 (C1-C30)알킬(C6-C30)아릴로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 더 치환될 수 있다.Specifically, L 1 and L 2 are each independently a single bond, (C2-C30) heteroarylene or (C6-C30) arylene; X 1 and X 2 are Each one independently CH or N; Y 1 and Y 2 are each independently -O-, -S-, -CR 5 R 6 -or -NR 7- , provided that Y 2 and Y 3 are not present at the same time; Ar is each independently hydrogen, deuterium, halogen, (C1-C30) alkyl, (C6-C30) aryl, (C2-C30) heteroaryl, or N-carbazolyl; R 1 to R 4 are each independently hydrogen, deuterium, halogen, (C 1 -C 30) alkyl, (C 6 -C 30) aryl, (C 2 -C 30) heteroaryl, N-carbazolyl or —SiR 13 R 14 R 15 ; R 5 to R 7 are each independently (C 1 -C 30) alkyl, (C 6 -C 30) aryl or (C 2 -C 30) heteroaryl, wherein R 5 and R 6 are substituted or unsubstituted with or without a fused ring. It may be linked to a ring (C3-C30) alkylene or substituted or unsubstituted (C3-C30) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, the alicyclic ring and monocyclic ring formed above Or the carbon atoms of the polycyclic aromatic ring can be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur; R 13 to R 15 are each independently (C 1 -C 30) alkyl, (C 6 -C 30) aryl or (C 2 -C 30) heteroaryl; Wherein L 1 and L 2 of arylene and heteroarylene, of Ar-alkyl, aryl, heteroaryl, and N- carbazolyl, R 1 to R 4 of the alkyl, aryl, heteroaryl and N- carbazolyl, R 5 to R Alkyl, aryl and heteroaryl of 7 and R 13 to R 15 are deuterium, halogen, (C 1 -C 30) alkyl, halogen substituted (C 1 -C 30) alkyl, (C 6 -C 30) aryl, (C 2 -C 30) Heteroaryl, (C2-C30) heteroaryl substituted with (C1-C30) alkyl, (C2-C30) heteroaryl substituted with (C6-C30) aryl, (C3-C30) cycloalkyl, N-carbazolyl, Di (C1-C30) alkylamino, di (C6-C30) arylamino, (C1-C30) alkyl (C6-C30) arylamino, (C6-C30) ar (C1-C30) alkyl and (C1-C30) It may be further substituted with one or more substituents selected from the group consisting of alkyl (C6-C30) aryl.
보다 구체적으로 상기 L1 및 L2은 각각 독립적으로 단일결합, 페닐렌, 비페닐렌, 터페닐렌, 인데닐렌, 플루오레닐렌, 트리페닐레닐렌, 피렌일렌, 페릴렌일렌, 크라이세닐렌, 나프타세닐렌, 플루오란텐일렌, 티오펜일렌, 피롤릴렌, 피라졸릴렌, 티아졸릴렌, 옥사졸릴렌, 옥사디아졸릴렌, 트리아진일렌, 테트라진일렌, 트리아졸릴렌, 퓨라잔일렌, 피리딜렌, 벤조퓨란일렌, 벤조티오펜일렌, 인돌릴렌, 벤조이미다졸릴렌, 벤조티아졸릴렌, 벤조이소티아졸릴렌, 벤조이속사졸릴렌, 벤조옥사졸릴렌, 벤조티아디아졸릴렌, 다이벤조퓨란닐렌 또는 다이벤조싸이오페닐렌이고; Ar은 수소, 메틸, 에틸, n-프로필, i-프로필,n-부틸, i-부틸, t-부틸, n-펜틸, i-펜틸, n-헥실, n-헵틸, n-옥틸, 2-에틸헥실,n-노닐, 데실, 도데실, 헥사데실, 트리플루오르메틸, 퍼플루오르에틸, 트리플루오르에틸, 퍼플루오르프로필, 퍼플루오르부틸, 페닐, 비페닐, 플루오레닐, 플루오란텐일, 터페닐일, 피렌일, 크라이세닐, 나프타세닐, 페릴렌일, 피리딜, 피롤릴, 퓨란일, 티오펜일, 이미다졸릴, 벤조이미다졸릴, 퀴놀릴, 트리아진일, 벤조퓨란일, 다이벤조퓨란일, 벤조티오펜일, 다이벤조티오펜일, 피라졸릴, 인돌릴, 카바졸릴, 티아졸릴, 옥사졸릴, 벤조티아졸릴, 벤조옥사졸릴, 페난트롤린일, 퀴녹살리닐 또는 N-카바졸릴이고; R1 내지 R4는 서로 독립적으로 수소, 중수소, 클로로, 플루오르, 메틸, 에틸, n-프로필, i-프로필, n-부틸, i-부틸, t-부틸, n-펜틸, i-펜틸, n-헥실, n-헵틸,n-옥틸, 2-에틸헥실, n-노닐, 데실, 도데실, 헥사데실, 트리플루오르메틸, 퍼플루오르에틸, 트리플루오르에틸, 퍼플루오르프로필, 퍼플루오르부틸, 페닐, 나프틸, 안트릴, 비페닐, 플루오레닐, 플루오란텐일, 트리페닐렌일, 피렌일, 크라이세닐, 나프타세닐, 페릴렌일, 피리딜, 피롤릴, 퓨란일, 티오펜일, 이미다졸릴, 벤조이미다졸릴, 인데닐, 피라진일, 피리미딘일, 피리다진일, 퀴놀릴, 트리아진일, 벤조퓨란일, 다이벤조퓨란일, 벤조티오펜일, 다이벤조티오펜일, 피라졸릴, 인돌릴, 카바졸릴, 티아졸릴, 옥사졸릴, 벤조티아졸릴, 벤조옥사졸릴, 페난트롤린일, N-카바졸릴, 트리메틸실릴, 트리에틸실릴, 트리프로필실릴, 트리(t-부틸)실릴, t-부틸다이메틸실릴, 다이메틸페닐실릴, 메틸다이페닐실릴 또는 트리페닐실릴이고; 상기 L1, L2, Ar 및 R1 내지 R4의 치환기는 각각 중수소, 클로로, 플루오르, 메틸, 에틸, n-프로필, i-프로필, n-부틸, i-부틸, t-부틸, n-펜틸, i-펜틸,n-헥실, n-헵틸, n-옥틸, 2-에틸헥실, n-노닐, 데실, 도데실, 헥사데실, 트리플루오르메틸, 퍼플루오르에틸, 트리플루오르에틸, 퍼플루오르프로필, 퍼플루오르부틸, 페닐, 나프틸, 비페닐, 9,9-다이메틸플루오레닐, 9,9-다이페닐플루오레닐, 플루오란텐일, 트리페닐렌일, 피렌일, 크라이세닐, 나프타세닐, 페릴렌일, 다이메틸아미노, 다이에틸아미노, 메틸페닐아미노, 다이페닐아미노, 트리메틸실릴, 트리에틸실릴, 트리프로필실릴, 트리(t-부틸)실릴, t-부틸다이메틸실릴, 다이메틸페닐실릴 및 메틸디페닐실릴, 트리페닐실릴, N-카바졸릴 및 N-페닐카바졸릴로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 더 치환될 수 있다.More specifically, L 1 and L 2 are each independently a single bond, phenylene, biphenylene, terphenylene, indenylene, fluorenylene, triphenylenylene, pyrenylene, peryleneylene, chrysenylene, Naphthasenylene, fluoranthhenylene, thiophenylene, pyrroylene, pyrazolylene, thiazolylene, oxazolylene, oxadiazolylene, triazineylene, tetrazinylene, triazolylene, furazanthylene, pyri Dilene, benzofuranylene, benzothiophenylene, indolylene, benzoimidazolylene, benzothiazolylene, benzoisothiazolylene, benzoisoxazolylene, benzoxazolylene, benzothiadiazolylene, dibenzofuran Nylene or dibenzothiophenylene; Ar is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2- Ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, biphenyl, fluorenyl, fluoranthenyl, terphenyl Il, pyrenyl, chrysenyl, naphthacenyl, peryleneyl, pyridyl, pyrrolyl, furanyl, thiophenyl, imidazolyl, benzoimidazolyl, quinolyl, triazinyl, benzofuranyl, dibenzofuranyl , Benzothiophenyl, dibenzothiophenyl, pyrazolyl, indolyl, carbazolyl, thiazolyl, oxazolyl, benzothiazolyl, benzooxazolyl, phenanthrolinyl, quinoxalinyl or N-carbazolyl; R 1 to R 4 independently of one another are hydrogen, deuterium, chloro, fluorine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n Hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, Naphthyl, anthryl, biphenyl, fluorenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, peryleneyl, pyridyl, pyrrolyl, furanyl, thiophenyl, imidazolyl, Benzoimidazolyl, indenyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, triazineyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, pyrazolyl, indolyl , Carbazolyl, thiazolyl, oxazolyl, benzothiazolyl, benzooxazolyl, phenanthrolinyl, N-carbazolyl, trimethylsilyl, triethylsilyl, tripe Peel-silyl, tri (t- butyl) silyl, t- butyl-dimethyl-silyl, dimethylphenyl silyl, methyl diphenyl silyl or triphenyl silyl gt; The substituents of L 1 , L 2 , Ar and R 1 to R 4 are each deuterium, chloro, fluorine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n- Pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl , Perfluorobutyl, phenyl, naphthyl, biphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, Peryleneyl, dimethylamino, diethylamino, methylphenylamino, diphenylamino, trimethylsilyl, triethylsilyl, tripropylsilyl, tri (t-butyl) silyl, t-butyldimethylsilyl, dimethylphenylsilyl and methyldi More than one substituent selected from the group consisting of phenylsilyl, triphenylsilyl, N-carbazolyl and N-phenylcarbazolyl Hwandoel can.
더욱 구체적으로 상기 
[상기 R5, R6 및 R7는 상기 화학식 1에서의 정의와 동일하다.][R 5 , R 6 above And R 7 is the same as defined in Formula 1 above.]
본 발명에 따른 유기 발광 화합물로는 대표적으로 하기의 화합물을 들 수 있다. Examples of the organic light emitting compound according to the present invention include the following compounds.
본 발명에 따른 유기 발광 화합물은 하기 반응식에 나타난 바와 같이 제조될 수 있다.The organic light emitting compound according to the present invention can be prepared as shown in the following scheme.
[반응식 1][Reaction Scheme 1]
[반응식 2]Scheme 2
[상기 반응식 1 및 2에서, L1, L2, Ar, X1, X2, Y1, Y2, R1 내지 R4, a, b, c 및 d는 상기 화학식 1에서의 정의와 동일하고, Hal는 할로겐이다.][In Reaction Schemes 1 and 2, L 1 , L 2 , Ar, X 1 , X 2 , Y 1 , Y 2 , R 1 to R 4 , a, b, c and d are the same as defined in Formula 1 Hal is a halogen.]
또한, 본 발명은 유기 전계 발광 소자를 제공하며, 본 발명에 따른 유기 전계 발광 소자는 제1전극; 제2전극; 및 상기 제1전극 및 제2전극 사이에 개재되는 1층 이상의 유기물층을 갖는 유기 전계 발광 소자에 있어서, 상기 유기물층은 상기 화학식 1의 화합물을 하나 이상 포함한다. 또한 상기 유기물층은 발광층을 포함하고, 이 발광층에서 상기 화학식 1의 화합물을 호스트 물질로 사용할 수 있다. In addition, the present invention provides an organic electroluminescent device, the organic electroluminescent device according to the present invention comprises a first electrode; A second electrode; And at least one organic material layer interposed between the first electrode and the second electrode, wherein the organic material layer includes at least one compound represented by Chemical Formula 1. The organic material layer may include a light emitting layer, and the compound of Formula 1 may be used as a host material in the light emitting layer.
또한 본 발명에 따른 호스트와 함께 사용되는 유기 전계 발광 소자용 인광 도판트에는 대표적으로 하기 화학식 2의 화합물이 있다. In addition, a phosphorescent dopant for an organic electroluminescent device used with a host according to the present invention typically includes a compound represented by the following Chemical Formula 2.
[화학식 2][Formula 2]
MM 1One LL 101101 LL 102102 LL 103103
상기 화학식 2에서,In Formula 2,
여기서 M1은 Ir, Pt, Pd 및 Os으로 이루어진 군으로부터 선택되고,Wherein M 1 is selected from the group consisting of Ir, Pt, Pd and Os,
리간드 L101, L102 및 L103 는 서로 독립적으로 하기 구조로부터 선택되어진다.The ligands L 101 , L 102 and L 103 are independently selected from the following structures.
R201 내지 R203은 서로 독립적으로 수소, 중수소, 할로겐이 치환되거나 치환되지 않은 (C1-C30)알킬, (C1-C30)알킬이 치환되거나 치환되지 않은 (C6-C30)아릴 또는 할로겐이고;R 201 to R 203 independently represent hydrogen, deuterium, (C 1 -C 30) alkyl in which the halogen is optionally substituted (C 1 -C 30) alkyl, (C 6 -C 30) aryl or halogen in which the (C 1 -C 30) alkyl is optionally substituted;
R204 내지 R219는 서로 독립적으로 수소, 중수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C1-C30)알콕시, 치환 또는 비치환된(C3-C30)시클로알킬, 치환 또는 비치환된(C2-C30)알케닐, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된 모노 또는 치환 또는 비치환된 디-(C1-C30)알킬아미노, 치환 또는 비치환된 모노 또는 디-(C6-C30)아릴아미노, SF5, 치환 또는 비치환된 트리(C1-C30)알킬실릴, 치환 또는 비치환된 디(C1-C30)알킬(C6-C30)아릴실릴, 치환 또는 비치환된 트리(C6-C30)아릴실릴, 시아노 또는 할로겐이고;R 204 to R 219 are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C3-C30) cycloalkyl, Substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted mono or substituted or unsubstituted di- (C1-C30) alkylamino, substituted or unsubstituted Substituted mono or di- (C6-C30) arylamino, SF 5 , substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl , Substituted or unsubstituted tri (C6-C30) arylsilyl, cyano or halogen;
R220 내지 R223는 서로 독립적으로 수소, 중수소, 할로겐이 치환되거나 치환되지 않은 (C1-C30)알킬 또는 (C1-C30)알킬이 치환되거나 치환되지 않은 (C6-C30)아릴이고;R 220 to R 223 are each independently hydrogen, deuterium, (C1-C30) alkyl with or without halogen, or (C6-C30) aryl with or without (C1-C30) alkyl;
R224 및 R225는 서로 독립적으로 수소, 중수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 할로겐이거나, R224와 R225는 융합고리를 포함하거나 포함하지 않는 (C3-C12)알킬렌 또는 (C3-C12)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성하며; R 224 and R 225 are independently of each other hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen, or R 224 and R 225 contain fused rings Linked with (C3-C12) alkylene or (C3-C12) alkenylene with or without formation to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;
R226은 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C5-C30)헤테로아릴 또는 할로겐이고;R 226 is substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C5-C30) heteroaryl or halogen;
R227 내지 R229은 서로 독립적으로 수소, 중수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 할로겐이고;R 227 to R 229 are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen;
Q는 
구체적으로 상기 화학식 2의 도판트 화합물로서 다음과 같은 화합물을 사용하는 것이 바람직하다. Specifically, it is preferable to use the following compounds as the dopant compound of Chemical Formula 2.
본 발명의 유기 전계 발광 소자는 화학식 1의 화합물을 포함하고, 이와 동시에 아릴아민계 화합물 또는 스티릴아릴아민계 화합물로 이루어진 군으로부터 선택된 하나 이상의 화합물을 포함할 수 있다. The organic electroluminescent device of the present invention includes a compound of Formula 1, and at the same time may include one or more compounds selected from the group consisting of arylamine-based compounds or styrylarylamine-based compounds.
또한, 본 발명의 유기 전계 발광 소자에 있어서, 유기물층에 상기 화학식 1의 화합물 이외에 1족, 2족, 4주기, 5주기 전이금속, 란탄계열금속 및 d-전이원소의 유기금속으로 이루어진 군으로부터 선택되는 하나 이상의 금속 또는 착체화합물을 더 포함할 수도 있고, 나아가 상기 유기물층은 발광층 및 전하생성층을 더 포함할 수 있다.In addition, in the organic electroluminescent device of the present invention, in addition to the compound of Formula 1, an organic compound selected from the group consisting of Group 1, Group 2, Group 4, Group 5 transition metal, Lanthanide series metal and d- And the organic layer may further include a light emitting layer and a charge generating layer.
또한, 상기 유기물층은 상기 유기 발광 화합물 이외에 청색, 적색 또는 녹색 발광 화합물을 포함하는 유기발광층 하나 이상을 동시에 포함하여 백색 발광을 하는 유기 전계 발광 소자를 형성할 수 있다. In addition, the organic material layer may simultaneously include one or more organic light emitting layers including blue, red, or green light emitting compounds in addition to the organic light emitting compound to form an organic light emitting device that emits white light.
본 발명의 유기 전계 발광 소자에 있어서, 한 쌍의 전극의 적어도 한쪽의 내측표면에, 칼코제나이드(chalcogenide)층, 할로겐화 금속층 및 금속 산화물층으로부터 선택되는 일층(이하, 이들을 “표면층”이라고 지칭함) 이상을 배치하는 것이 바람직하다. 구체적으로는, 발광 매체층 측의 양극 표면에 규소 및 알루미늄의 금속의 칼코제나이드(산화물을 포함한다)층을, 또한 발광매체층 측의 음극 표면에 할로겐화 금속층 또는 금속 산화물층을 배치하는 것이 바람직하다. 이것에 의해 구동의 안정화를 얻을 수 있다. 상기 칼코제나이드의 바람직한 예로는 SiOX(1≤X≤2), AlOX(1≤X≤1.5), SiON 또는 SiAlON 등이 있고, 할로겐화 금속의 바람직한 예로는 LiF, MgF2, CaF2, 불화 희토류 금속 등이 있으며, 금속 산화물의 바람직한 예로는 Cs2O, Li2O, MgO, SrO, BaO, CaO 등이 있다.In the organic electroluminescent device of the present invention, one layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer (hereinafter referred to as " surface layer ") is formed on the inner surface of at least one of the pair of electrodes, Or more. Concretely, it is preferable to dispose a halogenated metal layer or a metal oxide layer on the surface of the anode on the side of the light emitting medium layer and on the surface of the cathode on the side of the light emitting medium layer, with a chalcogenide (including oxide) layer of a metal of silicon and aluminum Do. Thus, stabilization of the drive can be obtained. Preferred examples of the chalcogenide include SiO X (1 ≦ X ≦ 2 ), AlO X (1 ≦ X ≦ 1.5), SiON or SiAlON, and preferred examples of the halogenated metal include LiF, MgF 2 , CaF 2 , and fluoride. Rare earth metals and the like, and preferred examples of the metal oxides include Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, and the like.
또한, 본 발명의 유기 전계 발광 소자에 있어서, 이렇게 제작된 한 쌍의 전극의 적어도 한쪽의 표면에 전자 전달 화합물과 환원성 도판트의 혼합 영역 또는 정공 전달 화합물과 산화성 도판트의 혼합 영역을 배치하는 것도 바람직하다. 이러한 방식에 의해 전자 전달 화합물이 음이온으로 환원되므로 혼합 영역으로부터 발광 매체에 전자를 주입 및 전달하기 용이해진다. 또한, 정공 전달 화합물은 산화되어 양이온으로 되므로 혼합 영역으로부터 발광 매체에 정공을 주입 및 전달하기 용이해진다. 바람직한 산화성 도판트로서는 각종 루이스산 및 억셉터(acceptor) 화합물을 들 수 있고, 바람직한 환원성 도판트로는 알칼리 금속, 알칼리 금속 화합물, 알칼리 토류 금속, 희토류 금속 및 이들의 혼합물을 들 수 있다. 또한 환원성 도판트층을 전하생성층으로 사용하여 두 개 이상의 발광층을 가진 백색 유기 전계 발광소자를 제작할 수 있다.In addition, in the organic electroluminescent device of the present invention, a mixed region of the electron transfer compound and the reducing dopant or a mixed region of the hole transport compound and the oxidative dopant is disposed on at least one surface of the pair of electrodes thus fabricated desirable. In this way, the electron transfer compound is reduced to an anion, thereby facilitating injection and transfer of electrons from the mixed region to the light emitting medium. In addition, since the hole transport compound is oxidized to become a cation, it is easy to inject and transfer holes from the mixed region to the light emitting medium. Preferred oxidative dopants include various Lewis acids and acceptor compounds. Preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. In addition, a white organic electroluminescent device having two or more light emitting layers may be manufactured using a reducing dopant layer as a charge generating layer.
본 발명에 따른 유기 발광 화합물은 발광 효율이 좋고 재료의 수명특성이 뛰어나 소자의 구동수명이 매우 우수한 OLED 소자를 제조할 수 있는 장점이 있다. 또한, 본 발명에 따른 유기 전자재료용 화합물은 전자전달 효율이 높아 소자 제작시 결정화를 방지할 뿐만 아니라 층 형성이 양호하여 소자의 전류특성을 개선시킴으로서 소자의 구동전압을 저하시키고 동시에 전력효율이 향상된 OLED 소자를 제조할 수 있는 장점이 있다.The organic light emitting compound according to the present invention has the advantage of being able to manufacture an OLED device having a good luminous efficiency and excellent life characteristics of the material and excellent driving life of the device. In addition, the compound for an organic electronic material according to the present invention has high electron transfer efficiency, which prevents crystallization during device fabrication and improves current characteristics of the device due to good layer formation, thereby lowering the driving voltage of the device and improving power efficiency. There is an advantage to manufacture an OLED device.
이하에서, 본 발명의 상세한 이해를 위하여 본 발명의 대표 화합물을 들어 본 발명에 따른 유기 발광 화합물, 이의 제조방법 및 소자의 발광특성을 설명한다.Hereinafter, the organic light emitting compound according to the present invention, a method for preparing the same, and light emitting characteristics of the device will be described with reference to a representative compound of the present invention for a detailed understanding of the present invention.
[제조예 1] 화합물 40의 제조Preparation Example 1 Preparation of Compound 40
화합물 compound 1-11-1 의 제조Manufacturing
2-브로모-9,9-다이메틸-9H-플루오렌 (50g, 183.0mmol), 2-클로로아닐린 (38mL, 366.1mmol), Pd(OAc)2 (1.2g, 5.5mmol), P(t-Bu)3 (8.8mL, 18.3mmol), NaOt-Bu (35g, 366.1mmol) 및 톨루엔 (180mL)을 혼합하고 2.5시간동안 환류 교반시켰다. 반응이 종료되면 반응액을 여과하고 여과한 케이크(cake)는 다시 다이클로로메탄으로 세척하였다. 유기층을 정제수로 세척하고 MgSO4로 건조하고 감압 농축 후 조 오일(crude oil)을 실리카 겔 여과하고 여액을 감압 농축하여 화합물 1-1 (47g, 80%)를 얻었다.2-bromo-9,9-dimethyl-9H-fluorene (50 g, 183.0 mmol), 2-chloroaniline (38 mL, 366.1 mmol), Pd (OAc) 2 (1.2 g, 5.5 mmol), P (t -Bu) 3 (8.8 mL, 18.3 mmol), NaOt-Bu (35 g, 366.1 mmol) and toluene (180 mL) were mixed and stirred at reflux for 2.5 h. After the reaction was completed, the reaction solution was filtered and the filtered cake was washed again with dichloromethane. The organic layer was washed with purified water, dried over MgSO 4 , concentrated under reduced pressure, crude oil was filtered through silica gel, and the filtrate was concentrated under reduced pressure to obtain Compound 1-1 (47 g, 80%).
화합물 compound 1-21-2 의 제조Manufacturing
화합물 1-1 (46g, 143.8mmol), Pd(OAc)2 (968mg, 4.3mmol), 다이-t-부틸(메틸)포스포늄테트라플루오로보레이트 (2g, 4.31mmol) 및 DMAc (200mL)을 혼합하고 21시간동안 환류 교반시켰다. 반응이 종료되면 반응액을 여과하고 여과한 케이크(cake)는 다시 다이클로로메탄으로 세척하였다. 유기층을 정제수로 세척하고 MgSO4로 건조하고 감압 농축 후 조 오일(crude oil)을 실리카 겔 여과하고 여액을 감압 농축하여 화합물 1-2 (17g, 53%)를 얻었다.Mix compound 1-1 (46 g, 143.8 mmol), Pd (OAc) 2 (968 mg, 4.3 mmol), di-t-butyl (methyl) phosphoniumtetrafluoroborate (2 g, 4.31 mmol) and DMAc (200 mL) And refluxed for 21 hours. After the reaction was completed, the reaction solution was filtered and the filtered cake was washed again with dichloromethane. The organic layer was washed with purified water, dried over MgSO 4 , concentrated under reduced pressure, crude oil was filtered through silica gel, and the filtrate was concentrated under reduced pressure to obtain Compound 1-2 (17 g, 53%).
화합물 compound 1-31-3 의 제조Manufacturing
3-(9H-카바졸-9-일)페닐보론산 (7g, 24.4mmol), 2,4-다이클로로피리미딘 (3.9g, 26.9mmol), Pd(PPh3)4 (845mg, 0.7mmol), K2CO3 (6.7g, 48.8mmol), Toluene(100mL), EtOH(25mL) 및 정제수(25mL)를 혼합하고 5시간동안 환류 교반시켰다. 반응이 종료되면 상온으로 냉각시킨 다음 여과하고, 유기층을 MgSO4로 건조하고 감압 농축 후 실리카 겔 여과하고 여액을 감압 농축하여 화합물 1-3 (6g, 70%)를 얻었다.3- (9H-carbazol-9-yl) phenylboronic acid (7g, 24.4mmol), 2,4-dichloropyrimidine (3.9g, 26.9mmol), Pd (PPh 3 ) 4 (845mg, 0.7mmol) , K 2 CO 3 (6.7 g, 48.8 mmol), Toluene (100 mL), EtOH (25 mL) and purified water (25 mL) were mixed and stirred at reflux for 5 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered, and the organic layer was dried over MgSO 4 , concentrated under reduced pressure, filtered through silica gel, and the filtrate was concentrated under reduced pressure to obtain Compound 1-3 (6g, 70%).
화합물 compound 4040 의 제조Manufacturing
화합물 1-2 (6.6g, 18.6mmol)을 넣고 DMF(120mL)를 넣어 녹인 후 0℃에서 NaH (813mg, 20.3mmol)를 넣고 10분간 교반시켰다. 여기에 화합물 1-3 (4.8g, 16.9mmol)를 첨가하고 19시간동안 교반시켰다. 반응이 종료되면 상기 반응혼합물에 MeOH를 가하여 형성된 고체를 실리카 겔 여과하고 DMF로 재결정하여 화합물 40 (4g, 36%)를 얻었다.Compound 1-2 (6.6g, 18.6mmol) was added, dissolved in DMF (120mL), NaH (813mg, 20.3mmol) was added at 0 ° C, and stirred for 10 minutes. To this compound 1-3 (4.8 g, 16.9 mmol) was added and stirred for 19 h. After the reaction was completed, MeOH was added to the reaction mixture, and the solid formed by silica gel filtration and recrystallized with DMF to obtain compound 40 (4 g, 36%).
MS/FAB found 603, calculated 602.73MS / FAB found 603, calculated 602.73
[제조예 2] 화합물 94의 제조Preparation Example 2 Preparation of Compound 94
화합물 compound 2-12-1 의 제조Manufacturing
1-브로모-2-나이트로벤젠 (85g, 0.42mol), 다이벤조[b,d]티오펜-4-일보론산 (80g, 0.35mol), Pd(PPh3)4 (20g, 0.018mol), K2CO3 (116g, 1.0mol), 톨루엔(1700ml), EtOH (440ml) 및 증류수(440ml)을 혼합한 후 120℃에서 12시간 교반시켰다. 반응 종결 후 EA로 유기층을 추출하고 MgSO4로 건조하고, 거른 후 감압 증류하여 용매를 제거한 후 컬럼 분리하여 화합물 2-1 (93g, 87%)을 얻었다.1-bromo-2-nitrobenzene (85g, 0.42mol), dibenzo [b, d] thiophen-4-ylboronic acid (80g, 0.35mol), Pd (PPh 3 ) 4 (20g, 0.018mol) , K 2 CO 3 (116g, 1.0mol), toluene (1700ml), EtOH (440ml) and distilled water (440ml) were mixed and stirred at 120 ° C for 12 hours. After completion of the reaction, the organic layer was extracted with EA, dried over MgSO 4 , filtered, distilled under reduced pressure to remove the solvent, and column separated to obtain a compound 2-1 (93g, 87%).
화합물 compound 2-22-2 의 제조Manufacturing
화합물 2-1 (88g, 0.29mol), P(OEt)3 (960ml, 0.4M), 트리에틸포스파이트 (960ml)을 혼합하고, 90℃에서 12시간 교반시켰다. 반응 종결 후 증류(distill.)로 트리에틸포스파이트를 제거하고, 컬럼 분리하여 화합물 2-2 (40g, 70%)을 얻었다.Compound 2-1 (88 g, 0.29 mol), P (OEt) 3 (960 ml, 0.4M) and triethylphosphite (960 ml) were mixed and stirred at 90 ° C. for 12 hours. After completion of the reaction, triethyl phosphite was removed by distillation, and the mixture was separated by column to obtain compound 2-2 (40 g, 70%).
화합물 compound 9494 의 제조Manufacturing
NaH 60% (0.9g, 0.02mol)을 DMF (50ml)에 녹여 교반시켰다. 화합물 2-2 (4.69g, 0.017mol)을 DMF (20ml)에 녹인 후, 상기 NaH 용액에 첨가하여 1시간 동안 교반시켰다. 화합물 1-3 (6.1g, 0.017mol)을 DMF (100ml)에 녹인 후 교반시키고, 여기에 상기 화합물 2-2의 혼합용액을 첨가하고 12시간 교반시켰다. 반응이 끝나면 생성된 노란색 고체를 거른 후, 재결정하여 화합물 94 (3g, 30%)을 얻었다. NaH 60% (0.9g, 0.02mol) was dissolved in DMF (50ml) and stirred. Compound 2-2 (4.69 g, 0.017 mol) was dissolved in DMF (20 ml) and then added to the NaH solution and stirred for 1 hour. Compound 1-3 (6.1g, 0.017mol) was dissolved in DMF (100ml) and stirred, and a mixed solution of compound 2-2 was added thereto and stirred for 12 hours. After the reaction, the resulting yellow solid was filtered and recrystallized to obtain compound 94 (3 g, 30%).
MS/FAB found 593, calculated 592.71MS / FAB found 593, calculated 592.71
[제조예 3] 화합물 105의 제조Preparation Example 3 Preparation of Compound 105
화합물 compound 3-13-1 의 제조Manufacturing
카바졸 (26g, 155.49mmol), 4-브로모아이오도벤젠 (87g, 310.9mmol), CuI (14.8g, 77.74mmol), 에틸렌다이아민 (9.3g, 155.49mmol), K3PO4 (99g, 466.47mmol) 및 톨루엔 (1000mL)을 혼합하고 환류교반시켰다. 15시간 후 상온으로 냉각하고 CuI와 K3PO4를 감압 여과하여 제거시켰다. 여액을 MC로 추출하고 증류수로 씻어준 다음, 컬럼 분리하여 화합물 3-1 (35g, 70%)을 얻었다. Carbazole (26g, 155.49mmol), 4-bromoiodobenzene (87g, 310.9mmol), CuI (14.8g, 77.74mmol), ethylenediamine (9.3g, 155.49mmol), K 3 PO 4 (99g, 466.47 mmol) and toluene (1000 mL) were mixed and stirred under reflux. After 15 hours, the mixture was cooled to room temperature, and CuI and K 3 PO 4 were removed by filtration under reduced pressure. The filtrate was extracted with MC and washed with distilled water, and then separated by column to obtain compound 3-1 (35g, 70%).
화합물 compound 3-23-2 의 제조Manufacturing
화합물 3-1 (35g, 108.6mmol)을 THF (600mL)에 녹인 후 -78℃에서 n-BuLi (52ml, 130.35mmol, 2.5M in hexane)을 천천히 첨가시킨 후 한 시간 동안 교반시켰다. 상기 반응물에 B(Oi-Pr)3 (37ml, 162.9mmol)을 천천히 첨가하고, 온도를 천천히 올리면서 상온에서 12시간 교반시켰다. EA로 유기층을 추출하고 무수 MgSO4를 이용하여 잔여 수분을 제거한 뒤 감압 증류하여 용매를 제거한 후 EA와 Hexane으로 재결정하여 화합물 3-2 (25g, 81%)을 얻었다. Compound 3-1 (35g, 108.6mmol) was dissolved in THF (600mL) and n-BuLi (52ml, 130.35mmol, 2.5M in hexane) was slowly added at -78 ° C and stirred for an hour. B (Oi-Pr) 3 (37 ml, 162.9 mmol) was slowly added to the reaction, and the mixture was stirred at room temperature for 12 hours while slowly raising the temperature. The organic layer was extracted with EA, residual water was removed using anhydrous MgSO 4 , distillation under reduced pressure was carried out to remove the solvent, and recrystallized with EA and Hexane to obtain compound 3-2 (25g, 81%).
화합물 compound 3-33-3 의 제조Manufacturing
화합물 3-2 (10g, 34.82mmol), 2,4-다이클로로피리미딘 (7.7g, 52.24mmol), Pd(PPh3)4 (1.6g, 1.39mmol), 2M Na2CO3 (45ml), 톨루엔 (150ml) 및 에탄올 (45ml)를 혼합하고 환류교반시켰다. 12시간 후 상온으로 냉각하고 증류수를 가한 후 EA로 유기층을 추출하고 무수 MgSO4를 이용하여 잔여 수분을 제거한 뒤 감압 증류하여 용매를 제거한 후 컬럼 분리하여 화합물 3-3 (11g, 89%)을 얻었다. Compound 3-2 (10 g, 34.82 mmol), 2,4-dichloropyrimidine (7.7 g, 52.24 mmol), Pd (PPh 3 ) 4 (1.6 g, 1.39 mmol), 2M Na 2 CO 3 (45 ml), Toluene (150 ml) and ethanol (45 ml) were mixed and refluxed. After 12 hours, the mixture was cooled to room temperature, distilled water was added, the organic layer was extracted with EA, residual water was removed using anhydrous MgSO 4 , and the solvent was distilled off under reduced pressure to obtain a compound 3-3 (11 g, 89%) by column separation. .
화합물 compound 105105 의 제조Manufacturing
화합물 2-2 (5g, 18.29mmol), 화합물 3-3 (7.8g, 21.94mmol)을 DMF (150ml)에 녹이고 NaH (1.09g, 27.43mmol, 60% in mineral oil)을 천천히 가하였다. 상온에서 12시간 교반시킨 다음, 메탄올을 가하여 생성된 고체를 감압 여과하고, 얻어진 고체를 EA와 DMF로 재결정하여 화합물 105 (6.5g, 60%)을 얻었다. Compound 2-2 (5g, 18.29mmol), Compound 3-3 (7.8g, 21.94mmol) was dissolved in DMF (150ml) and NaH (1.09g, 27.43mmol, 60% in mineral oil) was added slowly. After stirring for 12 hours at room temperature, methanol was added, and the resulting solid was filtered under reduced pressure, and the obtained solid was recrystallized from EA and DMF to obtain Compound 105 (6.5 g, 60%).
MS/FAB found 593, calculated 592.71MS / FAB found 593, calculated 592.71
[제조예 4] 화합물 111의 제조Preparation Example 4 Preparation of Compound 111
화합물 compound 4-14-1 의 제조Manufacturing
1-브로모-2-나이트로벤젠 (44g, 0.21mol), 다이벤조[b,d]퓨란-4-일보론산 (40g, 0.18mol), Pd(PPh3)4 (10.3g, 0.008mol), K2CO3 (72g, 0.53mol), 톨루엔(880ml), EtOH (300ml)및 증류수 (300ml)을 혼합한 후 120℃에서 12시간 교반시켰다. 반응 종결 후 EA로 유기층을 추출하고 MgSO4로 건조하고, 거른 후 감압 증류하여 용매를 제거한 후 컬럼 분리하여 화합물 4-1 (43g, 85%) 을 얻었다.1-bromo-2-nitrobenzene (44 g, 0.21 mol), dibenzo [b, d] furan-4-ylboronic acid (40 g, 0.18 mol), Pd (PPh 3 ) 4 (10.3 g, 0.008 mol) , K 2 CO 3 (72 g, 0.53 mol), toluene (880 ml), EtOH (300 ml) and distilled water (300 ml) were mixed and stirred at 120 ° C. for 12 hours. After completion of the reaction, the organic layer was extracted with EA, dried over MgSO 4 , filtered, distilled under reduced pressure to remove the solvent, and column separated to obtain compound 4-1 (43g, 85%).
화합물 compound 4-24-2 의 제조Manufacturing
화합물 4-1 (43g, 0.15mol), P(OEt)3 (400ml, 0.4M) 및 트리에틸포스파이트 (400ml)을 혼합하고, 90℃에서 12시간 교반시켰다. 반응 종결 후 증류(distill.)로 트리에틸포스파이트를 제거하고, 컬럼 분리하여 화합물 4-2 (30g, 78%) 을 얻었다.Compound 4-1 (43g, 0.15mol), P (OEt) 3 (400ml, 0.4M) and triethylphosphite (400ml) were mixed and stirred at 90 ° C for 12 hours. After completion of the reaction, triethyl phosphite was removed by distillation, and the mixture was separated by column to obtain compound 4-2 (30 g, 78%).
화합물 compound 111111 의 제조Manufacturing
NaH 60% (0.88g, 0.022mol)을 DMF (100ml)에 녹여 교반시켰다. 화합물 4-2 (4.34g, 0.016mol)을 DMF (50ml)에 녹인 후, 상기 NaH 용액에 첨가하여 1시간 동안 교반시켰다. 화합물 1-3 (6g, 0.16mol)을 DMF (50ml)에 녹인 후 교반시키고, 여기에 상기 화합물 4-2의 혼합용액을 첨가하고 12시간 교반시켰다. 반응이 끝나면 생성된 노란색 고체를 거른 후, 재결정하여 화합물 111 (1.6g, 18%)을 얻었다. NaH 60% (0.88 g, 0.022 mol) was dissolved in DMF (100 ml) and stirred. Compound 4-2 (4.34 g, 0.016 mol) was dissolved in DMF (50 ml), and then added to the NaH solution, followed by stirring for 1 hour. Compound 1-3 (6g, 0.16mol) was dissolved in DMF (50ml) and stirred, and a mixed solution of compound 4-2 was added thereto and stirred for 12 hours. After the reaction, the resulting yellow solid was filtered and recrystallized to obtain Compound 111 (1.6g, 18%).
MS/FAB found 577, calculated 576.64MS / FAB found 577, calculated 576.64
[제조예 5] 화합물 116의 제조Preparation Example 5 Preparation of Compound 116
화합물 compound 5-15-1 의 제조Manufacturing
다이벤조[b,d]티오펜-4-일보론산 (41g, 181mmol), 1,3-다이브로모나이트로벤젠 (71g, 254.5mmol), 2M Na2CO3 수용액 (270ml), 톨루엔 (900ml) 및 에탄올 (300ml)를 혼합한 후 환류 교반시켰다. 5시간 후 상온으로 냉각하고 증류수를 가한 후 EA로 유기층을 추출하고 무수 MgSO4를 이용하여 잔여 수분을 제거한 뒤 감압 증류하여 용매를 제거한 후 컬럼 분리하여 화합물 5-1 (34g, 35%)을 얻었다. Dibenzo [b, d] thiophen-4-ylboronic acid (41g, 181mmol), 1,3-dibromonitetrobenzene (71g, 254.5mmol), 2M Na 2 CO 3 aqueous solution (270ml), toluene (900ml) And ethanol (300 ml) were mixed and then stirred at reflux. After 5 hours, the mixture was cooled to room temperature, distilled water was added, the organic layer was extracted with EA, residual water was removed using anhydrous MgSO 4 , distillation under reduced pressure to remove the solvent, and column separation was performed to obtain compound 5-1 (34g, 35%). .
화합물 compound 5-25-2 의 제조Manufacturing
화합물 5-1 (34g, 89.52mmol), 트리에틸포스파이트 (350ml) 및 1,2-다이클로로벤젠 (350ml)를 혼합하고 150℃에서 12시간 교반시켰다. 반응 종결 후 상온으로 냉각하고 감압 증류하여 용매를 제거한 후 EA로 재결정하여 화합물 5-2 (11g, 35%)을 얻었다. Compound 5-1 (34 g, 89.52 mmol), triethyl phosphite (350 ml) and 1,2-dichlorobenzene (350 ml) were mixed and stirred at 150 ° C for 12 h. After completion of the reaction, the mixture was cooled to room temperature, distilled under reduced pressure to remove the solvent, and then recrystallized with EA to obtain Compound 5-2 (11 g, 35%).
화합물 compound 5-35-3 의 제조Manufacturing
화합물 5-2 (7g, 25.60mmol), 아이오도벤젠 (10.44g, 51.21mmol), CuI (2.5g, 12.80mmol), K3PO4 16.30g(76.82mmol) 및 톨루엔 (200ml)을 혼합하고 50℃로 가열시킨 후 에틸렌다이아민 (1.72ml, 25.60mmol)을 첨가시키고, 12시간 환류 교반시켰다. 상온으로 냉각하고 EA로 추출하고 NaHCO3 수용액으로 씻어준 다음, MgSO4로 건조하고, 거른 후 감압 증류하여 용매를 제거한 후 컬럼 분리하여 화합물 5-3 (8g, 89%)을 얻었다. Compound 5-2 (7 g, 25.60 mmol), iodobenzene (10.44 g, 51.21 mmol), CuI (2.5 g, 12.80 mmol), K 3 PO 4 16.30 g (76.82 mmol) and toluene (200 ml) were mixed and 50 After heating to C, ethylenediamine (1.72ml, 25.60mmol) was added and stirred at reflux for 12 hours. Cool to room temperature, extract with EA, NaHCO 3 The mixture was washed with an aqueous solution, dried over MgSO 4 , filtered, and distilled under reduced pressure to remove the solvent, followed by column separation to obtain compound 5-3 (8g, 89%).
화합물 compound 116116 의 제조Manufacturing
NaH (216mg)을 DMF (30ml)에 녹여 교반시켰다. 화합물 5-3 (3.5g, 10.015mmol)을 DMF (20ml)에 녹인 후, 상기 NaH 용액에 첨가하여 1시간 동안 교반시켰다. 화합물 1-3 (4.3g, 12.0189mmol)을 DMF (20ml)에 녹인 후 교반시키고, 여기에 상기 화합물 5-3의 혼합용액을 첨가하고 12시간 교반시켰다. 반응이 끝나면 생성된 노란색 고체를 거른 후, 컬럼 분리하여 화합물 116 (12g, 60%)을 얻었다. NaH (216 mg) was dissolved in DMF (30 ml) and stirred. Compound 5-3 (3.5 g, 10.015 mmol) was dissolved in DMF (20 ml) and then added to the NaH solution and stirred for 1 hour. Compound 1-3 (4.3 g, 12.0189 mmol) was dissolved in DMF (20 ml) and stirred, and a mixed solution of compound 5-3 was added thereto and stirred for 12 hours. After the reaction, the resulting yellow solid was filtered and separated by column to obtain compound 116 (12 g, 60%).
MS/FAB found 669, calculated 668.81MS / FAB found 669, calculated 668.81
[제조예 6] 화합물 118의 제조Preparation Example 6 Preparation of Compound 118
화합물 compound 6-16-1 의 제조Manufacturing
2,5-다이브로모나이트로벤젠 (30g, 106.8mmol), 다이 벤조티오펜-4-일보론산 (20.3g, 88.9mmol), Pd(PPh3)4 (5.1g, 4.45mmol), Na2CO3 (27.9g, 267mmol), 톨루엔 (600mL) 및 EtOH (100ml)를 혼합하고 90℃에서 3시간동안 교반시켰다. 교반이 완료된 후 증류수를 가한 후 EA로 유기층을 추출하고 무수 MgSO4를 이용하여 잔여 수분을 제거한 뒤 감압 증류하여 용매를 제거한 후 컬럼 분리하여 화합물 6-1 24g (59%)을 얻었다.2,5-Dibromonionibenzene (30g, 106.8mmol), Dibenzothiophen-4-ylboronic acid (20.3g, 88.9mmol), Pd (PPh 3 ) 4 (5.1g, 4.45mmol), Na 2 CO 3 (27.9 g, 267 mmol), toluene (600 mL) and EtOH (100 mL) were mixed and stirred at 90 ° C. for 3 hours. After stirring was completed, distilled water was added, the organic layer was extracted with EA, residual water was removed using anhydrous MgSO 4 , and the solvent was distilled off under reduced pressure to obtain a compound 6-1 24g (59%).
화합물 compound 6-26-2 의 제조Manufacturing
화합물 6-1 (23g, 59.85mmol), 페닐보론산 (8.8g, 71.83mmol), Pd(PPh3)4 (3.46g, 2.99mmol), Na2CO3 (19g, 179.5mmol), 톨루엔 (180mL) 및 EtOH (90ml)를 혼합하고 120℃에서 3시간동안 교반시켰다. 교반이 완료된 후 증류수를 가한 후 EA로 유기층을 추출하고 무수 MgSO4를 이용하여 잔여 수분을 제거한 뒤 감압 증류하여 용매를 제거한 후 컬럼 분리하여 화합물 6-2 22g (96%)을 얻었다.Compound 6-1 (23g, 59.85mmol), Phenylboronic Acid (8.8g, 71.83mmol), Pd (PPh 3 ) 4 (3.46g, 2.99mmol), Na 2 CO 3 (19g, 179.5mmol), Toluene (180mL ) And EtOH (90 ml) were mixed and stirred at 120 ° C. for 3 hours. After stirring was completed, distilled water was added, the organic layer was extracted with EA, residual water was removed using anhydrous MgSO 4 , distillation under reduced pressure was carried out to remove the solvent, and column separation was performed to obtain compound 6-2 22g (96%).
화합물 compound 6-36-3 의 제조Manufacturing
화합물 6-2 (15g, 39.3mmol)을 넣고 트리에틸포스파이트 (150ml)를 혼합하고 150℃에서 24시간 교반시켰다. 교반이 완료된 후 남은 용매를 증류장치로 제거하고 컬럼 분리하여 화합물 6-3 6g (46%)을 얻었다.Compound 6-2 (15 g, 39.3 mmol) was added and triethyl phosphite (150 ml) was mixed and stirred at 150 ° C for 24 hours. After stirring was complete, the remaining solvent was removed by a distillation apparatus and column separated to obtain 6g (46%) of compound 6-3 .
화합물 compound 118118 의 제조Manufacturing
NaH (600mg, 18.1mmol)을 DMF (30mL)에 녹여 교반시켰다. 화합물 6-3 (5g, 14.3mmol)을 DMF (30mL)에 녹인 후, 상기 NaH 용액에 첨가하여 1시간 동안 교반시켰다. 화합물 1-3 (4.3g, 11.9mmol)을 DMF (30mL)에 녹인 후 교반시키고, 여기에 상기 화합물 6-3의 혼합용액을 첨가하고 실온에서 24시간 교반시켰다. 반응이 끝나면 생성된 고체를 거른 후, EA로 씻어주고 컬럼 분리하여 화합물 118 (1.8g, 23%)를 얻었다.NaH (600 mg, 18.1 mmol) was dissolved in DMF (30 mL) and stirred. Compound 6-3 (5 g, 14.3 mmol) was dissolved in DMF (30 mL), and then added to the NaH solution, followed by stirring for 1 hour. Compound 1-3 (4.3 g, 11.9 mmol) was dissolved in DMF (30 mL) and stirred, and a mixed solution of compound 6-3 was added thereto and stirred at room temperature for 24 hours. After the reaction, the resulting solid was filtered, washed with EA and separated by column to obtain compound 118 (1.8 g, 23%).
MS/FAB found 669, calculated 668.81
MS / FAB found 669, calculated 668.81
[실시예 1] 본 발명에 따른 유기 발광 화합물을 이용한 OLED 소자 제작Example 1 Fabrication of an OLED Device Using an Organic Light Emitting Compound According to the Present Invention
본 발명의 발광 재료를 이용한 구조의 OLED 소자를 제작하였다. 우선, OLED용 글래스(삼성-코닝사 제조)로부터 얻어진 투명전극 ITO 박막(15Ω/□)을, 트리클로로에틸렌, 아세톤, 에탄올, 증류수를 순차적으로 사용하여 초음파 세척을 실시한 후, 이소프로판올에 넣어 보관한 후 사용하였다. 다음으로 진공 증착 장비의 기판 홀더에 ITO기판을 장착한 후, 진공 증착장비 내의 셀에 N1,N1'-([1,1'-바이페닐]-4,4'-다이일)비스(N1-(나프탈렌-1-일)-N4,N4-다이페닐벤젠-1,4-다이아민) (N1,N1'-([1,1'-biphenyl]-4,4'-diyl)bis(N1-(naphthalen-1-yl)-N4,N4- diphenylbenzene-1,4-diamine))을 넣고 챔버 내의 진공도가 10-6 torr에 도달할 때까지 배기시킨 후, 셀에 전류를 인가하여 증발시켜 ITO 기판 위에 60nm 두께의 정공주입층을 증착하였다. 이어서, 진공 증착 장비 내의 다른 셀에 N,N'-다이(4-바이페닐)-N,N'-다이(4-바이페닐)-4,4'-다이아미노바이페닐 (N,N'-di(4-biphenyl)-N,N'-di(4-biphenyl)-4,4'-diaminobiphenyl)을 넣고, 셀에 전류를 인가하여 증발시켜 정공주입층 위에 20nm 두께의 정공전달층을 증착하였다. 정공주입층, 정공전달층을 형성시킨 후, 그 위에 발광층을 다음과 같이 증착시켰다. 진공 증착 장비 내의 한쪽 셀에 호스트로서 본 발명의 화합물 40를 넣고, 또 다른 셀에는 도판트로서 화합물 D-5을 각각 넣은 후, 두 물질을 다른 속도로 증발시켜 15중량%으로 도핑함으로서 상기 정공전달층위에 30nm 두께의 발광층을 증착하였다. 이어서 상기 발광층 위에 전자 전달층으로써 한쪽 셀에 이어서 상기 발광층 위에 전자 전달층으로써 한쪽 셀에 2-(4-(9,10-다이(나프탈렌-2-일)안트라센-2-일)페닐)-1-페닐-1H-벤조[d]이미다졸 (2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole)을 넣고, 또 다른 셀에는 리튬 퀴놀레이트(Lithium quinolate)를 각각 넣은 후, 두 물질을 같은 속도로 증발시켜 50중량%으로 도핑 함으로서 30nm의 전자 전달층을 증착하였다. 이어서 전자 주입층으로 리튬 퀴놀레이트(Lithium quinolate)를 2nm 두께로 증착한 후, 다른 진공 증착장비를 이용하여 Al 음극을 150nm의 두께로 증착하여 OLED 소자를 제작하였다. 재료 별로 각 화합물은 10-6 torr 하에서 진공 승화 정제하여 사용하였다.An OLED device having a structure using the light emitting material of the present invention was produced. First, a transparent electrode ITO thin film (15? /?) Obtained from a glass for OLED (manufactured by Samsung Corning) was ultrasonically cleaned using trichlorethylene, acetone, ethanol and distilled water sequentially and stored in isopropanol Respectively. Next, the ITO substrate is mounted on the substrate holder of the vacuum deposition apparatus, and then N 1 , N 1 ′ -([1,1′-biphenyl] -4,4′-diyl) bis ( N 1-(naphthalen- 1 -yl) -N 4 , N 4 -diphenylbenzene-1,4-diamine) (N 1 , N 1 ' -([1,1'-biphenyl] -4,4' -diyl) bis (N 1- (naphthalen-1-yl) -N 4 , N 4 -diphenylbenzene-1,4-diamine)) and evacuated until the vacuum in the chamber reaches 10 -6 torr. A current was applied to the cell and evaporated to deposit a 60 nm thick hole injection layer on the ITO substrate. Subsequently, N, N'-di (4-biphenyl) -N, N'-di (4-biphenyl) -4,4'-diaminobiphenyl (N, N'-) was added to another cell in the vacuum deposition equipment. Di (4-biphenyl) -N, N'-di (4-biphenyl) -4,4'-diaminobiphenyl) was added, and a 20 nm-thick hole transport layer was deposited on the hole injection layer by evaporation by applying a current to the cell. . After the hole injection layer and the hole transport layer were formed, the light emitting layer was deposited thereon as follows. Compound 40 of the present invention as a host in one cell in a vacuum deposition equipment, Compound D-5 as a dopant in each cell, and then the two materials were evaporated at different rates to be doped at 15% by weight to transfer the holes. A light emitting layer having a thickness of 30 nm was deposited on the layer. Subsequently, one cell as the electron transporting layer on the light emitting layer, followed by 2- (4- (9,10-di (naphthalen-2-yl) anthracen-2-yl) phenyl) -1 in one cell as the electron transporting layer on the light emitting layer -Phenyl-1H-benzo [d] imidazole (2- (4- (9,10-di (naphthalen-2-yl) anthracen-2-yl) phenyl) -1-phenyl-1H-benzo [d] imidazole Lithium quinolate was added to each other cell, and the electron transport layer of 30 nm was deposited by doping at 50 wt% by evaporating both materials at the same rate. Subsequently, Lithium quinolate was deposited to a thickness of 2 nm as an electron injection layer, and an Al cathode was deposited to a thickness of 150 nm using another vacuum deposition equipment to manufacture an OLED device. Each compound was used by vacuum sublimation purification under 10 -6 torr.
그 결과, 3.9 V의 전압에서 2.33 mA/cm2의 전류가 흘렀으며, 1110 cd/m2의 녹색발광이 확인되었다. As a result, a current of 2.33 mA / cm 2 flowed at a voltage of 3.9 V, and green light emission of 1110 cd / m 2 was confirmed.
[실시예 2] 본 발명에 따른 유기 발광 화합물을 이용한 OLED 소자 제작Example 2 Fabrication of an OLED Device Using an Organic Light Emitting Compound According to the Present Invention
발광재료로서 호스트에는 화합물 94, 도판트에는 화합물 D-5을 사용한 것 외에는 실시예1과 동일한 방법으로 OLED소자를 제작하였다.An OLED device was manufactured in the same manner as in Example 1, except that Compound 94 was used as a light emitting material and Compound D-5 was used as a dopant.
그 결과, 3.9 V의 전압에서 2.08 mA/cm2의 전류가 흘렀으며, 1110 cd/m2의 녹색발광이 확인되었다.As a result, a current of 2.08 mA / cm 2 flowed at a voltage of 3.9 V, and green light emission of 1110 cd / m 2 was confirmed.
[실시예 3] 본 발명에 따른 유기 발광 화합물을 이용한 OLED 소자 제작Example 3 Fabrication of OLED Device Using Organic Light Emitting Compound According to the Present Invention
발광재료로서 호스트에는 화합물 105, 도판트에는 화합물 D-34을 사용한 것 외에는 실시예1과 동일한 방법으로 OLED소자를 제작하였다.An OLED device was manufactured in the same manner as in Example 1, except that Compound 105 was used as a light emitting material and Compound D-34 was used as a dopant.
그 결과, 4.0 V의 전압에서 2.53 mA/cm2의 전류가 흘렀으며, 1170 cd/m2의 녹색발광이 확인되었다.As a result, a current of 2.53 mA / cm 2 flowed at a voltage of 4.0 V, and green light emission of 1170 cd / m 2 was confirmed.
[실시예 4] 본 발명에 따른 유기발광화합물을 이용한 OLED 소자 제작Example 4 Fabrication of OLED Device Using Organic Light Emitting Compound According to the Present Invention
발광재료로서 호스트에는 화합물 111, 도판트에는 화합물 D-5을 사용한 것 외에는 실시예1과 동일한 방법으로 OLED소자를 제작하였다.An OLED device was manufactured in the same manner as in Example 1, except that Compound 111 was used as a light emitting material and Compound D-5 was used as a dopant.
그 결과, 4.2 V의 전압에서 2.12 mA/cm2의 전류가 흘렀으며, 1150 cd/m2의 녹색발광이 확인되었다.As a result, a current of 2.12 mA / cm 2 flowed at a voltage of 4.2 V, and green light emission of 1150 cd / m 2 was confirmed.
[실시예 5] 본 발명에 따른 유기발광화합물을 이용한 OLED 소자 제작Example 5 Fabrication of OLED Device Using Organic Light Emitting Compound According to the Present Invention
발광재료로서 호스트에는 화합물 118, 도판트에는 화합물 D-5을 사용한 것 외에는 실시예1과 동일한 방법으로 OLED소자를 제작하였다.An OLED device was manufactured in the same manner as in Example 1, except that Compound 118 was used as a light emitting material and Compound D-5 was used as a dopant.
그 결과, 3.8 V의 전압에서 2.22 mA/cm2의 전류가 흘렀으며, 1090 cd/m2의 녹색발광이 확인되었다.
As a result, a current of 2.22 mA / cm 2 flowed at a voltage of 3.8 V, and green light emission of 1090 cd / m 2 was confirmed.
[비교예 1] 종래에 발광재료를 이용한 OLED 소자 제작[Comparative Example 1] Fabrication of OLED device using light emitting material
발광재료로서 호스트에는 4,4‘-N,N'-다이카바졸-바이페닐 (4,4‘-N,N'-dicarbazole-biphenyl), 도판트로는 화합물 D-5을 사용하고, 정공전달층위에 30nm 두께의 발광층을 증착하고, 정공 저지층으로 알루미늄(III)비스(2-메틸-8-퀴놀리네이토)4-페닐페놀레이트 (aluminum(III)bis(2-methyl-8-quinolinato)4-phenylphenolate)을 10nm 두께로 증착한 것 외에는 실시예 1과 동일한 방법으로 OLED소자를 제작하였다.4,4'-N, N'-dicarbazole-biphenyl (4,4'-N, N'-dicarbazole-biphenyl) as a light emitting material and compound D-5 as dopant A light emitting layer having a thickness of 30 nm was deposited on the layer, and aluminum (III) bis (2-methyl-8-quinolinate) 4-phenylphenolate (aluminum (III) bis (2-methyl-8-quinolinato) was used as a hole blocking layer. An OLED device was manufactured in the same manner as in Example 1, except that 10-nm thick 4-phenylphenolate was deposited.
그 결과, 4.9 V의 전압에서 2.86 mA/cm2의 전류가 흘렀으며, 1000 cd/m2의 녹색발광이 확인되었다.
As a result, a current of 2.86 mA / cm 2 flowed at a voltage of 4.9 V, and green light emission of 1000 cd / m 2 was confirmed.
본 발명에서 개발한 유기 발광 화합물들의 발광 특성이 종래의 재료 대비 우수한 특성을 보이는 것을 확인할 수 있었다. 또한 본 발명에 따른 유기 발광 화합물을 발광용 호스트 재료로 사용한 소자는 발광특성이 뛰어날 뿐만 아니라 구동전압을 강하시켜줌으로써 전력효율의 상승을 유도하여 소비전력을 개선시킬 수 있었다.It was confirmed that the luminescence properties of the organic light emitting compounds developed in the present invention showed superior properties compared to the conventional materials. In addition, the device using the organic light emitting compound according to the present invention as a light emitting host material was not only excellent in the light emission characteristics, but also by lowering the driving voltage to increase the power efficiency to improve the power consumption.
Claims (10)
[화학식 1]
[상기 화학식 1에서,
L1 및 L2은 각각 독립적으로 단일결합, 치환 또는 비치환된 (C2-C30)헤테로아릴렌, 치환 또는 비치환된 (C6-C30)아릴렌, 또는 치환 또는 비치환된 (C3-C30)시클로알킬렌이고;
X1 및 X2은 각각 독립적으로 CH 또는 N이며;
Y1 및 Y2는 각각 독립적으로 -O-, -S-, -CR5R6- 또는 -NR7-이며, 단, Y2 와 Y3가 동시에 존재하는 경우는 없고;
Ar은 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (C2-C30)헤테로아릴, 또는 N-카바졸릴이며;
R1 내지 R4은 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (C2-C30)헤테로아릴, 치환 또는 비치환된 (C3-C30)시클로알킬, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된 (C6-C30)아르(C1-C30)알킬, -NR11R12, -SiR13R14R15, -SR16, -OR17, 시아노, 나이트로 또는 하이드록시이거나, 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 치환 또는 비치환된 (C3-C30)알킬렌 또는 치환 또는 비치환된 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있으며, 상기 형성된 지환족 고리 및 단일환 또는 다환의 방향족 고리의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 치환될 수 있고;
R5 내지 R7 및 R11 내지 R17는 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (C2-C30)헤테로아릴, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된 (C3-C30)시클로알킬이거나, 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 치환 또는 비치환된 (C3-C30)알킬렌 또는 치환 또는 비치환된 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있으며, 상기 형성된 지환족 고리 및 단일환 또는 다환의 방향족 고리의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 치환될 수 있고;
a, b, c 및 d는 각각 독립적으로 1 내지 4의 정수이며, 2 이상의 정수인 경우 각각 동일하거나 상이할 수 있고;
상기 헤테로시클로알킬 및 헤테로아릴은 B, N, O, S, P(=O), Si 및 P로부터 선택된 하나 이상의 헤테로원자를 포함한다.]An organic light emitting compound represented by Formula 1 below:
[Formula 1]
[In the above formula (1)
L 1 and L 2 are each independently a single bond, substituted or unsubstituted (C2-C30) heteroarylene, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (C3-C30) Cycloalkylene;
X 1 and X 2 are Each one independently CH or N;
Y 1 and Y 2 are each independently -O-, -S-, -CR 5 R 6 -or -NR 7- , provided that Y 2 and Y 3 are not present at the same time;
Ar is each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C2-C30) heteroaryl, or N Carbazolyl;
R 1 to R 4 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C2-C30) hetero Aryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C6-C30) ar (C1-C30) alkyl, -NR 11 R 12 , -SiR 13 R 14 R 15 , -SR 16 , -OR 17, cyano, nitro or hydroxy, substituted or unsubstituted (C3-C30) with or without adjacent substituents and fused rings Alkylene or substituted or unsubstituted (C3-C30) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, and the alicyclic ring and the monocyclic or polycyclic aromatic ring The carbon atom may be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur;
R 5 to R 7 and R 11 to R 17 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C2-C30) heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C3-C30) cycloalkyl, or a substitution with or without a fused ring with adjacent substituents, or May be linked to an unsubstituted (C3-C30) alkylene or substituted or unsubstituted (C3-C30) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, wherein the alicyclic ring and Carbon atoms of monocyclic or polycyclic aromatic rings may be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur;
a, b, c, and d are each independently an integer of 1 to 4, and when integers of 2 or more, each may be the same or different;
Wherein said heterocycloalkyl and heteroaryl comprise at least one heteroatom selected from B, N, O, S, P (= O), Si and P.
상기 L1, L2, Ar, R1 내지 R7 및 R11 내지 R17에 더 치환되는 치환기는 중수소, 할로겐, (C1-C30)알킬, 할로겐이 치환된 (C1-C30)알킬, (C6-C30)아릴, (C2-C30)헤테로아릴, (C1-C30)알킬이 치환된 (C2-C30)헤테로아릴, (C6-C30)아릴이 치환된 (C2-C30)헤테로아릴, (C3-C30)시클로알킬, 5원 내지 7원의 헤테로시클로알킬, 트리(C1-C30)알킬실릴, 트리(C6-C30)아릴실릴, 디(C1-C30)알킬(C6-C30)아릴실릴, (C1-C30)알킬디(C6-C30)아릴실릴, (C2-C30)알케닐, (C2-C30)알키닐, 시아노, N-카바졸릴, 디(C1-C30)알킬아미노, 디(C6-C30)아릴아미노, (C1-C30)알킬(C6-C30)아릴아미노, 디(C6-C30)아릴보로닐, 디(C1-C30)알킬보로닐, (C1-C30)알킬(C6-C30)아릴보로닐, (C6-C30)아르(C1-C30)알킬, (C1-C30)알킬(C6-C30)아릴, 카르복실, 니트로 및 히드록시로 이루어진 군으로부터 선택되는 하나 이상인 것인 유기 발광 화합물.The method of claim 1,
Substituents further substituted with L 1 , L 2 , Ar, R 1 to R 7 and R 11 to R 17 are deuterium, halogen, (C1-C30) alkyl, (C1-C30) alkyl substituted with halogen, (C6 -C30) aryl, (C2-C30) heteroaryl, (C1-C30) alkyl substituted (C2-C30) heteroaryl, (C6-C30) aryl substituted (C2-C30) heteroaryl, (C3- C30) cycloalkyl, 5- to 7-membered heterocycloalkyl, tri (C1-C30) alkylsilyl, tri (C6-C30) arylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, (C1 -C30) alkyldi (C6-C30) arylsilyl, (C2-C30) alkenyl, (C2-C30) alkynyl, cyano, N-carbazolyl, di (C1-C30) alkylamino, di (C6- C30) arylamino, (C1-C30) alkyl (C6-C30) arylamino, di (C6-C30) arylboronyl, di (C1-C30) alkylboronyl, (C1-C30) alkyl (C6- One or more selected from the group consisting of C30) arylboronyl, (C6-C30) ar (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, carboxyl, nitro and hydroxy Organic light emitting compounds.
상기
[상기 R5, R6 및 R7는 청구항 제1항에서의 정의와 동일하다.]The method of claim 1,
remind
[R 5 , R 6 above And R 7 is identical to the definition in claim 1.
상기 L1 및 L2은 각각 독립적으로 단일결합, (C2-C30)헤테로아릴렌 또는 (C6-C30)아릴렌이고; X1 및 X2은 각각 독립적으로 CH 또는 N이며; Y1 및 Y2는 각각 독립적으로 -O-, -S-, -CR5R6- 또는 -NR7-이며, 단, Y2 와 Y3가 동시에 존재하는 경우는 없고; Ar은 각각 독립적으로 수소, 중수소, 할로겐, (C1-C30)알킬, (C6-C30)아릴, (C2-C30)헤테로아릴, 또는 N-카바졸릴이며; R1 내지 R4은 각각 독립적으로 수소, 중수소, 할로겐, (C1-C30)알킬, (C6-C30)아릴, (C2-C30)헤테로아릴, N-카바졸릴 또는 -SiR13R14R15이고; R5 내지 R7는 각각 독립적으로 (C1-C30)알킬, (C6-C30)아릴 또는 (C2-C30)헤테로아릴이거나, 상기 R5와 R6는 융합고리를 포함하거나 포함하지 않는 치환 또는 비치환된 (C3-C30)알킬렌 또는 치환 또는 비치환된 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있으며, 상기 형성된 지환족 고리 및 단일환 또는 다환의 방향족 고리의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 치환될 수 있고; R13 내지 R15는 각각 독립적으로 (C1-C30)알킬, (C6-C30)아릴 또는 (C2-C30)헤테로아릴이고; 상기 L1 및 L2의 아릴렌 및 헤테로아릴렌, Ar의 알킬, 아릴, 헤테로아릴 및 N-카바졸릴, R1 내지 R4의 알킬, 아릴, 헤테로아릴 및 N-카바졸릴, R5 내지 R7 및 R13 내지 R15의 알킬, 아릴 및 헤테로아릴은 각각 중수소, 할로겐, (C1-C30)알킬, 할로겐이 치환된 (C1-C30)알킬, (C6-C30)아릴, (C2-C30)헤테로아릴, (C1-C30)알킬이 치환된 (C2-C30)헤테로아릴, (C6-C30)아릴이 치환된 (C2-C30)헤테로아릴, (C3-C30)시클로알킬, N-카바졸릴, 디(C1-C30)알킬아미노, 디(C6-C30)아릴아미노, (C1-C30)알킬(C6-C30)아릴아미노, (C6-C30)아르(C1-C30)알킬 및 (C1-C30)알킬(C6-C30)아릴로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 더 치환될 수 있는 것인 유기 발광 화합물.The method of claim 1,
L 1 and L 2 are each independently a single bond, (C2-C30) heteroarylene or (C6-C30) arylene; X 1 And X < 2 & Each one independently CH or N; Y 1 and Y 2 are each independently -O-, -S-, -CR 5 R 6 -or -NR 7- , provided that Y 2 and Y 3 are not present at the same time; Ar is each independently hydrogen, deuterium, halogen, (C1-C30) alkyl, (C6-C30) aryl, (C2-C30) heteroaryl, or N-carbazolyl; R 1 to R 4 are each independently hydrogen, deuterium, halogen, (C 1 -C 30) alkyl, (C 6 -C 30) aryl, (C 2 -C 30) heteroaryl, N-carbazolyl or —SiR 13 R 14 R 15 ; R 5 to R 7 are each independently (C 1 -C 30) alkyl, (C 6 -C 30) aryl or (C 2 -C 30) heteroaryl, wherein R 5 and R 6 are substituted or unsubstituted with or without a fused ring. It may be linked to a ring (C3-C30) alkylene or substituted or unsubstituted (C3-C30) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, the alicyclic ring and monocyclic ring formed above Or the carbon atoms of the polycyclic aromatic ring can be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur; R 13 to R 15 are each independently (C 1 -C 30) alkyl, (C 6 -C 30) aryl or (C 2 -C 30) heteroaryl; Wherein L 1 and L 2 of arylene and heteroarylene, of Ar-alkyl, aryl, heteroaryl, and N- carbazolyl, R 1 to R 4 of the alkyl, aryl, heteroaryl and N- carbazolyl, R 5 to R Alkyl, aryl and heteroaryl of 7 and R 13 to R 15 are deuterium, halogen, (C 1 -C 30) alkyl, halogen substituted (C 1 -C 30) alkyl, (C 6 -C 30) aryl, (C 2 -C 30) Heteroaryl, (C2-C30) heteroaryl substituted with (C1-C30) alkyl, (C2-C30) heteroaryl substituted with (C6-C30) aryl, (C3-C30) cycloalkyl, N-carbazolyl, Di (C1-C30) alkylamino, di (C6-C30) arylamino, (C1-C30) alkyl (C6-C30) arylamino, (C6-C30) ar (C1-C30) alkyl and (C1-C30) An organic light emitting compound that may be further substituted with one or more substituents selected from the group consisting of alkyl (C6-C30) aryl.
하기 화합물로부터 선택되는 유기 발광 화합물.
An organic light-emitting compound selected from the following compounds.
상기 유기 전계 발광 소자가 제1전극; 제2전극; 및 상기 제1전극과 제2전극 사이에 개재되는 1층 이상의 유기물층을 가지며, 이 유기물층이 상기 유기 발광 화합물 중 하나 이상과 하기 화학식 2로 표시되는 인광 도판트 중 하나 이상을 포함하는 것인 유기 전계 발광 소자:
[화학식 2]
M 1 L 101 L 102 L 103
상기 화학식 2에서,
여기서 M1은 Ir, Pt, Pd 및 Os으로 이루어진 군으로부터 선택되고,
리간드 L101, L102 및 L103 는 서로 독립적으로 하기 구조로부터 선택되어진다.
R201 내지 R203은 서로 독립적으로 수소, 중수소, 할로겐이 치환되거나 치환되지 않은 (C1-C30)알킬, (C1-C30)알킬이 치환되거나 치환되지 않은 (C6-C30)아릴 또는 할로겐이고;
R204 내지 R219는 서로 독립적으로 수소, 중수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C1-C30)알콕시, 치환 또는 비치환된(C3-C30)시클로알킬, 치환 또는 비치환된(C2-C30)알케닐, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된 모노 또는 치환 또는 비치환된 디-(C1-C30)알킬아미노, 치환 또는 비치환된 모노 또는 디-(C6-C30)아릴아미노, SF5, 치환 또는 비치환된 트리(C1-C30)알킬실릴, 치환 또는 비치환된 디(C1-C30)알킬(C6-C30)아릴실릴, 치환 또는 비치환된 트리(C6-C30)아릴실릴, 시아노 또는 할로겐이고;
R220 내지 R223는 서로 독립적으로 수소, 중수소, 할로겐이 치환되거나 치환되지 않은 (C1-C30)알킬 또는 (C1-C30)알킬이 치환되거나 치환되지 않은 (C6-C30)아릴이고;
R224 및 R225는 서로 독립적으로 수소, 중수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 할로겐이거나, R224와 R225는 융합고리를 포함하거나 포함하지 않는 (C3-C12)알킬렌 또는 (C3-C12)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성하며;
R226은 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C5-C30)헤테로아릴 또는 할로겐이고;
R227 내지 R229은 서로 독립적으로 수소, 중수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 할로겐이고;
Q는
The organic electroluminescent device comprises a first electrode; A second electrode; And at least one organic material layer interposed between the first electrode and the second electrode, wherein the organic material layer includes at least one of the organic light emitting compounds and at least one phosphorescent dopant represented by Formula 2 below. Light emitting element:
(2)
M 1 L 101 L 102 L 103
In Formula 2,
Wherein M 1 is selected from the group consisting of Ir, Pt, Pd and Os,
The ligands L 101 , L 102 and L 103 are independently selected from the following structures.
R 201 to R 203 independently represent hydrogen, deuterium, (C 1 -C 30) alkyl in which the halogen is optionally substituted (C 1 -C 30) alkyl, (C 6 -C 30) aryl or halogen in which the (C 1 -C 30) alkyl is optionally substituted;
R 204 to R 219 are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C3-C30) cycloalkyl, Substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted mono or substituted or unsubstituted di- (C1-C30) alkylamino, substituted or unsubstituted Substituted mono or di- (C6-C30) arylamino, SF 5 , substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl , Substituted or unsubstituted tri (C6-C30) arylsilyl, cyano or halogen;
R 220 to R 223 are each independently hydrogen, deuterium, (C1-C30) alkyl with or without halogen, or (C6-C30) aryl with or without (C1-C30) alkyl;
R 224 and R 225 are independently of each other hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen, or R 224 and R 225 contain fused rings Linked with (C3-C12) alkylene or (C3-C12) alkenylene with or without formation to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;
R 226 is substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C5-C30) heteroaryl or halogen;
R 227 to R 229 are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen;
Q is
상기 인광 도판트는 하기 화합물로부터 선택되는 것인 유기 전계 발광 소자.
The phosphorescent dopant is selected from the following compounds.
상기 유기물층이 아릴아민계 화합물 또는 스티릴아릴아민계 화합물로 이루어진 군으로부터 선택된 하나 이상의 아민계 화합물(A); 1족, 2족, 4주기, 5주기 전이금속, 란탄계열금속 및 d-전이원소의 유기금속으로 이루어진 군으로부터 선택되는 하나 이상의 금속 또는 금속을 포함하는 착체화합물(B); 또는 이들의 혼합물을 포함하는 것인 유기 전계 발광 소자.8. The method of claim 7,
At least one amine compound (A) wherein the organic material layer is selected from the group consisting of an arylamine compound or a styrylarylamine compound; Complex compounds (B) comprising at least one metal or metal selected from the group consisting of Group 1, Group 2, 4 and 5 cycle transition metals, lanthanide series metals and organic metals of d-transition elements; Or an organic electroluminescent device comprising a mixture thereof.
상기 유기물층이 청색, 적색 또는 녹색 발광을 하는 유기발광층 하나 이상을 더 포함하여 백색 발광을 하는 것인 유기 전계 발광 소자.8. The method of claim 7,
The organic light emitting device of claim 1, wherein the organic material layer further comprises at least one organic light emitting layer emitting blue, red, or green light.
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- 2012-07-20 WO PCT/KR2012/005840 patent/WO2013012297A1/en active Application Filing
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- 2012-07-20 CN CN201280045820.1A patent/CN103827119A/en active Pending
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| US9412956B2 (en) | 2013-09-12 | 2016-08-09 | Semiconductor Energy Laboratory Co., Ltd. | Organometallic iridium complex, light-emitting element, light-emitting device, electronic device, and lighting device |
| KR20160119904A (en) * | 2015-04-06 | 2016-10-17 | 삼성디스플레이 주식회사 | Condensed-cyclic compound and organic light emitting device comprising the same |
| US11937502B2 (en) | 2015-04-14 | 2024-03-19 | Samsung Display Co., Ltd. | Condensed cyclic compound and organic light-emitting device comprising the same |
| US11871661B2 (en) | 2015-12-17 | 2024-01-09 | Samsung Display Co., Ltd. | Organic light-emitting device |
| US9960367B2 (en) | 2015-12-24 | 2018-05-01 | Samsung Electronics Co., Ltd. | Condensed cyclic compound and organic light-emitting device including the same |
| KR20180030350A (en) * | 2016-09-13 | 2018-03-22 | 삼성디스플레이 주식회사 | Condensed-cyclic compound and organic light emitting device comprising the same |
| US11462693B2 (en) | 2018-11-23 | 2022-10-04 | Samsung Display Co., Ltd. | Organic electroluminescence device |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103827119A (en) | 2014-05-28 |
| WO2013012297A1 (en) | 2013-01-24 |
| TW201307336A (en) | 2013-02-16 |
| JP2014525910A (en) | 2014-10-02 |
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