KR20110088118A - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents
Novel organic electroluminescent compounds and organic electroluminescent device using the same Download PDFInfo
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- KR20110088118A KR20110088118A KR1020100007866A KR20100007866A KR20110088118A KR 20110088118 A KR20110088118 A KR 20110088118A KR 1020100007866 A KR1020100007866 A KR 1020100007866A KR 20100007866 A KR20100007866 A KR 20100007866A KR 20110088118 A KR20110088118 A KR 20110088118A
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- KR
- South Korea
- Prior art keywords
- substituted
- unsubstituted
- alkyl
- aryl
- independently
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 72
- 239000002019 doping agent Substances 0.000 claims abstract description 18
- 239000011368 organic material Substances 0.000 claims abstract description 11
- 239000000126 substance Substances 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims description 63
- -1 cyano, carbazolyl Chemical group 0.000 claims description 59
- 239000010410 layer Substances 0.000 claims description 50
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 41
- 125000001072 heteroaryl group Chemical group 0.000 claims description 37
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 150000002367 halogens Chemical class 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 239000012044 organic layer Substances 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 14
- 229910052805 deuterium Inorganic materials 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 229910052751 metal Inorganic materials 0.000 claims description 11
- 239000002184 metal Substances 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 10
- 125000004450 alkenylene group Chemical group 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 125000002950 monocyclic group Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 229910052698 phosphorus Inorganic materials 0.000 claims description 10
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 125000002723 alicyclic group Chemical group 0.000 claims description 6
- 125000005104 aryl silyl group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000003367 polycyclic group Chemical group 0.000 claims description 6
- 229910052710 silicon Inorganic materials 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052796 boron Inorganic materials 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 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 claims description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000005493 quinolyl group Chemical group 0.000 claims description 4
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000005872 benzooxazolyl group Chemical group 0.000 claims description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 claims description 3
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 3
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 150000002739 metals Chemical class 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 125000005561 phenanthryl group Chemical group 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 125000001725 pyrenyl group Chemical group 0.000 claims description 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 claims description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 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 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000005549 heteroarylene group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims 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 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 2
- 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 claims description 2
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 claims description 2
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 2
- 125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 claims description 2
- 125000003003 spiro group Chemical group 0.000 claims description 2
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 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
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 2
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical group [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 230000001939 inductive effect Effects 0.000 abstract description 2
- 238000005401 electroluminescence Methods 0.000 abstract 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- 239000002904 solvent Substances 0.000 description 26
- 238000002360 preparation method Methods 0.000 description 24
- 239000000463 material Substances 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 238000004440 column chromatography Methods 0.000 description 10
- 239000012153 distilled water Substances 0.000 description 10
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000001771 vacuum deposition Methods 0.000 description 6
- 238000000605 extraction Methods 0.000 description 5
- 230000005525 hole transport Effects 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 description 4
- YWLXZCAOJYQMKY-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl.ClC1=CC=CC=C1Cl YWLXZCAOJYQMKY-UHFFFAOYSA-N 0.000 description 4
- MZSAMHOCTRNOIZ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylaniline Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(NC2=CC=CC=C2)C=CC=1 MZSAMHOCTRNOIZ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N ortho-dichlorobenzene Natural products ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 3
- WSNKEJIFARPOSQ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-(1-benzothiophen-2-ylmethyl)benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCC2=CC3=C(S2)C=CC=C3)C=CC=1 WSNKEJIFARPOSQ-UHFFFAOYSA-N 0.000 description 3
- GDSLUYKCPYECNN-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-[(4-fluorophenyl)methyl]benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCC2=CC=C(C=C2)F)C=CC=1 GDSLUYKCPYECNN-UHFFFAOYSA-N 0.000 description 3
- HAEQAUJYNHQVHV-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylbenzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NC2=CC=CC=C2)C=CC=1 HAEQAUJYNHQVHV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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
- REAYFGLASQTHKB-UHFFFAOYSA-N [2-[3-(1H-pyrazol-4-yl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound N1N=CC(=C1)C=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 REAYFGLASQTHKB-UHFFFAOYSA-N 0.000 description 3
- SAHIZENKTPRYSN-UHFFFAOYSA-N [2-[3-(phenoxymethyl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound O(C1=CC=CC=C1)CC=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 SAHIZENKTPRYSN-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
- 150000004770 chalcogenides Chemical class 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 2
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group 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 2
- 150000001204 N-oxides Chemical class 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 2
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 150000002910 rare earth metals Chemical class 0.000 description 2
- 230000027756 respiratory electron transport chain Effects 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 125000004306 triazinyl group Chemical group 0.000 description 2
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- 125000006654 (C3-C12) heteroaryl group Chemical group 0.000 description 1
- 125000006651 (C3-C20) cycloalkyl group Chemical group 0.000 description 1
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- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 1
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- BTTNYQZNBZNDOR-UHFFFAOYSA-N 2,4-dichloropyrimidine Chemical compound ClC1=CC=NC(Cl)=N1 BTTNYQZNBZNDOR-UHFFFAOYSA-N 0.000 description 1
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
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- LVDRREOUMKACNJ-BKMJKUGQSA-N N-[(2R,3S)-2-(4-chlorophenyl)-1-(1,4-dimethyl-2-oxoquinolin-7-yl)-6-oxopiperidin-3-yl]-2-methylpropane-1-sulfonamide Chemical compound CC(C)CS(=O)(=O)N[C@H]1CCC(=O)N([C@@H]1c1ccc(Cl)cc1)c1ccc2c(C)cc(=O)n(C)c2c1 LVDRREOUMKACNJ-BKMJKUGQSA-N 0.000 description 1
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- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
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- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-N aluminum;quinolin-8-ol Chemical compound [Al+3].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000002078 anthracen-1-yl 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 1
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
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- 150000001768 cations Chemical class 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
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- 238000001704 evaporation Methods 0.000 description 1
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- ZWJINEZUASEZBH-UHFFFAOYSA-N fenamic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=CC=C1 ZWJINEZUASEZBH-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
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- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 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 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 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
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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Abstract
Description
본 발명은 신규한 유기 발광 화합물 및 이를 포함하고 있는 유기 전계 발광 소자에 관한 것으로, 보다 구체적으로는 발광 재료로서 사용되는 신규한 유기 발광 화합물 및 이를 호스트로서 채용하고 있는 유기 전계 발광 소자에 관한 것이다.The present invention relates to a novel organic light emitting compound and an organic electroluminescent device comprising the same, and more particularly to a novel organic light emitting compound used as a light emitting material and an organic electroluminescent device employing the same as a host.
유기 EL 소자에서 발광 효율, 수명 등의 성능을 결정하는 가장 중요한 요인은 발광 재료로서, 이러한 발광 재료에 요구되는 몇 가지 특성으로는 고체 상태에서 형광 양자 수율이 커야하고, 전자와 정공의 이동도가 높아야 하며, 진공 증착 시 쉽게 분해되지 않아야 하고, 균일한 박막을 형성, 안정해야한다. In organic EL devices, the most important factor that determines the performance of light emission efficiency, lifetime, etc. is a light emitting material. Some characteristics required for such a light emitting material include high quantum fluorescence yield in the solid state, and mobility of electrons and holes. It should be high, not easily decomposed during vacuum deposition, and a stable thin film should be formed.
유기 전계 발광 소자는 보통 양극/정공주입층/정공수송층/발광층/전자수송층/전자주입층/음극과 같은 다층 구조로 구성되는데 발광층(EML)을 어떻게 형성하느냐에 따라 청색, 녹색, 적색의 3가지 색을 쉽게 구현할 수 있기 때문에 차세대 평판디스플레이에 적합한 소자이다.The organic electroluminescent device is usually composed of a multilayer structure such as an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode. The three colors of blue, green, and red vary depending on how the EML is formed. This device is suitable for the next generation flat panel display because it can be easily implemented.
발광재료는 기능적인 측면에서 호스트 재료와 도판트 재료로 구분될 수 있는데 일반적으로 EL 특성이 가장 우수한 소자 구조로는 호스트에 도판트를 도핑하여 발광층을 만드는 것으로 알려져 있다. 최근에 고효율, 장수명 유기전계발광소자의 개발이 시급한 과제로 대두되고 있으며, 특히 중대형 OLED 패널에서 요구하고 있는 EL 특성 수준을 고려해 볼 때 기존의 발광재료에 비해 매우 우수한 재료의 개발이 시급한 실정이다.The light emitting material can be classified into a host material and a dopant material in terms of its function. In general, a device structure having excellent EL characteristics is known to make a light emitting layer by doping a host with a dopant. Recently, the development of high efficiency and long life organic light emitting diodes has emerged as an urgent task. In particular, considering the EL characteristic level required for medium and large OLED panels, it is urgent to develop materials that are much superior to existing light emitting materials.
본 발명의 목적은 상기한 문제점들을 해결하기 위하여 기존의 호스트 재료보다 발광 효율 및 소자 수명이 좋으며, 적절한 색좌표를 갖는 우수한 골격의 유기 발광 화합물을 제공하는 것이며, 또 다른 목적으로서 상기 유기 발광 화합물을 발광 재료로서 채용하는 고효율 및 장수명의 유기 전계 발광 소자를 제공하는 것이다.Disclosure of Invention An object of the present invention is to provide an organic light emitting compound having an excellent luminescence efficiency and device lifetime, and having an appropriate color coordinate, in order to solve the above problems, and to emit the organic light emitting compound as another object. It is to provide an organic electroluminescent device having high efficiency and long life, which is employed as a 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 호스트 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 luminous efficiency and excellent life characteristics of the material than the conventional host material to drive the device In addition to having a very long lifespan, there is an advantage of manufacturing an OLED device having improved power consumption by inducing an increase in power efficiency.
[화학식 1][Formula 1]
[상기 화학식 1에서,[In Formula 1,
A고리는 또는 이고;A ring or ego;
X는 -C(R12)(R13)-, -N(R14)-, -S-, -O- 또는 -Si(R15)(R16)-이며;X is -C (R 12 ) (R 13 )-, -N (R 14 )-, -S-, -O- or -Si (R 15 ) (R 16 )-;
Ar1 및 Ar2는 서로 독립적으로 치환 또는 비치환된(C6-C30)아릴렌 또는 치환 또는 비치환된(C3-C30)헤테로아릴렌이고; Ar3 내지 Ar5는 서로 독립적으로 치환 또는 비치환된(C6-C30)아릴 또는 치환 또는 비치환된(C3-C30)헤테로아릴이며;Ar 1 and Ar 2 are each independently substituted or unsubstituted (C6-C30) arylene or substituted or unsubstituted (C3-C30) heteroarylene; Ar 3 to Ar 5 are each independently substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl;
R1 내지 R16은 서로 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C3-C30)시클로알킬이 하나 이상 융합된 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C3-C30)헤테로아릴, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된(C3-C30)시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 (C3-C30)시클로알킬, 시아노, 나이트로, NR21R22, BR23R24, PR25R26, P(=O)R27R28, R29R30R31Si-, R32Y-, 치환 또는 비치환된(C6-C30)아르(C1-C30)알킬, 치환 또는 비치환된(C2-C30)알케닐, 치환 또는 비치환된(C2-C30)알키닐, , , 이거나, 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리, 단일환 또는 다환의 헤테로방향족고리를 형성할 수 있고; 상기 B고리 및 C고리는 서로 독립적으로 치환 또는 비치환된(C5-C30)사이클로알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C6-C30)헤테로아릴이며; 상기 R21 내지 R32는 서로 독립적으로 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 치환 또는 비치환된(C3-C30)헤테로아릴이고; 상기 Y는 S 또는 O이며; W는 -(CR51R52)m-, -(R51)C=C(R52)-, -N(R53)-, -S-, -O-, -Si(R54)(R55)-, -P(R56)-, -P(=O)(R57)-, -C(=O)- 또는 -B(R58)-이고, R41 내지 R43 및 R51 내지 R58은 상기 R1 내지 R16에서의 정의와 동일하며; 상기 헤테로시클로알킬, 헤테로아릴 및 헤테로방향족고리는 B, N, O, S, P(=O), Si 및 P로부터 선택된 하나 이상의 헤테로원자를 포함하고; m은 0 내지 2의 정수이며; a, b는 0 내지 4의 정수이고; a, b가 2 이상일 경우에는 서로 동일하거나 상이할 수 있다.]
R 1 to R 16 are independently of each other hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) cyclo Substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted, with one or more alkyl fused To 7-membered heterocycloalkyl fused with one or more aromatic rings, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted aromatic rings with one or more fused (C3-C30) cycloalkyl , Cyano, nitro, NR 21 R 22 , BR 23 R 24 , PR 25 R 26 , P (= O) R 27 R 28 , R 29 R 30 R 31 Si-, R 32 Y-, substituted or unsubstituted Substituted (C6-C30) ar (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl, , , Or an alicyclic ring and a monocyclic or polycyclic aromatic ring, monocyclic or polycyclic heteroaromatic linked with (C3-C30) alkylene or (C3-C30) alkenylene with or without adjacent substituents and fused rings May form a ring; Ring B and ring C are independently substituted or unsubstituted (C5-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C6-C30) heteroaryl; R 21 to R 32 are each independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl; Y is S or O; W is-(CR 51 R 52 ) m -,-(R 51 ) C = C (R 52 )-, -N (R 53 )-, -S-, -O-, -Si (R 54 ) (R 55 )-, -P (R 56 )-, -P (= 0) (R 57 )-, -C (= 0)-or -B (R 58 )-, and R 41 to R 43 and R 51 to R 58 is the same as defined above for R 1 to R 16 ; The heterocycloalkyl, heteroaryl and heteroaromatic ring comprises one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P; m is an integer from 0 to 2; a, b are integers from 0 to 4; When a and b are 2 or more, they may be the same as or different from each other.]
또한 구체적으로 상기 는 하기 구조로 예시될 수 있으나 이에 한정하지는 않는다.Also specifically above May be illustrated by the following structure, but is not limited thereto.
[R1 내지 R10 및 R12 내지 R16은 서로 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C3-C30)헤테로아릴, NR21R22, BR23R24, PR25R26, P(=O)R27R28, R29R30R31Si- 또는 R32Y-이거나, 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리, 단일환 또는 다환의 헤테로방향족고리를 형성할 수 있으며; 상기 R21 내지 R32는 서로 독립적으로 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 치환 또는 비치환된(C3-C30)헤테로아릴이고; 상기 Y는 S 또는 O이며; 상기 헤테로아릴 및 헤테로방향족고리는 B, N, O, S, P(=O), Si 및 P로부터 선택된 하나 이상의 헤테로원자를 포함한다.]
[R 1 to R 10 and R 12 to R 16 are independently of each other hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, NR 21 R 22 , BR 23 R 24 , PR 25 R 26 , P (= O) R 27 R 28 , R 29 R 30 R 31 Si- or R 32 Y- or adjacent Linked with (C3-C30) alkylene or (C3-C30) alkenylene with or without fused ring substituents to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, monocyclic or polycyclic heteroaromatic ring Can do it; R 21 to R 32 are each independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl; Y is S or O; Wherein said heteroaryl and heteroaromatic rings comprise 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. 또한 본 발명의 화학구조에 표시된 *는 구조 내 결합되는 부분을 의미한다. Substituents comprising the 'alkyl', 'alkoxy' and other 'alkyl' moieties described herein include both straight or crushed forms, and 'cycloalkyl' is substituted or unsubstituted as well as a single ring system Or several ring-based hydrocarbons such as substituted or unsubstituted (C7-C30) bicycloalkyl. In addition, * indicated in the chemical structure of the present invention means a part bonded in the structure.
본 발명에 기재된 ‘아릴’은 하나의 수소 제거에 의해서 방향족 탄화수소로부터 유도된 유기 라디칼로, 4 내지 7원, 바람직하게는 5 또는 6원을 포함하는 단일 또는 융합고리계를 포함하며, 하나 이상의 아릴이 화학결합을 통하여 결합되어 있는 구조도 포함한다. 상기 아릴의 구체적인 예로 페닐, 나프틸, 비페닐, 안트릴, 인데닐(indenyl), 플루오레닐, 페난트릴, 트라이페닐레닐, 피렌일, 페릴렌일, 크라이세닐, 나프타세닐, 플루오란텐일 등을 포함하지만, 이에 한정되지 않는다. 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 6원의 단환 헤테로아릴 또는 하나 이상의 벤젠환과 축합된 다환식 헤테로아릴이며, 부분적으로 포화될 수도 있다. 또한, 본 발명에서의 헤테로아릴은 하나 이상의 헤테로아릴이 화학결합을 통하여 결합되어 있는 구조도 포함한다. 상기 헤테로아릴기는 고리 내 헤테로원자가 산화되거나 사원화되어, 예를 들어 N-옥사이드 또는 4차 염을 형성하는 2가 아릴 그룹을 포함한다. 상기 헤테로아릴의 구체적인 예로 퓨릴, 티오펜일, 피롤릴, 이미다졸릴, 피라졸릴, 티아졸릴, 티아디아졸릴, 이소티아졸릴, 이속사졸릴, 옥사졸릴, 옥사디아졸릴, 트리아진일, 테트라진일, 페나진일, 페노티아진일, 페노옥사진일, 트리아졸릴, 테트라졸릴, 퓨라잔일, 피리딜, 피라진일, 피리미딘일, 피리다진일 등의 단환 헤테로아릴, 벤조퓨란일, 벤조티오펜일, 디벤조퓨란일, 디벤조티오펜일, 이소벤조퓨란일, 벤조이미다졸릴, 벤조티아졸릴, 벤조이소티아졸릴, 벤조이속사졸릴, 벤조옥사졸릴, 이소인돌릴, 인돌릴, 인다졸릴, 벤조티아디아졸릴, 퀴놀릴, 이소퀴놀릴, 신놀리닐, 퀴나졸리닐, 퀴녹살리닐, 카바졸릴, 카보리닐, 페난트리딘일, 벤조디옥솔릴 등의 다환식 헤테로아릴 및 이들의 상응하는 N-옥사이드(예를 들어, 피리딜 N-옥사이드, 퀴놀릴 N-옥사이드), 이들의 4차 염 등을 포함하지만, 이에 한정되지 않는다.'Aryl' described in the present invention is an organic radical derived from an aromatic hydrocarbon by one hydrogen removal, and includes a single or fused ring system containing 4 to 7 members, preferably 5 or 6 members, and at least one aryl It also includes structures bonded through this chemical bond. Specific examples of the aryl include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, peryleneyl, chrysenyl, naphthacenyl, fluoranthenyl and the like. Including but not limited to. 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 includes 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. It means an aryl group which is a 5-6 membered monocyclic heteroaryl or polycyclic heteroaryl condensed with one or more benzene rings, and may be partially saturated. In addition, heteroaryl in the present invention also includes a structure in which one or more heteroaryl is bonded through a chemical 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 of the heteroaryl include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxdiazolyl, triazinyl, tetrazinyl, Monocyclic heteroaryl such as phenazinyl, phenothiazineyl, phenooxazineyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, Dibenzofuranyl, dibenzothiophenyl, isobenzofuranyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzooxazolyl, isoindolinyl, indolyl, indazolyl, benzothia Polycyclic heteroaryls such as diazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, carborinyl, phenanthridinyl, benzodioxolyl and their corresponding N-oxides (E.g., pyridyl N-oxide, quinolyl N-oxa D), quaternary salts thereof, and the like, but are not limited thereto.
또한, 본 발명에 기재되어 있는 ‘(C1-C30)알킬’기는 (C1-C20)알킬 또는 (C1-C10)알킬을 포함하고, ‘(C6-C30)아릴’기는 (C6-C20)아릴 또는 (C6-C12)아릴을 포함한다. ‘(C3-C30)헤테로아릴’기는 (C3-C20)헤테로아릴 또는 (C3-C12)헤테로아릴을 포함하고, ‘(C3-C30)시클로알킬’기는 (C3-C20)시클로알킬 또는 (C3-C7)시클로알킬을 포함한다. ‘(C2-C30)알케닐 또는 알키닐’기는 (C2-C20)알케닐 또는 알키닐, (C2-C10)알케닐 또는 알키닐을 포함한다.In addition, the '(C1-C30) alkyl' groups described herein include (C1-C20) alkyl or (C1-C10) alkyl, and the '(C6-C30) aryl' group is a (C6-C20) aryl or (C6-C12) aryl. '(C3-C30) heteroaryl' group includes (C3-C20) heteroaryl or (C3-C12) heteroaryl, and the '(C3-C30) cycloalkyl' group is (C3-C20) cycloalkyl or (C3- C7) cycloalkyl. '(C2-C30) alkenyl or alkynyl' groups include (C2-C20) alkenyl or alkynyl, (C2-C10) alkenyl or alkynyl.
또한 본 발명의 ‘치환 또는 비치환된’이라는 기재에서 ‘치환’은 비치환된 치환기에 더 치환되는 경우를 뜻하며, 상기 Ar1 내지 Ar5, R1 내지 R16, R21 내지 R32, R41 내지 R43, R51 내지 R58에 더 치환되는 치환기는 서로 독립적으로 중수소, 할로겐, 할로겐이 치환 또는 비치환된(C1-C30)알킬, (C6-C30)아릴, (C6-C30)아릴이 치환 또는 비치환된(C3-C30)헤테로아릴, (C3-C30)헤테로아릴, 5원 내지 7원의 헤테로시클로알킬, 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬, (C3-C30)시클로알킬, 방향족고리가 하나이상 융합된 (C3-C30)시클로알킬, NR61R62, BR63R64, PR65R66, P(=O)R67R68, R69R70R71Si-, R72Z-, R73C(=O)-, R74C(=O)O-, (C2-C30)알케닐, (C2-C30)알키닐, 시아노, 카바졸릴, (C6-C30)아르(C1-C30)알킬, (C1-C30)알킬(C6-C30)아릴, 카르복실, 나이트로 또는 하이드록시로 이루어진 군으로부터 선택되는 하나 이상으로 더 치환되거나, 서로 인접한 치환체가 연결되어 고리를 형성할 수 있고; 상기 R61 내지 R72는 서로 독립적으로 (C1-C30)알킬, (C6-C30)아릴 또는 (C3-C30)헤테로아릴이며; 상기 Z는 S 또는 O이고; 상기 R73 및 R74는 서로 독립적으로 (C1-C30)알킬, (C1-C30)알콕시, (C6-C30)아릴 또는 (C6-C30)아릴옥시를 포함한다.In addition, in the description of "substituted or unsubstituted" in the description of "substituted" means a case that is further substituted with an unsubstituted substituent, the Ar 1 To Ar 5 , R 1 To R 16 , R 21 to R 32 , R 41 to R 43 , and R 51 to R 58 are each independently substituted with deuterium, halogen, halogen substituted or unsubstituted (C1-C30) alkyl, (C6 -C30) aryl, (C6-C30) aryl substituted or unsubstituted (C3-C30) heteroaryl, (C3-C30) heteroaryl, 5- to 7-membered heterocycloalkyl, aromatic ring at least one fused 5- to 7-membered heterocycloalkyl, (C3-C30) cycloalkyl, (C3-C30) cycloalkyl fused with one or more aromatic rings, NR 61 R 62 , BR 63 R 64 , PR 65 R 66 , P ( = O) R 67 R 68 , R 69 R 70 R 71 Si-, R 72 Z-, R 73 C (= O)-, R 74 C (= O) O-, (C2-C30) alkenyl, ( C2-C30) alkynyl, cyano, carbazolyl, (C6-C30) ar (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, carboxyl, nitro or hydroxy May be further substituted with one or more selected from or substituents adjacent to each other may be connected to form a ring; R 61 above To R 72 independently of one another are (C1-C30) alkyl, (C6-C30) aryl or (C3-C30) heteroaryl; Z is S or O; R 73 above And R 74 independently of one another includes (C 1 -C 30) alkyl, (C 1 -C 30) alkoxy, (C 6 -C 30) aryl or (C 6 -C 30) aryloxy.
상기 는 하기 구조에서 선택되며, 이에 한정되지는 않는다.remind Is selected from the following structures, but is not limited thereto.
[R81 내지 R109는 서로 독립적으로 수소, (C6-C30)아릴, (C3-C30)헤테로아릴 또는 트리(C6-C30)아릴실릴이다.][R 81 To R 109 are independently of each other hydrogen, (C6-C30) aryl, (C3-C30) heteroaryl or tri (C6-C30) arylsilyl.]
더 바람직하게 상기 는 하기 구조에서 선택되며, 이에 한정되지는 않는다.More preferably Is selected from the following structures, but is not limited thereto.
또한 상기 R1 내지 R16은 서로 독립적으로 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, 플루오르, 시아노, 메톡시, 에톡시, n-프로폭시, i-프로폭시, n-부톡시, i-부톡시, t-부톡시, n-펜톡시, i-펜톡시, n-헥실옥시, n-헵톡시, 시클로프로필, 시클로부틸, 시클로펜틸, 시클로헥실, 시클로헵틸, 시클로옥틸, 시클로노닐, 시클로데실, 트리플루오르메틸, 퍼플루오르에틸, 트리플루오르에틸, 퍼플루오르프로필, 퍼플루오르부틸, 페닐, 나프틸, 비페닐, 플루오레닐, 페난트릴, 안트릴, 플루오란텐일, 트리페닐렌일, 피렌일, 크라이세닐, 나프타세닐, 페릴렌일, 피리딜, 피롤릴, 퓨란일, 티오펜일, 이미다졸릴, 벤조이미다졸릴, 피라진일, 피리미딘일, 피리다진일, 퀴놀릴, 트리아진일, 디페닐트리아진일, 페노티아진일, 벤조퓨란일, 벤조티오펜일, 디벤조퓨란일, 디벤조티오페닐, 피라졸릴, 인돌릴, N-페닐피리도인돌릴, N-페닐피라지노인돌릴, 카바졸릴, N-페닐카바졸릴, N-페닐벤조카바졸릴, 티아졸릴, 옥사졸릴, 벤조티아졸릴, 벤조옥사졸릴, 트리메틸실릴, 트리에틸실릴, 트리프로필실릴, 트리(t-부틸)실릴, t-부틸디메틸실릴, 디메틸페닐실릴, 트리페닐실릴 또는 벤질에서 선택되며, 이에 한정되지는 않는다.Also above R 1 To R 16 are independently of each other 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, fluorine, cyano, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy , t-butoxy, n-pentoxy, i-pentoxy, n-hexyloxy, n-heptoxy, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl Trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, naphthyl, biphenyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, Chrysenyl, naphthacenyl, peryleneyl, pyridyl, pyrrolyl, furanyl, thiophenyl, imidazolyl, benzoimidazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, triazinyl, Phenyltriazinyl, phenothiazineyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyrazolyl, indolyl, N-phenylpyridoindolyl, N-phenylpyrazinoindolyl, carba Zolyl, N-phenylcarbazolyl, N-phenylbenzocarbazolyl, thiazolyl, oxazolyl, benzothiazolyl, benzooxazolyl, trimethylsilyl, triethylsilyl, tripropylsilyl, tri (t-butyl) silyl, t- Butyldimethylsilyl, dimethylphenylsilyl, triphenylsilyl or benzyl, but is not limited thereto.
더 바람직하게 상기 R1 내지 R16은 하기 구조에서 선택되며, 이에 한정되지는 않는다.More preferably R 1 To R 16 is selected from the following structures, but is not limited thereto.
본 발명에 따른 유기 발광 화합물은 보다 구체적으로 하기의 화합물로서 예시될 수 있으나, 하기 화합물이 본 발명을 한정하는 것은 아니다.The organic light emitting compound according to the present invention may be more specifically exemplified as the following compound, but the following compound does not limit the present invention.
본 발명에 따른 유기 발광 화합물은 하기 반응식 1에 나타난 바와 같이, 제조될 수 있다.The organic light emitting compound according to the present invention can be prepared as shown in Scheme 1 below.
[반응식 1]Scheme 1
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 유기물층으로 이루어진 유기 전계 발광 소자에 있어서, 상기 유기물층은 상기 화학식 1의 유기 발광 화합물을 하나 이상 포함하는 것을 특징으로 한다. 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화학식 1의 유기 발광 화합물 하나 이상을 호스트로 하여 하나 이상의 도판트를 포함하는 것을 특징으로 한다. 본 발명의 유기 전계 발광 소자에 적용되는 도판트는 특별히 제한되지는 않으나, 본 발명의 유기 전계 발광 소자에 적용되는 도판트는 하기 화학식 2로 표시되는 화합물로부터 선택되는 것이 바람직하다.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 organic light emitting compound of Formula 1. The organic material layer may include a light emitting layer, and the light emitting layer may include one or more dopants using at least one organic light emitting compound of Formula 1 as a host. The dopant applied to the organic electroluminescent device of the present invention is not particularly limited, but the dopant applied to the organic electroluminescent device of the present invention is preferably selected from a compound represented by the following formula (2).
[화학식 2] [Formula 2]
M1L101L102L103 M 1 L 101 L 102 L 103
[상기 화학식 2에서,[In the formula (2)
M1은 7족, 8족, 9족, 10족, 11족, 13족, 14족, 15족 및 16족의 금속으로 이루어진 군으로부터 선택되고, 리간드 L101, L102 및 L103 는 서로 독립적으로 하기 구조로부터 선택되며;M 1 is selected from the group consisting of metals of Groups 7, 8, 9, 10, 11, 13, 14, 15 and 16, and ligands L 101 , L 102 and L 103. Are independently selected from the following structures;
R201 내지 R203은 서로 독립적으로 수소, 할로겐이 치환되거나 치환되지 않은 (C1-C30)알킬, (C1-C30)알킬이 치환되거나 치환되지 않은 (C6-C30)아릴 또는 할로겐이고; R204 내지 R219는 서로 독립적으로 수소, 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 R223은 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 R229는 서로 독립적으로 수소, 중수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 할로겐이고;R 201 to R 203 are independently of each other hydrogen, (C1-C30) alkyl with or without halogen, (C6-C30) aryl or halogen with or without (C1-C30) alkyl; R 204 to R 219 are each independently hydrogen, 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 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;
Q는 , 또는 이며, R231 내지 R242는 서로 독립적으로 수소, 중수소, 할로겐이 치환되거나 치환되지 않은 (C1-C30)알킬, (C1-C30)알콕시, 할로겐, 치환 또는 비치환된(C6-C30)아릴, 시아노, 치환 또는 비치환된(C5-C30)시클로알킬이거나, 인접한 치환체와 알킬렌 또는 알케닐렌으로 연결되어 스피로 고리 또는 융합고리를 형성할 수 있거나, R207 또는 R208과 알킬렌 또는 알케닐렌으로 연결되어 포화 또는 불포화의 융합고리를 형성할 수 있다.]Q is , or R 231 to R 242 are each independently of the other hydrogen, deuterium, (C1-C30) alkyl, (C1-C30) alkoxy, halogen, substituted or unsubstituted (C6-C30) aryl, Cyano, substituted or unsubstituted (C5-C30) cycloalkyl, or may be linked to adjacent substituents with alkylene or alkenylene to form a spiro ring or fused ring, or with R 207 or R 208 and alkylene or alkenylene To form a saturated or unsaturated fused ring.]
상기 화학식 2의 도판트 화합물은 하기 구조의 화합물로 예시될 수 있으나 이에 한정하는 것은 아니다.The dopant compound of Formula 2 may be exemplified as a compound having the following structure, but is not limited thereto.
본 발명의 유기 전계 발광 소자는 상기 화학식 1의 유기 발광 화합물을 포함하고, 동시에 아릴아민계 화합물 또는 스티릴아릴아민계 화합물로 이루어진 군으로부터 선택된 하나 이상의 화합물을 포함할 수 있으며, 상기 아릴아민계 화합물 또는 스티릴아릴아민계 화합물은 한국특허출원번호 제10-2008-0123276호, 제10-2008-0107606호 또는 제10-2008-0118428호에 예시된 것도 포함하나, 이에 한정되지는 않는다. The organic electroluminescent device of the present invention may include one or more compounds selected from the group consisting of an organic light emitting compound of Formula 1 and an arylamine compound or a styrylarylamine compound, and the arylamine compound Or styrylarylamine-based compounds include, but are not limited to, those exemplified in Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606, or 10-2008-0118428.
또한, 본 발명의 유기 전계 발광 소자에 있어서, 유기물층에 상기 화학식 1의 유기 발광 화합물 이외에 1족, 2족, 4주기, 5주기 전이금속, 란탄계열금속 및 d-전이원소의 유기금속으로 이루어진 군으로부터 선택되는 하나 이상의 금속 또는 착체화합물을 더 포함할 수도 있고, 상기 유기물층은 발광층 및 전하생성층을 포함할 수 있다.In addition, in the organic electroluminescent device of the present invention, in the organic material layer, in addition to the organic light emitting compound of Chemical Formula 1, a group consisting of Group 1, Group 2, 4 cycle, 5 cycle transition metal, lanthanide series metal and organic metal of d-transition element It may further comprise one or more metals or complex compounds selected from, the organic material layer may include a light emitting layer and a charge generating layer.
또한, 상기 유기물층에 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. 상기 청색, 녹색 또는 적색 발광을 하는 화합물은 한국특허출원번호 제10-2008-0123276호, 제10-2008-0107606호 또는 제10-2008-0118428호에 예시되어 있으나, 이에 한정되지는 않는다. In addition, an organic electroluminescent device that emits white light may be formed by simultaneously including one or more organic light emitting layers including blue, red, or green light emitting compounds in addition to the organic light emitting compound. The compound emitting blue, green, or red light is exemplified in Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606, or 10-2008-0118428, but is not limited thereto.
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 칼코제나이드로서는 예컨대 SiOx(1≤X≤2), AlOX(1≤X≤1.5), SiON, SiAlON 등을 바람직하게 들 수 있으며, 할로겐화 금속으로서는 예컨대 LiF, MgF2, CaF2, 불화 희토류 금속 등을 바람직하게 들 수 있으며, 금속 산화물로서는 예컨대 Cs2O, Li2O, MgO, SrO, BaO, CaO 등을 바람직하게 들 수 있다.In the organic electroluminescent device of the present invention, one layer selected from a chalcogenide layer, a halogenated metal layer, and a metal oxide layer on at least one inner surface of a pair of electrodes (hereinafter, these are referred to as 'surface layers'). It is preferable to arrange | position the above. 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. Examples of the chalcogenide include SiO x (1 ≦ X ≦ 2 ), AlO X (1 ≦ X ≦ 1.5), SiON, SiAlON, and the like, and examples of the metal halide include LiF, MgF 2 , CaF 2 , and fluoride. Rare earth metals and the like are preferable. 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 방식으로, 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 있다. 바람직한 환원성 도판트로서는 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 도 있다.Further, in the organic electroluminescent device of the present invention, disposing a mixed region of an electron transfer compound and a reducing dopant or a mixed region of a hole transfer compound and an oxidative dopant on at least one surface of the pair of electrodes thus produced desirable. In this way, the electron transfer compound is reduced to an anion, thereby facilitating injection and transfer of electrons from the mixed region into 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.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.
이하에서, 본 발명의 상세한 이해를 위하여 본 발명의 대표 화합물을 들어 본 발명에 따른 유기 발광 화합물, 이의 제조방법 및 소자의 발광특성을 설명하나, 이는 단지 그 실시 양태를 예시하기 위한 것일 뿐, 본 발명의 범위를 한정하는 것은 아니다.Hereinafter, the organic light emitting compound according to the present invention, a method for preparing the same and a light emitting property of the device are described for the detailed understanding of the present invention, but the present invention is only intended to illustrate the embodiments of the present invention. It does not limit the scope of the invention.
[제조예 1] 화합물 13의 제조Preparation Example 1 Preparation of Compound 13
화합물 1-1의 제조Preparation of Compound 1-1
2-(페닐아미노)벤조산(2-(phenylamino)benzoic acid) 50 g(0.23 mol)을 MeOH 1 L에 녹이고, ice bath에 넣어 10분간 교반하였다. 0 ℃에서 SOCl2 60 mL(0.58 mol)를 천천히 첨가한 후 90 ℃에서 12시간 동안 환류 교반하였다. 반응이 종결되면, 증류수로 세척하고 에틸아세테이트로 추출하였다. 유기층을 MgSO4로 건조시킨 후 회전 증발기로 용매를 제거하고, 에틸아세테이트를 전개 용매로하여 컬럼크로마토그래피로 정제하여 화합물 1-1 47 g(92%)를 얻었다.50 g (0.23 mol) of 2- (phenylamino) benzoic acid was dissolved in 1 L of MeOH, and stirred in an ice bath for 10 minutes. 60 mL (0.58 mol) of SOCl 2 was slowly added at 0 ° C., followed by stirring under reflux at 90 ° C. for 12 hours. When the reaction was terminated, washed with distilled water and extracted with ethyl acetate. The organic layer was dried over MgSO 4 , and the solvent was removed using a rotary evaporator. The mixture was purified by column chromatography with ethyl acetate as a developing solvent, to obtain compound 1-1 47 g (92%).
화합물 1-2의 제조Preparation of Compound 1-2
화합물 1-1 90 g(0.3 mol)를 THF 1.5 L에 넣고, MeMgBr(3.0M) 462 mL(1.38 mol)를 천천히 첨가한 후 실온에서 12시간 동안 교반하였다. 반응이 종결되면, 증류수로 중화하고, 에틸아세테이트로 추출하였다. 유기층을 MgSO4로 건조시킨 후 회전 증발기로 용매를 제거하고, 에틸아세테이트를 전개 용매로하여 컬럼크로마토그래피로 정제하여 화합물 1-2 80 g(90%)를 얻었다. 90 g (0.3 mol) of Compound 1-1 was added to 1.5 L of THF, and 462 mL (1.38 mol) of MeMgBr (3.0M) was added slowly, followed by stirring at room temperature for 12 hours. After the reaction was completed, the mixture was neutralized with distilled water and extracted with ethyl acetate. The organic layer was dried over MgSO 4 , and the solvent was removed using a rotary evaporator. Purification by column chromatography using ethyl acetate as a developing solvent gave 80 g (90%) of compound 1-2.
화합물 1-3의 제조Preparation of Compound 1-3
화합물 1-2 80 g(0.35 mol)를 H3PO4 1.7 L에 넣은 후 실온에서 12시간 동안 교반하였다. 반응이 종결되면, 증류수로 중화하고, 생성된 고체를 물로 씻어주면서 여과하였다. 고체를 다이클로로메탄(dichloromethane)으로 녹여서 추출하고, NaOH로 중화시켰다. 유기층을 MgSO4로 건조시킨 후 회전 증발기로 용매를 제거하고, 헥산으로 재결정하여 화합물 1-3 64 g(87%)를 얻었다.80 g (0.35 mol) of Compound 1-2 was added to 1.7 L of H 3 PO 4, followed by stirring at room temperature for 12 hours. When the reaction was terminated, the mixture was neutralized with distilled water and filtered while washing the resulting solid with water. The solid was extracted by dissolving with dichloromethane and neutralized with NaOH. The organic layer was dried over MgSO 4 , the solvent was removed with a rotary evaporator, and recrystallized with hexane to obtain 64 g (87%) of compound 1-3.
화합물 1-4의 제조Preparation of Compound 1-4
화합물 1-3 64 g(0.30 mol), 브로모벤젠(Bromobenzene) 52.8 g(0.33 mol), Pd(OAc)2 1.37 g(6.11 mmol), P(t-Bu)3 50% 7.3 mL(15.28 mmol) 및 NaOt-Bu 58 g(0.61 mol)를 톨루엔 1.2 L에 녹이고, 120 ℃에서 12시간 동안 교반하였다. 반응이 종결되면, 증류수로 중화하고, 에틸아세테이트로 추출하였다. 유기층을 MgSO4로 건조시킨 후 회전 증발기로 용매를 제거하고, 에틸아세테이트를 전개 용매로 하여 컬럼크로마토그래피로 정제하여 화합물 1-4 71 g(81%)를 얻었다. Compound 1-3 64 g (0.30 mol), Bromobenzene 52.8 g (0.33 mol), Pd (OAc) 2 1.37 g (6.11 mmol), P (t-Bu) 3 50% 7.3 mL (15.28 mmol) ) And 58 g (0.61 mol) of NaOt-Bu were dissolved in 1.2 L of toluene and stirred at 120 ° C. for 12 hours. After the reaction was completed, the mixture was neutralized with distilled water and extracted with ethyl acetate. The organic layer was dried over MgSO 4 , and the solvent was removed using a rotary evaporator. The mixture was purified by column chromatography with ethyl acetate as a developing solvent, to obtain 71 g (81%) of Compound 1-4.
화합물 1-5의 제조Preparation of Compound 1-5
화합물 1-4 20 g(0.07 mol)을 DMF 800 mL에 녹이고 0 ℃에서 10분간 교반하였다. 여기에 NBS 12.5 g(0.07 mol)를 DMF 350 mL에 녹인 용액을 천천히 첨가한 후, 0 ℃에서 6시간 동안 교반하였다. 반응이 종결되면, 증류수로 중화하고, 에틸아세테이트로 추출하였다. 유기층을 MgSO4로 건조시킨 후 회전 증발기로 용매를 제거하고, 에틸아세테이트를 전개 용매로하여 컬럼크로마토그래피로 정제하여 화합물 1-5 21 g(84%)를 얻었다. 20 g (0.07 mol) of Compound 1-4 were dissolved in 800 mL of DMF and stirred at 0 ° C. for 10 minutes. A solution of 12.5 g (0.07 mol) of NBS dissolved in 350 mL of DMF was slowly added thereto, followed by stirring at 0 ° C. for 6 hours. After the reaction was completed, the mixture was neutralized with distilled water and extracted with ethyl acetate. The organic layer was dried over MgSO 4 , and the solvent was removed using a rotary evaporator. The mixture was purified by column chromatography with ethyl acetate as a developing solvent, to obtain 21 g (84%) of Compound 1-5.
화합물 1-6의 제조Preparation of Compound 1-6
화합물 1-5 20 g(0.054 mol), 2-클로로아닐린(chloroaniline) 8.4 g(0.065 mol), Pd(OAc)2 370 mg(1.64 mmol), P(t-Bu)3 50% 3.6 mL(5.49 mmol) 및 Cs2CO3 35.7 g(0.109 mol)를 톨루엔 300 mL에 녹이고, 120 ℃에서 4시간 동안 교반하였다. 반응이 종결되면, 증류수로 중화하고, 에틸아세테이트로 추출하였다. 유기층을 MgSO4로 건조시킨 후 회전 증발기로 용매를 제거하고, 에틸아세테이트를 전개 용매로하여 컬럼크로마토그래피로 정제하여 화합물 1-6 13.6 g(60%)를 얻었다. Compound 1-5 20 g (0.054 mol), 2-chloroaniline 8.4 g (0.065 mol), Pd (OAc) 2 370 mg (1.64 mmol), P (t-Bu) 3 50% 3.6 mL (5.49 mmol) and 35.7 g (0.109 mol) of Cs 2 CO 3 were dissolved in 300 mL of toluene and stirred at 120 ° C. for 4 hours. After the reaction was completed, the mixture was neutralized with distilled water and extracted with ethyl acetate. The organic layer was dried over MgSO 4 , and the solvent was removed using a rotary evaporator. Purification by column chromatography using ethyl acetate as a developing solvent gave 13.6 g (60%) of compound 1-6.
화합물 1-7의 제조Preparation of Compound 1-7
화합물 1-6 12.6 g(0.03 mol), Pd(OAc)2 1.37 mg(6.13 mmol), Di-tert-butyl(methyl)phosponium tetrafluoroborate 3 g(12.26 mmol) 및 Cs2CO3 50 g(0.15 mol)를 DMA 240 mL에 녹이고, 190 ℃에서 4시간 동안 교반하였다. 반응이 종결되면, 증류수로 중화하고, 에틸아세테이트로 추출하였다. 유기층을 MgSO4로 건조시킨 후 회전 증발기로 용매를 제거하고, 에틸아세테이트를 전개 용매로하여 컬럼크로마토그래피로 정제하여 화합물 1-7 7 g(70%)를 얻었다.12.6 g (0.03 mol) of Compound 1-6, 1.37 mg (6.13 mmol) of Pd (OAc) 2 , 3 g (12.26 mmol) of Di-tert-butyl (methyl) phosponium tetrafluoroborate and 50 g (0.15 mol) of Cs 2 CO 3 Was dissolved in 240 mL of DMA and stirred at 190 ° C. for 4 h. After the reaction was completed, the mixture was neutralized with distilled water and extracted with ethyl acetate. The organic layer was dried over MgSO 4 , and the solvent was removed using a rotary evaporator. Purification by column chromatography using ethyl acetate as a developing solvent gave 7 g (70%) of compound 1-7.
화합물 1-8의 제조Preparation of Compound 1-8
화합물 1-7 13.2 g(56.12 mmol), Cu 1.7 g(28.06 mmol), K2CO3 7.7 g(56.12 mol) 및 18-crown-6 395 mg(1.49 mmol)를 1,2-다이클로로벤젠(1,2-dichlorobenzene) 200 mL에 녹이고, 180 ℃에서 24시간 동안 환류 교반하였다. 반응이 종결되면 MC로 cellite 여과한 후 회전 증발기로 MC를 제거하고, 증류하여 1,2-다이클로로벤젠(1,2-dichlorobenzene)을 제거하였다. 용매를 제거한 혼합물을 다시 MC에 녹여 물로 중화시키고, MC로 추출하였다. 유기층을 MgSO4로 건조시킨 후 회전 증발기로 용매를 제거하고 에틸아세테이트를 전개 용매로하여 컬럼크로마토그래피로 정제하여 화합물 1-8 8 g(80%)를 얻었다.13.2 g (56.12 mmol) of Compound 1-7, 1.7 g (28.06 mmol) of Cu, 7.7 g (56.12 mol) of K 2 CO 3 , and 395 mg (1.49 mmol) of 18-crown-6 were converted to 1,2-dichlorobenzene ( 1,2-dichlorobenzene) was dissolved in 200 mL and stirred under reflux at 180 ° C. for 24 hours. After the reaction was completed, the cellite was filtered through MC, MC was removed by a rotary evaporator, and distillation was performed to remove 1,2-dichlorobenzene. The mixture from which the solvent was removed was dissolved in MC, neutralized with water, and extracted with MC. The organic layer was dried over MgSO 4 , the solvent was removed using a rotary evaporator, and purified by column chromatography with ethyl acetate as a developing solvent to obtain compound 1-8 8 g (80%).
화합물 1-9의 제조Preparation of Compound 1-9
화합물 1-8 8 g(15.10 mmol)을 THF 250 mL에 녹인 다음 -78 ℃로 냉각시킨 후, n-BuLi(2,5M) 9 mL(22.66 mmol)을 천천히 첨가하였다. 1시간 동안 저온을 유지하며 교반한 후, -78 ℃에서 B(OMe)3 2.5 mL(22.66 mmol)을 첨가하고 1시간 동안 교반하였다. 24시간 동안 반응 후, 0 ℃에서 1M HCl을 첨가하고, 10분 후 증류수로 씻어준 후 에틸아세테이트로 추출하였다. 유기층을 MgSO4로 건조시킨 후 회전 증발기로 용매를 제거하고, 컬럼크로마토그래피로 정제하여 화합물 1-9 5 g(67%)를 얻었다. 8 g (15.10 mmol) of Compound 1-8 were dissolved in 250 mL of THF, cooled to −78 ° C., and 9 mL (22.66 mmol) of n-BuLi (2,5M) was added slowly. After stirring at low temperature for 1 hour, 2.5 mL (22.66 mmol) of B (OMe) 3 was added at -78 ° C and stirred for 1 hour. After the reaction for 24 hours, 1M HCl was added at 0 ° C, washed with distilled water after 10 minutes and extracted with ethyl acetate. The organic layer was dried over MgSO 4 , the solvent was removed with a rotary evaporator, and purified by column chromatography to obtain 5 g (67%) of Compound 1-9.
화합물 1-10의 제조Preparation of Compound 1-10
2,4,6-트라이클로로피리미딘(2,4,6-trichloropyrimidine) 20 g(0.109 mol), 페닐보론산(phenylboronic acid) 29.2 g(0.239 mol), Pd(PPh3)4 6.3 g(0.005 mol), Na2CO3(2M) 163 mL 및 EtOH 163 mL을 톨루엔 320 mL에 첨가한 후 120 ℃에서 가열시켰다. 3시간 동안 교반한 후, 반응이 종결되면 증류수로 씻어주고 에틸아세테이트로 추출하였다. 유기층을 MgSO4로 건조시킨 후 회전 증발기로 용매를 제거하고, 컬럼크로마토그래피로 정제하여 화합물 1-10 25 g(86%)를 얻었다.2,4,6-trichloropyrimidine 20 g (0.109 mol), phenylboronic acid 29.2 g (0.239 mol), Pd (PPh 3 ) 4 6.3 g (0.005 mol), 163 mL Na 2 CO 3 (2M) and 163 mL EtOH were added to 320 mL of toluene and then heated at 120 ° C. After stirring for 3 hours, the reaction was terminated, washed with distilled water and extracted with ethyl acetate. The organic layer was dried over MgSO 4 , the solvent was removed with a rotary evaporator, and purified by column chromatography to obtain 25 g (86%) of Compound 1-10.
화합물 13의 제조Preparation of Compound 13
화합물 1-10 2.7 g(10.11 mmol), 화합물 1-9 5 g(10.11 mmol), Pd(PPh3)4 584 mg(0.50 mmol), K2CO3(2M) 15 mL 및 EtOH 15 mL을 톨루엔 30 mL에 녹이고, 120 ℃에서 가열시켰다. 3시간 동안 교반한 후 반응이 종결되면 증류수로 씻어주고 에틸아세테이트로 추출하였다. 유기층을 MgSO4로 건조시킨 후 회전 증발기로 용매를 제거하고, 컬럼크로마토그래피로 정제하여 화합물 13 5 g(72%)를 얻었다.2.7 g (10.11 mmol) of compound 1-10, 5 g (10.11 mmol) of compound 1-9, 584 mg (0.50 mmol) of Pd (PPh 3 ) 4 , 15 mL of K 2 CO 3 (2M) and 15 mL of EtOH were dissolved in toluene. Dissolved in 30 mL and heated at 120 ° C. After stirring for 3 hours, the reaction was terminated, washed with distilled water and extracted with ethyl acetate. The organic layer was dried over MgSO 4 , the solvent was removed with a rotary evaporator, and purified by column chromatography to obtain 5 g (72%) of compound 13.
[제조예 2] 화합물 48의 제조Preparation Example 2 Preparation of Compound 48
화합물 2-1의 제조Preparation of Compound 2-1
화합물 1-5 22 g(61 mmol), 메틸 2-아미노 벤조에이트(methyl 2-amino benzoate) 20 g(136 mmol), 팔라듐아세테이트(palladium acetate) 0.41 g(1.8 mmol), tri-tert-butyl phosphine 1.69 g(6.1 mmol) 및 세슘카보네이트(cesium carbonate) 39.4 g(120 mmol)을 톨루엔 350 mL에 녹인 후 100 ℃에서 12시간 동안 환류 교반하였다. 반응이 종결되면 H2O/EA로 추출하였다. 유기층을 MgSO4로 건조시킨 후 회전 증발기로 용매를 제거하고, 컬럼으로 분리하여 화합물 2-2 16 g(61%)을 얻었다.22 g (61 mmol) of compound 1-5, 20 g (136 mmol) of methyl 2-amino benzoate, 0.41 g (1.8 mmol) of palladium acetate, tri-tert-butyl phosphine 1.69 g (6.1 mmol) and 39.4 g (120 mmol) of cesium carbonate were dissolved in 350 mL of toluene, followed by stirring under reflux at 100 ° C. for 12 hours. At the end of the reaction, extraction was performed with H 2 O / EA. The organic layer was dried over MgSO 4 , the solvent was removed using a rotary evaporator, and the residue was separated by a column to obtain compound 2-2 16 g (61%).
화합물 2-2의 제조Preparation of Compound 2-2
화합물 2-1 16 g(37 mmol)을 THF 180 mL에 녹인 다음 3M methylmagnesiumbromide 49.1 mL를 첨가하고, 60 ℃에서 4시간 동안 교반하였다. EA/H2O로 추출하고, 유기층을 MgSO4로 건조시킨 후 회전 증발기로 용매를 제거하고, silica 여과하여 화합물 2-2 14 g(87%)을 얻었다. 16 g (37 mmol) of Compound 2-1 was dissolved in 180 mL of THF, and 49.1 mL of 3M methylmagnesium bromide was added thereto, and the mixture was stirred at 60 ° C. for 4 hours. Extraction was performed with EA / H 2 O, the organic layer was dried over MgSO 4 , the solvent was removed with a rotary evaporator, and silica filtration to obtain Compound 2-2 14 g (87%).
화합물 2-3의 제조Preparation of Compound 2-3
화합물 2-2 14 g(32.2 mmol)을 Phosphoric acid 300 mL에 녹인 다음 상온에서 12시간 동안 교반하였다. EA/H2O로 추출하고, 유기층을 MgSO4로 건조시킨 후 회전 증발기로 용매를 제거하고, silica 여과하여 화합물 2-3 10 g(75%)을 얻었다.14 g (32.2 mmol) of Compound 2-2 was dissolved in 300 mL of phosphoric acid, and then stirred at room temperature for 12 hours. Extraction was performed with EA / H 2 O, the organic layer was dried with MgSO 4 , the solvent was removed with a rotary evaporator, and filtered through silica to obtain compound 2-3 (10 g, 75%).
화합물 2-4의 제조Preparation of Compound 2-4
화합물 2-3 10 g(24 mmol), 4-브로모아이오도벤젠(4-bromoiodobenzene) 20.37 g(72 mmol), copper powder 3.05 g(48 mmol), 18-crown-6 1.52 g(5.8mmol) 및 potassium carbonate 9.95 g(72 mmol)을 1,2-다이클로로벤젠(1,2-dichlorobenzene) 200 mL에 녹인 다음 180 ℃에서 12시간 동안 환류 교반하였다. 1,2-다이클로로벤젠(1,2-dichlorobenzene)은 증류하여 제거한 후, EA/H2O로 추출하였다. 유기층을 MgSO4로 건조시킨 후 회전 증발기로 용매를 제거하고, 컬럼으로 분리하여 화합물 2-4 6.5 g(47%)을 얻었다.Compound 2-3 10 g (24 mmol), 4-bromoiodobenzene 20.37 g (72 mmol), copper powder 3.05 g (48 mmol), 18-crown-6 1.52 g (5.8 mmol) and 9.95 g (72 mmol) of potassium carbonate was dissolved in 200 mL of 1,2-dichlorobenzene and stirred under reflux at 180 ° C. for 12 hours. 1,2-dichlorobenzene (1,2-dichlorobenzene) was distilled off and extracted with EA / H 2 O. The organic layer was dried over MgSO 4 , the solvent was removed with a rotary evaporator, and the mixture was separated by a column to obtain 6.5 g (47%) of Compound 2-4.
화합물 2-5의 제조Preparation of Compound 2-5
화합물 2-4 6.5 g(11 mmol)을 THF 100 mL에 녹인 다음 -78 ℃에서 2.5M n-Butyl lithium 5.91 mL를 가하여 1시간 동안 교반한 후, tri-isopropyl borate 4.45 mL(19 mmol)를 가하여 12시간 동안 교반하였다. EA/H2O 추출하고, 유기층을 MgSO4로 건조시킨 후 회전 증발기로 용매를 제거하고, dichloromethane/methanol로 재결정하여 화합물 2-5 3 g(41%)을 얻었다.6.5 g (11 mmol) of Compound 2-4 were dissolved in 100 mL of THF, and 5.91 mL of 2.5M n-Butyl lithium was added at -78 ° C, stirred for 1 hour, and then 4.45 mL (19 mmol) of tri-isopropyl borate was added thereto. Stir for 12 hours. EA / H 2 O extraction, the organic layer was dried over MgSO 4 and the solvent was removed by a rotary evaporator, and recrystallized with dichloromethane / methanol to give compound 2-5 3 g (41%).
화합물 2-6의 제조Preparation of Compound 2-6
2,4-다이클로로피리미딘(2,4-dichloropyrimidine) 15 g(100 mmol), 페닐보론산(phenyl boronic acid) 12.28 g(100 mL), Tetrakis(triphenylphosphine)palladium 5.82 g(5 mmol), sodium carbonate 25.61 g(240 mmol) 및 에탄올 200 mL을 톨루엔 500 mL에 녹인 다음 70 ℃에서 3시간 동안 환류 교반하였다. EA/H2O로 추출하고, 유기층을 MgSO4로 건조시킨 후 회전 증발기로 용매를 제거하고, 컬럼으로 분리하여 화합물 2-6 16 g(83%)을 얻었다.15 g (100 mmol) of 2,4-dichloropyrimidine, 12.28 g (100 mL) of phenyl boronic acid, 5.82 g (5 mmol) of tetrakis (triphenylphosphine) palladium, sodium 25.61 g (240 mmol) of carbonate and 200 mL of ethanol were dissolved in 500 mL of toluene and stirred at reflux at 70 ° C. for 3 hours. The mixture was extracted with EA / H 2 O, the organic layer was dried over MgSO 4 , the solvent was removed with a rotary evaporator, and separated by a column to obtain 16 g (83%) of Compound 2-6.
화합물 48의 제조Preparation of Compound 48
화합물 2-6 0.75 g(3.9 mmol), 화합물 2-5 2.53 g(4.7mmol), Tetrakis(triphenylphosphine)palladium 0.23 g(0.2 mmol), potassium carbonate 1.31 g(9.4 mmol) 및 에탄올 50 mL을 톨루엔 150 mL에 녹인 다음 120 ℃에서 5시간 동안 환류 교반하였다. EA/H2O로 추출하고, 유기층을 MgSO4로 건조시킨 후 회전 증발기로 용매를 제거하고, 컬럼으로 분리하여 화합물 48 0.76 g(30%)을 얻었다.
0.75 g (3.9 mmol) of Compound 2-6, 2.53 g (4.7 mmol) of Compound 2-5, 0.23 g (0.2 mmol) of Tetrakis (triphenylphosphine) palladium, 1.31 g (9.4 mmol) of potassium carbonate and 50 mL of ethanol 150 mL It was dissolved in and stirred under reflux at 120 ° C. for 5 hours. Extraction was performed with EA / H 2 O, the organic layer was dried over MgSO 4 , the solvent was removed with a rotary evaporator, and separated by a column to obtain compound 48 0.76 g (30%).
상기 제조예 1 및 제조예 2의 방법을 이용하여 유기 발광 화합물 1 내지 화합물 60을 제조하였으며, 표 1에 제조된 유기 발광 화합물들의 1H NMR 및 MS/FAB를 나타내었다.The organic light emitting compounds 1 to compound 60 were manufactured by using the methods of Preparation Example 1 and Preparation Example 2, and the 1 H NMR and the MS / FAB of the organic light emitting compounds prepared in Table 1 are shown.
[표 1]TABLE 1
[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(15 Ω/□)을, 트리클로로에틸렌, 아세톤, 에탄올, 증류수를 순차적으로 사용하여 초음파 세척을 실시한 후, 이소프로판올에 넣어 보관한 후 사용하였다. 다음으로, 진공 증착 장비의 기판 폴더에 ITO 기판을 설치하고, 진공 증착 장비 내의 셀에 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA)을 넣고, 챔버 내의 진공도가 10-6 torr에 도달할 때까지 배기시킨 후, 셀에 전류를 인가하여 2-TNATA를 증발시켜 ITO 기판 상에 60 nm 두께의 정공주입층을 증착하였다. 이어서, 진공 증착 장비 내의 다른 셀에 N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB)을 넣고, 셀에 전류를 인가하여 NPB를 증발시켜 정공주입층 위에 20 nm 두께의 정공전달층을 증착하였다. 정공주입층, 정공전달층을 형성시킨 후, 그 위에 발광층을 다음과 같이 증착시켰다. 진공 증착 장비 내의 한쪽 셀에 호스트로서 본 발명에 따른 화합물 20을 넣고, 또 다른 셀에는 도판트로서 Ir(ppy)3[tris(2-phenylpyridine)iridium]를 각각 넣은 후, 두 물질을 다른 속도로 증발시켜 4 내지 10%중량으로 도핑함으로써 상기 정공 전달층 위에 30 nm 두께의 발광층을 증착하였다. 이어서 상기 발광층 위에 전자전달층으로써 tris(8-hydroxyquinoline)-aluminum(III) (Alq)를 20 nm 두께로 증착한 다음, 전자주입층으로 lithium quinolate (Liq)를 1 내지 2 nm 두께로 증착한 후, 다른 진공 증착 장비를 이용하여 Al 음극을 150 nm의 두께로 증착하여 OLED소자를 제작하였다. 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? It was used after. Next, the ITO substrate is installed in the substrate folder of the vacuum deposition apparatus, and 4,4 ', 4 "-tris (N, N- (2-naphthyl) -phenylamino) triphenylamine (2-TNATA) is installed in the cell in the vacuum deposition apparatus. And evacuated until the vacuum in the chamber reached 10 −6 torr, followed by applying a current to the cell to evaporate 2-TNATA to deposit a 60 nm thick hole injection layer on the ITO substrate. N, N '-bis (α- naphthyl) - N, N' to another cell of the vapor deposition devices placed -diphenyl-4,4'-diamine (NPB) , and evaporation of the NPB by applying a current to the cell, the hole injection layer A 20 nm thick hole transport layer was deposited on top of the hole injection layer and the hole transport layer was then deposited on the light emitting layer as follows: Compound 20 according to the invention as a host in one cell in a vacuum deposition apparatus; In another cell, add Ir (ppy) 3 [tris (2-phenylpyridine) iridium] as a dopant, respectively, and add the two substances at different rates. A light emitting layer of 30 nm thickness was deposited on the hole transport layer by flashing and doping to 4 to 10% by weight, followed by 20 nm thickness of tris (8-hydroxyquinoline) -aluminum (III) (Alq) as an electron transporting layer on the light emitting layer. After depositing, the lithium quinolate (Liq) was deposited with an electron injection layer to a thickness of 1 to 2 nm, and an Al cathode was deposited to a thickness of 150 nm using another vacuum deposition equipment to manufacture an OLED device.
재료 별로 각 화합물은 10-6 torr 하에서 진공 승화 정제하여 OLED 발광재료로 사용하였다.Each compound was vacuum sublimated and purified under 10 -6 torr to be used as an OLED light emitting material.
그 결과, 6.6 V의 전압에서 3.5 mA/cm2의 전류가 흘렀으며, 1270 cd/m2의 녹색발광이 확인되었다.As a result, a current of 3.5 mA / cm 2 flowed at a voltage of 6.6 V, and green light emission of 1270 cd / m 2 was confirmed.
[실시예 2] [Example 2]
발광층에서 호스트 재료로서 화합물 30을 넣고, 발광 도판트로서 Ir(ppy)3[tris(2-phenylpyridine)iridium]을 이용한 것 외에는, 실시예 1과 동일한 방법으로 OLED소자를 제작하였다.An OLED device was manufactured in the same manner as in Example 1, except that Compound 30 was added as a host material in the light emitting layer and Ir (ppy) 3 [tris (2-phenylpyridine) iridium] was used as the light emitting dopant.
그 결과, 7.2 V의 전압에서 3.7 mA/cm2의 전류가 흘렀으며, 1040 cd/m2의 녹색발광이 확인되었다.As a result, a current of 3.7 mA / cm 2 flowed at a voltage of 7.2 V, and green light emission of 1040 cd / m 2 was confirmed.
[실시예 3] Example 3
발광층에서 호스트 재료로서 화합물 40을 넣고, 발광 도판트로서 Ir(ppy)3[tris(2-phenylpyridine)iridium]을 이용한 것 외에는, 실시예 1과 동일한 방법으로 OLED소자를 제작하였다.An OLED device was manufactured in the same manner as in Example 1, except that Compound 40 was added as a host material in the light emitting layer and Ir (ppy) 3 [tris (2-phenylpyridine) iridium] was used as the light emitting dopant.
그 결과, 6.7 V의 전압에서 3.7 mA/cm2의 전류가 흘렀으며, 1170 cd/m2의 녹색발광이 확인되었다.As a result, a current of 3.7 mA / cm 2 flowed at a voltage of 6.7 V, and green light emission of 1170 cd / m 2 was confirmed.
[실시예 4] Example 4
발광층에서 호스트 재료로서 화합물 48을 넣고, 발광 도판트로서 Ir(ppy)3[tris(2-phenylpyridine)iridium]을 이용한 것 외에는, 실시예 1과 동일한 방법으로 OLED소자를 제작하였다.An OLED device was manufactured in the same manner as in Example 1, except that Compound 48 was added as a host material in the light emitting layer and Ir (ppy) 3 [tris (2-phenylpyridine) iridium] was used as the light emitting dopant.
그 결과, 6.9 V의 전압에서 4.1 mA/cm2의 전류가 흘렀으며, 1120 cd/m2의 녹색발광이 확인되었다.As a result, a current of 4.1 mA / cm 2 flowed at a voltage of 6.9 V, and green light emission of 1120 cd / m 2 was confirmed.
[비교예 1] Comparative Example 1
진공 증착 장비 내의 한쪽 셀에 호스트 재료로서 본 발명의 화합물 대신 4,4'-bis(carbazol-9-yl)biphenyl(CBP), 도판트로서 Ir(ppy)3[tris(2-phenyl pyridine)iridium]을 이용하고, 정공차단층으로 비스(2-메틸-8-퀴놀리네이토)(p-페닐페놀레이토)알루미늄(III) (BAlq)를 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 OLED소자를 제작하였다.4,4'-bis (carbazol-9-yl) biphenyl (CBP) as a host material in one cell in a vacuum deposition apparatus, Ir (ppy) 3 [tris (2-phenyl pyridine) iridium as dopant OLED was used in the same manner as in Example 1, except that bis (2-methyl-8-quinolinate) ( p -phenylphenolrato) aluminum (III) (BAlq) was used as the hole blocking layer. The device was produced.
그 결과, 7.5 V의 전압에서 3.8 mA/cm2의 전류가 흘렀으며, 1000 cd/m2의 녹색발광이 확인되었다.
As a result, a current of 3.8 mA / cm 2 flowed at a voltage of 7.5 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,
A고리는 또는 이고;
X는 -C(R12)(R13)-, -N(R14)-, -S-, -O- 또는 -Si(R15)(R16)-이며;
Ar1 및 Ar2는 서로 독립적으로 치환 또는 비치환된(C6-C30)아릴렌 또는 치환 또는 비치환된(C3-C30)헤테로아릴렌이고; Ar3 내지 Ar5는 서로 독립적으로 치환 또는 비치환된(C6-C30)아릴 또는 치환 또는 비치환된(C3-C30)헤테로아릴이며;
R1 내지 R16은 서로 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C3-C30)시클로알킬이 하나 이상 융합된 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C3-C30)헤테로아릴, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된(C3-C30)시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 (C3-C30)시클로알킬, 시아노, 나이트로, NR21R22, BR23R24, PR25R26, P(=O)R27R28, R29R30R31Si-, R32Y-, 치환 또는 비치환된(C6-C30)아르(C1-C30)알킬, 치환 또는 비치환된(C2-C30)알케닐, 치환 또는 비치환된(C2-C30)알키닐, , , 이거나, 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리, 단일환 또는 다환의 헤테로방향족고리를 형성할 수 있고; 상기 B고리 및 C고리는 서로 독립적으로 치환 또는 비치환된(C5-C30)사이클로알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C6-C30)헤테로아릴이며; 상기 R21 내지 R32는 서로 독립적으로 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 치환 또는 비치환된(C3-C30)헤테로아릴이고; 상기 Y는 S 또는 O이며; W는 -(CR51R52)m-, -(R51)C=C(R52)-, -N(R53)-, -S-, -O-, -Si(R54)(R55)-, -P(R56)-, -P(=O)(R57)-, -C(=O)- 또는 -B(R58)-이고, R41 내지 R43 및 R51 내지 R58은 상기 R1 내지 R16에서의 정의와 동일하며; 상기 헤테로시클로알킬, 헤테로아릴 및 헤테로방향족고리는 B, N, O, S, P(=O), Si 및 P로부터 선택된 하나 이상의 헤테로원자를 포함하고; m은 0 내지 2의 정수이며; a, b는 0 내지 4의 정수이고; a, b가 2 이상일 경우에는 서로 동일하거나 상이할 수 있다.]An organic light emitting compound represented by Formula 1 below.
[Formula 1]
[In the above formula (1)
A ring or ego;
X is -C (R 12 ) (R 13 )-, -N (R 14 )-, -S-, -O- or -Si (R 15 ) (R 16 )-;
Ar 1 and Ar 2 are each independently substituted or unsubstituted (C6-C30) arylene or substituted or unsubstituted (C3-C30) heteroarylene; Ar 3 to Ar 5 are each independently substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl;
R 1 to R 16 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) cyclo Substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted, with one or more alkyl fused To 7-membered heterocycloalkyl fused with one or more aromatic rings, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted aromatic rings with one or more fused (C3-C30) cycloalkyl , Cyano, nitro, NR 21 R 22 , BR 23 R 24 , PR 25 R 26 , P (= O) R 27 R 28 , R 29 R 30 R 31 Si-, R 32 Y-, substituted or unsubstituted Substituted (C6-C30) ar (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl, , , Or an alicyclic ring and a monocyclic or polycyclic aromatic ring, monocyclic or polycyclic heteroaromatic linked with (C3-C30) alkylene or (C3-C30) alkenylene with or without adjacent substituents and fused rings May form a ring; Ring B and ring C are independently substituted or unsubstituted (C5-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C6-C30) heteroaryl; R 21 to R 32 are each independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl; Y is S or O; W is-(CR 51 R 52 ) m -,-(R 51 ) C = C (R 52 )-, -N (R 53 )-, -S-, -O-, -Si (R 54 ) (R 55 )-, -P (R 56 )-, -P (= 0) (R 57 )-, -C (= 0)-or -B (R 58 )-, and R 41 to R 43 and R 51 to R 58 is the same as defined above for R 1 to R 16 ; The heterocycloalkyl, heteroaryl and heteroaromatic ring comprises one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P; m is an integer from 0 to 2; a, b are integers from 0 to 4; When a and b are 2 or more, they may be the same as or different from each other.]
상기 는 하기 구조에서 선택되는 것을 특징으로 하는 유기 발광 화합물.
[R1 내지 R10 및 R12 내지 R16은 서로 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C3-C30)헤테로아릴, NR21R22, BR23R24, PR25R26, P(=O)R27R28, R29R30R31Si- 또는 R32Y-이거나, 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리, 단일환 또는 다환의 헤테로방향족고리를 형성할 수 있으며; 상기 R21 내지 R32는 서로 독립적으로 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 치환 또는 비치환된(C3-C30)헤테로아릴이고; 상기 Y는 S 또는 O이며; 상기 헤테로아릴 및 헤테로방향족고리는 B, N, O, S, P(=O), Si 및 P로부터 선택된 하나 이상의 헤테로원자를 포함한다.]The method of claim 1,
remind Is an organic light emitting compound, characterized in that selected from the following structure.
[R 1 to R 10 And R 12 to R 16 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) Heteroaryl, NR 21 R 22 , BR 23 R 24 , PR 25 R 26 , P (= O) R 27 R 28 , R 29 R 30 R 31 Si- or R 32 Y- or include a fused ring with adjacent substituents May be linked with (C3-C30) alkylene or (C3-C30) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, a monocyclic or polycyclic heteroaromatic ring; R 21 to R 32 are each independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl; Y is S or O; Wherein said heteroaryl and heteroaromatic rings comprise one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P.]
상기 Ar1 내지 Ar5, R1 내지 R16, R21 내지 R32, R41 내지 R43, R51 내지 R58에 더 치환되는 치환기는 서로 독립적으로 중수소, 할로겐, 할로겐이 치환 또는 비치환된(C1-C30)알킬, (C6-C30)아릴, (C6-C30)아릴이 치환 또는 비치환된(C3-C30)헤테로아릴, (C3-C30)헤테로아릴, 5원 내지 7원의 헤테로시클로알킬, 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬, (C3-C30)시클로알킬, 방향족고리가 하나이상 융합된 (C3-C30)시클로알킬, NR61R62, BR63R64, PR65R66, P(=O)R67R68, R69R70R71Si-, R72Z-, R73C(=O)-, R74C(=O)O-, (C2-C30)알케닐, (C2-C30)알키닐, 시아노, 카바졸릴, (C6-C30)아르(C1-C30)알킬, (C1-C30)알킬(C6-C30)아릴, 카르복실, 나이트로 또는 하이드록시로 이루어진 군으로부터 선택되는 하나 이상으로 더 치환되거나, 서로 인접한 치환체가 연결되어 고리를 형성할 수 있고; 상기 R61 내지 R72는 서로 독립적으로 (C1-C30)알킬, (C6-C30)아릴 또는 (C3-C30)헤테로아릴이며; 상기 Z는 S 또는 O이고; 상기 R73 및 R74는 서로 독립적으로 (C1-C30)알킬, (C1-C30)알콕시, (C6-C30)아릴 또는 (C6-C30)아릴옥시인 것을 특징으로 하는 유기 발광 화합물.The method of claim 1,
Substituents further substituted with Ar 1 to Ar 5 , R 1 to R 16 , R 21 to R 32 , R 41 to R 43 , and R 51 to R 58 may be each independently substituted or unsubstituted with deuterium, halogen, or halogen. (C1-C30) alkyl, (C6-C30) aryl, (C6-C30) aryl substituted or unsubstituted (C3-C30) heteroaryl, (C3-C30) heteroaryl, 5- to 7-membered heterocyclo Alkyl, 5- to 7-membered heterocycloalkyl fused at least one aromatic ring, (C3-C30) cycloalkyl, (C3-C30) cycloalkyl fused at least one aromatic ring, NR 61 R 62 , BR 63 R 64 , PR 65 R 66 , P (= O) R 67 R 68 , R 69 R 70 R 71 Si-, R 72 Z-, R 73 C (= O)-, R 74 C (= O) O-, (C2-C30) alkenyl, (C2-C30) alkynyl, cyano, carbazolyl, (C6-C30) ar (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, carboxyl Further substituted with one or more selected from the group consisting of nitro or hydroxy, or substituents adjacent to each other are connected to form a ring It can have; R 61 to R 72 independently of one another are (C1-C30) alkyl, (C6-C30) aryl or (C3-C30) heteroaryl; Z is S or O; R 73 and R 74 are independently from each other (C1-C30) alkyl, (C1-C30) alkoxy, (C6-C30) aryl or (C6-C30) aryloxy.
상기 는 하기 구조에서 선택되는 것을 특징으로 하는 유기 발광 화합물.
[R81 내지 R109는 서로 독립적으로 수소, (C6-C30)아릴, (C3-C30)헤테로아릴 또는 트리(C6-C30)아릴실릴이다.]The method of claim 1,
remind Is an organic light emitting compound, characterized in that selected from the following structure.
[R 81 To R 109 are independently of each other hydrogen, (C6-C30) aryl, (C3-C30) heteroaryl or tri (C6-C30) arylsilyl.]
상기 R1 내지 R16은 서로 독립적으로 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, 플루오르, 시아노, 메톡시, 에톡시, n-프로폭시, i-프로폭시, n-부톡시, i-부톡시, t-부톡시, n-펜톡시, i-펜톡시, n-헥실옥시, n-헵톡시, 시클로프로필, 시클로부틸, 시클로펜틸, 시클로헥실, 시클로헵틸, 시클로옥틸, 시클로노닐, 시클로데실, 트리플루오르메틸, 퍼플루오르에틸, 트리플루오르에틸, 퍼플루오르프로필, 퍼플루오르부틸, 페닐, 나프틸, 비페닐, 플루오레닐, 페난트릴, 안트릴, 플루오란텐일, 트리페닐렌일, 피렌일, 크라이세닐, 나프타세닐, 페릴렌일, 피리딜, 피롤릴, 퓨란일, 티오펜일, 이미다졸릴, 벤조이미다졸릴, 피라진일, 피리미딘일, 피리다진일, 퀴놀릴, 트리아진일, 디페닐트리아진일, 페노티아진일, 벤조퓨란일, 벤조티오펜일, 디벤조퓨란일, 디벤조티오페닐, 피라졸릴, 인돌릴, N-페닐피리도인돌릴, N-페닐피라지노인돌릴, 카바졸릴, N-페닐카바졸릴, N-페닐벤조카바졸릴, 티아졸릴, 옥사졸릴, 벤조티아졸릴, 벤조옥사졸릴, 트리메틸실릴, 트리에틸실릴, 트리프로필실릴, 트리(t-부틸)실릴, t-부틸디메틸실릴, 디메틸페닐실릴, 트리페닐실릴 또는 벤질인 것을 특징으로 하는 유기 발광 화합물. The method of claim 1,
R 1 to R 16 are each independently 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, fluorine, cyano, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i -Butoxy, t-butoxy, n-pentoxy, i-pentoxy, n-hexyloxy, n-heptoxy, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl , Cyclodecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, naphthyl, biphenyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, Pyrenyl, chrysenyl, naphthacenyl, peryleneyl, pyridyl, pyrrolyl, furanyl, thiophenyl, imidazolyl, benzoimidazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, tri Genyl, diphenyltriazinyl, phenothiazineyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyrazolyl, indolyl, N-phenylpyridoindolyl, N-phenylpyrazinoin Doryl, carbazolyl, N-phenylcarbazolyl, N-phenylbenzocarbazolyl, thiazolyl, oxazolyl, benzothiazolyl, benzooxazolyl, trimethylsilyl, triethylsilyl, tripropylsilyl, tri (t-butyl) silyl and t-butyldimethylsilyl, dimethylphenylsilyl, triphenylsilyl or benzyl.
상기 유기 전계 발광 소자는 제1전극; 제2전극; 및 상기 제1전극과 제2전극 사이에 개재되는 1층 이상의 유기물층으로 이루어져 있으며, 상기 유기물층은 상기 유기 발광 화합물 하나 이상과 하기 화학식 2로 표시되는 도판트 하나 이상을 포함하는 것을 특징으로 하는 유기 전계 발광 소자.
[화학식 2]
M1L101L102L103
[상기 화학식 2에서,
M1은 7족, 8족, 9족, 10족, 11족, 13족, 14족, 15족 및 16족의 금속으로 이루어진 군으로부터 선택되고, 리간드 L101, L102 및 L103 는 서로 독립적으로 하기 구조로부터 선택되며;
R201 내지 R203은 서로 독립적으로 수소, 할로겐이 치환되거나 치환되지 않은 (C1-C30)알킬, (C1-C30)알킬이 치환되거나 치환되지 않은 (C6-C30)아릴 또는 할로겐이고; R204 내지 R219는 서로 독립적으로 수소, 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 R223은 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 R229는 서로 독립적으로 수소, 중수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 할로겐이고;
Q는 , 또는 이며, R231 내지 R242는 서로 독립적으로 수소, 중수소, 할로겐이 치환되거나 치환되지 않은 (C1-C30)알킬, (C1-C30)알콕시, 할로겐, 치환 또는 비치환된(C6-C30)아릴, 시아노, 치환 또는 비치환된(C5-C30)시클로알킬이거나, 인접한 치환체와 알킬렌 또는 알케닐렌으로 연결되어 스피로 고리 또는 융합고리를 형성할 수 있거나, R207 또는 R208과 알킬렌 또는 알케닐렌으로 연결되어 포화 또는 불포화의 융합고리를 형성할 수 있다.]The method of claim 6,
The organic electroluminescent device includes a first electrode; A second electrode; And one or more organic material layers interposed between the first electrode and the second electrode, wherein the organic material layer includes one or more organic light emitting compounds and one or more dopants represented by the following Chemical Formula 2. Light emitting element.
(2)
M 1 L 101 L 102 L 103
[In Formula 2,
M 1 is selected from the group consisting of metals of Groups 7, 8, 9, 10, 11, 13, 14, 15 and 16, and ligands L 101 , L 102 and L 103. Are independently selected from the following structures;
R 201 to R 203 are independently of each other hydrogen, (C1-C30) alkyl with or without halogen, (C6-C30) aryl or halogen with or without (C1-C30) alkyl; R 204 to R 219 are each independently hydrogen, 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 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 , or R 231 to R 242 are each independently of the other hydrogen, deuterium, (C1-C30) alkyl, (C1-C30) alkoxy, halogen, substituted or unsubstituted (C6-C30) aryl, Cyano, substituted or unsubstituted (C5-C30) cycloalkyl, or may be linked to adjacent substituents with alkylene or alkenylene to form a spiro ring or fused ring, or with R 207 or R 208 and alkylene or alkenylene To form a saturated or unsaturated fused ring.]
상기 유기물층에 아릴아민계 화합물 또는 스티릴아릴아민계 화합물로 이루어진 군으로부터 선택된 하나 이상의 아민계 화합물 또는 1족, 2족, 4주기, 5주기 전이금속, 란탄계열금속 및 d-전이원소의 유기금속으로 이루어진 군으로부터 선택되는 하나 이상의 금속을 더 포함하는 것을 특징으로 하는 유기 전계 발광 소자.The method of claim 7, wherein
At least one amine compound selected from the group consisting of an arylamine compound or a styrylarylamine compound or an organic metal of Group 1, Group 2, 4 cycle, 5 cycle transition metal, lanthanide series metal and d-transition element in the organic layer The organic electroluminescent device further comprises at least one metal selected from the group consisting of.
상기 유기물층은 발광층 및 전하생성층을 포함하는 것을 특징으로 하는 유기 전계 발광 소자.The method of claim 7, wherein
The organic material layer is an organic electroluminescent device comprising a light emitting layer and a charge generating layer.
상기 유기물층에 청색, 적색 또는 녹색 발광을 하는 유기발광층 하나 이상을 더 포함하여 백색 발광을 하는 것을 특징으로 하는 유기 전계 발광 소자.
The method of claim 7, wherein
The organic light emitting device of claim 1, further comprising at least one organic light emitting layer for emitting blue, red or green light to the organic material layer.
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DK68593D0 (en) * | 1993-06-11 | 1993-06-11 | Nkt Res Center As | ELECTROACTIVE MATERIALS, PROCEDURES FOR THEIR MANUFACTURING AND USE THEREOF |
JP4792687B2 (en) * | 2000-07-07 | 2011-10-12 | Jnc株式会社 | Charge transport material, light-emitting material containing diazapentacene derivative, and organic electroluminescent device using the same |
KR100827918B1 (en) * | 2005-11-30 | 2008-05-07 | 주식회사 엘지화학 | Quinacridine derivatives and organic electronic devices using the same |
KR100970713B1 (en) * | 2007-12-31 | 2010-07-16 | 다우어드밴스드디스플레이머티리얼 유한회사 | Electroluminescent device Green using the electroluminescent compounds |
DE102009023155A1 (en) * | 2009-05-29 | 2010-12-02 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
-
2010
- 2010-01-28 KR KR1020100007866A patent/KR20110088118A/en not_active Application Discontinuation
-
2011
- 2011-01-17 WO PCT/KR2011/000333 patent/WO2011093609A1/en active Application Filing
- 2011-01-28 TW TW100103273A patent/TW201139609A/en unknown
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US10790452B2 (en) | 2014-06-10 | 2020-09-29 | Samsung Display Co., Ltd. | Antiaromatic compounds and organic light-emitting devices comprising the same |
US10084141B2 (en) | 2014-06-13 | 2018-09-25 | Samsung Display Co., Ltd. | Antiaromatic compound and organic light-emitting device including the same |
US10249829B2 (en) | 2015-11-24 | 2019-04-02 | Samsung Display Co., Ltd. | Compound and organic light-emitting device including the same |
KR20170061771A (en) * | 2015-11-26 | 2017-06-07 | 삼성디스플레이 주식회사 | Condensed cyclic compound and organic light emitting device comprising the same |
US10367152B2 (en) | 2015-11-26 | 2019-07-30 | Samsung Display Co., Ltd. | Condensed cyclic compound and organic light-emitting device including the same |
US10074812B2 (en) | 2016-03-18 | 2018-09-11 | Samsung Display Co., Ltd. | Compound and organic light-emitting device including the same |
KR20180012901A (en) * | 2016-07-27 | 2018-02-07 | 삼성디스플레이 주식회사 | Polycyclic compound and organic light emitting device comprising the same |
US10205104B2 (en) | 2016-07-27 | 2019-02-12 | Samsung Display Co., Ltd. | Polycyclic compound and organic light-emitting device including the same |
Also Published As
Publication number | Publication date |
---|---|
WO2011093609A1 (en) | 2011-08-04 |
TW201139609A (en) | 2011-11-16 |
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