WO2015053463A1 - Compound, organic optoelectric diode including same, and display device - Google Patents
Compound, organic optoelectric diode including same, and display device Download PDFInfo
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- WO2015053463A1 WO2015053463A1 PCT/KR2014/006116 KR2014006116W WO2015053463A1 WO 2015053463 A1 WO2015053463 A1 WO 2015053463A1 KR 2014006116 W KR2014006116 W KR 2014006116W WO 2015053463 A1 WO2015053463 A1 WO 2015053463A1
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 69
- 239000010410 layer Substances 0.000 claims description 60
- 239000012044 organic layer Substances 0.000 claims description 25
- 230000005693 optoelectronics Effects 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 13
- 239000002019 doping agent Substances 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- -1 sulfamoylamino group Chemical group 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
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- SYQQWGGBOQFINV-FBWHQHKGSA-N 4-[2-[(2s,8s,9s,10r,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-2-yl]ethoxy]-4-oxobutanoic acid Chemical compound C1CC2=CC(=O)[C@H](CCOC(=O)CCC(O)=O)C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 SYQQWGGBOQFINV-FBWHQHKGSA-N 0.000 description 1
- LTUJKAYZIMMJEP-UHFFFAOYSA-N 9-[4-(4-carbazol-9-yl-2-methylphenyl)-3-methylphenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C(=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C)C(C)=C1 LTUJKAYZIMMJEP-UHFFFAOYSA-N 0.000 description 1
- 229910016036 BaF 2 Inorganic materials 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- ZNKKYYNWFKHNHZ-UHFFFAOYSA-N CC1C=CC=CC1 Chemical compound CC1C=CC=CC1 ZNKKYYNWFKHNHZ-UHFFFAOYSA-N 0.000 description 1
- RODXDSBYCAYUCI-UHFFFAOYSA-N CCc1c(C)c(nccc2)c2[s]1 Chemical compound CCc1c(C)c(nccc2)c2[s]1 RODXDSBYCAYUCI-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241000238558 Eucarida Species 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000207961 Sesamum Species 0.000 description 1
- 235000003434 Sesamum indicum Nutrition 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000005137 deposition process Methods 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 150000002504 iridium compounds Chemical class 0.000 description 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- RJQVQDYEBIHZKH-UHFFFAOYSA-N methyl 2-chloro-4-methylpyridine-3-carboxylate Chemical compound COC(=O)C1=C(C)C=CN=C1Cl RJQVQDYEBIHZKH-UHFFFAOYSA-N 0.000 description 1
- FOKUGIKLNXFRTI-UHFFFAOYSA-N methyl 2-chloro-5-methylpyridine-3-carboxylate Chemical compound COC(=O)C1=CC(C)=CN=C1Cl FOKUGIKLNXFRTI-UHFFFAOYSA-N 0.000 description 1
- MYGAJZBZLONIBZ-UHFFFAOYSA-N methyl 2-chloropyridine-3-carboxylate Chemical compound COC(=O)C1=CC=CN=C1Cl MYGAJZBZLONIBZ-UHFFFAOYSA-N 0.000 description 1
- MOMQDEDQGJAKII-UHFFFAOYSA-N methyl 5-bromo-2-chloropyridine-3-carboxylate Chemical compound COC(=O)C1=CC(Br)=CN=C1Cl MOMQDEDQGJAKII-UHFFFAOYSA-N 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 239000007774 positive electrode material Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000001846 repelling effect Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/30—Devices specially adapted for multicolour light emission
- H10K59/32—Stacked devices having two or more layers, each emitting at different wavelengths
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
Definitions
- a compound, an organic optoelectronic device, and a display device are provided.
- An organic optoelectric diode is a device capable of converting electrical energy and optical energy.
- Organic optoelectronic devices can be divided into two types according to the principle of operation.
- One of the axial tone (exciton) formed by the light energy is separated into electrons and holes, and a photoelectric device in which the electrons and holes generates electric energy as each "Route to each other electrode, and the other is a voltage or current to the electrode
- It is a light emitting device that supplies and generates light energy from electrical energy.
- Examples of the organic optoelectronic device include an organic photoelectric device, an organic light emitting device, an organic solar cell, and an organic photo conductor drum.
- the organic light emitting device converts electrical energy into light by applying an electric current to the organic light emitting material.
- the organic light emitting device has a structure in which an organic layer is inserted between an anode and a cathode.
- the organic layer may include a light emitting layer and an auxiliary layer, and the auxiliary layer may include, for example, a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer, an electron injection layer, and the like, to increase the efficiency and stability of the organic light emitting device. It may comprise at least one layer selected from the hole blocking layer.
- the performance of the organic light emitting device is greatly influenced by the characteristics of the organic layer, and in particular, by the organic materials included in the organic layer.
- An organic light emitting device including the compound and a display device including the organic light emitting device are provided.
- R 1 to R 6 are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted silyl group,
- R 1 to R 3 is substituted or unsubstituted C6 to C30
- R 4 to R 6 is a substituted or unsubstituted C1 to C4 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted silyl group,
- X 1 and X 2 are each independently 0, S, SO, S0 2 , POR 7 , NR 8 , CR 9 R 10 , or
- R 7 to R 12 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted C3 to C30 heterocycloalkyl group, substituted or Unsubstituted C6 to C30 aryl group, substituted or unsubstituted C2 to C30 heteroaryl group, substituted or unsubstituted amine group substituted or unsubstituted C6 to C30 arylamine group, substituted or unsubstituted C6 to C30 hetero Arylamine group, substituted or unsubstituted C 1 to C30 alkoxy group, substituted or unsubstituted C2 to C30 alkoxycarbonyl group, substituted or unsubstituted C2 to C30
- Aryloxycarbonylamino group substituted or unsubstituted C1 to C30 sulfamoylamino group, substituted or unsubstituted C2 to C30 alkenyl group, substituted or unsubstituted C2 to C30 alkynyl group, substituted or unsubstituted silyl group, substituted or Unsubstituted silyloxy group, substituted or unsubstituted C1 to C30 acyl group, substituted or unsubstituted C1 to C20 acyloxy group, substituted or unsubstituted C1 to C20 acylamino group, substituted or unsubstituted C1 to C30 sulfo Nyl group, substituted or unsubstituted C 1 to C30 alkylthiol group, substituted or unsubstituted C1 to C30 heterocyclothiyl group, substituted or unsubstituted C6 to C30 arylthiol group,
- R 9 and R 10 , or R 1 1 and R 12 fuse to form a ring
- M is Ir, Os, Pt, Pb, Re, Ru, or Pd,
- n and m are each independently an integer of 1 or 2, and n + m is an integer of 3.
- the present invention in another embodiment, it includes an anode and a cathode facing each other, and at least one organic layer positioned between the anode and the cathode, the organic layer comprises a compound according to an embodiment of the present invention described above It provides an organic optoelectronic device comprising.
- a display device including the organic optoelectronic device according to the embodiment of the present invention described above is provided.
- the organic optoelectronic device including the compound has excellent electrochemical and thermal stability, excellent life characteristics, and high luminous efficiency even at a low driving voltage.
- the compound for an organic optoelectronic device may be suitable for a deposition process or a solution process.
- FIG. 1 and 2 are cross-sectional views showing various embodiments of an organic light emitting device that can be manufactured using a compound according to an embodiment of the present invention. ⁇ Explanation of symbols for main parts of the drawings>
- organic light emitting element 200 organic light emitting element
- substituted means that at least one hydrogen in a substituent or compound is deuterium, halogen, hydroxy, amino, substituted or unsubstituted.
- C1 to C30 amine group nitro group, substituted or unsubstituted C3 to C40 silyl group, C 1 to C30 alkyl group, C1 to C10 alkylsilyl group, C3 to C30 cycloalkyl group, C6 to C30 aryl group, C 1 to C20 alkoxy Mean substituted by a C 1 to C 10 trifluoroalkyl group or a cyano group such as a group, a fluoro group, a trifluoromethyl group.
- substituted halogen group hydroxy group, amino group, substituted or unsubstituted C 1 to C20 amine group, nitro group, substituted or unsubstituted C3 to C40 silyl group, C1 to C30 alkyl group, C 1 to C 10 alkylsilyl group , C3 to C30 cycloalkyl group, C6 to C30 aryl group,
- C 1 to C 10 such as C 1 to C 20 alkoxy group, fluoro group and trifluoromethyl group
- Two adjacent substituents of the trifluoroalkyl group or the cyano group may be fused to form a ring.
- hetero means one to three hetero atoms selected from the group consisting of ⁇ , ⁇ , S, and ⁇ in one functional group, and the rest are carbon.
- an "alkyl group” is aliphatic.
- the alkyl group may be a "saturated alkyl group" that does not contain any double or triple bonds.
- the alkyl group may be an alkyl group which is C 1 to C20. More specifically, the alkyl group is C1 To CIO alkyl group or CI to C6 alkyl group.
- a C1 to C4 alkyl group means that the alkyl chain contains 1 to 4 carbon atoms, with methyl, ethyl, propyl, iso-propyl, ⁇ -butyl, iso-butyl, sec-butyl and t-butyl Selected from the group consisting of:
- alkyl group examples include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, pentyl group, nucleosil group, cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclonucleus It means a practical skill.
- Aryl group means a substituent in which all elements of the cyclic substituent have p-orbitals, and these P-orbitals form a conjugate, and are monocyclic or fused ring polycyclic (i.e., And ring) functional groups that divide adjacent pairs of carbon atoms.
- Heteroaryl group means containing 1 to 3 heteroatoms selected from the group consisting of N, 0, S and P in the aryl group, and the rest are carbon. When the heteroaryl group is a fused ring, each ring may include one of three heteroatoms.
- substituted or unsubstituted aryl group and / or substituted or unsubstituted heteroaryl group is substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthracenyl group, substituted or unsubstituted A substituted phenanthryl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted P-terphenyl group, a substituted or unsubstituted m-terphenyl group Substituted or unsubstituted chrysenyl group, substituted or unsubstituted triphenylenyl group, substituted or unsubstituted perenyl group, substituted or unsubstituted
- the hole characteristic means a characteristic that has conductivity characteristics along the HOMO level to facilitate injection of holes formed at the anode into the light emitting layer and movement in the light emitting layer. More specifically, it may be similar to the property of repelling electrons.
- an electronic characteristic means the characteristic which has electroconductive characteristic along LUMO level, and facilitates the injection of the electron formed in the cathode into the light emitting layer, and the movement in the light emitting layer. More specifically, it may be similar to the property of attracting electrons.
- R 1 to R 6 are each independently hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted silyl group,
- R 1 to R 3 is a substituted or unsubstituted C6 to C30 aryl group
- R 4 to R 6 is a substituted or unsubstituted C1 to C4 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted silyl group
- X 1 and X 2 are each independently 0, S, SO, S0 2 , POR 7 , NR 8 , CR 9 R 10 , or SiR u R 12 ,
- R 7 to R 12 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted C3 to C30 heterocycloalkyl group, substituted or Unsubstituted C6 to C30 aryl group, substituted or unsubstituted C2 to C30 heteroaryl group, substituted or unsubstituted amine group substituted or unsubstituted C6 to C30 arylamine group, substituted or unsubstituted C6 to C30 solution Teroarylamine groups, substituted or unsubstituted C1 to C30 alkoxy groups, substituted or unsubstituted C2 to C30 alkoxycarbonyl groups, substituted or unsubstituted C2 to C30
- Aryloxycarbonylamino group substituted or unsubstituted C1 to C30 sulfamoylamino group, substituted or unsubstituted C2 to C30 alkenyl group, substituted or unsubstituted C2 to C30 alkynyl group, substituted or unsubstituted silyl group, substituted or Unsubstituted silyloxy group, substituted or unsubstituted C1 to C30 acyl group, substituted or unsubstituted C1 to C20 acyloxy group, substituted or unsubstituted C1 to C20 acylamino group, substituted or unsubstituted C1 to C30 sulfo Nyl group, substituted or unsubstituted C1 to C30 alkylthiyl group, substituted or unsubstituted C1 to C30 heterocyclothiol group, substituted or unsubstituted C6 to C30 arylthiyl group,
- R 9 and R 10 , or R 1 1 and R 12 fuse to form a ring
- M is Ir, Os, Pt, Pb, Re, Ru, or Pd,
- n and m are each independently an integer of 1 or 2, and n + m is an integer of 3.
- the compound represented by Chemical Formula 1 may have excellent heat resistance and lifespan characteristics, and may have high luminous efficiency even at low bulb voltage.
- the compound according to an embodiment of the present invention reduces the triplet-triple extinction phenomenon that is the most problematic in OLED by introducing a substituent to R 1 to R 3 , and R 4 to R 6 of at least one ligand.
- a substituent to R 1 to R 3 , and R 4 to R 6 of at least one ligand it is possible to increase the affinity with the host, thereby suppressing the triplet-triplet annihilation caused by aggregation.
- Luminous efficiency and luminance characteristics can be improved compared to the case of using a pyridine-based iridium compound.
- the compound represented by Formula 1 may exhibit a blue shift, compared to a compound in which X 1 or X 2 is not bridged, and thus, a color may be combined with an appropriate host. Since the expression area can be widened, the compound according to the embodiment of the present invention emits light from blue to green.
- any one of R 1 to R 3 may be a substituted or unsubstituted C6 to C 10 aryl group, more specifically a substituted or unsubstituted phenyl group.
- any one of R 4 to R 6 is a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted silyl group, Or a substituted or unsubstituted phenyl group, more specifically, an unsubstituted methyl group, an unsubstituted ethyl group, isopropyl group, t-butyl group,
- Trimethylsilyl group or an unsubstituted phenyl group.
- R 1 to R 6 are as described above, an organic optoelectronic device having excellent thermal stability and lifespan characteristics and high luminous efficiency even at a low driving voltage may be manufactured.
- R 1 to R 3 when any one of R 1 to R 3 is a phenyl group, the color purity of green light emission does not change, and there is an effect of increasing the total volume of molecules, thereby minimizing intermolecular interactions, thereby realizing a high efficiency long life light emitting device.
- X 1 and X 2 are each independently, 0, S, POR 7 , NR 8 , CR 9 R 10 , or
- SiRi 'R 12 wherein R 7 to R 12 may each independently be a C 1 to C 4 alkyl group.
- R 1 to R 3 is a substituted or unsubstituted phenyl group
- any one of R 4 to R 6 is an unsubstituted methyl group, an unsubstituted ethyl group, isopropyl group, t-butyl Group, trimethylsilyl group, or an unsubstituted phenyl group
- X 1 and X 2 are each independently, CR 9 R 10 , wherein R 9 and R 10 may each independently be a C1 to C4 alkyl group.
- R 1 is an unsubstituted phenyl group
- R 5 is an unsubstituted methyl group, an unsubstituted ethyl group, isopropyl group, t-butyl group, or trimethylsilyl group
- R 9 and R 10 are each independently It may be a methyl group. However, it is not limited thereto.
- the compound has excellent thermal stability, lifetime characteristics and luminous efficiency.
- Specific examples of the compound according to an embodiment of the present invention may be any one of the compounds listed in Group I below, but is not limited thereto.
- the organic layer may include a light emitting layer, and the light emitting layer may include the compound.
- the compound is used in the organic layer to improve the life characteristics, efficiency characteristics, electrochemical stability and thermal stability of the organic optoelectronic device, it is possible to lower the driving voltage.
- the organic optoelectronic device may be an organic light emitting device.
- a cross-sectional view of an organic light emitting device is A cross-sectional view of an organic light emitting device.
- the organic light emitting diodes 100 and 200 may include an anode 120, a cathode 1 10, and at least one organic layer positioned between the anode and the cathode. It has a structure that includes (105).
- the anode 120 comprises an anode material, which is typically
- a material having a large work function is preferable to facilitate hole injection into the organic thin film layer.
- the positive electrode material may include metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold or alloys thereof, and include zinc oxide, indium oxide, indium tin oxide ( ⁇ ), and indium zinc oxide (IZO).
- metal oxides such as ZnO and A1 or combinations of metals and oxides such as Sn0 2 and Sb, and poly (3-methylthiophene), poly (3,4- (ethylene-1, 2-dioxy) thio 3 ⁇ 4) (poIyehtylenedioxythiophene: PEDT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.
- a transparent electrode including indium tin oxide (ITO) may be used as the anode.
- the negative electrode 1 10 includes a negative electrode material, which is usually used as a negative electrode material.
- the material has a small work function to facilitate electron injection into the organic thin film layer.
- the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, sesame, barium, or alloys thereof, and LiF / Multi-layered materials such as Al, Li0 2 / Al, LiF / Ca, LiF / Al, and BaF 2 / Ca, and the like, but are not limited thereto.
- a metal electrode such as aluminum may be used as the cathode.
- FIG. 1 illustrates that only the light emitting layer 130 exists as the organic layer 105.
- the organic light emitting diode 100 is shown, and the organic layer 105 may exist only as the light emitting layer 130.
- FIG. 2 includes an electron transport layer as the organic layer 105.
- the organic layer 105 includes the light emitting layer 230 and the hole transport layer 140, in which the light emitting layer 230 and the hole transport layer 140 exist. It may be two-layered. In this case, the light emitting layer 230 functions as an electron transporting layer, and the hole transporting layer 140 functions to improve bonding and hole transporting properties with a transparent electrode such as ⁇ .
- the organic layer 105 may further include an electron injection layer, an auxiliary electron transport insect, an electron transport layer, a major transport layer, an auxiliary major transport layer, and a major injection layer.
- the light emitting layers 130 and 230 and the hole transport layer 140 constituting the organic layer 105, an electron injection layer, an auxiliary electron transport layer, an electron transport layer, an electron transport layer, and an auxiliary hole, which may not be added, may be added.
- Any one selected from the group consisting of a hole transport layer, a hole injection layer, and a combination thereof includes the compound for an organic optoelectronic device.
- the compound for an organic optoelectronic device may be used in the light emitting layers 130 and 230, and may be used as a green phosphorescent dopant material in the light emitting layer.
- the organic thin film layer may be formed by a wet film method such as spin coating, dipping, flow coating, or the like, followed by cathode formation.
- a display device including the organic optoelectronic device is provided.
- HTM a-NPD (4,4'-bis [N- (l-napthyl) -N-phenyl-ammo] biphenyl
- HTM a-NPD (4,4'-bis [N- (l-napthyl) -N-phenyl-ammo] biphenyl
- Fir6 iridium (III) bis (4,6-difluorophenylpyridinato) tetrakis (II) represented by the following Chemical Formula Z-3 using a CDBP represented by Chemical Formula Z-2 as a host and a blue phosphorescent dopant on the hole transport layer.
- l-pyrazolyl) borate 3 ⁇ 4-10 was doped with a weight of 0 / o and vacuum deposition to form a light emitting layer of 300 A thickness.
- BAlq bis (2-methyl-8-quinolinolato-Nl, 08)-(l, r-Biphenyl-4-olato) aluminum
- BAlq bis (2-methyl-8-quinolinolato-Nl, 08)-(l, r-Biphenyl-4-olato) aluminum
- Alq3 tris (8-hydroxyquinolinato) aluminium
- An organic light emitting diode was manufactured by sequentially depositing LiF 5 A and A1 1000 A on the electron transport layer to form a cathode.
- Comparative Example 1 a dopant was manufactured in the same manner as in Comparative Example 1 except that [Formula T-1] was used instead of [Formula Z-3] to prepare a Comparative Example 2 device.
- Formula Tl [Formula T-1] was used instead of [Formula Z-3] to prepare a Comparative Example 2 device.
- Comparative Example 1 a dopant was manufactured in the same manner as in Comparative Example 1, except that [Formula ⁇ -2] was used instead of [Formula VII-3] to prepare a Comparative Example 3 device.
- An organic light emitting diode was manufactured according to the same method as Example 1 except for using the dopant according to Preparation Example 2 instead of the dopant according to Preparation Example 1.
- An organic light emitting diode was manufactured according to the same method as Example 1 except for using the dopant according to Preparation Example 3.
- Example 4 An organic light emitting diode was manufactured according to the same method as Example 1 except for using the dopant according to Preparation Example 4.
- An organic light emitting diode was manufactured according to the same method as Example 1 except for using the dopant according to Preparation Example 5.
- Example 6 An organic light emitting diode was manufactured according to the same method as Example 1 except for using the dopant according to Preparation Example 6.
- the current value flowing through the unit device was measured by using a current-voltmeter (Keithley 2400) while increasing the voltage from 0 V to 10 V, and the measured current value was divided by the area to obtain a result.
- the resulting organic light emitting device was measured using a luminance meter (Minolta Cs-I OOOA) while increasing the voltage from 0 V to 10 V to obtain a result.
- a luminance meter Minolta Cs-I OOOA
- the current efficiency (cd / A) of the same brightness (9000 cd / m 2 ) was calculated using the brightness, current density, and voltage measured from (1) and (2).
- the lifetime was measured by measuring the time until the luminous efficiency decreased by 3%, and the life of the materials provided in the present invention was relatively shown with the comparative example as 100%.
- Example 3 D-3 11.6 1 1 1 1 Example 4 D-4 8.7 125
- Example 5 D-5 9.9 107
- Example 6 D-6 10.7 99
- Table 1 in the case of a device fabricated using the material provided in the present invention, luminous efficiency or lifespan You can see that it is much better. This shows the possibility that the compound prepared in the present invention can be used as a material for a good organic light emitting device.
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Abstract
Provided are: a compound represented by chemical formula 1; an organic optoelectric diode including the same; and a display device including the organic optoelectric diode. The structure of the compound represented by chemical formula 1 is disclosed in the present specification.
Description
【명세서】 【Specification】
【발명의 명칭】 [Name of invention]
화합물， 이를 포함하는 유기광전자소자 및 표시장치 Compound, organic optoelectronic device and display device comprising same
【기술분야】 Technical Field
화합물, 유기광전자소자 및 표시장치에 관한 것이다. A compound, an organic optoelectronic device, and a display device are provided.
【배경기술】 Background Art
유기광전자소자 (organic optoelectric diode)는 전기 에너지와 광 에너지를 상호 전환할 수 있는 소자이다. An organic optoelectric diode is a device capable of converting electrical energy and optical energy.
유기광전자소자는 동작 원리에 따라 크게 두 가지로 나눌 수 있다. 하나는 광 에너지에 의해 형성된 액시톤 (exciton)이 전자와 정공으로 분리되고 상기 전자와 정공이 각'각 다른 전극으로 전달되면서 전기 에너지를 발생하는 광전 소자이고, 다른 하나는 전극에 전압 또는 전류를 공급하여 전기 에너지로부터 광 에너지를 발생하는 발광 소자이다. Organic optoelectronic devices can be divided into two types according to the principle of operation. One of the axial tone (exciton) formed by the light energy is separated into electrons and holes, and a photoelectric device in which the electrons and holes generates electric energy as each "Route to each other electrode, and the other is a voltage or current to the electrode It is a light emitting device that supplies and generates light energy from electrical energy.
유기광전자소자의 예로는 유기 광전 소자， 유기 발광 소자, 유기 태양 전지 및 유기 감광체 드럼 (organic photo conductor drum) 등을 들 수 있다. Examples of the organic optoelectronic device include an organic photoelectric device, an organic light emitting device, an organic solar cell, and an organic photo conductor drum.
이 중, 유기 발광 소자 (organic light emitting diode, OLED)는 근래 평판 표시 장치 (flat panel display device)의 수요 증가에 따라 크게 주목받고 있다. 상기 유기 발광 소자는 유기 발광 재료에 전류를 가하여 전기 에너지를 빛으로 전환시키는 소자로서， 통상 양극 (anode)과 음극 (cathode) 사이에 유기 층이 삽입된 구조로 이루어져 있다. 여기서 유기 층은 발광층과 선택적으로 보조층을 포함할 수 있으며 상기 보조층은 예컨대 유기발광소자의 효율과 안정성을 높이기 위한 정공 주입 층， 정공 수송 층, 전자 차단 층， 전자 수송 층， 전자 주입 층 및 정공 차단 층에서 선택된 적어도 1층을 포함할 수 있다. Among these, organic light emitting diodes (OLEDs) have attracted much attention recently as demand for flat panel displays increases. The organic light emitting device converts electrical energy into light by applying an electric current to the organic light emitting material. The organic light emitting device has a structure in which an organic layer is inserted between an anode and a cathode. The organic layer may include a light emitting layer and an auxiliary layer, and the auxiliary layer may include, for example, a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer, an electron injection layer, and the like, to increase the efficiency and stability of the organic light emitting device. It may comprise at least one layer selected from the hole blocking layer.
유기 발광 소자의 성능은 상기 유기 층의 특성에 의해 영향을 많이 받으며， 그 중에서도 상기 유기 층에 포함된 유기 재료에 의해 영향을 많이 받는다. The performance of the organic light emitting device is greatly influenced by the characteristics of the organic layer, and in particular, by the organic materials included in the organic layer.
특히 상기 유기 발광 소자가 대형 평판 표시 장치에 적용되기 위해서는 정공 및 전자의 이동성을 높이는 동시에 전기화학적 안정성을 높일 수 있는 유기 재료의 개발이 필요하다. In particular, in order for the organic light emitting diode to be applied to a large flat panel display, it is necessary to develop an organic material capable of increasing the mobility of holes and electrons and increasing electrochemical stability.
【발명의 상세한 설명】 [Detailed Description of the Invention]
【기술적 과제】
고효율, 장수명, 열적 안정성 등의 특성을 가지는 유기광전자소자를 제공할 수 있는 화합물을 제공하는 것이다. [Technical problem] It is to provide a compound that can provide an organic optoelectronic device having characteristics such as high efficiency, long life, thermal stability.
상기 화합물을 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치를 제공하는 것이다. An organic light emitting device including the compound and a display device including the organic light emitting device are provided.
【기술적 해결방법】 Technical Solution
본 발명의 일 구현예에서는, 하기 화학식 1로 표시되는 화합물을 제공한다. In one embodiment of the present invention, a compound represented by Chemical Formula 1 is provided.
상기 화학식 1에서, In Chemical Formula 1,
R1 내지 R6은 각각 독립적으로 수소, 중수소， 할로겐기, 시아노기， 치환 또는 비치환된 C1 내지 C20 알킬기， 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 실릴기이고, R 1 to R 6 are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted silyl group,
여기서 R1 내지 R3 중 어느 하나는 치환 또는 비치환된 C6 내지 C30 Wherein any one of R 1 to R 3 is substituted or unsubstituted C6 to C30
아릴기이고, An aryl group,
R4 내지 R6 중 어느 하나는 치환 또는 비치환된 C1 내지 C4 알킬기, 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 실릴기이고, Any one of R 4 to R 6 is a substituted or unsubstituted C1 to C4 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted silyl group,
X1 및 X2는 각각 독립적으로, 0, S, SO, S02, POR7, NR8, CR9R10, 또는 X 1 and X 2 are each independently 0, S, SO, S0 2 , POR 7 , NR 8 , CR 9 R 10 , or
SiR1ᅳ R12이고, SiR 1 ᅳ R 12 ,
여기서 R7 내지 R12은 각각 독립적으로, 수소， 중수소， 치환 또는 비치환된 C1 내지 C30 알킬기, 치환 또는 비치환된 C3 내지 C30 사이클로알킬기, 치환 또는 비치환된 C3 내지 C30 헤테로사이클로알킬기, 치환 또는 비치환된 C6 내지 C30 아릴기， 치환 또는 비치환된 C2 내지 C30 해테로아릴기, 치환 또는 비치환된 아민기 치환 또는 비치환된 C6 내지 C30 아릴아민기, 치환 또는 비치환된 C6 내지 C30 헤테로아릴아민기， 치환 또는 비치환된 C 1 내지 C30 알콕시기， 치환 또는 비치환된
C2 내지 C30 알콕시카르보닐기, 치환 또는 비치환된 C2 내지 C30 Wherein R 7 to R 12 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted C3 to C30 heterocycloalkyl group, substituted or Unsubstituted C6 to C30 aryl group, substituted or unsubstituted C2 to C30 heteroaryl group, substituted or unsubstituted amine group substituted or unsubstituted C6 to C30 arylamine group, substituted or unsubstituted C6 to C30 hetero Arylamine group, substituted or unsubstituted C 1 to C30 alkoxy group, substituted or unsubstituted C2 to C30 alkoxycarbonyl group, substituted or unsubstituted C2 to C30
알콕시카르보닐아미노기, 치환 또는 비치환된 C7 내지 C30 Alkoxycarbonylamino group, substituted or unsubstituted C7 to C30
아릴옥시카르보닐아미노기, 치환 또는 비치환된 C1 내지 C30 술파모일아미노기, 치환 또는 비치환된 C2 내지 C30 알케닐기, 치환 또는 비치환된 C2 내지 C30 알키닐기， 치환 또는 비치환된 실릴기, 치환 또는 비치환된 실릴옥시기, 치환 또는 비치환된 C1 내지 C30 아실기， 치환 또는 비치환된 C1 내지 C20 아실옥시기， 치환 또는 비치환된 C1 내지 C20 아실아미노기, 치환 또는 비치환된 C1 내지 C30 술포닐기, 치환 또는 비치환된 C 1 내지 C30 알킬티올기, 치환 또는 비치환된 C1 내지 C30 해테로사이클로티을기, 치환 또는 비치환된 C6 내지 C30 아릴티올기, 치환 또는 비치환된 C1 내지 C30 헤테로아릴티올기, 치환 또는 비치환된 C1 내지 C30 우레이드기, 할로겐기, 할로겐 함유기, 시아노기, 히드록실기, 아미노기, 니트로기, 카르복실기, 페로세닐기 또는 이들의 조합이거나 Aryloxycarbonylamino group, substituted or unsubstituted C1 to C30 sulfamoylamino group, substituted or unsubstituted C2 to C30 alkenyl group, substituted or unsubstituted C2 to C30 alkynyl group, substituted or unsubstituted silyl group, substituted or Unsubstituted silyloxy group, substituted or unsubstituted C1 to C30 acyl group, substituted or unsubstituted C1 to C20 acyloxy group, substituted or unsubstituted C1 to C20 acylamino group, substituted or unsubstituted C1 to C30 sulfo Nyl group, substituted or unsubstituted C 1 to C30 alkylthiol group, substituted or unsubstituted C1 to C30 heterocyclothiyl group, substituted or unsubstituted C6 to C30 arylthiol group, substituted or unsubstituted C1 to C30 hetero Arylthiol group, substituted or unsubstituted C1 to C30 ureide group, halogen group, halogen-containing group, cyano group, hydroxyl group, amino group, nitro group, carboxyl group, ferrocenyl group or a combination thereof I
R9 및 R10, 또는 R1 1 및 R12이 융합하여 고리를 형성하고, R 9 and R 10 , or R 1 1 and R 12 fuse to form a ring,
M은 Ir, Os, Pt, Pb, Re, Ru, 또는 Pd이고, M is Ir, Os, Pt, Pb, Re, Ru, or Pd,
n및 m은 각각 독립적으로 1 또는 2의 정수 중 어느 하나이고, n + m은 3의 정수이다. n and m are each independently an integer of 1 or 2, and n + m is an integer of 3.
본 발명의 다른 일 구현예에서는, 서로 마주하는 양극과 음극, 및 상기 양극과 상기 음극 사이에 위치하는 적어도 한 층의 유기층을 포함하고, 상기 유기층은 전술한 본 발명의 일 구현예에 따른 화합물을 포함하는 유기광전자소자를 제공한다. In another embodiment of the present invention, it includes an anode and a cathode facing each other, and at least one organic layer positioned between the anode and the cathode, the organic layer comprises a compound according to an embodiment of the present invention described above It provides an organic optoelectronic device comprising.
본 발명의 또 다른 일 구현예에서는， 전술한 본 발명의 일 구현예인 유기광전자소자를 포함하는 표시장치를 제공한다. In another embodiment of the present invention, a display device including the organic optoelectronic device according to the embodiment of the present invention described above is provided.
【유리한 효과】 Advantageous Effects
상기 화합물을 포함하는 유기광전자소자는 우수한 전기화학적 및 열적 안정성을 가지고 수명 특성이 우수하며, 낮은 구동전압에서도 높은 발광효율을 가질 수 있다. 또한 상기 유기광전자소자용 화합물은 증착 공정 또는 용액 공정에 적합할 수 있다. The organic optoelectronic device including the compound has excellent electrochemical and thermal stability, excellent life characteristics, and high luminous efficiency even at a low driving voltage. In addition, the compound for an organic optoelectronic device may be suitable for a deposition process or a solution process.
【도면의 간단한 설명】 [Brief Description of Drawings]
도 1 및 도 2는 본 발명의 일 구현예에 따른 화합물을 이용하여 제조될 수 있는 유기발광소자에 대한 다양한 구현예들을 나타내는 단면도이다.
<도면의 주요 부분에 대한 부호의 설명 > 1 and 2 are cross-sectional views showing various embodiments of an organic light emitting device that can be manufactured using a compound according to an embodiment of the present invention. <Explanation of symbols for main parts of the drawings>
100: 유기 발광 소자 200: 유기 발광 소자 100: organic light emitting element 200: organic light emitting element
105: 유기층 105: organic layer
1 10: 음극 1 10: cathode
120: 양극 120: anode
130: 발광층 230: 발광층 130: light emitting layer 230: light emitting layer
140: 정공 보조층 140: hole auxiliary layer
【발명의 실시를 위한 최선의 형태】 [Best form for implementation of the invention]
이하， 본 발명의 구현예를 상세히 설명하기로 한다. 다만, 이는 예시로서 제시되는 것으로, 이에 의해 본 발명이 제한되지는 않으며 본 발명은 후술할 청구범위의 범주에 의해 정의될 뿐이다. Hereinafter, embodiments of the present invention will be described in detail. However, this is presented as an example, by which the present invention is not limited and the present invention is defined only by the scope of the claims to be described later.
본 명세서에서 "치환"이란 별도의 정의가 없는 한, 치환기 또는 화합물 중의 적어도 하나의 수소가 중수소， 할로겐기， 히드록시기, 아미노기, 치환 또는 비치환된 As used herein, unless otherwise defined, “substituted” means that at least one hydrogen in a substituent or compound is deuterium, halogen, hydroxy, amino, substituted or unsubstituted.
C1 내지 C30 아민기， 니트로기, 치환 또는 비치환된 C3 내지 C40 실릴기, C 1 내지 C30 알킬기, C1 내지 C10 알킬실릴기, C3 내지 C30 시클로알킬기, C6 내지 C30 아릴기, C 1 내지 C20 알콕시기, 플루오로기, 트리플루오로메틸기 등의 C 1 내지 C10 트리플루오로알킬기 또는 시아노기로 치환된 것을 의미한다. C1 to C30 amine group, nitro group, substituted or unsubstituted C3 to C40 silyl group, C 1 to C30 alkyl group, C1 to C10 alkylsilyl group, C3 to C30 cycloalkyl group, C6 to C30 aryl group, C 1 to C20 alkoxy Mean substituted by a C 1 to C 10 trifluoroalkyl group or a cyano group such as a group, a fluoro group, a trifluoromethyl group.
또한 상기 치환된 할로겐기, 히드록시기， 아미노기, 치환 또는 비치환된 C 1 내지 C20 아민기, 니트로기, 치환 또는 비치환된 C3 내지 C40 실릴기， C1 내지 C30 알킬기， C 1 내지 C 10 알킬실릴기， C3 내지 C30 시클로알킬기, C6 내지 C30 아릴기， In addition, the substituted halogen group, hydroxy group, amino group, substituted or unsubstituted C 1 to C20 amine group, nitro group, substituted or unsubstituted C3 to C40 silyl group, C1 to C30 alkyl group, C 1 to C 10 alkylsilyl group , C3 to C30 cycloalkyl group, C6 to C30 aryl group,
C1 내지 C20 알콕시기, 플루오로기, 트리플루오로메틸기 등의 C 1 내지 C10 C 1 to C 10 such as C 1 to C 20 alkoxy group, fluoro group and trifluoromethyl group
트리플루오로알킬기 또는 시아노기 중 인접한 두 개의 치환기가 융합되어 고리를 형성할 수도 있다. Two adjacent substituents of the trifluoroalkyl group or the cyano group may be fused to form a ring.
본 명세서에서 "헤테로"란 별도의 정의가 없는 한, 하나의 작용기 내에 Ν, Ο, S 및 Ρ로 이루어진 군에서 선택되는 헤테로 원자를 1 내지 3개 함유하고, 나머지는 탄소인 것을 의미한다. As used herein, "hetero" means one to three hetero atoms selected from the group consisting of Ν, Ο, S, and Ρ in one functional group, and the rest are carbon.
본 명세서에서 "알킬 (alkyl)기''이란 별도의 정의가 없는 한， 지방족 As used herein, unless otherwise defined, an "alkyl group" is aliphatic.
탄화수소기를 의미한다. 알킬기는 어떠한 이중결합이나 삼중결합을 포함하고 있지 않은 "포화 알킬 (saturated alkyl)기' '일 수 있다. It means a hydrocarbon group. The alkyl group may be a "saturated alkyl group" that does not contain any double or triple bonds.
알킬기는 C 1 내지 C20인 알킬기일 수 있다. 보다 구체적으로 알킬기는 C1
내지 CIO 알킬기 또는 CI 내지 C6 알킬기일 수도 있다. 예를 들어, C1 내지 C4 알킬기는 알킬쇄에 1 내지 4 개의 탄소원자가 포함되는 것을 의미하며, 메틸, 에틸, 프로필, 이소-프로필 , η-부틸, 이소-부틸， sec-부틸 및 t-부틸로 이루어진 군에서 선택됨을 나타낸다. The alkyl group may be an alkyl group which is C 1 to C20. More specifically, the alkyl group is C1 To CIO alkyl group or CI to C6 alkyl group. For example, a C1 to C4 alkyl group means that the alkyl chain contains 1 to 4 carbon atoms, with methyl, ethyl, propyl, iso-propyl, η-butyl, iso-butyl, sec-butyl and t-butyl Selected from the group consisting of:
상기 알킬기는 구체적인 예를 들어 메틸기, 에틸기, 프로필기, 이소프로필기， 부틸기, 이소부틸기， t-부틸기， 펜틸기， 핵실기, 시클로프로필기, 시클로부틸기， 시클로펜틸기， 시클로핵실기 등을 의미한다. Specific examples of the alkyl group include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, pentyl group, nucleosil group, cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclonucleus It means a practical skill.
"아릴 (aryl)기"는 환형인 치환기의 모든 원소가 p-오비탈을 가지고 있으며， 이들 P-오비탈이 공액 (conjugation)을 형성하고 있는 치환기를 의미하고, 모노시클릭 또는 융합 고리 폴리시클릭 (즉, 탄소원자들의 인접한 쌍들을 나눠 가지는 고리) 작용기를 포함한다. "Aryl group" means a substituent in which all elements of the cyclic substituent have p-orbitals, and these P-orbitals form a conjugate, and are monocyclic or fused ring polycyclic (i.e., And ring) functional groups that divide adjacent pairs of carbon atoms.
"헤테로아릴 (heteroaryl)기"는 아릴기 내에 N, 0， S 및 P로 이루어진 군에서 선택되는 헤테로 원자를 1 내지 3개 함유하고, 나머지는 탄소인 것을 의미한다. 상기 헤테로아릴기가 융합고리인 경우, 각각의 고리마다 상기 해테로 원자를 1 내 3개 포함할 수 있다. "Heteroaryl group" means containing 1 to 3 heteroatoms selected from the group consisting of N, 0, S and P in the aryl group, and the rest are carbon. When the heteroaryl group is a fused ring, each ring may include one of three heteroatoms.
보다 구체적으로, 치환 또는 비치환된 아릴기 및 /또는 치환 또는 비치환된 헤테로아릴기는， 치환 또는 비차환된 페닐기, 치환 또는 비치환된 나프틸기, 치환 또는 비치환된 안트라세닐기， 치환 또는 비치환된 페난트릴기, 치환 또는 비치환된 나프타세닐기, 치환 또는 비치환된 피레닐기, 치환 또는 비치환된 바이페닐기, 치환 또는 비치환된 P-터페닐기, 치환 또는 비치환된 m-터페닐기， 치환또는 비치환된 크리세닐기, 치환 또는 비치환된 트리페닐레닐기， 치환 또는 비치환된 페릴레닐기, 치환 또는 비치환된 인데닐기, 치환 또는 비치환된 퓨라닐기, 치환 또는 비치환된 티오페닐기, 치환 또는 비치환된 피를릴기, 치환 또는 비치환된 피라졸릴기， 치환 또는 비치환된 이미다졸일기, 치환 또는 비치환된 트리아졸일기， 치환 또는 More specifically, the substituted or unsubstituted aryl group and / or substituted or unsubstituted heteroaryl group is substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthracenyl group, substituted or unsubstituted A substituted phenanthryl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted P-terphenyl group, a substituted or unsubstituted m-terphenyl group Substituted or unsubstituted chrysenyl group, substituted or unsubstituted triphenylenyl group, substituted or unsubstituted perenyl group, substituted or unsubstituted indenyl group, substituted or unsubstituted furanyl group, substituted or unsubstituted Thiophenyl group, substituted or unsubstituted pyryl group, substituted or unsubstituted pyrazolyl group, substituted or unsubstituted imidazolyl group, substituted or unsubstituted triazolyl group, substituted or
비치환된 옥사졸일기， 치환 또는 비치환된 티아졸일기, 치환 또는 비치환된 Unsubstituted oxazolyl group, substituted or unsubstituted thiazolyl group, substituted or unsubstituted
옥사디아졸일기, 치환 또는 비치환된 티아디아졸일기, 치환 또는 비치환된 피리딜기: 치환 또는 비치환된 피리미디닐기, 치환 또는 비치환된 피라지닐기, 치환 또는 비치환된 트리아지닐기， 치환 또는 비치환된 벤조퓨라닐기, 치환 또는 비치환된 벤조티오페닐기， 치환 또는 비치환된 벤즈이미다졸일기, 치환 또는 비치환된 인돌일기, 치환 또는 비치환된 퀴놀리닐기, 치환 또는 비치환된 이소퀴놀리닐기，
치환 또는 비치환된 퀴나졸리닐기, 치환 또는 비치환된 퀴녹살리닐기， 치환 또는 비치환된 나프티리디닐기, 치환 또는 비치환된 벤즈옥사진일기, 치환 또는 비치환된 벤즈티아진일기， 치환 또는 비치환된 아크리디닐기, 치환 또는 비치환된 페나진일기, 치환 또는 비치환된 페노티아진일기， 치환 또는 비치환된 페녹사진일기, 치환 또는 비치환된 플루오레닐기, 치환 또는 비치환된 카바졸일기， 치환 또는 비치환된 디벤조퓨라닐기, 치환 또는 비치환된 디벤조티오페닐기， 또는 이들의 조합일 수 있으나， 이에 제한되지는 않는다. Oxadiazolyl group, substituted or unsubstituted thiadiazolyl group, substituted or unsubstituted pyridyl group : substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted triazinyl group, Substituted or unsubstituted benzofuranyl group, substituted or unsubstituted benzothiophenyl group, substituted or unsubstituted benzimidazolyl group, substituted or unsubstituted indolyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted Isoquinolinyl group ， Substituted or unsubstituted quinazolinyl group, substituted or unsubstituted quinoxalinyl group, substituted or unsubstituted naphthyridinyl group, substituted or unsubstituted benzoxazinyl group, substituted or unsubstituted benzthiazinyl group, substituted or unsubstituted A substituted acridinyl group, a substituted or unsubstituted phenazineyl group, a substituted or unsubstituted phenothiazineyl group, a substituted or unsubstituted phenoxazineyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazole It may be a diary, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof, but is not limited thereto.
본 명세서에서, 정공 특성이란, HOMO 준위를 따라 전도 특성을 가져 양극에서 형성된 정공의 발광층으로의 주입 및 발광층에서의 이동을 용이하게 하는 특성을 의미한다. 보다 구체적으로， 전자를 밀어내는 특성과도 유사할 수 있다. In the present specification, the hole characteristic means a characteristic that has conductivity characteristics along the HOMO level to facilitate injection of holes formed at the anode into the light emitting layer and movement in the light emitting layer. More specifically, it may be similar to the property of repelling electrons.
또한 전자 특성이란, LUMO 준위를 따라 전도 특성을 가져 음극에서 형성된 전자의 발광층으로의 주입 및 발광층에서의 이동을 용이하게 하는 특성올 의미한다. 보다 구체적으로 전자를 당기는 특성과도 유사할 수 있다. In addition, an electronic characteristic means the characteristic which has electroconductive characteristic along LUMO level, and facilitates the injection of the electron formed in the cathode into the light emitting layer, and the movement in the light emitting layer. More specifically, it may be similar to the property of attracting electrons.
본 발명의 일 구현예에서는 하기 화학식 1로 표시되는 화합물을 제공한다. In one embodiment of the present invention provides a compound represented by the following formula (1).
상기 화학식 1에서， In Chemical Formula 1,
R1 내지 R6은 각각 독립적으로 수소， 중수소， 할로겐기, 시아노기, 치환 또는 비치환된 C1 내지 C20 알킬기, 치환 또는 비치환된 C6 내지 C30 아릴기， 또는 치환 또는 비치환된 실릴기이고, R 1 to R 6 are each independently hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted silyl group,
여기서 R1 내지 R3 중 어느 하나는 치환 또는 비치환된 C6 내지 C30 아릴기이고, Wherein any one of R 1 to R 3 is a substituted or unsubstituted C6 to C30 aryl group,
R4 내지 R6 중 어느 하나는 치환 또는 비치환된 C1 내지 C4 알킬기, 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 실릴기이고,
X1 및 X2는 각각 독립적으로, 0, S, SO, S02, POR7, NR8, CR9R10, 또는 SiRuR12이고, Any one of R 4 to R 6 is a substituted or unsubstituted C1 to C4 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted silyl group, X 1 and X 2 are each independently 0, S, SO, S0 2 , POR 7 , NR 8 , CR 9 R 10 , or SiR u R 12 ,
여기서 R7 내지 R12은 각각 독립적으로, 수소, 중수소， 치환 또는 비치환된 C1 내지 C30 알킬기, 치환 또는 비치환된 C3 내지 C30 사이클로알킬기, 치환 또는 비치환된 C3 내지 C30 헤테로사이클로알킬기, 치환 또는 비치환된 C6 내지 C30 아릴기, 치환 또는 비치환된 C2 내지 C30 해테로아릴기, 치환 또는 비치환된 아민기 치환 또는 비치환된 C6 내지 C30 아릴아민기, 치환 또는 비치환된 C6 내지 C30 해테로아릴아민기， 치환 또는 비치환된 C1 내지 C30 알콕시기, 치환 또는 비치환된 C2 내지 C30 알콕시카르보닐기, 치환 또는 비치환된 C2 내지 C30 Wherein R 7 to R 12 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted C3 to C30 heterocycloalkyl group, substituted or Unsubstituted C6 to C30 aryl group, substituted or unsubstituted C2 to C30 heteroaryl group, substituted or unsubstituted amine group substituted or unsubstituted C6 to C30 arylamine group, substituted or unsubstituted C6 to C30 solution Teroarylamine groups, substituted or unsubstituted C1 to C30 alkoxy groups, substituted or unsubstituted C2 to C30 alkoxycarbonyl groups, substituted or unsubstituted C2 to C30
알콕시카르보닐아미노기, 치환 또는 비치환된 C7 내지 C30 Alkoxycarbonylamino group, substituted or unsubstituted C7 to C30
아릴옥시카르보닐아미노기, 치환 또는 비치환된 C1 내지 C30 술파모일아미노기， 치환 또는 비치환된 C2 내지 C30 알케닐기, 치환 또는 비치환된 C2 내지 C30 알키닐기， 치환 또는 비치환된 실릴기, 치환 또는 비치환된 실릴옥시기， 치환 또는 비치환된 C1 내지 C30 아실기, 치환 또는 비치환된 C1 내지 C20 아실옥시기, 치환 또는 비치환된 C1 내지 C20 아실아미노기, 치환 또는 비치환된 C1 내지 C30 술포닐기, 치환 또는 비치환된 C1 내지 C30 알킬티을기, 치환 또는 비치환된 C1 내지 C30 헤테로사이클로티올기, 치환 또는 비치환된 C6 내지 C30 아릴티을기， 치환 또는 비치환된 C1 내지 C30 헤테로아릴티올기, 치환 또는 비치환된 C1 내지 C30 우레이드기, 할로겐기, 할로겐 함유기， 시아노기, 히드록실기, 아미노기， 니트로기， 카르복실기, 페로세닐기 또는 이들의 조합이거나 Aryloxycarbonylamino group, substituted or unsubstituted C1 to C30 sulfamoylamino group, substituted or unsubstituted C2 to C30 alkenyl group, substituted or unsubstituted C2 to C30 alkynyl group, substituted or unsubstituted silyl group, substituted or Unsubstituted silyloxy group, substituted or unsubstituted C1 to C30 acyl group, substituted or unsubstituted C1 to C20 acyloxy group, substituted or unsubstituted C1 to C20 acylamino group, substituted or unsubstituted C1 to C30 sulfo Nyl group, substituted or unsubstituted C1 to C30 alkylthiyl group, substituted or unsubstituted C1 to C30 heterocyclothiol group, substituted or unsubstituted C6 to C30 arylthiyl group, substituted or unsubstituted C1 to C30 heteroarylthiol Groups, substituted or unsubstituted C1 to C30 ureide groups, halogen groups, halogen-containing groups, cyano groups, hydroxyl groups, amino groups, nitro groups, carboxyl groups, ferrocenyl groups or groups thereof Or
R9 및 R10, 또는 R1 1 및 R12이 융합하여 고리를 형성하고, R 9 and R 10 , or R 1 1 and R 12 fuse to form a ring,
M은 Ir, Os, Pt, Pb, Re, Ru, 또는 Pd이고, M is Ir, Os, Pt, Pb, Re, Ru, or Pd,
n및 m은 각각 독립적으로 1 또는 2의 정수 중 어느 하나이고, n + m은 3의 정수이다. n and m are each independently an integer of 1 or 2, and n + m is an integer of 3.
이 경우 상기 화학식 1로 표시되는 화합물은 내열 안정성 및 수명 특성이 우수하고 낮은 구등전압에서도 높은 발광효율을 가질 수 있다. In this case, the compound represented by Chemical Formula 1 may have excellent heat resistance and lifespan characteristics, and may have high luminous efficiency even at low bulb voltage.
구체적으로, 본 발명의 일 구현예에 따른 화합물은 적어도 하나의 리간드의 R1 내지 R3, 및 R4 내지 R6에 치환체를 도입하여 OLED 에서 가장 문제가 되는 삼중항-삼중항 소멸현상을 감소시킬 수 있음은 물론이고, 호스트와의 친화력을 높여 어그리게이션에 의한 삼중항-삼중항 소멸현상을 억제시킴으로써 통상적인 페닐
피리딘계 이리듐화합물을 사용한 경우와 비교하여 발광효율과 휘도 특성이 개선될 수 있다. Specifically, the compound according to an embodiment of the present invention reduces the triplet-triple extinction phenomenon that is the most problematic in OLED by introducing a substituent to R 1 to R 3 , and R 4 to R 6 of at least one ligand. Of course, it is possible to increase the affinity with the host, thereby suppressing the triplet-triplet annihilation caused by aggregation. Luminous efficiency and luminance characteristics can be improved compared to the case of using a pyridine-based iridium compound.
또한， X1 또는 X2가 브릿지 (bridged) 됨으로써, X1 또는 X2가 브릿지 되어 있지 않은 화합물에 비해 상기 화학식 1로 표시되는 화합물은 블루 시프트가 나타날 수 있고， 이로 인하여 적절한 호스트와 조합하여 색 표현 영역을 넓힐 수 있게 되므로， 본 발명의 일 구현예에 따른 화합물은 청색에서부터 녹색에 이르는 빛을 In addition, when X 1 or X 2 is bridged, the compound represented by Formula 1 may exhibit a blue shift, compared to a compound in which X 1 or X 2 is not bridged, and thus, a color may be combined with an appropriate host. Since the expression area can be widened, the compound according to the embodiment of the present invention emits light from blue to green.
효율적으로 발광할 수 있다. It can emit light efficiently.
구체적인 예로， 상기 R1 내지 R3 중 어느 하나는 치환 또는 비치환된 C6 내지 C 10 아릴기， 더 구체적으로 치환 또는 비치환된 페닐기일 수 있다. As a specific example, any one of R 1 to R 3 may be a substituted or unsubstituted C6 to C 10 aryl group, more specifically a substituted or unsubstituted phenyl group.
또한, 상기 R4 내지 R6 중 어느 하나는 치환 또는 비치환된 메틸기， 치환 또는 비치환된 에틸기, 치환 또는 비치환된 프로필기， 치환 또는 비치환된 부틸기， 치환 또는 비치환된 실릴기, 또는 치환 또는 비치환된 페닐기일 수 있고, 더 구체적으로 비치환된 메틸기, 비치환된 에틸기, 이소프로필기, t-부틸기, In addition, any one of R 4 to R 6 is a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted silyl group, Or a substituted or unsubstituted phenyl group, more specifically, an unsubstituted methyl group, an unsubstituted ethyl group, isopropyl group, t-butyl group,
트리메틸실릴기, 또는 비치환된 페닐기일 수 있다. Trimethylsilyl group, or an unsubstituted phenyl group.
R1 내지 R6가 상기와 같은 경우， 내열 안정성 및 수명 특성이 우수하고 낮은 구동전압에서도 높은 발광효율을 가지는 유기광전자소자를 제작할 수 있다. When R 1 to R 6 are as described above, an organic optoelectronic device having excellent thermal stability and lifespan characteristics and high luminous efficiency even at a low driving voltage may be manufactured.
특히， R1 내지 R3 중 어느 하나가 페닐기인 경우 녹색 발광의 색순도가 변하지 않으며， 분자의 전체 부피를 증가시키는 효과가 있어 분자간 상호작용을 최소화하므로 고효율 장수명의 발광소자를 구현할 수 있다. In particular, when any one of R 1 to R 3 is a phenyl group, the color purity of green light emission does not change, and there is an effect of increasing the total volume of molecules, thereby minimizing intermolecular interactions, thereby realizing a high efficiency long life light emitting device.
한편, 상기 X1 및 X2는 각각 독립적으로 , 0, S, POR7, NR8, CR9R10, 또는 On the other hand, X 1 and X 2 are each independently, 0, S, POR 7 , NR 8 , CR 9 R 10 , or
SiRi 'R12이고, 여기서 R7 내지 R12는 각각 독립적으로 C 1 내지 C4 알킬기일 수 있다. 예컨대, 상기 화학식 1에서, R1 내지 R3 중 어느 하나는 치환 또는 비치환된 페닐기이고, R4 내지 R6 중 어느 하나는 비치환된 메틸기, 비치환된 에틸기， 이소프로필기, t-부틸기， 트리메틸실릴기, 또는 비치환된 페닐기이고， X1 및 X2는 각각 독립적으로, CR9R10이고， 여기서, R9 및 R10은 각각 독립적으로 C1 내지 C4 알킬기일 수 있다. SiRi 'R 12 , wherein R 7 to R 12 may each independently be a C 1 to C 4 alkyl group. For example, in Formula 1, any one of R 1 to R 3 is a substituted or unsubstituted phenyl group, any one of R 4 to R 6 is an unsubstituted methyl group, an unsubstituted ethyl group, isopropyl group, t-butyl Group, trimethylsilyl group, or an unsubstituted phenyl group, X 1 and X 2 are each independently, CR 9 R 10 , wherein R 9 and R 10 may each independently be a C1 to C4 alkyl group.
가장 구체적인 예로, R1은 비치환된 페닐기이고， R5은 비치환된 메틸기, 비치환된 에틸기, 이소프로필기, t-부틸기, 또는 트리메틸실릴기이고, R9 및 R10은 각각 독립적으로 메틸기일 수 있다. 다만, 이에 제한되는 것은 아니다. In the most specific example, R 1 is an unsubstituted phenyl group, R 5 is an unsubstituted methyl group, an unsubstituted ethyl group, isopropyl group, t-butyl group, or trimethylsilyl group, and R 9 and R 10 are each independently It may be a methyl group. However, it is not limited thereto.
이 경우 상기 화합물은 우수한 내열 안정성， 수명 특성 및 발광 효율을
구현할 수 있다ᅳ In this case, the compound has excellent thermal stability, lifetime characteristics and luminous efficiency. Can be implemented
본 발명의 일 구현예에 따른 화합물의 구체적인 예는 하기 그룹 I에 나열된 화합물 중 어느 하나일 수 있으나, 이에 한정되는 것은 아니다. Specific examples of the compound according to an embodiment of the present invention may be any one of the compounds listed in Group I below, but is not limited thereto.
[그룹 I] [Group I]
상기 유기층은 발광층을 포함하고, 상기 발광층은 상기 화합물을 포함할 수 있다. The organic layer may include a light emitting layer, and the light emitting layer may include the compound.
상기 화합물은 유기층에 사용되어 유기광전자소자의 수명 특성 , 효율 특성 , 전기화학적 안정성 및 열적 안정성을 향상시키며, 구동전압을 낮출 수 있다. The compound is used in the organic layer to improve the life characteristics, efficiency characteristics, electrochemical stability and thermal stability of the organic optoelectronic device, it is possible to lower the driving voltage.
보다 구체적으로, 상기 유기광전자소자는 유기발광소자일 수 있다. More specifically, the organic optoelectronic device may be an organic light emitting device.
도 1 및 도 2는 본 발명의 일 구현예에 따른 화합물을 포함하는 1 and 2 include a compound according to an embodiment of the present invention
유기발광소자의 단면도이다. A cross-sectional view of an organic light emitting device.
도 1 및 도 2를 참조하면, 본 발명의 일 구현예에 따른 유기발광소자 (100 및 200)는 양극 (120)， 음극 (1 10) 및 이 양극과 음극 사이에 위치하는 적어도 한 층의 유기층 (105)을 포함하는 구조를 갖는다. 1 and 2, the organic light emitting diodes 100 and 200 according to the exemplary embodiment of the present invention may include an anode 120, a cathode 1 10, and at least one organic layer positioned between the anode and the cathode. It has a structure that includes (105).
상기 양극 (120)은 양극 물질을 포함하며, 이 양극 물질로는 통상 The anode 120 comprises an anode material, which is typically
유기박막층으로 정공주입이 원활할 수 있도록 일 함수가 큰 물질이 바람직하다. 상기 양극 물질의 구체적인 예로는 니켈, 백금, 바나듐, 크롬, 구리, 아연， 금과 같은 금속 또는 이들의 합금을 들 수 있고, 아연산화물， 인듐산화물， 인듐주석산화물 (ΠΌ), 인듐아연산화물 (IZO)과 같은 금속 산화물을 들 수 있고, ZnO와 A1 또는 Sn02와 Sb와 같은 금속과 산화물의 조합을 들 수 있고, 폴리 (3-메틸티오펜)， 폴리 (3,4- (에틸렌 -1,2- 디옥시)티오 ¾)(poIyehtylenedioxythiophene: PEDT), 폴리피를 및 폴리아닐린과 같은 전도성 고분자 등을 들 수 있으나, 이에 한정되는 것은 아니다. 바람직하게는 상기 양극으로 ITO(indium tin oxide)를 포함하는 투명전극을 사용할 수 있다. A material having a large work function is preferable to facilitate hole injection into the organic thin film layer. Specific examples of the positive electrode material may include metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold or alloys thereof, and include zinc oxide, indium oxide, indium tin oxide (ΠΌ), and indium zinc oxide (IZO). And metal oxides such as ZnO and A1 or combinations of metals and oxides such as Sn0 2 and Sb, and poly (3-methylthiophene), poly (3,4- (ethylene-1, 2-dioxy) thio ¾) (poIyehtylenedioxythiophene: PEDT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto. Preferably, a transparent electrode including indium tin oxide (ITO) may be used as the anode.
상기 음극 (1 10)은 음극 물질을 포함하여, 이 음극 물질로는 통상 The negative electrode 1 10 includes a negative electrode material, which is usually used as a negative electrode material.
유기박막층으로 전자주입이 용이하도록 일 함수가 작은 물질인 것이 바람직하다. 음극 물질의 구체적인 예로는 마그네슴， 칼슘, 나트륨, 칼륨, 타이타늄, 인듐, 이트륨, 리튬, 가돌리늄， 알루미늄, 은, 주석， 납, 세슴, 바륨 등과 같은 금속 또는 이들의 합금을 들 수 있고, LiF/Al, Li02/Al, LiF/Ca, LiF/Al 및 BaF2/Ca과 같은 다층 구조 물질 등을 들 수 있으나, 이에 한정되는 것은 아니다. 바람직하게는 상기 음극으로 알루미늄 등과 같은 금속전극을 사용할 수 있다. It is preferable that the material has a small work function to facilitate electron injection into the organic thin film layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, sesame, barium, or alloys thereof, and LiF / Multi-layered materials such as Al, Li0 2 / Al, LiF / Ca, LiF / Al, and BaF 2 / Ca, and the like, but are not limited thereto. Preferably, a metal electrode such as aluminum may be used as the cathode.
먼저 도 1을 참조하면, 도 1은 유기층 (105)으로서 발광층 (130)만이 존재하는
유기발광소자 (100)를 나타낸 것으로, 상기 유기층 (105)은 발광층 (130)만으로 존재할 수 있다ᅳ Referring first to FIG. 1, FIG. 1 illustrates that only the light emitting layer 130 exists as the organic layer 105. The organic light emitting diode 100 is shown, and the organic layer 105 may exist only as the light emitting layer 130.
도 2를 참조하면, 도 2는 유기층 (105)으로서 전자수송층을 포함하는 Referring to FIG. 2, FIG. 2 includes an electron transport layer as the organic layer 105.
발광층 (230)과 정공수송층 (140)이 존재하는 2층형 유기발광소자 (200)를 나타낸 것으로, 도 2에 나타난 바와 같이， 유기층 (105)은 발광층 (230) 및 정공 수송층 (140)을 포함하는 2층형일 수 있다. 이 경우 발광층 (230)은 전자 수송층의 기능을 하며, 정공 수송층 (140)은 ΠΌ와 같은 투명전극과의 접합성 및 정공수송성을 향상시키는 기능을 한다. 도 1 및 도 2에서 유기층 (105)는， 도시하지는 않았지만 전자주입층, 보조전자수송충, 전자수송층, 전공수송층， 보조전공수송층, 전공주입층등을 추가로 더 포함할 수 있다. As shown in FIG. 2, the organic layer 105 includes the light emitting layer 230 and the hole transport layer 140, in which the light emitting layer 230 and the hole transport layer 140 exist. It may be two-layered. In this case, the light emitting layer 230 functions as an electron transporting layer, and the hole transporting layer 140 functions to improve bonding and hole transporting properties with a transparent electrode such as πΌ. Although not shown, the organic layer 105 may further include an electron injection layer, an auxiliary electron transport insect, an electron transport layer, a major transport layer, an auxiliary major transport layer, and a major injection layer.
상기 도 1 및 도 2에서 상기 유기층 (105)을 이루는 발광층 (130, 230), 정공 수송층 (140), 또한 도시하지는 않았지만 추가될 수 있는 전자주입층， 보조전자수송층, 전자수송층, 전공수송층, 보조전공수송층, 정공 주입층 및 이들의 조합으로 이루어진 군에서 선택되는 어느 하나는 상기 유기광전자소자용 화합물을 포함한다. 1 and 2, the light emitting layers 130 and 230 and the hole transport layer 140 constituting the organic layer 105, an electron injection layer, an auxiliary electron transport layer, an electron transport layer, an electron transport layer, and an auxiliary hole, which may not be added, may be added. Any one selected from the group consisting of a hole transport layer, a hole injection layer, and a combination thereof includes the compound for an organic optoelectronic device.
특히 상기 유기광전자소자용 화합물은 상기 발광층 (130, 230)에 사용될 수 있고, 이때 발광층 내에서 그린 (green)의 인광 도편트 재료로 사용될 수 있다. In particular, the compound for an organic optoelectronic device may be used in the light emitting layers 130 and 230, and may be used as a green phosphorescent dopant material in the light emitting layer.
상기에서 설명한 유기발광소자는， 기판에 양극을 형성한 후, In the organic light emitting device described above, after forming an anode on a substrate,
진공증착법 (evaporation), 스퍼터링 (sputtering), 플라즈마 도금 및 이온도금과 같은 건식성막법 ; 또는 스핀코팅 (spin coating), 침지법 (dipping), 유동코팅법 (flow coating)과 같은 습식성막법 등으로 유기박막층을 형성한 후, 그 위에 음극올 형성하여 제조할 수 있다. Dry film formation methods such as evaporation, sputtering, plasma plating and ion plating; Alternatively, the organic thin film layer may be formed by a wet film method such as spin coating, dipping, flow coating, or the like, followed by cathode formation.
본 발명의 또 다른 일 구현예에서는, 상기 유기광전자소자를 포함하는 표시장치를 제공한다. In another embodiment of the present invention, a display device including the organic optoelectronic device is provided.
【발명의 실시를 위한 형태】 [Form for implementation of invention]
이하에서는 본 발명의 구체적인 실시예들을 제시한다. 다만, 하기에 기재된 실시예들은 본 발명을 구체적으로 예시하거나 설명하기 위한 것에 불과하며， 이로서 본 발명이 제한되어서는 아니된다. The following presents specific embodiments of the present invention. However, the embodiments described below are merely for illustrating or explaining the present invention in detail, and thus the present invention is not limited thereto.
(화합물의 제조) Preparation of Compound
제조예 1: D-1 의 제조 Preparation Example 1 Preparation of D-1
[반웅식 1]
[Banungsik 1]
등근 바닥 플라스크에 바이페닐 -3-일 보론산 35.2 g (177.7 mmol), 메틸 2- 클로로 -5-메틸니코티네이트 30 g (161.6 mmol), 테트라키스 (트리페닐포스핀)팔라듐 35.2 g (177.7 mmol) of biphenyl-3-yl boronic acid, 30 g (161.6 mmol) of methyl 2-chloro-5-methylnicotinate, tetrakis (triphenylphosphine) palladium in a back bottom flask
[Pd(PPh3)4] 5.6 g (4.84 mmol), 포타슘카보네이트 44.68 g (323 mmol)을 THF 600 mL, 증류수 300 mL에 넣고 24시간 동안 가열 환류하였다. 반웅이 완결되면 상온으로 냉각하고 THF 와 증류수를 분리한다. THF 에 1200 mL 의 메탄올을 넣고 결정화 시킨다. 생성된 고형물을 거르고， 물과 메탄올로 씻어주었다. 진공오븐에서 고형물을 건조하여 화합물 -1을 35 g (수율 : 71%) 얻었다. 5.6 g (4.84 mmol) of [Pd (PPh 3 ) 4 ] and 44.68 g (323 mmol) of potassium carbonate were added to 600 mL of THF and 300 mL of distilled water, followed by heating to reflux for 24 hours. When reaction is complete, cool to room temperature and separate THF and distilled water. 1200 mL of methanol is added to THF and crystallized. The resulting solids were filtered off and washed with water and methanol. The solid was dried in a vacuum oven to obtain 35 g of a compound -1 (yield: 71%).
화합물 -2 의 제조 Preparation of Compound-2
등근 바닥 플라스크에 화합물 -1 35 g (115 mmol) 을 넣고 700 mL 의 무수 THF 로 녹인다 . 0 °C에서 메틸마그네슘 브로마이드 용액 307 mL 를 폴라스크에 적가한다. 반웅 종료 후, 암모늄클로라이드를 물 150 ml 에 녹여서 뒌칭시킨다. 유기 층과 물층을 분리한 다음 용매를 모두 제거한다. 칼럼크로마토그래피를 이용하여 화합물- 2를 32 g (수율 : 91%) 얻었다. Add 35 g (115 mmol) of compound-1 to the back bottom flask and dissolve in 700 mL of dry THF. 307 mL of methylmagnesium bromide solution is added dropwise to the polar flask at 0 ° C. After completion of reaction, ammonium chloride was quenched by dissolving in 150 ml of water. The organic and water layers are separated and then all solvent is removed. 32 g (yield: 91%) of compound-2 was obtained by column chromatography.
화합물 -3 의 제조 Preparation of Compound -3
질소 기류하 둥근 바닥 플라스크에 MC 용액에 화합물 -2 32 g (105 mmol)을 녹인 후, 보론트리플루오로 다이에틸 이써레이트 13.2 mL ( 105 mmol)을 적가한다. 하루 교반 후， 소듐 바이 카보네이트를 녹인 물을 넣고 ¾칭시킨다..반웅 종결 후 유기층을 분리한 다음 용매를 모두 제거한다음 핵산을 이용하여 화합물 -3을 25 g (수율 ： 83%) 얻었다. In a round bottom flask under nitrogen stream, 32 g (105 mmol) of Compound -2 was dissolved in MC solution, and then 13.2 mL (105 mmol) of borontrifluoro diethyl etherate was added dropwise. After stirring for one day, water was dissolved in sodium bicarbonate, and quenched. After completion of the reaction, the organic layer was separated, and then the solvent was removed. Then, 25 g of a compound-3 was obtained using a nucleic acid (yield: 83%).
화합물 -4 의 제조 Preparation of Compound -4
등근 바닥 플라스크에 화합물 -3 11.9 g (41.8 mmol)과 이리듐클로라이드 5 g (16.7 mmol), 2-에특시에탄을 90 mL, 증류수 30 mL를 넣고 24시간 동안 가열 11.9 g (41.8 mmol) of compound -3, 5 g (16.7 mmol) of iridium chloride, 90 mL of 2-ethoxyethane and 30 mL of distilled water were added to the back bottom flask and heated for 24 hours.
환류하였다ᅳ 반웅이 완결되면 상온으로 냉각하고 반웅중 생긴 고형물을 거르고, 물과 메탄올로 씻어주었다. 진공오본에서 고형물을 건조하여 화합물 -4를 15 g (수율 ： 51%) 얻었다. After the reaction was completed, the reaction mixture was cooled to room temperature, the solid formed in the reaction mixture was filtered, and washed with water and methanol. The solid was dried in a vacuum oven to obtain 15 g (yield: 51%) of compound -4.
화합물 -5 의 제조 Preparation of Compound-5
등근 바닥 플라스크에 화합물 -4 15 g (9.4 mmol)을 MC 에 녹인다. Dissolve 15 g (9.4 mmol) of compound -4 in MC in a back bottom flask.
실버트리플루오로 메탄 설포네이트 5.3 g (20.6 mmol) 을 아이소프로필알코올에 녹여서 적가한다. 상온에서 하루 교반 후, 용매를 제거하고 화합물 -5를 얻어 정제
없이 다음 반웅을 진행한다. 5.3 g (20.6 mmol) of silvertrifluoro methane sulfonate are added dropwise by dissolving in isopropyl alcohol. After stirring at room temperature for one day, the solvent was removed and the compound -5 was obtained and purified. Proceed to the next reaction without.
화합물 -6 의 제조 Preparation of Compound-6
등근 바닥 폴라스크에 페닐 보로닉 엑시드 23.5g (192.3 mmol), 메틸 2-클로로 니코티네이트 30 g (174.8 mmol), 테트라키스 (트리페닐포스핀)팔라듐 [Pd(PPh3)4] 6.06 g (5.245 mmol), 포타슘카보네이트 48.31 g (349 mmol)을 THF 600 mL, 증류수 300 mL에 넣고 24시간 동안 가열 환류하였다. 반웅이 완결되면 상온으로 냉각하고 THF 와 증류수를 분리한다 . THF 에 600 mL 의 메탄을을 넣고 결정화 시킨다. 생성된 고형물을 거르고， 물과 메탄을로 씻어주었다. 진공오븐에서 고형물을 건조하여 화합물 -6을 32 g (수율 : 86%) 얻었다. 63.5 g (192.3 mmol) of phenyl boronic acid, 30 g (174.8 mmol) of methyl 2-chloro nicotinate, 6.06 g of tetrakis (triphenylphosphine) palladium [Pd (PPh 3 ) 4 ] 5.245 mmol) and 48.31 g (349 mmol) of potassium carbonate were added to 600 mL of THF and 300 mL of distilled water, followed by heating to reflux for 24 hours. When reaction is complete, cool to room temperature and separate THF and distilled water. 600 mL of methane is added to THF and crystallized. The resulting solids were filtered off and washed with water and methane. The solid was dried in a vacuum oven to obtain 32 g of a compound -6 (yield: 86%).
화합물 -7 의 제조 Preparation of Compound -7
등근 바닥 플라스크에 화합물 -6 32 g (150 mmol) 을 넣고 600 mL 의 무수 THF 로 녹인다 . 0 °C 에서 메틸마그네슴 브로마이드 용액 400 mL 를 플라스크에 적가한다. 반웅 종료 후, 암모늄클로라이드를 물 150 ml 에 녹여서 뒌칭시킨다. 유기 층과 물층을 분리한 다음 용매를 모두 제거한다. 칼럼크로마토그래피를 이용하여 화합물- 7을 28 g (수율 : 87%) 얻었다. Add 32 g (150 mmol) of Compound-6 to the back bottom flask and dissolve in 600 mL of dry THF. 400 mL of methylmagnesium bromide solution is added dropwise to the flask at 0 ° C. After completion of reaction, ammonium chloride was quenched by dissolving in 150 ml of water. The organic and water layers are separated and then all solvent is removed. 28 g (yield: 87%) of compound-7 was obtained by column chromatography.
화합물 -8 의 제조 Preparation of Compound -8
질소 기류하 등근 바닥 플라스크에 MC 용액에 화합물 -7 28 g (131 mmol)을 녹인 후, 보론트리플루오로 다이에틸 이써레이트 16.48 mL (131 mmol)을 적가한다. 하루 교반 후， 소듐 바이 카보네이트를 녹인 물을 넣고 뒌칭시킨다. 반웅 종결 후 유기층을 분리한 다음 용매를 모두 제거한다음 핵산을 이용하여 화합물 -8을 21 g (수율 : 82%) 얻었다. 28 g (131 mmol) of Compound -7 was dissolved in an MC solution in a constant temperature bottom flask under nitrogen stream, followed by dropwise addition of 16.48 mL (131 mmol) of borontrifluoro diethyl etherate. After a day of stirring, the sodium bicarbonate was dissolved in water and quenched. After completion of reaction, the organic layer was separated, and then all solvents were removed. Then, 21 g of a compound -8 was obtained using a nucleic acid (yield: 82%).
화합물 D-1 의 제조 Preparation of Compound D-1
등근 바닥 플라스크에 화합물 -5 5 g (4.8 mmol)과 화합물 -8 2.8 g (14.5 mmol)을 에탄을에 넣고 질소 조건에서 하루 환류 시킨다. 생성된 고형물을 필터한 후 에탄올과 핵산으로 3회 씻어준다. 고형물을 다이클로로메탄에 녹인 후 아이소프로필 알코을로 다시 결정화 시켜서 화합물 D-1을 3 g (수율 : 65%) 얻었다. 5 g (4.8 mmol) of compound -5 and 2.8 g (14.5 mmol) of compound -8 are added to an equipotential bottom flask and refluxed under nitrogen conditions for one day. The resulting solids are filtered and washed three times with ethanol and nucleic acid. The solid was dissolved in dichloromethane and crystallized again with isopropyl alcohol to obtain 3 g of compound D-1 (yield: 65%).
calcd. C56H48IrN3: C, 70.41 ; H, 5.06; Ir, 20.12; N, 4.40; found: C, 70.42; H, 5.1 1 ; N, 4.31 ; calcd. C 56 H 48 IrN 3 : C, 70.41; H, 5.06; Ir, 20.12; N, 4.40; found: C, 70.42; H, 5.1 1; N, 4.31;
제조예 2: D-2 의 제조 Preparation Example 2 Preparation of D-2
[반응식 2]
Scheme 2
화합물 -9 의 제조 Preparation of Compound -9
둥근 바닥 플라스크에 화합물 -8 9.8 g (50 mmol)과 이리듐클로라이드 6 g (20 mmol), 2-에록시에탄올 45 mL, 증류수 15 mL를 넣고 24시간 동안 가열 환류하였다. 반웅이 완결되면 상온으로 넁각하고 반웅중 생긴 고형물을 거르고, 물과 메탄을로 씻어주었다. 진공오븐에서 고형물을 건조하여 화합물 -9를 15 g (수율 : 60%) 얻었다. 9.8 g (50 mmol) of compound -8, 6 g (20 mmol) of iridium chloride, 45 mL of 2-ethoxyethanol and 15 mL of distilled water were added to a round-bottom flask, and the mixture was heated and refluxed for 24 hours. When the reaction was completed, the mixture was cooled to room temperature and the solid formed in the reaction was filtered and washed with water and methane. The solid was dried in a vacuum oven to obtain 15 g (yield: 60%) of compound -9.
화합물 -10 의 제조 Preparation of Compound -10
둥근 바닥 플라스크에 화합물 -9 15 g (12 mmol)을 MC 에 녹인다. Dissolve 15 g (12 mmol) of compound -9 in MC in a round bottom flask.
실버트리플루오로 메탄 설포네이트 6.9 g (26.7 mmol) 을 아이소프로필알코을에 녹여서 적가한다. 상온에서 하루 교반 후, 용매를 제거하고 화합물 -10을 얻어 정제 없이 다음 반웅을 진행한다. 6.9 g (26.7 mmol) of silvertrifluoro methane sulfonate is added dropwise by dissolving in isopropyl alcohol. After a day of stirring at room temperature, the solvent is removed and compound -10 is obtained to proceed the next reaction without purification.
화합물 D-2 의 제조 Preparation of Compound D-2
등근 바닥 플라스크에 화합물 -10 7 g (8.2 mmol)과 화합물 -3 7.05 g (24.7 mmol)을 에탄올에 넣고 질소 조건에서 하루 환류 시킨다. 생성된 고형물을 필터한 후 에탄올과 핵산으로 3회 씻어준다. 고형물을 다이클로로메탄에 녹인 후 아이소프로필 알코을로 다시 결정화 시켜서 화합물 D-2를 4.5 g (수율 : 63%) 얻었다 . calcd. In a back bottom flask, compound -10 7 g (8.2 mmol) and compound -3 7.05 g (24.7 mmol) were added to ethanol and refluxed under nitrogen conditions for one day. The resulting solids are filtered and washed three times with ethanol and nucleic acid. The solid was dissolved in dichloromethane and crystallized again with isopropyl alcohol to obtain 4.5 g of compound D-2 (yield: 63%). calcd.
C49H42lrN3: C, 68.03; H, 4.89; Ir, 22.22; N, 4.86; found: C, 68.02; H, 4.95; N, 4.79; C 49 H 42 lrN 3 : C, 68.03; H, 4.89; Ir, 22.22; N, 4.86; found: C, 68.02; H, 4.95; N, 4.79;
제조예 3: D-3 의 제조 Preparation Example 3 Preparation of D-3
[반응식 3]
Scheme 3
화합물 -1 1 의 제조 Preparation of Compound -1 1
등근 바닥 플라스크에 메틸 5-브로모 -2-클로로피리딘 -3-카르복실레이트 30 g (119.7 mmol), 터셔리 뷰틸 보로닉 엑시드 13.43 g (131.7 mmol), 30 g (119.7 mmol) of methyl 5-bromo-2-chloropyridine-3-carboxylate, 13.43 g (131.7 mmol) of tertiary butyl boronic acid,
테트라키스 (트리페닐포스핀)팔라듐 [Pd(PPh3)4] 4.15 g (3.59 mmol), 포타슘카보네이트
33.1 g (239 mmol)을 THF 600 mL, 증류수 300 mL에 넣고 24시간 동안 가열 환류하였다. 반웅이 완결되면 상온으로 넁각하고 THF 와 증류수를 분리한다. THF 에 600 mL 의 메탄올을 넣고 결정화 시킨다. 생성된 고형물을 거르고, 물과 Tetrakis (triphenylphosphine) palladium [Pd (PPh 3 ) 4 ] 4.15 g (3.59 mmol), potassium carbonate 33.1 g (239 mmol) was added to 600 mL of THF and 300 mL of distilled water and heated to reflux for 24 hours. When the reaction is complete, the solution is cooled to room temperature and the THF and distilled water are separated. 600 mL of methanol is added to THF and crystallized. Filter out the solids,
메탄올로 씻어주었다. 진공오븐에서 고형물을 건조하여 화합물 -11을 20 g (수율 ： 73%) 얻었다. Washed with methanol. The solid was dried in a vacuum oven to obtain 20 g of a compound -11 (yield: 73%).
화합물 -12 의 제조 Preparation of Compound -12
등근 바닥 플라스크에 바이페닐 -3-일 보론산 17.4 g (96.6 mmol), 화합물 -11 20 g (87.8 mmol), 테트라키스 (트리페닐포스핀)팔라듐 [Pd(PPh3)4] 3 g (2.6 mmol), 17.4 g (96.6 mmol) of biphenyl-3-yl boronic acid, 20 g (87.8 mmol) of compound -11, tetrakis (triphenylphosphine) palladium [Pd (PPh 3 ) 4 ] 3 g (2.6 in a back bottom flask mmol),
포타슘카보네이트 24.2 g (175 mmol)을 THF 400 mL, 증류수 200 mL에 넣고 24시간 동안 가열 환류하였다. 반응이 완결되면 상온으로 냉각하고 THF 와 증류수를 분리한다. THF 에 500 mL의 메탄올을 넣고 결정화 시킨다. 생성된 고형물을 거르고, 물과 메탄을로 씻어주었다. 진공오본에서 고형물을 건조하여 화합물 -12를 22 g 24.2 g (175 mmol) of potassium carbonate was added to 400 mL of THF and 200 mL of distilled water and heated to reflux for 24 hours. After the reaction is completed, the reaction mixture is cooled to room temperature, and THF and distilled water are separated. 500 mL of methanol is added to THF for crystallization. The resulting solids were filtered off and washed with water and methane. 22 g of compound -12 was dried by drying in vacuo.
(수율 : 73%) 얻었다. (Yield: 73%) was obtained.
화합물 -13 의 제조 Preparation of Compound -13
등근 바닥 플라스크에 화합물 -12 22 g (63.7 mmol) 을 넣고 400 mL 의 무수 22 g (63.7 mmol) of Compound -12 were added to the bottom flask with 400 mL of anhydrous.
THF 로 녹인다 . 0 °C 에서 메틸마그네슘 브로마이드 용액 169 mL 를 폴라스크에 적가한다. 반웅 종료 후, 암모늄클로라이드를 물 150 ml 에 녹여서 췐칭시킨다. 유기 층과 물층을 분리한 다음 용매를 모두 제거한다. 칼럼크로마토그래피를 이용하여 화합물 -13을 18 g (수율 : 81%) 얻었다. Dissolve in THF. 169 mL of methylmagnesium bromide solution is added dropwise to the polar flask at 0 ° C. After completion of reaction, ammonium chloride was quenched by dissolving in 150 ml of water. The organic and water layers are separated and then all solvent is removed. 18 g (yield: 81%) of compound -13 was obtained by column chromatography.
화합물 -14 의 제조 Preparation of Compound -14
질소 기류하 둥근 바닥 플라스크에 MC 용액에 화합물 -13 18 g (52 mmol)을 녹인 후, 보론트리플루오로 다이에틸 이써레이트 6.54 mL (52 mmol)을 적가한다. 하루 교반 후， 소듐 바이 카보네이트를 녹인 물을 넣고 뒌칭시킨다. 반웅 종결 후 In a round bottom flask under nitrogen stream, 18 g (52 mmol) of Compound -13 was dissolved in MC solution, followed by dropwise addition of 6.54 mL (52 mmol) of borontrifluoro diethyl etherate. After a day of stirring, the sodium bicarbonate was dissolved in water and quenched. After the reaction
유기층을 분리한 다음 용매를 모두 제거한다음 핵산올 이용하여 화합물 -14를 14 g (수율 ： 82%) 얻었다. The organic layer was separated and then the solvent was removed. Then 14 g of a compound -14 was obtained using a nucleic acid (yield: 82%).
화합물 -15 의 제조 Preparation of Compound -15
등근 바닥 플라스크에 화합물 -14 13.7 g (41.8 mmol)과 이리듐클로라이드 5 g (16.7 mmol), 2-에톡시에탄올 120 mL, 증류수 40 mL를 넣고 24시간 동안 가열 12.7 g (41.8 mmol) of compound -14, 5 g (16.7 mmol) of iridium chloride, 120 mL of 2-ethoxyethanol and 40 mL of distilled water were added to the back bottom flask and heated for 24 hours.
환류하였다. 반웅이 완결되면 상온으로 넁각하고 반웅중 생긴 고형물을 거르고, 물과 메탄을로 씻어주었다ᅳ 진공오븐에서 고형물올 건조하여 화합물 -15를 18 g
(수율 : 61%) 얻었다. It was refluxed. When the reaction was completed, the mixture was cooled to room temperature and the solid formed in the reaction was filtered off and washed with water and methane. The solid was dried in a vacuum oven to give 18 g of Compound -15. (Yield 61%) was obtained.
화합물 -16 의 제조 Preparation of Compound -16
등근 바닥 플라스크에 화합물 -15 18 g (10 mmol)을 MC 에 녹인다. Dissolve 18 g (10 mmol) of compound -15 in MC in a back bottom flask.
실버트리플루오로 메탄 설포네이트 5.8 g (22 mmol) 을 아이소프로필알코을에 녹여서 적가한다. 상온에서 하루 교반 후, 용매를 제거하고 화합물 -16을 얻어 정제 없이 다음 반웅을 진행한다. 5.8 g (22 mmol) of silvertrifluoro methane sulfonate is added dropwise by dissolving in isopropyl alcohol. After a day of stirring at room temperature, the solvent is removed and compound -16 is obtained to proceed the next reaction without purification.
화합물 D-3 의 제조 Preparation of Compound D-3
등근 바닥 플라스크에 화합물 -16 7.1 g (6.3 mmol)과 화합물 -8 3.7 g (19.1 mmol)을 에탄올에 넣고 질소 조건에서 하루 환류 시킨다. 생성된 고형물을 필터한 후 에탄올과 핵산으로 3회 씻어준다. 고형물을 다이클로로메탄에 녹인 후 7.1 g (6.3 mmol) of Compound -16 and 3.7 g (19.1 mmol) of Compound -8 are added to an ethanol bottom flask and refluxed under nitrogen conditions for one day. The resulting solids are filtered and washed three times with ethanol and nucleic acid. After dissolving the solid in dichloromethane
아이소프로필 알코을로 다시 결정화 시켜서 화합물 D-3을 5 g (수율 : 45%) 얻었다. calcd. C62H60IrN3: C, 71.65; H, 5.82; Ir, 18.49; N, 4.04; found: C, 71.62; H, 5.85; N, 4.01 ; 제조예 4: D-4 의 제조Crystallization again with isopropyl alcohol gave 5 g (yield: 45%) of compound D-3. calcd. C 62 H 60 IrN 3 : C, 71.65; H, 5. 82; Ir, 18.49; N, 4.04; found: C, 71.62; H, 5.85; N, 4.01; Preparation Example 4 Preparation of D-4
반웅식 4] Banungsik 4]
화합물 D-4 의 제조 Preparation of Compound D-4
등근 바닥 플라스크에 화합물 -10 8 g (9.4 mmol)과 화합물 -14 9.2 g (28 mmol)을 에탄을에 넣고 질소 조건에서 하루 환류 시킨다. 생성된 고형물을 필터한 후 에탄을과 핵산으로 3회 씻어준다. 고형물을 다이클로로메탄에 녹인 후 아이소프로필 알코을로 다시 결정화 시켜서 화합물 D-4를 4.5 g (수율 ： 53%) 얻었다 . calcd. In a back bottom flask, compound -10 8 g (9.4 mmol) and compound -14 9.2 g (28 mmol) are added to ethane and refluxed under nitrogen conditions for one day. The resulting solids were filtered and washed three times with ethane and nucleic acid. The solid was dissolved in dichloromethane and crystallized again with isopropyl alcohol to obtain 4.5 g (yield: 53%) of compound D- 4 . calcd.
C52H48IrN3: C, 68.85; H, 5.33; Ir, 21.19; N, 4.63; found: C, 68.82; H, 5.25; N, 4.70; C 52 H 48 IrN 3 : C, 68.85; H, 5. 33; Ir, 21.19; N, 4.63; found: C, 68.82; H, 5. 25; N, 4.70;
제조예 5: D-5 의 제조 Preparation Example 5 Preparation of D-5
[반웅식 5]
[Bungungsik 5]
화합물 -17 의 제조 Preparation of Compound -17
등근 바닥 플라스크에 바이페닐 -3-일 보론산 35.2 g (177.7 mmol), 메틸 2- 클로로 -4-메틸니코티네이트 30 g (161.6 mmol), 테트라키스 (트리페닐포스핀)팔라듐 [Pd(PPh3)4] 5.6 g (4.85 mmol), 포타슘카보네이트 44.67 g (323 mmol)을 THF 600 mL, 증류수 300 mL에 넣고 24시간 동안 가열 환류하였다. 반응이 완결되면 상온으로 넁각하고 THF 와 증류수를 분리한다 THF 에 600 mL 의 메탄을을 넣고 결정화 시킨다. 생성된 고형물올 거르고, 물과 메탄을로 씻어주었다. 진공오븐에서 고형물을
건조하여 화합물 -17을 40 g (수율 : 81%) 얻었다. 35.2 g (177.7 mmol) of biphenyl-3-yl boronic acid, 30 g (161.6 mmol) of methyl 2-chloro-4-methylnicotinate, tetrakis (triphenylphosphine) palladium [Pd (PPh) 3 ) 4 ] 5.6 g (4.85 mmol) and 44.67 g (323 mmol) of potassium carbonate were added to 600 mL of THF and 300 mL of distilled water, followed by heating to reflux for 24 hours. When the reaction is completed, the solution is cooled to room temperature, and THF and distilled water are separated. 600 mL of methane is added to THF and crystallized. The resulting solids were filtered off and washed with water and methane. Solids in a vacuum oven It dried and obtained 40g (yield: 81%) of compound-17.
화합물 -18 의 제조 Preparation of Compound -18
등근 바닥 플라스크에 화합물 -17 40 g (132 mmol) 을 넣고 800 mL 의 무수 THF 로 녹인다 . 0 °C 에서 메틸마그네슘 브로마이드 용액 351 mL 를 플라스크에 적가한다. 반웅 종료 후, 암모늄클로라이드를 물 200 ml 에 녹여서 뒌칭시킨다. 유기 층과 물층을 분리한 다음 용매를 모두 제거한다. 칼럼크로마토그래피를 이용하여 화합물 -18을 34 g (수율 ： 85%) 얻었다. Add 40 g (132 mmol) of Compound-17 to the back bottom flask and dissolve in 800 mL of dry THF. 351 mL of methylmagnesium bromide solution is added dropwise to the flask at 0 ° C. After completion of reaction, ammonium chloride was quenched by dissolving in 200 ml of water. The organic and water layers are separated and then all solvent is removed. 34 g (yield: 85%) of compound -18 was obtained using column chromatography.
화합물 -19 의 제조 Preparation of Compound -19
질소 기류하 등근 바닥 플라스크에 MC 용액에 화합물 -18 34 g (1 12 mmol)을 녹인 후， 보론트리플루오로 다이에틸 이써레이트 14 mL (1 12 mmol)을 적가한다. 하루 교반 후， 소듐 바이 카보네이트를 녹인 물을 넣고 뒌칭시킨다. 반웅 종결 후 유기층을 분리한 다음 용매를 모두 제거한다음 핵산을 이용하여 화합물 -19를 35 g (수율 ： 80%) 얻었다. After dissolving 34 g (1 12 mmol) of compound -18 in MC solution in a back-bottomed flask under nitrogen stream, 14 mL (1 12 mmol) of borontrifluoro diethyl etherate are added dropwise. After a day of stirring, the sodium bicarbonate was dissolved in water and quenched. After completion of reaction, the organic layer was separated, and then all solvents were removed. Then, 35 g of a compound -19 was obtained using a nucleic acid (yield: 80%).
화합물 -20 의 제조 Preparation of Compound -20
등근 바닥 플라스크에 화합물 -19 19.1 g (66.9 mmol)과 이리듐클로라이드 8 g 19.1 g (66.9 mmol) of Compound -19 and 8 g of iridium chloride in a back bottom flask
(26.7 mmol), 2-에톡시에탄을 90 mL, 증류수 30 mL를 넣고 24시간 동안 가열 환류하였다. 반웅이 완결되면 상온으로 넁각하고 반웅중 생긴 고형물을 거르고, 물과 메탄올로 씻어주었다. 진공오븐에서 고형물을 건조하여 화합물 -20을 30 g (26.7 mmol), 90 mL of 2-ethoxyethane and 30 mL of distilled water were added thereto, and the mixture was heated to reflux for 24 hours. When the reaction was completed, the mixture was cooled to room temperature and the solid formed in the reaction was filtered and washed with water and methanol. 30 g of compound -20 was dried by drying the solid in a vacuum oven.
(수율 ： 70%) 얻었다. (Yield: 70%) was obtained.
화합물 -21 의 제조 Preparation of Compound -21
등근 바닥 플라스크에 화합물 -20 30 g (18.8 mmol)을 MC 에 녹인다. Dissolve 30 g (18.8 mmol) of compound -20 in MC in a back bottom flask.
실버트리플루오로 메탄 설포네이트 10.6 g (41.3 mmol) 을 아이소프로필알코을에 녹여서 적가한다. 상온에서 하루 교반 후, 용매를 제거하고 화합물 -21을 얻어 정제 없이 다음 반응을 진행한다. 10.6 g (41.3 mmol) of silvertrifluoro methane sulfonate is added dropwise by dissolving in isopropyl alcohol. After a day of stirring at room temperature, the solvent was removed and compound -21 was obtained to proceed to the next reaction without purification.
화합물 D-5 의 제조 Preparation of Compound D-5
등근 바닥 플라스크에 화합물 -21 12 g (11.6 mmol)과 화합물 -8 6.8 g (34.9 mmol)을 에탄을에 넣고 질소 조건에서 하루 환류 시킨다. 생성된 고형물을 필터한 후 에탄을과 헥산으로 3회 씻어준다. 고형물을 다이클로로메탄에 녹인 후 12 g (11.6 mmol) of Compound -21 and 6.8 g (34.9 mmol) of Compound -8 are added to an equipotential bottom flask and refluxed under nitrogen conditions for one day. The resulting solids were filtered and washed three times with ethane and hexane. After dissolving the solid in dichloromethane
아이소프로필 알코을로 다시 결정화 시켜서 화합물 D-5를 5 g (수율 : 44%) 얻었다. calcd. C56H48IrN3: C, 70.41 ; H, 5.06; Ir, 20.12; N, 4.40; found: C, 70.35; H, 5.10; N, 4.35;
제조예 6: D-6 의 제조 Crystallization again with isopropyl alcohol gave 5 g (yield: 44%) of compound D-5. calcd. C 56 H 48 IrN 3 : C, 70.41; H, 5.06; Ir, 20.12; N, 4.40; found: C, 70.35; H, 5. 10; N, 4.35; Preparation Example 6 Preparation of D-6
6] 6]
화합물 D-6 의 제조 Preparation of Compound D-6
등근 바닥 플라스크에 화합물 -10 8 g (9.4 mmol)과 화합물 -19 8.1 g (28.2 mmol)을 에탄을에 넣고 질소 조건에서 하루 환류 시킨다. 생성된 고형물을 필터한 후 에탄을과 핵산으로 3회 씻어준다. 고형물을 다이클로로메탄에 녹인 후 아이소프로필 알코올로 다시 결정화 시켜서 화합물 D-6을 4.5 g (수율 : 56%) 얻었다 . calcd. In a back bottom flask, compound -10 8 g (9.4 mmol) and compound -19 8.1 g (28.2 mmol) are added to ethane and refluxed under nitrogen conditions for one day. The resulting solids were filtered and washed three times with ethane and nucleic acid. The solid was dissolved in dichloromethane and crystallized again with isopropyl alcohol to obtain 4.5 g (yield: 5 6%) of compound D-6. calcd.
C49H42IrN3: C, 68.03; H, 4.89; Ir, 22.22; N, 4.86; found: C, 68.02; H, 4.95; N, 4.75; C 49 H 42 IrN 3 : C, 68.03; H, 4.89; Ir, 22.22; N, 4.86; found: C, 68.02; H, 4.95; N, 4.75;
(유기발광소자의 제조) (Manufacture of organic light emitting device)
비교예 1 Comparative Example 1
ITO(Indium tin oxide)가 1500 A의 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면 이소프로필 알코을, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 이송시킨 다음 산소 플라즈마를 이용하여 상기 기판을 5분간 세정한 후 진공 층착기로 기판을 이송하였다. 이렇게 준비된 ΠΌ 투명 전극을 양극으로 사용하여 ΠΌ 기판 상부에 하기 화학식 Z-1으로 표시되는 HTM(a-NPD(4,4'-bis[N-(l-napthyl)-N-phenyl-ammo] biphenyl) 을 진공 증착하여 정공 수송층을 형성하였다. The glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 A was washed by distilled water ultrasonically. After the distilled water was washed, isopropyl alcohol was ultrasonically cleaned with a solvent such as acetone and methanol, dried, and then transferred to a plasma cleaner. HTM (a-NPD (4,4'-bis [N- (l-napthyl) -N-phenyl-ammo] biphenyl) represented by the following Chemical Formula Z-1 on the ΠΌ substrate using the prepared ΠΌ transparent electrode as the anode ) Was vacuum deposited to form a hole transport layer.
[화학식 Z-1] [Formula Z-1]
[화학식 Z-2]
[Formula Z-2]
상기 정공 수송층 상부에 화학식 Z-2로 표시되는 CDBP를 호스트로 사용하고 파란색 (blue)의 인광 도판트로 하기 화학식 Z-3로 표시되는 Fir6(iridium(III)bis(4,6- difluorophenylpyridinato)tetrakis(l-pyrazolyl)borate)¾- 10 중량0 /o로 도핑하여 진공 증착하여 300 A 두께의 발광층올 형성하였다. Fir6 (iridium (III) bis (4,6-difluorophenylpyridinato) tetrakis (II) represented by the following Chemical Formula Z-3 using a CDBP represented by Chemical Formula Z-2 as a host and a blue phosphorescent dopant on the hole transport layer. l-pyrazolyl) borate) ¾-10 was doped with a weight of 0 / o and vacuum deposition to form a light emitting layer of 300 A thickness.
Z-3] Z-3]
그 후 상기 발광층 상부에 하기 화학식 Z-4으로 표시되는 BAlq (bis(2-methyl- 8-quinolinolato-Nl,08)-(l, r-Biphenyl-4-olato)aluminum)) 50 A 및 하기 화학식 Z-5로 표시되는 Alq3 (tris(8-hydroxyquinolinato)aluminium) 250 A를 순차적으로 적층하여 전자수송층을 형성하였다. 상기 전자수송층 상부에 LiF 5 A과 A1 1000 A을 순차적으로 진공 증착하여 음극올 형성함으로써 유기발광소자를 제조하였다. Subsequently, BAlq (bis (2-methyl-8-quinolinolato-Nl, 08)-(l, r-Biphenyl-4-olato) aluminum)) 50 A represented by the following Chemical Formula Z-4 was formed on the emission layer. Alq3 (tris (8-hydroxyquinolinato) aluminium) 250 A represented by Z-5 was sequentially stacked to form an electron transport layer. An organic light emitting diode was manufactured by sequentially depositing LiF 5 A and A1 1000 A on the electron transport layer to form a cathode.
-4] -4 ]
비교예 2 Comparative Example 2
비교예 1에서, 도판트를 [화학식 Z-3] 대신 [화학식 T-1]을사용한 것을 제외하고는 비교예 1과 동일한 방법으로 제조하여 비교예 2 소자를 제조하였다.
화학식 T-l] In Comparative Example 1, a dopant was manufactured in the same manner as in Comparative Example 1 except that [Formula T-1] was used instead of [Formula Z-3] to prepare a Comparative Example 2 device. Formula Tl]
비교예 3 Comparative Example 3
비교예 1에서, 도판트를 [화학식 Ζ-3] 대신 [화학식 Τ-2]를 사용한 것을 제외하고는 비교예 1과 동일한 방법으로 제조하여 비교예 3 소자를 제조하였다. In Comparative Example 1, a dopant was manufactured in the same manner as in Comparative Example 1, except that [Formula Τ-2] was used instead of [Formula VII-3] to prepare a Comparative Example 3 device.
τ_2] τ_2]
실시예 1 Example 1
청색 (Blue)의 인광 도판트로 상기 화학식 Z-3으로 표시되는 Fir6 대신에， 상기 제조예 1에서 제조한 화합물 D-1을 사용하여 10 중량 % 도핑한 점을 제외하고는 비교예 1과 동일한 방법으로 유기발광소자를 제작하였다. The same method as in Comparative Example 1 except for doping with 10 wt% of Compound D-1 prepared in Preparation Example 1 instead of Fir6 represented by Chemical Formula Z-3 as a blue phosphorescent dopant. An organic light emitting device was manufactured.
실시예 2 Example 2
제조예 1에 따른 도펀트 대신에 제조예 2에 따른 도편트를 이용한 점을 제외하고는 상기 실시예 1과 동일한 방법으로 유기발광소자를 제조하였다. An organic light emitting diode was manufactured according to the same method as Example 1 except for using the dopant according to Preparation Example 2 instead of the dopant according to Preparation Example 1.
실시예 3 Example 3
제조예 3에 따른 도편트를 이용한 점을 제외하고는 상기 실시예 1과 동일한 방법으로 유기발광소자를 제조하였다. An organic light emitting diode was manufactured according to the same method as Example 1 except for using the dopant according to Preparation Example 3.
실시예 4 - 제조예 4에 따른 도편트를 이용한 점을 제외하고는 상기 실시예 1과 동일한 방법으로 유기발광소자를 제조하였다. Example 4 An organic light emitting diode was manufactured according to the same method as Example 1 except for using the dopant according to Preparation Example 4.
실시예 5 Example 5
제조예 5에 따른 도편트를 이용한 점을 제외하고는 상기 실시예 1과 동일한 방법으로 유기발광소자를 제조하였다. An organic light emitting diode was manufactured according to the same method as Example 1 except for using the dopant according to Preparation Example 5.
실시예 6
제조예 6에 따른 도펀트를 이용한 점을 제외하고는 상기 실시예 1과 동일한 방법으로 유기발광소자를 제조하였다. Example 6 An organic light emitting diode was manufactured according to the same method as Example 1 except for using the dopant according to Preparation Example 6.
(유기발광소자의 성능 측정) (Performance Measurement of Organic Light Emitting Diode)
상기 실시예 1 내지 6과 비교예 1 내지 3에서 제조된 각각의 유기발광소자에 대하여 전압에 따른 전류밀도 변화， 휘도변화를 측정하여 이를 통해 발광효율을 평가하였고, 또한 수명 특성을 평가하였다. 구체적인 측정방법은 다음과 같고, 그 결과는 하기 표 1에 나타내었다. For each of the organic light emitting diodes manufactured in Examples 1 to 6 and Comparative Examples 1 to 3, the current density change and the luminance change according to voltage were measured, and thus, the luminous efficiency was evaluated, and the lifespan characteristics were evaluated. Specific measurement methods are as follows, and the results are shown in Table 1 below.
(1) 전압변화에 따른 전류밀도의 변화 측정 (1) Measurement of change in current density according to voltage change
제조된 유기발광소자에 대해, 전압을 0 V 부터 10 V까지 상승시키면서 전류- 전압계 (Keithley 2400)를 이용하여 단위소자에 흐르는 전류값을 측정하고, 측정된 전류값을 면적으로 나누어 결과를 얻었다. For the organic light emitting device manufactured, the current value flowing through the unit device was measured by using a current-voltmeter (Keithley 2400) while increasing the voltage from 0 V to 10 V, and the measured current value was divided by the area to obtain a result.
(2) 전압변화에 따른 휘도변화 측정 (2) Measurement of luminance change according to voltage change
제조된 유기발광소자에 대해, 전압을 0 V 부터 10 V까지 상승시키면서 휘도계 (Minolta Cs-I OOOA)를 이용하여 그 때의 휘도를 측정하여 결과를 얻었다. The resulting organic light emitting device was measured using a luminance meter (Minolta Cs-I OOOA) while increasing the voltage from 0 V to 10 V to obtain a result.
(3) 발광효율 측정 (3) Measurement of luminous efficiency
상기 (1) 및 (2)로부터 측정된 휘도와 전류밀도 및 전압을 이용하여 동일 밝기 (9000 cd/m2)의 전류 효율 (cd/A)을 계산하였다. The current efficiency (cd / A) of the same brightness (9000 cd / m 2 ) was calculated using the brightness, current density, and voltage measured from (1) and (2).
(4) 수명 평가 (4) life assessment
수명은 3% 발광효율이 감소할 때까지의 시간을 측정한 것으로 비교 예를 100%로 하여 본 발명에서 제공된 재료들의 수명을 상대적으로 나타내었다. The lifetime was measured by measuring the time until the luminous efficiency decreased by 3%, and the life of the materials provided in the present invention was relatively shown with the comparative example as 100%.
[표 1] TABLE 1
구분 화학식 발광효율 (cd/A) 소자 수명 (h) Category Chemical Emission Efficiency (cd / A) Device Lifetime (h)
T50(%) at l O mA/cm2 비교예 1 Z-3 6.1 1 T50 (%) at l O mA / cm 2 Comparative Example 1 Z-3 6.1 1
비교예 2 T-1 5.4 100 Comparative Example 2 T-1 5.4 100
비교예 3 T-2 5.1 55 Comparative Example 3 T-2 5.1 55
실시예 1 D-1 10.5 98 Example 1 D-1 10.5 98
실시예 2 D-2 9.8 105 Example 2 D-2 9.8 105
실시예 3 D-3 11.6 1 1 1
실시예 4 D-4 8.7 125 실시예 5 D-5 9.9 107 실시예 6 D-6 10.7 99 상기 표 1에 나타난 바와 같이, 본 발명에서 제공된 재료를 사용하여 제작한 소자의 경우 발광 효율 또는 수명이 훨씬 더 우수하다는 것을 알 수 있다. 이는 본 발명에서 제조된 화합물이 양호한 유기발광소자용 재료로 사용될 수 있는 가능성을 보여준다. Example 3 D-3 11.6 1 1 1 Example 4 D-4 8.7 125 Example 5 D-5 9.9 107 Example 6 D-6 10.7 99 As shown in Table 1, in the case of a device fabricated using the material provided in the present invention, luminous efficiency or lifespan You can see that it is much better. This shows the possibility that the compound prepared in the present invention can be used as a material for a good organic light emitting device.
본 발명은 상기 실시예들에 한정되는 것이 아니라 서로 다른 다양한 형태로 제조될 수 있으며, 본 발명이 속하는 기술분야에서 통상의 지식을 가진 자는 본 발명의 기술적 사상이나 필수적인 특징올 변경하지 않고서 다른 구체적인 형태로 실시될 수 있다는 것을 이해할 수 있을 것이다. 그러므로 이상에서 기술한 실시예들은 모든 면에서 예시적인 것이며 한정적이 아닌 것으로 이해해야만 한다.
The present invention is not limited to the above embodiments, but may be manufactured in various forms, and a person skilled in the art to which the present invention pertains has no specific form without changing the technical spirit or essential features of the present invention. It will be appreciated that the present invention may be practiced as. Therefore, it should be understood that the embodiments described above are exemplary in all respects and not restrictive.
Claims
【청구의 범위】 【Scope of Claim】
【청구항 11 【Claim 11
하기 화학식 1로 표시되는 화합물: Compound represented by Formula 1:
상기 화학식 1에서, In Formula 1,
R1 내지 R6은 각각 독립적으로 수소, 중수소, 할로겐기, 시아노기, 치환 또는 비치환된 C1 내지 C20 알킬기, 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 실릴기이고, R 1 to R 6 are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted silyl group,
여기서 R1 내지 R3 중 어느 하나는 치환 또는 비치환된 C6 내지 C30 아릴기이고, Here, any one of R 1 to R 3 is a substituted or unsubstituted C6 to C30 aryl group,
R4 내지 R6 중 어느 하나는 치환 또는 비치환된 C1 내지 C4 알킬기, 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 실릴기이고, Any one of R 4 to R 6 is a substituted or unsubstituted C1 to C4 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted silyl group,
X1 및 X2는 각각 독립적으로， 0, S, SO, S02, POR7, NR8, CR9R10, 또는 X 1 and X 2 are each independently 0, S, SO, S0 2 , POR 7 , NR 8 , CR 9 R 10 , or
SiR^R12이고， SiR^R is 12 ,
여기서 R7 내지 R12은 각각 독립적으로, 수소, 중수소， 치환 또는 비치환된 C1 내지 C30 알킬기， 치환 또는 비치환된 C3 내지 C30 사이클로알킬기, 치환 또는 비치환된 C3 내지 C30 헤테로사이클로알킬기， 치환 또는 비치환된 C6 내지 C30 아릴기, 치환 또는 비치환된 C2 내지 C30 해테로아릴기， 치환 또는 비치환된 아민기 치환 또는 비치환된 C6 내지 C30 아릴아민기, 치환 또는 비치환된 C6 내지 C30 헤테로아릴아민기, 치환 또는 비치환된 C1 내지 C30 알콕시기, 치환 또는 비치환된 C2 내지 C30 알콕시카르보닐기, 치환 또는 비치환된 C2 내지 C30 Here, R 7 to R 12 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 heterocycloalkyl group, substituted or Unsubstituted C6 to C30 aryl group, substituted or unsubstituted C2 to C30 heteroaryl group, substituted or unsubstituted amine group, substituted or unsubstituted C6 to C30 arylamine group, substituted or unsubstituted C6 to C30 hetero Arylamine group, substituted or unsubstituted C1 to C30 alkoxy group, substituted or unsubstituted C2 to C30 alkoxycarbonyl group, substituted or unsubstituted C2 to C30
알콕시카르보닐아미노기, 치환 또는 비치환된 C7 내지 C30 Alkoxycarbonylamino group, substituted or unsubstituted C7 to C30
아릴옥시카르보닐아미노기, 치환 또는 비치환된 C1 내지 C30 술파모일아미노기,
치환 또는 비치환된 C2 내지 C30 알케닐기, 치환 또는 비치환된 C2 내지 C30 알키닐기, 치환 또는 비치환된 실릴기, 치환 또는 비치환된 실릴옥시기, 치환 또는 비치환된 C1 내지 C30 아실기, 치환 또는 비치환된 C1 내지 C20 아실옥시기, 치환 또는 비치환된 C1 내지 C20 아실아미노기, 치환 또는 비치환된 C1 내지 C30 술포닐기, 치환 또는 비치환된 C1 내지 C30 알킬티올기, 치환 또는 비치환된 C1 내지 C30 헤테로사이클로티올기, 치환 또는 비치환된 C6 내지 C30 아릴티을기, 치환 또는 비치환된 C1 내지 C30 헤테로아릴티올기， 치환 또는 비치환된 C1 내지 C30 우레이드기, 할로겐기, 할로겐 함유기, 시아노기， 히드특실기, 아미노기, 니트로기, 카르복실기, 페로세닐기 또는 이들의 조합이거나 Aryloxycarbonylamino group, substituted or unsubstituted C1 to C30 sulfamoylamino group, Substituted or unsubstituted C2 to C30 alkenyl group, substituted or unsubstituted C2 to C30 alkynyl group, substituted or unsubstituted silyl group, substituted or unsubstituted silyloxy group, substituted or unsubstituted C1 to C30 acyl group, Substituted or unsubstituted C1 to C20 acyloxy group, substituted or unsubstituted C1 to C20 acylamino group, substituted or unsubstituted C1 to C30 sulfonyl group, substituted or unsubstituted C1 to C30 alkylthiol group, substituted or unsubstituted C1 to C30 heterocyclothiol group, substituted or unsubstituted C6 to C30 arylthiol group, substituted or unsubstituted C1 to C30 heteroarylthiol group, substituted or unsubstituted C1 to C30 ureide group, halogen group, halogen It is a containing group, a cyano group, a hydroxyl group, an amino group, a nitro group, a carboxyl group, a ferrocenyl group, or a combination thereof.
R9 및 R10, 또는 R1 1 및 R12이 융합하여 고리를 형성하고, R 9 and R 10 , or R 1 1 and R 12 are fused to form a ring,
M은 Ir, Os, Pt, Pb, Re, Ru, 또는 Pd이고， M is Ir, Os, Pt, Pb, Re, Ru, or Pd,
n및 m은 각각 독립적으로 1 또는 2의 정수 중 어느 하나이고, n + m은 3의 정수이다. . n and m are each independently an integer of 1 or 2, and n + m is an integer of 3. .
【청구항 2】 【Claim 2】
제 1항에 있어서, According to clause 1,
상기 R1 내지 R3 중 어느 하나는 치환 또는 비치환된 C6 내지 C10 아릴기인 화합물. A compound wherein any one of R 1 to R 3 is a substituted or unsubstituted C6 to C10 aryl group.
【청구항 3】 【Claim 3】
제 1항에 있어서, According to clause 1,
상기 R1 내지 R3 중 어느 하나는 치환 또는 비치환된 페닐기인 화합물. A compound wherein any one of R 1 to R 3 is a substituted or unsubstituted phenyl group.
【청구항 4】 【Claim 4】
제 1항에 있어서, According to clause 1,
상기 R4 내지 R6 중 어느 하나는 치환 또는 비치환된 메틸기, 치환 또는 비치환된 에틸기, 치환 또는 비치환된 프로필기, 치환 또는 비치환된 부틸기, 치환 또는 비치환된 실릴기， 또는 치환 또는 비치환된 페닐기인 화합물. Any one of R 4 to R 6 is a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted silyl group, or a substituted Or a compound that is an unsubstituted phenyl group.
【청구항 5】 【Claim 5】
제 4항에 있어서, According to clause 4,
상기 R4 내지 R6 중 어느 하나는 비치환된 메틸기, 비치환된 에틸기, 이소프로필기, t-부틸기, 트리메틸실릴기， 또는 비치환된 페닐기인 화합물. A compound in which any one of R 4 to R 6 is an unsubstituted methyl group, unsubstituted ethyl group, isopropyl group, t-butyl group, trimethylsilyl group, or unsubstituted phenyl group.
【청구항 6】
제 1항에 있어서, 【Claim 6】 According to clause 1,
상기 X1 및 X2는 각각 독립적으로 , 0, S, POR7, NR8, CR9R10, 또는 SiR^R12이고 여기서 R7 내지 R12는 각각 독립적으로 C1 내지 C4 알킬기인 화합물. Wherein X 1 and _ _ _ _ _
【청구항 7] [Claim 7]
제 1항에 있어서, According to clause 1,
상기 R1 내지 R3 중 어느 하나는 치환 또는 비치환된 페닐기이고， 상기 R4 내지 R6 중 어느 하나는 비치환된 메틸기, 비치환된 에틸기, 이소프로필기, t-부틸기, 트리메틸실릴기, 또는 비치환된 페닐기이고, Any one of R 1 to R 3 is a substituted or unsubstituted phenyl group, and any one of R 4 to R 6 is an unsubstituted methyl group, unsubstituted ethyl group, isopropyl group, t-butyl group, or trimethylsilyl group. , or an unsubstituted phenyl group,
상기 X1 및 X2는 각각 독립적으로, CR9R10이고, X 1 and X 2 are each independently CR 9 R 10 ,
여기서, R9 및 R10은 각각 독립적으로 C1 내지 C4 알킬기인 화합물. Here, R 9 and R 10 are each independently a C1 to C4 alkyl group.
【청구항 8] [Claim 8]
제 7항에 있어서， In clause 7,
상기 R1은 비치환된 페닐기이고, Wherein R 1 is an unsubstituted phenyl group,
상기 R5은 비치환된 메틸기, 비치환된 에틸기， 이소프로필기, t-부틸기， 또는 트리메틸실릴기이고, R 5 is an unsubstituted methyl group, unsubstituted ethyl group, isopropyl group, t-butyl group, or trimethylsilyl group,
상기 R9 및 R10은 각각 독립적으로 메틸기인 화합물. A compound wherein R 9 and R 10 are each independently a methyl group.
【청구항 9】 【Claim 9】
제 1항에 있어서, According to clause 1,
상기 화학식 1은 하기 그룹 I에 나열된 화합물 중 하나인 화합물. A compound of Formula 1 above is one of the compounds listed in Group I below.
[그룹 I]
[Group I]
【청구항 10】 【Claim 10】
서로 마주하는 양극과 음극， 및 Anode and cathode facing each other, and
상기 양극과 상기 음극 사이에 위치하는 적어도 한 층의 유기층을 포함하고 상기 유기층은 제 1항 내지 제 9항 중 어느 한 항에 따른 화합물을 포함하는 유기광전자소자. An organic optoelectronic device comprising at least one organic layer located between the anode and the cathode, wherein the organic layer includes the compound according to any one of claims 1 to 9.
【청구항 1 1】 ' 【Claim 1 1】 '
제 10항에 있어서, According to clause 10,
상기 유기층은 발광층을 포함하고, The organic layer includes a light emitting layer,
상기 발광층은 상기 화합물을 포함하는 유기광전자소자. The light-emitting layer is an organic optoelectronic device containing the compound.
【청구항 12] [Claim 12]
제 1 1항에 있어서, According to clause 11,
상기 화합물은 상기 발광층의 도판트로서 포함되는 유기광전자소자. The compound is an organic optoelectronic device included as a dopant in the light-emitting layer.
【청구항 13】 【Claim 13】
제 10항에 따른 유기광전자소자를 포함하는 표시 장치.
A display device including the organic optoelectronic device according to claim 10.
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| KR10-2013-0120120 | 2013-10-08 | ||
| KR1020130120120A KR101599965B1 (en) | 2013-10-08 | 2013-10-08 | Compound, organic optoelectric device and display device |
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| PCT/KR2014/006116 WO2015053463A1 (en) | 2013-10-08 | 2014-07-08 | Compound, organic optoelectric diode including same, and display device |
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| KR101599965B1 (en) | 2016-03-04 |
| KR20150041506A (en) | 2015-04-16 |
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