RU2602236C1 - Bis(2-phenylpyridinato-n,c2'){2-[2'-(4-alkylbenzole sulphonamido)phenyl]benzoxazolato-n,n'}iridium(iii) and electroluminescent device based thereon - Google Patents
Bis(2-phenylpyridinato-n,c2'){2-[2'-(4-alkylbenzole sulphonamido)phenyl]benzoxazolato-n,n'}iridium(iii) and electroluminescent device based thereon Download PDFInfo
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims abstract description 9
- -1 sulphonamido Chemical group 0.000 title claims abstract description 9
- 229910052741 iridium Inorganic materials 0.000 title abstract description 14
- 239000000126 substance Substances 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 238000002347 injection Methods 0.000 claims description 7
- 239000007924 injection Substances 0.000 claims description 7
- 230000005525 hole transport Effects 0.000 claims description 4
- 230000000903 blocking effect Effects 0.000 claims description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 abstract description 13
- 150000001875 compounds Chemical class 0.000 abstract description 9
- 239000013522 chelant Substances 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 2
- 230000003595 spectral effect Effects 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 5
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 4
- 238000004020 luminiscence type Methods 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XKFNOBGOFBCSSQ-UHFFFAOYSA-N N-[2-(1,3-benzoxazol-2-yl)phenyl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=CC=CC=C1C1=NC2=CC=CC=C2O1 XKFNOBGOFBCSSQ-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 150000000183 1,3-benzoxazoles Chemical class 0.000 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 150000002503 iridium Chemical class 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000011269 tar Substances 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ADALGBTXGIISDM-UHFFFAOYSA-N 2-[(4-methylphenyl)sulfonylamino]benzoic acid Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=CC=CC=C1C(O)=O ADALGBTXGIISDM-UHFFFAOYSA-N 0.000 description 1
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- KDOQMLIRFUVJNT-UHFFFAOYSA-N 4-n-naphthalen-2-yl-1-n,1-n-bis[4-(n-naphthalen-2-ylanilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=C2C=CC=CC2=CC=1)C1=CC=C(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=C1 KDOQMLIRFUVJNT-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000005595 acetylacetonate group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 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
- 238000012512 characterization method Methods 0.000 description 1
- 150000004697 chelate complex Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 230000001815 facial effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- LNJXVUXPFZKMNF-UHFFFAOYSA-K iridium(3+);trichloride;trihydrate Chemical compound O.O.O.Cl[Ir](Cl)Cl LNJXVUXPFZKMNF-UHFFFAOYSA-K 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical class [H]C([H])([H])* 0.000 description 1
- 238000005424 photoluminescence Methods 0.000 description 1
- VVOPUZNLRVJDJQ-UHFFFAOYSA-N phthalocyanine copper Chemical compound [Cu].C12=CC=CC=C2C(N=C2NC(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2N1 VVOPUZNLRVJDJQ-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
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- 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
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- 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
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
- H05B33/145—Arrangements of the electroluminescent material
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- 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
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
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- H10K2102/301—Details of OLEDs
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Abstract
Description
Изобретение относится к новым соединениям в ряду хелатных комплексов иридия, а именно к бис(2-фенилпиридинато-N,C2′){2-[2′-(4-алкилбензолсульфонамидо)фенил]бензоксазолато-N,N′}иридия(III) общей формулы I,The invention relates to new compounds in the series of chelate complexes of iridium, namely to bis (2-phenylpyridinato-N, C 2 ′ ) {2- [2 ′ - (4-alkylbenzenesulfonamido) phenyl] benzoxazolato-N, N ′} iridium (III ) of the general formula I,
где R= алкил (C1-C6), проявляющему электролюминесцентные свойства, и электролюминесцентным устройствам (органическим светоизлучающим диодам, известных как ОСИД или OLED - Organic Light Emitting Diodes, - которые используются в качестве эффективных и высокоэкономичных твердотельных источников освещения нового поколения) с использованием в них вышеуказанного соединения в качестве активного люминесцентного слоя.where R = alkyl (C 1 -C 6 ), exhibiting electroluminescent properties, and electroluminescent devices (organic light emitting diodes, known as OLEDs or OLED - Organic Light Emitting Diodes - which are used as efficient and highly economical solid state lighting sources of a new generation) with using the above compound as an active luminescent layer.
Известны электролюминесцентные устройства на основе хелатных комплексов иридия - замещенные по фенильному и пиридиновому кольцам трис(2-фенилпиридинато-N,C2′)иридия(III) (Jung S.-O., Kang Y., Kim H.-S., Kim Y.-H., Lee C.-L., Kim J.-J., Lee S.-K., Kwon S.-K. Effect of substitution of methyl groups on the luminescence performance of Ir(III) complexes: Preparation, structures, Electrochemistry, Photophysical properties and their applications in organic light emitting diodes (OLEDs) // Europ. Journ. of Inorg. Chem. 16 (2004), p. 3415-3423; Xu M.-L., Li T.-L., Li W.-L., Hong Z.-R., An Z.-W., Zhou Q. Optical and electroluminescent properties of a new Ir(III) complex- fac-tris[2,5-di(4-methoxyphenyl)pyridinato-C,N] iridium(III) // Thin Solid Films. 497 (2006), p. 239-242); Kwon S.-K., Kuppusamy Т., Kim S.-O., Youngjin K., Kim Y.-H. The Efficient Green Emitting Iridium(III) Complexes and Phosphorescent Organic Light Emitting Diode Characteristics, from “Organic Light Emitting Diode”, Marco Mazzeo (Ed.) (2010), ISBN: 978-953-307-140-4) и ацетилацетонаты замещенных бис(2-фенилпиридинато-N,C2′)иридия(III) (Liu Z.W., Bian Z.Q., Ming L., Ding F., Shen H.Y., Nie D.B., Huang C.H. Green and blue-green phosphorescent heteroleptic iridium complexes containing carbazole-functionalized β-diketonate for non-doped organic light-emitting diodes // Org. Electron. 9 (2008), p. 171-182), излучающие в синей и зеленой областях спектра.Known electroluminescent devices based on chelate complexes of iridium - substituted on the phenyl and pyridine rings of tris (2-phenylpyridinato-N, C 2 ′ ) iridium (III) (Jung S.-O., Kang Y., Kim H.-S., Kim Y.-H., Lee C.-L., Kim J.-J., Lee S.-K., Kwon S.-K. Effect of substitution of methyl groups on the luminescence performance of Ir (III) complexes : Preparation, structures, Electrochemistry, Photophysical properties and their applications in organic light emitting diodes (OLEDs) // Europ. Journ. Of Inorg. Chem. 16 (2004), p. 3415-3423; Xu M.-L., Li T.-L., Li W.-L., Hong Z.-R., An Z.-W., Zhou Q. Optical and electroluminescent properties of a new Ir (III) complex-fac-tris [2,5 -di (4-methoxyphenyl) pyridinato-C, N] iridium (III) // Thin Solid Films. 497 (2006), p. 239-242); Kwon S.-K., Kuppusamy T., Kim S.-O., Youngjin K., Kim Y.-H. The Efficient Green Emitting Iridium (III) Complexes and Phosphorescent Organic Light Emitting Diode Characteristics, from “Organic Light Emitting Diode”, Marco Mazzeo (Ed.) (2010), ISBN: 978-953-307-140-4) and substituted acetylacetonates bis (2-phenylpyridinato-N, C 2 ′ ) iridium (III) (Liu ZW, Bian ZQ, Ming L., Ding F., Shen HY, Nie DB, Huang CH Green and blue-green phosphorescent heteroleptic iridium complex containing carbazole -functionalized β-diketonate for non-doped organic light-emitting diodes // Org. Electron. 9 (2008), p. 171-182), emitting in the blue and green regions of the spectrum.
Наиболее близким по выполнению является электролюминесцентное устройство на основе хелатного комплекса иридия - бис(2-фенилпиридинато-N,C2′)[2-(2′-гидроксифенил)-5-метилбензоксазолато-N,O2′]иридия (A), являющееся наиболее близким по структуре к заявляемому соединению.The closest to implementation is an electroluminescent device based on a chelate complex of iridium - bis (2-phenylpyridinato-N, C 2 ′ ) [2- (2′-hydroxyphenyl) -5-methylbenzoxazolato-N, O 2 ′ ] iridium (A), which is the closest in structure to the claimed compound.
Комплекс проявляет высокоэффективную фотолюминесценцию в зеленой области (λФЛ=525 нм). OLED устройство с конфигурацией ITO/CuPc (10 нм)/NPD (40 нм)/комплекс A:CBP (30 нм)/BAlq (10 нм)/ 1 (Alq3) (30 нм) LiF:Al (150 нм) излучает в зеленой области (λЭЛ=515 нм), обладает яркостью 4753 кД/м2 при напряжении 9,5 В, координаты CIE (x=0.28, y=0.52). (You Y., Seo J., Kim S.H., Kim K.S., Ahn Т.К., Kim D., Park S.Y. Highly Phosphorescent Iridium Complexes with Chromophoric 2-(2-Hydroxyphenyl)oxazole- Based Ancillary Ligands: Interligand Energy-Harvesting Phosphorescence // Inorg. Chem. 47 (5) (2008) p. 1476-1487).The complex exhibits highly efficient photoluminescence in the green region (λ PL = 525 nm). An OLED device with the configuration ITO / CuPc (10 nm) / NPD (40 nm) / complex A: CBP (30 nm) / BAlq (10 nm) / 1 (Alq3) (30 nm) LiF: Al (150 nm) emits in the green region (λ EL = 515 nm), has a brightness of 4753 kD / m 2 at a voltage of 9.5 V, CIE coordinates (x = 0.28, y = 0.52). (You Y., Seo J., Kim SH, Kim KS, Ahn T.K., Kim D., Park SY Highly Phosphorescent Iridium Complexes with Chromophoric 2- (2-Hydroxyphenyl) oxazole-Based Ancillary Ligands: Interligand Energy-Harvesting Phosphorescence // Inorg. Chem. 47 (5) (2008) p. 1476-1487).
В ряду бис(2-фенилпиридинато-N,C2′) бензоксазолатов иридия, не известны соединения, излучающие в желтой области спектра.In the series of bis (2-phenylpyridinato-N, C 2 ′ ) iridium benzoxazolates, compounds emitting in the yellow spectral region are not known.
Техническим результатом изобретения являются новые соединения в ряду бис(2-фенилпиридинато-N,С2′) бензоксазолатов иридия, излучающие в желтой области спектра.The technical result of the invention is new compounds in the series of bis (2-phenylpyridinato-N, C 2 ′ ) iridium benzoxazolates emitting in the yellow region of the spectrum.
Технический результат достигается бис(2-фенилпиридинато-N,C2′){2-[2′-(4-алкилбензолсульфонамидо)фенил]бензоксазолато-N,N′}иридия(III) общей формулы I.The technical result is achieved bis (2-phenylpyridinato-N, C 2 ′ ) {2- [2 ′ - (4-alkylbenzenesulfonamido) phenyl] benzoxazolato-N, N ′} iridium (III) of the general formula I.
Способ их получения заключается во взаимодействии 2-[2′-(4-алкилбензолсульфонамидо)фенил]бензоксазолов (II) с тетракис(2-фенилпиридинато-N,C2′) (µ-дихлор) дииридием (III).The method for their preparation consists in the interaction of 2- [2 ′ - (4-alkylbenzenesulfonamido) phenyl] benzoxazoles (II) with tetrakis (2-phenylpyridinato-N, C 2 ′ ) (µ-dichloro) diiridium (III).
Техническим результатом изобретения является также электролюминесцентное устройство на основе хелатных комплексов - бис(2-фенилпиридинато-N,C2′) бензоксазолатов иридия в качестве активного люминесцентного слоя, излучающее в желтой области спектра.The technical result of the invention is also an electroluminescent device based on chelate complexes - bis (2-phenylpyridinato-N, C 2 ′ ) iridium benzoxazolates as an active luminescent layer, emitting in the yellow spectrum.
Технический результат достигается электролюминесцентным устройством, включающим дырочный инжектирующий, дырочный транспортный, дырочный блокирующий, электронный транспортный, электронный инжектирующий слои и активный люминесцирующий слой на основе люминесцентного вещества, в качестве которого он содержит бис(2-фенилпиридинато-N,C2′){2-[2′-(4-алкилбензолсульфонамидо)фенил] бензоксазолато-N,N′}иридия(III) I.The technical result is achieved by an electroluminescent device, including a hole injection, hole transport, hole blocking, electronic transport, electronic injection layers and an active luminescent layer based on a luminescent substance, in which it contains bis (2-phenylpyridinato-N, C 2 ′ ) {2 - [2 ′ - (4-alkylbenzenesulfonamido) phenyl] benzoxazolato-N, N ′} iridium (III) I.
Изобретение удовлетворяет критерию изобретательского уровня, так как используемый комплекс иридия формулы I не известен как электролюминесцентное вещество.The invention meets the criteria of an inventive step, since the iridium complex of formula I used is not known as an electroluminescent substance.
Ниже приведены примеры получения соединения и его применения.The following are examples of the preparation of the compound and its use.
Пример 1. Получение 2-(2′-тозиламинофенил)бензоксазола (II, R=CH3).Example 1. Obtaining 2- (2′-tosylaminophenyl) benzoxazole (II, R = CH 3 ).
Синтез 2-(2′-тозиламинофенил)бензоксазола II осуществляют по методике [Чернова Н.И., Лосева М.В., Болотин Б.М., Нурмухаметов Р.Н., Рябокобылко Ю.С. Синтез и оптические свойства 5-замещенных 2-(2-тозиламинофенил)бензоксазолов. Химия гетероцикл. соедин. 1973. №4. С. 492-498].The synthesis of 2- (2′-tosylaminophenyl) benzoxazole II is carried out according to the method [Chernova N.I., Loseva M.V., Bolotin B.M., Nurmukhametov R.N., Ryabokobylko Yu.S. Synthesis and optical properties of 5-substituted 2- (2-tosylaminophenyl) benzoxazoles. Chemistry heterocycle. connection 1973. No. 4. S. 492-498].
К раствору 10.91 г (0.1 моль) о-аминофенола в 250 мл диоксана при перемешивании прибавляют 30.97 г (0.1 моль) хлорангидрида тозилантраниловой кислоты. Реакционную смесь охлаждают до комнатной температуры. Выделившееся масло через 30 мин превращается в кристаллический осадок, который отфильтровывают, промывают и кристаллизуют из метанола. Ацилированный о-аминофенол нагревают при 180-200°C. Образовавшуюся твердую массу охлаждают и очищают хроматографированием на окиси алюминия (элюент - хлороформ) и последующей перекристаллизацией из метанола. Получают 22.5 г чистого вещества. Т. пл. 165-166°C. Выход 64%.To a solution of 10.91 g (0.1 mol) of o-aminophenol in 250 ml of dioxane, 30.97 g (0.1 mol) of tosylanthranilic acid chloride are added with stirring. The reaction mixture was cooled to room temperature. After 30 minutes, the oil that separated out turns into a crystalline precipitate, which is filtered off, washed and crystallized from methanol. The acylated o-aminophenol is heated at 180-200 ° C. The resulting solid mass is cooled and purified by chromatography on alumina (eluent is chloroform) and subsequent recrystallization from methanol. 22.5 g of pure substance are obtained. T. pl. 165-166 ° C. Yield 64%.
Найдено, %: C 66.10; H 4.51; N 7.59; S 8.75. Для C20H16N2O3S вычислено, %: C 65.91; H 4.43; N 7.69; S 8.80.Found,%: C 66.10; H 4.51; N, 7.59; S 8.75. For C 20 H 16 N 2 O 3 S calculated,%: C 65.91; H 4.43; N, 7.69; S 8.80.
1H ЯМР спектр, ДМСО-d6, δ, м.д.: 2.25 (с, 3H, CH3), 7.24-8.12 (м, 12H, CAr-H), 11.44 (уш. с, 1H, NH). 1 H NMR spectrum, DMSO-d 6 , δ, ppm: 2.25 (s, 3H, CH 3 ), 7.24-8.12 (m, 12H, C Ar -H), 11.44 (br s, 1H, NH )
ИК спектр, (порошок), ν (см-1): 1615 ср., 1588 с., 1538 ср. (бензоксазольная система), 1340 с. (νas SO2), 1160 о.с. (νs SO2), 3433 (NH).IR spectrum, (powder), ν (cm -1 ): 1615 sr., 1588 s., 1538 sr. (benzoxazole system), 1340 s. (ν as SO 2 ), 1160 o.s. (ν s SO 2 ), 3433 (NH).
Пример 2. Получение тетракис(2-фенилпиридинато-N,C2′) (µ-дихлор) дииридия (III) (II).Example 2. Obtaining tetrakis (2-phenylpyridinato-N, C 2 ′ ) (µ-dichloro) diiridium (III) (II).
Синтез осуществляют по методике [Tamayo А.В., Alleyne B.D., Djurovich P.I., Lamansky S., Tsyba I., Ho N.N., Bau R., Thompson M.E. Synthesis and Characterization of Facial and Meridional Tris-cyclometalated Iridium (III) Complexes // J. Am. Chem. Soc. 125 (2003) pp. 7377-7387).The synthesis is carried out according to the method [Tamayo A.V., Alleyne B.D., Djurovich P.I., Lamansky S., Tsyba I., Ho N.N., Bau R., Thompson M.E. Synthesis and Characterization of Facial and Meridional Tris-cyclometalated Iridium (III) Complexes // J. Am. Chem. Soc. 125 (2003) pp. 7377-7387).
К 27 мл смеси этилцеллозольва и воды (в объемном отношении 3:1) добавляют 352 мг (1.0 ммоль) тригидрата хлорида иридия и 372 мг (2.4 ммоль) 2-фенилпиридина. Смесь нагревают при перемешивании в атмосфере аргона при 110°C в течение 12 часов. Охлаждают, осадок ярко-желтого цвета отфильтровывают, промывают этанолом и гексаном, высушивают на воздухе. Выход 346 мг (63%). Соединение III без очистки используют для получения комплекса I.To 27 ml of a mixture of ethyl cellosolve and water (in a volume ratio of 3: 1) add 352 mg (1.0 mmol) of iridium chloride trihydrate and 372 mg (2.4 mmol) of 2-phenylpyridine. The mixture is heated with stirring in an argon atmosphere at 110 ° C for 12 hours. It is cooled, the bright yellow precipitate is filtered off, washed with ethanol and hexane, and dried in air. Yield 346 mg (63%). Compound III without purification is used to obtain complex I.
Пример 3. Получение бис(2-фенилпиридинато-N,C2′)[2-(2′-тозиламинофенил)бензоксазолато-N,N′]иридия(III) (I, R=CH3).Example 3. Obtaining bis (2-phenylpyridinato-N, C 2 ′ ) [2- (2′-tosylaminophenyl) benzoxazolato-N, N ′] iridium (III) (I, R = CH 3 ).
Смесь 172 мг (0.16 ммоль) тетракис(2-фенилпиридинато-N,C2′) (µ-дихлор) дииридия (III) (III), 128 мг (0.35 ммоль) 2-(2′-тозиламинофенил)бензоксазола (II, R=CH3) и 170 мг (1.6 ммоль) карбоната натрия в 14 мл этилцеллозольва нагревают при перемешивании в атмосфере аргона при 140°C в течение 5 часов. Охлаждают, добавляют 70 мл этилацетата. Затем для извлечения этилцеллозольва обрабатывают 120 мл воды (3×40 мл). Этилацетат отгоняют, остаток обрабатывают 10 мл смеси этилацетат:гексан (2:3), нерастворившуюся часть отфильтровывают, промывают этой же смесью, высушивают. Очищают на хроматографической колонке (силикагель, элюент - хлористый метилен), собирая фракцию с Rf 0.1. Выход 182 мг (66%). После перекристаллизации из ацетонитрила оранжевые кристаллы с т.пл. >250°C.A mixture of 172 mg (0.16 mmol) of tetrakis (2-phenylpyridinato-N, C 2 ′ ) (µ-dichloro) diiridium (III) (III), 128 mg (0.35 mmol) of 2- (2′-tosylaminophenyl) benzoxazole (II, R = CH 3 ) and 170 mg (1.6 mmol) of sodium carbonate in 14 ml of ethyl cellosolve are heated with stirring in an argon atmosphere at 140 ° C for 5 hours. Cool, add 70 ml of ethyl acetate. Then, 120 ml of water (3 × 40 ml) are treated to extract ethyl cellosolve. Ethyl acetate was distilled off, the residue was treated with 10 ml of a mixture of ethyl acetate: hexane (2: 3), the insoluble part was filtered off, washed with the same mixture, and dried. Purify on a chromatographic column (silica gel, eluent - methylene chloride), collecting a fraction with R f 0.1. Yield 182 mg (66%). After recrystallization from acetonitrile, orange crystals with mp. > 250 ° C.
Найдено, %: C 58.30; H 3.71; N 6.57. Для C42H31IrN4O3S вычислено, %: C 58.39; H 3.62; N 6.48.Found,%: C 58.30; H 3.71; N, 6.57. For C 42 H 31 IrN 4 O 3 S calculated,%: C 58.39; H 3.62; N, 6.48.
ИК-спектр (в твердой фазе): 1608 ср, 1602 ср, 1583 ср, 1563 ср, 1476 с, 1454 ср, 1439 ср, 1426 ср, 1418 ср, 1351 сл, 1324 сл, 1298 с (νas SO2), 1285 ср, 1264 ср, 1231 с, 1187 ср, 1165 сл, 1134 с (νs SO2), 1085 с, 1063 ср, 1048 ср, 1030 ср, 1008 сл, 983 сл, 959 ср, 921 с, 895 сл, 864 сл, 824 ср, 807 ср, 791 ср, 753 с, 731 с, 712 ср, 689 ср, 669 сл, 649 с, 630 с, 585 ср, 558 с см-1.IR spectrum (in solid phase): 1608 sr, 1602 sr, 1583 sr, 1563 sr, 1476 s, 1454 sr, 1439 sr, 1426 sr, 1418 sr, 1351 sl, 1324 sl, 1298 s (ν as SO 2 ) , 1285 sr, 1264 sr, 1231 s, 1187 sr, 1165 s, 1134 s (ν s SO 2 ), 1085 s, 1063 sr, 1048 sr, 1030 sr, 1008 s, 983 s, 959 sr, 921 s, 895 sl, 864 sl, 824 sr, 807 sr, 791 sr, 753 s, 731 s, 712 sr, 689 sr, 669 sl, 649 s, 630 s, 585 sr, 558 s cm -1 .
1H ЯМР спектр, CDCl3, δ, м.д.: 2.21 (3H, с, CH3), 6.31 (1Н, д, J=7.8 Гц, CAr-H), 6.50 (1Н, д, J=7.5 Гц, CAr-H), 6.66 (2Н, т, J=7.0 Гц, CAr-H), 6.73-6.85 (8Н, м, CAr-H), 6.88 (2Н, д, J=8.1 Гц, CAr-H), 6.96-7.01 (1H, м, CAr-H), 7.18 (2H, т, J=7.8 Гц, CAr-H), 7.28 (2H, д, J=8.1 Гц, CAr-H), 7.50 (2H, д, J=8.1 Гц, CAr-H), 7.53-7.60 (3H, м, CAr-H), 7.66-7.73 (2H, м, CAr-Н), 7.84 (1H, д, J=8.1 Гц, CAr-H), 8.19 (1H, уш. с, CAr-H). 1 H NMR spectrum, CDCl 3 , δ, ppm: 2.21 (3H, s, CH 3 ), 6.31 (1H, d, J = 7.8 Hz, CAr-H), 6.50 (1H, d, J = 7.5 Hz, C Ar -H), 6.66 (2H, t, J = 7.0 Hz, CAr-H), 6.73-6.85 (8H, m, C Ar -H), 6.88 (2H, d, J = 8.1 Hz, C Ar -H), 6.96-7.01 (1H, m, C Ar -H), 7.18 (2H, t, J = 7.8 Hz, C Ar -H), 7.28 (2H, d, J = 8.1 Hz, C Ar - H), 7.50 (2H, d, J = 8.1 Hz, C Ar -H), 7.53-7.60 (3H, m, C Ar -H), 7.66-7.73 (2H, m, C Ar -H), 7.84 ( 1H, d, J = 8.1 Hz, C Ar -H), 8.19 (1H, br.s, C Ar -H).
УФ-спектр: 405, 440, 475 нм (поглощение, ДМСО). Люминесценция 591 нм (ДМСО, λвозб=590 нм).UV spectrum: 405, 440, 475 nm (absorption, DMSO). Luminescence 591 nm (DMSO, λ exc = 590 nm).
Пример 4. Электролюминесцентные свойства.Example 4. Electroluminescent properties.
Использованные в работе вещества и ссылки на каталоги:Substances used in the work and links to catalogs:
1. Phthalocyanine Copper complex (CuPc), ALDRICH, CAS 147-148.1. Phthalocyanine Copper complex (CuPc), ALDRICH, CAS 147-148.
2. 4,4′,4″-Tris(N-(2-naphthyl)-N-phenyl-amino)triphenylamine (2-TNATA) KINTEC, lot: KZ88BuOMEEO, sales@kintec.hk2.4,4 ′, 4 ″ -Tris (N- (2-naphthyl) -N-phenyl-amino) triphenylamine (2-TNATA) KINTEC, lot: KZ88BuOMEEO, sales@kintec.hk
3. Di-[4-(N,N-di-p-tolyl-amino)-phenyl]cyclohexane (TAPC), Luminescence Technology Corp, CAS: 58473-78-2.3. Di- [4- (N, N-di-p-tolyl-amino) -phenyl] cyclohexane (TAPC), Luminescence Technology Corp, CAS: 58473-78-2.
4. 4,4′-Bis(carbazol-9-yl)biphenyl(СВР)), Luminescence Technology Corp, CAS: 58328-31-74.4,4′-Bis (carbazol-9-yl) biphenyl (CBP)), Luminescence Technology Corp, CAS: 58328-31-7
5. 2,9-Dimethyl-4,7-diphenyl-1,10-phenanhroline (BCP) KINTEC, lot: KZ86BUOHRYO, sales@kintec.hk5.2.9-Dimethyl-4,7-diphenyl-1,10-phenanhroline (BCP) KINTEC, lot: KZ86BUOHRYO, sales@kintec.hk
6. 4,7-Diphenyl-1,10-phenanthroline (Bphen) KINTEC, lot: KZ88BuOMEEO, sales@kintec.hk6,4,7-Diphenyl-1,10-phenanthroline (Bphen) KINTEC, lot: KZ88BuOMEEO, sales@kintec.hk
7. LiF ALDRICH, CAS: 7789-24-4.7. LiF ALDRICH, CAS: 7789-24-4.
Для изготовления электролюминесцентного устройства /ЭЛУ/ со структурой ITO/CuPc/2-TNATA/ТАРС/комплекс I (R=СН3) : CBP/BCP/Bphen/LiF/Al используют стеклянную подложку с полупрозрачным слоем смешанного оксида индия и олова с сопротивлением 30-70 Ом/квадрат (дырочно-инжектирующий слой). На подложку методом испарения в вакууме последовательно наносят следующие слои: слой CuPc (дырочно-инжектирующий слой) толщиной 0.004 мкм, слой 2-TNATA (дырочно-транспортный слой) толщиной 0.020 мкм, слой ТАРС (дырочно-транспортный слой) толщиной 0.015 мкм, слой комплекса иридия I (R=CH3) в СВР толщиной 0.016 мкм, слой ВСР (дырочно-блокирующий слой) толщиной 0.006 мкм, слой Bphen (электронно-транспортный слой) толщиной 0.020 мкм и слой LiF (электронно-инжектирующий слой) толщиной 0.001 мкм. Затем также методом испарения в вакууме напыляют алюминиевый электрод (электронно-инжектирующий слой). Толщина металлического электрода порядка 0,1 мкм. Площадь светящейся поверхности 8.0 мм2. Полученное ЭЛУ обладает следующими параметрами: яркость 7500 кд/м2 достигается при напряжении 15 В и токе 120 мА (рис. 1. Вольт-амперные и Вольт-яркостные характеристики ЭЛУ с соединением I (R=CH3). ЭЛУ является источником, излучающим в желтой области спектра с максимумом электролюминесценции около 630 нм (рис. 2. Электролюминесценция ЭЛУ). Координаты цветности CIE (Commission internationale de l′eclairage) для ЭЛУ x=0.513, y=0.465 (рис. 3. Координаты цветности CIE для ЭЛУ).For the manufacture of an electroluminescent device / ELU / with the structure ITO / CuPc / 2-TNATA / TARS / complex I (R = CH 3 ): CBP / BCP / Bphen / LiF / Al, a glass substrate with a translucent layer of mixed indium tin oxide with resistance is used 30-70 Ohm / square (hole-injecting layer). The following layers are successively applied to the substrate by vacuum evaporation: a CuPc layer (hole-injection layer) 0.004 μm thick, a 2-TNATA layer (hole-transport layer) 0.020 μm thick, a TARS layer (hole-transport layer) 0.015 μm thick, a layer a complex of iridium I (R = CH 3 ) in an SVR with a thickness of 0.016 μm, a HRV layer (hole-blocking layer) with a thickness of 0.006 μm, a Bphen layer (electron transport layer) with a thickness of 0.020 μm, and a LiF layer (electron-injection layer) with a thickness of 0.001 μm . Then, an aluminum electrode (electron-injection layer) is also sprayed by vacuum evaporation. The thickness of the metal electrode is about 0.1 μm. The area of the luminous surface is 8.0 mm 2 . ELU obtained has the following parameters: brightness 7,500 cd / m 2 is achieved at a voltage of 15 V and a current of 120 mA (Fig 1. The current-voltage and voltage-luminance characteristics ELU with compound I (R = CH 3) ELU source is emitting.. in the yellow region of the spectrum with an electroluminescence maximum of about 630 nm (Fig. 2. Electroluminescence of ELU). CIE chromaticity coordinates (Commission internationale de l′eclairage) for ELU x = 0.513, y = 0.465 (Fig. 3. CIE chromaticity coordinates for ELU) .
Claims (2)
где R = алкил (С1-С6).1. Bis (2-phenylpyridinato-N, C 2 ′ ) {2- [2 ′ - (4-alkylbenzenesulfonamido) phenyl] benzoxazolato-N, N ′} iridium (III) of formula I
where R = alkyl (C 1 -C 6 ).
где R = алкил (С1-С6). 2. An electroluminescent device, including a hole injection, hole transport, hole blocking, electronic transport, electronic injection layers and an active luminescent layer based on a luminescent substance, which contains bis (2-phenylpyridinato-N, C 2 ′ ) {2- [2 ′ - (4-alkylbenzenesulfonamido) phenyl] benzoxazolato-N, N ′} iridium (III) of formula I
where R = alkyl (C 1 -C 6 ).
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