CN104447879A - Iridium complex-containing compounds of quinoline derivative structural units as well as preparation method and application thereof - Google Patents
Iridium complex-containing compounds of quinoline derivative structural units as well as preparation method and application thereof Download PDFInfo
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 61
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 229910052741 iridium Inorganic materials 0.000 title claims abstract description 11
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title abstract 2
- 239000000463 material Substances 0.000 claims abstract description 39
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical class [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052697 platinum Chemical class 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 27
- 238000006467 substitution reaction Methods 0.000 claims description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 9
- 230000005525 hole transport Effects 0.000 claims description 8
- 238000002347 injection Methods 0.000 claims description 8
- 239000007924 injection Substances 0.000 claims description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
- 238000010992 reflux Methods 0.000 claims description 8
- 239000000758 substrate Substances 0.000 claims description 8
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 7
- 239000003513 alkali Substances 0.000 claims description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 7
- 229910052709 silver Inorganic materials 0.000 claims description 7
- 239000004332 silver Substances 0.000 claims description 7
- 239000012298 atmosphere Substances 0.000 claims description 6
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical group [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 claims description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 5
- 239000011777 magnesium Substances 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 4
- 239000002322 conducting polymer Substances 0.000 claims description 4
- 229920001940 conductive polymer Polymers 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 239000010949 copper Substances 0.000 claims description 4
- 239000011521 glass Substances 0.000 claims description 4
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052737 gold Inorganic materials 0.000 claims description 4
- 239000010931 gold Substances 0.000 claims description 4
- 229910010272 inorganic material Inorganic materials 0.000 claims description 4
- 239000011147 inorganic material Substances 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- 125000005595 acetylacetonate group Chemical group 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims description 2
- 229940077388 benzenesulfonate Drugs 0.000 claims description 2
- 230000005540 biological transmission Effects 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 229910052738 indium Inorganic materials 0.000 claims description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 2
- 229920000767 polyaniline Polymers 0.000 claims description 2
- 229920000123 polythiophene Polymers 0.000 claims description 2
- 229920001447 polyvinyl benzene Polymers 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229910052712 strontium Inorganic materials 0.000 claims description 2
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 239000011787 zinc oxide Substances 0.000 claims description 2
- BNEMLSQAJOPTGK-UHFFFAOYSA-N zinc;dioxido(oxo)tin Chemical compound [Zn+2].[O-][Sn]([O-])=O BNEMLSQAJOPTGK-UHFFFAOYSA-N 0.000 claims description 2
- 150000002503 iridium Chemical class 0.000 abstract description 6
- 239000002994 raw material Substances 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 23
- 238000001704 evaporation Methods 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 230000008020 evaporation Effects 0.000 description 11
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 150000003057 platinum Chemical class 0.000 description 4
- 150000003248 quinolines Chemical class 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 0 *c1cc(-c2nc3ccccc3cc2)c(*)c(*)c1* Chemical compound *c1cc(-c2nc3ccccc3cc2)c(*)c(*)c1* 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 238000011056 performance test Methods 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 3
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Substances C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 3
- 229910001316 Ag alloy Inorganic materials 0.000 description 2
- 229910021638 Iridium(III) chloride Inorganic materials 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- 229910000861 Mg alloy Inorganic materials 0.000 description 2
- 125000001931 aliphatic group Chemical class 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 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 2
- 238000011160 research Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000009210 therapy by ultrasound Methods 0.000 description 2
- FYWDEEUCCVRSPL-UHFFFAOYSA-N 1-chloro-2h-quinoline Chemical compound C1=CC=C2N(Cl)CC=CC2=C1 FYWDEEUCCVRSPL-UHFFFAOYSA-N 0.000 description 1
- JRFVWNRVFJRGKW-UHFFFAOYSA-N 1-iodo-4-[4-(4-propylcyclohexyl)cyclohexyl]benzene Chemical compound C1CC(CCC)CCC1C1CCC(C=2C=CC(I)=CC=2)CC1 JRFVWNRVFJRGKW-UHFFFAOYSA-N 0.000 description 1
- GDOPTJXRTPNYNR-UHFFFAOYSA-N CC1CCCC1 Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910021639 Iridium tetrachloride Inorganic materials 0.000 description 1
- 229910020427 K2PtCl4 Inorganic materials 0.000 description 1
- 229910019032 PtCl2 Inorganic materials 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000006161 Suzuki-Miyaura coupling reaction Methods 0.000 description 1
- 229940008309 acetone / ethanol Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical group Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 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
-
- 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
- C07F15/0086—Platinum compounds
-
- 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
- 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
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention discloses iridium complex-containing compounds of quinoline derivative structural units as well as a preparation method and application thereof. A structural general formula of the compounds is shown in a formula I in the specification. The invention provides a series of iridium or platinum complex electrophosphorescent materials with chiral groups because efficient electrophosphorescent materials with good film-forming properties and shorter phosphorescence lifetime are needed and in order that the luminescent efficiency and the properties of luminescent devices are improved at the same time. The compounds have the characteristics of excellent film-forming properties, high luminescent efficiency, and the like, are accessible in raw materials, are simple and convenient to prepare, have high total yields, have the effect of greatly reducing the costs of phosphorescent materials and have important application values.
Description
Technical Field
The invention belongs to the field of OLED materials, and relates to a compound containing an iridium complex quinoline derivative structural unit, and a preparation method and application thereof.
Background
For organic electroluminescent diodes (abbreviated as OLEDs) and related research, the electroluminescence of organic compound single-crystal anthracene was first discovered by pope et al as early as 1963. Kodak company of the United states of 1987 made an amorphous film device by evaporating small organic molecules, and reduced the driving voltage to within 20V. The device has the advantages of ultra-light weight, full curing, self luminescence, high brightness, wide viewing angle, high response speed, low driving voltage, low power consumption, bright color, high contrast, simple process, good temperature characteristic, soft display and the like, and can be widely applied to flat panel displays and surface light sources, so the device is widely researched, developed and used.
Through the development of twenty years, the organic EL material has comprehensively realized red, blue and green luminescence, and the application field has also been expanded from small molecules to the fields of high molecules, metal complexes and the like. In recent years, organic electroluminescent display technology has been greatly developed, and light emission of three primary colors of red, blue, and green has been realized. However, currently known materials with practical value and potential are very limited, especially organic materials with excellent comprehensive indexes need to be researched and developed urgently, green materials develop fastest and can basically meet the requirements of commercialization and practicability, and red and blue materials have more problems and are far away from practical application. Therefore, the molecular design and synthesis of stable and efficient red light materials become important research contents.
Disclosure of Invention
The invention aims to provide a compound containing an iridium complex quinoline derivative structural unit, and a preparation method and application thereof.
The structural general formula of the compound containing the structural unit of the quinoline derivative of the iridium complex is shown as formula I,
R1and R2Any one selected from H, F, -CN, methoxyl and trifluoromethoxy;
R3and R4Selected from H and trans-cyclohexyl substituted C1-C50, and R3And R4Not H at the same time;
m is iridium or platinum;
x is 1, 2 or 3;
y is 0, 1, 2 or 3; and when x is 3, y is 0;
l is an acetylacetonate group.
In the trans-cyclohexyl-substituted aliphatic hydrocarbon group of C1-C50, the number of trans-cyclohexyl as a substituent can be specifically 1-5, more specifically 2; the connection mode between trans-cyclohexyl used as substituent groups is a connection mode of a para-single bond; for example, 2 trans-cyclohexyl groups as substituents have the formulaThe structural formula of the 3 trans-cyclohexyl as the substituent isThe structural formula of 4 trans-cyclohexyl as substituent isThe structural formula of the 5 trans-cyclohexyl as the substituent isThe aliphatic hydrocarbon group of C1-C50 can be alkyl of C1-C20, more specifically can be alkyl of C1-C10; still more specifically, it may be a C-C alkyl group, a C-C alkyl group or a C-C alkyl group;
the R is4In particular hydrogen;
specifically, the compound shown in the formula I is any one of the following compounds:
the method for preparing the compound shown in the formula I is the following one or two;
the first method comprises the following steps:
will be provided withMixing with acetylacetone and alkali in solvent, reflux for substitution
Will be provided withAnduniformly mixing the mixture in a solvent for substitution reaction, and obtaining a compound shown as a formula I when x is 3 after the reaction is finished;
the R is1-R4And M is as defined above.
The reaction schemes of the above two methods are as follows:
in the first method, the first step is that,the feeding molar ratio of the acetylacetone to the alkali is 1: 2-4: 2-10, specifically 1: 2: 10-1: 3.2: 6.8; in the step of substitution reaction, the temperature is 170-190 ℃, in particular 180 ℃; the time is 10-24 hours, specifically 20-24 hours;
in the second method, the first step is that,andthe mass ratio of (1): 3-4, specifically 1: 3.7;
in the step of substitution reaction, the temperature is 170-190 ℃, in particular 180 ℃; the time is 7-9 hours, specifically 8 hours.
In the first and second methods, the base is at least one selected from anhydrous sodium carbonate and anhydrous potassium carbonate;
the substitution reaction is carried out in an inert atmosphere; the inert atmosphere is specifically nitrogen atmosphere;
the solvent is at least one selected from ethylene glycol ethyl ether, tetrahydrofuran, n-hexane, toluene, ethanol, water, glycerol, 1, 4-dioxane, acetonitrile and chloroform.
In the above process, as starting reactantAndthe preparation method can be as follows:
1) 1-R1-2-R2-3-R3-4-R4Benzene and n-butyl lithium are subjected to negative ionization reaction for 1 hour at the temperature of between 110 ℃ below zero and 60 ℃ below zero in a solvent, trimethyl borate is added into the solvent to perform substitution reaction for 1 hour at the temperature of between 110 ℃ below zero and 60 ℃ below zero, and then the mixture is acidified in hydrochloric acid for 30 minutes to obtain the compound
2) Subjecting the product obtained in step 1)Base and catalyst Pd (PPh)3)4Mixing uniformly in a solvent, refluxing for Suzuki-Miyaura coupling reaction for 8-12 hours to obtain the product
3) Subjecting the product obtained in step 2)Refluxing with iridium salt or platinum salt in solvent for substitution reaction for 10-24 hr to obtain
In the general structural formula of each reactant in the method, R1-R4M and x are each as defined above for R in formula I1-R4M and x are as defined.
In step 1) of the above process, 1-R1-2-R2-3-R3-4-R4The feeding molar ratio of benzene to n-butyllithium is 1:1 to 3, specifically 1:1, 1:1.2, 1:1.5, 1:2, 1:2.5, 1:3, preferably 1:1.2 to 1.5; the 1-R1-2-R2-3-R3-4-R4The feeding molar ratio of benzene to trimethyl borate is 1:1 to 3, specifically 1:1, 1:1.2, 1:1.5, 1:2, 1:2.5, 1:3, preferably 1:1.2 to 1.5;
in the step 2), the alkali is at least one of anhydrous sodium carbonate and anhydrous potassium carbonate;
the feeding molar ratio of the alkali to the catalyst is 1: 1-2: 2-4: 0.005-0.01, specifically 1: 1.5: 4: 0.01;
in step 3), the iridium salt is IrCl3、IrCl33H2O or IrCl4；
The platinum salt is K2PtCl4、PtCl2Or KPtCl4；
The above-mentionedThe feeding molar ratio of iridium salt or platinum salt to iridium salt or platinum salt is 1: 0.3-0.6, specifically 1: 0.5;
the reactions in the steps 1) to 3) are carried out in an inert atmosphere; the inert atmosphere is specifically nitrogen atmosphere;
in the steps 1) to 3), the solvent is at least one selected from ethylene glycol ethyl ether, tetrahydrofuran, methyl tert-butyl ether, n-hexane, toluene, ethanol, water, glycerol, 1, 4-dioxane, acetonitrile and chloroform.
In addition, the light-emitting material containing the compound shown in the formula I, the application of the compound shown in the formula I in preparing the light-emitting material, the application of the compound shown in the formula I as a light-emitting layer in preparing an organic electroluminescent device and the organic electroluminescent device containing the compound shown in the formula I as the light-emitting layer also belong to the protection scope of the invention. The luminescent material is specifically an organic electrophosphorescent luminescent material, and more specifically an organic electrophosphorescent luminescent material with the luminescent wavelength of 460nm-680 nm; the organic electroluminescent device is specifically an organic electrophosphorescent luminescent device. The emission wavelength may be 590, 604, 620 or 680 nm.
The application of the compound shown in the formula I in preparing an organic electroluminescent device or an organic light-emitting diode and the organic electroluminescent device or the organic light-emitting diode containing the compound shown in the formula I also belong to the scope of the invention.
Specifically, the organic electroluminescent device consists of a transparent substrate, an anode, a hole injection layer, a hole transport layer, an organic light emitting layer, an electron transport layer and a cathode layer from bottom to top in sequence;
wherein, the material for forming the transparent substrate is glass or a flexible substrate;
the anode layer is made of inorganic materials or organic conducting polymers; wherein the inorganic material is indium tin oxide, zinc oxide, tin zinc oxide, gold, silver or copper; the organic conducting polymer is selected from at least one of polythiophene, sodium polyvinyl benzene sulfonate and polyaniline;
the material for forming the hole injection layer is 2T-NATA; the structural formula of the 2T-NATA is as follows:
the material constituting the hole transport layer is NPB; the structural formula of the NPB is as follows:
the material for forming the organic light-emitting layer is the compound shown in the formula I provided by the invention;
the material for forming the electron transport layer is Alq3, Gaq3 or BPhen;
wherein the structural formulas of Alq3, BPhen and Gaq3 are as follows in sequence:
the cathode layer is made of a material selected from any one or two of the following elements: lithium, magnesium, silver, calcium, strontium, aluminum, indium, copper, gold, and silver.
The thickness of the hole injection layer is 30-50nm, specifically 40 nm;
the thickness of the hole transport layer is 5-15nm, specifically 10 nm;
the thickness of the organic light-emitting layer is 10-100nm, specifically 50 nm;
the thickness of the electron transmission layer is 10-30nm, specifically 20 nm;
the thickness of the cathode layer is 90-110nm, specifically 100 nm.
The invention provides a series of iridium or platinum complex electrophosphorescent luminescent materials with chiral groups based on the fact that electrophosphorescent materials need high film-forming properties and high-efficiency phosphorescent materials with short phosphorescence life, and meanwhile, the invention improves the luminous efficiency and the performance of luminescent devices. The compound has the advantages of easily obtained synthetic raw materials, simple and convenient preparation and high overall yield, greatly reduces the cost of the phosphorescent material, and has important application value.
Detailed Description
The present invention will be further illustrated with reference to the following specific examples, but the present invention is not limited to the following examples. The method is a conventional method unless otherwise specified. The starting materials are commercially available from the open literature unless otherwise specified. In the examples below, THF represents tetrahydrofuran, DCM represents dichloromethane, Et3N represents triethylamine, Pd (PPh)3)4Represents tetrakis (triphenylphosphine) palladium, PPh3Represents triphenylphosphine.
The following examples are provided for testing the performance of OLED materials and devices using the following test apparatus and method:
emission wavelength and chromaticity coordinates: testing with a photosresearch PR-655 spectrum scanner;
current density and lighting voltage: testing using a digital source table Keithley 2420;
power efficiency: tested using NEWPORT 1931-C.
In the following examples, the starting reactant G-2' was prepared as follows:
the first step is as follows: preparation of Compound G-0
4.1G of 4- (4-iodophenyl) -4 '-propylbicyclohexane was dissolved in 50ml of anhydrous THF, the temperature was reduced to-80 ℃ with liquid nitrogen, 6.0ml of a 2.5M n-butyllithium-hexane solution was slowly added dropwise under nitrogen protection, after stirring and reacting for 30 minutes, a solution of 1.25G of trimethyl borate in THF was slowly added dropwise, after stirring and reacting for 30 minutes, the temperature was raised to room temperature and the reaction was stirred for 1 hour, 150ml of a 6M dilute aqueous hydrochloric acid solution was added dropwise, extraction was performed with ethyl acetate, the organic phase was dried over anhydrous sodium sulfate, filtration was performed, concentration under reduced pressure was performed, 50ml of petroleum ether was added to the residue and dispersion was performed with stirring, and suction filtration was performed to obtain 2.9G of Compound G-0', a white solid.
The second step is that: preparation of Compound G-1
3.2G of the compound G-0 obtained in the above step, 1.6G of 1-chloroquinoline, 2.0G of anhydrous potassium carbonate, 50ml of toluene, 20ml of ethanol and 20ml of water were mixed, and 115mg of Pd as a catalyst (PPh) was added3)4Heating and refluxing for coupling reaction for 12 hours under the protection of nitrogen, cooling to room temperature, separating an organic phase, extracting an aqueous phase by using ethyl acetate, drying the organic phase, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying the residue by using a silica gel column to obtain 2.8G of G-1, namely a white solid.
The third step: preparation of Compound G-2
1.06G of Compound G-1' and 0.46G of MCl3·3H2O (M is Ir or Pt) is dispersed in 15ml of ethylene glycol ethyl ether and 5ml of water, the substitution reaction is carried out for 24 hours under the protection of nitrogen by heating and refluxing, the mixture is cooled to the room temperature, filtered, the filter cake is washed by water and dried in vacuum, and 1.1G of compound G-2' (x is 1 or 2) is obtained as a reddish brown solid.
The structure confirmation data for this product are as follows:
1HNMR(、CDCl3)：0.80～0.99(3H,m)；1.28～1.35(2H,m)；1.53～1.58(2H,m)；1.73～1.90(3H,m)；1.96～2.22(16H,m)；2.64～2.78(1H,m)；6.58～6.65(2H,q)；6.96～7.01(2H,t)；7.75～7.79(2H,t)；8.21～8.33(4H,m)
EXAMPLE 1 preparation of the Compound JIR-LC-I-011 (method one)
1000mg (0.5mmol) of the compound G-2' (x is 2) and 98mg (1mmol) of acetylacetone and 519mg (5mmol) of anhydrous sodium carbonate are dispersed in 40ml of acetonitrile and 40ml of chloroform, the temperature is raised under reflux to 180 ℃ under nitrogen protection to carry out substitution reaction for 24 hours, the reaction solution is cooled to room temperature, poured into water, extracted with DCM, the organic phase is dried, filtered, the filtrate is concentrated under reduced pressure to dryness, and the residue is separated and purified by a silica gel column to obtain 650mg of the compound JIR-LC-I-001 as a red solid.
Experimental data:
(1)1HNMR(、CDCl3): 0.08 to 0.10(1H, m); 0.12 to 0.18(3H, m); 0.53 to 0.58(1H, d); 0.73 to 0.90(10H, m); 0.96-1.42 (15H, m); 1.64 to 1.78(5H, m); 6.58 to 6.65(1H, q); 6.96-7.01 (1H, t); 7.75 to 7.79(1H, t); 8.21 to 8.33(2H, m). It was confirmed that the substance obtained by the reaction was indeed the compound JIR-LC-I-011;
(2) glass transition temperature (DSC): 248.78 deg.C;
(3) UV maximum absorption wavelength (DCM): 226nm,280nm,346 nm;
(4) phosphorescent emission wavelength (DCM): 620 nm.
EXAMPLE 2 preparation of the Compound JIR-LC-II-001 (method two)
1080mg of compound G-1 'and 3970mg of compound G-2' (x is 2) are dispersed in 40ml of acetonitrile and 40ml of chloroform, the mixture is heated and refluxed to 180 ℃ under the protection of nitrogen to carry out substitution reaction for 8 hours, the mixture is cooled to room temperature, reaction liquid is poured into water, the mixture is extracted by DCM, an organic phase is dried and filtered, filtrate is concentrated under reduced pressure to be dry, and residue is separated and purified by a silica gel column to obtain 1680mg of compound JIR-LC-II-001 as a red solid.
Experimental data:
(1)1HNMR(、CDCl3)：0.75～0.89(3H,m)；1.18～1.25(2H,m)；1.63～1.66(2H,m)；1.85～1.96(2H,m)；2.36～2.82(8H,m)；6.99～7.15(2H,q)；7.36～7.51(2H,t)；7.63～7.79(2H,t)；8.33～8.55(3H,m)
it was confirmed that the substance obtained by the reaction was indeed the compound JIR-LC-II-011;
(2) glass transition temperature (DSC): 275 ℃;
(3) UV maximum absorption wavelength (DCM): 220nm,280nm and 354 nm;
(4) phosphorescent emission wavelength (DCM): 680 nm.
Example 3 preparation of Compound JPD-LC-I-001 (method one)
1.5G (0.5mmol) of compound G-2' (x is 1), 160mg (1.6mmol) of acetylacetone and 350mg (3.4mmol) of anhydrous sodium carbonate are dispersed in 30ml of ethylene glycol ether, the temperature is raised to 180 ℃ under the protection of nitrogen, stirring and refluxing are carried out for substitution reaction for 24 hours, the mixture is cooled to room temperature, filtration is carried out, a filter cake is washed by water and then dissolved by DCM, filtration is carried out, filtrate is dried and filtered, and the filtrate is concentrated under reduced pressure to dryness to obtain 300mg of compound JPD-LC-I-001 which is dark red solid.
Experimental data:
(1)1HNMR(、CDCl3): 0.81 to 1.40(13H, m); 1.53 to 1.86(8H, m); 5.75(1H, s); 7.39-7.40 (3H, m); 7.60 to 7.89(3H, m); 8.06-8.22 (3H, m). The substance obtained by the reaction was confirmed to be indeed the compound JPD-LC-I-011;
(2) glass transition temperature (DSC): 283.6 ℃;
(3) UV maximum absorption wavelength (DCM): 252nm,350nm,378 nm;
(4) phosphorescent emission wavelength (DCM): 604 nm.
From the above, the product was found to be the target compound with a correct structure.
Example 4 preparation of devices OLED-1 to OLED-3
1) The glass substrate coated with the ITO conductive layer is subjected to ultrasonic treatment in a cleaning agent for 30 minutes, washed in deionized water, subjected to ultrasonic treatment in an acetone/ethanol mixed solvent for 30 minutes, baked to be completely dry in a clean environment, irradiated by an ultraviolet light cleaning machine for 10 minutes, and bombarded on the surface by a low-energy cation beam.
2) Placing the processed ITO glass substrate in a vacuum chamber, and vacuumizing to 1 × 10-5～9×10-3Pa, continuously and respectively evaporating a compound 2T-NATA on the anode layer film to be used as a hole injection layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 40 nm;
wherein the structural formula of the 2T-NATA is as follows:
3) continuously evaporating NPB on the hole injection layer to form a hole transport layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10 nm;
wherein the structural formula of NPB is as follows:
4) a layer of compounds represented by formula I, namely JIR-LC-I-001 and CBP are continuously evaporated on the hole transport layer to be used as the light-emitting layer of the device, and the evaporation rate ratio of the compounds represented by the formula I, namely JIR-LC-I-001 to CBP obtained in example 1 is 1: 100, the dosage of the compound JIR-LC-I-001 is 5 percent of the mass of CBP, the evaporation rate is 0.1nm/s, and the film thickness of an organic luminescent layer obtained by evaporation is 50 nm;
5) continuously evaporating a layer of Alq3 material on the organic light-emitting layer to be used as an electron transport layer of the device, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 20 nm;
wherein the structural formula of Alq3 is as follows:
6) and sequentially evaporating a magnesium/silver alloy layer on the electron transport layer to serve as a cathode layer of the device, wherein the evaporation rate of the magnesium/silver alloy layer is 2.0-3.0 nm/s, the evaporation film thickness is 100nm, and the mass ratio of magnesium to silver is 1: 9, obtaining the OLED-1 provided by the invention.
By following the same procedure as above, only replacing JIR-LC-I-011 used in step 4) with the compound JIR-LC-II-001 obtained in example 2, OLED-2 provided by the present invention was obtained;
by following the same procedure as above, only replacing JIR-LC-I-011 used in step 4) with JPD-LC-I-001, a compound obtained in example 3, was provided to obtain OLED-3 provided by the present invention;
the results of the performance tests of the obtained devices OLED-1 to OLED-3 are shown in Table 1.
OLED device performance detection conditions:
luminance and chromaticity coordinates: testing with a photosresearch PR-715 spectrum scanner;
current density and lighting voltage: testing using a digital source table Keithley 2420;
power efficiency: tested using NEWPORT 1931-C.
The results of performance tests of the devices OLED-1 to OLED-3 obtained in the examples are shown in Table 1.
TABLE 1 Performance test results of OLED-1 to OLED-3
From the above, the organic electrophosphorescent light-emitting device made of the metal complex light-emitting material provided by the invention has high current density and power efficiency, and the light color is in the red light region.
Claims (10)
1. A compound of the formula I, wherein,
R1and R2Any one selected from H, F, -CN, methoxyl and trifluoromethoxy;
R3and R4Selected from any one of H and trans-cyclohexyl substituted C1-C50 aliphatic hydrocarbon radical, and R3And R4Not H at the same time;
m is iridium or platinum;
x is 1, 2 or 3;
y is 0, 1, 2 or 3; and when x is 3, y is 0;
l is an acetylacetonate group.
2. The compound of claim 1, wherein: the compound shown in the formula I is any one of the following compounds:
3. a method for preparing the compound shown as the formula I in claim 1, which is the following method I or method II;
the first method comprises the following steps:
will be provided withUniformly mixing the compound with acetylacetone and alkali in a solvent, refluxing for substitution reaction, and obtaining a compound shown in formula I with x being 1 or 2 after the reaction is finished;
the second method comprises the following steps:
will be provided withMixing them in solvent for substitution reactionAfter that, the compound shown in the formula I is obtained when x is 3;
in the first and second methods, R1-R4M is as defined in claim 1.
4. The method of claim 3, wherein: in the first method, the first step is that,the feeding molar ratio of the acetylacetone to the alkali is 1: 2-4: 2-10; in the step of substitution reaction, the temperature is 170-190 ℃; the time is 10 to 24 hours;
in the second method, the first step is that,the mass ratio of (1): 3-4;
in the step of substitution reaction, the temperature is 170-190 ℃; the time is 7-9 hours.
5. The method according to claim 3 or 4, characterized in that: the alkali is at least one of anhydrous sodium carbonate and anhydrous potassium carbonate;
the substitution reaction is carried out in an inert atmosphere; the inert atmosphere is specifically nitrogen atmosphere;
the solvent is at least one selected from ethylene glycol ethyl ether, tetrahydrofuran, n-hexane, toluene, ethanol, water, glycerol, 1, 4-dioxane, acetonitrile and chloroform.
6. A luminescent material comprising a compound of formula I according to any one of claims 1-2; or,
use of a compound of formula I according to any one of claims 1-2 for the preparation of a luminescent material.
7. The luminescent material or the application according to claim 6, wherein: the luminescent material is an organic electrophosphorescent luminescent material, in particular to an organic electrophosphorescent luminescent material with the luminescent wavelength of 460nm-680 nm.
8. Use of a compound of formula I according to any one of claims 1-2 as a light-emitting layer in the preparation of an organic electroluminescent device;
an organic electroluminescent device comprising a compound of formula I as claimed in any of claims 1 to 2 as the light-emitting layer.
9. Use or organic electroluminescent device according to claim 8, characterized in that: the organic electroluminescent device is an organic electrophosphorescent luminescent device;
the organic electroluminescent device is specifically a device composed of the following structure:
the organic light-emitting diode comprises a transparent substrate, an anode layer, a hole injection layer, a hole transport layer, an organic light-emitting layer, an electron transport layer and a cathode layer from bottom to top in sequence;
wherein, the material for forming the transparent substrate is glass or a flexible substrate;
the anode layer is made of inorganic materials or organic conducting polymers; wherein the inorganic material is indium tin oxide, zinc oxide, tin zinc oxide, gold, silver or copper; the organic conducting polymer is selected from at least one of polythiophene, sodium polyvinyl benzene sulfonate and polyaniline;
the material for forming the hole injection layer is 2T-NATA; the structural formula of the 2T-NATA is as follows:
the material constituting the hole transport layer is NPB; the structural formula of the NPB is as follows:
the material constituting the organic light-emitting layer is a compound represented by formula I according to claim 1 or 2;
the material for forming the electron transport layer is Alq3, Gaq3 or BPhen;
wherein the structural formulas of Alq3, BPhen and Gaq3 are as follows in sequence:
the cathode layer is made of a material selected from any one or two of the following elements: lithium, magnesium, silver, calcium, strontium, aluminum, indium, copper, gold, and silver.
10. Use or organic electroluminescent device according to claim 9, characterized in that: the thickness of the hole injection layer is 30nm-50 nm;
the thickness of the hole transport layer is 5nm-15 nm;
the thickness of the organic light-emitting layer is 10nm-100 nm;
the thickness of the electron transmission layer is 10nm-30 nm;
the thickness of the cathode layer is 90nm-110 nm.
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