CN114805448A - Iridium metal complex and organic electroluminescent device comprising same - Google Patents
Iridium metal complex and organic electroluminescent device comprising same Download PDFInfo
- Publication number
- CN114805448A CN114805448A CN202210441913.1A CN202210441913A CN114805448A CN 114805448 A CN114805448 A CN 114805448A CN 202210441913 A CN202210441913 A CN 202210441913A CN 114805448 A CN114805448 A CN 114805448A
- Authority
- CN
- China
- Prior art keywords
- substituted
- unsubstituted
- iridium metal
- metal complex
- organic electroluminescent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- -1 Iridium metal complex Chemical class 0.000 title claims abstract description 42
- 229910052741 iridium Inorganic materials 0.000 title claims abstract description 39
- 239000000463 material Substances 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims description 42
- 239000003446 ligand Substances 0.000 claims description 28
- 239000010410 layer Substances 0.000 claims description 24
- 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 claims description 10
- 239000002994 raw material Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 239000012044 organic layer Substances 0.000 claims description 8
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 7
- 229910052805 deuterium Inorganic materials 0.000 claims description 7
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 80
- 229910052757 nitrogen Inorganic materials 0.000 description 49
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 239000002244 precipitate Substances 0.000 description 26
- 238000010992 reflux Methods 0.000 description 18
- 238000005303 weighing Methods 0.000 description 18
- 239000003208 petroleum Substances 0.000 description 17
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 16
- 238000001035 drying Methods 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- 238000001816 cooling Methods 0.000 description 15
- 238000000967 suction filtration Methods 0.000 description 14
- 238000012360 testing method Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000001819 mass spectrum Methods 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 238000004128 high performance liquid chromatography Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000002347 injection Methods 0.000 description 9
- 239000007924 injection Substances 0.000 description 9
- 239000011259 mixed solution Substances 0.000 description 9
- 239000008213 purified water Substances 0.000 description 9
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 238000002386 leaching Methods 0.000 description 8
- 230000007935 neutral effect Effects 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- 238000001308 synthesis method Methods 0.000 description 7
- 239000002346 layers by function Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 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 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000004506 ultrasonic cleaning Methods 0.000 description 3
- MFELLNQJMHCAKI-UHFFFAOYSA-N 3,7-diethylnonane-4,6-dione Chemical compound CCC(CC)C(=O)CC(=O)C(CC)CC MFELLNQJMHCAKI-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 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 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 1
- XSUNFLLNZQIJJG-UHFFFAOYSA-N 2-n-naphthalen-2-yl-1-n,1-n,2-n-triphenylbenzene-1,2-diamine Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N(C=1C=CC=CC=1)C=1C=C2C=CC=CC2=CC=1)C1=CC=CC=C1 XSUNFLLNZQIJJG-UHFFFAOYSA-N 0.000 description 1
- MWTPXLULLUBAOP-UHFFFAOYSA-N 2-phenoxy-1,3-benzothiazole Chemical class N=1C2=CC=CC=C2SC=1OC1=CC=CC=C1 MWTPXLULLUBAOP-UHFFFAOYSA-N 0.000 description 1
- NWCVYRIJESEOMH-UHFFFAOYSA-N 3,3,7,7-tetraethylnonane-4,6-dione Chemical compound CCC(CC)(CC)C(=O)CC(=O)C(CC)(CC)CC NWCVYRIJESEOMH-UHFFFAOYSA-N 0.000 description 1
- VRXDVQSACJNKBX-UHFFFAOYSA-N 3,3,7,7-tetramethylnonane-4,6-dione Chemical compound CCC(C)(C)C(=O)CC(=O)C(C)(C)CC VRXDVQSACJNKBX-UHFFFAOYSA-N 0.000 description 1
- QCIMLTPFBSDZNO-UHFFFAOYSA-N 3,7-diethyl-3,7-dimethylnonane-4,6-dione Chemical compound CCC(C)(CC)C(=O)CC(=O)C(C)(CC)CC QCIMLTPFBSDZNO-UHFFFAOYSA-N 0.000 description 1
- OAIASDHEWOTKFL-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(4-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=C(C)C=CC=1)C1=CC=CC=C1 OAIASDHEWOTKFL-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
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 1
- 241000985284 Leuciscus idus Species 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- 229920001090 Polyaminopropyl biguanide Polymers 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000008425 anthrones Chemical class 0.000 description 1
- 150000007980 azole derivatives Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- PJVZQNVOUCOJGE-CALCHBBNSA-N chembl289853 Chemical compound N1([C@H]2CC[C@H](O2)N2[C]3C=CC=CC3=C3C2=C11)C2=CC=C[CH]C2=C1C1=C3C(=O)N(C)C1=O PJVZQNVOUCOJGE-CALCHBBNSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 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
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000008376 fluorenones Chemical class 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 150000002460 imidazoles Chemical class 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
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- ZTLUNQYQSIQSFK-UHFFFAOYSA-N n-[4-(4-aminophenyl)phenyl]naphthalen-1-amine Chemical compound C1=CC(N)=CC=C1C(C=C1)=CC=C1NC1=CC=CC2=CC=CC=C12 ZTLUNQYQSIQSFK-UHFFFAOYSA-N 0.000 description 1
- LBFXFIPIIMAZPK-UHFFFAOYSA-N n-[4-[4-(n-phenanthren-9-ylanilino)phenyl]phenyl]-n-phenylphenanthren-9-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C2=CC=CC=C2C=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C3=CC=CC=C3C=2)C=C1 LBFXFIPIIMAZPK-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011787 zinc oxide Substances 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
- 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
- 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
-
- 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)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention discloses an iridium metal complex and an organic electroluminescent device comprising the same, belonging to the technical field of chemistry and luminescent materials
Description
Technical Field
The invention relates to the technical field of organic electroluminescent materials, in particular to an iridium metal complex and an organic electroluminescent device comprising the same.
Background
In recent years, as the size of display devices is getting larger, flat display devices occupying less space are more and more required. The flat panel display device includes an organic electroluminescent device, also called an Organic Light Emitting Diode (OLED), whose technology is being developed at a great speed, and many prototypes have been disclosed.
Since the invention of organic Electroluminescent (EL) materials, the organic Electroluminescent (EL) materials have self-luminescent property and higher luminescent efficiency (up to ten thousand cd/m) 2 ) Light weight, fast response speed, wide visual angle range (up to 160 deg.), low driving voltage ((<10V) and wide working temperature range (working under the condition of-45-80 ℃), can form rigid display and can also realize flexible display, is easy to realize large-screen display, and is called as a fantasy display by people in the industry, so that the organic EL is gradually developed into the most advantageous technology in the field of new-generation flat panel display.
However, since the development of the organic EL material is restricted by factors such as efficiency and life time, the organic EL material has different transfer rates of electrons and holes, and if a suitable material is selected, the electrons and holes can be effectively transferred to the light emitting layer to balance the number of the electrons and holes, thereby effectively improving the light emitting efficiency, and therefore, it is urgently required to select a new organic material to develop a phosphorescent material meeting the practical requirement.
Disclosure of Invention
In view of the above, the present invention provides an iridium metal complex and an organic electroluminescent device including the same, and the iridium metal complex obtained by selecting a specific bidentate ligand can significantly improve the luminous efficiency and the phosphorescent lifetime of the device, reduce the driving voltage of the device, and have significant progress when used in an electroluminescent device.
In order to achieve the above purpose, the embodiments of the present invention provide the following technical solutions:
an iridium metal complex has a structural general formula shown in formula I:
wherein R is 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 12 、R 13 And R 14 Each independently selected from hydrogen, deuterium, halogen, -CH 2 F、-CHF 2 、-CF 3 Any one of cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted 5-30 membered heterocyclic group, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted 5-30 membered heteroaryl;
preferably, R 1 、R 2 、R 3 、R 4 、R 5 And R 6 Each independently selected from any one of hydrogen, deuterium, fluorine, chlorine, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C12 cycloalkyl and substituted or unsubstituted C6-C18 aryl; r 7 Selected from hydrogen, fluorine, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, and substituted or unsubstituted C6-C18 aryl; and, a first ligand L A The synthetic route of (2) is as follows:
wherein, X is preferably Cl and Br, and the catalyst in the first step is tetrakis (triphenylphosphine) palladium, tetrakis (triphenylphosphine) palladium: raw material A ═ 3 ‰ to 5 ‰): 1; anhydrous Na 2 CO 3 : raw material A ═ (3-3.5): 1; the reaction temperature is controlled between 100 ℃ and 110 ℃; second step reaction the deuterated DMSO: raw material C ═ (18-27): 1; the reaction temperature is controlled at 75-80 ℃.
Preferably, R 8 、R 9 、R 10 、R 12 、R 13 And R 14 Each independently selected from hydrogen, deuterium, halogen, -CH 2 F、-CHF 2 、-CF 3 Any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted 5-12-membered heterocyclic group, substituted or unsubstituted C6-C18 aryl, and substituted or unsubstituted 5-12-membered heteroaryl;
wherein R is 8 、R 9 、R 10 、R 12 、R 13 And R 14 Each independently selected from any one of the following structures:
R 11 selected from hydrogen, deuterium, fluoro, cyano, methyl;
further, "substituted" in the above technical scheme means that a hydrogen atom bonded to a carbon atom of a compound becomes an additional substituent, and the position of substitution is not limited as long as the position is a position at which the hydrogen atom is substituted (i.e., a position at which the substituent may be substituted), and when two or more substituents are present for substitution, the two or more substituents may be the same as or different from each other.
Preferably, the iridium metal complex is selected from any one of L-001 to L-144 in the following structure:
although specific structural formulas are listed above, the series iridium metal complexes claimed by the present invention are not limited to the above molecular structures, and other specific molecular structures can be obtained through simple transformation of the groups and substitution positions thereof disclosed by the present invention, which are not described herein in detail and fall within the scope of the present invention.
The iridium metal complex is applied to preparing an organic electroluminescent device.
Preferably, the electroluminescent device comprises: a first electrode, an organic layer, a second electrode; wherein the organic layer comprises the iridium metal complex described above.
Preferably, the organic layer includes a light emitting layer including a host material and the iridium metal complex therein.
Preferably, the mass ratio of the host material to the iridium metal complex is 90:10 to 99.5: 0.5.
Preferably, the organic layer may further include other functional layers, and the other functional layers may be specifically selected from one or more of the following functional layers: a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), a hole injection-hole transport functional layer (i.e., having both hole injection and hole transport functions), an Electron Blocking Layer (EBL), a Hole Blocking Layer (HBL), an Electron Transport Layer (ETL), an Electron Injection Layer (EIL), and an electron transport-electron injection functional layer (i.e., having both electron transport and electron injection functions). And the iridium metal complex prepared by the method disclosed by the invention can be in a single form or exist in an organic layer in a mixed manner with other substances.
Preferably, the hole injection layer is one of 2-TNATA (4,4' -tris [ 2-naphthylphenylamino ] triphenylamine), phthalocyanine and porphyrin compounds, triarylamine, conductive polymers, n-type semiconductive organic complexes and metal organic complexes, and the thickness of the hole injection layer is 10-500 nm; the hole transport layer is one of NPB (namely N, N '-diphenyl-N, N' - (1-naphthyl) -1,1 '-biphenyl-4, 4' -diamine), TPD (namely N, N '-diphenyl-N, N' - (3-methylphenyl) -1,1 '-biphenyl-4, 4' -diamine), PAPB (namely N, N '-bis (phenanthrene-9-yl) -N, N' -diphenyl benzidine) arylamine carbazole compound and indolocarbazole compound, and the thickness of the hole transport layer is 10-500 nm;
the hole blocking layer is one of BAlq, BCP and BPhen, and the thickness of the hole blocking layer is 10-500 nm;
the electron transport layer is one of Alq3, coumarin No. 6, triazole derivatives, azole derivatives, oxadiazole derivatives, imidazole derivatives, fluorenone derivatives and anthrone derivatives, and the thickness of the electron transport layer is 10-500 nm;
the electron injection layer is LiF, CsF or Li 2 O、Al 2 O 3 And MgO, the thickness of which is 0.1 to 10 nm.
Preferably, the first electrode is an anode, the kind of which is not particularly limited, and is a conventional anode well known to those skilled in the art, and more preferably, the first electrode is one of ITO (indium tin oxide), tin oxide, zinc oxide, and indium oxide, and the thickness of the first electrode is 10 to 500 nm. The second electrode is a cathode, the type of which is not particularly limited, and the second electrode is a conventional cathode known to those skilled in the art, and is more preferably one of Al, Li, Na, K, Mg, Ca, Au, Ag and Pb, and the thickness of the second electrode is 100-1000 nm;
the main material is preferably one or more of 4,4'-N, N' -biphenyl dicarbazole (CBP), octahydroxyquinoline (Alq3), metal phenoxybenzothiazole compounds, polyfluorene, aromatic condensed rings and zinc complexes. The thickness of the light emitting layer is 10 to 500 nm.
The device of the invention can be used for an organic light-emitting device, an organic solar cell, electronic paper, an organic photoreceptor or an organic thin film transistor.
According to the technical scheme, compared with the prior art, the invention has the following beneficial effects:
the iridium metal complex obtained by selecting the specific heterocyclic ligand combination has better electron receiving capacity, can improve the energy transmission between a host and an object, and is particularly characterized in that the iridium metal compound is used as a functional layer, and is particularly used as an organic electroluminescent device manufactured by a light emitting layer, the current efficiency is obviously improved, the driving voltage is obviously reduced, and the service life of the device is greatly prolonged.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments.
Example 1
The preparation method of the complex L-003 comprises the following specific steps:
L A the synthesis steps of the ligand are as follows:
the method comprises the following steps: weighing raw material A (4-chloro-7-fluorobenzo [ f ] under the protection of nitrogen]Isoquinoline, 50g, 216.42mmol), phenylboronic acid (31.69g, 259.71mmol), and anhydrous Na 2 CO 3 (80.29g, 757.47mmol) and tetrakis (triphenylphosphine) palladium (1.25g, mmol) are put into a reaction system, 500mL of toluene, 500mL of purified water and 250mL of ethanol mixed solution are added, reflux reaction is carried out at 100 ℃ for 12h under the protection of nitrogen, the system is cooled to room temperature after the reaction is stopped, standing and liquid separation are carried out, column chromatography is carried out, and petroleum ether and ethyl acetate are used as developing agents, so that the raw material C is obtained, the mass is 47.28g, and the yield is 81%;
HPLC purity: more than 99.5 percent;
mass spectrum: calculated value is 273.1; test value 272.7;
step two: weighing raw material C (47g, 172.09mmol), deuterated DMSO (260g) and sodium hydroxide (206g, 5162mmol) under a nitrogen protection system, replacing nitrogen twice, carrying out reflux reaction at 80 ℃ for 12h, cooling the system to room temperature after the reaction is stopped, standing, separating liquid, carrying out column chromatography, developing solvent dichloromethane to obtain raw material D, wherein the mass is 39.95g, and the yield is 85%;
HPLC purity: more than 99.8 percent;
mass spectrum: calculated value 84.17; the test value was 84.26.
Step three: weighing A-003(19.52g, 70.9mmol) and IrCl under the protection of nitrogen 3 ·3H 2 O (10g, 28.36mmol) is put into a reaction system, a mixed solution of 400mL of ethylene glycol ethyl ether and 200mL of purified water is added, reflux reaction is carried out for 24h at 120 ℃ under the protection of nitrogen, the system is cooled to room temperature after the reaction is stopped, precipitates are separated out, the precipitates are filtered, the anhydrous ethanol and petroleum ether are used for washing in sequence, drying is carried out under the conditions of-0.1 Mpa and 65 ℃, and a dark red powder bridging ligand B-003 with the mass of 10.56g is obtainedThe rate is 48%;
step four: weighing bridging ligand B-003(10.56g, 6.8mmol), adding anhydrous potassium carbonate (2.8g, 20.4mmol), adding 100mL of ethylene glycol ethyl ether into the system, replacing nitrogen for three times, adding 3, 7-diethyl-4, 6-nonanedione (4.33g, 20.4mmol) under nitrogen, refluxing at 120 ℃ for 15h under the protection of nitrogen, then cooling, carrying out suction filtration, sequentially leaching with ethanol and petroleum ether, drying under the conditions of-0.1 Mpa and 70 ℃, using dichloromethane as a solvent, carrying out chromatography by using a neutral alumina column, concentrating the filtrate to separate out solid, and obtaining an iridium metal compound L-003 with the mass of 6.47g and the yield of 52%; HPLC purity: more than 99.5 percent;
mass spectrum: calculated value 952.17; test value 952.33; the specific reaction principle is as follows:
example 2
The preparation method of the complex L-013 comprises the following specific steps:
L A the ligand synthesis method is the same as example 1;
step three: weighing A-013(19.52g, 70.9mmol) and IrCl under nitrogen protection system 3 ·3H 2 Adding O (10g, 28.36mmol) into a reaction system, adding a mixed solution of 400mL of ethylene glycol ethyl ether and 200mL of purified water, carrying out reflux reaction at 120 ℃ for 24h under the protection of nitrogen, cooling the system to room temperature after the reaction is stopped, separating out a precipitate, carrying out suction filtration on the precipitate, sequentially washing the precipitate with absolute ethyl alcohol and petroleum ether, and drying the precipitate at-0.1 Mpa and 70 ℃ to obtain a dark red powder bridging ligand B-013 with the mass of 10.78g and the yield of 49%;
step four: weighing bridging ligand B-013(10.78g, 6.94mmol), adding anhydrous potassium carbonate (2.87g, 20.82mmol), adding 150mL of ethylene glycol ethyl ether into the system, replacing nitrogen for three times, adding 3,3,7, 7-tetraethyl-2, 8-dimethyl nonane-4, 6-dione (6.17g, 20.82mmol) under nitrogen protection, refluxing at 120 ℃ for 20h, cooling, performing suction filtration, sequentially leaching with ethanol and petroleum ether, drying at-0.1 MPa and 70 ℃, using dichloromethane as a solvent, performing neutral alumina column chromatography, concentrating the filtrate to separate out a solid, and obtaining an iridium metal compound L-013, the mass of which is 7.9g, and the yield of which is 55%; HPLC purity: more than 99.5 percent;
mass spectrum: calculated value 1036.33; test value 1036.45;
the specific reaction principle is as follows:
example 3
The preparation method of the complex L-038 comprises the following specific steps:
L A the ligand synthesis method is the same as example 1;
step three: weighing A-038(20.78g, 70.9mmol) and IrCl under the protection of nitrogen 3 ·3H 2 Placing O (10g, 28.36mmol) into a reaction system, adding a mixed solution of 300mL of ethylene glycol ethyl ether and 100mL of purified water, carrying out reflux reaction at 120 ℃ for 12h under the protection of nitrogen, cooling the system to room temperature after the reaction is stopped, separating out a precipitate, carrying out suction filtration on the precipitate, sequentially washing the precipitate with methanol and petroleum ether, and drying the precipitate at-0.1 Mpa and 65 ℃ to obtain a dark red powder bridging ligand B-038 with the mass of 12.89g and the yield of 56%;
step four: weighing bridging ligand B-038(12.89g, 7.93mmol), adding anhydrous potassium carbonate (3.28g, 23.79mmol), adding 150mL of ethylene glycol ethyl ether into the system, replacing nitrogen for three times, adding 3,3,7, 7-tetramethylnonane-4, 6-dione (5.05g, 23.79mmol) under nitrogen, refluxing at 120 ℃ for 24 hours under the protection of nitrogen, then cooling, performing suction filtration, sequentially leaching with methanol and petroleum ether, drying at-0.1 Mpa and 70 ℃, using dichloromethane as a solvent, performing chromatography by using a neutral alumina column, concentrating the filtrate to separate out a solid, and obtaining an iridium metal compound L-038 with the mass of 9.55g and the yield of 61%; HPLC purity: more than 99.5 percent;
mass spectrum: the calculated value is 988.15; test value 988.31;
the specific reaction principle is as follows:
example 4
The preparation method of the complex L-052 comprises the following specific steps:
L A the ligand synthesis method is the same as example 1;
step three: weighing A-052(20.01g, 70.9mmol) and IrCl under the protection of nitrogen 3 ·3H 2 Placing O (10g, 28.36mmol) into a reaction system, adding a mixed solution of 300mL of ethylene glycol ethyl ether and 100mL of purified water, carrying out reflux reaction at 120 ℃ for 20h under the protection of nitrogen, cooling the system to room temperature after the reaction is stopped, separating out a precipitate, carrying out suction filtration on the precipitate, sequentially washing the precipitate with absolute ethyl alcohol and petroleum ether, and drying the precipitate under the conditions of-0.1 Mpa and 65 ℃ to obtain a dark red powder bridging ligand B-052, wherein the mass is 13.21g, and the yield is 59%;
step four: weighing bridging ligand B-052(13.21g, 8.35mmol), adding anhydrous potassium carbonate (3.45g, 25.05mmol), adding 150mL of ethylene glycol ethyl ether into the system, replacing nitrogen for three times, adding 3,3,7, 7-tetraethyl nonane-4, 6-dione (6.72g, 25.05mmol) under nitrogen, refluxing for 20 hours at 120 ℃ under the protection of nitrogen, then cooling, performing suction filtration, sequentially leaching with ethanol and petroleum ether, drying at-0.1 Mpa and 70 ℃, using dichloromethane as a solvent, performing neutral alumina column chromatography, concentrating the filtrate to separate out solid, and obtaining iridium metal compound L-052 with the mass of 8.19g and the yield of 48%; HPLC purity: more than 99.5 percent;
mass spectrum: calculated value 1022.32; test value 1022.43;
the specific reaction principle is as follows:
example 5
The preparation method of the complex L-062 comprises the following specific steps:
L A the ligand synthesis method is the same as example 1;
step three: weighing A-062 (18.68) under the protection of nitrogeng，62.39mmol)、IrCl 3 ·3H 2 Placing O (10g, 28.36mmol) into a reaction system, adding a mixed solution of 400mL of ethylene glycol ethyl ether and 200mL of purified water, refluxing and reacting at 120 ℃ for 24 hours under the protection of nitrogen, cooling the system to room temperature after the reaction is stopped, separating out a precipitate, carrying out suction filtration on the precipitate, sequentially washing with absolute ethyl alcohol and petroleum ether, and drying under the conditions of-0.1 Mpa and 70 ℃ to obtain a dark red powder bridging ligand B-062 with the mass of 14.72g and the yield of 63%;
step four: weighing a bridging ligand B-062(14.72g, 8.92mmol), adding anhydrous potassium carbonate (3.69g, 26.76mmol), adding 150mL of ethylene glycol ethyl ether into the system, replacing nitrogen for three times, adding 3,3,7, 7-tetraethyl-2, 8-dimethyl nonane-4, 6-dione (7.93g, 26.76mmol) under nitrogen protection, refluxing at 120 ℃ for 24 hours, cooling, performing suction filtration, sequentially leaching with ethanol and petroleum ether, drying under the conditions of-0.1 Mpa and 70 ℃, using dichloromethane as a solvent, performing neutral alumina column chromatography, concentrating the filtrate to separate out solid, and obtaining an iridium metal compound L-062 with the mass of 8.89g and the yield of 46%; HPLC purity: more than 99.5 percent;
mass spectrum: calculated value 1084.51; test value 1084.48;
the specific reaction principle is as follows:
example 6
The preparation method of the complex L-076 comprises the following specific steps:
L A the ligand synthesis method is the same as in example 1;
step three: weighing A-076(20.68g, 62.39mmol) and IrCl under the protection of nitrogen 3 ·3H 2 O (10g, 28.36mmol) is put into a reaction system, a mixed solution of 400mL of ethylene glycol ethyl ether and 150mL of purified water is added, reflux reaction is carried out for 24h at 120 ℃ under the protection of nitrogen, the system is cooled to room temperature after the reaction is stopped, precipitates are separated out, the precipitates are filtered, absolute ethyl alcohol and petroleum ether are used for washing in sequence, and drying is carried out under the conditions of-0.1 Mpa and 65 ℃ to obtain a dark red powder bridging ligand B076, 15.11g in mass, 60% yield;
step four: weighing bridging ligand B-076(15.11g, 8.5mmol), adding anhydrous potassium carbonate (3.5g, 25.5mmol), adding 150mL of ethylene glycol ethyl ether into the system, replacing nitrogen for three times, adding 3, 7-diethyl-3, 7-dimethyl nonane-4, 6-dione (6.13g, 25.5mmol) under nitrogen, refluxing for 12 hours at 120 ℃ under the protection of nitrogen, then cooling, performing suction filtration, sequentially leaching with ethanol and petroleum ether, drying at-0.1 Mpa and 70 ℃, using dichloromethane as a solvent, performing neutral alumina column chromatography, concentrating the filtrate to separate out solid, and obtaining iridium metal compound L-076 with the mass of 10.02g and the yield of 54%; HPLC purity: more than 99.5 percent;
mass spectrum: calculated value 1092.44; test value 1092.51;
the specific reaction principle is as follows:
example 7
The preparation method of the complex L-089 comprises the following specific steps:
L A the ligand synthesis method is the same as example 1;
step three: weighing A-089(21.3g, 62.39mmol) and IrCl under the protection of nitrogen 3 ·3H 2 Placing O (10g, 28.36mmol) into a reaction system, adding a mixed solution of 400mL of ethylene glycol ethyl ether and 200mL of purified water, carrying out reflux reaction at 120 ℃ for 24h under the protection of nitrogen, cooling the system to room temperature after the reaction is stopped, separating out a precipitate, carrying out suction filtration on the precipitate, sequentially washing the precipitate with absolute ethyl alcohol and petroleum ether, and drying the precipitate at-0.1 Mpa and 65 ℃ to obtain a dark red powder bridging ligand B-089 with the mass of 11.84g and the yield of 46%;
step four: weighing bridging ligand B-089(11.84g, 6.51mmol), adding anhydrous potassium carbonate (19.53g, 2.69mmol), adding 150mL of ethylene glycol ethyl ether into the system, replacing nitrogen for three times, adding 3, 7-diethylnonane-4, 6-dione (4.15g, 19.53mmol) under nitrogen, refluxing at 120 ℃ for 12h under the protection of nitrogen, then cooling, performing suction filtration, sequentially leaching with ethanol and petroleum ether, drying at-0.1 Mpa and 70 ℃, using dichloromethane as a solvent, performing neutral alumina column chromatography, concentrating the filtrate to separate out solid, and obtaining an iridium metal compound L-089 with the mass of 7.48g and the yield of 53%; HPLC purity: more than 99.5 percent;
mass spectrum: calculated value 1084.51; test value 1084.65;
the specific reaction principle is as follows:
example 8
The preparation method of the complex L-096 comprises the following specific steps:
L A the ligand synthesis method is the same as example 1;
step three: weighing A-096(21.79g, 70.9mmol) and IrCl under nitrogen protection system 3 ·3H 2 Placing O (10g, 28.36mmol) into a reaction system, adding a mixed solution of 400mL of ethylene glycol ethyl ether and 200mL of purified water, carrying out reflux reaction at 120 ℃ for 20h under the protection of nitrogen, cooling the system to room temperature after the reaction is stopped, separating out a precipitate, carrying out suction filtration on the precipitate, sequentially washing the precipitate with absolute ethyl alcohol and petroleum ether, and drying the precipitate at-0.1 Mpa and 65 ℃ to obtain a dark red powder bridging ligand B-096 with the mass of 13.34g and the yield of 56%;
step four: weighing bridging ligand B-096(13.34g, 7.93mmol), adding anhydrous potassium carbonate (3.28g, 23.79mmol), adding 150mL of ethylene glycol ethyl ether into the system, replacing nitrogen for three times, adding 3,3,7, 7-tetraethyl-2, 8-dimethyl nonane-4, 6-dione (7.05g, 23.79mmol) under nitrogen protection, refluxing at 120 ℃ for 24h, cooling, performing suction filtration, sequentially leaching with ethanol and petroleum ether, drying under the conditions of-0.1 Mpa and 70 ℃, using dichloromethane as a solvent, performing neutral alumina column chromatography, concentrating the filtrate to separate out solid, and obtaining iridium metal compound L-096 with mass of 8.55g and yield of 49%; HPLC purity: more than 99.5 percent;
mass spectrum: calculated value 1100.37; test value 1100.44;
the specific reaction principle is as follows:
the preparation methods of other iridium metal complexes are the same as those of the 8 listed examples, so that the preparation methods are not exhaustive, and other complexes are selected as examples, and the mass spectrum and the molecular formula of the complexes are shown in table 1:
TABLE 1 molecular formula and Mass Spectrometry of other organic Iridium Metal complexes
In addition, in order to further illustrate the application effect of the iridium metal complex prepared by the disclosure in the electroluminescent device, the inventor also performs the following test experiments, specifically as follows:
example 9 device example
An iridium metal complex type L-003 is adopted to prepare an organic electroluminescent device, and the specific process is as follows:
coating with a thickness of
The ITO glass substrate is placed in distilled water for cleaning for 2 times, ultrasonic cleaning is carried out for 30min, the ITO glass substrate is repeatedly cleaned for 2 times by distilled water, the ultrasonic cleaning is carried out for 10min, after the cleaning by distilled water is finished, isopropanol, acetone and methanol solvents are sequentially subjected to ultrasonic cleaning (each time, each time is carried out for 10min), then the ITO glass substrate is dried, transferred into a plasma cleaning machine, washed for 5min and sent into an evaporation machine;
using ITO as anode, firstly, evaporating CuPc on it
Then sequentially evaporating NPB
A mixture of a host substance 4,4'-N, N' -biphenyldicarbazole ("CBP") and a compound of formula G-4 (wherein the weight ratio of 4,4'-N, N' -biphenyldicarbazole ("CBP") to the compound L-003 is 95:5), an electron transport layer "Alq 3 ”
Electron injection layer LiF
Cathode Al
And preparing the organic electroluminescent device D-003.
Then sequentially replacing the formula L-003 with L-013, L-019, L-034, L-038, L-52, L-052, L-062, L-076, L-085, L-089, L-096, L-102, L-110, L-125, L-128, L-138 and L-144 according to the preparation scheme, and preparing the corresponding iridium metal complex organic electroluminescent devices D-013, D-019, D-034, D-038, D-52, D-052, D-062, D-076, D-085, D-089, D-096, D-102, D-110, D-125, D-128, D-138 and D-144.
Comparative example 1
An organic electroluminescent device was produced according to the same production scheme as in example 9, wherein the light-emitting layer was doped with an organometallic complex having the following structure: ir (bty) 2 acac; wherein, Ir (bty) 2 The structural formula of acac is as follows:
a comparative device E was also prepared.
Wherein the compounds used in the embodiments of the present invention are copper (II) phthalocyanine (CuPc), NPB, Alq 3 And the structural formula of CBP is as follows
And the light emitting characteristics of the resulting devices D-013, D-038, D-052, D-062, D-076, D-089, D-096 and E were tested using a KEITHLEY model 2400 source measuring unit, a CS-2000 spectroradiometer, to evaluate the driving voltage and the light emitting efficiency, and the specific test results are shown in Table 2 below:
table 2 results of measuring performance of electroluminescent devices of example 9, comparative example 1 and doped with other iridium metal complexes
From the above test results, it can be seen that Ir (bty) is provided in comparison to comparative example 1 of the device 2 The organic electroluminescent device with acac as the doping material can effectively reduce the driving voltage of the organic electroluminescent device, and can remarkably improve the current efficiency and the service life of the organic electroluminescent device. In light of the foregoing description of the preferred embodiment of the present invention, many modifications and variations will be apparent to those skilled in the art without departing from the spirit and scope of the invention. The technical scope of the present invention is not limited to the content of the specification, and must be determined according to the scope of the claims.
Claims (6)
1. An iridium metal complex is characterized in that the structural general formula of the iridium metal complex is shown as formula I:
wherein R is 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 12 、R 13 And R 14 Each independently selected from hydrogen, deuterium, halogen, -CH 2 F、-CHF 2 、-CF 3 Any one of cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted 5-30 membered heterocyclic group, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted 5-30 membered heteroaryl.
2. An iridium metal complex according to claim 1 wherein R is 1 、R 2 、R 3 、R 4 、R 5 And R 6 Each independently selected from any one of hydrogen, deuterium, fluorine, chlorine, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C12 cycloalkyl and substituted or unsubstituted C6-C18 aryl;
R 7 selected from hydrogen, fluorine, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, and substituted or unsubstituted C6-C18 aryl.
3. An iridium metal complex according to claim 1 or 2 wherein the first ligand L A The synthetic route of (2) is as follows:
wherein, X is preferably Cl and Br, and the catalyst in the first step is tetrakis (triphenylphosphine) palladium, tetrakis (triphenylphosphine) palladium: raw material A ═ 3 ‰ to 5 ‰): 1; anhydrous Na 2 CO 3 : raw material A ═ (3-3.5): 1; the reaction temperature is controlled between 100 ℃ and 110 ℃; second step reaction the deuterated DMSO: raw material C ═ (18-27): 1; the reaction temperature is controlled at 75-80 ℃.
4. An iridium metal complex according to claim 1 wherein R is 8 、R 9 、R 10 、R 12 、R 13 And R 14 Each independently selected from any one of the following structures:
R 11 selected from hydrogen, deuterium, fluoro, cyano, methyl.
5. An organic electroluminescent device, comprising: a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, the organic layer comprising the iridium metal complex of claim 1.
6. An organic electroluminescent device according to claim 5, wherein the organic layer comprises a light-emitting layer; the light emitting layer comprises a host material and the iridium metal complex;
wherein the mass ratio of the main material to the iridium metal complex is 90: 10-99.5: 0.5.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210441913.1A CN114805448B (en) | 2022-04-25 | 2022-04-25 | Iridium metal complex and organic electroluminescent device comprising iridium metal complex |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210441913.1A CN114805448B (en) | 2022-04-25 | 2022-04-25 | Iridium metal complex and organic electroluminescent device comprising iridium metal complex |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN114805448A true CN114805448A (en) | 2022-07-29 |
| CN114805448B CN114805448B (en) | 2024-03-29 |
Family
ID=82508597
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202210441913.1A Active CN114805448B (en) | 2022-04-25 | 2022-04-25 | Iridium metal complex and organic electroluminescent device comprising iridium metal complex |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114805448B (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114736244A (en) * | 2022-05-05 | 2022-07-12 | 吉林奥来德光电材料股份有限公司 | Organic phosphorus luminescent material and preparation method and application thereof |
| CN114891042A (en) * | 2022-05-18 | 2022-08-12 | 吉林奥来德光电材料股份有限公司 | Organic metal compound and application thereof, luminescent device and luminescent device |
| CN115819467A (en) * | 2022-12-15 | 2023-03-21 | 吉林奥来德光电材料股份有限公司 | Organometallic compound, application thereof, organic electroluminescent device containing organometallic compound and light-emitting device |
| CN116199723A (en) * | 2023-05-05 | 2023-06-02 | 吉林奥来德光电材料股份有限公司 | Phosphorescent doped material with pyridyl aza-dibenzofuran ligand and application thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014115528A1 (en) * | 2013-01-22 | 2014-07-31 | Canon Kabushiki Kaisha | Iridium complex and organic light-emitting device including the same |
| WO2014123239A1 (en) * | 2013-02-06 | 2014-08-14 | Canon Kabushiki Kaisha | Organic light-emitting device and display apparatus |
| CN111747990A (en) * | 2019-03-29 | 2020-10-09 | 三星电子株式会社 | Organometallic compound, organic light emitting device including the same, and diagnostic composition including the same |
-
2022
- 2022-04-25 CN CN202210441913.1A patent/CN114805448B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014115528A1 (en) * | 2013-01-22 | 2014-07-31 | Canon Kabushiki Kaisha | Iridium complex and organic light-emitting device including the same |
| US20150364702A1 (en) * | 2013-01-22 | 2015-12-17 | Canon Kabushiki Kaisha | Iridium complex and organic light-emitting device including the same |
| WO2014123239A1 (en) * | 2013-02-06 | 2014-08-14 | Canon Kabushiki Kaisha | Organic light-emitting device and display apparatus |
| CN111747990A (en) * | 2019-03-29 | 2020-10-09 | 三星电子株式会社 | Organometallic compound, organic light emitting device including the same, and diagnostic composition including the same |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114736244A (en) * | 2022-05-05 | 2022-07-12 | 吉林奥来德光电材料股份有限公司 | Organic phosphorus luminescent material and preparation method and application thereof |
| CN114736244B (en) * | 2022-05-05 | 2024-02-23 | 吉林奥来德光电材料股份有限公司 | Organic iridium luminescent material and preparation method and application thereof |
| CN114891042A (en) * | 2022-05-18 | 2022-08-12 | 吉林奥来德光电材料股份有限公司 | Organic metal compound and application thereof, luminescent device and luminescent device |
| CN115819467A (en) * | 2022-12-15 | 2023-03-21 | 吉林奥来德光电材料股份有限公司 | Organometallic compound, application thereof, organic electroluminescent device containing organometallic compound and light-emitting device |
| CN116199723A (en) * | 2023-05-05 | 2023-06-02 | 吉林奥来德光电材料股份有限公司 | Phosphorescent doped material with pyridyl aza-dibenzofuran ligand and application thereof |
| CN116199723B (en) * | 2023-05-05 | 2023-10-13 | 吉林奥来德光电材料股份有限公司 | Phosphorescent doped material with pyridyl aza-dibenzofuran ligand and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN114805448B (en) | 2024-03-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP6978105B2 (en) | A metal complex containing a cyano-substituted ligand, an electroluminescent device containing the metal complex, and a formulation containing the metal complex. | |
| JP7011333B2 (en) | Organic luminescent material containing a novel co-ligand | |
| KR101996649B1 (en) | Pyrene derivative compounds and organic light-emitting diode including the same | |
| KR101161290B1 (en) | Fused aromatic compound and organic electroluminescent device using the same | |
| KR101923936B1 (en) | New compounds and organic light-emitting diode including the same | |
| KR101825381B1 (en) | spiro compounds and organic light-emitting diode including the same | |
| CN114805448B (en) | Iridium metal complex and organic electroluminescent device comprising iridium metal complex | |
| KR101759482B1 (en) | Heterocyclic compounds and organic light-emitting diode including the same | |
| KR101861263B1 (en) | Anthracene deriva tives and organic light-emitting diode including the same | |
| CN111808142A (en) | Organic phosphorus luminescent compound and preparation method and application thereof | |
| KR101791022B1 (en) | spiro compounds and organic light-emitting diode including the same | |
| KR102576605B1 (en) | Organic electroluminescent material and its device | |
| KR20110123701A (en) | Anthracene-based compound and organic electroluminescent devices comprising the same | |
| KR20110041725A (en) | Aromatic compound and organic electroluminescent device using the same | |
| KR20110113468A (en) | Heterocyclic compounds and organic light-emitting diode including the same | |
| KR20220115778A (en) | Organic electroluminescent material and device thereof | |
| CN112010908B (en) | Iridium complex for red light electroluminescent material, preparation method thereof and photoelectric device | |
| KR101791023B1 (en) | Fused aromatic compound and organic electroluminescent devices comprising the same | |
| KR102505667B1 (en) | A phosphorescent organic metal complex and use thereof | |
| KR20220081934A (en) | Phosphorescent organometallic complex and device thereof | |
| CN111808143A (en) | Metal complex containing adamantane structure, preparation method thereof and photoelectric device | |
| KR20220115780A (en) | Organic electroluminescent material and device thereof | |
| KR101779915B1 (en) | Fused arylamine compound and organic electroluminescent devices comprising the same | |
| KR101809898B1 (en) | Heteroaryl amine derivatives and organic light-emitting diode including the same | |
| KR102004385B1 (en) | New compounds and organic light-emitting diode including the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |