CN111777645A - Metal complex for red light electroluminescent material and preparation method and device thereof - Google Patents
Metal complex for red light electroluminescent material and preparation method and device thereof Download PDFInfo
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- 239000000463 material Substances 0.000 title claims abstract description 76
- 150000004696 coordination complex Chemical class 0.000 title claims abstract description 69
- 238000002360 preparation method Methods 0.000 title abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 16
- -1 nitro, amino, hydroxyl Chemical group 0.000 claims abstract description 16
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 7
- 229910052805 deuterium Inorganic materials 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- 150000001345 alkine derivatives Chemical class 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 239000010410 layer Substances 0.000 claims description 37
- 239000003446 ligand Substances 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 229910052751 metal Inorganic materials 0.000 claims description 11
- 239000002184 metal Substances 0.000 claims description 11
- 239000012044 organic layer Substances 0.000 claims description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 7
- 229940126062 Compound A Drugs 0.000 claims description 4
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 239000012298 atmosphere Substances 0.000 claims description 4
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 230000001681 protective effect Effects 0.000 claims description 4
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 claims description 4
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 229910021638 Iridium(III) chloride Inorganic materials 0.000 claims description 2
- AEDZKIACDBYJLQ-UHFFFAOYSA-N ethane-1,2-diol;hydrate Chemical compound O.OCCO AEDZKIACDBYJLQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000012046 mixed solvent Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 229910052711 selenium Inorganic materials 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- 239000012299 nitrogen atmosphere Substances 0.000 description 23
- 229910052757 nitrogen Inorganic materials 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 238000012360 testing method Methods 0.000 description 18
- 238000000967 suction filtration Methods 0.000 description 16
- 239000007787 solid Substances 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 238000001035 drying Methods 0.000 description 12
- 238000002347 injection Methods 0.000 description 12
- 239000007924 injection Substances 0.000 description 12
- 238000005406 washing Methods 0.000 description 12
- 230000001376 precipitating effect Effects 0.000 description 10
- 239000002346 layers by function Substances 0.000 description 8
- 238000001819 mass spectrum Methods 0.000 description 7
- 238000000921 elemental analysis Methods 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 239000008213 purified water Substances 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000001514 detection method Methods 0.000 description 5
- 230000005525 hole transport Effects 0.000 description 5
- 238000002386 leaching Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 101100490051 Lactococcus lactis subsp. lactis (strain IL1403) accD gene Proteins 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000758 substrate 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
- 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
- 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
- KDOQMLIRFUVJNT-UHFFFAOYSA-N 4-n-naphthalen-2-yl-1-n,1-n-bis[4-(n-naphthalen-2-ylanilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=C2C=CC=CC2=CC=1)C1=CC=C(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=C1 KDOQMLIRFUVJNT-UHFFFAOYSA-N 0.000 description 1
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 1
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920001090 Polyaminopropyl biguanide Polymers 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- 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
- 238000004140 cleaning Methods 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 238000001704 evaporation 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
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 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
- 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
- 238000005457 optimization Methods 0.000 description 1
- 150000004866 oxadiazoles Chemical class 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
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 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
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 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
- 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
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
-
- 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)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention discloses a metal complex for a red light electroluminescent material, and a preparation method and a device thereof, belonging to the technical field of luminescent materials, wherein the metal complex has a structural general formula as follows:
in the formula, R1～R13Independently represent hydrogen, deuterium, nitro, amino, hydroxyl, halogen, cyano, sulfydryl, adamantane, substituted or unsubstituted alkyl of C1-C30, substituted or unsubstituted alkoxy of C1-C20, substituted or unsubstituted alkylene of C2-C10, substituted or unsubstituted alkyne of C2-C10, substituted or unsubstitutedAt least one substituted C6-C30 aryl group, substituted or unsubstituted C2-C30 aromatic heterocyclic group; and R is1～R10At least one of which is adamantane. The device containing the metal complex has higher current efficiency and longer service life.
Description
Technical Field
The invention relates to the technical field of luminescent materials, in particular to a metal complex for a red light electroluminescent material, and a preparation method and a device thereof.
Background
In 1987, doctor Deng Qingyun reported an electroluminescent diode technology based on organic luminescent materials, and mainly adopts a vacuum evaporation mode to prepare a double-layer device with a transmission layer and a luminescent layer, so that the quantum efficiency is improved to 1%, and the quantum efficiency can reach 1000cd/m under the working voltage lower than 10V2The brightness of the organic electroluminescent device is attracted by the wide attention of scientific enthusiasts in the world, and the organic electroluminescent technology is pushed to move to the practical stage. Electroluminescent devices have an all-solid-state structure, and organic electroluminescent materials are the core and foundation of the device. The development of new materials is a source for promoting the continuous progress of the electroluminescent technology. The preparation of the original material and the optimization of the device are also the research hotspots of the organic electroluminescent industry at present.
The phosphorescence emission phenomenon has been pursued since the discovery, and since the current efficiency of the phosphorescence material is obviously higher than that of the fluorescence current, theoretically, the current efficiency can reach 100%, many scientific research institutions are increasing the research and development of the phosphorescence material, and try to accelerate the industrialization development through the phosphorescence material. However, the phosphor material has high synthesis cost, high synthesis process requirement, high purification requirement and low efficiency, and is easy to pollute the environment in the synthesis process. Accordingly, the prior art is yet to be improved and developed.
Disclosure of Invention
An object of the embodiments of the present invention is to provide a metal complex for a red electroluminescent material, so as to solve the problems mentioned in the background art.
In order to achieve the above purpose, the embodiments of the present invention provide the following technical solutions:
a metal complex for a red light electroluminescent material has a general formula of formula I:
in the formula, R1～R13Each independently is at least one of hydrogen, deuterium, nitro, amino, hydroxyl, halogen, cyano, sulfydryl, adamantane, substituted or unsubstituted alkyl of C1-C30, substituted or unsubstituted alkoxy of C1-C20, substituted or unsubstituted alkylene of C2-C10, substituted or unsubstituted alkyne of C2-C10, substituted or unsubstituted aryl of C6-C30 and substituted or unsubstituted aromatic heterocyclic group of C2-C30; and R is1～R10At least one of which is adamantane.
Preferably, the alkyl is selected from alkyl with 1-8 carbon atoms; the alkoxy is selected from alkoxy with 1-8 carbon atoms; the alkylene is selected from alkylene with 2-6 carbon atoms; the alkynyl is selected from alkynyl with 2-6 carbon atoms; the aryl is selected from aryl with 6-18 carbon atoms; the aromatic heterocyclic group is selected from aromatic heterocyclic groups with 3-12 carbon atoms.
Preferably, the alkyl group is selected from a linear alkyl group, a branched alkyl group, a cyclic alkyl group, a linear alkyl group substituted with at least one substituent, a branched alkyl group substituted with at least one substituent, or a cyclic alkyl group substituted with at least one substituent, wherein the substituents are independently selected from at least one of deuterium, nitro, amino, hydroxyl, halogen, cyano, carbonyl, and mercapto;
the aromatic heterocyclic group is independently selected from an unsubstituted aromatic heterocyclic group or an aromatic heterocyclic group having at least one substituent, wherein the substituent is independently selected from at least one of deuterium, nitro, amino, hydroxyl, halogen, cyano, carbonyl, and mercapto.
Preferably, the heterocyclic group of the aromatic heterocyclic groups contains at least one heteroatom of N, O, P, S, Si and Se.
Preferably, a heterocyclic group of the aromatic heterocyclic groups contains at least one heteroatom of N, O and S.
Preferably, R8And R10Are all methyl.
Preferably, in the formula, the left side of metal Ir is an auxiliary ligand, and the right side of the metal Ir is a main ligand; the primary ligand is selected from any one of the following structural formulas:
preferably, the chemical structural formula of the metal complex is any one of formula L001 to formula L090:
another object of an embodiment of the present invention is to provide a method for preparing the above metal complex, which includes the following steps:
taking a compound A with a structural general formula of A and a compound C with a structural general formula of C:
under a protective atmosphere, adding the compound A and iridium trichloride into a mixed solvent of ethylene glycol ethyl ether and water for heating reaction to obtain a bridging ligand B;
and mixing the bridging ligand B with the compound C, adding ethylene glycol ethyl ether and potassium carbonate, and reacting in a protective atmosphere to obtain the metal complex.
Specifically, the synthetic route of the steps is as follows:
wherein R1 to R13 are as defined above for formula I.
It is another object of an embodiment of the present invention to provide an organic electroluminescent device, which includes a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, the organic layer including the metal complex described above.
Preferably, the organic layer includes a light emitting layer; the light-emitting layer comprises a host material and a doping material; the doping material partially or entirely contains the metal complex.
Specifically, the first electrode is an anode, and the kind thereof is not particularly limited, and may be a conventional anode known to those skilled in the art, and is more preferably one of ITO (indium tin oxide), tin oxide, zinc oxide, and indium oxide. The second electrode is a cathode, and the kind thereof is not particularly limited, and may be a conventional cathode known to those skilled in the art, and more preferably one of Al, Li, Na, K, Mg, Ca, Au, Ag, and Pb.
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 mass ratio of the doping material in the light-emitting layer is preferably 0.5% to 10%.
In addition, 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).
The kind of each functional layer is not particularly limited, and may be a conventional functional layer known to those skilled in the art. Preferably: the hole injection layer is one of 2-TNATA (namely N1- (2-naphthyl) -N4, N4-di (4- (2-naphthyl (phenyl) amino) phenyl) -N1-phenyl benzene-1, 4-diamine), phthalocyanine and porphyrin compounds, starburst triarylamine, conductive polymer, N-type semiconductive organic complex and metal organic complex; 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; the hole blocking layer is one of BAlq, BCP and BPhen; the electron transport layer is one of Alq3, coumarin No. 6, triazole derivatives, azole derivatives, oxadiazole derivatives, imidazole derivatives, fluorenone derivatives and anthrone derivatives; the electron injection layer is LiF, CsF or Li2O、Al2O3And MgO. In the embodiment of the present invention, the light emitting layer and other various functional layers may be formed by vapor deposition.
Compared with the prior art, the embodiment of the invention has the beneficial effects that:
according to the metal complex for the red light electroluminescent material, provided by the embodiment of the invention, the transition metal iridium is combined with the specific heterocyclic ligand and is combined with the adamantyl group with a rigid structure and a larger volume, so that the current efficiency of the organic electroluminescent device can be obviously improved, and the service life of the organic electroluminescent device can be 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.
Materials example 1
The embodiment of the material provides a metal complex for a red light electroluminescent material, the chemical structural formula of the metal complex is formula L001 in the summary of the invention, and the reaction route of the preparation method of the metal complex is as follows:
the specific preparation method comprises the following steps:
s1, replacing the reactor with nitrogen, and adding the compound A-001(85.2mmol, 30.11g) and IrCl into the reactor under the nitrogen atmosphere3·3H2O (28.4mmol, 10g), 600mL of ethylene glycol ethyl ether and 200mL of purified water are placed under nitrogen atmosphere for reflux for 24 hours to carry out heating reaction, then the mixture is cooled to room temperature, precipitates are separated out, solid is obtained by suction filtration, and the solid is leached by 50mL of water, 50mL of absolute ethyl alcohol and 50mL of petroleum ether in sequence and dried to obtain red powdery bridging ligand B-001(16.15g, the yield is 61%).
S2, replacing the reactor with nitrogen, adding the bridged ligand B-001(8mmol, 14.92g) and the compound C-001(24mmol, 2.37g) into the reactor under nitrogen atmosphere, adding 270mL of ethylene glycol ethyl ether and potassium carbonate (11.04g) into the system, placing the system under nitrogen atmosphere, stirring for 24 hours at 120 ℃, performing reaction, performing suction filtration, washing with alcohol, drying, performing silica gel column chromatography by using dichloromethane as an eluent, concentrating the filtrate, precipitating a solid, and performing suction filtration to finally obtain a red metal complex L001(8.13g, the yield is 51%, and the Mw is 997.24).
The detection and analysis of the metal complex L001 have the following specific results:
mass spectrum: calculated value 996.33; the test value was 997.24.
Elemental analysis:
the calculated values are: c: 68.72 percent; h: 5.97 percent; n: 2.81 percent; o: 3.21 percent; ir: 19.29 percent;
the test values are: c: 68.73 percent; h: 5.96 percent; n: 2.80 percent; o: 3.22 percent; ir: 19.29 percent.
By comparing the calculated values with the test values, the measured values are substantially consistent with the theoretical values, thereby proving that the metal complex with the structural formula of L001 can be successfully synthesized by the material examples.
Material example 2
The embodiment of the material provides a metal complex for a red light electroluminescent material, the chemical structural formula of the metal complex is represented by formula L017 in the summary of the invention, and the reaction route of the preparation method of the metal complex is as follows:
the specific preparation method comprises the following steps:
s1, replacing the reactor with nitrogen, and adding the compound A-017(85.2mmol, 31.31g) and IrCl into the reactor under the nitrogen atmosphere3·3H2Placing O (28.4mmol, 10g), 600mL of ethylene glycol ethyl ether and 200mL of purified water under nitrogen atmosphere for refluxing for 24 hours for heating reaction, then cooling to room temperature, precipitating, filtering to obtain a solid, leaching with 50mL of water, 50mL of absolute ethyl alcohol and 50mL of petroleum ether in sequence, and drying to obtain red powdered bridged ligand B-017(17.46g, the yield is 64%).
S2, replacing the reactor with nitrogen, adding the bridged ligand B-017(8mmol, 15.37g) and the compound C-017(24mmol, 3.72g) into the reactor under the nitrogen atmosphere, adding 270mL of ethylene glycol ethyl ether and potassium carbonate (11.04g) into the system, placing the system under the nitrogen atmosphere, stirring for 24 hours at 120 ℃, performing reaction, performing suction filtration, alcohol washing, drying, performing silica gel column chromatography by using dichloromethane as an eluent, concentrating the filtrate, precipitating a solid, and performing suction filtration to finally obtain a red metal complex L017(8.31g, the yield is 48%, and the MW: 1081.97).
The detection and analysis of the metal complex L017 have the following specific results:
mass spectrum: calculated value 1080.49; the test value was 1081.31.
Elemental analysis:
the calculated values are: c: 70.03 percent; h: 6.62 percent; n: 2.59 percent; o: 2.96 percent; ir: 17.79 percent;
the test values are: c: 70.04 percent; h: 6.63 percent; n: 2.58 percent; o: 2.97 percent; ir: 17.78 percent.
By comparing the calculated value with the tested value, the measured value is basically consistent with the theoretical value, thereby proving that the metal complex with the structural formula of L017 can be successfully synthesized by the material example.
Material example 3
The embodiment of the material provides a metal complex for a red light electroluminescent material, the chemical structural formula of the metal complex is shown as formula L032 in the invention content, and the reaction route of the preparation method of the metal complex is as follows:
the specific preparation method comprises the following steps:
s1, replacing the reactor with nitrogen, and adding the compound A-032(85.2mmol, 32.50g) and IrCl into the reactor under the nitrogen atmosphere3·3H2Placing O (28.4mmol, 10g), 600mL of ethylene glycol ethyl ether and 200mL of purified water under nitrogen atmosphere for refluxing for 24 hours to carry out heating reaction, then cooling to room temperature, precipitating, carrying out suction filtration to obtain a solid, sequentially leaching with 50mL of water, 50mL of absolute ethyl alcohol and 50mL of petroleum ether, and drying to obtain red powdered bridged ligand B-032(16.56g, the yield is 59%).
S2, replacing the reactor with nitrogen, adding the bridged ligand B-032(8mmol, 15.82g) and the compound C-032(24mmol, 4.39g) into the reactor under nitrogen atmosphere, adding 270mL of ethylene glycol ethyl ether and potassium carbonate (11.04g) into the system, placing the system under nitrogen atmosphere, stirring for 24 hours at 120 ℃, performing reaction, performing suction filtration, alcohol washing, drying, performing silica gel column chromatography by using dichloromethane as an eluent, concentrating the filtrate, precipitating a solid, and performing suction filtration to finally obtain a red metal complex L032(8.63g, the yield is 47.5%, and the MW: 1137.10).
The detection and analysis of the metal complex L032 are carried out, and the specific results are as follows:
mass spectrum: calculated value 1136.60; the test value was 1137.11.
Elemental analysis:
the calculated values are: c: 70.80 percent; h: 7.01 percent; n: 2.46 percent; o: 2.82 percent; ir: 16.91 percent;
the test values are: c: 70.81 percent; h: 7.02 percent; n: 2.45 percent; o: 2.81 percent; ir: 16.91 percent.
By comparing the calculated value with the tested value, the measured value is basically consistent with the theoretical value, thereby proving that the metal complex with the structural formula of L032 can be successfully synthesized by the material example.
Material example 4
The embodiment of the material provides a metal complex for a red light electroluminescent material, the chemical structural formula of the metal complex is shown as formula L047 in the invention, and the reaction route of the preparation method of the metal complex is as follows:
the specific preparation method comprises the following steps:
s1, replacing the reactor with nitrogen, and adding the compound A-047(85.2mmol, 34.89g) and IrCl into the reactor under the nitrogen atmosphere3·3H2Placing O (28.4mmol, 10g), 600mL of ethylene glycol ethyl ether and 200mL of purified water under nitrogen atmosphere for refluxing for 24 hours to carry out heating reaction, then cooling to room temperature, precipitating, carrying out suction filtration to obtain a solid, sequentially leaching with 50mL of water, 50mL of absolute ethyl alcohol and 50mL of petroleum ether, and drying to obtain red powdery bridging ligand B-047(19.28g, yield 65%).
S2, replacing a reactor with nitrogen, adding the bridged ligand B-047(8mmol, 16.71g) and the compound C-047(24mmol, 4.06g) into the reactor under the nitrogen atmosphere, adding 270mL of ethylene glycol ethyl ether and potassium carbonate (11.04g) into the system, placing the system under the nitrogen atmosphere, stirring for 24 hours at 120 ℃, performing reaction, performing suction filtration, alcohol washing, drying, performing silica gel column chromatography by using dichloromethane as an eluent, concentrating the filtrate, precipitating a solid, and performing suction filtration to finally obtain a red metal complex L047(10.30g, the yield is 54%, and the Mw: 1193.65).
The detection and analysis are carried out on the metal complex L047, and the specific results are as follows:
mass spectrum: calculated value 1192.71; the test value was 1193.65.
Elemental analysis:
the calculated values are: c: 71.50 percent; h: 7.35 percent; n: 2.35 percent; o: 2.68 percent; ir: 16.12 percent;
the test values are: c: 71.51 percent; h: 7.34 percent; n: 2.34 percent; o: 2.67 percent; ir: 16.13 percent.
By comparing the calculated value with the tested value, the measured value is basically consistent with the theoretical value, thereby proving that the metal complex with the structural formula of L047 can be successfully synthesized by the material example.
Material example 5
The embodiment of the material provides a metal complex for a red light electroluminescent material, the chemical structural formula of the metal complex is a formula L063 in the invention content, and the reaction route of the preparation method of the metal complex is as follows:
the specific preparation method comprises the following steps:
s1, replacing the reactor with nitrogen, and adding the compound A-063(85.2mmol, 30.11g) and IrCl into the reactor under the nitrogen atmosphere3·3H2Placing O (28.4mmol, 10g), 600mL of ethylene glycol ethyl ether and 200mL of purified water under nitrogen atmosphere for refluxing for 24 hours for heating reaction, then cooling to room temperature, precipitating, filtering to obtain a solid, leaching with 50mL of water, 50mL of absolute ethyl alcohol and 50mL of petroleum ether in sequence, and drying to obtain a red powdery bridging ligand B-063 (1-1)6.42g, 62% yield).
S2, replacing the reactor with nitrogen, adding the bridging ligand B-063(8mmol, 14.92g) and the compound C-063(24mmol, 2.52g) into the reactor under nitrogen atmosphere, adding 270mL of ethylene glycol ethyl ether and potassium carbonate (11.04g) into the system, placing the system under nitrogen atmosphere, stirring for 24 hours at 120 ℃, performing reaction, performing suction filtration, alcohol washing, drying, performing silica gel column chromatography by using dichloromethane as an eluent, concentrating the filtrate, precipitating a solid, and performing suction filtration to finally obtain a red metal complex L063(7.98g, yield 49.8%, Mw: 1003.24).
The detection and analysis of the metal complex L063 have the following specific results:
mass spectrum: calculated value 1002.36; the test value was 1003.24.
Elemental analysis:
the calculated values are: c: 68.30 percent; h: 6.54 percent; n: 2.79 percent; o: 3.19 percent; ir: 19.18 percent;
the test values are: c: 68.31 percent; h: 6.53 percent; n: 2.78 percent; o: 3.18 percent; ir: 19.19 percent.
By comparing the above calculated values with the test values, the measured values are substantially in agreement with the theoretical values, thereby demonstrating that the metal complex of the formula L063 can be successfully synthesized by the above material examples.
Material example 6
The embodiment of the material provides a metal complex for a red light electroluminescent material, the chemical structural formula of the metal complex is shown as formula L076 in the invention, and the reaction route of the preparation method of the metal complex is as follows:
the specific preparation method comprises the following steps:
s1, replacing the reactor with nitrogen, and adding the compound A-076(85.2mmol, 22.94g) and IrCl into the reactor under the nitrogen atmosphere3·3H2O (28.4mmol, 10g), 600mL ethylene glycol ethyl ether and 200mL purified water, placed under nitrogen atmosphereHeating the mixture for 24 hours, cooling the mixture to room temperature, separating out a precipitate, performing suction filtration to obtain a solid, sequentially leaching the solid with 50mL of water, 50mL of absolute ethyl alcohol and 50mL of petroleum ether, and drying the solid to obtain red powdery bridging ligand B-076(16.68g, the yield is 63%).
S2, replacing the reactor with nitrogen, adding the bridged ligand B-076(8mmol, 14.92g) and the compound C-076(24mmol, 5.74g) into the reactor under nitrogen atmosphere, adding 270mL of ethylene glycol ethyl ether and potassium carbonate (11.04g) into the system, placing the system under nitrogen atmosphere, stirring for 24 hours at 120 ℃, performing reaction, performing suction filtration, alcohol washing, drying, performing silica gel column chromatography by using dichloromethane as an eluent, concentrating the filtrate, precipitating a solid, and performing suction filtration to finally obtain a red metal complex L076(8.78g, 48.3% of yield and 1137.41).
The metal complex L076 is detected and analyzed, and the specific results are as follows:
mass spectrum: calculated value 1136.60; the test value was 1137.41.
Elemental analysis:
the calculated values are: c: 70.80 percent; h: 7.01 percent; n: 2.46 percent; o: 2.82 percent; ir: 16.91 percent;
the test values are: c: 70.81 percent; h: 7.02 percent; n: 2.45 percent; o: 2.81 percent; ir: 16.92 percent.
By comparing the calculated values with the test values, the measured values are substantially consistent with the theoretical values, thereby proving that the metal complex with the structural formula of L076 can be successfully synthesized by the material examples.
The synthetic routes and principles of the preparation methods of other metal complexes with the structural general formula of formula I in the summary of the invention are the same as those of the material example 1 listed above, so that the description is not exhaustive, and a plurality of metal complexes are selected as material examples 7-16 in the invention, and are specifically shown in the following table 1.
TABLE 1
| Examples of materials | Metal complexes | Molecular formula | Calculated mass spectrum | Mass spectrometric test values |
| Material example 7 | L005 | C57H59IrN2O2 | 996.33 | 997.56 |
| Material example 8 | L007 | C57H53 D6IrN2O2 | 1002.36 | 1003.16 |
| Material example 9 | L015 | C59H63IrN2O2 | 1024.38 | 1025.18 |
| Material example 10 | L018 | C61H67IrN2O2 | 1052.44 | 1053.76 |
| Material example 11 | L031 | C63H71IrN2O2 | 1080.49 | 1081.52 |
| Material example 12 | L055 | C63H71IrN2O2 | 1080.49 | 1081.28 |
| Material example 13 | L066 | C57H47D6F6IrN2O2 | 1110.31 | 1111.36 |
| Material example 14 | L068 | C57H53 D6IrN2O2 | 1002.46 | 1003.56 |
| Material example 15 | L082 | C67H73D6IrN2O2 | 1142.63 | 1143.25 |
| Material example 16 | L086 | C67H73F6IrN2O2 | 1244.54 | 1244.31 |
The embodiment of the invention also provides a device prepared by using the metal complex provided by the embodiment, and particularly, the device is an organic electroluminescent device, wherein the organic electroluminescent device comprises a first electrode, a second electrode and at least one organic layer arranged between the first electrode and the second electrode.
The organic layer may include at least one of a hole injection layer, a hole transport layer, a composite layer of hole injection and hole transport technical layers, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, an electron transport layer, and a composite layer of electron injection technical layers, and at least one of the layers may or may not include the metal complex.
Specifically, the light-emitting layer includes a host material and a dopant material; wherein, the main material can be 4, 4 '-N, N' -biphenyl dicarbazole, but is not limited to the above; the doping material may be selected from the above-mentioned metal complexes.
In practical applications, the method for manufacturing the organic electroluminescent device can refer to device example 1 below.
Device example 1
The device embodiment 1 provides an organic electroluminescent device, and a manufacturing method thereof includes the steps of:
s1, coating the coating with the thickness of
ITO glass substrateWashing with distilled water for 2 times, ultrasonic washing for 30 minutes, repeatedly washing with distilled water for 2 times, ultrasonic washing for 10 minutes, after the washing with distilled water is completed, sequentially ultrasonic washing with solvents such as isopropyl alcohol, acetone, methanol, etc., drying, transferring to a plasma cleaning machine, washing the substrate for 5 minutes, and transferring to a deposition machine for deposition.
S2, first, vapor-depositing an ITO glass substrate (anode)
Then, sequentially evaporating
Host material 4, 4 '-N, N' -biphenyldicarbazole ("CBP") and dopant material (metal complex L001 described above) were as follows 95: 5 weight ratio of the mixed mixture
Electron transport layer
Electron injection layer
Cathode electrode
Thus obtaining the organic electroluminescent device.
Device examples 2 to 16
Device embodiments 2 to 16 are prepared by referring to the preparation method provided in device embodiment 1, except that the doping material metal complex L001 in device embodiment 1 is replaced with metal complexes L005, L007, L009, L015, L018, L022, L026, L032, L055, L061, L066, L068, L076, L082, and L086, respectively, to prepare organic electroluminescent devices of corresponding metal complexes.
Comparative device example 1
An organic electroluminescent device was fabricated in accordance with the method of device example 1, except that the dopant metal complex L001 in the light-emitting layer was replaced with the compound Ir (bty)2acac，Ir(bty)2The structural formula of acac is as follows:
experimental example:
1. the organic electroluminescent devices obtained in the device examples 1 to 16 and the device comparative example 1 were subjected to a light emission characteristic test using a KEITHLEY model 2400 source measuring unit and a CS-2000 spectral radiance meter, respectively, to evaluate the driving voltage, the lifetime (T95), and the current efficiency of the devices, and the test results are shown in table 2 below.
TABLE 2
As can be seen from table 2 above, compared with the conventional organic electroluminescent device provided in device comparative example 1, the organic electroluminescent device prepared by using the metal complex provided in the embodiment of the present invention can effectively reduce the driving voltage of the organic electroluminescent device, significantly improve the current efficiency of the organic electroluminescent device, and prolong 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 (10)
1. A metal complex for a red light electroluminescent material is characterized in that the structural general formula of the metal complex is as shown in formula I:
in the formula, R1～R13Each independently is at least one of hydrogen, deuterium, nitro, amino, hydroxyl, halogen, cyano, sulfydryl, adamantane, substituted or unsubstituted alkyl of C1-C30, substituted or unsubstituted alkoxy of C1-C20, substituted or unsubstituted alkylene of C2-C10, substituted or unsubstituted alkyne of C2-C10, substituted or unsubstituted aryl of C6-C30 and substituted or unsubstituted aromatic heterocyclic group of C2-C30; and R is1～R10At least one of which is adamantane.
2. The metal complex for the red electroluminescent material as claimed in claim 1, wherein the alkyl group is selected from alkyl groups having 1 to 8 carbon atoms; the alkoxy is selected from alkoxy with 1-8 carbon atoms; the alkylene is selected from alkylene with 2-6 carbon atoms; the alkynyl is selected from alkynyl with 2-6 carbon atoms; the aryl is selected from aryl with 6-18 carbon atoms; the aromatic heterocyclic group is selected from aromatic heterocyclic groups with 3-12 carbon atoms.
3. The metal complex for a red electroluminescent material according to claim 2, wherein the alkyl group is selected from a linear alkyl group, a branched alkyl group, a cyclic alkyl group, a linear alkyl group substituted with at least one substituent, a branched alkyl group substituted with at least one substituent, or a cyclic alkyl group substituted with at least one substituent, wherein the substituents are independently selected from at least one of deuterium, nitro, amino, hydroxyl, halogen, cyano, carbonyl, and mercapto;
the aromatic heterocyclic group is independently selected from an unsubstituted aromatic heterocyclic group or an aromatic heterocyclic group having at least one substituent, wherein the substituent is independently selected from at least one of deuterium, nitro, amino, hydroxyl, halogen, cyano, carbonyl, and mercapto.
4. The metal complex for a red electroluminescent material according to claim 3, wherein the heterocyclic group of the aromatic heterocyclic groups contains at least one hetero atom selected from N, O, P, S, Si and Se.
5. The metal complex for red electroluminescent material as claimed in claim 3, wherein R is8And R10Are all methyl.
6. The metal complex for a red electroluminescent material according to claim 1, wherein the metal Ir has an auxiliary ligand on the left side and a main ligand on the right side; the primary ligand is selected from any one of the following structural formulas:
7. the metal complex for the red electroluminescent material as claimed in claim 1, wherein the chemical structural formula of the metal complex is any one of the formulas L001 to L090:
8. a process for preparing a metal complex according to any one of claims 1 to 7, comprising the steps of:
taking a compound A with a structural general formula of A and a compound C with a structural general formula of C:
under a protective atmosphere, adding the compound A and iridium trichloride into a mixed solvent of ethylene glycol ethyl ether and water for heating reaction to obtain a bridging ligand B;
and mixing the bridging ligand B with the compound C, adding ethylene glycol ethyl ether and potassium carbonate, and reacting in a protective atmosphere to obtain the metal complex.
9. A device which is 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, wherein the organic layer comprises a metal complex as claimed in any one of claims 1 to 7.
10. A device according to claim 9, wherein the organic layer comprises a light-emitting layer; the light-emitting layer comprises a host material and a doping material; the doping material partially or entirely contains the metal complex.
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