CN112010908A - Iridium complex for red light electroluminescent material, preparation method thereof and photoelectric device - Google Patents
Iridium complex for red light electroluminescent material, preparation method thereof and photoelectric device Download PDFInfo
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- CN112010908A CN112010908A CN202010894372.9A CN202010894372A CN112010908A CN 112010908 A CN112010908 A CN 112010908A CN 202010894372 A CN202010894372 A CN 202010894372A CN 112010908 A CN112010908 A CN 112010908A
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- iridium complex
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- electroluminescent material
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- 229910052741 iridium Inorganic materials 0.000 title claims abstract description 92
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 title claims abstract description 79
- 239000000463 material Substances 0.000 title claims abstract description 47
- 238000002360 preparation method Methods 0.000 title abstract description 23
- 239000003446 ligand Substances 0.000 claims abstract description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- 125000003118 aryl group Chemical group 0.000 claims abstract description 14
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 14
- -1 nitro, amino, hydroxyl Chemical group 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 11
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims abstract description 5
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 5
- 229910052805 deuterium Inorganic materials 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 150000002367 halogens Chemical class 0.000 claims abstract description 5
- 125000003342 alkenyl group Chemical group 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 41
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 239000012044 organic layer Substances 0.000 claims description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- 229940126062 Compound A Drugs 0.000 claims description 6
- 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 6
- 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 6
- 239000012298 atmosphere Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 230000001681 protective effect Effects 0.000 claims description 4
- AEDZKIACDBYJLQ-UHFFFAOYSA-N ethane-1,2-diol;hydrate Chemical compound O.OCCO AEDZKIACDBYJLQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000012046 mixed solvent Substances 0.000 claims description 3
- 230000005693 optoelectronics Effects 0.000 claims description 3
- 229910052723 transition metal Inorganic materials 0.000 claims description 3
- 150000003624 transition metals Chemical class 0.000 claims description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- 229910021638 Iridium(III) chloride Inorganic materials 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 abstract description 4
- 239000002184 metal Substances 0.000 abstract description 4
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 2
- 230000002035 prolonged effect Effects 0.000 abstract description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 37
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- 239000012299 nitrogen atmosphere Substances 0.000 description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 238000000967 suction filtration Methods 0.000 description 17
- 238000012360 testing method Methods 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 13
- 238000002347 injection Methods 0.000 description 13
- 239000007924 injection Substances 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
- 229910052760 oxygen Inorganic materials 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 238000005406 washing Methods 0.000 description 9
- 239000002346 layers by function Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 230000001376 precipitating effect Effects 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 6
- 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
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 230000005525 hole transport Effects 0.000 description 6
- 238000001819 mass spectrum Methods 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
- 238000003786 synthesis reaction Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 238000002386 leaching Methods 0.000 description 5
- 150000002503 iridium Chemical class 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 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 3
- 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
- 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
- 238000011161 development Methods 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000012827 research and development Methods 0.000 description 2
- 238000004506 ultrasonic cleaning Methods 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
- 101100490479 Lactococcus lactis subsp. lactis (strain IL1403) addA gene Proteins 0.000 description 1
- 101100000975 Lactococcus lactis subsp. lactis (strain IL1403) rexB gene Proteins 0.000 description 1
- 241000985284 Leuciscus idus Species 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-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
- 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
- 239000011248 coating agent Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 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 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
- 238000003618 dip coating Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 150000008376 fluorenones Chemical class 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 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
- 238000007641 inkjet printing Methods 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- LNJXVUXPFZKMNF-UHFFFAOYSA-K iridium(3+);trichloride;trihydrate Chemical compound O.O.O.Cl[Ir](Cl)Cl LNJXVUXPFZKMNF-UHFFFAOYSA-K 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000002156 mixing 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
- 238000005457 optimization Methods 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
- 238000001556 precipitation Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007650 screen-printing 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
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying 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
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007738 vacuum evaporation 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
- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/104—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with other heteroatoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02B—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO BUILDINGS, e.g. HOUSING, HOUSE APPLIANCES OR RELATED END-USER APPLICATIONS
- Y02B20/00—Energy efficient lighting technologies, e.g. halogen lamps or gas discharge lamps
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- 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 an iridium complex for a red light electroluminescent material, a preparation method thereof and a photoelectric device, belonging to the technical field of luminescent materials, wherein the iridium complex has a structural general formula as follows:
wherein X is C or Si; r1、R2、R3、R4、R5、R6、R7Each independently is at least one of hydrogen, deuterium, nitro, amino, hydroxyl, halogen, cyano, mercapto, alkyl, alkoxy, alkenyl, alkynyl, aryl, and aromatic heterocyclic group. The inventionThe iridium complex is prepared by combining metal iridium with a specific heterocyclic ligand, and after the iridium complex is used for photoelectric devices such as organic electroluminescent devices and the like, the driving voltage of the photoelectric devices can be reduced, the current efficiency of the photoelectric devices can be obviously improved, and the service life of the photoelectric devices can be prolonged.
Description
Technical Field
The invention relates to the technical field of luminescent materials, in particular to an iridium complex for a red light electroluminescent material, a preparation method thereof and a photoelectric device.
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 phenomenon of phosphorescence has been pursued since the discovery, and since the luminous efficiency of phosphorescence materials is obviously higher than that of fluorescence, theoretically 100%, many research and development institutions are increasing the research and development efforts of phosphor materials, and trying to accelerate the industrialization development through phosphorescence materials.
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 an iridium 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: an iridium complex for a red light electroluminescent material has a structural general formula as shown in formula I:
wherein X is C or Si;
R1、R2、R3、R4、R5、R6、R7each independently is at least one of hydrogen, deuterium, nitro, amino, hydroxyl, halogen, cyano, mercapto, alkyl, alkoxy, alkenyl, alkynyl, aryl, and aromatic heterocyclic group.
Preferably, R3The number of the substituents is 1 to 4, R4The number of the substituents is 0 to 3.
Preferably, the alkyl group is any one of C1-C8 alkyl groups;
the alkoxy is any one of C1-C8 alkoxy;
the alkylene group is any one of C2-C6 alkylene groups;
the alkynyl is any one of C2-C6 alkynyl;
the aryl is any one of C6-C18 aryl;
the aromatic heterocyclic group is any of C4 to C12 aromatic heterocyclic groups.
Preferably, the alkyl group is any one of a straight-chain alkyl group unsubstituted or substituted with at least one substituent, a branched-chain alkyl group unsubstituted or substituted with at least one substituent, and a cycloalkyl group unsubstituted or substituted with at least one substituent;
aryl is unsubstituted aryl or aryl substituted with at least one substituent;
the aromatic heterocyclic group is an unsubstituted aromatic heterocyclic group or an aromatic heterocyclic group substituted with at least one substituent;
the substituent is independently selected from one or more of deuterium, nitro, amino, hydroxyl, halogen, cyano, carbonyl and sulfydryl.
Preferably, R1、R2Each independently is methyl.
Preferably, in the formula I, the left side of the transition metal Ir is an auxiliary ligand, and the right side of the transition metal Ir is a main ligand; wherein, the main ligand is selected from any one of the following structural formulas:
preferably, the iridium complex has a chemical structural formula of any one of formula L001 to formula L105, but is not limited thereto:
another object of the embodiments of the present invention is to provide a preparation method of the iridium 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 the protective atmosphere, placing the compound A and iridium trichloride in a mixed solvent of ethylene glycol ethyl ether and water for reaction to obtain a bridging ligand B with a structural general formula of formula B:
and reacting the bridging ligand B, the compound C, ethylene glycol ethyl ether and potassium carbonate under a protective atmosphere to obtain the iridium complex.
The synthetic route of the preparation method is as follows:
preferably, the preparation method of the iridium complex specifically comprises the following steps:
(1) under the protection of nitrogen, compound A is mixed with iridium trichloride trihydrate (IrCl)3·3H2O) is mixed according to the molar ratio of 3:1 and then is added into the mixed solvent of ethylene glycol ethyl ether and water for heating reaction, and a bridging ligand B is prepared after full reaction;
(2) and mixing the bridging ligand B with the compound C, adding ethylene glycol ethyl ether and potassium carbonate, and stirring for 24 hours at 120 ℃ under the protection of nitrogen to perform full reaction to obtain the iridium complex.
Another object of an embodiment of the present invention is to provide an application of the iridium complex in preparation of an organic electroluminescent device.
It is another object of an embodiment of the present invention to provide an optoelectronic 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 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 comprises the iridium complex.
Preferably, the mass ratio of the host material to the doping material is (90-99.5): (0.5-10).
Specifically, the first electrode is an anode, the type of which is not particularly limited, and may be a conventional anode known to those skilled in the art, and more preferably 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 kind of which is not particularly limited, and is 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, and the thickness of the second electrode is 100 to 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.
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, a conductive polymer, an N-type semiconductive organic complex and a metal organic complex, 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 Li2O、Al2O3And MgO with a thickness of 0.1-10 nm.
In the embodiment of the present invention, the above light emitting layer and other various functional layers may be formed by a solution coating method and a vacuum deposition method. The solution coating method means spin coating, dip coating, inkjet printing, screen printing, spraying method, etc., but is not limited thereto.
The above-mentioned photoelectric device may be an organic electroluminescent device, an organic solar cell, electronic paper, an organic photoreceptor, an organic thin film transistor, or the like, but is not limited thereto.
Compared with the prior art, the embodiment of the invention has the beneficial effects that:
the iridium complex for the red light electroluminescent material is prepared by combining metal iridium with a specific heterocyclic ligand, and after the iridium complex is used for photoelectric devices such as organic electroluminescent devices and the like, the driving voltage of the photoelectric devices can be reduced, the current efficiency of the photoelectric devices can be obviously improved, and the service life of the photoelectric devices can be prolonged. In addition, the preparation method of the iridium complex provided by the embodiment of the invention has the characteristics of simple synthesis steps, mild condition requirements and high yield of target products, and solves the problems of high synthesis price and high synthesis process requirements of the existing phosphor luminescent material.
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.
Complex example 1
The embodiment of the complex provides an iridium complex for a red light electroluminescent material, the chemical structural formula of the iridium complex is formula L001 in the invention content, and the reaction route of the preparation method of the iridium complex is as follows:
the specific preparation method comprises the following steps:
1) using a nitrogen-purged reactor, compound A-001(85.2mmol, 27.38g) and IrCl were charged into the reactor under a nitrogen atmosphere3·3H2Refluxing O (28.4mmo1, 10g), 600mL of ethylene glycol ethyl ether and 200mL of purified water for 24 hours in a nitrogen atmosphere, cooling to room temperature, separating out a precipitate, performing 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 a red powdery bridging ligand B-001(15.53g, the yield is 63%);
2) adopting a nitrogen replacement reactor, adding a bridging ligand B-001(8mmol, 13.89g) and a compound C-001(24mmol, 2.37g) into the reactor under the nitrogen atmosphere, adding 270mL of ethylene glycol ethyl ether and potassium carbonate (11.04g) into the system, stirring for 24 hours at 120 ℃ under the nitrogen atmosphere, carrying out suction filtration, washing with alcohol, drying, using dichloromethane as an eluent, carrying out silica gel column chromatography, concentrating the filtrate, precipitating a solid, and carrying out suction filtration to finally obtain a red iridium complex L001(8.5g, the yield is 57%).
The iridium complex is detected and analyzed, and the specific result is as follows:
HPLC purity: greater than 99%.
Mass spectrum: calculated value 932.16; the test value was 933.27.
Elemental analysis:
the calculated values are: 68.29 percent of C; 4.65 percent of H; 3.01 percent of N; 3.43 percent of O; 20.62 percent of Ir;
the test values are: 68.28 percent of C; 4.64 percent of H; 3.02 percent of N; 3.42 percent of O; 20.63 percent of Ir.
By comparing the calculated value with the tested value, the measured value is basically consistent with the theoretical value, thereby proving that the iridium complex with the structural formula of L001 can be successfully synthesized by the complex example.
Complex example 2
The embodiment of the complex provides an iridium complex for a red light electroluminescent material, the chemical structural formula of the iridium complex is a formula L015 in the invention content, and the reaction route of the preparation method of the iridium complex is as follows:
the specific preparation method comprises the following steps:
1) the reactor was purged with nitrogen, and Compound A-015(85.2mmol, 33.86g), IrCl were added to the reactor under a nitrogen atmosphere3·3H2Refluxing O (28.4mmo1, 10g), 600mL of ethylene glycol ethyl ether and 200mL of purified water for 24 hours in a nitrogen atmosphere, cooling to room temperature, separating out a precipitate, performing 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 a red powdery bridging ligand B-015(19.13g, the yield is 66%);
2) adopting a nitrogen replacement reactor, adding a bridging ligand B-015(8mmol, 16.33g) and a compound C-015(24mmol, 2.37g) into the reactor in a nitrogen atmosphere, adding ethylene glycol ethyl ether 270m L and potassium carbonate (11.04g) into the system, stirring for 24 hours at 120 ℃ in the nitrogen atmosphere, carrying out suction filtration, washing with alcohol, drying, using dichloromethane as an eluent, carrying out silica gel column chromatography, concentrating the filtrate, precipitating a solid, and carrying out suction filtration to finally obtain a red iridium complex L015(10.06g, 58% of yield).
The iridium complex is detected and analyzed, and the specific result is as follows:
HPLC purity: greater than 99%.
Mass spectrum: calculated value 1084.35; the test value was 1084.35.
Elemental analysis:
the calculated values are: 72.00 percent of C; 4.47 percent of H; 2.58 percent of N; 2.95 percent of O; 17.73 percent of Ir;
the test values are: 72.01 percent of C; 4.46 percent of H; 2.59 percent of N; 2.94 percent of O; 17.74 percent of Ir.
As can be seen by comparing the calculated values with the test values, the measured values are substantially consistent with the theoretical values, thereby proving that the iridium complex with the structural formula of L015 can be successfully synthesized by the complex example.
Complex example 3
The embodiment of the complex provides an iridium complex for a red light electroluminescent material, the chemical structural formula of the iridium complex is formula L022 in the invention content, and the reaction route of the preparation method of the iridium complex is as follows:
the specific preparation method comprises the following steps:
1) the reactor was purged with nitrogen, and Compound A-022(85.2mmol, 32.50g) and IrCl were added to the reactor under a nitrogen atmosphere3·3H2Refluxing O (28.4mmo1, 10g), 600mL of ethylene glycol ethyl ether and 200mL of purified water for 24 hours in a nitrogen atmosphere, cooling to room temperature, precipitating, performing 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 a red powdery bridging ligand B-022(15.96g, the yield is 58%);
2) adopting a nitrogen replacement reactor, adding a bridging ligand B-022(8mmol, 15.50g) and a compound C-022(24mmol, 3.72g) into the reactor under a nitrogen atmosphere, adding 270mL of ethylene glycol ethyl ether and potassium carbonate (11.04g) into the system, stirring for 24 hours at 120 ℃ under the nitrogen atmosphere, carrying out suction filtration, washing with alcohol, drying, using dichloromethane as an eluent, carrying out silica gel column chromatography, carrying out solid precipitation after filtrate concentration, and carrying out suction filtration to finally obtain a red iridium complex L022(8.53g, yield 49%).
The iridium complex is detected and analyzed, and the specific result is as follows:
HPLC purity: greater than 99%.
Mass spectrum: calculated value 1088.38; the test value was 1089.32.
Elemental analysis:
the calculated values are: 71.73 percent of C; 5.09 percent of H; 2.57 percent of N; 2.94 percent of O; 17.66 percent of Ir;
the test values are: 71.74 percent of C; 5.10 percent of H; 2.56 percent of N; 2.93 percent of O; 17.65 percent of Ir.
By comparing the calculated value with the tested value, the measured value is basically consistent with the theoretical value, thereby proving that the iridium complex with the structural formula of L022 can be successfully synthesized by the complex example.
Complex example 4
The embodiment of the complex provides an iridium complex for a red light electroluminescent material, the chemical structural formula of the iridium complex is shown as a formula L026 in the summary of the invention, and the reaction route of the preparation method of the iridium complex is as follows:
the specific preparation method comprises the following steps:
1) by replacing the reactor with nitrogen, compound A-026(85.2mmol, 40.35g), IrCl were added to the reactor under a nitrogen atmosphere3·3H2Refluxing O (28.4mmo1, 10g), 600mL of ethylene glycol ethyl ether and 200mL of purified water for 24 hours in a nitrogen atmosphere, cooling to room temperature, separating out a precipitate, performing 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 a red powdery bridging ligand B-026(21.31g, the yield is 64%);
2) adopting a nitrogen displacement reactor, adding a bridging ligand B-026(8mmol, 18.76g) and a compound C-026(24mmol, 3.72g) into the reactor under the nitrogen atmosphere, adding ethylene glycol ethyl ether 270mL and potassium carbonate (11.04g) into the system, stirring for 24 hours at 120 ℃ under the nitrogen atmosphere, carrying out suction filtration, washing with alcohol, drying, using dichloromethane as an eluent, carrying out silica gel column chromatography, concentrating the filtrate, precipitating a solid, and carrying out suction filtration to finally obtain a red iridium complex L026(11.78g, yield 57%).
The iridium complex is detected and analyzed, and the specific result is as follows:
HPLC purity: greater than 99%.
Mass spectrum: calculated value 1292.66; the test value was 1293.27.
Elemental analysis:
the calculated values are: 75.26 percent of C; 5.22 percent of H; 2.17 percent of N; 2.48 percent of O; 14.87 percent of Ir;
the test values are: 75.27 percent of C; 5.21 percent of H; 2.18 percent of N; 2.47 percent of O; 14.88 percent of Ir.
By comparing the calculated value with the tested value, the measured value is basically consistent with the theoretical value, thereby proving that the iridium complex with the structural formula of L026 can be successfully synthesized by the complex example.
Complex example 5
The embodiment of the complex provides an iridium complex for a red light electroluminescent material, the chemical structural formula of the iridium complex is shown as formula L069 in the invention content, and the reaction route of the preparation method of the iridium complex is as follows:
the specific preparation method comprises the following steps:
1) the reactor was purged with nitrogen and, under a nitrogen atmosphere, Compound A-063(85.2mmol, 31.65g), IrCl were charged into the reactor3·3H2O (28.4mmo1, 10g), 600mL of ethylene glycol ethyl ether and 200mL of purified water are refluxed for 24 hours in nitrogen atmosphere, then cooled to room temperature, precipitated, filtered to obtain solid, leached by using 50mL of water, 50mL of absolute ethyl alcohol and 50mL of petroleum ether in sequence, and dried to obtain red powderThe powdered bridged ligand B-069(17.33g, 63% yield);
2) adopting a nitrogen replacement reactor, adding a bridging ligand B-069(8mmol, 15.49g) and a compound C-069(24mmol, 4.06g) into the reactor under the nitrogen atmosphere, adding ethylene glycol ethyl ether 270m L and potassium carbonate (11.04g) into the system, stirring for 24 hours at 120 ℃ under the nitrogen atmosphere, carrying out suction filtration, washing with alcohol, drying, using dichloromethane as an eluent, carrying out silica gel column chromatography, concentrating the filtrate, precipitating a solid, and carrying out suction filtration to finally obtain a red iridium complex L069(11.81g, the yield is 67%).
The iridium complex is detected and analyzed, and the specific result is as follows:
HPLC purity: greater than 99%.
Mass spectrum: calculated value 1102.41; the test value was 1103.25.
Elemental analysis:
the calculated values are: c, 71.91 percent; 5.21 percent of H; 2.54 percent of N; 2.90 percent of O; 17.44 percent of Ir;
the test values are: 71.92 percent of C; 5.20 percent of H; 2.55 percent of N; 2.91 percent of O; 17.43 percent of Ir.
By comparing the calculated value with the tested value, the measured value is basically consistent with the theoretical value, thereby proving that the iridium complex with the structural formula of L069 can be successfully synthesized by the complex example.
Complex example 6
The embodiment of the complex provides an iridium complex for a red light electroluminescent material, the chemical structural formula of the iridium complex is formula L092 in the invention content, and the reaction route of the preparation method of the iridium complex is as follows:
the specific preparation method comprises the following steps:
1) the reactor was purged with nitrogen, and Compound A-092(85.2mmol, 27.38g) and IrCl were charged into the reactor under a nitrogen atmosphere3·3H2O (28.4mmo1, 10g), 600mL of ethylene glycol ethyl ether, 200mL of purified water, and nitrogen gasRefluxing for 24 hours under the atmosphere, then cooling to room temperature, precipitating, performing suction filtration to obtain a solid, leaching with 50mL of water, 50mL of absolute ethanol and 50mL of petroleum ether in sequence, and drying to obtain a red powdery bridging ligand B-092(15.29g, yield 62%);
2) adopting a nitrogen replacement reactor, adding a bridging ligand B-092(8mmol, 13.89) and a compound C-092(24mmol, 5.55g) into the reactor under a nitrogen atmosphere, adding ethylene glycol ethyl ether 270m L and potassium carbonate (11.04g) into the system, stirring for 24 hours at 120 ℃ under the nitrogen atmosphere, carrying out suction filtration, washing with alcohol, drying, using dichloromethane as an eluent, carrying out silica gel column chromatography, concentrating the filtrate, precipitating a solid, and carrying out suction filtration to finally obtain a red iridium complex L092(8.68g, 51% yield).
The iridium complex is detected and analyzed, and the specific result is as follows:
HPLC purity: greater than 99%.
Mass spectrum: calculated value 1064.36; the test value was 1065.12.
Elemental analysis:
the calculated values are: 71.09 percent of C; 5.21 percent of H; 2.63 percent of N; 3.01 percent of O; 18.06 percent of Ir;
the test values are: 71.08 percent of C; 5.20 percent of H; 2.62 percent of N; 3.02 percent of O; 18.07 percent of Ir.
By comparing the calculated value with the test value, the measured value is basically consistent with the theoretical value, thereby proving that the iridium complex with the structural formula of L092 can be successfully synthesized by the complex example.
Examples 7 to 16 of the complexes
Because the synthetic route and the principle of the preparation method of other iridium complexes with the structural general formula of formula I in the invention content are the same as those of the complex example 1 listed above, the compound A and the compound C only need to be replaced by compounds corresponding to corresponding ligand structures in the target product respectively, and the corresponding iridium complexes can be obtained by correspondingly adjusting the material dosage according to the corresponding stoichiometric ratio, so that the process is not exhaustive, and a plurality of iridium complexes are selected as the complex examples 7-16 in the invention, and are specifically shown in the following table 1.
TABLE 1
The embodiment of the invention also provides a photoelectric device prepared by using the iridium complex provided by the embodiment, and particularly, the photoelectric 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 layer selected from a hole injection layer, a hole transport layer, a composite layer of hole injection and hole transport technical layers, an electron blocking layer, an emission 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 layer may or may not include the iridium complex.
Specifically, the light-emitting layer includes a host material and a dopant material; wherein, the host material can be 4, 4'-N, N' -biphenyl dicarbazole ("CBP"), but is not limited thereto; the doping material can be the iridium complex.
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:
(1) coating with a thickness of
The ITO glass substrate is put in distilled water for cleaning for 2 times, ultrasonic cleaning is carried out for 30 minutes, the ITO glass substrate is repeatedly cleaned for 2 times by distilled water and ultrasonic cleaning is carried out for 10 minutes, and after the cleaning by distilled water is finished, isopropanol, acetone and methanol solvent are sequentially carried outUltrasonic washing (each time, 10min for each washing), drying, transferring into a plasma cleaning machine, washing the substrate for 5 min, and transferring into an evaporation machine;
(2) using ITO as anode, firstly, evaporating CuPc on it
Then sequentially evaporating NPB
A mixture of the host substance 4, 4'-N, N' -biphenyldicarbazole ("CBP") and the iridium complex L001 described above ((II))
Wherein the weight ratio of 4, 4'-N, N' -biphenyl dicarbazole to iridium complex L001 is 95:5), and an electron transport layer Alq3"
Electron injection layer LiF
Cathode Al
And the organic electroluminescent device can be prepared.
Device examples 2 to 16
An organic electroluminescent device was fabricated by referring to the fabrication method provided in device example 1 above, except that the iridium complex L001 (doping material) in device example 1 above was replaced with the iridium complexes L006, L008, L015, L017, L022, L025, L026, L032, L045, L069, L072, L081, L092, L098, and L103 above, respectively, to fabricate a corresponding organic electroluminescent device.
Comparative device example 1
An organic electroluminescent device was fabricated by referring to the fabrication method provided in device example 1 above, except thatReplacement of Iridium Complex L001 (dopant) in device example 1 described above with existing Iridium Metal Complex Ir (bty)2acac, wherein, Ir (bty)2The structural formula of acac is as follows:
experimental example:
the performance and the light emitting characteristics of the organic electroluminescent devices obtained in the device examples 1 to 16 and the device comparative example 1 were respectively tested under the same luminance conditions by using a KEITHLEY model 2400 source measuring unit and a CS-2000 spectroradiometer to evaluate the driving voltage, the current efficiency and the light emitting life of the organic electroluminescent device (T95), and the specific test results are shown in table 2.
TABLE 2
As can be seen from Table 2 above, comparison is made with the device provided in comparative example 1 at I r (bty)2The organic electroluminescent device prepared by adopting the iridium complex provided by the embodiment of the invention as the doping material can effectively reduce the driving voltage of a photoelectric device, and can remarkably improve the current efficiency and 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. An iridium complex for a red light electroluminescent material is characterized in that the structural general formula of the iridium complex is as shown in formula I:
wherein X is C or Si;
R1、R2、R3、R4、R5、R6、R7each independently is at least one of hydrogen, deuterium, nitro, amino, hydroxyl, halogen, cyano, mercapto, alkyl, alkoxy, alkenyl, alkynyl, aryl, and aromatic heterocyclic group.
2. The iridium complex for red electroluminescent material as claimed in claim 1, wherein R is3The number of the substituents is 1 to 4, R4The number of the substituents is 0 to 3.
3. The iridium complex for a red electroluminescent material according to claim 1, wherein the alkyl group is any one of C1 to C8 alkyl groups;
the alkoxy is any one of C1-C8 alkoxy;
the alkylene group is any one of C2-C6 alkylene groups;
the alkynyl is any one of C2-C6 alkynyl;
the aryl is any one of C6-C18 aryl;
the aromatic heterocyclic group is any of C4 to C12 aromatic heterocyclic groups.
4. The iridium complex for a red electroluminescent material according to claim 1, wherein the alkyl group is any one of a straight-chain alkyl group unsubstituted or substituted with at least one substituent, a branched-chain alkyl group unsubstituted or substituted with at least one substituent, and a cycloalkyl group unsubstituted or substituted with at least one substituent;
aryl is unsubstituted aryl or aryl substituted with at least one substituent;
the aromatic heterocyclic group is an unsubstituted aromatic heterocyclic group or an aromatic heterocyclic group substituted with at least one substituent;
the substituent is independently selected from one or more of deuterium, nitro, amino, hydroxyl, halogen, cyano, carbonyl and sulfydryl.
5. The iridium complex for red electroluminescent material as claimed in claim 1, wherein R is1、R2Each independently is methyl.
6. The iridium complex for a red electroluminescent material as claimed in claim 1, wherein in formula I, the left side of the transition metal Ir is an auxiliary ligand, and the right side is a main ligand; wherein, the main ligand is selected from any one of the following structural formulas:
7. the iridium complex for the red electroluminescent material as claimed in claim 1, wherein the iridium complex has a chemical structural formula of any one of formula L001 to formula L105:
8. a method for producing an iridium 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 the protective atmosphere, placing the compound A and iridium trichloride in a mixed solvent of ethylene glycol ethyl ether and water for reaction to obtain a bridging ligand B with a structural general formula of formula B:
and reacting the bridging ligand B, the compound C, ethylene glycol ethyl ether and potassium carbonate under a protective atmosphere to obtain the iridium complex.
9. An optoelectronic 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 an iridium complex according to any one of claims 1 to 7.
10. The optoelectronic 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 comprises the iridium complex.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112552353A (en) * | 2020-12-27 | 2021-03-26 | 浙江华显光电科技有限公司 | Iridium metal complex and organic photoelectric element using same |
| CN113402563A (en) * | 2021-06-16 | 2021-09-17 | 吉林奥来德光电材料股份有限公司 | Iridium complex, preparation method thereof, organic electroluminescent device and display device |
| CN114075252A (en) * | 2021-08-25 | 2022-02-22 | 吉林奥来德光电材料股份有限公司 | Iridium metal compound, light-emitting material, light-emitting layer, and organic electroluminescent device |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110016058A (en) * | 2019-04-24 | 2019-07-16 | 北京诚志永华显示科技有限公司 | Metal complex, electroluminescent organic material, organic electroluminescence device |
| CN110294778A (en) * | 2018-03-23 | 2019-10-01 | 机光科技股份有限公司 | Iridium compound and the organic electroluminescent element for using it |
| CN110804073A (en) * | 2019-11-08 | 2020-02-18 | 吉林奥来德光电材料股份有限公司 | Iridium metal complex and iridium metal complex organic electroluminescent device |
| CN111116668A (en) * | 2019-12-24 | 2020-05-08 | 吉林奥来德光电材料股份有限公司 | Organic iridium metal complex and preparation method and application thereof |
| CN111253442A (en) * | 2020-03-17 | 2020-06-09 | 吉林奥来德光电材料股份有限公司 | Organic iridium metal complex, preparation method thereof and organic electroluminescent device |
| CN111278843A (en) * | 2017-11-08 | 2020-06-12 | 罗门哈斯电子材料韩国有限公司 | Organic electroluminescent compounds and organic electroluminescent device comprising the same |
| CN111303213A (en) * | 2020-04-15 | 2020-06-19 | 吉林奥来德光电材料股份有限公司 | Phosphorescent iridium complex, preparation method thereof and organic electroluminescent device |
-
2020
- 2020-08-31 CN CN202010894372.9A patent/CN112010908B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111278843A (en) * | 2017-11-08 | 2020-06-12 | 罗门哈斯电子材料韩国有限公司 | Organic electroluminescent compounds and organic electroluminescent device comprising the same |
| CN110294778A (en) * | 2018-03-23 | 2019-10-01 | 机光科技股份有限公司 | Iridium compound and the organic electroluminescent element for using it |
| CN110016058A (en) * | 2019-04-24 | 2019-07-16 | 北京诚志永华显示科技有限公司 | Metal complex, electroluminescent organic material, organic electroluminescence device |
| CN110804073A (en) * | 2019-11-08 | 2020-02-18 | 吉林奥来德光电材料股份有限公司 | Iridium metal complex and iridium metal complex organic electroluminescent device |
| CN111116668A (en) * | 2019-12-24 | 2020-05-08 | 吉林奥来德光电材料股份有限公司 | Organic iridium metal complex and preparation method and application thereof |
| CN111253442A (en) * | 2020-03-17 | 2020-06-09 | 吉林奥来德光电材料股份有限公司 | Organic iridium metal complex, preparation method thereof and organic electroluminescent device |
| CN111303213A (en) * | 2020-04-15 | 2020-06-19 | 吉林奥来德光电材料股份有限公司 | Phosphorescent iridium complex, preparation method thereof and organic electroluminescent device |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112552353A (en) * | 2020-12-27 | 2021-03-26 | 浙江华显光电科技有限公司 | Iridium metal complex and organic photoelectric element using same |
| CN113402563A (en) * | 2021-06-16 | 2021-09-17 | 吉林奥来德光电材料股份有限公司 | Iridium complex, preparation method thereof, organic electroluminescent device and display device |
| CN114075252A (en) * | 2021-08-25 | 2022-02-22 | 吉林奥来德光电材料股份有限公司 | Iridium metal compound, light-emitting material, light-emitting layer, and organic electroluminescent device |
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