CN111848687B - Red light organic electroluminescent material, preparation method thereof and photoelectric device - Google Patents
Red light organic electroluminescent material, preparation method thereof and photoelectric device Download PDFInfo
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- CN111848687B CN111848687B CN202010684213.6A CN202010684213A CN111848687B CN 111848687 B CN111848687 B CN 111848687B CN 202010684213 A CN202010684213 A CN 202010684213A CN 111848687 B CN111848687 B CN 111848687B
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- 239000000463 material Substances 0.000 title claims abstract description 107
- 238000002360 preparation method Methods 0.000 title abstract description 20
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims abstract description 8
- 229910052805 deuterium Inorganic materials 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 150000002367 halogens Chemical class 0.000 claims abstract description 8
- 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
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 239000003446 ligand Substances 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 16
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 239000012044 organic layer Substances 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 239000012298 atmosphere Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 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
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 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
- 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
- 239000012046 mixed solvent Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- -1 nitro, amino, hydroxyl Chemical group 0.000 abstract description 15
- 125000006615 aromatic heterocyclic group Chemical group 0.000 abstract description 9
- 125000003118 aryl group Chemical group 0.000 abstract description 8
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 abstract description 2
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 abstract description 2
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 abstract description 2
- 125000005865 C2-C10alkynyl group Chemical group 0.000 abstract 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
- 239000007787 solid Substances 0.000 description 19
- 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 238000002347 injection Methods 0.000 description 12
- 239000007924 injection Substances 0.000 description 12
- 239000002346 layers by function Substances 0.000 description 8
- 238000001556 precipitation Methods 0.000 description 8
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- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
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- 101100490051 Lactococcus lactis subsp. lactis (strain IL1403) accD gene Proteins 0.000 description 5
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- 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
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
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- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical group 0.000 description 2
- 125000002355 alkine group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
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- 239000000243 solution Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- MWTPXLULLUBAOP-UHFFFAOYSA-N 2-phenoxy-1,3-benzothiazole Chemical class N=1C2=CC=CC=C2SC=1OC1=CC=CC=C1 MWTPXLULLUBAOP-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- 101100027846 Lactococcus lactis subsp. lactis (strain IL1403) obg gene Proteins 0.000 description 1
- 101100000975 Lactococcus lactis subsp. lactis (strain IL1403) rexB gene Proteins 0.000 description 1
- 229920001090 Polyaminopropyl biguanide Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000008425 anthrones Chemical class 0.000 description 1
- 150000007980 azole derivatives Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 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
- 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
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 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
- VBVAVBCYMYWNOU-UHFFFAOYSA-N coumarin 6 Chemical class C1=CC=C2SC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 VBVAVBCYMYWNOU-UHFFFAOYSA-N 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 150000008376 fluorenones Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 230000006872 improvement Effects 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
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000004519 manufacturing process Methods 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
- 230000005693 optoelectronics Effects 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002904 solvent 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
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical class [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
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- 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
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- 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
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- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- 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
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- 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)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
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- Physics & Mathematics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Optics & Photonics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention discloses a red light organic electroluminescent material, a preparation method thereof and a photoelectric device, belonging to the technical field of luminescent materials, wherein the structural general formula of the red light organic electroluminescent material is as follows:
wherein R is 1 ～R 9 Each independently is at least one of hydrogen, deuterium, nitro, amino, hydroxyl, halogen, cyano, mercapto, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 aromatic heterocyclic. The device containing the red light organic electroluminescent material 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 red light organic electroluminescent material, a preparation method thereof and a photoelectric device.
Background
In 1987, deng Qingyun doctor reported that electroluminescent diode technology based on organic luminescent material mainly adopts vacuum evaporation to prepare a double-layer device with a transmission layer and a luminescent layer, the quantum efficiency is improved to 1%, and the quantum efficiency can reach 1000cd/m under the working voltage lower than 10V 2 The brightness of the organic electroluminescent device is widely paid attention to by world science lovers, and the organic electroluminescent technology is pushed to the step of practical application. Electroluminescent device having all-solid structureOrganic electroluminescent materials are the core and the basis of the device. The development of new materials is a source of driving the continuous progress of electroluminescent technology. The preparation of the original materials and the optimization of devices are also research hot spots of the current organic electroluminescent industry.
Since the phosphorescence has been found, since the current efficiency of the phosphorescence is significantly higher than that of fluorescence, the current efficiency of the phosphorescence can reach 100% theoretically, so many scientific research institutions are increasing the research and development efforts of the phosphorescence, and attempt to accelerate the industrialization development through the phosphorescence. However, the phosphorescent materials have high synthesis price, high synthesis process requirements, easy environmental pollution in the synthesis process, high purification requirements and low efficiency. Accordingly, the prior art is still in need of improvement and development.
Disclosure of Invention
An objective of the embodiments of the present invention is to provide a red organic electroluminescent material, so as to solve the problems set forth in the background art.
In order to achieve the above object, the embodiment of the present invention provides the following technical solutions:
a red light organic electroluminescent material has a structural formula as shown in formula I:
wherein R is 1 ～R 9 Each independently is at least one of hydrogen, deuterium, nitro, amino, hydroxyl, halogen, cyano, mercapto, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 aromatic heterocyclic.
Preferably, 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 olefin group is selected from olefin groups with 2-6 carbon atoms; the alkyne group is selected from alkyne groups 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 having 4 to 12 carbon atoms.
Preferably, the alkyl group is selected from the group consisting of linear alkyl, branched alkyl, cycloalkyl, linear alkyl substituted with at least one substituent, branched alkyl substituted with at least one substituent, and cycloalkyl substituted with at least one substituent, wherein the substituents are independently selected from at least one of deuterium, nitro, amino, hydroxy, halogen, cyano, carbonyl, and mercapto.
Preferably, the aryl is selected from unsubstituted aryl or aryl containing at least one substituent, wherein the substituent is independently selected from at least one of deuterium, nitro, amino, hydroxy, halogen, cyano, carbonyl and mercapto;
the aromatic heterocyclic groups are independently selected from unsubstituted aromatic heterocyclic groups or aromatic heterocyclic groups containing at least one substituent, wherein the substituent is independently selected from at least one of deuterium, nitro, amino, hydroxy, halogen, cyano, carbonyl and mercapto.
Preferably, the heterocyclic group in the aromatic heterocyclic group comprises at least one heteroatom of N, O, P, S, si and Se.
Preferably, the heterocyclic group in the aromatic heterocyclic group comprises at least one heteroatom of N, O and S.
Preferably, in the formula, the left side of the metal Ir is an auxiliary ligand, and the right side is a main ligand; the primary ligand is selected from any one of the following structural formulas:
preferably, the chemical structural formula of the red light organic electroluminescent material is any one of formulas L001 to L090:
another object of the embodiment of the present invention is to provide a method for preparing the above red organic electroluminescent material, which includes the following steps:
taking a compound A with a structural formula of formula A and a compound C with a structural formula of formula C:
under the protective atmosphere, adding the compound A and iridium trichloride into a mixed solvent of ethylene glycol diethyl ether and water for heating reaction to obtain a bridging ligand B;
and mixing the bridging ligand B with the compound C, adding glycol diethyl ether and potassium carbonate, and placing the mixture in a protective atmosphere for reaction to obtain the red light organic electroluminescent material.
Specifically, the synthetic route of the above steps is as follows:
wherein, the liquid crystal display device comprises a liquid crystal display device,R 1 ～R 9 the same definition as in formula I above.
Another object of the embodiments of the present invention is to provide an optoelectronic device, which may be an organic electroluminescent device, including a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, where the organic layer includes the above-mentioned red organic electroluminescent material.
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 completely contains the red light organic electroluminescent material.
Specifically, the first electrode is an anode, and the type thereof is not particularly limited, and may be a conventional anode well known to those skilled in the art, and 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 well known to those skilled in the art, and more preferably one of Al, li, na, K, mg, ca, au, ag, pb.
The host material is preferably one or more of 4,4'-N, N' -biphenyl dicarbazole (CBP), octahydroxyquinoline (Alq 3), metal phenoxy benzothiazole compounds, polyfluorene, aromatic condensed rings and zinc complex. The mass ratio of the doping material in the light-emitting layer is preferably 0.5% -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 types of the respective functional layers are not particularly limited, and may be conventional functional layers well known to those skilled in the art. Preferably: the hole injection layer is 2-TNATA (i.e., N1- (2-naphthyl) -N4, N4-bis (4- (2-naphthyl (phenyl) amino))Phenyl) -N1-phenyl benzene-1, 4-diamine), phthalocyanines and porphyrin compounds, star burst triarylamines, conductive polymers, N-type semiconductive organic complexes, metal organic complexes; 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 (phenanthren-9-yl) -N, N' -diphenyl benzidine) arylamine carbazole compound and indolocarbazole compound; the hole blocking layer is one of BAlq, BCP, BPhen; the electron transport layer is one of Alq3, coumarin 6, triazole derivative, azole derivative, oxadiazole derivative, imidazole derivative, fluorenone derivative and anthrone derivative; the electron injection layer is LiF, csF, li 2 O、A1 2 O 3 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 red light organic electroluminescent material provided by the embodiment of the invention, through the combination of the transition metal iridium and the specific heterocyclic ligand, the relative molecular mass of the material is increased, 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 of the embodiments of the present invention will be clearly and completely described below in conjunction with the embodiments of the present invention, and it is apparent that the described embodiments are only some embodiments of the present invention, not all embodiments.
Material example 1
The embodiment of the material provides a red light organic electroluminescent material, the chemical structural formula of which is the formula L001 in the summary of the invention, and the reaction route of the preparation method of the red light organic electroluminescent material is as follows:
the preparation method specifically comprises the following steps:
s1, replacing the reactor with nitrogen, and adding a compound A-001 (85.2 mmol,23.29 g) and IrCl into the reactor under the nitrogen atmosphere 3 ·3H 2 O (28.4 mmol,10 g), 600mL of ethylene glycol diethyl ether and 200mL of purified water are placed under nitrogen atmosphere and refluxed for 24 hours for heating reaction, then cooled to room temperature, precipitation is carried out, solid is obtained by suction filtration, and the solid is sequentially rinsed with 50mL of water, 50mL of absolute ethanol and 50mL of petroleum ether, and dried, thus obtaining red powdery bridged ligand B-001 (14.03 g, yield is 64%).
S2, adopting nitrogen to replace a reactor, adding the bridging ligand B-001 (8 mmol,12.35 g) and the compound C-001 (24 mmol,2.37 g) into the reactor under the nitrogen atmosphere, adding 270mL of ethylene glycol diethyl ether and potassium carbonate (11.04 g) into the system, placing the mixture in the nitrogen atmosphere, stirring the mixture at 120 ℃ for 24 hours for reaction, carrying out suction filtration, washing with alcohol, drying, using dichloromethane as an eluent, carrying out silica gel column chromatography, concentrating the filtrate, and then carrying out solid precipitation, and carrying out suction filtration to finally obtain the red-light organic electroluminescent material L001 (6.95 g, yield 52%).
The red light organic electroluminescent material L001 is detected and analyzed, and the specific results are as follows:
mass spectrometry: calculated 836.07; the test value was 837.24.
Elemental analysis:
the calculated values are: c:64.65%; h:5.18%; n:3.35%; o:3.83%; ir:22.29%;
the test values are: c:64.66%; h:5.17%; n:3.36%; o:3.82%; ir:22.30%.
By comparing the calculated value with the test value, the measured value is basically consistent with the theoretical value, thus proving that the red organic electroluminescent material with the structural formula L001 can be successfully synthesized by the material embodiment.
Material example 2
The embodiment of the material provides a red light organic electroluminescent material, the chemical structural formula of which is the formula L009 in the summary of the invention, and the reaction route of the preparation method of the red light organic electroluminescent material is as follows:
the preparation method specifically comprises the following steps:
s1, replacing the reactor with nitrogen, and adding the compound A-009 (85.2 mmol,25.16 g) and IrCl into the reactor under the nitrogen atmosphere 3 ·3H 2 O (28.4 mmol,10 g), 600mL of ethylene glycol diethyl ether and 200mL of purified water are placed under nitrogen atmosphere and refluxed for 24 hours for heating reaction, then cooled to room temperature, precipitation is carried out, solid is obtained by suction filtration, and the solid is sequentially rinsed with 50mL of water, 50mL of absolute ethanol and 50mL of petroleum ether, and dried, thus obtaining red powdery bridged ligand B-009 (14.37 g, yield 62%).
S2, adopting nitrogen to replace a reactor, adding the bridging ligand B-009 (8 mmol,13.06 g) and the compound C-009 (24 mmol,2.37 g) into the reactor under the nitrogen atmosphere, adding 270mL of ethylene glycol diethyl ether and potassium carbonate (11.04 g) into the system, placing the mixture in the nitrogen atmosphere, stirring the mixture at 120 ℃ for 24 hours for reaction, carrying out suction filtration, washing with alcohol, drying, using dichloromethane as an eluent, carrying out silica gel column chromatography, concentrating the filtrate, and then carrying out solid precipitation, and carrying out suction filtration to finally obtain the red-light organic electroluminescent material L009 (7.18 g, and 51% yield).
The red light organic electroluminescent material L009 is detected and analyzed, and the specific results are as follows:
mass spectrometry: calculated 880.00; the test value was 881.31.
Elemental analysis:
the calculated values are: c:61.42%; h:3.55%; n:9.55%; o:3.64%; ir:21.84%;
the test values are: c:61.43%; h:3.54%; n:9.54%; o:3.63%; ir:21.85%.
By comparing the calculated value with the tested value, the tested value is basically consistent with the theoretical value, thus proving that the red organic electroluminescent material with the structural formula L009 can be successfully synthesized by the material example.
Material example 3
The embodiment of the material provides a red light organic electroluminescent material, the chemical structural formula of which is the formula L018 in the summary of the invention, and the reaction route of the preparation method of the red light organic electroluminescent material is as follows:
the preparation method specifically comprises the following steps:
s1, replacing the reactor with nitrogen, and adding the compound A-018 (85.2 mmol,25.50 g) and IrCl into the reactor under nitrogen atmosphere 3 ·3H 2 O (28.4 mmol,10 g), 600mL of ethylene glycol diethyl ether and 200mL of purified water are placed under nitrogen atmosphere and refluxed for 24 hours for heating reaction, then cooled to room temperature, precipitation is carried out, solid is obtained by suction filtration, and the solid is sequentially rinsed with 50mL of water, 50mL of absolute ethanol and 50mL of petroleum ether, and dried, thus obtaining red powdery bridged ligand B-018 (15.21 g, yield 65%).
S2, adopting nitrogen to replace a reactor, adding the bridging ligand B-018 (8 mmol,13.18 g) and the compound C-018 (24 mmol,3.72 g) into the reactor under the nitrogen atmosphere, adding 270mL of ethylene glycol diethyl ether and 11.04g of potassium carbonate into the system, placing the mixture in the nitrogen atmosphere, stirring the mixture at 120 ℃ for 24 hours for reaction, carrying out suction filtration, washing with alcohol, drying, using dichloromethane as an eluent, carrying out silica gel column chromatography, concentrating the filtrate, separating out solid, and carrying out suction filtration to finally obtain red-light organic electroluminescent material L018 (7.40 g, yield 49%).
The red light organic electroluminescent material L018 is detected and analyzed, and the specific results are as follows:
mass spectrometry: calculated 944.01; the test value was 945.13.
Elemental analysis:
the calculated values are: c:57.26%; h:3.95%; n:2.97%; o:3.36%; ir:20.36%; f:12.08;
the test values are: c:57.27%; h:3.94%; n:2.96%; o:3.37%; ir:20.37%; f:12.09.
by comparing the calculated value with the test value, the measured value is basically consistent with the theoretical value, thus proving that the red organic electroluminescent material with the structural formula L018 can be successfully synthesized by the material example.
Material example 4
The embodiment of the material provides a red light organic electroluminescent material, the chemical structural formula of which is the formula L026 in the summary of the invention, and the reaction route of the preparation method of the red light organic electroluminescent material is as follows:
the preparation method specifically comprises the following steps:
s1, replacing the reactor with nitrogen, and adding the compound A-026 (85.2 mmol,24.48 g) and IrCl into the reactor under the nitrogen atmosphere 3 ·3H 2 O (28.4 mmol,10 g), 600mL of ethylene glycol diethyl ether and 200mL of purified water are placed under nitrogen atmosphere and refluxed for 24 hours for heating reaction, then cooled to room temperature, precipitation is carried out, solid is obtained by suction filtration, and the solid is sequentially rinsed with 50mL of water, 50mL of absolute ethanol and 50mL of petroleum ether, and dried, thus obtaining red powdery bridged ligand B-026 (14.09 g, yield 62%).
S2, adopting nitrogen to replace a reactor, adding the bridging ligand B-026 (8 mmol,12.80 g) and the compound C-026 (24 mmol,3.72 g) into the reactor under the nitrogen atmosphere, adding 270mL of ethylene glycol diethyl ether and potassium carbonate (11.04 g) into the system, placing the mixture in the nitrogen atmosphere, stirring the mixture at 120 ℃ for 24 hours for reaction, then carrying out suction filtration, washing with alcohol, drying, using dichloromethane as an eluent, carrying out silica gel column chromatography, concentrating the filtrate, precipitating solid, and carrying out suction filtration to finally obtain red-light organic electroluminescent material L026 (7.50 g, yield 51%).
The red light organic electroluminescent material L026 is detected and analyzed, and the specific results are as follows:
mass spectrometry: calculated 920.23; the test value was 921.45.
Elemental analysis:
the calculated values are: c:66.57%; h:6.02%; n:3.04%; o:3.48%; ir:20.89%;
the test values are: c:66.58%; h:6.03%; n:3.05%; o:3.47%; ir:20.88%.
By comparing the calculated value with the test value, the measured value is basically consistent with the theoretical value, thus proving that the red organic electroluminescent material with the structural formula L026 can be successfully synthesized by the material example.
Material example 5
The embodiment of the material provides a red light organic electroluminescent material, the chemical structural formula of which is the formula L063 in the summary of the invention, and the reaction route of the preparation method of the red light organic electroluminescent material is as follows:
the preparation method specifically comprises the following steps:
s1, replacing the reactor with nitrogen, and adding a compound A-063 (85.2 mmol,25.50 g) and IrCl into the reactor under the atmosphere of nitrogen 3 ·3H 2 O (28.4 mmol,10 g), 600mL of ethylene glycol diethyl ether and 200mL of purified water are placed under nitrogen atmosphere and refluxed for 24 hours for heating reaction, then cooled to room temperature, precipitation is carried out, solid is obtained by suction filtration, and 50mL of water, 50mL of absolute ethanol and 50mL of petroleum ether are sequentially used for leaching, and drying is carried out, thus obtaining red powdery bridging ligand B-063 (14.74 g, yield is 63%).
S2, adopting nitrogen to replace a reactor, adding the bridging ligand B-063 (8 mmol,13.18 g) and the compound C-063 (24 mmol,2.52 g) into the reactor under the nitrogen atmosphere, adding 270mL of ethylene glycol diethyl ether and 11.04g of potassium carbonate into the system, placing the mixture in the nitrogen atmosphere, stirring the mixture at 120 ℃ for 24 hours for reaction, filtering the mixture, washing the mixture with alcohol, drying the mixture, using dichloromethane as an eluent, using a silica gel column for chromatography, concentrating the filtrate, separating out solids, and filtering the solid to obtain red organic electroluminescent material L063 (7.15 g, yield 46%).
The red light organic electroluminescent material L063 is detected and analyzed, and the specific results are as follows:
mass spectrometry: calculated 972.06; the test value was 973.15.
Elemental analysis:
the calculated values are: c:58.07%; h:4.25%; n:2.88%; o:3.29%; ir:19.77%; f:11.73;
the test values are: c:58.08%; h:4.26%; n:2.87%; o:3.28%; ir:19.78%; f:11.72.
by comparing the calculated value with the tested value, the tested value is basically consistent with the theoretical value, thus proving that the red organic electroluminescent material with the structural formula L063 can be successfully synthesized by the material embodiment.
Material example 6
The embodiment of the material provides a red light organic electroluminescent material, the chemical structural formula of which is the formula L079 in the summary of the invention, and the reaction route of the preparation method of the red light organic electroluminescent material is as follows:
the preparation method specifically comprises the following steps:
s1, replacing the reactor with nitrogen, and adding a compound A-079 (85.2 mmol,24.48 g) and IrCl into the reactor under the nitrogen atmosphere 3 ·3H 2 O (28.4 mmol,10 g), 600mL of ethylene glycol diethyl ether and 200mL of purified water are placed under nitrogen atmosphere and refluxed for 24 hours for heating reaction, then cooled to room temperature, precipitation is carried out, solid is obtained by suction filtration, and the solid is sequentially rinsed with 50mL of water, 50mL of absolute ethanol and 50mL of petroleum ether, and dried, thus obtaining red powdery bridged ligand B-079 (14.54 g, yield is 64%).
S2, adopting nitrogen to replace a reactor, adding the bridging ligand B-079 (8 mmol,12.80 g) and the compound C-079 (24 mmol,2.71 g) into the reactor under the nitrogen atmosphere, adding 270mL of ethylene glycol diethyl ether and 11.04g of potassium carbonate into the system, placing the mixture in the nitrogen atmosphere, stirring the mixture at 120 ℃ for 24 hours for reaction, then carrying out suction filtration, washing with alcohol, drying, using dichloromethane as an eluent, carrying out silica gel column chromatography, concentrating the filtrate, separating out solid, and carrying out suction filtration to finally obtain red-light organic electroluminescent material L079 (6.46 g, yield 46%).
The red light organic electroluminescent material L079 is detected and analyzed, and the specific result is as follows:
mass spectrometry: calculated 878.15; the test value was 879.21.
Elemental analysis:
the calculated values are: c:65.65%; h:5.62%; n:3.19%; o:3.64%; ir:21.89%;
the test values are: c:65.64%; h:5.63%; n:3.18%; o:3.65%; ir:21.88%.
By comparing the calculated value with the test value, the measured value is basically consistent with the theoretical value, thus proving that the red organic electroluminescent material with the structural formula L079 can be successfully synthesized by the material example.
Since the synthetic route and principle of the preparation method of other red organic electroluminescent materials with the general structural formula of formula I in the summary are the same as those of the above-listed material example 1, it is not exhaustive here, and a plurality of red organic electroluminescent materials are selected as material examples 7 to 16 in the present invention, and the specific details are shown in the following table 1.
TABLE 1
The embodiment of the invention also provides a device prepared from the red light organic electroluminescent material 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 a hole injection and hole transport skill layer, 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 an electron injection skill layer, and at least one of the layers may or may not include the above red light organic electroluminescent material, but is not limited thereto.
Specifically, the light-emitting layer includes a host material and a doping material; wherein, the main material can be 4,4'-N, N' -biphenyl dicarbazole, but is not limited to the above; the doping material can be selected from the red organic electroluminescent material.
In practical use, the method for manufacturing the organic electroluminescent device can be referred to the following device example 1.
Device example 1
Embodiment 1 of the device provides an organic electroluminescent device, and the preparation method thereof comprises the following steps:
s1, coating thickness is equal to
The ITO glass substrate is washed for 2 times in distilled water for 30 minutes by ultrasonic wave, repeatedly washed for 2 times by distilled water for 10 minutes by ultrasonic wave, and after the distilled water is washed, solvents such as isopropanol, acetone, methanol and the like are washed by ultrasonic wave in sequence, dried and transferred into a plasma washer, and the substrate is washed for 5 minutes and is sent into a vapor deposition machine for vapor deposition.
S2, firstly, evaporating CuPc on the ITO glass substrate (anode)
Subsequently, NPB is evaporated in sequence
Host material 4,4'-N, N' -biphenyl dicarbazole ("CBP") and dopant material (red organic electroluminescent material L001 described above) were mixed according to 95:5 weight ratio of the mixture>
Electron transport layer "Alq 3">
Electron injection layer LiF->
Cathode A1->
Thus obtaining the organic electroluminescent device.
Device examples 2 to 16
With reference to the preparation method provided in the above device example 1, device examples 2 to 16 were prepared, except that the red organic electroluminescent material L001 as the doping material in the above device example 1 was replaced with red organic electroluminescent materials L006, L008, L009, L012, L016, L017, L018, L024, L025, L026, L037, L042, L063, L068, L079, respectively, to prepare organic electroluminescent devices of the corresponding red organic electroluminescent materials.
Device comparative example 1
An organic electroluminescent device was fabricated as in device example 1, except that the red organic electroluminescent material L001, which is a doping material in the light-emitting layer, was replaced with a compound Ir (bty) 2 acac，Ir(bty) 2 The structural formula of acac is as follows:
experimental example:
1. the organic electroluminescent devices obtained in the above device examples 1 to 16 and device comparative example 1 were subjected to luminescence characteristic test using a KEITHLEY 2400-type source measuring unit and a CS-2000 spectroradiometer, respectively, to evaluate the driving voltage, lifetime (T95) and current efficiency of the devices, and the test results thereof are shown in Table 2 below.
TABLE 2
As can be seen from table 2 above, compared with the existing organic electroluminescent device provided in the device comparative example 1, the organic electroluminescent device manufactured by using the red organic electroluminescent material provided in the embodiment of the present invention can effectively reduce the driving voltage of the organic electroluminescent device, remarkably improve the current efficiency of the organic electroluminescent device, and prolong the service life of the organic electroluminescent device.
With the above-described preferred embodiments according to the present invention as an illustration, the above-described descriptions can be used by persons skilled in the relevant art to make various changes and modifications without departing from the scope of the technical idea of the present invention. The technical scope of the present invention is not limited to the description, but must be determined according to the scope of claims.
Claims (6)
1. The red light organic electroluminescent material is characterized by having a structural general formula as shown in formula I:
R 1 -R 9 each independently is any one of the following groups: hydrogen, deuterium, halogen, cyano, unsubstituted C1-C8 straight chain alkyl, branched alkyl, cycloalkyl, C1-C8 straight chain alkyl, branched alkyl, cycloalkyl substituted with deuterium or halogen; and R is 2 ~R 4 At least one substituent is deuterium, halogen or cyano.
2. The red light organic electroluminescent material according to claim 1, wherein the right side ligand of the metal Ir is selected from any one of the following structural formulas:
3. the red light organic electroluminescent material is characterized in that the chemical structural formula of the red light organic electroluminescent material is any one of the following structural formulas:
4. the method for preparing the red light organic electroluminescent material according to any one of claims 1 to 2, comprising the steps of:
taking a compound A with a structural formula of formula A and a compound C with a structural formula of formula C:
wherein R is 1 -R 9 Is as defined in any one of claims 1 to 2;
under the protective atmosphere, adding the compound A and iridium trichloride into a mixed solvent of ethylene glycol diethyl ether and water for heating reaction to obtain a bridging intermediate B;
and mixing the bridging intermediate B with the compound C, adding ethylene glycol diethyl ether and potassium carbonate, and placing the mixture in a protective atmosphere for reaction to obtain the red light organic electroluminescent material.
5. An organic electroluminescent device comprising a first electrode, a second electrode and at least one organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises the red organic electroluminescent material according to any one of claims 1 to 3.
6. The organic electroluminescent device according to claim 5, wherein the organic layer is a light-emitting layer; the light-emitting layer comprises a host material and a doping material; the doping material partially or completely contains the red light organic electroluminescent material.
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