CN112079875B - Organic electroluminescent material, preparation method thereof and organic electroluminescent device - Google Patents
Organic electroluminescent material, preparation method thereof and organic electroluminescent device Download PDFInfo
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- 239000000463 material Substances 0.000 title claims abstract description 113
- 238000002360 preparation method Methods 0.000 title abstract description 19
- 239000003446 ligand Substances 0.000 claims abstract description 46
- 229910052741 iridium Inorganic materials 0.000 claims abstract description 5
- 239000010410 layer Substances 0.000 claims description 40
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 239000012044 organic layer Substances 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 7
- -1 iridium metal complex Chemical class 0.000 claims description 6
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 3
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 2
- 229910021638 Iridium(III) chloride Inorganic materials 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 229910052805 deuterium Inorganic materials 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 abstract description 2
- 230000002035 prolonged effect Effects 0.000 abstract description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 238000001035 drying Methods 0.000 description 15
- 238000010438 heat treatment Methods 0.000 description 14
- 238000002347 injection Methods 0.000 description 13
- 239000007924 injection Substances 0.000 description 13
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- 238000005516 engineering process Methods 0.000 description 12
- 238000002386 leaching Methods 0.000 description 12
- 239000003208 petroleum Substances 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- 238000003828 vacuum filtration Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 230000005525 hole transport Effects 0.000 description 8
- 239000002346 layers by function Substances 0.000 description 8
- 238000001819 mass spectrum Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 239000012065 filter cake Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 238000004140 cleaning Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 4
- 238000000643 oven drying Methods 0.000 description 4
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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
- 238000000576 coating method Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
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- 239000002019 doping agent Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000004506 ultrasonic cleaning Methods 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
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000005540 biological transmission Effects 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
- 125000001424 substituent group Chemical group 0.000 description 2
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- 238000005303 weighing Methods 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
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 1
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920001090 Polyaminopropyl biguanide Polymers 0.000 description 1
- 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
- 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
- 239000011248 coating agent Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 150000008376 fluorenones Chemical class 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
- 238000007641 inkjet printing Methods 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-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
- 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
- 230000008569 process Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007650 screen-printing Methods 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- 150000003751 zinc Chemical class 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
-
- 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
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention discloses an organic electroluminescent material, a preparation method thereof and an organic electroluminescent device, belonging to the technical field of luminescent materials 1 )(L 2 ) x (L 3 ) y The general formula of the structure is:
Description
Technical Field
The invention relates to the technical field of luminescent materials, in particular to an organic electroluminescent material, a preparation method thereof and an organic electroluminescent device.
Background
With the explosive development of information technology in the 21 st century, information display technology has played an important role in the development of the human technology industry and in the improvement of quality of life. For decades, information display devices have evolved from the simplest light bulb indicator, seven segment digital display, to cathode ray tube display (CRT), to the present lightweight, compact, and energy efficient Liquid Crystal Display (LCD) and Plasma Display (PDP). However, these displays, although they have been improved and perfected considerably with respect to the conventional technologies, still cannot meet the urgent need of the increasingly advanced information age for the technology of high performance flat panel displays that are lighter, thinner and have lower power consumption cost, thus promoting the continuous search for more desirable and efficient display technologies.
As a novel flat panel display technology, the organic electroluminescent device (OLED) is light in weight, ultrathin, wide in viewing angle, flexible in display and strong in anti-seismic performance, and gradually enters the field of vision of researchers. In addition, the OLED technology can also be used for solid-state lighting, and compared with an inorganic light-emitting device, the OLED device has the advantages of firmness, self-luminescence, energy conservation, emission reduction and the like. Therefore, OLED technology has the potential to become the mainstream technology of solid-state lighting, and becomes another important application field besides flat panel display application.
The organic electroluminescent material is taken as a spotlighting phosphorescent material, has short excited state life and high quantum efficiency, can easily adjust the luminescent color of the complex molecule by modifying a ligand, and is the most potential OLED luminescent material; however, the current organic electroluminescent materials applied to organic electroluminescent devices have the problems of higher driving voltage, lower current efficiency and the like.
Therefore, a new organic electroluminescent material is urgently needed to be developed, so that the driving voltage of the organic electroluminescent device is obviously reduced, and the current efficiency is obviously improved.
Disclosure of Invention
An object of the embodiments of the present invention is to provide an organic electroluminescent material to solve the problems of the background art mentioned above.
Specifically, the embodiment of the invention provides an organic electroluminescent material, whichIs an iridium metal complex of the formula Ir (L) 1 )(L 2 ) x (L 3 ) y The general structural formula is shown as formula I:
wherein x and y are both natural numbers, and x + y =2.
Preferably, L 2 、L 3 Each independently is at least one of the following ligands:
in the formula, R a 、R b 、R c 、R d And R e Each independently is one or more of hydrogen, deuterium, halogen, cyano, nitro, C1-C8 alkyl, C1-C8 alkoxy, C6-C18 aryl, and C4-C12 aromatic heterocyclic group.
Preferably, the C1-C8 alkyl is one of a straight-chain alkyl group, a branched-chain alkyl group and a cyclic alkyl group which are unsubstituted or substituted by at least one substituent group.
Preferably, the substituent group is one or more of methyl, ethyl, isopropyl, tert-butyl and isobutyl.
Preferably, L 1 Is one of the following ligands:
preferably, the chemical structural formula of the organic electroluminescent material is any one of formulas I-001 to I-099:
another objective of an embodiment of the present invention is to provide a method for preparing the above organic electroluminescent material, which includes the following steps:
the ligand L in the formula I 2 And/or L 3 Reacting with iridium trichloride to obtain a bridged ligand;
the bridging ligand B is reacted with the ligand L in the formula I 1 And carrying out reaction to obtain the organic electroluminescent material.
It is another object of an embodiment of the present invention to provide an organic electroluminescent device, which includes a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, wherein the organic layer includes the above-mentioned 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 comprises the organic electroluminescent material.
Another object of the embodiments of the present invention is to provide an application of the above organic electroluminescent material in the preparation of organic electroluminescent devices.
Preferably, the mass ratio of the host material to the doping material is (90-99.5) to (0.5-10).
Specifically, the first electrode is an anode, and the kind thereof is not particularly limited, and may be a conventional anode known to those skilled in the art, and more preferably, is one of ITO (indium tin oxide), tin oxide, zinc oxide, and indium oxide, and has a thickness of 10 to 500nm. The second electrode is a cathode, the kind of which is not particularly limited, and may be a conventional cathode known to those skilled in the art, and more preferably is one of Al, li, na, K, mg, ca, au, ag, and Pb, and has a thickness of 100 to 1000nm.
The main material is preferably one or more of 4,4'-N, N' -biphenyl dicarbazole (CBP), octahydroxyquinoline (Alq 3), metal phenoxybenzothiazole compounds, polyfluorenes, aromatic condensed rings and zinc complexes. The thickness of the light-emitting layer is 10 to 500nm.
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-1, 4-diamine), phthalocyanine and porphyrin compounds, starburst triarylamine, a conductive polymer, an N-type semi-conductive 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 transmission 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 transmission layer is 10-500 nm.
The electron injection layer is LiF, csF or Li 2 O、Al 2 O 3 And 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 organic electroluminescent device may be 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 following beneficial effects:
the organic electroluminescent material provided by the embodiment of the invention is prepared by combining metal iridium with a specific heterocyclic ligand, and after the organic electroluminescent material is used for organic electroluminescent devices such as organic electroluminescent devices, the driving voltage of the organic electroluminescent devices can be reduced, the current efficiency of the organic electroluminescent devices can be obviously improved, and the service life of the organic electroluminescent devices can be prolonged. In addition, the preparation method of the organic electroluminescent material provided by the embodiment of the invention has the characteristics of simple synthesis steps, non-harsh condition requirements and high yield of target products, and solves the problems of high synthesis price and higher 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.
Materials example 1
The embodiment of the material provides an organic electroluminescent material, the chemical structural formula of which is shown as formula I-005 in the summary of the invention, and the reaction route of the preparation method of the organic electroluminescent material is as follows:
step 1: ligand A-005 (47.36mmol, 10g) and IrCl were weighed 3 ·3H 2 O (18.94mmol, 6.67g), ethylene glycol ethyl ether (150 mL), and water (50 mL) were added to the reaction system, respectively, under N 2 Heating and refluxing for 24h under protection, then cooling to room temperature, separating out precipitate, performing vacuum filtration, sequentially leaching with anhydrous ethanol and petroleum ether, and oven drying to obtain bridged ligand B-005 with mass of 11.16g and yield of 91%;
step 2: the bridging ligand B-005 (8.48mmol, 11g), K was weighed 2 CO 3 (26mmol, 3.60g) and ethylene glycol ethyl ether (50 mL) were added to the reaction system separately under N 2 Adding ligand C-005 (shown in formula 5) (25.44mmol, 5.7 g) under protection, heating to 120 deg.C, heating and refluxing for 24h, cooling to room temperature, vacuum filtering, leaching filter cake with ethanol and petroleum ether, oven drying at-0.1MPa and 50 deg.C, passing through silica gel column, and spin drying the obtained filtrate to obtain target product I-005, i.e. organic electroluminescent material (6.98mmol, 5.85g), with yield of 41.2%.
HPLC purity of the organic electroluminescent material: 99 percent.
Mass spectrum of the organic electroluminescent material: theoretical value 837.42; the measured structure was substantially identical to the theoretical structure at test value 837.19.
Wherein the structural formula of the ligand C-005 is as follows:
material example 2
The embodiment provides an organic electroluminescent material, the chemical structural formula of which is formula I-007 in the summary of the invention, and the reaction route of the preparation method of the organic electroluminescent material is as follows:
the specific preparation method comprises the following steps:
step 1: ligand A-007 (50.73mmol, 10g) and IrCl were weighed 3 ·3H 2 O (20.29mmol, 7.16g), ethylene glycol ethyl ether (150 mL), and water (50 mL) were added to the reaction system in N 2 Heating and refluxing for 24h under protection, cooling to room temperature, separating out precipitate, vacuum filtering, sequentially leaching with anhydrous ethanol and petroleum ether, and oven drying to obtain bridged ligand B-007 with mass of 11.33g and yield of 90.1%;
step 2: the bridged ligand B-007 (8.86mmol, 11g), K was weighed 2 CO 3 (26mmol, 3.60g) and ethylene glycol ethyl ether (50 mL) were added to the reaction system separately under N 2 Adding ligand C-007 (shown as formula 6) (26.58mmol, 6.32g) under protection, heating to 120 ℃, refluxing for 24h, cooling to room temperature, carrying out vacuum filtration, leaching a filter cake with ethanol and petroleum ether, drying at-0.1MPa and 50 ℃, passing through a silica gel column, and finally, carrying out spin drying on the obtained filtrate to obtain a target product I-007 which is an organic electroluminescent material (7.18mmol, 5.92g), wherein the yield is 40.6%.
HPLC purity of the organic electroluminescent material: is more than 99 percent.
Mass spectrum of the organic electroluminescent material: theoretical value 823.85; the test value is 823.21, and the measured structure is basically consistent with the theoretical structure.
Wherein the structural formula of the ligand C-007 is as follows:
material example 3
The embodiment provides an organic electroluminescent material, the chemical structural formula of which is formula I-020 in the summary of the invention, and the reaction route of the preparation method of the organic electroluminescent material is as follows:
the specific preparation method comprises the following steps:
step 1: ligand A-020 (36.58mmol, 10g) and IrCl were weighed 3 ·3H 2 O (14.63mmol, 5.15g), ethylene glycol ethyl ether (150 mL), and water (50 mL) were added to the reaction system, respectively, under N 2 Heating and refluxing for 24h under protection, then cooling to room temperature, separating out precipitate, performing vacuum filtration, sequentially leaching with anhydrous ethanol and petroleum ether, and drying to obtain bridging ligand B-020 with a mass of 10.2g and a yield of 90.3%;
step 2: the bridged ligand B-020 (6.47mmol, 10g), K was weighed 2 CO 3 (26mmol, 3.60g) and ethylene glycol ethyl ether (50 mL) were added to the reaction system separately under N 2 Adding ligand C-020 (19.41mmol, 4.35g) under protection, raising the temperature to 120 ℃, heating and refluxing for 24h, cooling to room temperature, carrying out vacuum filtration, leaching a filter cake with ethanol and petroleum ether, drying at-0.1MPa and 50 ℃, passing through a silica gel column, and finally spin-drying the obtained filtrate to obtain a target product I-020, namely the organic electroluminescent material (5.06mmol, 4.87g), wherein the yield is 39.2%.
HPLC purity of the organic electroluminescent material: 99 percent.
Mass spectrum of the organic electroluminescent material: theoretical value 961.33; the test value 961.45, the measured structure is substantially consistent with the theoretical structure.
Wherein the structural formula of the ligand C-020 is as follows:
material example 4
The embodiment provides an organic electroluminescent material, the chemical structural formula of which is formula I-022 in the summary of the invention, and the reaction route of the preparation method of the organic electroluminescent material is as follows:
the specific preparation method comprises the following steps:
step 1: ligand A-022 (33.17mmol, 10g) and IrCl were weighed 3 ·3H 2 O (13.27mmol, 4.67g), ethylene glycol ethyl ether (150 mL), and water (50 mL) were added to the reaction system under N 2 Heating and refluxing for 24h under protection, then cooling to room temperature, separating out precipitate, performing vacuum filtration, sequentially leaching with anhydrous ethanol and petroleum ether, and oven drying to obtain bridged ligand B-022, with a mass of 10g and a yield of 91%;
step 2: the bridging ligand B-022 (6.03mmol, 10g), K, was weighed 2 CO 3 (26mmol, 3.60g) and ethylene glycol ethyl ether (50 mL) were added to the reaction system separately under N 2 Adding ligand C-022 (18.09mmol, 4.3 g) under protection, heating to 120 ℃, refluxing for 24h, cooling to room temperature, vacuum filtering, leaching the filter cake with ethanol and petroleum ether, drying at-0.1MPa and 50 ℃, passing through a silica gel column, and finally spin-drying the obtained filtrate to obtain a target product I-022, namely the organic electroluminescent material (4.52mmol, 4.67g), wherein the yield is 37.6%.
HPLC purity of the organic electroluminescent material: 99 percent.
Mass spectrum of the organic electroluminescent material: theoretical value 1031.15; and testing the value 1031.32, wherein the measured structure is basically consistent with the theoretical structure.
Wherein the structural formula of the ligand C-022 is as follows:
material example 5
This example provides an organic electroluminescent material, whose chemical structural formula is formula I-045 in the summary of the invention, and the reaction route of the preparation method of the organic electroluminescent material is as follows:
the specific preparation method comprises the following steps:
step 1: ligand A-045 (34.68mmol, 10g) and IrCl were weighed 3 ·3H 2 O (13.87mmol, 4.89g), ethylene glycol ethyl ether (150 mL), and water (50 mL) were added to the reaction system, respectively, under N 2 Heating and refluxing for 24h under protection, then cooling to room temperature, separating out precipitates, carrying out vacuum filtration, sequentially leaching with absolute ethyl alcohol and petroleum ether, and drying to obtain bridging ligand B-045 with the mass of 11g and the yield of 99%;
step 2: weighing bridging ligand B-001 (6.85mmol, 11g), K 2 CO 3 (26mmol, 3.60g) and ethylene glycol ethyl ether (50 mL) were added to the reaction system separately under N 2 Adding ligand C-045 (20.55mmol, 4.6 g) under protection, raising the temperature to 120 ℃, heating and refluxing for 24h, cooling to room temperature, carrying out vacuum filtration, leaching a filter cake with ethanol and petroleum ether, drying at-0.1MPa and 50 ℃, passing through a silica gel column, and finally spin-drying the obtained filtrate to obtain a target product I-045, namely the organic electroluminescent material (5.75mmol, 5.71g), wherein the yield is 42.1%.
HPLC purity of the organic electroluminescent material: 99 percent.
Mass spectrum of the organic electroluminescent material: theoretical value 991.36; the tested structure is basically consistent with the theoretical structure under the test value of 991.47.
Wherein the structural formula of the ligand C-045 is as follows:
material example 6
The embodiment provides an organic electroluminescent material, a chemical structural formula of which is shown as formula I-064 in the summary of the invention, and a reaction route of a preparation method of the organic electroluminescent material is as follows:
the specific preparation method comprises the following steps:
step 1: ligand A-064 (39.72mmol, 10g) and IrCl were weighed 3 ·3H 2 O (11.89mmol, 4.19g), ethylene glycol ethyl ether (150 mL) and water (50 mL) were added to the reaction system, respectively, under N 2 Heating and refluxing for 24h under protection, then cooling to room temperature, separating out precipitate, performing vacuum filtration, sequentially leaching with anhydrous ethanol and petroleum ether, and drying to obtain bridging ligand B-064 with a mass of 11g and a yield of 97%;
step 2: weighing bridging ligand B-064 (5.77mmol, 11g), K 2 CO 3 (26mmol, 3.60g) and ethylene glycol ethyl ether (50 mL) were added to the reaction system separately under N 2 Adding ligand C-064 (17.31mmol, 2.91g) under protection, heating to 120 ℃, heating and refluxing for 24h, cooling to room temperature, carrying out vacuum filtration, leaching a filter cake with ethanol and petroleum ether, drying at-0.1MPa and 50 ℃, passing through a silica gel column, and finally spin-drying the obtained filtrate to obtain a target product I-064, namely the organic electroluminescent material (3.98mmol, 4.33g), wherein the yield is 34.6%.
HPLC purity of the organic electroluminescent material: is more than 99 percent.
Mass spectrum of the organic electroluminescent material: theoretical value 1085.38; the tested structure was substantially identical to the theoretical structure, tested value 1085.41.
Wherein the structural formula of the ligand C-064 is as follows:
material examples 7 to 18
Because the synthetic route and the principle of the preparation method of other organic electroluminescent materials with the structural general formula of formula I in the summary of the invention are similar to those of the material example 1 listed above, only corresponding ligands need to be replaced, so that the list is not exhausted, and the invention selects a plurality of organic electroluminescent materials as the material examples 7-18, which are specifically shown in the following table 1.
TABLE 1
Organic electroluminescent material | Structural formula (I) | Molecular formula | Calculated mass spectrum | Mass spectrometric test values |
Materials example 7 | I-001 | C 30 H 30 IrN 3 O | 641.20 | 641.81 |
Material example 8 | I-008 | C 38 H 46 IrN 3 O | 753.33 | 753.02 |
Material example 9 | I-018 | C 46 H 46 IrN 3 O | 849.33 | 849.11 |
Material example 10 | I-027 | C 60 H 66 D 8 IrN 3 O | 1053.6 | 1053.54 |
Material example 11 | I-035 | C 52 H 60 IrN 5 O | 963.44 | 963.31 |
Material example 12 | I-038 | C 54 H 64 IrN 5 O | 991.47 | 991.36 |
Material example 13 | I-042 | C 58 H 64 D 8 IrN 5 O | 1055.59 | 1055.62 |
Material example 14 | I-050 | C 54 H 62 IrN 3 O | 961.45 | 961.33 |
Material example 15 | I-054 | C 52 H 52 F 6 IrN 3 O | 1041.36 | 1041.22 |
Material example 16 | I-057 | C 60 H 66 D 8 IrN 3 O | 1053.6 | 1053.51 |
Material example 17 | I-062 | C 56 H 44 F 2 IrN 3 O 3 | 1037.3 | 1037.38 |
Material example 18 | I-070 | C 56 H 40 F 6 IrN 3 O 3 | 1109.26 | 1109.16 |
The embodiment of the invention also provides an organic electroluminescent device prepared by adopting the organic electroluminescent material provided by the embodiment, and specifically, 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 technology layer, 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 an electron injection technology layer, and at least one of the layers may or may not include the organic electroluminescent material, but is not limited thereto.
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 doped material can be selected from the organic electroluminescent materials.
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:
coating with a thickness ofThe ITO glass substrate is placed in distilled water for cleaning for 2 times, ultrasonic cleaning is carried out for 30 minutes, distilled water is used for repeatedly cleaning for 2 times, ultrasonic cleaning is carried out for 10 minutes, after the cleaning of distilled water is finished, solvents such as isopropanol, acetone, methanol and the like are used for carrying out ultrasonic cleaning in sequence, drying is carried out, the ITO glass substrate is transferred to a plasma cleaning machine for cleaning for 5 minutes, and then the ITO glass substrate is sent to an evaporation machine for evaporation according to the following method;
(1) Firstly, an ITO glass substrate (anode) is evaporated to a thickness ofN, N '-diphenyl-N, N' -di (1-naphthyl) -1,1 '-biphenyl-4, 4' -diamine (NPB) as a hole transport layer, followed by mixed evaporation of 4'-N, N' -biphenyl dicarbazole ("CBP") and the organic electroluminescent material of formula I-005 provided in the above material example 1 as a light emitting layer on the hole transport layer at a mass ratio of 95.
(2) Under the same vacuum deposition condition, tris (8-hydroxyquinoline) aluminum (Alq 3),) Acting as an electron-transport layer>LiF as an electron injection layer>The Al is used as a cathode, and the organic electroluminescent device can be obtained.
Device examples 2 to 18
An organic electroluminescent device was prepared by referring to the preparation methods provided in device example 1 above, except that the organic electroluminescent material I-005 (dopant material) in device example 1 above was replaced with the organic electroluminescent material I-001, I-007, I-008, I-018, I-020, I-022, I-027, I-035, I-038, I-042, I-045, I-050, I-054, I-057, I-062, I-064, I-070, respectively, to prepare 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 that the organic electroluminescent material I-005 (dopant material) in device example 1 above was replaced with the existing iridium metal complex Ir (bty) 2 acac, wherein, ir (bty) 2 The structural formula of acac is as follows:
experimental example:
the organic electroluminescent devices obtained in the device examples 1 to 18 and the device comparative example 1 were tested for performance and emission characteristics under the same luminance conditions using a KEITHLEY model 2400 source measurement unit and a CS-2000 spectroradiometer to evaluate driving voltage, current efficiency and emission lifetime (T95) of the organic electroluminescent devices, and the specific test results are shown in table 2.
TABLE 2
As can be seen from Table 2 above, ir (bty) is provided in comparison to comparative example 1 of the device 2 The organic electroluminescent device prepared by using the organic electroluminescent material provided by the embodiment of the invention as the doping material can effectively reduce the driving voltage of the organic electroluminescent 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 (5)
1. The organic electroluminescent material is characterized in that the organic electroluminescent material is an iridium metal complex with a chemical formula of Ir (L) 1 )(L 2 ) x (L 3 ) y The general structural formula is shown as formula I:
wherein x and y are both natural numbers, and x + y =2;
L 2 、L 3 each independently is at least one of the following ligands:
in the formula, R a 、R b 、R c 、R d And R e Are respectively and independently one or more of hydrogen, deuterium, halogen, cyano, nitro, C1-C8 alkyl and C1-C8 alkoxy;
L 1 is one of the following ligands:
3. a method for preparing the organic electroluminescent material according to claim 1, comprising the steps of:
the ligand L in the formula I 2 And/or L 3 Reacting with iridium trichloride to obtain a bridged ligand B;
the bridging ligand B is reacted with the ligand L in the formula I 1 And carrying out reaction to obtain the organic electroluminescent material.
4. An organic electroluminescent device comprising a first electrode, a second electrode and at least one organic layer disposed between said first electrode and said second electrode, characterized in that said organic layer comprises an organic electroluminescent material as claimed in any one of claims 1 to 2.
5. An organic electroluminescent device according to claim 4, 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 completely comprises the organic electroluminescent material.
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