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
- Publication number
- CN112079875B CN112079875B CN202010930515.7A CN202010930515A CN112079875B CN 112079875 B CN112079875 B CN 112079875B CN 202010930515 A CN202010930515 A CN 202010930515A CN 112079875 B CN112079875 B CN 112079875B
- Authority
- CN
- China
- Prior art keywords
- organic electroluminescent
- electroluminescent material
- ligand
- formula
- organic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System 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
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 of
The 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 of
N, 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:
2. an organic electroluminescent material, characterized in that the chemical structural formula of the organic electroluminescent material is any one of the following structural formulas:
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.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010930515.7A CN112079875B (en) | 2020-09-07 | 2020-09-07 | Organic electroluminescent material, preparation method thereof and organic electroluminescent device |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010930515.7A CN112079875B (en) | 2020-09-07 | 2020-09-07 | Organic electroluminescent material, preparation method thereof and organic electroluminescent device |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN112079875A CN112079875A (en) | 2020-12-15 |
| CN112079875B true CN112079875B (en) | 2023-04-18 |
Family
ID=73733129
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010930515.7A Active CN112079875B (en) | 2020-09-07 | 2020-09-07 | Organic electroluminescent material, preparation method thereof and organic electroluminescent device |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN112079875B (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006000544A2 (en) * | 2004-06-28 | 2006-01-05 | Ciba Specialty Chemicals Holding Inc. | Electroluminescent metal complexes with triazoles and benzotriazoles |
| CN101652375A (en) * | 2007-02-14 | 2010-02-17 | 巴斯夫欧洲公司 | Electroluminescent metal complex |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7582757B2 (en) * | 2006-09-06 | 2009-09-01 | E. I. Du Pont De Nemours And Company | Electroluminescent complexes of Ir(III) and devices |
-
2020
- 2020-09-07 CN CN202010930515.7A patent/CN112079875B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006000544A2 (en) * | 2004-06-28 | 2006-01-05 | Ciba Specialty Chemicals Holding Inc. | Electroluminescent metal complexes with triazoles and benzotriazoles |
| CN101652375A (en) * | 2007-02-14 | 2010-02-17 | 巴斯夫欧洲公司 | Electroluminescent metal complex |
Non-Patent Citations (3)
| Title |
|---|
| Highly Efficient Red-Emitting Bis-Cyclometalated Iridium Complexes;Po-Ni Lai等;《Journal of the American Chemical Society》;20180721;第140卷(第32期);第10199页Scheme 1化合物1 * |
| Manipulating the Excited States of Cyclometalated Iridium Complexes with β‑Ketoiminate and β‑Diketiminate Ligands;Yousf K. Radwan等;《Inorganic Chemistry》;20150709;第54卷(第14期);第7123页Scheme 1，第7129页左栏最后一段 * |
| Po-Ni Lai等.Highly Efficient Red-Emitting Bis-Cyclometalated Iridium Complexes.《Journal of the American Chemical Society》.2018,第140卷(第32期), * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN112079875A (en) | 2020-12-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102017220B (en) | Compound for organic electric field light-emitting element and organic electric field light-emitting element | |
| CN102017221B (en) | Compound for organic electroluminescent elements and organic electroluminescent element | |
| KR101996649B1 (en) | Pyrene derivative compounds and organic light-emitting diode including the same | |
| CN100469204C (en) | Organic electroluminescent element | |
| KR101111120B1 (en) | Aromatic compound and organic electroluminescent device using the same | |
| KR102053569B1 (en) | Multicyclic compound and organic light emitting device comprising the same | |
| CN106518603B (en) | Organic material and organic electroluminescent module using the same | |
| CN113024529B (en) | Organic electroluminescent material and organic electroluminescent device | |
| KR20150105201A (en) | New organic electroluminescent compounds and organic electroluminescent device comprising the same | |
| KR20110123701A (en) | Anthracene-based compound and organic electroluminescent devices comprising the same | |
| CN111875640A (en) | Organic phosphorus optical compound, preparation method thereof and photoelectric device | |
| KR20120066390A (en) | Anthracene deriva tives and organic light-emitting diode including the same | |
| CN112010908B (en) | Iridium complex for red light electroluminescent material, preparation method thereof and photoelectric device | |
| CN112759617B (en) | Iridium-matched organic electroluminescent material and preparation method and application thereof | |
| KR20130121597A (en) | Using triphenylamine as hole transporting mateial and organic electroluminescent device using the same | |
| CN112939890A (en) | Heterocyclic organic photoelectric material, preparation method thereof and organic electroluminescent device | |
| CN114975839B (en) | Organic electroluminescent device, organic electroluminescent device and photoelectric equipment | |
| CN111004201A (en) | Organic electroluminescent compound, preparation method thereof and organic electroluminescent device | |
| CN112939990B (en) | Luminescent compound with organic condensed rings, preparation method thereof and organic electroluminescent device | |
| CN114447245A (en) | Organic electroluminescent device and display device | |
| CN111848687B (en) | Red light organic electroluminescent material, preparation method thereof and photoelectric device | |
| CN110845421A (en) | Electron transport compound, synthesis method thereof and organic electroluminescent device | |
| CN112079875B (en) | Organic electroluminescent material, preparation method thereof and organic electroluminescent device | |
| KR20150095208A (en) | Novel hole injecting· hole-transporting compound and organic electroluminescent device comprising same | |
| KR101779914B1 (en) | Naphthalene derivatives and organic light-emitting diode including the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |